2-bromo-1-(4-bromophenyl)ethan-1-one

• ChemBase ID: 8898
• Molecular Formular: C8H6Br2O
• Molecular Mass: 277.94064
• Monoisotopic Mass: 275.87853881
• SMILES: C(=O)(c1ccc(cc1)Br)CBr
• Canonical SMILES: BrCC(=O)c1ccc(cc1)Br
• InChI: InChI=1S/C8H6Br2O/c9-5-8(11)6-1-3-7(10)4-2-6/h1-4H,5H2
• InChIKey: FKJSFKCZZIXQIP-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-bromo-1-(4-bromophenyl)ethan-1-one
• IUPAC Traditional name: 2-bromo-1-(4-bromophenyl)ethanone
• Synonyms: 2,4'-Dibromoacetophenone; 2,4′-Dibromoacetophenone; 4′-Bromophenacyl bromide; 2,4'-Dibromoacetophenone; 4-BROMOPHENACYL BROMIDE; 4-Bromophenacyl bromide 98%; 2-Bromo-1-(4-bromophenyl)ethanone; alpha,4-Dibromoacetophenone; 4-Bromophenacyl bromide; 2,4'-Dibromoacetophenone; 4′-溴苯甲酰甲基溴; 2,4′-二溴苯乙酮; 2,4'-二溴苯乙酮

Database IDs

• CAS Number: 99-73-0
• EC Number: 202-783-6
• MDL Number: MFCD00000200
• Beilstein Number: 607604
• Merck Index: 141427
• PubChem SID: 160972205; 24850825; 24893785
• PubChem CID: 7454

CALCULATED PROPERTIES

• Acid pKa: 15.461995
• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 3.022485
• LogD (pH = 7.4): 3.022485
• Log P: 3.022485
• Molar Refractivity: 51.8203 cm^3
• Polarizability: 19.844416 Å^3
• Polar Surface Area: 17.07 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: yellow to brown powder
• Melting Point: 108-110 °C(lit.); 108-110°C; 108-112 °C; 108-112°C

Safety Information

• Storage Condition: 0°C
• Storage Warning: Corrosive/Lachrymatory; LACHRYMATOR, CORROSIVE
• RTECS: AM6950000
• European Hazard Symbols: Corrosive (C)
• UN Number: 1759; 3261; UN3261
• German water hazard class: 2
• Hazard Class: 8
• Packing Group: 2; II
• Australian Hazchem: 2X
• Risk Statements: 34; R:34
• Safety Statements: 26-36/37/39-45; S:26-27/28-36/37/39-46-64
• EU Classification: C10
• EU Hazard Identification Number: 8B
• Emergency Response Guidebook(ERG) Number: 154
• TSCA Listed: true; 是
• GHS Pictograms: GHS05
• GHS Signal Word: Danger
• GHS Hazard statements: H314; H314-H318
• GHS Precautionary statements: P280-P305 + P351 + P338-P310; P280-P305+P351+P338-P309-P310
• Personal Protective Equipment: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• RID/ADR: UN 3261 8/PG 2
• Storage Temperature: 2-8°C

Pharmacology Properties

• Gene Information: human ... PLA2G2A(5320)rat ... Pla2g2a(29692)

Product Information

• Purity: >98%; ≥98.5% (HPLC); 98%; 98+%
• Grade: puriss.
• Linear Formula: BrC6H4COCH2Br

DETAILS

MP Biomedicals - 02150521

Crystalline

Sigma Aldrich - D38308

Packaging
10, 50, 100 g in glass bottle
Application
Undergoes 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

Sigma Aldrich - 17970

Other Notes
Modifies histidine residues in proteins1,2,3

REFERENCES

• The O-methyl oxime has been used to N-alkylate pyridines. The products can be cyclized with triethylamine to give imidazo[1,2-a]pyridines in high yield: Synthesis, 927 (1996).
• Reagent for analysis of fatty acids by HPLC as 4-bromophenacyl esters: Anal. Chem., 47, 1797, (1975).
• For use in the protection of phenols and carboxylic acids, see: Tetrahedron Lett., 343 (1970).