17462-58-7

Basic information

• Product Name: sec-Butyl chloroformate
• Synonyms: SBCF;SEC-BUTYL CHLOROFORMATE;carbonochloridicacid,1-methylpropylester;s-ButylChloroformate;Butan-2-yl carbonochloridate;Chloroformic acid sec-butyl este;sec-Butyl chlorocarbonate;Chloridocarbonic acid sec-butyl ester
• CAS NO: 17462-58-7
• Molecular Formula: C₅H₉ClO₂
• Molecular Weight: 136.58
• EINECS: 241-475-6
• Mol File: 17462-58-7.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 134.044 °C at 760 mmHg
• Flash Point: 35.842 °C
• Appearance: colorless liquid
• Density: 1.081 g/cm³
• Vapor Pressure: 8.236mmHg at 25°C
• Refractive Index: 1.417
• CAS DataBase Reference: sec-Butyl chloroformate(CAS DataBase Reference)
• NIST Chemistry Reference: sec-Butyl chloroformate(17462-58-7)
• EPA Substance Registry System: sec-Butyl chloroformate(17462-58-7)

Safety Data

• RIDADR: UN 2742
• HazardClass: 6.1(a)
• PackingGroup: II
• Hazardous Substances Data: 17462-58-7(Hazardous Substances Data)

Usage

General Description

A colorless liquid. Insoluble in water and more dense than water. Contact may severely irritate skin, eyes, and mucous membranes. Very toxic by ingestion, inhalation and skin absorption. Used to make other chemicals.

Air & Water Reactions

Reacts exothermically with moisture in air to generate fumes of hydrochloric acid. Decomposes slowly in water. Insoluble in water.

Reactivity Profile

sec-Butyl chloroformate reacts with water to form sec-butanol, HCl, and CO2. Attacks many metals, especially in humid atmosphere [Handling Chemicals Safely 1980. p. 476]. 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. 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.

InChI:InChI=1/C5H9ClO2/c1-3-4(2)8-5(6)7/h4H,3H2,1-2H3

Upstream product

• 75-44-5 phosgene 
• 78-92-2 iso-butanol 
• 32315-10-9 bis(trichloromethyl) carbonate 

Downstream Products

• 119598-34-4 N-({N²-[N-(toluene-4-sulfonyl)-L-pyroglutamyl]-L-glutaminyl})-L-alanine-benzyl ester 
• 37653-97-7 4-sec-Butoxycarbonylamino-benzoic acid 
• 623-63-2 Di(s-butyl) carbonate 
• 19910-65-7 di-sec-butyl peroxydicarbonate 
• 110745-20-5 carbonic acid, sec-butyl 3-phenylbenzofur-2-yl ester 
• 110745-15-8 2,3-dihydro-2-oxo-3-phenyl-3-benzofurancarboxylic acid, sec-butyl ester 
• 97419-33-5 α,β,α,β-5,10,15,20-tetrakisporphyrin 
• 121137-14-2 [(S)-1-(2-{(1Z,4Z,9Z,15Z)-15-(2-Amino-phenyl)-10,20-bis-[2-((S)-2-tert-butoxycarbonylamino-3-phenyl-propionylamino)-phenyl]-porphyrin-5-yl}-phenylcarbamoyl)-2-phenyl-ethyl]-carbamic acid tert-butyl ester 
• 121145-23-1 ((S)-2-Phenyl-1-{2-[(5Z,10Z,14Z,19Z)-10,15,20-tris-(2-amino-phenyl)-porphyrin-5-yl]-phenylcarbamoyl}-ethyl)-carbamic acid tert-butyl ester 
• 121137-11-9 [(S)-1-(2-{(1Z,4Z,9Z,15Z)-10,20-Bis-(2-amino-phenyl)-15-[2-((S)-2-tert-butoxycarbonylamino-3-phenyl-propionylamino)-phenyl]-porphyrin-5-yl}-phenylcarbamoyl)-2-phenyl-ethyl]-carbamic acid tert-butyl ester 
• 121137-15-3 [(S)-1-(2-{(1Z,4Z,9Z,15Z)-15-(2-Amino-phenyl)-10,20-bis-[2-((S)-2-tert-butoxycarbonylamino-3-methyl-butyrylamino)-phenyl]-porphyrin-5-yl}-phenylcarbamoyl)-2-methyl-propyl]-carbamic acid tert-butyl ester 
• 121145-14-0 α,β,α,β,-5,10,15,20-tetrakisporphyrin 
• 121145-24-2 ((S)-2-Methyl-1-{2-[(5Z,10Z,14Z,19Z)-10,15,20-tris-(2-amino-phenyl)-porphyrin-5-yl]-phenylcarbamoyl}-propyl)-carbamic acid tert-butyl ester 
• 121145-25-3 [(S)-1-(2-{(1Z,4Z,9Z,15Z)-10,20-Bis-(2-amino-phenyl)-15-[2-((S)-2-tert-butoxycarbonylamino-3-methyl-butyrylamino)-phenyl]-porphyrin-5-yl}-phenylcarbamoyl)-2-methyl-propyl]-carbamic acid tert-butyl ester 

Relevant articles and documents

Synthesis and enantioselective pharmacokinetic/ pharmacodynamic analysis of new CNS-active sulfamoylphenyl carbamate derivatives

We recently reported a new class of carbamate derivatives as anticonvulsants. Among these, 3-methylpentyl(4-sulfamoylphenyl)carbamate (MSPC) stood out as the most potent compound with ED50 values of 13 mg/kg (i.p.) and 28 mg/kg (p.o.) in the rat maximal electroshock test (MES). 3-Methylpropyl(4-sulfamoylphenyl)carbamate (MBPC), reported and characterized here, is an MSPC analogous compound with two less aliphatic carbon atoms in its structure. As both MSPC and MBPC are chiral compounds, here, we studied the carbonic anhydrase inhibitory and anticonvulsant action of both MBPC enantiomers in comparison to those of MSPC as well as their pharmacokinetic properties. Racemic-MBPC and its enantiomers showed anticonvulsant activity in the rat maximal electroshock (MES) test with ED50 values in the range of 19–39 mg/kg. (R)-MBPC had a 65% higher clearance than its enantiomer and, consequently, a lower plasma exposure (AUC) than (S)-MSBC and racemic-MSBC. Nevertheless, (S)-MBPC had a slightly better brain permeability than (R)-MBPC with a brain-to-plasma (AUC) ratio of 1.32 (S-enantiomer), 1.49 (racemate), and 1.27 (R-enantiomer). This may contribute to its better anticonvulsant-ED50 value. The clearance of MBPC enantiomers was more enantioselective than the brain permeability and MES-ED50 values, suggesting that their anticonvulsant activity might be due to multiple mechanisms of action.

Preparation method of sec-Butyl chloroformate

The invention relates to the field of organic synthesis, in particular relates to a preparation method of sec-Butyl chloroformate. The technical problems to be solved by the present invention is thatthe existing methods are costly, produce a large amount of organic waste liquid and, and are unfriendly to the environment. The solution of the present invention to solve the above technical problemsis to provide the preparation method of the sec-Butyl chloroformate. The preparation method comprises the following steps: using sec-butanol and triphosgene as reaction raw materials and a water-miscible aprotic organic solvent as a reaction solvent and adding an aqueous solution of an inorganic acid binding agent for reaction under the catalysis of an organic base to obtain the sec-Butyl chloroformate. The method provided by the invention greatly reduces the use amount of the organic solvent, is environmentally friendly, and produces no organic waste liquid. At the same time, raw material cost is reduced, and the post-treatment process is simple, so that the production process is smoother.

Facile chloride substitution of activated alcohols by triphosgene: Application to cephalosporin chemistry

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