D99234
Diethyl phosphite
98%
Synonym(s):
Diethoxyphosphine oxide, Diethyl acid phosphite, Diethyl hydrogen phosphite, Diethyl phosphonate, Hydrogen diethyl phosphite
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About This Item
Linear Formula:
(C2H5O)2P(O)H
CAS Number:
Molecular Weight:
138.10
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
EC Number:
212-091-6
Beilstein/REAXYS Number:
605759
MDL number:
Assay:
98%
Form:
liquid
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
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.
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wgk
WGK 1
signalword
Danger
hcodes
Hazard Classifications
Eye Dam. 1 - Skin Sens. 1B
Storage Class
10 - Combustible liquids
flash_point_f
179.6 °F - closed cup
flash_point_c
82 °C - closed cup
ppe
Eyeshields, Gloves, type ABEK (EN14387) respirator filter
Regulatory Information
监管及禁止进口产品
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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)
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)
Global Trade Item Number
| SKU | GTIN |
|---|---|
| D99234-250G | 04061833591369 |