CAS 99-73-0 4-Bromophenacyl bromide (HCID 7454)

Overview

phospholipidase A(2) inhibitor; structure

Names & identifiers

Preferred name: 4-Bromophenacyl bromide
IUPAC: 2-bromo-1-(4-bromophenyl)ethanone
English name: 2,4'-Dibromoacetophenone
Molecular formula: C8H6Br2O
Molecular weight: 277.94

Names & synonyms

2,4'-Dibromoacetophenone99-73-04-Bromophenacyl bromidep-Bromophenacyl bromideEthanone, 2-bromo-1-(4-bromophenyl)-bromophenacylbromideParabromophenacyl bromidePBPAB2,4-dibromoacetophenonealpha-para-dibromoacetophenonePN0FRW1G4ZDTXSID4059201

Show more names

PBPBp-bromophenacyl-8AKOS BBS-00000865GSK-3β Inhibitor VII

NSC-6224RefChem:858009DTXCID4049111202-783-6bromophenacyl bromide2-Bromo-1-(4-bromophenyl)ethanone2-bromo-1-(4-bromophenyl)ethan-1-one2-bromo-1-(4-bromophenyl)-ethanone

Database identifiers

CAS: 99-73-0
PubChem CID: 7454
DTXSID: DTXSID4059201
ChEMBL: CHEMBL142826
UNII: PN0FRW1G4Z
EC Number: 202-783-6
Nikkaji: J3.227A

Properties

Computed structural properties

XLogP: 3.2
Topological polar surface area: 17.1 Å²
Hydrogen bond donors: 0
Hydrogen bond acceptors: 1
Rotatable bonds: 2
Heavy atoms: 11
Formal charge: 0
Complexity: 139

Experimental & physicochemical properties

Chemical ClassesOther Classes -> Aromatic Ketones, Halogenated

SpringerMaterials PropertiesNuclear quadrupole resonance spectroscopy

Physical DescriptionSolid; [Merck Index] Off-white crystalline powder with a pungent odor; [Alfa Aesar MSDS]

Physicochemical properties

Melting point: 108 · 108-110 °C(lit.)
Boiling point: 1415 °C/760mm · 1415°C/760mm
Density: 1.7855 · 1.7855 (rough estimate)
refractive index: 1.556 · 1.5560 (estimate)
storage temp.: 30 °C · Store below +30°C.
solubility: 5 mg/ml; · DMF: 5 mg/ml; DMSO: 2 mg/ml; Ethanol: 1 mg/ml; PBS (pH 7.2): insol
form: Crystalline Solid
color: Slightly yellow to beige
Water Solubility: Soluble in dimethyl sulfoxide (5 mg/ml), methanol (20 mg/ml), toluene and ethanol. Insoluble in water.
Sensitive: Lachrymatory
Merck: 14 · 14,1427
BRN: 607604 · 607604
Stability: Stable. Incompatible with strong bases, strong reducing agents, strong oxidizing agents.
InChI: 1S/C8H6Br2O/c9-5-8(11)6-1-3-7(10)4-2-6/h1-4H,5H2
InChIKey: FKJSFKCZZIXQIP-UHFFFAOYSA-N
SMILES: BrCC(=O)c1ccc(Br)cc1
CAS DataBase Reference: 99 · 99-73-0(CAS DataBase Reference)
FDA UNII: 0 FRW1G4Z · PN0FRW1G4Z
EPA Substance Registry System: 2 · Ethanone, 2-bromo-1-(4-bromophenyl)- (99-73-0)
UNSPSC Code: 12352115 · 12352115
NACRES: 77 · NA.77
Symbol(GHS): 5 · GHS05
Signal word: Danger
Hazard statements: 314 · H314-H290
Precautionary statements: 501 · P501-P260-P234-P264-P280-P390-P303+P361+P353-P301+P330+P331-P363-P304+P340+P310-P305+P351+P338+P310-P406-P405
PPE: 3 · Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges
Hazard Codes: C
Risk Statements: 34 · 34
Safety Statements: 26 · 26-36/37/39-45
RIDADR: 3261 · UN 3261 8/PG 2
WGK Germany: 2 · 2
RTECS: 6950000 · AM6950000
F: 19 · 19-21
Hazard Note: Corrosive/Lachrymatory
TSCA: TSCA listed
HazardClass: 8 · 8
PackingGroup: III
HS Code: 29147090 · 29147090
Storage Class: 8 A · 8A - Combustible corrosive hazardous materials
Hazard Classifications: 1 B · Skin Corr. 1B
Limited Quantities: 1 Kg · 1 Kg (2.2 lbs) (solid)
Excepted Quantities: Max Inner Pack (30g or 30ml) and Max Outer Pack (500g or 500ml)

Safety & regulation

GHS classification

GHS Classification · 4 items

Danger

H314 (100%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]

P260, P264, P280, P301+P330+P331, P302+P361+P354, P304+P340, P305+P354+P338, P316, P321, P363, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 49 reports by companies from 4 notifications to the ECHA C&L Inventory.

Hazard information

Regulatory Information · 2 items

Chemical: Ethanone, 2-bromo-1-(4-bromophenyl)-

2,4'-Dibromoacetophenone: Does not have an individual approval but may be used under an appropriate group standard

Hazards SummaryCauses burns and lachrymation; Inhalation may cause corrosive injuries to upper respiratory tract and lungs; [Alfa Aesar MSDS] See alpha-Chloroacetophenone.

Hazard Classes and CategoriesSkin Corr. 1C (100%)

Toxicology

Adverse EffectsDermatotoxin - Skin burns.

Safety data

F: 19-21
PPE: Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges
wgk: 2
tsca: TSCA listed
rtecs: AM6950000
ridadr: UN 3261 8/PG 2
hs_code: 29147090
risk_code: 34
Signal word: Danger
Symbol(GHS): GHS05
hazard_code: C
hazard_note: Corrosive/Lachrymatory
safety_code: 26-36/37/39-45
hazard_class: 8
Storage Class: 8A - Combustible corrosive hazardous materials
packing_group: III
Hazard statements: H314-H290
Limited Quantities: 1 Kg (2.2 lbs) (solid)
Excepted Quantities: Max Inner Pack (30g or 30ml) and Max Outer Pack (500g or 500ml)
Hazard Classifications: Skin Corr. 1B
Precautionary statements: P501-P260-P234-P264-P280-P390-P303+P361+P353-P301+P330+P331-P363-P304+P340+P310-P305+P351+P338+P310-P406-P405

Chemistry & industry

Pharmacology

MeSH Pharmacological Classification · 2 items

Miscellaneous agents found useful in the symptomatic treatment of diarrhea. They have no effect on the agent(s) that cause diarrhea, but merely alleviate the condition.

Compounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.

Uses & manufacturing

UsesUsed to identify carboxylic acids; [Merck Index] Phospholipidase A(2) inhibitor. [ChemIDplus]

General Manufacturing InformationEthanone, 2-bromo-1-(4-bromophenyl)-: ACTIVE

Applications · 4 items

UsesIdentification of carboxylic acids.

UsesUndergoes condensation reactions with aldehydes in the presence of SnCl21 or SmI32 to afford α,β-unsaturated ketones. Also useful in the esterification of carboxylic acids.3

Uses2,4'-Dibromoacetophenone is used as a reagent for analysis of fatty acids by HPLC as 4-bromophenacyl esters, for use in the protection of phenols and carboxylic acids. It undergoes condensation reactions with aldehydes in the presence of SnCl2 or SmI3 to afford α,β-unsaturated ketones. It is also useful in the esterification of carboxylic acids.

General DescriptionA phenyl α-bromomethyl ketone compound that acts as a cell-permeable, and non-ATP competitive inhibitor of GSK-3β (IC50 = 0.5 μM). This reactive alkylating agent is selective towards GSK-3β and does not affect PKA activity even at concentrations as high as 100 μM.