All Photos(1)
Synonym(s):
Diethoxyphosphine oxide, Diethyl acid phosphite, Diethyl hydrogen phosphite, Diethyl phosphonate, Hydrogen diethyl phosphite
Linear Formula:
(C2H5O)2P(O)H
CAS Number:
Molecular Weight:
138.10
Beilstein:
605759
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22
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Quality Level
Assay
98%
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 the organophosphorus compound used as a phosphorylating agent in organic synthesis.
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.
Signal Word
Danger
Hazard Statements
Precautionary Statements
Hazard Classifications
Eye Dam. 1 - Skin Sens. 1B
WGK
WGK 1
Flash Point(F)
closed cup
Flash Point(C)
closed cup
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
Regulatory Information
监管及禁止进口产品
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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An efficient Negishi cross-coupling reaction catalyzed by nickel (II) and diethyl phosphite.
Gavryushin A, et al.
Tetrahedron, 62(32), 7521-7533 (2006)
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)
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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