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T79758

Sigma-Aldrich

Trimethyl phosphonoacetate

98%

Synonym(s):

(Carboxymethyl)phosphonic acid trimethyl ester, NSC 84262

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About This Item

Linear Formula:
(CH3O)2P(O)CH2CO2CH3
CAS Number:
5927-18-4
Molecular Weight:
182.11
Beilstein:
1865177
EC Number:
227-663-0
MDL number:
MFCD00008452
UNSPSC Code:
12352108
PubChem Substance ID:
24900489
NACRES:
NA.22

Assay

98%

reaction suitability

reaction type: C-C Bond Formation

refractive index

n20/D 1.437 (lit.)

bp

118 °C/0.85 mmHg (lit.)
265-268 °C (lit.)

density

1.125 g/mL at 25 °C (lit.)

SMILES string

COC(=O)CP(=O)(OC)OC

InChI

1S/C5H11O5P/c1-8-5(6)4-11(7,9-2)10-3/h4H2,1-3H3

InChI key

SIGOIUCRXKUEIG-UHFFFAOYSA-N

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Application

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

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

235.4 °F - closed cup

Flash Point(C)

113 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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B R DeMark et al.
Archives of biochemistry and biophysics, 223(2), 360-368 (1983-06-01)
The effects of the inhibitors trimethylacetyl phosphate and cAMP have been determined in reactions catalyzed by D-glyceraldehyde-3-phosphate dehydrogenase. These inhibitors must influence the oxidation of aldehydes through substrate dependent cooperative conformational changes. Both trimethylacetyl phosphate and cAMP give sigmoidal 1/V
Alastair B Ross et al.
The Journal of nutrition, 143(6), 766-773 (2013-04-26)
Epidemiological studies consistently find that diets rich in whole-grain (WG) cereals lead to decreased risk of disease compared with refined grain (RG)-based diets. Aside from a greater amount of fiber and micronutrients, possible mechanisms for why WGs may be beneficial

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