Diethyl allylphosphonate

Name: Diethyl allylphosphonate
Brand: ALDRICH
Price: 94.5 USD

98%

Synonym(s):

2-Propenyl-phosphonic acid diethyl ester

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About This Item

Linear Formula:

CH₂=CHCH₂P(O)(OC₂H₅)₂

CAS Number:

1067-87-4

Molecular Weight:

178.17

MDL number:

MFCD00015134

UNSPSC Code:

12352108

PubChem Substance ID:

24880237

NACRES:

NA.22

Key Documents

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Quality Level

100

assay

98%

reaction suitability

reaction type: C-C Bond Formation

refractive index

n20/D 1.4340 (lit.)

bp

46 °C/0.35 mmHg (lit.)

bulk density

1.022 g/mL

functional group

phosphonate

SMILES string

CCOP(=O)(CC=C)OCC

InChI

1S/C7H15O3P/c1-4-7-11(8,9-5-2)10-6-3/h4H,1,5-7H2,2-3H3

InChI key

YPJHXRAHMUKXAE-UHFFFAOYSA-N

Related Categories

C-C Bond Forming Reagents

Chemical Synthesis

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1 of 4

This Item	D91705	411361	392626
Sigma-Aldrich 565415 Diethyl allylphosphonate	Sigma-Aldrich D91705 Diethyl cyanomethylphosphonate	Sigma-Aldrich 411361 Diethyl (bromodifluoromethyl)phosphonate	Sigma-Aldrich 392626 Diethyl (hydroxymethyl)phosphonate
assay 98%	assay 98%	assay 96%	assay -
Quality Level 100	Quality Level 100	Quality Level 100	Quality Level 100
reaction suitability reaction type: C-C Bond Formation	reaction suitability reaction type: C-C Bond Formation	reaction suitability reaction type: C-C Bond Formation	reaction suitability reaction type: C-C Bond Formation
refractive index n20/D 1.4340 (lit.)	refractive index n20/D 1.434 (lit.)	refractive index n20/D 1.417 (lit.)	refractive index n20/D 1.444 (lit.)
bp 46 °C/0.35 mmHg (lit.)	bp 101-102 °C/0.4 mmHg (lit.)	bp 40-41 °C/0.05 mmHg (lit.)	bp 124-126 °C/3 mmHg (lit.)
bulk density 1.022 g/mL	bulk density -	bulk density -	bulk density -

Application

Reactant for:

Copolymerization of phosphonated allyl monomers and maleic anhydride
Enantioselective synthesis of solamin type mono-THF acetogenins
RCM reaction yielding oxaphospholene and oxaphosphinene heterocycles
Synthesis of spongistatin 2 using Wittig coupling
Stereoselective synthesis of pentacyclic furanosteroids
Preparation of protected polyhydroxylated β -amino acid constitutents of microsclerodermins

pictograms

GHS07

signalword

Warning

hcodes

H315,H319,H335

pcodes

P261 - P264 - P271 - P280 - P302 + P352 - P305 + P351 + P338

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

10 - Combustible liquids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type ABEK (EN14387) respirator filter

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Fosmidomycin biosynthesis diverges from related phosphonate natural products.

Elizabeth I Parkinson et al.

Nature chemical biology, 15(11), 1049-1056 (2019-08-28)

Fosmidomycin and related molecules comprise a family of phosphonate natural products with potent antibacterial, antimalarial and herbicidal activities. To understand the biosynthesis of these compounds, we characterized the fosmidomycin producer, Streptomyces lavendulae, using biochemical and genetic approaches. We were unable

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