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A15576 2-Bromoacetophenone, 98%

CAS Number
70-11-1
Synonyms
Phenacyl bromide

Stock No. Size Price ($) Quantity Availability
A15576-14 25g 29.40
A15576-22 100g 67.90
A15576-36 500g 236.00
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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
Storage & Sensitivity
Keep Cold.
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: H301-H314-H331

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

Precautionary Statements: P260-P264b-P270-P271-P280-P303+P361+P353-P304+P340-P305+P351+P338-P310-P330-P331-P363-P501c

Do not breathe dust/fume/gas/mist/vapours/spray. Wash face, hands and any exposed skin thoroughly after handling Do not eat, drink or smoke when using this product. Use only outdoors or in a well-ventilated area. Wear protective gloves/protective clothing/eye protection/face protection. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Immediately call a POISON CENTER or doctor/physician. Rinse mouth. Do NOT induce vomiting. Wash contaminated clothing before reuse. Dispose of contents/ container to an approved waste disposal plant

Other References

Merck
14,1402
Beilstein
606474
Hazard Class
6.1
Packing Group
II
Harmonized Tariff Code
2914.79
TSCA
Yes

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