(1-Diazo-2-oxopropyl)phosphonic Acid Dimethyl Ester - ≥96%(HPLC) , CAS No.90965-06-3

CAS: 90965-06-3 Cat. No.: O131559 Molecular Weight: 192.11 Beilstein Registry Number: 4247670 EC Number: 692-521-0

GRADE & PURITY ≥96%(HPLC)

Synonyms

.ALPHA.-AZIDO-.ALPHA.-(DIMETHYL PHOSPHONO)ACETONE | 1-Diazoacetonylphosphonic Acid Dimethyl Ester | AM85386 | Bestmann reagent | DIMETHYL (ACETYLDIAZOMETHYL)PHOSPHONATE | OHIRA-BESTMANN REAGENT | Ohira-bestmann phosphonate | (1-Diazo-2-oxopropyl)phosphoni

Storage

Store at 2-8°C,Argon charged

Shipped In

Wet ice

Overview

Dimethyl (1-diazo-2-oxopropyl)phosphonate can be used as a reagent for the synthesis of:
Ethynyl compounds (alkynes) from aldehydes.
Isoquinoline and pyridine N-oxides by cyclization with oximes in the presence of Rh catalyst.
Dimethyl(diazomethyl)phosphonate through methanolysis, which is further employed as a reagent in the synthesis of enol ethers or alkynes.
Five-member heterocyclic scaffolds of pyrazoles, triazoles, and oxazoles via cycloaddition reaction and multicomponent reaction.

Specifications

Synonyms

.ALPHA.-AZIDO-.ALPHA.-(DIMETHYL PHOSPHONO)ACETONE | 1-Diazoacetonylphosphonic Acid Dimethyl Ester | AM85386 | Bestmann reagent | DIMETHYL (ACETYLDIAZOMETHYL)PHOSPHONATE | OHIRA-BESTMANN REAGENT | Ohira-bestmann phosphonate | (1-Diazo-2-oxopropyl)phosphoni

Specifications & Purity

≥96%(HPLC)

Storage

Store at 2-8°C, Argon charged

Shipped In

Wet ice

This product requires cold chain shipping. Ground and other economy services are not available.

Purity

≥96%(HPLC)

Names and Identifiers

• Pubchem Sid: 504771197
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504771197
• Canonical Smiles: CC(=O)C(=[N+]=[N-])P(=O)(OC)OC
• IUPAC Name: 1-diazo-1-dimethoxyphosphorylpropan-2-one
• InChIKey: SQHSJJGGWYIFCD-UHFFFAOYSA-N
• INCHI: 1S/C5H9N2O4P/c1-4(8)5(7-6)12(9,10-2)11-3/h1-3H3
• Isomeric SMILES: CC(=O)C(=[N+]=[N-])P(=O)(OC)OC
• WGK Germany: 3
• Molecular Weight: 192.11
• Beilstein: 4247670
• Reaxy-Rn: 4247670
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=4247670&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic acids and derivatives
    • Class Organic phosphonic acids and derivatives
      • Subclass Phosphonic acid diesters

• Kingdom: Organic compounds
• Superclass: Organic acids and derivatives
• Class: Organic phosphonic acids and derivatives
• Subclass: Phosphonic acid diesters
• Intermediate Tree Nodes: Not available
• Direct Parent: Phosphonic acid diesters
• Alternative Parents: Phosphonic acid esters Organophosphorus compounds Organooxygen compounds Organonitrogen compounds Organic zwitterions Organic salts Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aliphatic acyclic compounds
• Substituents: Phosphonic acid diester - Phosphonic acid ester - Organic nitrogen compound - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Organic salt - Organic zwitterion - Organophosphorus compound - Organooxygen compound - Organonitrogen compound - Aliphatic acyclic compound
• Description: This compound belongs to the class of organic compounds known as phosphonic acid diesters. These are organophosphorus compounds containing a diester derivative of phosphonic acid, with the general structure ROP(=O)OR' (R,R' = organyl group).
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Chemical and Physical Properties

• Sensitivity: air sensitive ;heat sensitive
• Refractive Index: 1.48
• Flash Point(°F): 35.6 °F
• Flash Point(°C): 2 °C
• Molecular Weight: 192.110 g/mol
• XLogP3: -0.500
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 192.03 Da
• Monoisotopic Mass: 192.03 Da
• Topological Polar Surface Area: 54.600 Ų
• Heavy Atom Count: 12
• Formal Charge: 0
• Complexity: 273.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 1
• The total count of all stereochemical bonds: 1
• Covalently-Bonded Unit Count: 1