10147-37-2

Basic information

• Product Name: ISOPROPYLSULFONYL CHLORIDE
• Synonyms: PROPANE-2-SULFONYL CHLORIDE;2-PROPANESULFONYL CHLORIDE;2-PROPANESULPHONYL CHLORIDE;ISOPROPYLSULFONYL CHLORIDE;ISOPROPYLSULPHONYL CHLORIDE;Isopropylsulphonyl choride;1-Methylethanesulfonic acid chloride;1-Methylethanesulfonyl chloride
• CAS NO: 10147-37-2
• Molecular Formula: C₃H₇ClO₂S
• Molecular Weight: 142.6
• EINECS: 233-415-2
• Product Categories: Organic Building Blocks;Sulfonyl Halides;Sulfur Compounds
• Mol File: 10147-37-2.mol

Chemical Properties

• Melting Point: -47°C
• Boiling Point: 74-75 °C19 mm Hg(lit.)
• Flash Point: 187 °F
• Appearance: clear pale yellow-greenish liquid
• Density: 1.27 g/mL at 25 °C(lit.)
• Vapor Density: 4 (vs air)
• Vapor Pressure: 15.5 mm Hg ( 25 °C)
• Refractive Index: n20/D 1.453(lit.)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Water Solubility: Reacts with water.
• Sensitive: Lachrymatory
• BRN: 1747497
• CAS DataBase Reference: ISOPROPYLSULFONYL CHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: ISOPROPYLSULFONYL CHLORIDE(10147-37-2)
• EPA Substance Registry System: ISOPROPYLSULFONYL CHLORIDE(10147-37-2)

Safety Data

• Hazard Codes: C
• Statements: 34-R34
• Safety Statements: 26-28-36/37/39-45-S45-S36/37/39-S28-S26
• RIDADR: UN 3265 8/PG 2
• WGK Germany: 3
• F: 13-19-21
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 10147-37-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
ISOPROPYLSULFONYL CHLORIDE is used as a pharmaceutical intermediate for the reductive cleavage of a secondary alcohol to methylene. This is achieved by reduction of the 2-propanesulfonyl ester with lithium triethylborohydride, which is a crucial step in the synthesis of certain pharmaceutical compounds.
Used in Chemical Synthesis:
ISOPROPYLSULFONYL CHLORIDE is used as a reactant for the preparation of 1-Isopropylsulfonyl-2-amine benzimidazole. This is done through an N-sulfonylation reaction with 2-aminobenzimidazole in the presence of a base, which is essential for the development of specific chemical compounds.
Used in Synthesis of Phosphorothioate Oligonucleotide Analogs:
ISOPROPYLSULFONYL CHLORIDE is also used in the synthesis of Bis(isopropylsulfonyl)disulfide, a sulfurizing agent. This agent is crucial for the production of phosphorothioate oligonucleotide analogs, which have significant applications in the field of molecular biology and genetic research.
General Description:
The solvolysis of ISOPROPYLSULFONYL CHLORIDE by an addition-elimination (association-dissociation) pathway has been studied, providing valuable insights into its chemical behavior and potential applications in various industries.

InChI:InChI=1/C3H7ClO2S/c1-3(2)7(4,5)6/h3H,1-2H3

Upstream product

• 74-98-6 propane 
• 625-59-2 2-propyl thiocyanate 
• 18939-66-7 S-isopropyl-isothiourea; hydrochloride 
• 19760-04-4 isopropylsulfenyl chloride 
• 4253-89-8 diisopropyl sulfide 
• 75-33-2 2-propanethiol 
• 5399-58-6 propane-2-sulfonic acid ; sodium-salt 
• 14159-48-9 2-propanesulfonic acid 
• 81363-76-0 propane-2-sulfonamide 

Downstream Products

• 81363-76-0 propane-2-sulfonamide 
• 60901-23-7 N-phenylpropane-2-sulfonamide 
• 2819-09-2 methyl isopropanesulfonate 
• 25077-99-0 propane-2-sulphonic acid p-cresylester 
• 25077-98-9 Isopropan-sulfonsaeure-(o-methyl-phenyl-ester) 
• 71270-53-6 Propane-2-sulfonic acid (2,6-dimethyl-phenyl)-amide 
• 96118-09-1 Aethyl-4-(2-propansulfonamido)benzoat 
• 4798-87-2 2,2,4,4-tetramethyl-3-pyrrolidinothietane 1,1-dioxide 
• 1731-56-2 4,4-dimethyl-2-phenyl-3-pyrrolidinothietane 1,1-dioxide 
• 90233-73-1 N-Phenyl-3-(propane-2-sulfonylamino)-benzamide 
• 132680-64-9 2-amino-1-(isopropylsulfonyl)-1H-imidazo<4,5-d>pyridin-6-yl phenyl ketone 
• 140660-68-0 (4S,5S)-4-Cyclohexylmethyl-2,2-dimethyl-5-[(S)-3-methyl-2-(propane-2-sulfonylamino)-butyl]-oxazolidine-3-carboxylic acid tert-butyl ester 
• 95729-31-0 <2-Amino-1-<(1-methylethyl)sulfonyl>-1H-thieno<2,3-d>imidazol-5-yl>-phenylmethanon 
• 118195-40-7 Propane-2-sulfonic acid (3aR,5aR,9aS,9bR)-3a-[1,3]dioxolan-2-yl-6,9a-dimethyl-2-phenylsulfanyl-dodecahydro-naphtho[2,1-b]furan-6-ylmethyl ester 

Relevant articles and documents

Selective Late-Stage Sulfonyl Chloride Formation from Sulfonamides Enabled by Pyry-BF4

Reported here is a simple and practical functionalization of primary sulfonamides, by means of a pyrylium salt (Pyry-BF4), with nucleophiles. This simple reagent activates the poorly nucleophilic NH2 group in a sulfonamide, enabling the formation of one of the best electrophiles in organic synthesis: a sulfonyl chloride. Because of the variety of primary sulfonamides in pharmaceutical contexts, special attention has been focused on the direct conversion of densely functionalized primary sulfonamides by a late-stage formation of the corresponding sulfonyl chloride. A variety of nucleophiles could be engaged in this transformation, thus permitting the synthesis of complex sulfonamides, sulfonates, sulfides, sulfonyl fluorides, and sulfonic acids. The mild reaction conditions and the high selectivity of Pyry-BF4 towards NH2 groups permit the formation of sulfonyl chlorides in a late-stage fashion, tolerating a preponderance of sensitive functionalities.

Sulfonyl halide synthesis by thiol oxyhalogenation using NBS/NCS – iPrOH

A rapid and facile method provides a general route to sulfonyl bromides/chlorides by the oxidation of thiols using NXS – ROH (X?=?Br,Cl, R?=?iPr) as an oxyhalogenation reagent. Control experiments suggest that the alcohol component is the source of oxygen. The proposed method enable the access to structurally diverse sulfonyl bromides and chlorides including challenging examples, inaccessible by other synthetic methods.

An easy microwave-assisted synthesis of sulfonamides directly from sulfonic acids

(Chemical Equation Presented) An easy and handy synthesis of sulfonamides directly from sulfonic acids or its sodium salts is reported. The reaction is performed under microwave irradiation, has shown a good functional group tolerance, and is high yielding.

(BIS)sulfonamide derivatives

The present invention provides (bis) sulfonamide derivatives of formula (I) useful for potentiating glutamate receptor function in a mammal and therefore, useful for treating a wide variety of conditions, such as psychiatric and neurological disorders.

N-substituted sulfonamide derivatives

The present invention provides certain N-substituted sulfonamide derivatives useful for potentiating glutamate receptor function in a mammal and therefore, useful for treating a wide variety of conditions, such as psychiatric and neurological disorders.

Sulphonamide derivatives

Glutamate receptor function in a mammal may be potentiated using an effective amount of a compound of formulaR1—L—NHSO2R2??Iin whichR1 represents an unsubstituted or substituted aromatic or heteroaromatic group;R2 represents (1-6C)alkyl, (3-6C)cycloalkyl, (1-6C)fluoroalkyl, (1-6C)chloroalkyl, (2-6C)alkenyl, (1-4C)alkoxy(1-4C)alkyl, phenyl which is unsubstituted or substituted by halogen, (1-4C)alkyl or (1-4C)alkoxy, or a group, of formula R3R4N in which R3 and R4 each independently represents (1-4C)alkyl or, together with the nitrogen atom to which they are attached form an azetidinyl, pyrrolidinyl, piperidinyl, morpholino, piperazinyl, hexahydroazepinyl or octahydroazocinyl group; andL represents a (2-4C)alkylene chain which is unsubstituted or substituted by one or two substituents selected independently from (1-6C)alkyl, aryl(1-6C)alkyl, (2-6C)alkenyl, aryl(2-6C)alkenyl and aryl, or by two substituents which, together with the carbon atom or carbon atoms to which they are attached form a (3-8C)carbocyclic ring;and pharmaceutically acceptable salts thereof.Also disclosed are compounds of formula I, processes for preparing them and pharmaceutical compositions containing them.

Mechanisms of hydrolysis and related nucleophilic displacement reactions of alkanesulfonyl chlorides: pH dependence and the mechanism of hydration of sulfenes

pH-rate profiles, primary kinetic isotope effects, deuterium substitution patterns, and pH-product ratios in the presence of added nucleophiles provide evidence for the following overlapping set of mechanisms for the hydrolysis of methanesulfonyl chloride (1) (in 0.1 M KCl at 25 °C): (a) pH ≤ 1-6.7, reaction with water by direct nucleophilic attack on the sulfonyl chloride; (b) pH ≥ 6.7-11.8, rate-determining attack by hydroxide anion to form sulfene (2), which is then trapped by water in a fast step; and (c) pH ≥ 11.8, sulfene formation and sulfene trapping by hydroxide anion; careful inspection showed no sign of sulfene formation in the reaction with water or of direct displacement by hydroxide anion. This pattern, with appropriate variations in the values of pHi (the pH at which two competing mechanisms have the same rate), is apparently general for simple alkanesulfonyl chlorides having at least one hydrogen on the carbon bearing the sulfonyl group. Azide and acetate anions react with 1 below pHi for 1 (6.7) by direct nucleophilic substitution at the sulfur, but above pHi by trapping of the sulfene. 2-Chlorophenoxide anion reacts with 1 below pH 6.7 by both (a) direct displacement to form the ester and (b) elimination to form the sulfene. Above pH 6.7, sulfene is formed from the sulfonyl chloride by reaction with either 2-chlorophenoxide or hydroxide ion; this is followed by trapping of the sulfene with 2-chlorophenoxide, water, or hydroxide. The possibility of the 2-chlorophenoxide anion acting as a general base promoting the reaction of water with either 1 and 2 was examined, but no sign of either process was detected.

Convenient One-Pot Synthesis of Sulfonyl Chlorides from Thiols Using Sulfuryl Chloride and Metal Nitrate

Various sulfonyl chlorides were obtained in excellent yields by the reaction of alkyl and aryl thiols with sulfuryl chloride in the presence of metal nitrate under mild condition in aprotic solvents such as acetonitrile and N,N-dimethylformamide.

Studies on the Base-catalyzed Solvolysis of Propane-2-sulphonic Acid p-Cresylester

Products of the reaction of propane-2-sulphonic acid p-cresylester with sodium butoxide in butanol are the sodium salt of propan-2-sulphonic acid, di-n-butyl ether, p-cresyl-n-butyl ether and p-cresol.The reaction proceeds via propane-2-sulphonic acid n-butylester which is formed from the starting compound by an elimination-addition (sulphene) mechanism.The elimination step is an E1-cB reaction.

N-sulfonyl-N-dihalophenylimidazolidinediones

3-(3' -Dihalophenyl)-1-sulfonylimidazolidine-2,4-5'-diones of the formula: STR1 wherein X is a halogen atom, R1 is a C1 -C12 alkyl group, a C2 -C4 alkenyl group or a halogenated C1 -C4 alkyl group having 1 to 3 halogen atoms, and R2 and R3 are individually a hydrogen atom or a methyl group, which show high microbicidal activities against various fungi and bacteria without any material toxicity to mammals and which plants and can be produced by reacting the corresponding 1-unsubstituted compound with a sulfonyl halide.