Chloromethyl isopropyl carbonate Chemical Properties

Boiling point:

66 °C(Press: 16 Torr)

Density 

1.14

refractive index 

1.4110-1.4150

Flash point:

50°

storage temp. 

Inert atmosphere,2-8°C

solubility 

Chloroform (Slightly), DMSO, Ethyl Acetate (Slightly)

form 

clear liquid

color 

Colorless to Almost colorless

Stability:

Moisture sensitive

Major Application

pharmaceutical (small molecule)

InChI

InChI=1S/C5H9ClO3/c1-4(2)9-5(7)8-3-6/h4H,3H2,1-2H3

InChIKey

JHYNXXBAHWPABC-UHFFFAOYSA-N

SMILES

C(OC(C)C)(=O)OCCl

CAS DataBase Reference

35180-01-9(CAS DataBase Reference)

Safety Information

Safety Statements 

24/25

RIDADR 

2924

WGK Germany 

WGK 3

HazardClass 

3/8

PackingGroup 

Ⅲ

HS Code 

29189900

Storage Class

10 - Combustible liquids

Hazard Classifications

Aquatic Chronic 2
Skin Irrit. 2
Skin Sens. 1

Chloromethyl isopropyl carbonate Usage And Synthesis

Chemical Properties

Clear Colourless Liquid

Uses

Chloromethyl Isopropyl Carbonate is an antiviral agent and a Tenofovir (T018500) intermediate. Tenofovir is an acyclic phosphonate nucleotide analogue and reverse transcriptase inhibitor used as an anti-HIV agent.

Synthesis

At 0-5°C, a photoinitiator is added, and dimethyl carbonate and chlorine are subjected to light reaction. The reaction is stopped, and the product is distilled and separated to obtain dimethyl monochlorocarbonate. At 70-100°C, a catalyst is added, and dimethyl monochlorocarbonate and isopropanol are added to a distillation tower capable of controlling the reflux ratio. Methanol is distilled and separated under normal pressure while reacting. After the reaction is completed, excess isopropanol is distilled off under reduced pressure, and finally chloromethyl isopropyl carbonate is distilled under reduced pressure.

References

[1] Tetrahedron, 2011, vol. 67, # 29, p. 5319 - 5328
[2] Patent: JP2015/164934, 2015, A. Location in patent: Paragraph 0195
[3] Journal of Medicinal Chemistry, 2009, vol. 52, # 3, p. 771 - 778
[4] Patent: WO2004/92189, 2004, A1. Location in patent: Page 29
[5] Journal of Medicinal Chemistry, 2015, vol. 58, # 23, p. 9133 - 9153

Chloromethyl isopropyl carbonate(35180-01-9)Related Product Information

• Chloromethyl ethyl carbonate
• Diethyl (tosyloxy)methylphosphonate
• Tenofovir
• Fluorobenzene
• Sodium metabisulfite
• Quinolinic acid
• Chloromethyl chlorosulfate
• Chloromethyl isobutyrate
• (S)-Metolachlor
• N2-ISOBUTYRYL-2'-DEOXYGUANOSINE
• 2-Hydroxypropyl methacrylate
• Allyl methacrylate
• Isopropyl chloroformate
• Diisopropyl peroxydicarbonate
• Triphosgene
• rac-Tenofovir-d7
• ChloroMethyl Propyl Carbonate
• Propylene carbonate