T61204

Sigma-Aldrich

Triethyl phosphite

98%

Synonym(s):
P(EtO)3, P(OEt)3
Linear Formula:
(C2H5O)3P
CAS Number:
Molecular Weight:
166.16
Beilstein/REAXYS Number:
956578
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

98%

reaction suitability

reagent type: ligand
reaction type: Reductions

impurities

≤1% triethyl phosphate and diethyl phosphite

refractive index

n20/D 1.413 (lit.)

bp

156 °C (lit.)

density

0.969 g/mL at 25 °C (lit.)

functional group

phosphine

SMILES string

CCOP(OCC)OCC

InChI

1S/C6H15O3P/c1-4-7-10(8-5-2)9-6-3/h4-6H2,1-3H3

InChI key

BDZBKCUKTQZUTL-UHFFFAOYSA-N

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Packaging

4 L in glass bottle
5, 100, 500 mL in glass bottle

Application

Used as a reducing agent; can react with electrophiles to form phosphonates or phosphates; forms a stable complex with copper(I) iodide.

pictograms

FlameExclamation mark

signalword

Warning

hazcat

Acute Tox. 4 Oral - Aquatic Chronic 3 - Flam. Liq. 3 - Skin Sens. 1B

storage_class_code

3 - Flammable liquids

WGK Germany

WGK 2

Flash Point F

129.2 °F - closed cup

Flash Point C

54 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Certificate of Analysis

Certificate of Origin

Misner, J. W.; Fisher, J. W. et al.
Tetrahedron Letters, 44, 5991-5991 (2003)
A Useful Synthesis of 1-Aminocyclopropanephosphonic Acid from Cyclopropanone Acetal.
Antoine Fadel
The Journal of organic chemistry, 64(13), 4953-4955 (2001-10-25)
Kyriacos Agapiou et al.
Journal of the American Chemical Society, 126(14), 4528-4529 (2004-04-09)
Exposure of enone substrates 1a-18a, which possess appendant ketone, ester, and nitrile moieties, to Et2Zn in the presence of catalytic Cu(OTf)2/P(OEt)3 provides the cyclized products in good to excellent yields and diastereoselectivities. These results represent the first use of ketones...
Amedjkouh, M.; Westerlund, K.
Tetrahedron Letters, 45, 5175-5175 (2004)
Victoria I Bunik et al.
Biochemistry, 44(31), 10552-10561 (2005-08-03)
The alpha-ketoglutarate dehydrogenase complex (KGDHC), a control point of the tricarboxylic acid cycle, is partially inactivated in brain in many neurodegenerative diseases. Potent and specific KGDHC inhibitors are needed to probe how the reduced KGDHC activity alters brain function. Previous...

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