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B56412

Sigma-Aldrich

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
Beilstein:
605440
EC Number:
209-923-5
MDL number:
MFCD00000115
UNSPSC Code:
12352100
PubChem Substance ID:
24891846
NACRES:
NA.22

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

SMILES string

BrCC(Br)=O

InChI

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

InChI key

LSTRKXWIZZZYAS-UHFFFAOYSA-N

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General description

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

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.

Pictograms

Corrosion
GHS05

Signal Word

Danger

Hazard Statements

H314

Hazard Classifications

Skin Corr. 1B

Supplementary Hazards

EUH014

Storage Class Code

8A - Combustible corrosive hazardous materials

WGK

WGK 3

Flash Point(F)

221.0 °F - closed cup

Flash Point(C)

105 °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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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)
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)
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)
Site-Selective Conversion of Azido Groups at Carbonyl ?-Positions to Diazo Groups in Diazido and Triazido Compounds.
Yokoi T, et al.
The Journal of Organic Chemistry, 83(19), 12103-12121 (2018)
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