Trimethyl phosphonoacetate
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
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
- InChI
- 1S/C5H11O5P/c1-8-5(6)4-11(7,9-2)10-3/h4H2,1-3H3
- InChIKey
- SIGOIUCRXKUEIG-UHFFFAOYSA-N
- SMILES
- COC(=O)CP(=O)(OC)OC
- 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)
MSDS
- Language:English Provider:(Dimethoxyphosphinyl)-acetic acid methyl ester
- Language:English Provider:SigmaAldrich
- Language:English Provider:ACROS
- Language:English Provider:ALFA
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.
reaction suitability
reaction type: C-C Bond Formation
Synthesis
The trimethyl phosphonoacetate is prepared from trimethyl phosphite and methyl chloroacetate through Michael Arbuzov rearrangement reaction. The synthetic method satisfies the chemical equations that CH2ClCOOH + CH3OH → CH5ClO2 + H2O, CH5ClO2 + C3H9O3P → C5H11O5P + CH3Cl.
Trimethyl phosphonoacetate Preparation Products And Raw materials
Preparation Products
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