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593095

Diethyl (2-methylallyl)phosphonate

97%

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About This Item

Linear Formula:
(C2H5O)2POCH2C(=CH2)CH3
CAS Number:
51533-70-1
Molecular Weight:
192.19
NACRES:
NA.22
PubChem Substance ID:
24881330
UNSPSC Code:
12352108
MDL number:
MFCD05664300
Assay:
97%
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assay

97%

reaction suitability

reaction type: C-C Bond Formation

refractive index

n20/D 1.4380 (lit.)

bp

62 °C/0.1 mmHg (lit.)

density

1.013 g/mL at 25 °C (lit.)

functional group

phosphonate

SMILES string

CCOP(=O)(CC(C)=C)OCC

InChI

1S/C8H17O3P/c1-5-10-12(9,11-6-2)7-8(3)4/h3,5-7H2,1-2,4H3

InChI key

QOZGSMHGXZMADD-UHFFFAOYSA-N

General description

Diethyl (2-methylallyl)phosphonate is an organophosphorous compound. It participates in the synthesis of α-aminophosphonate derivatives and azaphosphones. The analgesic/antiinflammatory properties of these derivatives were evaluated.

Application

Diethyl (2-methylallyl)phosphonate can be used as a reagent in the Horner-Wadsworth-Emmons reaction to form conjugated carbon–carbon double bonds.
It can also be used as a reactant for:
  • Enantioselective total synthesis of 10-isocyano-4-cadinene as antifouling agent.
  • Regiospecific preparation of 4-oxo-2-alkenylphosphonates (OAP) via silylation followed by Friedel-Crafts acylation and isomerization. OAP can serve as building blocks for the construction of polyethylenic chains.
  • The synthesis of azaphosphone as a potent analgesic/anti-inflammatory agents.

Reactant for:
  • Enantioselective synthesis of 10-isocyano-4-cadinene and its stereoisomers with antifouling activity
  • Preparation of 4-Oxo-2-alkenylphosphonates via silylation followed by regiospecific Friedel-Crafts acylation and isomerization

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H319

Hazard Classifications

Eye Irrit. 2

Storage Class

10 - Combustible liquids

wgk

WGK 3

flash_point_f

>230.0 °F - closed cup

flash_point_c

> 110 °C - closed cup

ppe

Eyeshields, Gloves, type ABEK (EN14387) respirator filter

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