D99234

Sigma-Aldrich

Diethyl phosphite

98%

Linear Formula:
(C2H5O)2P(O)H
CAS Number:
Molecular Weight:
138.10
Beilstein/REAXYS Number:
605759
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

98%

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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Application

Applications of diethyl phosphite (DEP):
  • It can undergo condensation with aldehydes or ketones and an amine to form α-aminophosphonates under solvent-free and catalyst-free conditions.
  • Reduction of gem-dibromo derivatives using diethyl phosphite in the presence of triethylamine gives monobromocyclopropanes.
  • Along with 4-dimethylaminopyridine, it can be used as a ligand for nickel-catalyzed cross-coupling of aryl and heteroaryl bromides, chlorides or sulfonates with arylzinc reagents.
  • It can be used for the catalytic asymmetric hydrophosphonylation of enones in the presence of a dinuclear zinc complex to form γ-oxo-phosphonates.
  • DEP can undergo Michael addition to α,β-unsaturated malonates to form β-phosphonomalonates in the presence of recyclable nano γ-ferric oxide-pyridine based catalyst.

Packaging

250 g in glass bottle

Pictograms

CorrosionExclamation mark

Signal Word

Danger

Hazard Statements

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

NONH for all modes of transport

WGK Germany

WGK 1

Highly Enantioselective 1,4?Addition of Diethyl Phosphite to Enones Using a Dinuclear Zn Catalyst.
Zhao D, et al.
Chemistry?A European Journal , 15(12), 2738-2741 (2009)
An efficient Negishi cross-coupling reaction catalyzed by nickel (II) and diethyl phosphite.
Gavryushin A, et al.
Tetrahedron, 62(32), 7521-7533 (2006)
Reduction of gem-dibromides with diethyl phosphite.
Hirao T, et al.
The Journal of Organic Chemistry, 46(18), 3745-3747 (1981)
A simple and green procedure for the synthesis of α-aminophosphonate by a one-pot three-component condensation of carbonyl compound, amine and diethyl phosphite without solvent and catalyst.
Ranu B C and Hajra A
Green Chemistry, 4(6), 551-554 (2002)
Phospha-michael addition of diethyl phosphite to α,β-unsaturated malonates catalyzed by nano γ-Fe2O3-pyridine based catalyst as a new magnetically recyclable heterogeneous organic base.
Sobhani S, et al.
Applied Catalysis A: General, 454, 145-151 (2013)

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