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245615

Sigma-Aldrich

2-Bromo-4′-nitroacetophenone

95%

Synonym(s):

ω-Bromo-4-nitroacetophenone, 4-Nitrophenacyl bromide

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About This Item

Linear Formula:
O2NC6H4COCH2Br
CAS Number:
99-81-0
Molecular Weight:
244.04
Beilstein:
393567
EC Number:
202-789-9
MDL number:
MFCD00007356
UNSPSC Code:
12352100
PubChem Substance ID:
24854745
NACRES:
NA.22

Assay

95%

mp

94-99 °C (lit.)

SMILES string

[O-][N+](=O)c1ccc(cc1)C(=O)CBr

InChI

1S/C8H6BrNO3/c9-5-8(11)6-1-3-7(4-2-6)10(12)13/h1-4H,5H2

InChI key

MBUPVGIGAMCMBT-UHFFFAOYSA-N

Gene Information

human ... PTPN6(5777)

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Application

2-Bromo-4′-nitroacetophenone was used to study the pKa of the histidine-34 imidazole.

Pictograms

Corrosion
GHS05

Signal Word

Danger

Hazard Statements

H314

Hazard Classifications

Skin Corr. 1B

Storage Class Code

8A - Combustible corrosive hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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R R Annand et al.
Biochemistry, 35(14), 4591-4601 (1996-04-09)
In bee venom phospholipase A2, histidine-34 probably functions as a Brønsted base to deprotonate the attacking water. Aspartate-64 and tyrosine-87 form a hydrogen bonding network with histidine-34. We have prepared mutants at these positions and studied their kinetic properties. The
B Z Yu et al.
Biochemistry, 36(13), 3870-3881 (1997-04-01)
Interfacial catalytic constants for bee venom phospholipase A2 (bvPLA2) have been obtained for its action on vesicles of the anionic phospholipid 1,2-dimyristoylphosphatidylmethanol (DMPM) in the highly processive scooting mode. Spectroscopic measurements which directly measure transbilayer movement of membrane components show
A Parkinson et al.
The Journal of biological chemistry, 261(25), 11478-11486 (1986-09-05)
The alkylating agent 2-bromo-4'-nitroacetophenone (BrNAP) binds covalently to each of 10 isozymes of purified rat liver microsomal cytochrome P-450 (P-450a-P-450j) but substantially inhibits the catalytic activity of only cytochrome P-450c. Regardless of pH, incubation time, presence of detergents, or concentration
Dana Ortansa Dorohoi et al.
Molecules (Basel, Switzerland), 26(13) (2021-07-03)
Two 4-tolyl-1,2,4-triazol-1-ium methylids, namely 4-tolyl-1,2,4-triazol-1-ium-phenacylid and 4-tolyl-1,2,4-triazol-1-ium-4'-nitro-phenacylid, are studied from solvatochromic point of view in binary solvent mixtures of water with ethanol and water with methanol. The contributions (expressed in percent) of the universal and specific interactions are separated from
A Parkinson et al.
The Journal of biological chemistry, 261(25), 11487-11495 (1986-09-05)
The mechanism by which 2-bromo-4'-nitroacetophenone (BrNAP) inactivates cytochrome P-450c, which involves alkylation primarily at Cys-292, is shown in the present study to involve an uncoupling of NADPH utilization and oxygen consumption from product formation. Alkylation of cytochrome P-450c with BrNAP
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