Chloromethyl pivalate Chemical Properties

Melting point:

<-40°C

Boiling point:

146-148 °C (lit.)

Density 

1.045 g/mL at 25 °C (lit.)

refractive index 

n20/D 1.417(lit.)

Flash point:

104 °F

storage temp. 

Inert atmosphere,2-8°C

solubility 

Chloroform (Slightly), Ethyl Acetate (Sparingly)

form 

Liquid

Specific Gravity

1.038

color 

Clear colorless to slightly yellow

Water Solubility 

Miscible with most organic solvents. Immiscible with water.

BRN 

1560838

InChIKey

GGRHYQCXXYLUTL-UHFFFAOYSA-N

CAS DataBase Reference

18997-19-8(CAS DataBase Reference)

NIST Chemistry Reference

Propanoic acid, 2,2-dimethyl-, chloromethyl ester(18997-19-8)

EPA Substance Registry System

Propanoic acid, 2,2-dimethyl-, chloromethyl ester (18997-19-8)

Safety Information

Hazard Codes 

Xn,Xi

Risk Statements 

10-20/21/22-36/37/38

Safety Statements 

16-26-36-41-36/37/39

RIDADR 

UN 3272 3/PG 3

WGK Germany 

3

TSCA 

Yes

HazardClass 

3

PackingGroup 

III

HS Code 

29159000

MSDS

• Language:English Provider:2,2-Dimethylpropanoic acid chloromethyl ester
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

Chloromethyl pivalate Usage And Synthesis

Chemical Properties

Clear colorless to slightly yellow liquid

Uses

Chloromethyl pivalate was used in the synthesis of pivaloyloxy methyl ester of ofloxacin as prodrug. It was used as the reagent during the synthesis of an isoindoline-annulated, tricyclic sultam library via microwave-assisted, continuous-flow organic synthesis.

Application

Chloromethyl pivalate is a pharmaceutical intermediate compound used in the synthesis of active pharmaceutical ingredients. It is also involved in the acylation reaction with 9-(2-phosphonomethoxyethyl)adenine. It is used as a protecting agent for the N-protection of amines. It is also used in the preparation of thivaloyloxymethyl ester of ofloxacin as a prodrug. It is also used in the preparation of sulbactam pivoxil by reaction with the sodium salt of sulbactam. Besides, it is used as a reagent in the synthesis of isoindoline cyclic and continuous flow organic synthesis.

General Description

Chloromethyl pivalate reacts with sodium salt of sulbactam to yield sulbactam pivoxil. It undergoes acylation reaction with 9-(2-phosphonylmethoxyethyl)adenine (PMEA) to yield bis(pivaloyloxymethyl) PMEA.

Synthesis

Chloromethyl pivalate is prepared by the reaction of formaldehyd and pivaloyl chloride. The specific synthesis steps are as follows:
A mixture of pivaloyl chloride (8.56 g, 71 mmol), paraformaldehyde (2.13 g, 71 mmol) and zinc chloride (75 mg, 0.55 mmol) was stirred at 80 °C for 2 h. Purification by vacuum distillation afforded chloromethyl pivalate (41) as a colourless oil (6.29 g, 44.7 mmol, 59%). bp 80 °C/15 mmHg [lit.1 bp 80-81 °C/15 mmHg]; 1H NMR (400 MHz, CDCl3) δ 1.24 (9H, s, tBu), 5.72 (2H, s, CH2).

Chloromethyl pivalate(18997-19-8)Related Product Information

• DIMETHYLTHEXYLSILYL CHLORIDE
• 2-Chloro-2-methylpropane
• Methyl propionate
• Oxalyl chloride
• Methyl methacrylate
• Beclomethasone dipropionate
• Methyl chloroacetate
• tert-Butyldimethylsilyl chloride
• Methyl trimethylacetate
• Choline chloride
• Zinc chloride
• Calcium chloride
• Tris(trimethylsilyl)phosphate
• Chloromethyl butyrate
• Sodium chloride
• METHYL VALERATE
• BUTYL OLEATE
• Clobetasol propionate