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70-11-1 - 2-Bromoacetophenone, 98% - Phenacyl bromide - A15576 - Alfa Aesar

A15576 2-Bromoacetophenone, 98%

CAS Number
70-11-1
Synonyms
Phenacyl bromide

Size Price ($) Quantity Availability
25g 24.84
100g 62.71
500g 188.80
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2-Bromoacetophenone, 98%

MDL
MFCD00000195
EINECS
200-724-9

Chemical Properties

Formula
C8H7BrO
Formula Weight
199.05
Melting point
48-51°
Boiling Point
140°/11mm
Flash Point
>110°(230°F)
Density
1.650
Solubility
Insoluble in water.

Applications

It is used in preparation of crystalline esters from acids. 2-Bromoacetophenone is a complete and irreversible inactivator of human liver aldehyde dehydrogenase isoenzymes E1 and E2.

Notes

Store in a cool, dry conditions in a well sealed container. Incompatible with oxidizing agent, acids & bases.

Literature References

E Bielak; S Biliński. [Reactions of 1-(X-benzoyl)-4-R-thiosemicarbazide with chloroacetone and µ-bromoacetophenone. VI. 4-(o-tolyl)-thiosemicarbazide of o-nitro - and p-nitrobenzoic acid]. Annales UMCS Medicina. 1996,51 185-193.

Adolfo Lopez Torres; Eunice Yanez Barrientos; Katarzyna Wrobel; Kazimierz Wrobel. Selective derivatization of cytosine and methylcytosine moieties with 2-bromoacetophenone for submicrogram DNA methylation analysis by reversed phase HPLC with spectrofluorimetric detection. Analytical chemistry 2011, 83 (20), 7999-8005.

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).

GHS Hazard and Precautionary Statements

Hazard Statements: H331-H314-H318

Toxic if inhaled. Causes severe skin burns and eye damage. Causes serious eye damage.

Precautionary Statements: P280-P305+P351+P338-P309-P310

Wear protective gloves/protective clothing/eye protection/face protection. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF exposed or if you feel unwell: Immediately call a POISON CENTER or doctor/physician.

Other References

Merck
14,1402
Beilstein
606474
Hazard Class
6.1
Packing Group
II
Harmonized Tariff Code
2914.70
TSCA
Yes

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