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B65586

Sigma-Aldrich

2-Bromoethanol

95%

Synonym(s):

Ethylene bromohydrin

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About This Item

Linear Formula:
BrCH2CH2OH
CAS Number:
540-51-2
Molecular Weight:
124.96
Beilstein:
878140
EC Number:
208-748-1
MDL number:
MFCD00002827
UNSPSC Code:
12352100
PubChem Substance ID:
24891919
NACRES:
NA.22

vapor density

4.3 (vs air)

vapor pressure

2.4 mmHg ( 20 °C)

Assay

95%

form

liquid

refractive index

n20/D 1.492 (lit.)

bp

56-57 °C/20 mmHg (lit.)

density

1.763 g/mL at 25 °C (lit.)

storage temp.

2-8°C

SMILES string

OCCBr

InChI

1S/C2H5BrO/c3-1-2-4/h4H,1-2H2

InChI key

LDLCZOVUSADOIV-UHFFFAOYSA-N

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Application

2-Bromoethanol can be used for the preparation of 2-bromoethyl glycosides from acetylated sugars. It can also be used as a starting material to synthesize 2-bromoethyl methoxymethyl ether.
2-Bromoethanol is used in selective reduction of nitroarenes (PcFe(II)/NaBH4/2-bromoethanol catalyst system).

Pictograms

Skull and crossbonesCorrosion
GHS06,GHS05

Signal Word

Danger

Hazard Statements

H301 + H311 + H331,H314

Hazard Classifications

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

Storage Class Code

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

WGK

WGK 3

Flash Point(F)

230.0 °F - closed cup

Flash Point(C)

110 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Regio?and Stereoselective Intramolecular Hydrosilylation of α?Hydroxy Enol Ethers: 2, 3?syn?2?Methoxymethoxy?1, 3?Nonanediol: 1, 3?Nonanediol, 2?(methoxymethoxy)?,(R, R)?(?)?.
Tamao K, et al.
Organic Syntheses, 73, 94-94 (2003)
2-Bromoethyl glycosides: synthesis and characterisation.
Dahmen J, et al.
Carbohydrate Research, 116(2), 303-307 (1983)
A R Jones et al.
Xenobiotica; the fate of foreign compounds in biological systems, 11(11), 763-770 (1981-11-01)
1. The metabolism of 2-bromo[U-14C]ethanol an [U-14C]ethylene oxide has been studied in the rat. 2. As both compounds give rise to similar amounts of two urinary metabolites, identified as S-(2-hydroxyethyl)cysteine and N-acetyl-S-(2-hydroxyethyl)cysteine, it is proposed that 2-bromoethanol is converted into
S Khan et al.
Pharmacology & toxicology, 78(4), 241-248 (1996-04-01)
The cytotoxicity of 2-bromoethanol towards hepatocytes isolated from rats was concentration-dependent (EC(50)100 mu M, 2 hr). Bromoacetaldehyde was more toxic (EC(50)60 mu M, 2 hr) and bromoacetic acid was less toxic (EC(50)150 mu M, 2 hr). Glutathione (GSH) depletion occurred
S Khan et al.
Biochemical pharmacology, 45(2), 439-447 (1993-01-26)
The cytotoxicity of dibromoalkanes to isolated hepatocytes was proportional to the dibromoalkane concentration and increasing chain length of the dibromoalkane (C2-C6). The rapid hepatocyte glutathione (GSH) depletion which occurred upon addition of the dibromoalkanes was also dependent on the concentration
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