2-amino-5-methylbenzenesulfonamide Property

storage temp. 

2-8°C

InChI

InChI=1S/C7H10N2O2S/c1-5-2-3-6(8)7(4-5)12(9,10)11/h2-4H,8H2,1H3,(H2,9,10,11)

InChIKey

GKTVIFGJASUBGA-UHFFFAOYSA-N

SMILES

C1(S(N)(=O)=O)=CC(C)=CC=C1N

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P321Specific treatment (see … on this label).

P330Rinse mouth.

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P362Take off contaminated clothing and wash before reuse.

P501Dispose of contents/container to..…

2-amino-5-methylbenzenesulfonamide Chemical Properties,Usage,Production

Uses

2-amino-5-methylbenzenesulfonamide is an important organic reagent that can be used as a building block for the synthesis of many organic compounds. It could reacted with triethyl orthoformate to give 7-Methyl-4H-1,2,4-benzothiadiazine 1,1-dioxide by ring closure. It was an intermediate of potent AMPA receptor potentiators[1].

Synthesis

A solution of 7-methyl-3-oxo-3,4-dihydro-2H-1,2,4-benzothiadiazine 1,1-dioxide (10, 10 g, 47,12 mmol) in sulfuric acid 50% (150 mL) was refluxed until complete dissolution of the suspension. At the end of the reaction, the solution was adjusted to pH 7 with an aqueous solution of concentrated NaOH. The solvent was removed by distillation under reduced pressure. The residue was triturated with methanol and the salts were eliminated by filtration. The filtrate was concentrated to dryness under reduced pressure and the residue was triturated in water (a minimum). The resulting precipitate was collected by filtration, washed with water, and dried to afford 2-amino-5-methylbenzenesulfonamide[1].

References

[1] Dintilhac G, et al. New substituted aryl esters and aryl amides of 3,4-dihydro-2H-1,2,4-benzothiadiazine 1,1-dioxides as positive allosteric modulators of AMPA receptors. RSC Medicinal Chemistry, 2011; 2: 509-523.