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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
Assay:
≥98%
Form:
liquid

Key Documents

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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

Quality Level

200

bp

147-150 °C (lit.)

density

2.317 g/mL at 25 °C (lit.)

storage temp.

2-8°C

Related Categories

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.

signalword

Danger

supp_hazards

EUH014

Storage Class

8A - Combustible corrosive hazardous materials

flash_point_f

221.0 °F - closed cup

flash_point_c

105 °C - closed cup

ppe

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

pictograms

CorrosionExclamation mark
GHS05,GHS07

Hazard Classifications

Acute Tox. 4 Oral - Eye Dam. 1 - Skin Corr. 1B - Skin Sens. 1

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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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)
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)
Bromoacetyl Bromide
Mantri AV
Synlett, 23, 2144-2145 (2012)
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)
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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