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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:
Molecular Weight:
201.84
Beilstein:
605440
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22
Pricing and availability is not currently available.

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.[1]

Application

Bromoacetyl bromide can be used to convert:
  • Amines to azido acetamides.[2]
  • 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]
  • 3,5-Dimethylphenol to 3,5-dimethylphenyl 2-bromoacetate.[4]
  • Cystamine dihydrochloride to N,N′-bis(bromoacetyl) cystamine, a bifunctional quaternizing agent.[5]

It can also be used as a reagent to synthesize imidazolium or piridinium based ionic liquids.[6]

Pictograms

Corrosion

Signal Word

Danger

Hazard Statements

Hazard Classifications

Skin Corr. 1B

Supplementary Hazards

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

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Certificates of Analysis (COA)

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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)
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)
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)
Regio-and Stereoselective Nickel-Catalyzed Coupling of Boronic Acids with Allenoates.
Liu Y, et al.
Synthesis, 29(2), 546-558 (2018)

Questions

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  1. How can I determine the shelf life / expiration / retest date of this product?

    1 answer
    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer
    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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