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

Description

Methyl 2-(chlorosulfonyl)benzoate is a white to beige or pink crystalline powder that serves as an important intermediate in the synthesis of various chemical compounds.

Uses

Used in Pharmaceutical Industry:
Methyl 2-(chlorosulfonyl)benzoate is used as an intermediate for the synthesis of pharmaceuticals, contributing to the development of new drugs and improving the efficacy of existing medications.
Used in Saccharin Production:
Methyl 2-(chlorosulfonyl)benzoate is utilized as an intermediate in the production of saccharin, a widely used artificial sweetener known for its ability to provide sweetness without adding calories.
Used in Dye Industry:
Methyl 2-(chlorosulfonyl)benzoate is employed as an intermediate in the synthesis of dyes, playing a crucial role in the creation of vibrant and long-lasting colorants for various applications.
Used in Pigment Industry:
Methyl 2-(chlorosulfonyl)benzoate is also used as an intermediate in the production of pigments, which are essential for creating a diverse range of colors in various industries, including paints, plastics, and cosmetics.

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

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

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 
• 22185-11-1 o-(N,N-Dimethyl-sulfamoyl)-benzoesaeure 
• 87223-28-7 2-(benzyl-methyl-sulfamoyl)-benzoic acid 
• 1026896-85-4 2-(4-Bromo-phenylsulfamoyl)-benzoic acid methyl ester 
• 87223-29-8 2-Diallylsulfamoyl-benzoic acid 
• 99943-10-9 2-Carbmethoxy-N-cyanomethyl-N-methyl-benzensulfonamid 
• 87223-35-6 2-(Methoxy-methyl-sulfamoyl)-benzoic acid 
• 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 

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.

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.

Method of preparing 2-chlorosulfonylmethyl benzoate from phthalic anhydride and urea

The invention provides a method of preparing 2-chlorosulfonylmethyl benzoate from phthalic anhydride and urea. The method includes the steps of 1) adding solid phthalic anhydride and urea into a reaction kettle and heating the materials to 135-143 DEG C to carry out a reaction to prepare o-aminobenzene dicarboximide, feeding the o-aminobenzene dicarboximide with water and sodium hydroxide into a first tubular reactor, forcedly cooling the mixture to -12 - -15 DEG C; 2) adding methanol and a sodium hypochlorite solution to perform Hoffman degradation reaction, and separating the reaction product to obtain o-aminomethyl benzoate; 3) according to the same mass ratio, feeding the o-aminomethyl benzoate and a sodium nitrite solution to a second tubular reactor, cooling the reactants to 0 DEG C, and adding sulfuric acid to perform a diazo-reaction for 11.5-11.8 s; and 4) continuously performing a cyclic sulfurization oxidation tubular reaction for 2 h, when the reactants show a dark green color on an benzidine-ethylamine test paper, adding methylbenzene and separating the reactant to obtain the 2-chlorosulfonylmethyl benzoate. The method is safe and simple, is advanced and integrated, is high in synthesis efficiency, has less side reactions and greatly reduces influence due to human factors.