2-Chloro-5-chloromethylthiazole Chemical Properties

Melting point:

31

Boiling point:

268.6±32.0 °C(Predicted)

Density 

1.503±0.06 g/cm3(Predicted)

refractive index 

n20/D1.571

storage temp. 

Keep in dark place,Inert atmosphere,2-8°C

solubility 

soluble in Methanol

pka

0.19±0.10(Predicted)

color 

White to Light yellow

BRN 

5861439

InChI

InChI=1S/C4H3Cl2NS/c5-1-3-2-7-4(6)8-3/h2H,1H2

InChIKey

VRMUIVKEHJSADG-UHFFFAOYSA-N

SMILES

S1C(CCl)=CN=C1Cl

CAS DataBase Reference

105827-91-6(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,N,T

Risk Statements 

36/37/38-51/53-43-34-24-22

Safety Statements 

26-37-61-45-36/37/39

RIDADR 

2922

WGK Germany 

3

Hazard Note 

Irritant

HazardClass 

8

PackingGroup 

Ⅱ

HS Code 

29349990

2-Chloro-5-chloromethylthiazole Usage And Synthesis

Description

2-Chloro-5-chloromethylthiazole is used as pharmaceutical and agrochemical intermediate. It is also used as intermediate of insecticides Thiamethoxam and Clothianidin. It is also useful in in the synthesis of Ritonavir (R535000); a second-generation anti-AIDS drug and a selective HIV protease inhibitor.

Chemical Properties

White crystal or powder

Uses

2-Chloro-5-(chloromethyl)thiazole is a useful synthetic intermediate used in the synthesis of Ritonavir (R535000)

Synthesis

To a 2-liter round bottomed flask equipped with a mechanical stirrer, thermometer and a condenser, whose outlet was vented into an aqueous sodium hydroxide trap, was charged the crude mixture of cis- and trans-3-chloropropenyl isothiocyanates (504.2 g, 3.79 mol) and chloroform (600 mL). The mixture was stirred and heated to reflux. Chlorine (267.1 g, 3.77 mole) gas was bubbled under the surface of the reaction over a period of 6-8 h. The conversion of the isothiocyanates to 2-chloro-5- (chloromethyl)thiazole was monitored by GC. When the reaction was shown to be complete by GC analysis, the reaction mixture was cooled and then filtered. The filtrate was concentrated on the rotary evaporator to remove chloroform. Sodium bicarbonate (approximately 0.25 equivalents) was added to the concentrated filtrate, and the product 2-chloro-5-chloromethylthiazole was distilled at 97 °C under vacuum (6mm/Hg). The yield after distillation was 43%. 1 H NMR (CDCl3) δ: 7.3 (s, 1H); 4.6 (s, 2H). 13C NMR (CDCl3) δ: 152.6 (C-2); 140.2 (C-4); 137.5 (C-5); 37.1 (-CH2-).

References

[1] Patent: CN108484524, 2018, A. Location in patent: Paragraph 0051; 0052; 0053; 0054
[2] Patent: CN105294595, 2016, A. Location in patent: Paragraph 0013; 0014; 0015; 0016; 0017
[3] Journal of Agricultural and Food Chemistry, 2004, vol. 52, # 7, p. 1918 - 1922
[4] Patent: CN107935960, 2018, A. Location in patent: Paragraph 0031-0043
[5] Patent: CN105949145, 2016, A. Location in patent: Paragraph 0045; 0046

2-Chloro-5-chloromethylthiazole(105827-91-6)Related Product Information

• 4,6-Dichloropyrimidine
• 2-Chlorothiazole
• Chloromethane
• DIMETHYLTHEXYLSILYL CHLORIDE
• Metronidazole
• Dimethyl sulfone
• Nucleoside
• tert-Butyldimethylsilyl chloride
• 2-Methyl-4-isothiazolin-3-one
• 4-(Chloromethyl)benzoic acid
• Chloromethyl methyl ether
• Difluorochloromethane
• Thiamethoxam
• 5-Thiazolecarbonyl chloride, 2-chloro- (9CI)
• 5-CHLOROMETHYL-2,4-DICHLOROTHIAZOLE
• 2-Chloro-5-chloromethylthiazole
• 2-(4-BROMOPHENOXY)-4-CHLORO-5-CHLOROMETHYLTHIAZOLE
• 2-(3-CARBOXYPHENOXY)-4-CHLORO-5-CHLOROMETHYLTHIAZOLE