2-bromo-1-phenylethan-1-one

• ChemBase ID: 76533
• Molecular Formular: C8H7BrO
• Molecular Mass: 199.04458
• Monoisotopic Mass: 197.96802684
• SMILES: O=C(c1ccccc1)CBr
• Canonical SMILES: BrCC(=O)c1ccccc1
• InChI: InChI=1S/C8H7BrO/c9-6-8(10)7-4-2-1-3-5-7/h1-5H,6H2
• InChIKey: LIGACIXOYTUXAW-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-bromo-1-phenylethan-1-one
• IUPAC Traditional name: phenacyl bromide
• Synonyms: 1-Bromo-2-phenylethan-2-one; 1-Phenyl-2-bromoethanone; 2-Bromo-1-phenylethanone; Benzoylmethyl Bromide; Bromoacetophenone; NSC 9807; Phenyl Bromomethyl Ketone; Stauffer 4644; β-Bromoacetophenone; ω-Bromacetophenone; 2-Bromoacetophenone; ω-Bromoacetophenone; Phenacyl bromide; 2-Bromoacetophenone; 2-bromo-1-phenylethanone; 2-Bromoacetophenone; 2-Bromo-1-phenylethan-1-one; Phenacyl bromide 98%; α-Bromoacetophenone; Bromomethyl phenyl ketone; Phenacyl bromide; 2-bromo-1-phenylethan-1-one; ω-溴苯乙酮; 苯甲酰甲基溴; 2-溴苯乙酮

Database IDs

• CAS Number: 70-11-1
• EC Number: 200-724-9
• MDL Number: MFCD00000195
• Beilstein Number: 606474
• Merck Index: 141402
• PubChem SID: 162041437; 24887194; 24847241; 24887195
• PubChem CID: 6259
• CHEBI ID: 51846
• CHEMBL: 102953
• Chemspider ID: 6023
• Wikipedia Title: Phenacyl_bromide

CALCULATED PROPERTIES

• Acid pKa: 15.502873
• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 2.2537324
• LogD (pH = 7.4): 2.2537324
• Log P: 2.2537324
• Molar Refractivity: 44.1975 cm^3
• Polarizability: 16.77298 Å^3
• Polar Surface Area: 17.07 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: Colorless solid; Off-White Solid
• Melting Point: 47-50 °C; 48 - 51°C; 48-51 °C(lit.); 48-51°C; 48-51°C; 49-50 °C; 49-51°C; 50 °C
• Boiling Point: 135 °C/18 mmHg(lit.); 136 °C / 18mmHg; 140°C/11mm
• Flash Point: >110°C(230°F); 113 °C; 235.4 °F
• Density: 1.650
• Hydrophobicity(logP): 1.834

Safety Information

• Storage Condition: Refrigerator, Under Inert Atmosphere
• Storage Warning: Toxic/Irritant/Corrosive/Lachrymatory/Light Sensitive/Air Sensitive/Store under Argon/Keep Cold
• European Hazard Symbols: Corrosive (C); Toxic (T)
• UN Number: 2645; UN2645
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 2; II
• Risk Statements: 23-34; 34
• Safety Statements: 26-36/37/39-45
• TSCA Listed: 是
• GHS Pictograms: GHS05; GHS06
• GHS Signal Word: Danger
• Main Hazard: Toxic(T)
• GHS Hazard statements: H314; H331-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 2645 6.1/PG 2
• Storage Temperature: 2-8°C

Pharmacology Properties

• Gene Information: human ... PTPN6(5777)

Product Information

• Purity: ≥97.0% (GC); ≥99.0%; ≥99.0% (GC); 95%; 98%
• Grade: for GC derivatization; purum
• Linear Formula: C6H5COCH2Br

DETAILS

Sigma Aldrich - 115835

Frequently Asked Questions
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Packaging
5, 100, 500 g in glass bottle

Sigma Aldrich - 77450

Frequently Asked Questions
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Application
Preparation of crystalline esters from acids

Toronto Research Chemicals - B679065

2-Bromoacetophenone is a brominated acteophenone derivative. 2-Bromoacetophenone has been shown to completely and irreversibly inactivate human liver aldehyde dehydrogenase (EC 1.2.1.3) isoenzymes E1 and E2. 2-Bromoacetophenone and its derivatives display

REFERENCES

• MacKerell, A.D. et al.: Biochemistry, 25, 5182 (1986)
• Arabaci, G. et al.: Biiorg. Med. Chem. Lett., 12, 3047 (1986)
• Reagent for carboxyl protection as phenacyl esters, stable to acid hydrolysis but readily cleaved by nucleophiles or by reduction. See Appendix 6. Protection can be effected in the presence of triethylamine: J. Chem. Soc. (C), 1191 (1966), or, better, KF in DMF: Tetrahedron Lett., 599 (1977). Phase-transfer conditions have also been reported: Synth. Commun., 26, 1747 (1996). Cleavage has been described using a variety of reagents, including Zn-AcOH: Tetrahedron Lett., 343 (1970), catalytic hydrogenolysis, treatment with PhS^-, PhSeH, or NaHTe: Synth. Commun., 18, 116 (1988); TBAF: J. Org. Chem., 56, 5465 (1991); or photolysis: J. Org. Chem., 62, 6245 (1997).
• Has also been used to block the imidazole ring in histidine residues during peptide synthesis, and is stable to TFA, TfOH and HBr-AcOH: J. Chem. Soc., Chem. Commun., 472 (1978); J. Chem. Soc., Perkin 1, 2261 (1979).
• For formation of the Sn enolate using SnCl₂, see: Synth. Commun., 23, 271 (1993). 1,4-Diketones may be synthesized from ɑ-bromoketones and Sn enolates: J. Chem. Soc., Perkin 1, 3205 (1990).