DIETHYL (CHLOROMETHYL)PHOSPHONATE Chemical Properties

Boiling point:

109-110 °C10 mm Hg(lit.)

Density 

1.2 g/mL at 25 °C(lit.)

refractive index 

n20/D 1.437(lit.)

Flash point:

188 °F

storage temp. 

2-8°C

solubility 

sol THF, ether, dichloromethane, chloroform

form 

Liquid

Specific Gravity

1.2

color 

Clear colorless to light yellow

BRN 

1363361

EPA Substance Registry System

Phosphonic acid, (chloromethyl)-, diethyl ester (3167-63-3)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

Hazard Note 

Irritant

HS Code 

29319090

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS

DIETHYL (CHLOROMETHYL)PHOSPHONATE Usage And Synthesis

Chemical Properties

Clear colorless to light yellow liquid

Uses

Reactant involved in:

• Subsequent alkylation after nucleophilic substitution
• One-pot alkylation-boration of α-haloalkylphosphonates
• Synthesis of cyclpentane and pyrrolidine derivatives via regioselective insertion reactions
• Phosphorylation leading to P-containing cyclopropanes
• Wadsworth-Emmons reactions
• Ring expansion of zircnacycles via carbenoid insertion

Synthesis Reference(s)

Tetrahedron Letters, 28, p. 3799, 1987 DOI: 10.1016/S0040-4039(00)96387-1

reaction suitability

reaction type: C-C Bond Formation

Synthesis

Diethyl (chloromethyl)phosphonate is synthesized by a preparative scale of (EtO)2P(O)CH2Cl and other (1- chloroalkyl)phosphonates is relatively difficult. Ethanolysis of (chloromethyl)phosphonic dichloride is the most general and useful procedure (eq 1).

DIETHYL (CHLOROMETHYL)PHOSPHONATE(3167-63-3)Related Product Information

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