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)

Safety Information

Hazard Codes 

Xn

Risk Statements 

22-36/37/38

Safety Statements 

26

WGK Germany 

3

HS Code 

29329990

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.

Synthesis

General procedure for the synthesis of 4-chloromethyl-5-methyl-1,3-dioxolan-2-one from 4,5-dimethyl-1,3-dioxolan-2-one: To a stirred solution of 4,5-dimethyl-1,3-dioxolan-2-one (DMDO) were added 4725 g of ethylene dichloride, 10.12.5 g of N-chlorosuccinimide (NCS) and 45 g of benzoyl peroxide (BPO), the reaction temperature was maintained at 90 °C, and the reaction lasted for 5.5 h. The crude product 4-chloromethyl-5-methyl-1,3-dioxolen-2-one (DMDO-Cl) was obtained as 382.5 g in 85.00% yield. Step 3: distillation: the crude product of DMDO-Cl was distilled under vacuum at -0.1 MPa at 110 °C to obtain 326 g of DMDO-Cl. Its purity was 99.06% as determined by gas chromatography (GC).

References

[1] Chemical and Pharmaceutical Bulletin, 1984, vol. 32, # 6, p. 2241 - 2248
[2] Chemical and Pharmaceutical Bulletin, 1988, vol. 36, # 1, p. 394 - 397
[3] Patent: US4554358, 1985, A
[4] Patent: CN107892681, 2018, A. Location in patent: Paragraph 0015-0022

4-Cloromethyl-5-methyl-1,3-dioxol-2-one(80841-78-7)Related Product Information

• 4-Methyl-2-pentanone
• Mesotrione
• Methyl cellulose
• Kresoxim-methyl
• Methylparaben
• Norgestrel
• Bensulfuron methyl
• METSULFURON METHYL
• Methyl acrylate
• 4,5-Dimethyl-1,3-dioxol-2-one
• 4-Bromomethyl-5-methyl-1,3-dioxol-2-one
• N-Methyl-2-pyrrolidone
• tert-Butyldimethylsilyl chloride
• Methanol
• Cyclopentene
• Olmesartan
• Olmesartan
• Methyl