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1885-14-9 - Phenyl chloroformate, 99% - Chloroformic acid phenyl ester - A12618 - Alfa Aesar

A12618 Phenyl chloroformate, 99%

Numéro CAS
1885-14-9
Synonymes
Chloroformic acid phenyl ester

Dimensions Prix ($) Quantité Disponibilité
100g 25,65
250g 60,46
500g 97,07
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Phenyl chloroformate, 99%

MDL
MFCD00000637
EINECS
217-547-8

Propriétés chimiques

Formule
ClCO2C6H5
Poids formulaire
156.57
Point de fusion
-38°
Point d'ébullition
188-189°
Point d'éclair
76°(169°F)
Densité
1.246
Indice de réfraction
1.5110
Sensibilité
Moisture Sensitive
Solubilité
Miscible with N,N-dimethylformamide.

Applications

Phenyl chloroformate is used in the synthesis of poly(2-(phenoxycarbonyloxy)ethyl methacrylate) and phenyl-(4-vinylphenyl) carbonate. It acts as a precursor of phenyl mixed anhydrides which are used in peptide coupling reactions. It serves as a dehydrating reagent for the conversion of primary amides to nitriles and an intermediate in the synthesis of pharmaceuticals and carbamates.

Notes

Store in cool place. Moisture sensitive. Keep the container tightly closed in a dry and well-ventilated place. Incompatible with bases, alcohols and amines. Hydrolyses in water.

Références bibliographiques

Precursor of phenyl mixed anhydrides, which can be used, e.g. in peptide coupling reactions.

Also used in the cleavage of tertiary amines: J. Chem. Soc. (C), 2015 (1967); cf Ethyl­ chloroformate, L06311, and 1-Chloroethyl­ chloroformate, L14197. Review: Synthesis, 1 (1989).

Reagent for dehydration of primary amides to nitriles under mild conditions: Indian J. Chem., 40B, 722 (2001).

Wieting, J. M.; Fisher, T. J.; Schafer, A. G.; Visco, M. D.; Gallucci, J. C.; Mattson, A. E. Preparation and Catalytic Activity of BINOL-Derived Silanediols. Eur. J. Org. Chem. 2015, 2015 (3), 525-533.

Kevill, D. N.; Ryu, Z. H. Correlation of the rates of solvolysis of 2, 1-benzoxathiol-3-one-1, 1-dioxide (2-sulfobenzoic acid cyclic anhydride). J. Chem. Res. 2015, 39 (10), 561-566.

Mentions de danger et de prudence du SGH

Mentions de danger (UE): H330-H302-H317-H314-H318-H227-H313

Fatal if inhaled. Harmful if swallowed. May cause an allergic skin reaction. Causes severe skin burns and eye damage. Causes serious eye damage. Combustible liquid. May be harmful in contact with skin.

Mentions de prudence: P210-P260-P284-P303+P361+P353-P304+P340-P305+P351+P338-P320-P330-P405-P501a

Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Do not breathe dust/fume/gas/mist/vapours/spray. Wear respiratory 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. Specific treatment is urgent (see label). Rinse mouth. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Autres références

Beilstein
606778
Classe de danger
6.1
Groupe d'emballage
II
Code tarifaire harmonisé
2915.90
TSCA
Yes
RTECS
FG3850000

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Analytique et matériel de laboratoire