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79527

Trimethyl phosphonoacetate

Name: Trimethyl phosphonoacetate
Brand: SIAL

purum, ≥98.0% (GC)

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

EC Number:

227-663-0

UNSPSC Code:

12352108

PubChem Substance ID:

329768475

Beilstein/REAXYS Number:

1865177

MDL number:

MFCD00008452

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Properties

grade

purum

assay

≥98.0% (GC)

reaction suitability

reaction type: C-C Bond Formation

refractive index

n20/D 1.437

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

Description

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

Other Notes

This product has been replaced by T79758-ALDRICH | Trimethyl phosphonoacetate 98%

Storage Class

10 - Combustible liquids

wgk

WGK 3

flash_point_f

235.4 °F - closed cup

flash_point_c

113 °C - closed cup

ppe

Eyeshields, Gloves, type ABEK (EN14387) respirator filter

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Acyl phosphate and cyclic AMP inhibition of reactions of D-glyceraldehyde-3-phosphate dehydrogenase with aldehyde and acyl phosphate substrates: multiple inhibition analysis.

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

A whole-grain-rich diet reduces urinary excretion of markers of protein catabolism and gut microbiota metabolism in healthy men after one week.

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