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T61301

Triethyl phosphonoacetate

Name: Triethyl phosphonoacetate
Brand: ALDRICH

98%

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

UNSPSC Code:

12352108

NACRES:

NA.22

PubChem Substance ID:

24900348

EC Number:

212-757-6

Beilstein/REAXYS Number:

1343714

MDL number:

MFCD00009177

Assay:

98%

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Properties

Quality Level

200

assay

98%

reaction suitability

reaction type: C-C Bond Formation

refractive index

n20/D 1.431 (lit.)

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

Description

Application

Horner-Emmons-Wadsworth reagent recently used in the synthesis of chiral 2-methylcyclopropanecarboxylic acid from (S)-propylene oxide.

Reactant involved in:

Horner-Wadsworth-Emmons reactions
Intramolecular Heck-type cyclization and isomerizations
Tsuji-Trost type reactions
Intramolecular aryne-ene reactions
Synthesis of aldehydes

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pictograms

GHS07

signalword

Warning

hcodes

H319

pcodes

P264 - P280 - P305 + P351 + P338 - P337 + P313

Hazard Classifications

Eye Irrit. 2

Storage Class

10 - Combustible liquids

wgk

WGK 2

flash_point_f

221.0 °F - closed cup

flash_point_c

105 °C - closed cup

ppe

Eyeshields, Gloves, multi-purpose combination respirator cartridge (US)

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Organic Process Research & Development, 11, 689-689 (2007)

"Carba" peptide bond surrogates. Different approaches to Gly-psi(CH2-CH2)-D,L-Xaa pseudo-dipeptide units.

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.

Global Trade Item Number

SKU	GTIN
T61301-25G	04061833403679
T61301-100G	04061837358357