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HomeProduct name listPhenyl chloroformate

Phenyl chloroformate

Synonym(s):Chloroformic acid phenyl ester;Chloroformic acid phenyl ester, Phenyl chlorocarbonate;Phenyl chloroformate

  • CAS NO.:1885-14-9
  • Empirical Formula: C7H5ClO2
  • Molecular Weight: 156.57
  • MDL number: MFCD00000637
  • EINECS: 217-547-8
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-08-24 19:19:26
Phenyl chloroformate Structural

What is Phenyl chloroformate?

Chemical properties

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

The Uses of Phenyl chloroformate

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%.

What are the applications of 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-.

Properties of Phenyl chloroformate

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)

Safety information for Phenyl chloroformate

Signal word Danger
Pictogram(s)
ghs
Corrosion
Corrosives
GHS05
ghs
Skull and Crossbones
Acute Toxicity
GHS06
GHS Hazard Statements H290:Corrosive to Metals
H302:Acute toxicity,oral
H314:Skin corrosion/irritation
H330:Acute toxicity,inhalation
H335:Specific target organ toxicity, single exposure;Respiratory tract irritation
Precautionary Statement Codes P234:Keep only in original container.
P280:Wear protective gloves/protective clothing/eye protection/face protection.
P301+P312:IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P303+P361+P353:IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

Computed Descriptors for Phenyl chloroformate

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