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242357

Sigma-Aldrich

Dibromoacetic acid

97%

Synonym(s):

2,2-Dibromoacetic acid, DBAA

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About This Item

Linear Formula:
Br2CHCOOH
CAS Number:
631-64-1
Molecular Weight:
217.84
Beilstein/REAXYS Number:
1700457
EC Number:
211-165-5
MDL number:
MFCD00004205
UNSPSC Code:
12352106
PubChem Substance ID:
24854553
NACRES:
NA.22

Quality Level

200

assay

97%

form

solid

bp

128-130 °C/16 mmHg (lit.)

mp

32-38 °C (lit.)

density

2.382 g/mL at 25 °C (lit.)

functional group

bromo
carboxylic acid

SMILES string

OC(=O)C(Br)Br

InChI

1S/C2H2Br2O2/c3-1(4)2(5)6/h1H,(H,5,6)

InChI key

SIEILFNCEFEENQ-UHFFFAOYSA-N

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Application

Dibromoacetic acid can be used as a reactant:
  • Forthe stereoselective synthesis of (E)-α, β-unsaturated carboxylic acidsby samarium diiodide (SmI2) catalyzed reaction with aldehydes.
  • Tosynthesize sodium bis(2-pyridylthio)acetate ligand by reacting with 2-mercaptopyridinein the presence of NaOH.

Other Notes

remainder mono-bromoacetic acid

pictograms

CorrosionExclamation mark
GHS05,GHS07

signalword

Danger

Hazard Classifications

Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Acute Tox. 4 Oral - Aquatic Chronic 3 - Eye Dam. 1 - Skin Corr. 1B

Storage Class

8A - Combustible corrosive hazardous materials

wgk_germany

WGK 3

flash_point_f

235.4 °F - closed cup

flash_point_c

113 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

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Certificates of Analysis (COA)

Lot/Batch Number
BCCK1310
BCBR5175V
1451954
1451954V
1436937

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Wenbo Jiang et al.
Metabolic brain disease, 32(6), 2009-2019 (2017-08-28)
Dibromoacetic acid (DBA) exsits in drinking water as a by-product of disinfection as a result of chlorination or ozonation processes. Hippocampus and pre-frontal cortex are the key structures in memory formation and weanling babies are more sensitive to environmental toxicant
Eric R V Dickenson et al.
Environmental science & technology, 42(9), 3226-3233 (2008-06-05)
While it is known that resorcinol- and phenol-type aromatic structures within natural organic matter (NOM) react during drinking water chlorination to form trihalomethanes (THMs), limited studies have examined aliphatic-type structures as THM and haloacetic acid (HAA) precursors. A suite of
K J Bodensteiner et al.
Toxicological sciences : an official journal of the Society of Toxicology, 80(1), 83-91 (2004-05-14)
To determine if dibromoacetic acid (DBA) affects ovarian folliculogenesis, four groups of female Dutch-belted rabbits were exposed daily to 0, 1, 5, or 50 mg DBA/kg body weight in drinking water beginning in utero from gestation day 15 throughout life.
Lianhui Tao et al.
Toxicological sciences : an official journal of the Society of Toxicology, 82(1), 62-69 (2004-09-03)
Dibromoacetic acid (DBA) is a drinking water disinfection by-product. Its analogs, dichloroacetic acid (DCA) and trichloroacetic acid (TCA), are liver carcinogens in rodents. We evaluated the ability of DBA to cause DNA hypomethylation, glycogen accumulation, and peroxisome proliferation that are
Gary R Klinefelter et al.
Toxicological sciences : an official journal of the Society of Toxicology, 81(2), 419-429 (2004-07-16)
Previously our work on the haloacid by-products of drinking water disinfection focused on adult exposures. Herein we evaluate the consequence of continuous exposure to dibromoacetic acid (DBA) via drinking water through reproductive development into adulthood. An initial study in which
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