2-Bromoacetophenone

• Catalog No.: A15576
• CAS Number: 70-11-1
• M. F.: C8H7BrO
• M. W.: 199.04458
• Purity: 98%

SYNONYMS

• Title: 2-溴苯乙酮
• IUPAC name: 2-bromo-1-phenylethan-1-one
• IUPAC Traditional name: phenacyl bromide
• Synonyms: Phenacyl bromide

DATABASE IDS

• MDL Number: MFCD00000195
• CAS Number: 70-11-1
• EC Number: 200-724-9
• Beilstein Number: 606474
• Merck Index: 141402

PROPERTIES

• Purity: 98%
• Boiling Point: 140°C/11mm
• Density: 1.650
• Flash Point: >110°C(230°F)
• Melting Point: 48-51°C
• GHS Hazard statements: H331-H314-H318
• European Hazard Symbols: Toxic (T)
• GHS Precautionary statements: P280-P305+P351+P338-P309-P310
• Risk Statements: 23-34
• Safety Statements: 26-36/37/39-45
• TSCA Listed: 是
• Hazard Class: 6.1
• UN Number: UN2645
• Packing Group: II

REFERENCES

• 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).