26638-43-7

Basic information

• Product Name: Methyl 2-(chlorosulfonyl)benzoate
• Synonyms: Methyl 2-(chlorosulphonyl)benzoate;Methyl 2-(chlorosulfonyl)benzoate, tech., 93%;Benzoic acid, 2-(chlorosulfonyl)-, methyl ester;o-(Methoxycarbonyl)benzenesulphonyl chloride;Methyl 2-(chlorosulfonyl)benzoate, 90%, tech.;Methyl 2-(chlorosulfonyl)benzoateCBC;Methyl 2-(chorosulfonyl)benzoate;Methyl 2-(chlorosulfonyl)benzoate ,95%
• CAS NO: 26638-43-7
• Molecular Formula: C₈H₇ClO₄S
• Molecular Weight: 234.66
• EINECS: 1806241-263-5
• Product Categories: pharmacetical
• Mol File: 26638-43-7.mol
• Article Data: 16

Chemical Properties

• Melting Point: 62-63 °C
• Boiling Point: 344.8 °C at 760 mmHg
• Flash Point: 162.3 °C
• Appearance: White to beige or pink/Crystalline Powder or Chunks
• Density: 1.4452 (estimate)
• Storage Temp.: 0-6°C
• Water Solubility: reacts
• Sensitive: Moisture Sensitive
• CAS DataBase Reference: Methyl 2-(chlorosulfonyl)benzoate(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl 2-(chlorosulfonyl)benzoate(26638-43-7)
• EPA Substance Registry System: Methyl 2-(chlorosulfonyl)benzoate(26638-43-7)

Safety Data

• Hazard Codes: C
• Statements: 34-29-14
• Safety Statements: 45-36/37/39-30-26-22
• RIDADR: 3261
• TSCA: Yes
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 26638-43-7(Hazardous Substances Data)

Usage

Chemical Properties

white to beige or pink crystalline powder

Uses

Methyl 2-(chlorosulfonyl)benzoate can be used as intermediates in pharmaceuticals, saccharin, dyes, & pigments.

Synthesis Reference(s)

Synthesis, p. 1203, 1992 DOI: 10.1055/s-1992-26333

InChI:InChI=1/C8H7ClO4S/c1-13-8(10)6-4-2-3-5-7(6)14(9,11)12/h2-5H,1H3

Synthetic route

2-[(methoxymethyl)sulfanyl]benzoic acid methyl ester (146335-12-8) → 2-methoxycarbonylbenzenesulfonyl chloride (26638-43-7)

Conditions	Yield
With water; chlorine In dichloromethane at 5 - 10℃; for 1h;	96%
With water; chlorine In dichloromethane at 5 - 10℃; for 1h; Product distribution; other aryl(or benzyl) methoxymethyl sulfides, also with N-chlorosuccinimide;	96%

2-carbomethoxyaniline (134-20-3) → 2-methoxycarbonylbenzenesulfonyl chloride (26638-43-7)

Conditions	Yield
Stage #1: 2-carbomethoxyaniline With hydrogenchloride; sodium nitrite In water at 20℃; for 0.00555556h; Flow reactor; Stage #2: With hydrogenchloride; sodium hydrogensulfite; copper(l) chloride In water at 0 - 20℃; Temperature; Concentration; Time; Balz-Schiemann Reaction;	95%
Stage #1: 2-carbomethoxyaniline With hydrogenchloride; sodium nitrite In water at 80℃; for 0.0277778h; Large scale; Stage #2: With sodium hydrogensulfite In dichloromethane; water at 100℃; for 0.025h; Solvent; Reagent/catalyst; Temperature; Large scale;	94%
With sodium hypochlorite; sulfuric acid at 0℃; for 2h;

2-(methoxycarbonyl)benzenediazonium tetrafluoroborate (342-54-1) → 2-methoxycarbonylbenzenesulfonyl chloride (26638-43-7)

Conditions	Yield
With thionyl chloride; tris(bipyridine)ruthenium(II) dichloride hexahydrate In water; acetonitrile at 20℃; for 20h; Sealed tube; Irradiation;	85%

chloroamine-T (127-65-1) + Methyl thiosalicylate (4892-02-8) → methyl 2-[(N-chloro-4-methylbenzenesulfonamido)sulfinyl]benzoate + 2-methoxycarbonylbenzenesulfonyl chloride (26638-43-7)

Conditions	Yield
With N-chloro-succinimide In water; acetonitrile at 35℃; for 0.25h;	A 50% B 18%

methanol (67-56-1) + 2-chlorosulfonylbenzoyl chloride (34684-21-4) → 2-methoxycarbonylbenzenesulfonyl chloride (26638-43-7)

bis[2-(methoxycarbonyl)phenyl]disulfide (5459-63-2) → 2-methoxycarbonylbenzenesulfonyl chloride (26638-43-7)

Conditions	Yield
With water; chlorine

2-methoxycarbonyl-benzenesulfinic acid (119300-80-0) → 2-methoxycarbonylbenzenesulfonyl chloride (26638-43-7)

Conditions	Yield
With water; chlorine

2-methoxycarbonyl-benzenediazonium-chloride → 2-methoxycarbonylbenzenesulfonyl chloride (26638-43-7)

Conditions	Yield
With sulfur dioxide; copper(l) chloride

alkali salt of/the/ benzoic acid methyl ester-o-sulfinic acid → 2-methoxycarbonylbenzenesulfonyl chloride (26638-43-7)

Conditions	Yield
With water; chlorine

2-(methoxycarbonyl)benzenesulfonic acid (57897-77-5) → 2-methoxycarbonylbenzenesulfonyl chloride (26638-43-7)

Conditions	Yield
With phosphorus pentachloride at 95℃; for 2.5h;	2.51 g
With phosphorus pentachloride at 95℃; for 12h;	7.42 g

Conditions	Yield
Multi-step reaction with 2 steps 1: 1 h / Heating 2: 2.51 g / PCl5 / 2.5 h / 95 °C View Scheme
Multi-step reaction with 2 steps 1: 4 h / Reflux 2: phosphorus pentachloride / 12 h / 95 °C View Scheme

Upstream product

• 81-08-3 2-sulfobenzoic acid cyclic anhydride 
• 7446-09-5 sulfur dioxide 
• 134-20-3 2-carbomethoxyaniline 
• 85-44-9 phthalic anhydride 
• 342-54-1 2-(methoxycarbonyl)benzenediazonium tetrafluoroborate 
• 127-65-1 chloroamine-T 
• 4892-02-8 Methyl thiosalicylate 
• 57897-77-5 2-(methoxycarbonyl)benzenesulfonic acid 
• 146335-12-8 2-[(methoxymethyl)sulfanyl]benzoic acid methyl ester 
• 119300-80-0 2-methoxycarbonyl-benzenesulfinic acid 
• 5459-63-2 bis[2-(methoxycarbonyl)phenyl]disulfide 
• 67-56-1 methanol 
• 34684-21-4 2-chlorosulfonylbenzoyl chloride 

Downstream Products

• 119300-80-0 2-methoxycarbonyl-benzenesulfinic acid 
• 55120-13-3 2-[methyl-(thiazol-2-ylcarbamoyl-methyl)-sulfamoyl]-benzoic acid methyl ester 
• 87223-34-5 2-(morpholinosulfonyl)benzoic acid 
• 63113-47-3 2-(p-tolyl)benzo[d]isothiazol-3(2H)-one-1,1-dioxide 
• 111874-90-9 2-Phenethylsulfamoyl-benzoic acid methyl ester 
• 108293-25-0 (-)-<(-)-menthyl 2-carbomethoxybenzenesulfinate> 
• 88312-74-7 2-(2-bromo-4-methylphenyl)-1,2-benzisothiazol-3(2H)-one 1,1-dioxide 
• 145006-90-2 2-[2-(4-Bromo-phenyl)-ethylsulfamoyl]-benzoic acid methyl ester 
• 141556-86-7 2-[2-((1R,2S,6R,9R,12S)-12-Methoxy-9-methyl-10,11,13-trioxa-tricyclo[7.2.2.0^1,6]tridec-2-yl)-ethoxysulfonyl]-benzoic acid methyl ester 
• 145865-94-7 methyl 2-(hydrazinosulfonyl)benzoate 
• 853799-21-0 methyl N-(1-acetylindolin-5-yl)-2-sulfamoyl benzoate 
• 15448-99-4 N-methylsaccharin 

Relevant articles and documents

Sulfonium ion-promoted traceless Schmidt reaction of alkyl azides

Schmidt reaction by sulfonium ions is described. General primary, secondary, and tertiary alkyl azides were converted to the corresponding carbonyl or imine compounds without any trace of the activators. This bond scission reaction through 1,2-migration of C-H and C-C bonds was accessible to the one-pot substitution reaction.

Aminoxidation of Arenethiols to N-Chloro-N-sulfonyl Sulfinamides

A simple and efficient method to synthesize N-chloro-N-sulfonylsulfinamides by the direct aminoxidation of arenethiols under aqueous and mild conditions is disclosed, geminally installing the oxo and amino groups on the sulfur atom of arenethiols. The products have been primarily developed as sulfinylation reagents to convert Grignard reagents into sulfoxides, and as amination reagents to convert secondary amines into hydrazine derivatives.

Continuous-Flow Diazotization for Efficient Synthesis of Methyl 2-(Chlorosulfonyl)benzoate: An Example of Inhibiting Parallel Side Reactions

An expeditious process for the highly efficient synthesis of methyl 2-(chlorosulfonyl)benzoate was described, which involved the continuous-flow diazotization of methyl 2-aminobenzoate in a three-inlet flow reactor via a cross joint followed by chlorosulfonylation in the tandem tank reactor. The side reaction such as hydrolysis was decreased eminently from this continuous-flow process even at a high concentration of hydrochloric acid. The mass flow rate of methyl 2-aminobenzoate was 4.58 kg/h, corresponding to an 18.45 kg/h throughput of diazonium salt solution. The potential of inhibiting parallel side reactions by conducting in a flow reactor was successfully demonstrated in this method.