Phenyl chloroformate

Phenyl chloroformate Basic information
Product Name:Phenyl chloroformate
Synonyms:PHENYL CHLOROFORMATE / CHLOROFORMIC ACID PHENYL ESTER;PHENYL CHLOROFORMATE (PCF);PHENYL CHLOROFORMAT;Phenyl carbonochloridic acid;PhenylChloroformate~93%;Chloridocarbonic acid phenyl ester;Chloroformic acid phenyl;Phenoxyformyl chloride
CAS:1885-14-9
MF:C7H5ClO2
MW:156.57
EINECS:217-547-8
Product Categories:Building Blocks;Carbonyl Compounds;Chemical Synthesis;Organic Building Blocks;Miscellaneous;Organics;CHLOROFORMATES;API Intermediate;Acid Halides;bc0001;K00001
Mol File:1885-14-9.mol
Phenyl chloroformate Structure
Phenyl chloroformate Chemical Properties
Melting point -28 °C
Boiling point 74-75 °C/13 mmHg (lit.)
density 1.248 g/mL at 25 °C (lit.)
vapor density 1 (vs air)
vapor pressure 1.22 psi ( 20 °C)
refractive index n20/D 1.511(lit.)
Fp 168 °F
storage temp. 2-8°C
solubility Miscible with N,N-dimethylformamide.
form Liquid
color Clear
Water Solubility hydrolysis
Sensitive Moisture Sensitive
BRN 606778
CAS DataBase Reference1885-14-9(CAS DataBase Reference)
NIST Chemistry ReferenceCarbonochloridic acid, phenyl ester(1885-14-9)
EPA Substance Registry SystemCarbonochloridic acid, phenyl ester (1885-14-9)
Safety Information
Hazard Codes T+
Risk Statements 22-26-34-41-38-29-37
Safety Statements 26-28-36/37/39-45-28A
RIDADR UN 2746 6.1/PG 2
WGK Germany 3
RTECS FG3850000
10-19-21
Autoignition Temperature540 °C
TSCA Yes
HazardClass 6.1
PackingGroup II
HS Code 29159020
ToxicityLD50 orally in Rabbit: 1730 mg/kg LD50 dermal Rabbit 4880 mg/kg
MSDS Information
ProviderLanguage
Carbonochloridic acid phenyl ester English
SigmaAldrich English
ACROS English
ALFA English
Phenyl chloroformate Usage And Synthesis
Chemical Propertiesclear oily liquid. Corrosive. Insoluble in water, soluble in ethanol, ether, easily soluble in petroleum ether.
UsesPhenyl 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.
PreparationPhenyl chloroformate is synthesized by the reaction of phenol with phosgene. Phenol was dissolved in chloroform, phosgene was introduced under cooling, and the absorbed phosgene was in an equal molar ratio to phenol, and equimolar N,N-dimethylaniline was added dropwise under stirring at 5-10 °C. Then add cold water to dilute, separate the oil layer, wash with dilute hydrochloric acid and water successively. After drying with anhydrous calcium chloride, chloroform is evaporated, and then distilled under reduced pressure to collect 74-75°C (1.73kPa) fraction, which is phenyl chloroformate. The yield is about 90%.
ApplicationPhenyl chloroformate is an important organic synthesis intermediate, which is widely used in chemical synthesis and can be used as polymer catalyst, plastic modifier, fiber treatment agent, and intermediate of medicine and pesticide.
General DescriptionPhenyl chloroformate appears as a colorless liquid with a strong odor. Toxic by ingestion, inhalation and skin absorption. Very irritating to skin and eyes. Used as a reagent for organic synthesis.
Air & Water ReactionsEmits fumes containing HCl in moist air. Decomposes in water to form HCl.
Reactivity ProfilePhenyl chloroformate is incompatible with strong oxidizing agents, alcohols, amines, alkali. May react vigorously or explosively if mixed with diisopropyl ether or other ethers in the presence of trace amounts of metal salts [J. Haz. Mat., 1981, 4, 291].
Health HazardTOXIC; inhalation, ingestion or contact (skin, eyes) with vapors, dusts or substance may cause severe injury, burns or death. Contact with molten substance may cause severe burns to skin and eyes. Reaction with water or moist air will release toxic, corrosive or flammable gases. Reaction with water may generate much heat that will increase the concentration of fumes in the air. Fire will produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution.
Fire HazardCombustible material: may burn but does not ignite readily. Substance will react with water (some violently) releasing flammable, toxic or corrosive gases and runoff. When heated, vapors may form explosive mixtures with air: indoors, outdoors and sewers explosion hazards. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapors may travel to source of ignition and flash back. Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated or if contaminated with water.
Safety ProfilePoison by inhalation. Moderately toxic by ingestion and skin contact. A corrosive sktn and eye irritant. See also ESTERS. When heated to decomposition it emits toxic fumes of Cl-.
(-)-Corey lactone 4-phenylbenzoate alcohol 2-NITROPHENYL CHLOROFORMATE Chlorocarbonic acid butanoyloxymethyl ester 2,4,5-trichlorophenyl chloroformate PHENYL RESIN Chlorocarbonic acid formyloxymethyl ester O-NITRYL CHLORINE PHENYL FORMATE Polyol benzoate 4-METHOXYCARBONYLPHENYL CHLOROFORMATE PHENYL VALERATE Chlorocarbonic acid acetylaminoacetyloxymethyl ester BUTYL OLEATE Chlorocarbonic acid (2-hydroxypropanoyl)oxymethyl ester Chlorocarbonic acid phenoxyacetyloxymethyl ester Phenyl butyrate Chloroformate Chlorocarbonic acid octanoyloxymethyl ester 4-CHLOROPHENYL CHLOROFORMATE

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