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4-Cloromethyl-5-methyl-1,3-dioxol-2-one

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4-Cloromethyl-5-methyl-1,3-dioxol-2-one Basic information

Product Name:
4-Cloromethyl-5-methyl-1,3-dioxol-2-one
Synonyms:
  • DMDO-CL
  • 4-Cloromethyl-5-methyl-1,3-dioxol-2-one
  • Olmesartan Impurity 57
  • 4-CloroMethyl-5-Methyl-1,3-dioxol-2-one (DMDO-Cl)
  • OlMesartan IMpurity (4-(ChloroMethyl)-5-Methyl-1,3-Dioxol-2-one)
  • 4- chloroMethyl-5- Methyl-1,3- two oxygenheterocyclicpentadiene-2- ketone
  • -5--1,3- two4-chloroMethylMethylcyclopentene-2- ketoneheterocyclic oxygen
  • 4-ChloroMethyl-5-Methyl-l,3-dioxocyclopenten-2–one
CAS:
80841-78-7
MF:
C5H5ClO3
MW:
148.54
EINECS:
617-178-6
Product Categories:
  • Carbonates
  • Carbonyl Compounds
  • Chemical intermediate for Olmesartane
  • INTERMEDIATESOF
  • Organic Building Blocks
  • Pharmaceutical Intermediates
Mol File:
80841-78-7.mol
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4-Cloromethyl-5-methyl-1,3-dioxol-2-one Chemical Properties

Boiling point:
>90℃/2mm
Density 
1.362±0.06 g/cm3(Predicted)
refractive index 
1.4760-1.4820
Flash point:
129 °C
storage temp. 
Keep in dark place,Sealed in dry,Room Temperature
solubility 
Chloroform (Slightly), Methanol (Slightly)
form 
liquid
color 
Colorless to Light yellow to Light orange
Specific Gravity
1.36
BRN 
4798926
InChI
InChI=1S/C5H5ClO3/c1-3-4(2-6)9-5(7)8-3/h2H2,1H3
InChIKey
QCLFSYYUWPUWQR-UHFFFAOYSA-N
SMILES
CC1=C(OC(=O)O1)CCl
CAS DataBase Reference
80841-78-7(CAS DataBase Reference)
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Safety Information

Hazard Codes 
Xn
Risk Statements 
22-36/37/38
Safety Statements 
26
WGK Germany 
3
HS Code 
29329990
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4-Cloromethyl-5-methyl-1,3-dioxol-2-one Usage And Synthesis

Description

4-Chloromethyl-5-methyl-1,3-dioxol-2-one is a useful branch side chain for synthetic penicillin esters such as Lenampicillin, Mecillinam, etc. It can improve the stability and absorption of drugs, increase biological activity, and reduce side effects. It is also used to prepare amine drugs, such as Norfloxacin prodrug. In the prior art, the primary method for synthesizing 4-(Hydroxymethyl)-5-methyl-1,3-dioxol-2-one is a chlorination reaction of chlorine gas or N-chlorosuccinimide. 

Chemical Properties

Colorless to Light yellow to Light orange clear liquid or Pale Yellow Oil.

Uses

4-Chloromethyl-5-methyl-1,3-dioxol-2-one is an important reagent in the preparation of angiotensin II receptor antagonist such as Olmesratan Medoxomil (O550000). It is also used in the preparation of prodrugs of ampicillin.

Preparation

4,5-dimethyl-1,3-dioxole-2-ketone (DMDO) is used as raw material, taking sulfonic acid chloride as a chlorinating agent. The reaction is reat under the effect of a catalyzer in organic solvent and reacts for 1-5 hours to obtain target product 4-Cloromethyl-5-methyl-1,3-dioxol-2-one.

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