Trimethyl phosphonoacetate

Synonym(s):(Carboxymethyl)phosphonic acid trimethyl ester;NSC 84262

CAS NO.：5927-18-4
Empirical Formula: C5H11O5P
Molecular Weight: 182.11
MDL number: MFCD00008452
EINECS: 227-663-0
SAFETY DATA SHEET (SDS)
Update Date: 2025-12-02 15:15:01

What is Trimethyl phosphonoacetate?

Chemical properties

clear colorless to light yellow liquid

The Uses of Trimethyl phosphonoacetate

Trimethyl phosphonoacetate is used in the preparation of sarin A by intramolecular Mannich-type reactions. It is involved in the Horner-Wadsworth-Emmons olefination with aldehydes and ketones to give acrylic esters. It is also involved in oxa-Michael reactions, prenylation of oxindoles and heterocyclization reactions.

What are the applications of Application

Trimethyl phosphonoacetate is an important Wittig-horner reagent, which can be used to manufacture important intermediates of natural compounds such as vitamins, drugs, insect pheromones, etc.
Reactant involved in:
Intramolecular Mannich-type reactions to produce the sarain A diazatricyclic core
Organocatalytic oxa-Michael reactions
Prenylation and geranylation of oxindoles
Intramolecular Horner-Wadsworth-Emmons reactions
Olefin cross-metathesis / heterocyclization

Definition

ChEBI: Trimethyl phosphonoacetate is a phosphonic ester.

Properties of Trimethyl phosphonoacetate

Melting point:	242 °C
Boiling point:	118 °C0.85 mm Hg(lit.)
Density	1.125 g/mL at 25 °C(lit.)
refractive index	n20/D 1.437(lit.)
Flash point:	>230 °F
storage temp.	Keep in dark place,Sealed in dry,Room Temperature
form	Liquid
color	Clear colorless to light yellow
Specific Gravity	approximate 1.265ｇ/ml (20℃)
Water Solubility	Slightly miscible with water.
BRN	1865177
CAS DataBase Reference	5927-18-4(CAS DataBase Reference)
NIST Chemistry Reference	Trimethyl phosphonoacetate(5927-18-4)
EPA Substance Registry System	Acetic acid, (dimethoxyphosphinyl)-, methyl ester (5927-18-4)

Safety information for Trimethyl phosphonoacetate

Signal word	Warning
Pictogram(s)	Exclamation Mark Irritant GHS07
GHS Hazard Statements	H227:Flammable liquids H315:Skin corrosion/irritation H319:Serious eye damage/eye irritation H335:Specific target organ toxicity, single exposure;Respiratory tract irritation
Precautionary Statement Codes	P261:Avoid breathing dust/fume/gas/mist/vapours/spray. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing. P405:Store locked up.