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T61204

Sigma-Aldrich

Triethyl phosphite

98%

Synonym(s):

P(EtO)3, P(OEt)3

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About This Item

Linear Formula:
(C2H5O)3P
CAS Number:
122-52-1
Molecular Weight:
166.16
Beilstein:
956578
EC Number:
204-552-5
MDL number:
MFCD00009084
UNSPSC Code:
12352108
PubChem Substance ID:
24900347
NACRES:
NA.22

Quality Level

200

Assay

98%

reaction suitability

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.)

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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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
GHS02,GHS07

Signal Word

Warning

Hazard Statements

H226,H302,H317,H412

Hazard Classifications

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

Storage Class Code

3 - Flammable liquids

WGK

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

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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Misner, J. W.; Fisher, J. W. et al.
Tetrahedron Letters, 44, 5991-5991 (2003)
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
A Useful Synthesis of 1-Aminocyclopropanephosphonic Acid from Cyclopropanone Acetal.
Antoine Fadel
The Journal of organic chemistry, 64(13), 4953-4955 (2001-10-25)
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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