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

Chemical Properties

white to light yellow crystal powde

Uses

2-Amino-6-methylbenzothiazole was used 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.

Synthesis Reference(s)

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

General Description

The anti-tetanus activity of 2-amino-6-methylbenzothiazole, a muscle relactant, was studied.

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

An efficient one-pot synthesis of 2-aminobenzothiazoles from substituted anilines using benzyltrimethylammonium dichloroiodate and ammonium thiocyanate in DMSO:H2O

Treatment of a variety of substituted anilines with benzyltrimethylammonium dichloroiodate (1.2 equiv) and ammonium thiocyanate (1.0 equiv) in DMSO:H2O (9:1) at 70 °C gave the corresponding 2-aminobenzothiazoles in excellent isolated yields (75–97%; ave. yield for all substrates = 90%). The reaction worked well for 2(4)-mono-, 2,4-di-, or 3,4,5-tri-substituted anilines, and a wide range of both electron donating groups (MeO, HO, CF3O, Me) and electron withdrawing groups (NO2, CN, CO2Et, CO2H, Cl, F) were well tolerated. This method provides a useful alternative to other methods that are either less efficient (requiring 3–7 fold equivalents of reagents) or utilize highly toxic and corrosive liquid Br2 as the oxidizing agent.

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.