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D91071

Sigma-Aldrich

Diethyl benzylphosphonate

99%

Synonym(s):

(Diethoxyphosphonomethyl)benzene, Benzylphosphonic acid diethyl ester, NSC 62294

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About This Item

Linear Formula:
C6H5CH2P(O)(OC2H5)2
CAS Number:
1080-32-6
Molecular Weight:
228.22
EC Number:
214-097-4
MDL number:
MFCD00009078
UNSPSC Code:
12352108
PubChem Substance ID:
24894251
NACRES:
NA.22

Assay

99%

form

liquid

reaction suitability

reaction type: C-C Bond Formation

refractive index

n20/D 1.497 (lit.)

bp

106-108 °C/1 mmHg (lit.)

density

1.095 g/mL at 25 °C (lit.)

SMILES string

CCOP(=O)(Cc1ccccc1)OCC

InChI

1S/C11H17O3P/c1-3-13-15(12,14-4-2)10-11-8-6-5-7-9-11/h5-9H,3-4,10H2,1-2H3

InChI key

AIPRAPZUGUTQKX-UHFFFAOYSA-N

Application

Reactant for synthesis of:
  • 3,5-dihydroxy-4-isopropylstilbene for treatment of skin disorders
  • Natural cytotoxic marine products of polyketide origin via intramolecular Diels-Alder reactions
  • Stilbenes via on-column oxidation of vicinal diols and Horner-Emmons reactions
  • Inhibitors of teh Wnt pathway for colon cancer repression using Wadsworth-Emmons reactions
  • Antimalarial drug analogs against P. falciparum

Reactant for:
  • Cyclization of aryl ethers, amines, and amides
  • Investigating the effects of functional groups on the performance of clue organic LEDs

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Ananya Thomas et al.
Polymers, 12(8) (2020-08-17)
As a part of our ongoing investigations on passively fire protecting polymeric materials, we have been employing both reactive and additive routes involving phosphorus-containing compounds. These included inorganic and organic substances, and in the latter case, the phosphorus-bearing groups differed
Jack Saltiel et al.
Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology, 18(9), 2174-2179 (2019-05-28)
cis,trans-1,2-Dideuterio-1,4-diphenyl-1,3-butadiene (ct-DPBd2) was synthesized and its cis-trans photoisomerization in cyclohexane-d12 (C6D12) at room temperature was monitored by 1H NMR spectroscopy. The results reveal formation of only trans,trans-1,2-dideuterio-1,4-diphenyl-1,3-butadiene (tt-DPBd2). The failure to detect formation of trans,cis-1,2-dideuterio-1,4-diphenyl-1,3-butadiene (tc-DPBd2) eliminates the possibility that

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