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Key Documents

T61301

Sigma-Aldrich

Triethyl phosphonoacetate

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:
Molecular Weight:
224.19
Beilstein:
1343714
EC Number:
MDL number:
UNSPSC Code:
12352108
PubChem Substance ID:
NACRES:
NA.22
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Quality Level

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

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Application

Horner-Emmons-Wadsworth reagent recently used in the synthesis of chiral 2-methylcyclopropanecarboxylic acid from (S)-propylene oxide.[1]
Reactant involved in:
  • Horner-Wadsworth-Emmons reactions
  • Intramolecular Heck-type cyclization and isomerizations
  • Tsuji-Trost type reactions
  • Intramolecular aryne-ene reactions
  • Synthesis of aldehydes

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

Eye Irrit. 2

Storage Class Code

10 - Combustible liquids

WGK

WGK 2

Flash Point(F)

221.0 °F - closed cup

Flash Point(C)

105 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

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

Questions

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  1. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer
    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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  2. How can I determine the shelf life / expiration / retest date of this product?

    1 answer
    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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