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436178

Sigma-Aldrich

1-Ethylpiperidine hypophosphite

95%

Synonym(s):

1-Ethylpiperidinium phosphinate

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About This Item

Empirical Formula (Hill Notation):
C7H18NO2P
CAS Number:
145060-63-5
Molecular Weight:
179.20
MDL number:
MFCD00216621
UNSPSC Code:
12352100
PubChem Substance ID:
24867286
NACRES:
NA.22

assay

95%

form

solid

mp

40-43 °C (lit.)

storage temp.

2-8°C

SMILES string

OPO.CCN1CCCCC1

InChI

1S/C7H15N.H3O2P/c1-2-8-6-4-3-5-7-8;1-3-2/h2-7H2,1H3;1-3H

InChI key

BNCZSWZTYPTERM-UHFFFAOYSA-N

General description

1-Ethylpiperidine hypophosphite promotes the carbon-carbon bond forming radical reactions in both aqueous and organic media. EPHP plays an important role of a good chain carrier during the radical addition of gem-dihalocompounds to electron-deficient olefins. It has been reported as a suitable radical reducing agent for organic halides.

Application

1-Ethylpiperidine hypophosphite (EPHP) may be used in the following studies:
  • As water-soluble chain carrier for the efficient radical cyclization in water for various hydrophobic substrates.
  • In the main radical-cyclisation step for the synthesis of the phytotoxic metabolite alboatrin and its epimer.
  • Preparation of bifunctional pentafluorophenyl/2,4,6-trichlorophenyl sulfonates.
  • Chemoselective radical reduction of the iodine atom in 1-deoxy-1-halo-1-iodo-alditols.
Reagent for:
Synthesis of spiroketals via intramolecular iodoetherification
A facile radical cyclization diverted to a rearrangement-cyclization with base
Radical deoxygenation
Synthesis of allylic H-phosphinates

pictograms

FlameExclamation mark
GHS02,GHS07

signalword

Warning

Hazard Classifications

Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Acute Tox. 4 Oral - Eye Irrit. 2 - Flam. Sol. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

4.1B - Flammable solid hazardous materials

wgk_germany

WGK 3

flash_point_f

132.8 °F - closed cup

flash_point_c

56 °C - closed cup

ppe

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Hypophosphite mediated carbon-carbon bond formation: A clean approach to radical methodology.
Graham SR, et al.
Tetrahedron Letters, 40(!2), 2415-2416 (1999)
Tributyltin hydride and 1-ethylpiperidine hypophosphite mediated intermolecular radical additions to 2, 4, 6-trichlorophenyl vinyl sulfonate.
Edetanlen-Elliot O, et al.
Tetrahedron Letters, 48(50), 8926-8929 (2007)
Chemoselective 1-ethylpiperidine hypophosphite (EPHP)-mediated intermolecular radical additions of 1-deoxy-1-halo-1-iodo-alditols to electron-deficient olefins.
Francisco CG, et al.
Tetrahedron Letters, 47(51), 9057-9060 (2006)
Hypophosphite mediated carbon-carbon bond formation: total synthesis of epialboatrin and structural revision of alboatrin.
Graham SR, et al.
Journal of the Chemical Society. Perkin Transactions 1, 21, 3071-3073 (1999)
Stereoselective synthesis of trisubstituted tetrahydrofurans by radical cyclisation reaction using a hypophosphite salt. Application to the total synthesis of (?)-dihydrosesamin.
Roy SC, et al.
Tetrahedron, 58(12), 2435-2439 (2002)
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