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Sigma-Aldrich

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
MDL number:
MFCD05664300
UNSPSC Code:
12352108
PubChem Substance ID:
24881330
NACRES:
NA.22

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_germany

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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Certificates of Analysis (COA)

Lot/Batch Number
18431CB

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I N Smirnova et al.
The journal of physical chemistry. B, 114(50), 16936-16947 (2010-12-01)
The high brilliance of the AILES beamline at the SOLEIL synchrotron facility has been exploited for the study of the gas-phase vibrational spectra of weakly volatile organophosphorous compounds. The propagation of the synchrotron radiation in long path length gas cells
Carbodiimides-key mediators in the synthesis of novel cytotoxic and analgesic/antiinflammatory motifs based on a-amino-, enaminophosphonates, and azaphosphones.
Abdou WM, et al.
Royal Society of Chemistry Advances, 3(5), 1528-1540 (2013)
Keisuke Nishikawa et al.
Organic letters, 12(5), 904-907 (2010-02-06)
The first enantioselective total synthesis of 10-isocyano-4-cadinene, a marine sesquiterpene isolated from nudibranchs of the family Phyllidiidae, was achieved. The cadinene is expected to be a novel nontoxic antifouling agent. In the synthesis, an intermolecular Diels-Alder reaction and a SmI(2)-induced
Lee et al.
The Journal of organic chemistry, 65(13), 4175-4178 (2000-06-24)
Treatment of allylic and vinylic phosphonates with excess LiHMDS, followed by addition of chlorotrimethylsilane, afforded alpha- and gamma- silylated allylic phosphonate mixtures. Without separation, these mixtures underwent the Friedel-Crafts reaction and base-promoted isomerization to give 4-oxo-2-alkenylphosphonates, which can serve as
(-)-Sparteine-mediated stereoselective intramolecular conjugate addition reactions of dienes and enynes
Oestreich M and Hoppe D
Tetrahedron Letters, 40(10), 1881-1884 (1999)

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