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Trimethyl phosphonoacetate

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Trimethyl phosphonoacetate Basic information

Product Name:
Trimethyl phosphonoacetate
Synonyms:
  • TriMethyl phosphonoacetate, 98% 25GR
  • Dimethylphosphonoacetic Acid Methyl Ester Methyl Dimethylphosphonoacetate Phosphonoacetic Acid Trimethyl Ester
  • TriMethyl phosphonoacetat
  • Aceticacid, 2-(diMethoxyphosphinyl)-, Methyl ester
  • Dibenzyloxyphosphoiyl three Methyl acetate
  • (Carboxymethyl)phosphonic acid trimethyl ester
  • Dimethyl methoxycarbonylmethylphosphonate~Phosphonoacetic acid trimethyl ester
  • TMPA
CAS:
5927-18-4
MF:
C5H11O5P
MW:
182.11
EINECS:
227-663-0
Product Categories:
  • Horner-Emmons Reaction
  • Synthetic Organic Chemistry
  • Wittig & Horner-Emmons Reaction
  • C-C Bond Formation
  • Horner-Wadsworth-Emmons Reagents
  • Olefination
  • 5927-18-4
Mol File:
5927-18-4.mol
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Trimethyl phosphonoacetate Chemical Properties

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
Specific Gravity
approximate 1.265g/ml (20℃)
color 
Clear colorless to light yellow
Water Solubility 
Slightly miscible with water.
BRN 
1865177
LogP
-0.680 (est)
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)
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Safety Information

Safety Statements 
23-24/25
WGK Germany 
3
9
TSCA 
Yes
HS Code 
29310095

MSDS

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Trimethyl phosphonoacetate Usage And Synthesis

Chemical Properties

clear colorless to light yellow liquid

Uses

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.

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.

Trimethyl phosphonoacetate Preparation Products And Raw materials

Preparation Products

Trimethyl phosphonoacetateSupplier

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