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Merck
CN

348333

tert-Butyl diethylphosphonoacetate

95%

Synonym(s):

(Diethoxyphosphinyl)acetic acid 1,1-dimethylethyl ester, tert-Butyl (diethoxyphosphinyl)acetate, Diethyl tert-butoxycarbonylmethanephosphonate

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About This Item

Linear Formula:
(C2H5O)2P(O)CH2CO2C(CH3)3
CAS Number:
27784-76-5
Molecular Weight:
252.24
NACRES:
NA.22
PubChem Substance ID:
24861567
UNSPSC Code:
12352108
MDL number:
MFCD00075414

Key Documents

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Product Name

tert-Butyl diethylphosphonoacetate, 95%

InChI

1S/C10H21O5P/c1-6-13-16(12,14-7-2)8-9(11)15-10(3,4)5/h6-8H2,1-5H3

SMILES string

CCOP(=O)(CC(=O)OC(C)(C)C)OCC

InChI key

NFEGNISFSSLEGU-UHFFFAOYSA-N

assay

95%

form

liquid

reaction suitability

reaction type: C-C Bond Formation

refractive index

n20/D 1.431 (lit.)

bp

100-103 °C/1.5 mmHg (lit.)

density

1.074 g/mL at 25 °C (lit.)

functional group

ester
phosphonate

Application

Reactant for:
  • Preparation of ydroxymethylated dihydroxyvitamin D3 analogs via Wittig-Horner approach, as potential antitumor agents
  • Synthesis of phosphopeptide mimetic prodrugs targeted to Src homology 2 (SH2) domain of signal transducer and activator of transcription 3 (Stat 3)
  • One-pot synthesis of the DPP4-selective inhibitor ABT-341 by a four-component coupling mediated by a diphenylprolinol silyl ether
  • Bicyclic triaminophosphine-promoted stereoselective synthesis of a,ß-unsaturated esters, fluorides, and nitriles from aldehydes and ketones using Wadsworth-Emmons phosphonates
  • Preparation of amidopropenyl hydroxamates as human histone deacetylase (HDAC) inhibitors

Storage Class

10 - Combustible liquids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
MKBG7884V
MKBB6107
14331JH
07502KE
15117HC

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Yosuke Kato et al.
Rapid communications in mass spectrometry : RCM, 34(7), e8636-e8636 (2019-10-30)
Ferulic acid (FA) is a standard matrix used for analyzing proteins. In this study, the ability of a halogenated FA to serve as an effective MALDI matrix was investigated. Various halogenated FAs were synthesized, and the characteristics and performance of

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