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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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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
Stowell, J. K.; Widlanski, T. S. et al.
Tetrahedron Letters, 36, 1825-1825 (1995)
Gabriele Albertin et al.
Dalton transactions (Cambridge, England : 2003), 44(35), 15470-15480 (2015-08-04)
Diazoalkane complexes [Ru(Tp)(N2CAr1Ar2)(PPh3)L]BPh4 ( and ) [Tp = tris(pyrazolyl)borate; L = P(OMe)3, P(OEt)3; Ar1 = Ar2 = Ph; Ar1 = Ph, Ar2 = p-tolyl; Ar1Ar2 = C12H8] were prepared by allowing chloro-compounds RuCl(Tp)(PPh3)L to react with diazoalkane in the presence
Misner, J. W.; Fisher, J. W. et al.
Tetrahedron Letters, 44, 5991-5991 (2003)
Rocky J Barney et al.
The Journal of organic chemistry, 76(8), 2875-2879 (2011-03-17)
Benzyl phosphonate esters often serve as reagents in Horner-Wadsworth-Emmons reactions. In most cases, they can be prepared from benzylic alcohols via formation of the corresponding halide followed by an Arbuzov reaction. To identify a more direct synthesis of phosphonate esters
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