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640522

Sigma-Aldrich

Diethyl 3-butenylphosphonate

95%

Synonym(s):

P-3-Buten-1-yl-phosphonic acid diethyl ester

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About This Item

Linear Formula:
CH2=CHCH2CH2PO(OCH2CH3)2
CAS Number:
Molecular Weight:
192.19
MDL number:
UNSPSC Code:
12352108
PubChem Substance ID:
NACRES:
NA.22
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Assay

95%

reaction suitability

reaction type: C-C Bond Formation

bp

55 °C/0.55 mmHg (lit.)

density

1.005 g/mL at 25 °C (lit.)

functional group

allyl
phosphonate

SMILES string

CCOP(=O)(CCC=C)OCC

InChI

1S/C8H17O3P/c1-4-7-8-12(9,10-5-2)11-6-3/h4H,1,5-8H2,2-3H3

InChI key

NUDGAPYPOAQVLP-UHFFFAOYSA-N

Application

Reactant for synthesis of:
  • Bicyclo[3.3.1]alkenone framework compounds by gold-catalyzed Diels-Alder reactions
  • Antiviral C-5-substituted pyrimidine acyclic nucleoside phosphonates selected as human thymidylate kinase substrates
  • Antimalarials via halogenation of di-Et butenylphosphonate
  • Bisphosphonate enynes

Reactant for:
  • Remote supramolecular control of catalyst selectivity in hydroformlyation of alkenes
  • Intermolecular metal-catalyzed carbenoid cyclopropanations
  • Chemoenzymatic synthesis of phosphic derivatives of carbohydrates

Pictograms

Skull and crossbones

Signal Word

Danger

Hazard Statements

Hazard Classifications

Acute Tox. 3 Oral

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flash Point(F)

222.1 °F - closed cup

Flash Point(C)

105.6 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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