2-(CHLOROMETHYL)-1,3-BENZOTHIAZOLE Chemical Properties

Melting point:

34℃

Boiling point:

102°/0.5mm

Density 

1.371

Flash point:

120℃

storage temp. 

Inert atmosphere,Store in freezer, under -20°C

solubility 

soluble in Methanol

form 

Solid

pka

0.43±0.10(Predicted)

Appearance

Off-white to light yellow <34°C Solid,>34°C Liquid

Sensitive 

Moisture Sensitive

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

22-37/38-41-43

Safety Statements 

26-36/37-39

HazardClass 

IRRITANT

HS Code 

2934208090

2-(CHLOROMETHYL)-1,3-BENZOTHIAZOLE Usage And Synthesis

Synthesis Reference(s)

Synthetic Communications, 19, p. 2921, 1989 DOI: 10.1080/00397918908052683

Synthesis

General procedure for the synthesis of 2-(chloromethyl)-1,3-benzothiazole from 2-hydroxymethylbenzothiazole: To a stirred solution containing 2-hydroxymethylbenzothiazole (2.5 g, 15.1 mmol), triphenylphosphine (4.89 g, 18.6 mmol), and anhydrous toluene (50 ml) was added, protected by nitrogen, carbon tetrachloride (15.0 ml, 155 mmol ). The reaction mixture was heated to reflux for 5 hours. After completion of the reaction, the reaction mixture was concentrated using a rotary evaporator to give the crude product. The crude product was purified by rapid chromatography on silica gel to afford 2-(chloromethyl)-1,3-benzothiazole (2.36 g, 85% yield) using 100% dichloromethane as eluent. The product was confirmed by mass spectrometry (ion spray): m/z = 183.9 (M + 1); 1H NMR (CDCl3) data were as follows: δ= 8.04-8.01 (1H, m), 7.91-7.89 (1H, m), 7.53-7.49 (1H, m), 7.44-7.40 (1H, m), 4.95 (2H, s).

References

[1] Tetrahedron, 1988, vol. 44, # 7, p. 2021 - 2032
[2] Chemical Communications, 2017, vol. 53, # 54, p. 7545 - 7548
[3] Patent: WO2005/92885, 2005, A1. Location in patent: Page/Page column 55
[4] Zhurnal Obshchei Khimii, 1954, vol. 24, p. 1664,1667; engl. Ausg. 1645, 1647
[5] Zhurnal Obshchei Khimii, 1956, vol. 26, p. 797,798; engl. Ausg. 911, 912

2-(CHLOROMETHYL)-1,3-BENZOTHIAZOLE(37859-43-1)Related Product Information

• Benzothiazole
• 3-chloromethyl-3h-benzothiazole-2-thione
• DIMETHYL 2-[1,3-BENZOTHIAZOL-2-YL(CHLORO)METHYLENE]-1,3-DITHIOLE-4,5-DICARBOXYLATE
• Benzothiazole, 2-(1-chloroethyl)- (9CI)
• Benzothiazole, 2-(chloromethyl)-4-fluoro- (9CI)
• 1,3-BENZOTHIAZOL-2-YL(DICHLORO)ACETONITRILE
• Benzothiazole, 2-(chloromethyl)-5-fluoro- (9CI)
• 1,3-BENZOTHIAZOLE-2-CARBONYL CHLORIDE
• 2-(CHLOROMETHYL)-1,3-BENZOTHIAZOLE