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Phenyl chloroformate

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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%
  • CARBONOCHLORIDIC ACID
  • chlorocarbonic acid
  • carbonochloridic acid phenyl ester
CAS:
1885-14-9
MF:
C7H5ClO2
MW:
156.57
EINECS:
217-547-8
Product Categories:
  • API Intermediate
  • Acid Halides
  • Building Blocks
  • Carbonyl Compounds
  • Chemical Synthesis
  • Organic Building Blocks
  • Miscellaneous
  • Organics
  • CHLOROFORMATES
  • bc0001
  • K00001
Mol File:
1885-14-9.mol
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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.)
Flash point:
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 Reference
1885-14-9(CAS DataBase Reference)
NIST Chemistry Reference
Carbonochloridic acid, phenyl ester(1885-14-9)
EPA Substance Registry System
Carbonochloridic acid, phenyl ester (1885-14-9)
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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 Temperature
540 °C
TSCA 
Yes
HazardClass 
6.1
PackingGroup 
II
HS Code 
29159020
Toxicity
LD50 orally in Rabbit: 1730 mg/kg LD50 dermal Rabbit 4880 mg/kg

MSDS

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Phenyl chloroformate Usage And Synthesis

Chemical Properties

clear oily liquid. Corrosive. Insoluble in water, soluble in ethanol, ether, easily soluble in petroleum ether.

Uses

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.

Preparation

Phenyl 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%.

Application

Phenyl 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 Description

Phenyl 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 Reactions

Emits fumes containing HCl in moist air. Decomposes in water to form HCl.

Reactivity Profile

Phenyl 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 Hazard

TOXIC; 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 Hazard

Combustible 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 Profile

Poison 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-.

Phenyl chloroformateSupplier

SHANGHAI BANGCHENG CHEMICAL Co.,Ltd. Gold
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Meryer (Shanghai) Chemical Technology Co., Ltd.
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Alfa Aesar
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400-6106006
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saleschina@alfa-asia.com