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Merck
CN

B56412

Bromoacetyl bromide

≥98%

Synonym(s):

α-Bromoacetyl bromide, 2-Bromoacetyl bromide, Monobromoacetyl bromide

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About This Item

Linear Formula:
BrCH2COBr
CAS Number:
598-21-0
Molecular Weight:
201.84
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
24891846
EC Number:
209-923-5
Beilstein/REAXYS Number:
605440
MDL number:
MFCD00000115

Key Documents

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Product Name

Bromoacetyl bromide, ≥98%

InChI key

LSTRKXWIZZZYAS-UHFFFAOYSA-N

InChI

1S/C2H2Br2O/c3-1-2(4)5/h1H2

SMILES string

BrCC(Br)=O

vapor pressure

3.8 mmHg ( 25 °C)

assay

≥98%

form

liquid

refractive index

n20/D 1.547 (lit.)

bp

147-150 °C (lit.)

density

2.317 g/mL at 25 °C (lit.)

storage temp.

2-8°C

Quality Level

200

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Application

Bromoacetyl bromide can be used to convert:
  • Amines to azido acetamides.
  • p-Arsanilic acid to 4-(2-bromoacetylamino)benzenearsonic acid, a precursor to 4-(N-(S-penicillaminylacetyl)amino)phenylarsonous acid (PENAO), a metal-based drug.
  • 3,5-Dimethylphenol to 3,5-dimethylphenyl 2-bromoacetate.
  • Cystamine dihydrochloride to N,N′-bis(bromoacetyl) cystamine, a bifunctional quaternizing agent.

It can also be used as a reagent to synthesize imidazolium or piridinium based ionic liquids.

General description

Bromoacetyl bromide is employed as an acylating reagent and in the production of heterocyclic compounds.

pictograms

Corrosion
GHS05

signalword

Danger

hcodes

H314

Hazard Classifications

Skin Corr. 1B

supp_hazards

EUH014

Storage Class

8A - Combustible corrosive hazardous materials

wgk

WGK 3

flash_point_f

221.0 °F - closed cup

flash_point_c

105 °C - closed cup

ppe

Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter

Regulatory Information

危险化学品
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Certificates of Analysis (COA)

Lot/Batch Number
MKCQ3399
SHBK0532
SHBF8313V
SHBD3386V
58496PMV

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Bromoacetyl Bromide
Mantri AV
Synlett, 23, 2144-2145 (2012)
pH and reduction dual-responsive nanogel cross-linked by quaternization reaction for enhanced cellular internalization and intracellular drug delivery.
Li M, et al.
Polym. Chem., 4(4), 1199-1207 (2013)
Aggregation behavior and antimicrobial activity of ester-functionalized imidazolium-and pyridinium-based ionic liquids in aqueous solution.
Garcia MT, et al.
Langmuir, 29(8), 2536-2545 (2013)
Direct Polymerization of the Arsenic Drug PENAO to Obtain Nanoparticles with High Thiol-Reactivity and Anti-Cancer Efficiency.
Noy JM, et al.
Bioconjugate Chemistry, 29(2), 546-558 (2018)
Regio-and Stereoselective Nickel-Catalyzed Coupling of Boronic Acids with Allenoates.
Liu Y, et al.
Synthesis, 29(2), 546-558 (2018)
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