6939-89-5

Basic information

• Product Name: 2-SULFOBENZOIC ACID MONOAMMONIUM SALT
• Synonyms: 2-sulfo-benzoicacimonoammoniumsalt;Benzoicacid,2-sulfo-,monoammoniumsalt;AMMONIUM ACID SULFOBENZOATE;AMMONIUM O-SULFOBENZOATE;2-SULFOBENZOIC ACID AMMONIUM SALT;2-SULFOBENZOIC ACID MONOAMMONIUM SALT;O-SULFOBENZOIC ACID, AMMONIUM SALT;O-SULFOBENZOIC ACID MONOAMMONIUM SALT
• CAS NO: 6939-89-5
• Molecular Formula: C₇H₆O₅S*H₃N
• Molecular Weight: 219.22
• EINECS: 230-077-8
• Mol File: 6939-89-5.mol
• Article Data: 3

Chemical Properties

• Melting Point: 274-277°C
• Boiling Point: 521 °C at 760 mmHg
• Flash Point: 268.9 °C
• Appearance: /
• Storage Temp.: Store below +30°C.
• CAS DataBase Reference: 2-SULFOBENZOIC ACID MONOAMMONIUM SALT(CAS DataBase Reference)
• NIST Chemistry Reference: 2-SULFOBENZOIC ACID MONOAMMONIUM SALT(6939-89-5)
• EPA Substance Registry System: 2-SULFOBENZOIC ACID MONOAMMONIUM SALT(6939-89-5)

Safety Data

• WGK Germany: WGK 3 highly water endangering
• Hazardous Substances Data: 6939-89-5(Hazardous Substances Data)

Usage

Purification Methods

o-Sulfobenzoic acid (monoammonium salt) [6939-89-5] M 219.5. Crystallise the salt from water.

InChI:InChI=1/C7H6O5S.H3N/c8-7(9)5-3-1-2-4-6(5)13(10,11)12;/h1-4H,(H,8,9)(H,10,11,12);1H3/p+1

Upstream product

• 81-07-2 saccharin 
• 128-44-9 saccharin sodium salt 

Downstream Products

• 81-07-2 saccharin 
• 34684-21-4 2-chlorosulfonylbenzoyl chloride 
• 81-08-3 2-sulfobenzoic acid cyclic anhydride 
• 221242-55-3 2-[methoxycarbonylmethyl-(2-trifluoromethyl-phenyl)-sulfamoyl]-benzoic acid methyl ester 
• 221242-51-9 2-(2-trifluoromethyl-phenylsulfamoyl)-benzoic acid methyl ester 
• 221242-67-7 4-hydroxy-1,1-dioxo-2-(2-trifluoromethyl-phenyl)-1,2-dihydro-1λ6-benzo[e][1,2]thiazine-3-carboxylic acid methyl ester 
• 221242-70-2 1,1-dioxo-4-(trifluoro-methanesulfonyloxy)-2-(2-trifluoromethyl-phenyl)-1,2-dihydro-1λ6-benzo[e][1,2]thiazine-3-carboxylic acid methyl ester 
• 98755-05-6 2-(3,6-dihydroxy-xanthen-9-yl)-benzenesulfonic acid 

Relevant articles and documents

Synthesis of a few cyclothiadiazanones and aminosulfonyl benzamides from saccharin

Saccharin is hydrolyzed with two different acids to yield 1,2-di-acid. The di-acid, on chlorination with phosphorous pentachloride, gave 2-chlorosulfonylbenzoyl chloride. The 2-chlorosulfonylbenzoyl chloride on hydrazinolysis gave benzothiadiazinetrione, while with phenyl hydrazine it selectively yielded 2-phenylbenzothiadiazinetrione. 2-chlorosulfonoylbenzoyl chloride with different aromatic 1,2- diamines resulted in dibenzothiadiazocine derivatives. Electron-donating groups in the diamine facilitate while the electron-withdrawing groups retard the cyclization. However, aliphatic diamines, aniline and substituted anilines readily gave acyclic aminosulfonyl carboxybenzamides on condensation with 2- chlorosulfonylbenzoyl chloride. The di-acid and anhydride did not react with either hydrazine/phenyl hydrazine or amines to give the above products. However, when its ester derivative, isopropyl-2- chlorosulfonylbenzoate, condensed with hydrazine, it gave benzothiadiazinetrione. But the ester failed to react with phenyl hydrazine. All the condensation reactions were carried out at room temperature.

Development of a scalable process for CI-1034, an endothelin antagonist

A concise, convergent multikilogram synthesis of CI-1034 (1), a potent endothelin receptor antagonist, is described. A 15-step preparation from commercially available o-vanillin and benzenesulfonyl chloride employs a remarkably robust Suzuki coupling between a boronic acid and an aromatic sulfonate ester as the key synthetic step. A scalable route capable of producing multikilogram quantities of CI-1034 with no chromatographic steps is described in this contribution. Improvements to the process included using a 4-fluorobenzenesulfonate ester as a suitable substitute for the triflate group in the Suzuki reaction and the use of MgCl2 as a substitute for TiCl4 in a Dieckmann condensation to provide the benzothiazine dioxide core.