An official website of the United States government

Bromobenzyl Cyanide

PubChem CID
22044
Structure
Bromobenzyl Cyanide_small.png
Bromobenzyl Cyanide_3D_Structure.png
Molecular Formula
Synonyms
  • Bromobenzyl cyanide
  • 5798-79-8
  • 2-bromo-2-phenylacetonitrile
  • Bromo(phenyl)acetonitrile
  • Camite
Molecular Weight
196.04 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2005-03-27
  • Modify:
    2025-01-25
Description
Bromobenzyl cyanides appears as a chemical warfare tear gas agent. A mixture of isomers: 2-bromobenzyl cyanide is a liquid (melting point 34 °F); 3-bromobenzyl cyanide is a pale yellow crystalline solid melting at 77 °F to give a colorless liquid; 4-bromobenzyl cyanide is a solid melting at 118 °F. All are denser than water and insoluble in water. Hence sink in water. Lachrymator: the vapors are irritating to the eyes and mucous membranes. Exposure to high concentrations may be fatal. Produces toxic oxides of nitrogen during combustion.
Bromobenzyl cyanide is a colorless organobromide compound. It is slightly soluble in water but readily soluble in organic solvents. Bromobenzyl cyanide is resistant to the action of water and oxidizers; it decomposes upon heating above 120° C and also when exposed to the action of a number of metals, which are thereby intensely corroded. Bromobenzyl cyanide is obtained by the action of sodium cyanide or potassium cyanide on benzyl chloride with subsequent bromination of the benzyl cyanide that has been formed. Bromobenzyl cyanide acts powerfully on the mucous membranes of the eye, causing irritation and heavy lachrymation. It was proposed as a toxic lachrymatory agent at the end of World War I and an irritant gas for law enforcement. It is chemically and biologically similar to Benzyl cyanide. Benzyl cyanide and its derivatives are used in organic synthesis for dyes, perfumes, pesticides, pharmaceuticals, especially penicillin precursors.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
Bromobenzyl Cyanide.png

1.2 3D Conformer

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

2-bromo-2-phenylacetonitrile
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

2.1.2 InChI

InChI=1S/C8H6BrN/c9-8(6-10)7-4-2-1-3-5-7/h1-5,8H
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.3 InChIKey

XUHFBOUSHUEAQZ-UHFFFAOYSA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.4 SMILES

C1=CC=C(C=C1)C(C#N)Br
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C8H6BrN
Computed by PubChem 2.2 (PubChem release 2021.10.14)

2.3 Other Identifiers

2.3.1 CAS

19472-74-3

31938-07-5

16532-79-9

5798-79-8

2.3.2 European Community (EC) Number

2.3.3 UNII

2.3.4 UN Number

2.3.5 ChEMBL ID

2.3.6 DSSTox Substance ID

2.3.7 Nikkaji Number

2.3.8 Pharos Ligand ID

2.3.9 Wikidata

2.3.10 Wikipedia

2.4 Synonyms

2.4.1 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
196.04 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3-AA
Property Value
2.5
Reference
Computed by XLogP3 3.0 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Donor Count
Property Value
0
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Acceptor Count
Property Value
1
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
1
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
194.96836 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
194.96836 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
23.8 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
10
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
141
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Isotope Atom Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Atom Stereocenter Count
Property Value
1
Reference
Computed by PubChem
Property Name
Defined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Covalently-Bonded Unit Count
Property Value
1
Reference
Computed by PubChem
Property Name
Compound Is Canonicalized
Property Value
Yes
Reference
Computed by PubChem (release 2021.10.14)

3.2 Experimental Properties

3.2.1 Physical Description

Bromobenzyl cyanides appears as a chemical warfare tear gas agent. A mixture of isomers: 2-bromobenzyl cyanide is a liquid (melting point 34 °F); 3-bromobenzyl cyanide is a pale yellow crystalline solid melting at 77 °F to give a colorless liquid; 4-bromobenzyl cyanide is a solid melting at 118 °F. All are denser than water and insoluble in water. Hence sink in water. Lachrymator: the vapors are irritating to the eyes and mucous membranes. Exposure to high concentrations may be fatal. Produces toxic oxides of nitrogen during combustion.
Pale yellow crystals; [CAMEO] Yellowish solid with an odor of soured fruit; mp = 29 deg C; [HSDB] Pure: Yellow to white solid; Impure: Oily brown liquid; [EPA OHM/TADS]

3.2.2 Color / Form

YELLOWISH CRYSTALS FROM DILUTE ALCOHOL
Weast, R.C. (ed.). Handbook of Chemistry and Physics. 60th ed. Boca Raton, Florida: CRC Press Inc., 1979., p. C-89

3.2.3 Odor

ODOR OF SOURED FRUIT
The Merck Index. 9th ed. Rahway, New Jersey: Merck & Co., Inc., 1976., p. 181

3.2.4 Boiling Point

242 °C @ 760 MM HG
The Merck Index. 9th ed. Rahway, New Jersey: Merck & Co., Inc., 1976., p. 181

3.2.5 Melting Point

77 °F
29 °C
Weast, R.C. (ed.). Handbook of Chemistry and Physics. 60th ed. Boca Raton, Florida: CRC Press Inc., 1979., p. C-89

3.2.6 Solubility

SLIGHTLY SOL IN WATER; FREELY SOL IN ALCOHOL, ETHER, ACETONE, CHLOROFORM, COMMON ORGANIC SOLVENTS; SOL IN PHOSGENE, CHLOROPICRIN, BENZYL CYANIDE
The Merck Index. 9th ed. Rahway, New Jersey: Merck & Co., Inc., 1976., p. 181

3.2.7 Density

1.539 @ 29 °C/4 °C
Weast, R.C. (ed.). Handbook of Chemistry and Physics. 60th ed. Boca Raton, Florida: CRC Press Inc., 1979., p. C-89

3.2.8 Vapor Density

6.8 (AIR= 1)
The Merck Index. 9th ed. Rahway, New Jersey: Merck & Co., Inc., 1976., p. 181

3.2.9 Vapor Pressure

0.00465 [mmHg]
0.012 MM HG @ 20 °C
The Merck Index. 9th ed. Rahway, New Jersey: Merck & Co., Inc., 1976., p. 181

3.2.10 Odor Threshold

LOWEST DETECTABLE LEVEL: 0.09 MG/CU M
Clayton, G. D. and F. E. Clayton (eds.). Patty's Industrial Hygiene and Toxicology: Volume 2A, 2B, 2C: Toxicology. 3rd ed. New York: John Wiley Sons, 1981-1982., p. 4892

3.2.11 Other Experimental Properties

MELTS TO AN OILY LIQ JUST ABOVE ROOM TEMP
Grant, W. M. Toxicology of the Eye. 2nd ed. Springfield, Illinois: Charles C. Thomas, 1974., p. 202
BROWN, OILY LIQUID /TECHNICAL PRODUCT/
Sax, N.I. Dangerous Properties of Industrial Materials. 4th ed. New York: Van Nostrand Reinhold, 1975., p. 474

3.3 Chemical Classes

Toxic Gases & Vapors -> Tear Gas Agents

4 Spectral Information

4.1 Mass Spectrometry

4.1.1 GC-MS

1 of 2
Source of Spectrum
F-52-9639-0
Copyright
Copyright © 2020-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail
2 of 2
Source of Spectrum
AD-0-2532-0
Copyright
Copyright © 2020-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail

4.2 UV Spectra

MAX ABSORPTION (HEXANE): 235 NM (LOG E= 3.8)
Weast, R.C. (ed.). Handbook of Chemistry and Physics. 60th ed. Boca Raton, Florida: CRC Press Inc., 1979., p. C-89

6 Chemical Vendors

7 Drug and Medication Information

7.1 Reported Fatal Dose

109 ppm is lethal to humans in 5 hours; or 0.9 mg/L for 30 minutes.

8 Pharmacology and Biochemistry

8.1 Metabolism / Metabolites

Bromobenzyl cyanide is metabolized into bromobenzoic acid and thiocyanate, probably via hydroxylation to mandelonitrile. Hydrolysis of the cyanide group to give phenylacetic acid or bromophenylacetic occurs as minor pathway. Any liberated cyanide is mainly metabolized into thiocyanate by either rhodanese or 3-mercaptopyruvate sulfur transferase. Cyanide metabolites are excreted in the urine. Organic nitriles are converted into cyanide ions through the action of cytochrome P450 enzymes in the liver. Cyanide is rapidly absorbed and distributed throughout the body. Cyanide is mainly metabolized into thiocyanate by either rhodanese or 3-mercaptopyruvate sulfur transferase. Cyanide metabolites are excreted in the urine. (L96)
L96: ATSDR - Agency for Toxic Substances and Disease Registry (2006). Toxicological profile for cyanide. U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA). http://www.atsdr.cdc.gov/toxprofiles/tp8.html

9 Use and Manufacturing

9.1 Uses

Sources/Uses
Used as a war gas and irritant gas for law enforcement; [HSDB]
WAR GAS
The Merck Index. 9th ed. Rahway, New Jersey: Merck & Co., Inc., 1976., p. 181
IRRITANT GAS USED BY LAW ENFORCEMENT AGENCIES.
SASS S ET AL; GAS/LIQUID CHROMATOGRAPHY (GLC) OF SOME IRRITANTS AT VARIOUS CONCN; ANAL CHEM 43(3) 462 (1971)
Bromobenzyl cyanide is an industrial and laboratory chemical. Occupational exposure to Bromobenzyl cyanide may occur through inhalation and dermal contact with this compound at workplaces where Bromobenzyl cyanide is produced or used.

9.1.1 Use Classification

Hazard Classes and Categories ->

9.2 Methods of Manufacturing

PRACTICAL INDUSTRIAL PREPARATION CONSISTS OF 3 STEPS: (1) CHLORINATION OF TOLUENE TO FORM BENZYL CHLORIDE, (2) CONVERSION OF BENZYL CHLORIDE TO BENZYL CYANIDE BY ACTION OF SODIUM CYANIDE IN ALCOHOLIC SOLN... (3) BROMINATION OF BENZYL CYANIDE WITH BROMIDE VAPOR IN PRESENCE OF SUNLIGHT. STEINKOPF ET AL, BER 53, 1146 (1920); NEKRASSOV, J PRAKT CHEM 119, 108 (1928).
The Merck Index. 9th ed. Rahway, New Jersey: Merck & Co., Inc., 1976., p. 181

10 Identification

10.1 Analytic Laboratory Methods

IRRITANT GAS USED BY MILITARY AND LAW ENFORCEMENT AGENCIES CAN BE DETERMINED BY GAS LIQ CHROMATOGRAPHY.
SASS S ET AL; GAS/LIQUID CHROMATOGRAPHY (GLC) OF SOME IRRITANTS AT VARIOUS CONCN; ANAL CHEM 43(3) 462 (1971)

11 Safety and Hazards

11.1 Hazards Identification

11.1.1 GHS Classification

Pictogram(s)
Irritant
Signal
Warning
GHS Hazard Statements

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]

H319 (97.4%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]

H335 (100%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

Precautionary Statement Codes

P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501

(The corresponding statement to each P-code can be found at the GHS Classification page.)

ECHA C&L Notifications Summary

Aggregated GHS information provided per 39 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

11.1.2 Hazard Classes and Categories

Acute Tox. 4 (100%)

Skin Irrit. 2 (100%)

Eye Irrit. 2 (97.4%)

STOT SE 3 (100%)

11.1.3 Health Hazards

For information on chemical warfare tear gas agents see the ERG Criminal or Terrorist Use of CBR Agents. (ERG, 2024)

Excerpt from ERG Guide 159 [Substances (Irritating)]:

Inhalation of vapors or dust is extremely irritating. May cause burning of eyes and lachrymation (flow of tears). May cause coughing, difficult breathing and nausea. Brief exposure effects last only a few minutes. Exposure in an enclosed area may be very harmful. Fire will produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may cause environmental contamination. (ERG, 2024)

ERG 2024, Guide 159 (Bromobenzyl cyanides, solid; Bromobenzyl cyanides, liquid)

· Inhalation of vapors or dust is extremely irritating.

· May cause burning of eyes and lachrymation (flow of tears).

· May cause coughing, difficult breathing and nausea.

· Brief exposure effects last only a few minutes.

· Exposure in an enclosed area may be very harmful.

· Fire will produce irritating, corrosive and/or toxic gases.

· Runoff from fire control or dilution water may cause environmental contamination.

11.1.4 Fire Hazards

For information on chemical warfare tear gas agents see the ERG Criminal or Terrorist Use of CBR Agents. (ERG, 2024)

Excerpt from ERG Guide 159 [Substances (Irritating)]:

Some of these materials may burn, but none ignite readily. Containers may explode when heated. (ERG, 2024)

ERG 2024, Guide 159 (Bromobenzyl cyanides, solid; Bromobenzyl cyanides, liquid)

· Some of these materials may burn, but none ignite readily.

· Containers may explode when heated.

11.1.5 Hazards Summary

A lachrymator; [HSDB] Exposure to high concentrations may be fatal; [CAMEO] Extremely toxic; 109 ppm is lethal to humans in 5 hours; [EPA OHM/TADS]

11.1.6 Fire Potential

DISASTER HAZARD: SEE CYANIDES. DANGEROUS; ON CONTACT WITH ACID, ACID FUMES, WATER OR STEAM, THEY WILL PRODUCE...FLAMMABLE VAPORS. /CYANIDES/
Sax, N.I. Dangerous Properties of Industrial Materials. 4th ed. New York: Van Nostrand Reinhold, 1975., p. 474

11.1.7 Skin, Eye, and Respiratory Irritations

STRONG LACRIMATOR
The Merck Index. 9th ed. Rahway, New Jersey: Merck & Co., Inc., 1976., p. 181

11.2 First Aid Measures

11.2.1 First Aid

For information on chemical warfare tear gas agents see the ERG Criminal or Terrorist Use of CBR Agents. (ERG, 2024)

Excerpt from ERG Guide 159 [Substances (Irritating)]:

Refer to the "General First Aid" section. (ERG, 2024)

ERG 2024, Guide 159 (Bromobenzyl cyanides, solid; Bromobenzyl cyanides, liquid)

General First Aid:

· Call 911 or emergency medical service.

· Ensure that medical personnel are aware of the material(s) involved, take precautions to protect themselves and avoid contamination.

· Move victim to fresh air if it can be done safely.

· Administer oxygen if breathing is difficult.

· If victim is not breathing:

-- DO NOT perform mouth-to-mouth resuscitation; the victim may have ingestedor inhaled the substance.

-- If equipped and pulse detected, wash face and mouth, then give artificial respiration using a proper respiratory medical device (bag-valve mask, pocket mask equipped with a one-way valve or other device).

-- If no pulse detected or no respiratory medical device available, provide continuouscompressions. Conduct a pulse check every two minutes or monitor for any signs of spontaneous respirations.

· Remove and isolate contaminated clothing and shoes.

· For minor skin contact, avoid spreading material on unaffected skin.

· In case of contact with substance, remove immediately by flushing skin or eyes with running water for at least 20 minutes.

· For severe burns, immediate medical attention is required.

· Effects of exposure (inhalation, ingestion, or skin contact) to substance may be delayed.

· Keep victim calm and warm.

· Keep victim under observation.

· For further assistance, contact your local Poison Control Center.

· Note: Basic Life Support (BLS) and Advanced Life Support (ALS) should be done by trained professionals.

In Canada, an Emergency Response Assistance Plan (ERAP) may be required for this product. Please consult the shipping paper and/or the "ERAP" section.

11.3 Fire Fighting

For information on chemical warfare tear gas agents see the ERG Criminal or Terrorist Use of CBR Agents. (ERG, 2024)

Excerpt from ERG Guide 159 [Substances (Irritating)]:

SMALL FIRE: Dry chemical, CO2, water spray or regular foam.

LARGE FIRE: Water spray, fog or regular foam. If it can be done safely, move undamaged containers away from the area around the fire. Dike runoff from fire control for later disposal.

FIRE INVOLVING TANKS, RAIL TANK CARS OR HIGHWAY TANKS: Fight fire from maximum distance or use unmanned master stream devices or monitor nozzles. Do not get water inside containers. Cool containers with flooding quantities of water until well after fire is out. Withdraw immediately in case of rising sound from venting safety devices or discoloration of tank. ALWAYS stay away from tanks in direct contact with flames. For massive fire, use unmanned master stream devices or monitor nozzles; if this is impossible, withdraw from area and let fire burn. (ERG, 2024)

11.4 Accidental Release Measures

Public Safety: ERG 2024, Guide 159 (Bromobenzyl cyanides, solid; Bromobenzyl cyanides, liquid)

· CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.

· Keep unauthorized personnel away.

· Stay upwind, uphill and/or upstream.

· Ventilate closed spaces before entering, but only if properly trained and equipped.

Spill or Leak: ERG 2024, Guide 159 (Bromobenzyl cyanides, solid; Bromobenzyl cyanides, liquid)

· Do not touch or walk through spilled material.

· Stop leak if you can do it without risk.

Small Spill

· Pick up with sand or other non-combustible absorbent material and place into containers for later disposal.

Large Spill

· Dike far ahead of liquid spill for later disposal.

· Prevent entry into waterways, sewers, basements or confined areas.

11.4.1 Isolation and Evacuation

For initial isolation and protective action distances for chemical warfare tear gas agents see the Chemical Warfare Agents table in the ERG Criminal or Terrorist Use of CBR Agents. (ERG, 2024)

Excerpt from ERG Guide 159 [Substances (Irritating)]:

IMMEDIATE PRECAUTIONARY MEASURE: Isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids.

LARGE SPILL: Consider initial downwind evacuation for at least 100 meters (330 feet).

FIRE: If tank, rail tank car or highway tank is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2024)

Evacuation: ERG 2024, Guide 159 (Bromobenzyl cyanides, solid; Bromobenzyl cyanides, liquid)

Immediate precautionary measure

· Isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids.

Large Spill

· Consider initial downwind evacuation for at least 100 meters (330 feet).

Fire

· If tank, rail tank car or highway tank is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions.

11.5 Handling and Storage

11.5.1 Nonfire Spill Response

For information on chemical warfare tear gas agents see the ERG Criminal or Terrorist Use of CBR Agents. (ERG, 2024)

Excerpt from ERG Guide 159 [Substances (Irritating)]:

Do not touch or walk through spilled material. Stop leak if you can do it without risk.

SMALL SPILL: Pick up with sand or other non-combustible absorbent material and place into containers for later disposal.

LARGE SPILL: Dike far ahead of liquid spill for later disposal. Prevent entry into waterways, sewers, basements or confined areas. (ERG, 2024)

11.6 Exposure Control and Personal Protection

Protective Clothing: ERG 2024, Guide 159 (Bromobenzyl cyanides, solid; Bromobenzyl cyanides, liquid)

· Wear positive pressure self-contained breathing apparatus (SCBA).

· Wear chemical protective clothing that is specifically recommended by the manufacturer when there is NO RISK OF FIRE.

· Structural firefighters' protective clothing provides thermal protection but only limited chemical protection.

Maximum Allowable Concentration (MAK)
2.0 [mg/m3], inhalable fraction, as CN[German Research Foundation (DFG)]

11.6.1 Permissible Exposure Limit (PEL)

5.0 [mg/m3], as CN

11.6.2 Immediately Dangerous to Life or Health (IDLH)

25.0 [mg/m3], as CN

11.6.3 Emergency Response Planning Guidelines

Emergency Response: ERG 2024, Guide 159 (Bromobenzyl cyanides, solid; Bromobenzyl cyanides, liquid)

Small Fire

· Dry chemical, CO2, water spray or regular foam.

Large Fire

· Water spray, fog or regular foam.

· If it can be done safely, move undamaged containers away from the area around the fire.

· Dike runoff from fire control for later disposal.

Fire Involving Tanks, Rail Tank Cars or Highway Tanks

· Fight fire from maximum distance or use unmanned master stream devices or monitor nozzles.

· Do not get water inside containers.

· Cool containers with flooding quantities of water until well after fire is out.

· Withdraw immediately in case of rising sound from venting safety devices or discoloration of tank.

· ALWAYS stay away from tanks in direct contact with flames.

· For massive fire, use unmanned master stream devices or monitor nozzles; if this is impossible, withdraw from area and let fire burn.

11.6.4 Personal Protective Equipment (PPE)

For information on chemical warfare tear gas agents see the ERG Criminal or Terrorist Use of CBR Agents. (ERG, 2024)

Excerpt from ERG Guide 159 [Substances (Irritating)]:

Wear positive pressure self-contained breathing apparatus (SCBA). Wear chemical protective clothing that is specifically recommended by the manufacturer when there is NO RISK OF FIRE. Structural firefighters' protective clothing provides thermal protection but only limited chemical protection. (ERG, 2024)

11.7 Stability and Reactivity

11.7.1 Air and Water Reactions

Insoluble in water.

11.7.2 Reactive Group

Nitriles

Aryl Halides

11.7.3 Reactivity Profile

BROMOBENZYL CYANIDES may polymerize in the presence of metals and some metal compounds. Incompatible with acids. Mixing with strong oxidizing acids can lead to extremely violent reactions. Generally incompatible with other oxidizing agents such as peroxides and epoxides (peroxides convert nitriles to amides). Combination with bases can produce hydrogen cyanide. Hydrolyzed in both aqueous acid and base to give carboxylic acids (or salts of carboxylic acids). These reactions generate heat. Can react vigorously with reducing agents.

11.8 Transport Information

11.8.1 DOT Emergency Guidelines

/GUIDE 159: SUBSTANCES (IRRITATING)/ Health: Inhalation of vapors or dust is extremely irritating. May cause burning of eyes and flow of tears. May cause coughing, difficult breathing and nausea. Brief exposure effects last only a few minutes. Exposure in an enclosed area may be very harmful. Fire will produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may cause pollution. /Bromobenzyl cyanides; Bromobenzyl cyanides, liquid; Bromobenzyl cyanides, solid/
U.S. Department of Transportation. 2004 Emergency Response Guidebook. A Guide book for First Responders During the Initial Phase of a Dangerous Goods/Hazardous Materials Incident. Washington, D.C. 2004
/GUIDE 159: SUBSTANCES (IRRITATING)/ Fire or Explosion: Some of these materials may burn, but none ignite readily. Containers may explode when heated. /Bromobenzyl cyanides; Bromobenzyl cyanides, liquid; Bromobenzyl cyanides, solid/
U.S. Department of Transportation. 2004 Emergency Response Guidebook. A Guide book for First Responders During the Initial Phase of a Dangerous Goods/Hazardous Materials Incident. Washington, D.C. 2004
/GUIDE 159: SUBSTANCES (IRRITATING)/ Public Safety: CALL Emergency Response Telephone Number ... . As an immediate precautionary measure, isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids. Keep unauthorized personnel away. Stay upwind. Keep out of low areas. Ventilate closed spaces before entering. /Bromobenzyl cyanides; Bromobenzyl cyanides, liquid; Bromobenzyl cyanides, solid/
U.S. Department of Transportation. 2004 Emergency Response Guidebook. A Guide book for First Responders During the Initial Phase of a Dangerous Goods/Hazardous Materials Incident. Washington, D.C. 2004
/GUIDE 159: SUBSTANCES (IRRITATING)/ Protective Clothing: Wear positive pressure self-contained breathing apparatus (SCBA). Wear chemical protective clothing that is specifically recommended by the manufacturer. It may provide little or no thermal protection. Structural firefighters' protective clothing provides limited protection in fire situations ONLY; it is not effective in spill situations where direct contact with the substance is possible. /Bromobenzyl cyanides; Bromobenzyl cyanides, liquid; Bromobenzyl cyanides, solid/
U.S. Department of Transportation. 2004 Emergency Response Guidebook. A Guide book for First Responders During the Initial Phase of a Dangerous Goods/Hazardous Materials Incident. Washington, D.C. 2004
For more DOT Emergency Guidelines (Complete) data for ALPHA-BROMOBENZYL CYANIDE (8 total), please visit the HSDB record page.

11.8.2 Shipment Methods and Regulations

No person may /transport,/ offer or accept a hazardous material for transportation in commerce unless that person is registered in conformance ... and the hazardous material is properly classed, described, packaged, marked, labeled, and in condition for shipment as required or authorized by ... /the hazardous materials regulations (49 CFR 171-177)./
49 CFR 171.2 (7/1/96)
The International Maritime Dangerous Goods Code lays down basic principles for transporting hazardous chemicals. Detailed recommendations for individual substances and a number of recommendations for good practice are included in the classes dealing with such substances. A general index of technical names has also been compiled. This index should always be consulted when attempting to locate the appropriate procedures to be used when shipping any substance or article.
IMDG; International Maritime Dangerous Goods Code; International Maritime Organization p.6081 (1988)

11.8.3 DOT Label

Poison

12 Toxicity

12.1 Toxicological Information

12.1.1 Toxicity Summary

Organic nitriles decompose into cyanide ions both in vivo and in vitro. Consequently the primary mechanism of toxicity for organic nitriles is their production of toxic cyanide ions or hydrogen cyanide. Cyanide is an inhibitor of cytochrome c oxidase in the fourth complex of the electron transport chain (found in the membrane of the mitochondria of eukaryotic cells). It complexes with the ferric iron atom in this enzyme. The binding of cyanide to this cytochrome prevents transport of electrons from cytochrome c oxidase to oxygen. As a result, the electron transport chain is disrupted and the cell can no longer aerobically produce ATP for energy. Tissues that mainly depend on aerobic respiration, such as the central nervous system and the heart, are particularly affected. Cyanide is also known produce some of its toxic effects by binding to catalase, glutathione peroxidase, methemoglobin, hydroxocobalamin, phosphatase, tyrosinase, ascorbic acid oxidase, xanthine oxidase, succinic dehydrogenase, and Cu/Zn superoxide dismutase. Cyanide binds to the ferric ion of methemoglobin to form inactive cyanmethemoglobin. (L97)
L97: Wikipedia. Cyanide poisoning. Last Updated 30 March 2009. http://en.wikipedia.org/wiki/Cyanide_poisoning

12.1.2 Carcinogen Classification

Carcinogen Classification
No indication of carcinogenicity (not listed by IARC). (L135)

12.1.3 Health Effects

Strong lachrymator. On exposure to eyes, corneal corpuscles become swollen and brownish during first 24 hr. This is followed by infiltration of cornea by macrophages, loss of normal endothelial reflex and appearance of fine irregularity in endothelium. Harmful if inhaled, swallowed or absorbed through skin. Target organs: central nervous system, blood, lungs, cardiovascular system, thyroid.

12.1.4 Exposure Routes

Oral (L626) ; inhalation (L626) ; dermal (L626)
L626: International Programme on Chemical Safety (IPCS) INCHEM (1992). Poison Information Monograph for Bromine. http://www.inchem.org/documents/pims/chemical/pim080.htm

12.1.5 Symptoms

Causes severe eye and skin burns. Irritating to eyes, skin, and respiratory system. Acute exposure (ingestion or inhalation) can lead to coma, seizures, palpitations, dilated pupils, hypoventilation, shock, cyanosis, initial tachycardia and hypertension, and hypotension may be seen. Nausea, vomiting, and metabolic acidosis may occur.

12.1.6 Adverse Effects

Lacrimator (Lachrymator) - A substance that irritates the eyes and induces the flow of tears.

12.1.7 Acute Effects

12.1.8 Toxicity Data

LC (mouse) > 1,160 mg/m3
Insupportable at 5 mg/m3.

12.1.9 Minimum Risk Level

Minimal Effective Concentration: 0.2 mg/m3

12.1.10 Treatment

EYES: irrigate opened eyes for several minutes under running water. INGESTION: do not induce vomiting. Rinse mouth with water (never give anything by mouth to an unconscious person). Seek immediate medical advice. SKIN: should be treated immediately by rinsing the affected parts in cold running water for at least 15 minutes, followed by thorough washing with soap and water. If necessary, the person should shower and change contaminated clothing and shoes, and then must seek medical attention. INHALATION: supply fresh air. If required provide artificial respiration.

12.1.11 Human Toxicity Excerpts

STRONG LACRIMATOR.
The Merck Index. 9th ed. Rahway, New Jersey: Merck & Co., Inc., 1976., p. 181
CHANGES INDUCED IN ONE HUMAN EYE... CORNEAL CORPUSCLES BECOME SWOLLEN & BROWNISH DURING FIRST 24 HR. THIS IS FOLLOWED BY INFILTRATION OF CORNEA BY MACROPHAGES, LOSS OF NORMAL ENDOTHELIAL REFLEX, & APPEARANCE OF FINE IRREGULARITY IN ENDOTHELIUM.
Grant, W. M. Toxicology of the Eye. 2nd ed. Springfield, Illinois: Charles C. Thomas, 1974., p. 203
UNLIKELY TO LIBERATE MUCH CYANIDE, BUT IF CYANIDE TOXICITY IS PRESENT THEN TREAT FOR CYANIDE POISONING.
LETHAL CONCN: 0.90 MG/LITER (30 MIN)...
The Merck Index. 9th ed. Rahway, New Jersey: Merck & Co., Inc., 1976., p. 181

12.1.12 Non-Human Toxicity Excerpts

CHANGES INDUCED IN RABBIT EYES EXPERIMENTALLY... CORNEAL CORPUSCLES BECOME SWOLLEN & BROWNISH DURING FIRST 24 HR. ...FOLLOWED BY INFILTRATION OF CORNEA BY MACROPHAGES, LOSS OF NORMAL ENDOTHELIAL REFLEX, & APPEARANCE OF FINE IRREGULARITY IN ENDOTHELIUM.
Grant, W. M. Toxicology of the Eye. 2nd ed. Springfield, Illinois: Charles C. Thomas, 1974., p. 203

12.2 Ecological Information

12.2.1 Probable Routes of Human Exposure

SEE CYANIDES. WORKERS...WHO ARE DAILY EXPOSED TO CYANIDE SOLN MAY DEVELOP 'CYANIDE' RASH, CHARACTERIZED BY ITCHING, AND BY MACULAR, PAPULAR, AND VESICULAR ERUPTIONS. FREQUENTLY THERE IS SECONDARY INFECTION. /CYANIDES/
Sax, N.I. Dangerous Properties of Industrial Materials. 4th ed. New York: Van Nostrand Reinhold, 1975., p. 474
...EFFECTS OF VARIOUS LEVELS IN AIR... LOWEST DETECTABLE LEVEL: 0.09 MG/CU M; LOWEST IRRITANT CONCN: 0.15 MG/CU M; INTOLERABLE CONCN: 0.8 MG/CU M (10 MIN).
Clayton, G. D. and F. E. Clayton (eds.). Patty's Industrial Hygiene and Toxicology: Volume 2A, 2B, 2C: Toxicology. 3rd ed. New York: John Wiley Sons, 1981-1982., p. 4892

13 Literature

13.1 Consolidated References

13.2 Springer Nature References

13.3 Thieme References

13.4 Chemical Co-Occurrences in Literature

13.5 Chemical-Gene Co-Occurrences in Literature

13.6 Chemical-Disease Co-Occurrences in Literature

14 Patents

14.1 Depositor-Supplied Patent Identifiers

14.2 WIPO PATENTSCOPE

14.3 Chemical Co-Occurrences in Patents

14.4 Chemical-Disease Co-Occurrences in Patents

14.5 Chemical-Gene Co-Occurrences in Patents

15 Interactions and Pathways

15.1 Chemical-Target Interactions

16 Biological Test Results

16.1 BioAssay Results

17 Classification

17.1 ChemIDplus

17.2 CAMEO Chemicals

17.3 ChEMBL Target Tree

17.4 UN GHS Classification

17.5 NORMAN Suspect List Exchange Classification

17.6 EPA DSSTox Classification

17.7 EPA Substance Registry Services Tree

17.8 MolGenie Organic Chemistry Ontology

18 Information Sources

  1. CAMEO Chemicals
    LICENSE
    CAMEO Chemicals and all other CAMEO products are available at no charge to those organizations and individuals (recipients) responsible for the safe handling of chemicals. However, some of the chemical data itself is subject to the copyright restrictions of the companies or organizations that provided the data.
    https://cameochemicals.noaa.gov/help/reference/terms_and_conditions.htm?d_f=false
    CAMEO Chemical Reactivity Classification
    https://cameochemicals.noaa.gov/browse/react
  2. CAS Common Chemistry
    LICENSE
    The data from CAS Common Chemistry is provided under a CC-BY-NC 4.0 license, unless otherwise stated.
    https://creativecommons.org/licenses/by-nc/4.0/
  3. ChemIDplus
    ChemIDplus Chemical Information Classification
    https://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
  4. EPA DSSTox
    CompTox Chemicals Dashboard Chemical Lists
    https://comptox.epa.gov/dashboard/chemical-lists/
  5. European Chemicals Agency (ECHA)
    LICENSE
    Use of the information, documents and data from the ECHA website is subject to the terms and conditions of this Legal Notice, and subject to other binding limitations provided for under applicable law, the information, documents and data made available on the ECHA website may be reproduced, distributed and/or used, totally or in part, for non-commercial purposes provided that ECHA is acknowledged as the source: "Source: European Chemicals Agency, http://echa.europa.eu/". Such acknowledgement must be included in each copy of the material. ECHA permits and encourages organisations and individuals to create links to the ECHA website under the following cumulative conditions: Links can only be made to webpages that provide a link to the Legal Notice page.
    https://echa.europa.eu/web/guest/legal-notice
  6. FDA Global Substance Registration System (GSRS)
    LICENSE
    Unless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required.
    https://www.fda.gov/about-fda/about-website/website-policies#linking
  7. Hazardous Substances Data Bank (HSDB)
  8. NJDOH RTK Hazardous Substance List
  9. Haz-Map, Information on Hazardous Chemicals and Occupational Diseases
    LICENSE
    Copyright (c) 2022 Haz-Map(R). All rights reserved. Unless otherwise indicated, all materials from Haz-Map are copyrighted by Haz-Map(R). No part of these materials, either text or image may be used for any purpose other than for personal use. Therefore, reproduction, modification, storage in a retrieval system or retransmission, in any form or by any means, electronic, mechanical or otherwise, for reasons other than personal use, is strictly prohibited without prior written permission.
    https://haz-map.com/About
  10. Toxin and Toxin Target Database (T3DB)
    LICENSE
    T3DB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (T3DB) and the original publication.
    http://www.t3db.ca/downloads
  11. Emergency Response Guidebook (ERG)
  12. ChEMBL
    LICENSE
    Access to the web interface of ChEMBL is made under the EBI's Terms of Use (http://www.ebi.ac.uk/Information/termsofuse.html). The ChEMBL data is made available on a Creative Commons Attribution-Share Alike 3.0 Unported License (http://creativecommons.org/licenses/by-sa/3.0/).
    http://www.ebi.ac.uk/Information/termsofuse.html
  13. Japan Chemical Substance Dictionary (Nikkaji)
  14. Pharos
    LICENSE
    Data accessed from Pharos and TCRD is publicly available from the primary sources listed above. Please respect their individual licenses regarding proper use and redistribution.
    https://pharos.nih.gov/about
  15. SpectraBase
    2-Bromanyl-2-phenyl-ethanenitrile
    https://spectrabase.com/spectrum/4bIQXf2cR6W
    2-Bromanyl-2-phenyl-ethanenitrile
    https://spectrabase.com/spectrum/4rBF3jNSZbw
  16. Springer Nature
  17. Thieme Chemistry
    LICENSE
    The Thieme Chemistry contribution within PubChem is provided under a CC-BY-NC-ND 4.0 license, unless otherwise stated.
    https://creativecommons.org/licenses/by-nc-nd/4.0/
  18. Wikidata
  19. Wikipedia
  20. PubChem
  21. GHS Classification (UNECE)
  22. NORMAN Suspect List Exchange
    LICENSE
    Data: CC-BY 4.0; Code (hosted by ECI, LCSB): Artistic-2.0
    https://creativecommons.org/licenses/by/4.0/
    NORMAN Suspect List Exchange Classification
    https://www.norman-network.com/nds/SLE/
  23. EPA Substance Registry Services
  24. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  25. PATENTSCOPE (WIPO)
  26. NCBI
CONTENTS