2536-91-6

Basic information

• Product Name: 2-Amino-6-methylbenzothiazole
• Synonyms: 2-Amino-6-methylbenzthiazol;2-Imino-6-methylbenzothiazoline;2-Methylbenzothiazol-2-amine;6-Methyl-2-aminobenzothiazole;6-Methyl-2-benzothiazolylamine;Benzothiazole, 2-amino-6-methyl-;SKF 1045;AKOS BBS-00005695
• CAS NO: 2536-91-6
• Molecular Formula: C₈H₈N₂S
• Molecular Weight: 164.23
• EINECS: 219-801-3
• Product Categories: Intermediates of Dyes and Pigments;BENZOTHIAZOLE;Sulphur Derivatives;Thiazole;Amines;Heterocyclic Compounds;Building Blocks;Heterocyclic Building Blocks;Thiazoles;Building Blocks;C8 to C9;Chemical Synthesis;Heterocyclic Building Blocks
• Mol File: 2536-91-6.mol
• Article Data: 97

Chemical Properties

• Melting Point: 140-142 °C(lit.)
• Boiling Point: 322 °C at 760 mmHg
• Flash Point: 148.6 °C
• Appearance: white to light yellow crystal powder
• Density: 1.1724 (rough estimate)
• Vapor Pressure: 0.000287mmHg at 25°C
• Refractive Index: 1.5700 (estimate)
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Solubility: soluble in Methanol
• PKA: 4.41±0.10(Predicted)
• CAS DataBase Reference: 2-Amino-6-methylbenzothiazole(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Amino-6-methylbenzothiazole(2536-91-6)
• EPA Substance Registry System: 2-Amino-6-methylbenzothiazole(2536-91-6)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 3
• RTECS: DL2625000
• TSCA: Yes
• Hazardous Substances Data: 2536-91-6(Hazardous Substances Data)

Usage

Description

2-Amino-6-methylbenzothiazole is a white to light yellow crystalline compound with the molecular formula C7H8N2S. It is a heterocyclic organic compound that belongs to the benzothiazole family, characterized by the presence of a sulfur atom and an amino group in its structure. 2-Amino-6-methylbenzothiazole is known for its potential applications in various fields, particularly in the pharmaceutical industry.

Uses

Used in Pharmaceutical Industry:
2-Amino-6-methylbenzothiazole is used as an intermediate in the synthesis of various pharmaceutical compounds. One of its applications is in the preparation of 2-[(6-methyl-1,3-benzothiazol-2-yl)amino]-N-[2-(substituted phenyl/furan-2-yl)-4-oxo-1,3-thiazolidin-3-yl]nicotinamides, which are compounds with potential therapeutic properties.
Used in Anti-tetanus Applications:
2-Amino-6-methylbenzothiazole has been studied for its anti-tetanus activity, which makes it a potential candidate for use as a muscle relaxant in the treatment of tetanus, a serious bacterial infection that causes muscle stiffness and spasms.

Synthesis Reference(s)

Organic Syntheses, Coll. Vol. 3, p. 76, 1955The Journal of Organic Chemistry, 68, p. 8693, 2003 DOI: 10.1021/jo0349431

InChI:InChI=1/C8H8N2S/c1-5-2-3-6-7(4-5)11-8(9)10-6/h2-4H,1H3,(H2,9,10)

Upstream product

• 2268-79-3 6-methyl-1,3-benzothiazole-2(3H)-thione 
• 622-52-6 p-methylphenylthiourea 
• 540-72-7 sodium thiocyanide 
• 106-49-0 p-toluidine 
• 1147550-11-5 ammonium thiocyanate 
• 15192-76-4 copper(II) thiocyanate 
• 28241-61-4 ammonia thiocyanic acid 
• 1111-67-7 copper(I) thiocyanate 
• 333-20-0 potassium thioacyanate 
• 7647-01-0 hydrogenchloride 
• 13078-28-9 5-(p-tolylamino)-1,2,3,4-thiatriazole 
• 56-23-5 tetrachloromethane 
• 7791-25-5 sulfuryl dichloride 
• 108-90-7 chlorobenzene 

Downstream Products

• 261505-37-7 N-(6-methyl-benzothiazol-2-yl)-succinamic acid 
• 85063-53-2 N-(4-chlorophenyl)-6-methylbenzo[d]thiazol-2-amine 
• 108718-01-0 N-phenyl-N'-(6-methylbenzothiazol-2-yl)urea 
• 1819-80-3 N-phenyl-N'-(6-methyl)benzothiazolylthiocarbamide 
• 85063-55-4 N-(4-methoxyphenyl)-6-methylbenzo[d]thiazol-2-amine 
• 76076-09-0 (6-methyl-benzothiazol-2-yl)-carbamic acid methyl ester 
• 67058-58-6 6-methyl-2-phenylamino-1,3-benzothiazole 
• 90564-99-1 (6-methyl-benzothiazol-2-yl)-urea 
• 52853-54-0 3,6-dimethyl-3H-benzothiazol-2-ylideneamine 
• 3507-26-4 2-chloro-6-methylbenzo[d]thiazole 
• 47165-11-7 6,6'-Dimethyl-2,2'-imino-bis- 
• 23451-96-9 2-amino-5-methylthiophenol 
• 92987-73-0 N-<2-(6-methyl)benzothiazolyl>cyanamide 

Relevant articles and documents

Condensation of 2-Amino-1,3-thiazole Salts and Benzo Analogs with Trifluoroacetylacetone

Abstract: The condensation of 2-amino-1,3-thiazolium perchlorates and their benzo analogs with trifluoro-acetyl-acetone in acetic acid afforded the corresponding [1,3]thiazolo[3,2-a]pyrimidinium, pyrimido[2,1-b][1,3]benzothiazolium, and naphtho[2′,1′:4,5][1,3]thiazolo[3,2-a]pyrimidinium salts as a single isomer in which the trifluoromethyl group is located in the γ-position with respect to the bridgehead nitrogen atom. The structure of the synthesized compounds was confirmed by 1H NMR spectra and elemental analyses.

Visible-light-initiated malic acid-promoted cascade coupling/cyclization of aromatic amines and KSCN to 2-aminobenzothiazoles without photocatalyst

By using ambient air as the oxidant and malic acid as the promoter, a practical method for the preparation of 2-aminobenzothiazoles through visible-light-initiated cascade reaction of aromatic amines and KSCN in eco-friendly bis(methoxypropy)ether under metal-, hazardous additive-, photocatalyst-free conditions was established.

Visible-light photoredox catalytic approach for the direct synthesis of 2-aminobenzothiazoles from anilines

A novel, highly efficient and convenient approach for the visible-light-promoted direct synthesis of 2-aminobenzothiazoles from anilines and ammonium thiocyanate is presented. The reaction involves addition/cyclization cascade of SCN radical and anilines under photoredox catalysis with Ru(bpy)3Cl2. The salient features of the protocol include the utilization of atmospheric oxygen and visible light as clean, inexpensive and sustainable resources at room temperature.