17462-58-7

Usage

Uses

Used in Chemical Synthesis:
sec-Butyl chloroformate is used as an intermediate in the synthesis of various chemicals, including pharmaceuticals, agrochemicals, and other specialty chemicals. Its reactivity allows it to form esters, carbonates, and carbamates, making it a versatile building block in organic chemistry.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, sec-Butyl chloroformate is used as a reagent for the synthesis of active pharmaceutical ingredients (APIs) and drug intermediates. Its ability to form esters and carbonates enables the production of a wide range of drug molecules with specific therapeutic properties.
Used in Agrochemical Industry:
In the agrochemical industry, sec-Butyl chloroformate is used as a precursor for the synthesis of various agrochemicals, such as insecticides, herbicides, and fungicides. Its reactivity allows for the creation of molecules with targeted pest control properties.
Used in Specialty Chemicals:
sec-Butyl chloroformate is also used in the production of specialty chemicals, such as fragrances, dyes, and polymers. Its versatility in forming different types of chemical bonds makes it a valuable component in the synthesis of these complex molecules.

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 
• 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 
• 334513-53-0 phenoxyacetyl 1-methyl-1-propyl carbonate 
• 334513-52-9 3-chlorobenzoyl 1-methyl-1-propyl carbonate 
• 948552-65-6 C₂₃H₂₄N₆O₄ 
• 103131-63-1 Z-D-Ser((N-isobuyoxycarbonyl)-Pro-Gly-Sar-Val)-OCpa 
• 121145-14-0 α,β,α,β,-5,10,15,20-tetrakisporphyrin 

Relevant academic research and scientific papers

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.

Synthesis and application of nitenpyram acyl derivative (by machine translation)

The invention relates to synthesis and application of nitenpyram acyl derivatives represented by general formula (I), and the compound represents a broad-spectrum efficient insecticidal bactericide structure type. The nitenpyram acyl derivative can well prevent and treat aphids, diamondback and beet armyworms; and can be well used for preventing and treating cucumber brown spot, cucumber bacterial disease, cucumber fusarium wilt, cucumber downy mildew, cucumber powdery mildew, tomato bacterial spot disease and rice sheath blight disease. The meaning of R in the formula is given in the description. (by machine translation)

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.

Design, synthesis and cytotoxicity of novel 3′-N-alkoxycarbonyl docetaxel analogs

By-product 9a exhibited potent cytotoxicity against both SK-OV-3 and A549 cell lines. The structure of 9a was characterized using 1D and 2D NMR experiments and confirmed by synthesis to afford a diastereomeric mixture (16a) that was identical to 9a, as well as a pair of diastereomers (R)-16b and (S)-16c. The preliminary SAR study demonstrated that analogs with an (R)-configuration were slightly more potent than analogs with an (S)-configuration. In addition, α,α-gem-dimethyl analogs 16g-i were the most potent analogs in this series, exhibiting similar potency to docetaxel and greater potency than Taxol against the SK-OV-3 cell line. For the A549 cell line, analogs 16g-i were more potent (>65-fold) than both docetaxel and Taxol.

KINETICS AND MECHANISM OF THE PHOSGENATION OF ALIPHATIC ALCOHOLS II. EFFECT OF THE SOLVENT ON THE REACTION RATE

A quantitative analysis of the effect of the characteristics of the medium on the phosgenation rate of alcohols was made by means of the parameters of the Koppel-Palm equation.An equation is proposed which describes the effect of the solvent on the reaction rate and which takes account of the interdependence of the components of nonspecific and specific solvation.The applicability of the proposed equation to other solvolytic reactions was demonstrated.An equation is obtained which makes it possible to asses the phosgenation rate of alcohols in relation to the properties of the medium and the structure of the alcohol.

KINETICS AND MECHANISM OF PHOSGENATION OF ALIPHATIC ALCOHOLS

The kinetics of the reaction of phosgene with various aliphatic alcohols were investigated in heptane and dioxane and without a solvent.The effects of the polarity of the medium the structure of the alcohol, and the activation parameters of the process are consistent with an addition-elimination mechanism.

Novel penicillin compounds and process for preparation thereof

A penicillin compound of the formula STR1 wherein R is a formyl or acetyl group, and a nontoxic pharmaceutically acceptable salt thereof. The penicillin compound is prepared by (A) reacting a compound of the formula STR2 or its salt or its reactive derivative at the carboxyl group, with 6-α-amino-p-hydroxybenzylpenicillin or its salt or its derivative, or reacting a compound of the formula STR3 or its salt or its reactive derivative at the carboxyl group, with 6-aminopenicillanic acid or its salt or its derivative, (B) optionally hydrolyzing or catalytically hydrogenolyzing the reaction product, and (C) optionally converting the reaction product to a nontoxic pharmaceutically acceptable salt. The penicillin compound has low toxicity and superior antibacterial activity especially against bacteria of the genus Pseudomonas and is suitable for parenteral administration, especially for an intramuscular, intravenous or subcutaneous injection.

Tetrahydro-azepinoquinolines

Compounds of the formula SPC1 Wherein EQU1 where R1 is hydrogen, straight or branched aliphatic acyl of 1 to 12 carbon atoms, methoxy-substituted straight or branched aliphatic acyl of 1 to 12 carbon atoms, benzoyl, halo-benzoyl, carbalkoxy of 2 to 7 carbon atoms, carbcycloalkoxy of 4 to 7 carbon atoms, benzyl, methylbenzyl, phenylsulfonyl, halo-phenylsulfonyl, tolylsulfonyl, alkenyl of 2 to 6 carbon atoms, phenyl, trifluoroacetyl, amidino, amido, thioamido, phenoxycarbonyl, benzyloxycarbonyl, methylsulfonyl or where B is straight or branched alkylene of 1 to 6 carbon atoms, and X is hydrogen, hydroxyl, methoxy, carboxyl, cyano, dimethylaminocarbonyl, morpholino-carbonyl or carbalkoxy of 2 to 6 carbon atoms, R2 is hydrogen, hydroxyl, alkyl of 1 to 3 carbon atoms, alkoxy of 1 to 3 carbon atoms, alkanoyloxy of 1 to 3 carbon atoms, alkoxycarbonyloxy of 2 to 4 carbon atoms, amino, dimethylamino, morpholino or halogen, R3 is hydrogen, halogen, hydroxyl, carboxyl, straight or branched alkyl of 1 to 6 carbon atoms, cycloalkyl of 3 to 6 carbon atoms, alkoxy of 1 to 3 carbon atoms, phenyl-alkoxy of 1 to 3 carbon atoms, carbalkoxy of 2 to 4 carbon atoms -- alkoxy of 1 to 3 carbon atoms, carbalkoxy of 2 to 4 carbon atoms, hydroxymethyl, phenyl, phenoxy, amino, pyrrolidino or morpholino, R4, r5 and R6, which may be identical to or different from each other, are each hydrogen, halogen, methyl, hydroxyl, methoxy, cyano, amino, nitro, trifluoromethyl, carboxyl, acetyl or carbalkoxy of 2 to 4 carbon atoms, or any two of R4, R5 and R6 together are methylenedioxy, and X1 and X2 are hydrogen or together form a double bond, 6-N-oxides thereof, and non-toxic, pharmacologically acceptable acid addition salts thereof; the compounds as well as their salts are useful as anoretics.