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Bromodichloroacetic Acid

PubChem CID
114809
Structure
Bromodichloroacetic Acid_small.png
Bromodichloroacetic Acid_3D_Structure.png
Molecular Formula
Synonyms
  • Bromodichloroacetic acid
  • 71133-14-7
  • 2-bromo-2,2-dichloroacetic acid
  • Dichlorobromoacetic acid
  • Acetic acid,2-bromo-2,2-dichloro-
Molecular Weight
207.83 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2005-08-08
  • Modify:
    2025-01-18
Description
Bromodichloroacetic acid can cause cancer according to The National Toxicology Program.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
Bromodichloroacetic Acid.png

1.2 3D Conformer

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

2-bromo-2,2-dichloroacetic acid
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

2.1.2 InChI

InChI=1S/C2HBrCl2O2/c3-2(4,5)1(6)7/h(H,6,7)
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.3 InChIKey

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

2.1.4 SMILES

C(=O)(C(Cl)(Cl)Br)O
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C2HBrCl2O2
Computed by PubChem 2.2 (PubChem release 2021.10.14)

2.3 Other Identifiers

2.3.1 CAS

2.3.2 European Community (EC) Number

2.3.3 UNII

2.3.4 ChEMBL ID

2.3.5 DSSTox Substance ID

2.3.6 Nikkaji Number

2.3.7 Wikidata

2.4 Synonyms

2.4.1 MeSH Entry Terms

  • bromodichloroacetate
  • bromodichloroacetic acid

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
207.83 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3-AA
Property Value
1.8
Reference
Computed by XLogP3 3.0 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Donor Count
Property Value
1
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Acceptor Count
Property Value
2
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
205.85370 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
205.85370 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
37.3 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
7
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
91.7
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
0
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 Henry's Law Constant

Henry's Law constant = 7.9X10-9 atm-cu m/mole at 25 °C
USEPA; Estimation Program Interface (EPI) Suite. Ver. 3.12. Nov 30, 2004. Available from, as of July 3, 2008: https://www.epa.gov/oppt/exposure/docs/episuitedl.htm

3.2.2 Stability / Shelf Life

Stable
Sigma-Aldrich; Material Safety Data Sheet for Bromodichloroacetic Acid, 100mg, neat (PN: 442499) 5 pp. (September 5, 2002) Available from, as of July 31, 2008: https://www.sigmaaldrich.com/catalog/search/ProductDetail/SUPELCO/442499

3.2.3 Decomposition

Sigma-Aldrich; Material Safety Data Sheet for Bromodichloroacetic Acid, 100mg, neat (PN: 442499) 5 pp. (September 5, 2002) Available from, as of July 31, 2008: https://www.sigmaaldrich.com/catalog/search/ProductDetail/SUPELCO/442499

5 Chemical Vendors

6 Agrochemical Information

6.1 Agrochemical Category

Microbiocide

7 Pharmacology and Biochemistry

7.1 Absorption, Distribution and Excretion

The oral and iv elimination kinetics were investigated for bromodichloroacetate (BDCA) ... BDCA was administered at a dose of 5, 20 and 100 mg/kg to B6C3F1 mice and appears to distribute to the total body water with a mean volume of distribution of 427 +/- 79 mL/kg. It is subject to first-pass hepatic metabolism with a range of bioavailabilities of 0.28-0.73. A mean terminal half-life of 1.37 +/- 0.21 hr was calculated from the two lower doses of both iv and oral administration. Non-linear behavior was exhibited at doses greater than 20 mg/kg, with a much higher than expected area under the curve (AUC), a decrease in total body clearance (CL(b)) and an increase in the terminal half-life to 2.3 hr at the highest dose. The average CL(b) was 220 mL/hr/kg for the lower two doses but decreased to 156 mL/hr/kg at the high dose. The BDCA is primarily eliminated by metabolism, with only 2.4% of the parent dose being recovered in the urine at the high dose. The unbound renal clearance, as calculated from the high dose, was 15.0 mL/hr/kg. The BDCA is moderately bound to plasma proteins (f(u) = 0.28) and preferentially distributes to the plasma with a blood/plasma ratio of 0.88.
Merdink JL et al; J Appl Toxicol 21 (1): 53-7 (2001)
As the bromodichloroacetic (BDCA) acid dose is increased from 20 to 100 mg/kg of body weight in the rat, the fraction of the dose that is eliminated in the urine as dichloroacetic acid (DCA) increases from about 2% to 13%, whereas in mice the increase is from 0.2% to approximately 3%.
Environmental Health Criteria 216: Disinfectants and DIsinfectant By-Products (1999) by the International Programme on Chemical Safety (IPCS) under the joint sponsorship of the United Nations Environment Programme, the International Labour Organisation and the World Health Organization. Available from, as of August 1, 2008: https://www.inchem.org/documents/ehc/ehc/ehc216.htm

7.2 Metabolism / Metabolites

... /Unlike some other trihaloacetates/ bromodichloroacetate (BDCA) ... does not induce peroxisome proliferation even at high doses. This study attempts to determine whether differences in the metabolism of the trihaloacetates (THAs) may contribute to their differing toxicological properties. Studies were performed in male B6C3F1 mice given (14C1,2) trichloroacetic acid (TCA), (14C1)BDCA, and (14C1,2) dichloroacetic acid (DCA) by gavage. The replacement of a Cl by a Br greatly enhances THA metabolism. Much less radiolabel from BDCA is retained in the carcass after 24 hr than from TCA. Radiolabel from BDCA is largely found in the urine, with oxalate being the major metabolite. TCA is largely eliminated unchanged in the urine. There are dose-related changes in the rate of CO2 production from BDCA. The initial rate of CO2 production is reduced from 4.1 +/- 0.3 hr-1 at 5 and 20 mg/kg to 2.7 +/- 0.6 hr-1 at 100 mg/kg, but the net conversion to CO2 in 24 hr is greater at the highest dose. As would be predicted, substitution Br for Cl on TCA greatly increased its metabolism.
Xu G et al; Drug Metab Dispos 23 (12): 1412-6 (1995)
/Investigators/ studied the metabolism of BDCA in male B6C3F1 mice. As predicted, substitution of a bromine for a chlorine in TCA resulted in a substantially greater extent of trihaloacetate metabolism. Whereas 45% of a 100 mg/kg of body weight dose of TCA was eliminated unchanged in the urine of mice within 24 hr, less than 4% of the same dose of BDCA was found in the urine. At lower doses, only a fraction of a percent of the BDCA was eliminated unchanged.
Environmental Health Criteria 216: Disinfectants and DIsinfectant By-Products (1999) by the International Programme on Chemical Safety (IPCS) under the joint sponsorship of the United Nations Environment Programme, the International Labour Organisation and the World Health Organization. Available from, as of August 1, 2008: https://www.inchem.org/documents/ehc/ehc/ehc216.htm
The metabolism of BDCA is differentially modified in mice and rats as doses are increased. /Investigators/ found that the kinetics of carbon dioxide production from 1-(14)C-BDCA suggested an efficient conversion of BDCA to carbon dioxide through DCA at low doses, but a direct decarboxylation reaction became important as doses approached 100 mg/kg of body weight. This complex activity was not observed in rats, in that a progressively smaller fraction of the dose is converted to carbon dioxide as dose is increased. This suggests that direct decarboxylation plays a less important role in the metabolism of BDCA in rats than in mice.
Environmental Health Criteria 216: Disinfectants and DIsinfectant By-Products (1999) by the International Programme on Chemical Safety (IPCS) under the joint sponsorship of the United Nations Environment Programme, the International Labour Organisation and the World Health Organization. Available from, as of August 1, 2008: https://www.inchem.org/documents/ehc/ehc/ehc216.htm
The ratios of urinary metabolites produced by mice and rats suggest that there are some substantive differences in the metabolism of BDCA in the two species. Mice produce much higher amounts of oxalate (about 30% of the orally administered dose) than do rats (about 20%). The much greater conversion of BDCA to oxalate than for equivalent doses of DCA suggests that much of the extra oxalate seen in mouse urine arises from reductive dehalogenation of BDCA, followed by peroxy radical formation and decomposition to oxalate.
Environmental Health Criteria 216: Disinfectants and DIsinfectant By-Products (1999) by the International Programme on Chemical Safety (IPCS) under the joint sponsorship of the United Nations Environment Programme, the International Labour Organisation and the World Health Organization. Available from, as of August 1, 2008: https://www.inchem.org/documents/ehc/ehc/ehc216.htm
For more Metabolism/Metabolites (Complete) data for BROMODICHLOROACETIC ACID (6 total), please visit the HSDB record page.

7.3 Biological Half-Life

... Bromodichloroacetate (BDCA) was administered at a dose of 5, 20 and 100 mg/kg... A mean terminal half-life of 1.37 +/- 0.21 hr was calculated from the two lower doses of both iv and oral administration. Non-linear behavior was exhibited at doses greater than 20 mg/kg, with ... an increase in the terminal half-life to 2.3 hr at the highest dose...
Merdink JL et al; J Appl Toxicol 21 (1): 53-7 (2001)
In the rat, increasing the dose from 5 mg/kg of body weight to 20 or 100 mg/kg of body weight was associated with a significantly extended half-life of both BDCA and DCA (from 0.9 to 3.7 hr).
Environmental Health Criteria 216: Disinfectants and DIsinfectant By-Products (1999) by the International Programme on Chemical Safety (IPCS) under the joint sponsorship of the United Nations Environment Programme, the International Labour Organisation and the World Health Organization. Available from, as of August 1, 2008: https://www.inchem.org/documents/ehc/ehc/ehc216.htm

7.4 Mechanism of Action

The mechanisms associated with the carcinogenic effects of HAAs include those identified for DCA and TCA. It is apparent that more than one mechanism is responsible for the effects of this class and that the importance of these mechanisms to the activity of individual members of the class varies. In part, these differences in mechanism can be related to the differences in tumor phenotypes that are induced. One phenotype seems to be associated with prior characterizations of tumors induced by peroxisome proliferators and is induced by TCA. The second phenotype involves glycogen-poor tumors that stain heavily with antibodies to c-Jun and c-Fos. This phenotype is produced by DCA. These effects are probably produced by selection of lesions with differing defects in cell signalling pathways that control the processes of cell division and cell death.
Environmental Health Criteria 216: Disinfectants and DIsinfectant By-Products (1999) by the International Programme on Chemical Safety (IPCS) under the joint sponsorship of the United Nations Environment Programme, the International Labour Organisation and the World Health Organization. Available from, as of August 1, 2008: https://www.inchem.org/documents/ehc/ehc/ehc216.htm
The brominated HAAs are about 10-fold more potent than their chlorinated analogues in their ability to induce point mutations. This does not establish that they are inducing cancer by mutagenic mechanisms in vivo, but this activity will have to be taken into account as data on their carcinogenic activity become more complete.
Environmental Health Criteria 216: Disinfectants and DIsinfectant By-Products (1999) by the International Programme on Chemical Safety (IPCS) under the joint sponsorship of the United Nations Environment Programme, the International Labour Organisation and the World Health Organization. Available from, as of August 1, 2008: https://www.inchem.org/documents/ehc/ehc/ehc216.htm
The HAAs vary widely in their ability to induce oxidative stress and to elevate the 8-OH-dG content of nuclear DNA of the liver. This property becomes increasingly apparent with the brominated compounds. It is notable that the brominated analogues are not more potent inducers of hepatic tumors than the corresponding chlorinated HAAs. Therefore, it is doubtful that this mechanism is the most important determinant of this effect.
Environmental Health Criteria 216: Disinfectants and DIsinfectant By-Products (1999) by the International Programme on Chemical Safety (IPCS) under the joint sponsorship of the United Nations Environment Programme, the International Labour Organisation and the World Health Organization. Available from, as of August 1, 2008: https://www.inchem.org/documents/ehc/ehc/ehc216.htm

8 Use and Manufacturing

8.1 General Manufacturing Information

Haloacetic acids ... are chemical byproducts of chlorination and chloramination of drinking water. /Haloacetates/
Cowman GA, Singer PC; Environ Sci Technol 30: 16-24 (1996)

9 Safety and Hazards

9.1 Hazards Identification

9.1.1 GHS Classification

1 of 2
View All
Pictogram(s)
Corrosive
Irritant
Signal
Danger
GHS Hazard Statements

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

H312 (100%): Harmful in contact with skin [Warning Acute toxicity, dermal]

H314 (100%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]

H318 (92.7%): Causes serious eye damage [Danger Serious eye damage/eye irritation]

H332 (100%): Harmful if inhaled [Warning Acute toxicity, inhalation]

Precautionary Statement Codes

P260, P261, P264, P264+P265, P270, P271, P280, P301+P317, P301+P330+P331, P302+P352, P302+P361+P354, P304+P340, P305+P354+P338, P316, P317, P321, P330, P362+P364, P363, 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 41 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.

9.1.2 Hazard Classes and Categories

Acute Tox. 4 (100%)

Acute Tox. 4 (100%)

Skin Corr. 1B (100%)

Eye Dam. 1 (92.7%)

Acute Tox. 4 (100%)

Carcinogenicity - Category 1B

Specific target organ toxicity - Repeated exposure - Category 2 (liver, genetic organs (men), hematopoietic system)

9.2 Fire Fighting

9.2.1 Fire Fighting Procedures

FIREFIGHTING: Protective Equipment: Wear self-contained breathing apparatus and protective clothing to prevent contact with skin and eyes.
Sigma-Aldrich; Material Safety Data Sheet for Bromodichloroacetic Acid, 100mg, neat (PN: 442499) 5 pp. (September 5, 2002) Available from, as of July 31, 2008: https://www.sigmaaldrich.com/catalog/search/ProductDetail/SUPELCO/442499
EXTINGUISHING MEDIA: Suitable: Carbon dioxide, dry chemical powder, or appropriate foam.
Sigma-Aldrich; Material Safety Data Sheet for Bromodichloroacetic Acid, 100mg, neat (PN: 442499) 5 pp. (September 5, 2002) Available from, as of July 31, 2008: https://www.sigmaaldrich.com/catalog/search/ProductDetail/SUPELCO/442499

9.2.2 Firefighting Hazards

Emits toxic fumes under fire conditions.
Sigma-Aldrich; Material Safety Data Sheet for Bromodichloroacetic Acid, 100mg, neat (PN: 442499) 5 pp. (September 5, 2002) Available from, as of July 31, 2008: https://www.sigmaaldrich.com/catalog/search/ProductDetail/SUPELCO/442499

9.3 Accidental Release Measures

9.3.1 Cleanup Methods

Cover with dry lime or soda ash, pick up, keep in a closed container, and hold for waste disposal. Ventilate area and wash spill site after material pickup is complete.
Sigma-Aldrich; Material Safety Data Sheet for Bromodichloroacetic Acid, 100mg, neat (PN: 442499) 5 pp. (September 5, 2002) Available from, as of July 31, 2008: https://www.sigmaaldrich.com/catalog/search/ProductDetail/SUPELCO/442499

9.3.2 Disposal Methods

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.
Dissolve or mix the material with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber. Observe all federal, state, and local environmental regulations.
Sigma-Aldrich; Material Safety Data Sheet for Bromodichloroacetic Acid, 100mg, neat (PN: 442499) 5 pp. (September 5, 2002) Available from, as of July 31, 2008: https://www.sigmaaldrich.com/catalog/search/ProductDetail/SUPELCO/442499

9.3.3 Preventive Measures

Do not breathe dust. Do not get in eyes, on skin, on clothing. Avoid prolonged or repeated exposure.
Sigma-Aldrich; Material Safety Data Sheet for Bromodichloroacetic Acid, 100mg, neat (PN: 442499) 5 pp. (September 5, 2002) Available from, as of July 31, 2008: https://www.sigmaaldrich.com/catalog/search/ProductDetail/SUPELCO/442499
Wear self-contained breathing apparatus, rubber boots, and heavy rubber gloves. Evacuate area in case of spill.
Sigma-Aldrich; Material Safety Data Sheet for Bromodichloroacetic Acid, 100mg, neat (PN: 442499) 5 pp. (September 5, 2002) Available from, as of July 31, 2008: https://www.sigmaaldrich.com/catalog/search/ProductDetail/SUPELCO/442499
Wash thoroughly after handling. Wash contaminated clothing before reuse. Discard contaminated shoes.
Sigma-Aldrich; Material Safety Data Sheet for Bromodichloroacetic Acid, 100mg, neat (PN: 442499) 5 pp. (September 5, 2002) Available from, as of July 31, 2008: https://www.sigmaaldrich.com/catalog/search/ProductDetail/SUPELCO/442499
SRP: Contaminated protective clothing should be segregated in such a manner so that there is no direct personal contact by personnel who handle, dispose, or clean the clothing. Quality assurance to ascertain the completeness of the cleaning procedures should be implemented before the decontaminated protective clothing is returned for reuse by the workers. Contaminated clothing should not be taken home at end of shift, but should remain at employee's place of work for cleaning.
For more Preventive Measures (Complete) data for BROMODICHLOROACETIC ACID (7 total), please visit the HSDB record page.

9.4 Handling and Storage

9.4.1 Storage Conditions

Keep tightly closed. Store in a cool dry place.
Sigma-Aldrich; Material Safety Data Sheet for Bromodichloroacetic Acid, 100mg, neat (PN: 442499) 5 pp. (September 5, 2002) Available from, as of July 31, 2008: https://www.sigmaaldrich.com/catalog/search/ProductDetail/SUPELCO/442499

9.5 Exposure Control and Personal Protection

9.5.1 Personal Protective Equipment (PPE)

ENGINEERING CONTROLS. Safety shower and eye bath. Use only in a chemical fume hood.
Sigma-Aldrich; Material Safety Data Sheet for Bromodichloroacetic Acid, 100mg, neat (PN: 442499) 5 pp. (September 5, 2002) Available from, as of July 31, 2008: https://www.sigmaaldrich.com/catalog/search/ProductDetail/SUPELCO/442499
PERSONAL PROTECTIVE EQUIPMENT Other: Wear appropriate government approved respirator, chemical-resistant gloves, safety goggles, other protective clothing. Faceshield (8-inch minimum).
Sigma-Aldrich; Material Safety Data Sheet for Bromodichloroacetic Acid, 100mg, neat (PN: 442499) 5 pp. (September 5, 2002) Available from, as of July 31, 2008: https://www.sigmaaldrich.com/catalog/search/ProductDetail/SUPELCO/442499
Faceshield (8-inch minimum).
Sigma-Aldrich; Material Safety Data Sheet for Bromodichloroacetic Acid, 100mg, neat (PN: 442499) 5 pp. (September 5, 2002) Available from, as of July 31, 2008: https://www.sigmaaldrich.com/catalog/search/ProductDetail/SUPELCO/442499

9.6 Regulatory Information

California Safe Cosmetics Program (CSCP) Reportable Ingredient

Hazard Traits - Carcinogenicity

Authoritative List - Prop 65

Report - regardless of intended function of ingredient in the product

10 Toxicity

10.1 Toxicological Information

10.1.1 Carcinogen Classification

NTP Technical Report
TR-583: Toxicology Studies of Bromodichloroacetic Acid (CASRN 71133-14-7) in F344/N Rats and B6C3F1/N Mice and Toxicology and Carcinogenesis Studies of Bromodichloroacetic Acid in F344/NTac Rats and B6C3F1/N Mice (Drinking Water Studies) (2015 )
Peer Review Date
Conclusion for Male Rat
Clear Evidence Clear Evidence
Conclusion for Female Rat
Clear Evidence Clear Evidence
Conclusion for Male Mice
Clear Evidence Clear Evidence
Conclusion for Female Mice
Clear Evidence Clear Evidence
Summary

Under the conditions of these 2-year studies, there was clear evidence of carcinogenic activity (see a summary of the Peer Review Panel comments and the public discussion on this Technical Report in Appendix P) of bromodichloroacetic acid in male F344/NTac rats based on increased incidences of malignant mesothelioma and the combined incidences of epithelial tumors of the skin. Occurrences of subcutaneous fibromas were also related to exposure to bromodichloroacetic acid. Occurrences of glioma or oligodendroglioma (combined) of the brain, squamous cell papilloma and squamous cell carcinoma of the oral cavity (oral mucosa or tongue), adenoma of the large intestine, and fibroadenoma of the mammary gland may have been related to exposure to bromodichloroacetic acid. There was clear evidence of carcinogenic activity of bromodichloroacetic acid in female F344/NTac rats based on increased incidences of fibroadenoma and carcinoma of the mammary gland. The occurrences of glioma or oligodendroglioma (combined) of the brain may have been related to bromodichloroacetic acid exposure. There was clear evidence of carcinogenic activity of bromodichloroacetic acid in male B6C3F1/N mice based on increased incidences of hepatocellular carcinoma and hepatoblastoma and increased incidences of adenoma or carcinoma (combined) of the Harderian gland. There was clear evidence of carcinogenic activity of bromodichloroacetic acid in female B6C3F1/N mice based on increased incidences of hepatocellular adenoma, hepatocellular carcinoma, and hepatoblastoma.

Exposure to bromodichloroacetic acid for 2 years resulted in increased incidences of nonneoplastic lesions in the bone marrow and liver of male and female rats, spleen of female rats, liver of male and female mice, and testis and epididymis of male mice.

10.1.2 Interactions

... When administered to rodents, haloacetates have been shown to increase formation of thiobarbituric acid-reactive substances and 8-hydroxydeoxyguanosine levels in the liver. These responses appear to be modified by prior treatment. To examine potential mechanisms that account for these modifications in oxidative stress, the ability of trichloroacetate (TCA) or dichloroacetate (DCA) pretreatment to alter the metabolism of bromodichloroacetate (BDCA) and the disposition of its metabolites was examined in male B6C3F1 mice. Two-week pretreatment with 1 g/L DCA and TCA in the drinking water of mice alters the initial hepatic metabolism of BDCA and the further metabolism of its metabolite DCA. DCA pretreatment inhibits cytosolic metabolism of both 1 mM DCA or BDCA up to 70%. In contrast, DCA pretreatment stimulates hepatic microsomal BDCA metabolism 1.3-fold but has little effect on microsomal metabolism of DCA. Increased microsomal metabolism of BDCA appears to be attributable to the induction of a metabolic pathway that produces CO2 and bromodichloromethane (BDCM) as metabolites. TCA pretreatment inhibits BDCA metabolism up to 70% in the cytosol and 30% in microsomes but has little effect on DCA metabolism. These results indicate that the hepatic metabolism of the haloacetate becomes quite complex at the high doses that have been employed in cancer bioassays...
Austin EW, Bull RJ; J Toxicol Environ Health 52 (4): 367-83 (1997)

10.1.3 Human Toxicity Excerpts

/SIGNS AND SYMPTOMS/ Corrosive. Causes burns. Harmful by inhalation, in contact with skin and if swallowed.
Sigma-Aldrich; Material Safety Data Sheet for Bromodichloroacetic Acid, 100mg, neat (PN: 442499) 5 pp. (September 5, 2002) Available from, as of July 31, 2008: https://www.sigmaaldrich.com/catalog/search/ProductDetail/SUPELCO/442499
/SIGNS AND SYMPTOMS/ ... Symptoms of exposure may include burning sensation, coughing, wheezing, laryngitis, shortness of breath, headache, nausea, and vomiting. Inhalation may result in spasm, inflammation and edema of the larynxand bronchi, chemical pneumonitis, and pulmonary edema. Material is extremely destructive to tissue of the mucous membranes and upper respiratory tract, eyes, and skin.
Sigma-Aldrich; Material Safety Data Sheet for Bromodichloroacetic Acid, 100mg, neat (PN: 442499) 5 pp. (September 5, 2002) Available from, as of July 31, 2008: https://www.sigmaaldrich.com/catalog/search/ProductDetail/SUPELCO/442499
/EPIDEMIOLOGY STUDIES/ Chlorination of drinking water generates disinfection by-products (DBPs) , which have been shown to disrupt spermatogenesis in rodents at high doses, suggesting that DBPs could pose a reproductive risk to men. ...This study ...assessed DBP exposure and testicular toxicity, as evidenced by altered semen quality. ... A cohort study /was conducted/ to evaluate semen quality in men with well-characterized exposures to DBPs. Participants were 228 presumed fertile men with different DBP profiles. They completed a telephone interview about demographics, health history, water consumption, and other exposures and provided a semen sample. Semen outcomes included sperm concentration and morphology, as well as DNA integrity and chromatin maturity. Exposures to DBPs were evaluated by incorporating data on water consumption and bathing and showering with concentrations measured in tap water. ... Multivariable linear regression /was used/ to assess the relationship between exposure to DBPs and adverse sperm outcomes. ... The mean (median) sperm concentration and sperm count were 114.2 (90.5) million/mL and 362 (265) million, respectively. The mean (median) of the four trihalomethane species (THM4) exposure was 45.7 (65.3) ug/L, and the mean (median) of the nine haloacetic acid species (HAA9) exposure was 30.7 (44.2) ug/L. These sperm parameters were not associated with exposure to these classes of DBPs. For other sperm outcomes, we found no consistent pattern of increased abnormal semen quality with elevated exposure to trihalomethanes (THMs) or haloacetic acids (HAAs) . The use of alternate methods for assessing exposure to DBPs and site-specific analyses did not change these results. ... Overall, the results of the present study do not support an association between exposure to DBPs at levels approaching regulatory limits and adverse sperm outcomes, although /there was/ an association between total organohalides and sperm concentration that was in line with /the/ hypothesis.... The lone association of total organohalide exposure with sperm concentration may lend support to findings that have suggested that total organohalide is a stronger risk factor for adverse pregnancy outcomes than any of the regulated DBP groups or species...that the toxicity of total organohalides is greater than that of the individual or subclasses of DBPs. ... Previous studies have suggested that exposures to THMs via bathing and showering may be more strongly associated with adverse reproductive outcomes than other exposure indicators ... . /These/ results did not support these findings. /Disinfection by-products/
Luben TJ et al; Env Health Persp 115 (8): 2007. Full paper Available from, as of July 31, 2008: https://www.ehponline.org/members/2007/10120/10120.html#intro

10.1.4 Non-Human Toxicity Excerpts

/LABORATORY ANIMALS: Developmental or Reproductive Toxicity/ ... The effects of exposing neurulation staged (3-6 somite pairs) CD-1 mouse conceptuses to bromochloro- (BCA), dibromochloro- (DBCA) and bromodichloro-acetic (BDCA) acids in whole embryo culture /were examined/ at concentrations ranging from 50 to 2500 uM. Morphological development was assessed after a 26 hr exposure period. Exposure of conceptuses to these HAAs produced dysmorphogenesis, including prosencephalic and pharyngeal arch hypoplasia as well as eye and heart tube abnormalities. Benchmark concentrations for induction of neural tube dysmorphogenesis were 63, 500 and 536 uM for BCA, DBCA and BDCA, respectively. /A/ previously developed HAA QSAR accurately predicted placement of these three chemicals in the larger context of the previously tested di- and tri-HAAs, also correctly predicting that BCA would be more potent than DBCA and BDCA, and that the latter two HAAs would be near equi-potent...
Hunter ES 3rd; Reprod Toxicol 21 (3): 260-6 (2006)
/GENOTOXICITY/ Micronucleus (peripheral blood): B6C3F1 Mice (male and female) dosed for 13 wks, polychromatic erythrocytes scored in 10 animals per sex 24 hr after last dose - negative. Salmonella TA97, TA98, TA100, TA1535 w/wo rat and hamster S-9 (5-30%)- weakly positive.
NTP/NIEHS; Bromodichloroacetic acid micronucleus study summary. Available from, as of July 31, 2008: https://ntp-apps.niehs.nih.gov/ntp_tox/index.cfm?fuseaction=ntpsearch.searchresults&searchterm=71133-14-7

10.1.5 Ongoing Test Status

The following link will take the user to the National Toxicology Program (NTP) Test Agent Search Results page, which tabulates all of the "Standard Toxicology & Carcinogenesis Studies", "Developmental Studies", and "Genetic Toxicity Studies" performed with this chemical. Clicking on the "Testing Status" link will take the user to the status (i.e., in review, in progress, in preparation, on test, completed, etc.) and results of all the studies that the NTP has done on this chemical. [http://ntp-apps.niehs.nih.gov/ntp_tox/index.cfm?fuseaction=ntpsearch.searchresults&searchterm=71133-14-7]

10.2 Ecological Information

10.2.1 EPA Ecotoxicity

Pesticide Ecotoxicity Data from EPA

10.2.2 Artificial Pollution Sources

Studies suggest that bromochloro haloacetic acid species are formed from the chlorination of water containing aquatic humic substances in the presence of bromide ion(1). At high bromide concentrations in the range of 6-15 uM bromide ion, bromodichloroacetic acid was the principal species formed when using model water prepared from extracted aqautic humic substances(1).
(1) Cowman GA, Singer PC; Environ Sci Technol 30: 16-24 (1996)

10.2.3 Environmental Water Concentrations

DRINKING WATER: Bromodichloroacetic acid levels in finished drinking water samples from the Philadelphia, PA Suburban Water Co., Houston, TX, Metropolitan Water District of Southern California and Corpus Christi, TX were 6.55, 5.28, 12.2 and 8.75 ug/L, respectively(1).
(1) Cowman GA, Singer PC; Environ Sci Technol 30: 16-24 (1996)

11 Literature

11.1 Consolidated References

11.2 NLM Curated PubMed Citations

11.3 Springer Nature References

11.4 Chemical Co-Occurrences in Literature

11.5 Chemical-Gene Co-Occurrences in Literature

11.6 Chemical-Disease Co-Occurrences in Literature

12 Patents

12.1 Depositor-Supplied Patent Identifiers

12.2 WIPO PATENTSCOPE

12.3 Chemical Co-Occurrences in Patents

12.4 Chemical-Disease Co-Occurrences in Patents

13 Interactions and Pathways

13.1 Chemical-Target Interactions

14 Biological Test Results

14.1 BioAssay Results

15 Classification

15.1 MeSH Tree

15.2 ChemIDplus

15.3 UN GHS Classification

15.4 NORMAN Suspect List Exchange Classification

15.5 EPA DSSTox Classification

15.6 EPA Substance Registry Services Tree

15.7 MolGenie Organic Chemistry Ontology

16 Information Sources

  1. California Office of Environmental Health Hazard Assessment (OEHHA)
  2. California Safe Cosmetics Program (CSCP) Product Database
  3. 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/
  4. ChemIDplus
    ChemIDplus Chemical Information Classification
    https://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
  5. EPA DSSTox
    CompTox Chemicals Dashboard Chemical Lists
    https://comptox.epa.gov/dashboard/chemical-lists/
  6. 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
  7. 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
  8. Hazardous Substances Data Bank (HSDB)
  9. 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
  10. Drug Gene Interaction database (DGIdb)
    LICENSE
    The data used in DGIdb is all open access and where possible made available as raw data dumps in the downloads section.
    http://www.dgidb.org/downloads
  11. EPA Pesticide Ecotoxicity Database
  12. NITE-CMC
    Bromodichloroacetic acid - FY2016 (New/original classication)
    https://www.chem-info.nite.go.jp/chem/english/ghs/16-mhlw-0015e.html
  13. Japan Chemical Substance Dictionary (Nikkaji)
  14. NTP Technical Reports
    Bromodichloroacetic Acid
    https://ntp.niehs.nih.gov/data/tr
  15. Springer Nature
  16. Wikidata
  17. PubChem
  18. Medical Subject Headings (MeSH)
    LICENSE
    Works produced by the U.S. government are not subject to copyright protection in the United States. Any such works found on National Library of Medicine (NLM) Web sites may be freely used or reproduced without permission in the U.S.
    https://www.nlm.nih.gov/copyright.html
  19. GHS Classification (UNECE)
  20. 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/
  21. EPA Substance Registry Services
  22. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  23. PATENTSCOPE (WIPO)
CONTENTS