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79525

Sigma-Aldrich

Triethyl phosphonoacetate

purum, ≥97.0% (GC)

Synonym(s):

(Diethoxyphosphinyl)acetic acid ethyl ester, Diethyl ethoxycarbonylmethylphosphonate, NSC 13898, NSC 16128, Triethyl carboxymethylphosphonate

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About This Item

Linear Formula:
(C2H5O)2P(O)CH2CO2C2H5
CAS Number:
867-13-0
Molecular Weight:
224.19
Beilstein/REAXYS Number:
1343714
EC Number:
212-757-6
MDL number:
MFCD00009177
UNSPSC Code:
12352108
PubChem Substance ID:
329768474
NACRES:
NA.22

grade

purum

Quality Level

100

assay

≥97.0% (GC)

form

liquid

reaction suitability

reaction type: C-C Bond Formation

refractive index

n20/D 1.431 (lit.)
n20/D 1.432

bp

142-145 °C/9 mmHg (lit.)

density

1.13 g/mL at 25 °C (lit.)

SMILES string

CCOC(=O)CP(=O)(OCC)OCC

InChI

1S/C8H17O5P/c1-4-11-8(9)7-14(10,12-5-2)13-6-3/h4-7H2,1-3H3

InChI key

GGUBFICZYGKNTD-UHFFFAOYSA-N

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Related Categories

Application

Reactant involved in:
  • Horner-Wadsworth-Emmons reactions
  • Intramolecular Heck-type cyclization and isomerizations
  • Tsuji-Trost type reactions
  • Intramolecular aryne-ene reactions
  • Synthesis of aldehydes

Other Notes

A Horner-Wittig reagent, review; Improved procedure for the C2 homologation of esters to α,β-unsaturated esters; Synthesis of α-(hydroxymethyl)acrylate

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H319

Hazard Classifications

Eye Irrit. 2

wgk_germany

WGK 2

flash_point_f

221.0 °F

flash_point_c

105 °C

ppe

Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCCC2854
BCBS3111V
BCBH8888V
BCBF7005V
BCBC2014V

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J.M. Takacs et al.
Tetrahedron Letters, 27, 1257-1257 (1986)
T. Minami et al.
Synthesis, 333-333 (1991)
J. Villieras et al.
Organic Syntheses, 66, 220-220 (1988)
J. Boutagy et al.
Chemical Reviews, 74, 87-87 (1974)
M Rodriguez et al.
International journal of peptide and protein research, 39(3), 273-277 (1992-03-01)
Racemic "carba" pseudo-dipeptide units such as Gly-psi(CH2-CH2)-D,L-Xaa were obtained either through the Horner-Emmons condensation of N-tert.-butyloxycarbonyl-beta alaninal with the appropriate substituted triethyl phosphonacetate, or from commercially available 3-carbethoxy-2-piperidone.

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