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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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100 ML
$110.00
500 ML
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About This Item

Linear Formula:
(C2H5O)2P(O)CH2CO2C2H5
CAS Number:
Molecular Weight:
224.19
Beilstein/REAXYS Number:
1343714
EC Number:
MDL number:
UNSPSC Code:
12352108
PubChem Substance ID:
NACRES:
NA.22

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grade

purum

Quality Level

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.)

functional group

ester
phosphonate

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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This Item
T61301T79758158763
assay

≥97.0% (GC)

assay

98%

assay

98%

assay

97%

reaction suitability

reaction type: C-C Bond Formation

reaction suitability

reaction type: C-C Bond Formation

reaction suitability

reaction type: C-C Bond Formation

reaction suitability

reaction type: C-C Bond Formation

Quality Level

100

Quality Level

200

Quality Level

200

Quality Level

100

density

1.13 g/mL at 25 °C (lit.)

density

1.13 g/mL at 25 °C (lit.)

density

1.125 g/mL at 25 °C (lit.)

density

1.145 g/mL at 25 °C (lit.)

bp

142-145 °C/9 mmHg (lit.)

bp

142-145 °C/9 mmHg (lit.)

bp

118 °C/0.85 mmHg (lit.), 265-268 °C (lit.)

bp

127-131 °C/9 mmHg (lit.)

form

liquid

form

-

form

-

form

-

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[1][2]; Improved procedure for the C2 homologation of esters to α,β-unsaturated esters[3]; Synthesis of α-(hydroxymethyl)acrylate[4]

pictograms

Exclamation mark

signalword

Warning

hcodes

Hazard Classifications

Eye Irrit. 2

Storage Class

10 - Combustible liquids

wgk_germany

WGK 2

flash_point_f

221.0 °F - closed cup

flash_point_c

105 °C - closed cup

ppe

Eyeshields, Gloves


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