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115835

Sigma-Aldrich

2-Bromoacetophenone

98%

Synonym(s):

ω-Bromoacetophenone, Phenacyl bromide

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About This Item

Linear Formula:
C6H5COCH2Br
CAS Number:
70-11-1
Molecular Weight:
199.04
Beilstein:
606474
EC Number:
200-724-9
MDL number:
MFCD00000195
UNSPSC Code:
12352100
PubChem Substance ID:
24847241
NACRES:
NA.22
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Quality Level

100

Assay

98%

form

solid

bp

135 °C/18 mmHg (lit.)

mp

48-51 °C (lit.)

functional group

bromo
ketone
phenyl

SMILES string

BrCC(=O)c1ccccc1

InChI

1S/C8H7BrO/c9-6-8(10)7-4-2-1-3-5-7/h1-5H,6H2

InChI key

LIGACIXOYTUXAW-UHFFFAOYSA-N

Gene Information

human ... PTPN6(5777)

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Application

2-Bromoacetophenone has been used in the analysis of organic acids involving the formation of phenacyl derivatives[1].

Pictograms

Corrosion
GHS05

Signal Word

Danger

Hazard Statements

H314

Hazard Classifications

Skin Corr. 1B

Storage Class Code

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic 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
0000420370
0000420370
0000342364
0000342364
0000297183

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J G Streeter
Plant physiology, 85(3), 768-773 (1987-11-01)
Metabolites in Bradyrhizobium japonicum bacteroids and in Glycine max (L.) Merr. cytosol from root nodules were analyzed using an isolation technique which makes it possible to estimate and correct for changes in concentration which may occur during bacteroid isolation. Bacteroid
S Ramalingam et al.
Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy, 78(2), 826-834 (2011-01-11)
In this work, the experimental and theoretical spectra of 4-chloro-2-bromoacetophenone (4C2BAP) are studied. FT-IR and FT-Raman spectra of title molecule have been recorded in the region 4000-100 cm(-1). The structural and spectroscopic data of the molecule in the ground state
A Kanstrup et al.
Archives of biochemistry and biophysics, 304(2), 332-337 (1993-08-01)
A series of 18 phenacyl bromide and iodoacetamide analogues have been synthesized and used to alkylate Met-398 situated in the S'1 binding site of carboxypeptidase Y. The course of the reactions was monitored by measurements of the peptidase and esterase
P A Wender et al.
Organic letters, 1(13), 2117-2120 (2000-06-03)
[formula: see text] 4'-Bromoacetophenone derivatives which upon excitation can generate monophenyl radicals capable of hydrogen atom abstraction were investigated as photoinducible DNA cleaving agents. Pyrrolecarboxamide-conjugated 4'-bromoacetophenones were synthesized, and their DNA cleaving activities and sequence selectivities were determined.
Anabha E Raveendran et al.
Organic & biomolecular chemistry, 8(4), 901-905 (2010-02-06)
Nucleophilic heterocyclic carbenes (NHCs) have been used for the first time as catalysts in the cyclopropanation of ethyl cyanocinnamates with phenacyl bromide by Michael-initiated ring-closure (MIRC).
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Questions

1–4 of 4 Questions  

  1. 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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  2. 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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  3. What is the Department of Transportation shipping information for this product?

    1 answer

    1. Transportation information can be found in Section 14 of the product's (M)SDS.To access the shipping information for this material, use the link on the product detail page for the product.

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  4. Do you have references on the use of 2-Bromoacetophenone (also known as phenacyl bromide) Products 115835 and 77450 for making phenacyl esters of carboxylic acids for HPLC analysis?

    1 answer

    1. For information on the use of phenacyl bromide to derivatize carboxylic acids (e.g., fatty acids) for HPLC analysis, please see one or more of the following three references:1. K.J. Longmuir, et al., Determination of monoenoic fatty acid double bond position by permanganate-periodate oxidation followed by high-performance liquid chromatography of carboxylic acid phenacyl esters. Analytical Biochemistry, 167(2), 213-221 (1987). 2. T. Hanis et al.,  Determination of fatty acids as phenacyl esters in rat adipose tissue and blood vessel walls by high-performance liquid chromatography. Journal of Chromatography, 452, 443-457 (1988).3. A. Mehta et al., Rapid quantitation of free fatty acids in human plasma by high-performance liquid chromatography. Journal of Chromatography B Biomedical Science Applications, 719(1-2), 9-23 (1998).

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