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 
• 56-23-5 tetrachloromethane 
• 7791-25-5 sulfuryl dichloride 
• 108-90-7 chlorobenzene 
• 3674-54-2 tetrabutylammonium thiocyanate 
• 333-20-0 potassium thioacyanate 
• 100-01-6 4-nitro-aniline 
• 855281-37-7 6-methyl-2-nitro-benzothiazole 

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.

Tandem Copper-Catalyzed Regioselective N-Arylation-Aza-Michael Addition: Synthesis of Tetracyclic 5 H-Benzothiazolo[3,2- a]quinazoline Derivatives

A copper-catalyzed tandem process integrating regioselective N-arylation, followed by aza-Michael addition, is disclosed using 2-aminobenzothiazoles and ortho-halo cinnamic acid congeners. This process generated diverse tetracyclic 5H-benzothiazolo[3,2-a]quinazoline derivatives in moderate to good yields. The present tandem reaction appears to proceed through concomitant ring opening of 2-aminobenzothiazole and S-arylation to give the ortho-cyanamide-substituted diaryl thioether intermediate. The thus generated intermediate likely undergoes an unprecedented Truce-Smiles-type rearrangement involving S- to N-aryl migration, followed by reformation of the thiazole ring and intramolecular aza-Michael addition to furnish the title products.