Isobutyl chloroformate

Chemical properties

clear liquid

Chemical properties

A combustible, colorless to light-colored liquid.

The Uses of Isobutyl chloroformate

Isobutyl chloroformate is used as a peptide reagent. It is also used in the preparation of phenethyl-carbamic acid isobutyl ester by reaction with phenethylamine.

The Uses of Isobutyl chloroformate

To a solution of the SM (50.0 g, 218.0 mmol) in dry DCM (400 mL) at 0 C was added TEA (44.1 g, 437 mmol), followed by isobutyl chloroformate (596.0 g, 437.0 mmol). The reaction mixture was stirred at RT for 1 h, after which time it was concentrated in vacuo. The resulting material was cooled to 0 C and treated with NH4OH. The resulting solids were filtered, washed with H2O, and dried to provide the product as a white solid. [40.0 g, 80%]

General Description

A colorless to light-colored liquid. Insoluble in water and denser than water. Very corrosive to skin, eyes, and mucous membranes. Very toxic by ingestion, inhalation and skin absorption. Combustible.

Air & Water Reactions

Highly flammable. Insoluble in water. Reacts with moisture in the air to produce highly corrosive and toxic fumes of hydrogen chloride gas. Decomposes exothermically in water.

Reactivity Profile

Isobutyl chloroformate is incompatible with water, with strong oxidizing agents, alcohols, bases (including amines). 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].

Hazard

Flammable. Corrosive.

Health Hazard

TOXIC; inhalation, ingestion or contact (skin, eyes) with vapors, dusts or substance may cause severe injury, burns or death. Bromoacetates and chloroacetates are extremely irritating/lachrymators. 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

HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. Vapors 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. Substance will react with water (some violently) releasing flammable, toxic or corrosive gases and runoff. Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated or if contaminated with water.

Potential Exposure

This is a high volume chemical with production exceeding 1 million pounds annually in the U.S . No specific use found

Shipping

UN2742 Chloroformates, toxic, corrosive, flammable, n.o.s., Hazard class: 6.1; Labels: 6.1—Poison Inhalation Hazard, 8—Corrosive material; 3—Flammable liquid; Technical Name Required, Potential Inhalation Hazard (Special Provision 5). PG II. UN3390 Toxic by inhalation liquid, corrosive, n.o.s. with an LC50 # 1000 mL/m3 and saturated vapor concentration ≥ 10 LC50, Hazard Class: 6.1; Labels: 6.1—Poisonous materials, 8—Corrosive material, Technical Name Required, Inhalation Hazard Zone B

Purification Methods

It can be dried over CaCl2 and fractionated at atmospheric pressure while keeping moisture out. Its purity can be checked by conversion to the phenyl urethane derivative with PhNCO [Saunders et al. J Am Chem Soc 73 3796 1951.] IR: 1780cm-1 [Thompson & Jameson Spectrochim Acta 13 236 1959, R.se JustusLiebigs Ann Chem 205 227 1880]. [Beilstein 3 IV 26.]

Incompatibilities

Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, epoxides, alcohols, ethers, amines. Forms explosive mixture with air above flash point (27C). Compounds of the carboxyl group react with all bases, both inorganic and organic (i.e., amines) releasing substantial heat, water and a salt that may be harmful. Incompatible with arsenic compounds (releases hydrogen cyanide gas), diazo compounds, dithiocarbamates, isocyanates, mercaptans, nitrides, and sulfides (releasing heat, toxic and possibly flammable gases), thiosulfates and dithionites (releasing hydrogen sulfate and oxides of sulfur). Decomposes exothermically in water. Reacts with moisture in air to produce highly corrosive and toxic fumes of hydrogen chloride gas

Waste Disposal

Disposal of unused product must be undertaken by qualified personnel who are knowledgeable in all applicable regulations and follow all pertinent safety precautions including the use of appropriate protective equipment. For proper handling and disposal, always comply with federal, state, and local regulations.