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249785

Sigma-Aldrich

2-Bromopropionyl bromide

97%

Synonym(s):

α-Bromopropanyl bromide, α-Bromopropionyl bromide, (±)-2-Bromopropanoyl bromide, 2-Bromopropanoyl bromide

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About This Item

Linear Formula:
CH3CHBrCOBr
CAS Number:
563-76-8
Molecular Weight:
215.87
Beilstein:
1071331
EC Number:
209-261-7
MDL number:
MFCD00000142
UNSPSC Code:
12352100
PubChem Substance ID:
24855014
NACRES:
NA.22
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vapor density

7.5 (vs air)

Quality Level

200

vapor pressure

1.3 mmHg ( 20 °C)

Assay

97%

form

liquid

refractive index

n20/D 1.518 (lit.)

bp

48-50 °C/10 mmHg (lit.)

density

2.061 g/mL at 25 °C (lit.)

functional group

acyl bromide
bromo

SMILES string

CC(Br)C(Br)=O

InChI

1S/C3H4Br2O/c1-2(4)3(5)6/h2H,1H3

InChI key

ILLHORFDXDLILE-UHFFFAOYSA-N

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Application

2-Bromopropionyl bromide has been used in the synthesis of:
  • cellulose macroinitiator via direct acylation of cellulose in ionic liquid 1-allyl-3-methylimidazolium chloride[1]
  • 3-(2-bromopropionyl)-2-oxazolidone derivatives[2]
  • bromoester terminated poly(3-hexylthiophene), used as macroinitiator for atom transfer radical polymerization of acrylates[3].

Pictograms

CorrosionExclamation mark
GHS05,GHS07

Signal Word

Danger

Hazard Statements

H302,H314

Hazard Classifications

Acute Tox. 4 Oral - Skin Corr. 1B

Storage Class Code

8A - Combustible corrosive hazardous materials

WGK

WGK 3

Flash Point(F)

235.4 °F - closed cup

Flash Point(C)

113 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCCL2129
BCCG2369
BCCC6465
BCBM5756V
BCBK1279V

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A highly stereoselective synthesis of a key intermediate of 1?-methylcarbapenems employing the reformatsky reaction of 3-(2-bromopropionyl)-2-oxazolidone derivatives.
Ito Y and Terashima S.
Tetrahedron Letters, 28(52), 6625-6628 (1987)
Xiaofeng Sui et al.
Biomacromolecules, 9(10), 2615-2620 (2008-09-09)
Cellulose-graft-poly(N,N-dimethylamino-2-ethyl methacrylate) (cellulose-g-PDMAEMA) copolymers were prepared by homogeneous atom transfer radical polymerization (ATRP) under mild conditions. Cellulose macroinitiator was successfully synthesized by direct acylation of cellulose with 2-bromopropionyl bromide in a room temperature ionic liquid (RTIL), 1-allyl-3-methylimidazolium chloride. Copolymers were
Regioregular poly (3-alkylthiophene) conducting block copolymers.
Iovu MC, et al.
Polymer, 46(19), 8582-8586 (2005)
Yanfei Hu et al.
International journal of pharmaceutics, 491(1-2), 152-161 (2015-06-23)
Thermo-responsive brush-like amphiphilic poly[2-(2-methoxyethoxy) ethyl methacrylate-co-oligo(ethylene glycol) methacrylate]-b-poly(l-lactide)-b-poly[2-(2-methoxyethoxy) ethyl methacrylate-co-oligo(ethylene glycol) methacrylate] [P(MEO2MA-co-OEGMA)-b-PLLA-b-P(MEO2MA-co-OEGMA)] triblock copolymers were synthesized by atom transfer radical polymerization of MEO2MA and OEGMA co-monomers using a α,ω-Bromopropionyl poly(l-lactide) (Br-PLLA-Br) macroinitiator. The resulting copolymers with MEO2MA/OEGMA molar ratio

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