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A12618 Phenyl chloroformate, 99%

CAS Number
1885-14-9
Synonyms
Chloroformic acid phenyl ester

Stock No. Size Price ($) Quantity Availability
A12618-22 100g 27.10
A12618-30 250g 63.20
A12618-36 500g 112.00
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Phenyl chloroformate, 99%

MDL
MFCD00000637
EINECS
217-547-8

Chemical Properties

Formula
ClCO2C6H5
Formula Weight
156.57
Melting point
-38°
Boiling Point
188-189°
Flash Point
76°(169°F)
Density
1.246
Refractive Index
1.5110
Storage & Sensitivity
Keep Cold. Moisture Sensitive. Store under Nitrogen.
Solubility
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.

Literature References

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.

GHS Hazard and Precautionary Statements

Hazard Statements: H227-H302-H314-H317-H330-H335

Combustible liquid. Harmful if swallowed. Causes severe skin burns and eye damage. May cause an allergic skin reaction. Fatal if inhaled. May cause respiratory irritation.

Precautionary Statements: P210-P235-P260-P264b-P270-P271-P272-P280-P284-P303+P361+P353-P304+P340-P305+P351+P338-P310-P330-P331-P333+P313-P363-P370+P378q-P501c

Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Keep cool. 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. Contaminated work clothing should not be allowed out of the workplace. Wear protective gloves/protective clothing/eye protection/face protection. 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. Immediately call a POISON CENTER or doctor/physician. Rinse mouth. Do NOT induce vomiting. If skin irritation or rash occurs: Get medical advice/attention. Wash contaminated clothing before reuse. In case of fire: Use CO2, dry chemical, or foam Dispose of contents/ container to an approved waste disposal plant

Other References

Beilstein
606778
Hazard Class
6.1
Packing Group
II
Harmonized Tariff Code
2915.90
TSCA
Yes
RTECS
FG3850000

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