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593095

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

Signal Word

Warning

Hazard Statements

H319

Precautionary Statements

P305 + P351 + P338

Hazard Classifications

Eye Irrit. 2

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

>230.0 °F - closed cup

Flash Point(C)

> 110 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

593095-BULK:
593095-1G:
593095-VAR:

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Certificates of Analysis (COA)

Lot/Batch Number
18431CB

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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)
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
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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