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365920

Sigma-Aldrich

Diethyl phosphite

technical grade, 94%

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About This Item

Linear Formula:
(C2H5O)2P(O)H
CAS Number:
762-04-9
Molecular Weight:
138.10
Beilstein:
605759
MDL number:
MFCD00044573
UNSPSC Code:
12352100
PubChem Substance ID:
24862594

grade

technical grade

Quality Level

200

Assay

94%

form

liquid

refractive index

n20/D 1.407 (lit.)

bp

50-51 °C/2 mmHg (lit.)

density

1.072 g/mL at 25 °C (lit.)

SMILES string

[H]P(=O)(OCC)OCC

InChI

1S/C4H11O3P/c1-3-6-8(5)7-4-2/h8H,3-4H2,1-2H3

InChI key

MJUJXFBTEFXVKU-UHFFFAOYSA-N

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General description

Diethyl phosphite is reported to be chemical warfare agent (CWA) simulant, simulant for nerve agents sarin, soman, tabun, and VX.

Application

Diethyl phosphite may be used to prepare the nickel chloride-diethyl phosphite system, efficient catalyst for the cross-coupling reaction between various functionalized arylzinc halides and aryl bromides, triflates and activated chlorides. It may be used:
  • in the stereoselective synthesis of β-fluorinated alkylphosphonates
  • in the synthesis of homoallylic bromide
  • in the synthesis of series of carbazole-based α-aminophosphonates

Pictograms

CorrosionExclamation mark
GHS05,GHS07

Signal Word

Danger

Hazard Statements

H317 - H318

Hazard Classifications

Eye Dam. 1 - Skin Sens. 1B

Storage Class Code

10 - Combustible liquids

WGK

WGK 2

Flash Point(F)

179.6 °F - closed cup

Flash Point(C)

82 °C - closed cup

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Wenke Qi et al.
The Journal of organic chemistry, 78(12), 5918-5924 (2013-05-22)
Cyclopropyl Grignard reagents react with carbonyl compounds in the presence of diethyl phosphite to give homoallylic bromides. The reaction is effectively carried out under mild conditions in a one-pot fashion with moderate to good yields.
Adam M Graichen et al.
Journal of the American Society for Mass Spectrometry, 24(6), 917-925 (2013-03-28)
The gas-phase reactions of a series of coordinatively unsaturated [Ni(L)n](y+) complexes, where L is a nitrogen-containing ligand, with chemical warfare agent (CWA) simulants in a miniature rectilinear ion trap mass spectrometer were investigated as part of a new approach to
Anil Kumar Mungara et al.
Chemical & pharmaceutical bulletin, 60(12), 1531-1537 (2012-09-19)
A novel series of carbazole-based α-aminophosphonates were synthesized by three component coupling of 6-bromo-9-ethyl-9H-carbazole-3-carbaldehyde, amine and diethyl phosphite using polyethylene glycol (PEG-400) as a green reaction media. The antiproliferative activity of these molecules was evaluated against three cancer cell lines.
Andrei Gavryushin et al.
Organic letters, 7(22), 4871-4874 (2005-10-21)
[reaction: see text] The combination of diethyl phosphite and DMAP as ligands for nickel in an 8:1 THF-N-ethylpyrrolidinone (NEP) mixture allows a very efficient cross-coupling reaction to be performed between various functionalized arylzinc halides and aryl bromides, triflates and activated
Chengwei Zhang et al.
Journal of the American Chemical Society, 135(38), 14082-14085 (2013-09-13)
We report herein a mild and catalytic phosphonofluorination of unactivated alkenes. With catalysis by AgNO3, the condensation of various unactivated alkenes with diethyl phosphite and Selectfluor reagent in CH2Cl2/H2O/HOAc at 40 °C led to the efficient synthesis of β-fluorinated alkylphosphonates

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