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Merck
CN

349852

[3-(Ethoxycarbonyl)propyl]triphenylphosphonium bromide

97%

Synonym(s):

NSC 269919

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About This Item

Linear Formula:
C2H5O2C(CH2)3P(C6H5)3Br
CAS Number:
50479-11-3
Molecular Weight:
457.34
NACRES:
NA.22
PubChem Substance ID:
24861713
UNSPSC Code:
12352108
MDL number:
MFCD00274610
Assay:
97%
Form:
solid

Key Documents

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InChI

1S/C24H26O2P.BrH/c1-2-26-24(25)19-12-20-27(21-13-6-3-7-14-21,22-15-8-4-9-16-22)23-17-10-5-11-18-23;/h3-11,13-18H,2,12,19-20H2,1H3;1H/q+1;/p-1

SMILES string

[Br-].CCOC(=O)CCC[P+](c1ccccc1)(c2ccccc2)c3ccccc3

InChI key

JPZMNVPVVYVXAD-UHFFFAOYSA-M

assay

97%

Quality Level

100

form

solid

reaction suitability

reaction type: C-C Bond Formation

mp

165-167 °C (lit.)

functional group

ester, phosphine

Related Categories

Application

Reactant for:
  • Asymmetric synthesis of antihypercholesterolemic ezetimibe via Wittig reaction
  • Wittig reactions
[3-(Ethoxycarbonyl)propyl]triphenylphosphonium bromide can be used:
  • As a reactant in the synthesis of spirocyclic GPR119 agonists.
  • In the synthesis of cyclic acetal intermediate of azadirachtin, a terpenoid found in the neem tree Azadirachta indica.
  • To prepare a catechin metabolite named 5-(3,4,5-trihydroxyphenyl)valeric acid.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
STBF5134V
S42816
08405LN

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Synthetic studies of azadirachtin. Synthesis of the cyclic acetal intermediate in the naturally occurring form
Nishikimi Y, et al.
The Journal of Organic Chemistry, 54(14), 3354-3359 (1989)
Design and synthesis of novel and potent GPR119 agonists with a spirocyclic structure
Harada K, et al.
Bioorganic & medicinal chemistry letters, 28(7), 1228-1233 (2018)
Inhibitory activity of catechin metabolites produced by intestinal microbiota on proliferation of HeLa cells
Hara-Terawaki A, et al.
Biological & Pharmaceutical Bulletin, 40(8), 1331-1335 (2017)

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