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

A15576 2-Bromoacetophenone, 98%

Numéro de CAS
70-11-1
Synonymes
Phenacyl bromide

Conditionnement Prix ($) Quantité Disponibilité
25g 28,20
100g 67,90
500g 231,00
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2-Bromoacetophenone, 98%

MDL
MFCD00000195
EINECS
200-724-9

Propriétés chimiques

Formule
C8H7BrO
Poids moleculaire
199.05
Point de fusion
48-51°
Point d'ébullition
140°/11mm
Point d'éclair
>110°(230°F)
Densité
1.650
Solubilité
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.

Références bibliographiques

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).

Mentions de danger et de prudence du SGH

Mentions de danger (UE): H331-H314-H318

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

Mentions de prudence: P280-P305+P351+P338-P309-P310a

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:

Autres références

Merck
14,1402
Beilstein
606474
Classe de danger
6.1
Groupe d'emballage
II
Code tarifaire harmonisé
2914.79
TSCA
Yes

Recommandé

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Sciences de la vie

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Catalyseurs

Analytique et matériel de laboratoire