MilliporeSigma
All Photos(1)

561053

Sigma-Aldrich

Diethyl (2-oxobutyl)phosphonate

96%

Synonym(s):
Diethyl propanoylmethylphosphonate, (2-Oxobutyl)phosphonic acid diethyl ester
Linear Formula:
(C2H5O)2PCH2COCH2CH3
CAS Number:
Molecular Weight:
208.19
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

96%

reaction suitability

reaction type: C-C Bond Formation

refractive index

n20/D 1.4360 (lit.)

density

1.072 g/mL at 25 °C (lit.)

SMILES string

CCOP(=O)(CC(=O)CC)OCC

InChI

1S/C8H17O4P/c1-4-8(9)7-13(10,11-5-2)12-6-3/h4-7H2,1-3H3

InChI key

GQBVFZDYDHGZPY-UHFFFAOYSA-N

Application

Reactant for synthesis of:
  • Oxa(bicyclo)octanone for use in preparing cycloheptane annulated furans
  • Anatoxin-a and homoanatoxin via the Wittig reaction
  • α-Methylene-β-amino ketones
  • 2-Amino-5-phosphono- and 2-amino-4-(phosphonomethyl)thiophenes using the Gewald reaction
  • Aliphatic musk odorants
  • Oxoalkylphosphonates

Packaging

1, 5 mL in glass bottle

Storage Class Code

12 - Non Combustible Liquids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificate of Analysis

Enter Lot Number to search for Certificate of Analysis (COA).

Certificate of Origin

Enter Lot Number to search for Certificate of Origin (COO).

Nina V Fuchs et al.
Stem cell research, 41, 101592-101592 (2019-11-08)
The Renpenning syndrome spectrum is a rare X-linked mental retardation syndrome characterized by intellectual disability, microcephaly, low stature, lean body and hypogonadism. Mutations in the polyglutamine tract binding protein 1 (PQBP1) locus are causative for disease. Here, we describe the
Katharina Hutter et al.
Molecular cell, 78(5), 876-889 (2020-06-06)
Many microRNAs (miRNAs) are generated from primary transcripts containing multiple clustered stem-loop structures that are thought to be recognized and cleaved by the Microprocessor complex as independent units. Here, we uncover an unexpected mode of processing of the bicistronic miR-15a-16-1
Vera Chesnokova et al.
Endocrinology, 160(6), 1439-1447 (2019-04-20)
DNA damage occurs as a result of environmental insults and aging and, if unrepaired, may lead to chromosomal instability and tumorigenesis. Because GH suppresses ataxia-telangiectasia mutated kinase phosphorylation, decreases DNA repair, and increases DNA damage accumulation, we elucidated whether GH
Seung Wook Yang et al.
Molecular cell, 77(6), 1206-1221 (2020-01-26)
Alternative polyadenylation (APA) contributes to transcriptome complexity by generating mRNA isoforms with varying 3' UTR lengths. APA leading to 3' UTR shortening (3' US) is a common feature of most cancer cells; however, the molecular mechanisms are not understood. Here
Penelope Kroustallaki et al.
Cell reports, 28(7), 1690-1702 (2019-08-15)
Telomerase biogenesis is a complex process where several steps remain poorly understood. Single-strand-selective uracil-DNA glycosylase (SMUG1) associates with the DKC1-containing H/ACA ribonucleoprotein complex, which is essential for telomerase biogenesis. Herein, we show that SMUG1 interacts with the telomeric RNA component

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