90965-06-3

Basic information

• Product Name: (1-DIAZO-2-OXO-PROPYL)-PHOSPHONIC ACID DIMETHYL ESTER
• Synonyms: DIMETHYL (1-DIAZO-2-OXOPROPYL)PHOSPHONATE;(1-DIAZO-2-OXO-PROPYL)-PHOSPHONIC ACID DIMETHYL ESTER;(1-DIAZO-2-OXO-PROPYL)-PHOSPHONIC ACID DIMETHYL ESTER BESTMANN OHIRA REAGENT;1-Diazoacetonylphosphonic Acid Dimethyl Ester;Dimethyl 1-Diazoacetonylphosphonate;Ohira-Bestmann reagent;diMethyl(1-diazo-2-oxopropyl)phosphanate;Phosphonic acid,P-(1-diazo-2-oxopropyl)-, diMethyl ester
• CAS NO: 90965-06-3
• Molecular Formula: C₅H₉N₂O₄P
• Molecular Weight: 192.11
• Mol File: 90965-06-3.mol
• Article Data: 96

Chemical Properties

• Flash Point: 2℃
• Appearance: /
• Density: 1.28
• Refractive Index: n20/D1.352-1.354
• Storage Temp.: 2-8°C
• Solubility: Chloroform, Methanol (Slightly)
• Merck: 14,1177
• BRN: 4247670
• CAS DataBase Reference: (1-DIAZO-2-OXO-PROPYL)-PHOSPHONIC ACID DIMETHYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: (1-DIAZO-2-OXO-PROPYL)-PHOSPHONIC ACID DIMETHYL ESTER(90965-06-3)
• EPA Substance Registry System: (1-DIAZO-2-OXO-PROPYL)-PHOSPHONIC ACID DIMETHYL ESTER(90965-06-3)

Safety Data

• Hazard Codes: F,Xn
• Statements: 11-20/21/22-36
• Safety Statements: 16-26-36/37
• RIDADR: UN 1648 3 / PGII
• WGK Germany: 3
• HazardClass: 3
• PackingGroup: II
• Hazardous Substances Data: 90965-06-3(Hazardous Substances Data)

Usage

Description

(1-DIAZO-2-OXO-PROPYL)-PHOSPHONIC ACID DIMETHYL ESTER, also known as Dimethyl (1-diazo-2-oxopropyl)phosphonate, is a light yellow liquid that serves as a versatile reagent in organic synthesis. It is known for its ability to transform aldehydes into terminal alkynes and ketones into methyl enol ethers, making it a valuable compound in various chemical reactions.

Uses

Used in Organic Synthesis:
(1-DIAZO-2-OXO-PROPYL)-PHOSPHONIC ACID DIMETHYL ESTER is used as a reagent for the transformation of aldehydes to terminal alkynes and ketones to methyl enol ethers, enabling the synthesis of a wide range of organic compounds.
Used in Ethynyl Compound Synthesis:
In the field of organic chemistry, (1-DIAZO-2-OXO-PROPYL)-PHOSPHONIC ACID DIMETHYL ESTER is used as a reagent for the synthesis of ethynyl compounds (alkynes) from aldehydes, which are important building blocks in the creation of various organic molecules.
Used in Isoquinoline and Pyridine N-Oxide Synthesis:
(1-DIAZO-2-OXO-PROPYL)-PHOSPHONIC ACID DIMETHYL ESTER is used as a cyclization agent with oximes in the presence of a Rh catalyst to synthesize isoquinoline and pyridine N-oxides, which are valuable compounds in pharmaceutical and chemical research.
Used in Dimethyl(diazomethyl)phosphonate Synthesis:
Through methanolysis, (1-DIAZO-2-OXO-PROPYL)-PHOSPHONIC ACID DIMETHYL ESTER can be converted into Dimethyl(diazomethyl)phosphonate, which is further employed as a reagent in the synthesis of enol ethers or alkynes, expanding its applications in organic synthesis.
Used in Heterocyclic Scaffold Synthesis:
(1-DIAZO-2-OXO-PROPYL)-PHOSPHONIC ACID DIMETHYL ESTER is used in the synthesis of five-membered heterocyclic scaffolds, such as pyrazoles, triazoles, and oxazoles, through cycloaddition reactions and multicomponent reactions, contributing to the development of novel heterocyclic compounds with potential applications in various fields.

InChI:InChI=1/C5H9N2O4P/c1-4(8)5(7-6)12(9,10-2)11-3/h1-3H3

Upstream product

• 4202-14-6 dimethyl (2-oxopropyl)phosphonate 
• 2158-14-7 4-acetamidobenzenesulfonyl azide 
• 941-55-9 4-toluenesulfonyl azide 

Downstream Products

• 4202-14-6 dimethyl (2-oxopropyl)phosphonate 
• 26530-60-9 trimethyl 2-phosphonopropionate 
• 2243-98-3 1-undecyne 
• 19096-89-0 methoxymethylenecyclohexane 
• 162107-48-4 tert-butyl (R)-4-ethynyl-2,2-dimethyloxazolidine-3-carboxylate 
• 189952-75-8 (S)-3-[2-(Benzyl-tert-butoxycarbonyl-amino)-ethyl]-2-ethyl-hex-5-ynoic acid methyl ester 
• 273944-71-1 (3S,4R,5R,6R,7R,8R)-8-benzoyloxy-6-diethylisopropylsilyloxy-4-hydroxy-3-methoxy-5,7-dimethylnon-1-yne 
• 302554-00-3 (2R,3S)-1-O-tritylhex-5-yne-1,2,3-triol 
• 56017-85-7 (S)-4-ethynyl-2,2-dimethyl-1,3-dioxolane 
• 339193-66-7 {1-[4-bromo-1-(toluene-4-sulfonyl)-1H-indol-3-ylmethyl]-prop-2-ynyl}-methyl-carbamic acid tert-butyl ester 
• 344315-35-1 C₄₁H₅₆O₆S₂Si 
• 67099-42-7 3,3-Dimethyl-5-benzyloxy-1-pentin 
• 143327-83-7 O-tert-butyl N-(S)-(5-methylhex-1-yn-3-yl)carbamate 
• 143327-79-1 ((S)-1-benzyl-2-prop-2-ynyl)carbamic acid t-butyl ester 

Relevant articles and documents

Unveiling novel 2-cyclopropyl-3-ethynyl-4-(4-fluorophenyl)quinolines as GPCR ligands via PI3-kinase/PAR-1 antagonism and platelet aggregation valuations; development of a new class of anticancer drugs with thrombolytic effects

In the present study, novel 2-cyclopropyl-3-ethynyl-4-(4-fluorophenyl) quinolines (4a-l) were recognized and evaluated as G-Protein Coupled Receptor (GPCR) ligands through molecular evaluations. Thrombin mediates adhesion of mast cell, a type of cell abundantly found in connective tissue and releasing histamine and other substances during inflammatory and allergic reactions, through phosphoinositol 3-kinase pathway. With this background, as preliminary, 4a-l are resolute to be potential leads, designated from their effective phosphoinositol 3-kinase (PI3-Kinase) inhibition potentials, best-docked scores, comparative ligand efficiency, and significant structural attributes evaluated by ab initio simulations. Since thrombin is one of the main reason for various cancer invasion in association with PI3Kinase, a thrombolytic potential of the compounds also analyzed. The experimental in vitro studies confirmed the significant enhancement as PI3Kinase inhibitors and appreciable enhancement in MTT assay of breast and skin cancer cell lines. Significantly, acetophenone substituent in the quinoline scaffold could be coherent to note the significant binding affinity to all the evaluated drug targets.

Self-organizing oligothiophene-nucleoside conjugates: Versatile synthesis via "Click"-chemistry

A versatile synthesis of novel oligothiophene-nucleoside conjugates based on Cu(l)-catalyzed alkyne-azide cycloaddition ("click-reaction") has been developed. Complementary thymidine- and adenosine-functionalized quaterthiophenes form recognition-driven superstructures via hydrogen bonding and other competing intermolecular forces. Self-aggregated fibers up to 30 μm in length were characterized with atomic force microscopy.

Application of FSO2N3 in preparation of diazo reagent

The invention discloses application of FSO2N3 in preparation of a diazo reagent. The application comprises the following step: in the presence of alkali, FSO2N3 and acetone dimethyl phosphate as shown in a formula 2 are subjected to a reaction as shown in the specification, and a Bestmann-Ohira and/or Seyferth-Gilbert reagent is obtained. According to the application, the Seyferth-Gilbert reagent and/or the Bestmann-Ohira reagent can be obtained at a high yield in half an hour, the two mixed reagents generated in the reaction do not need to be separated, and the one-pot method is directly applied to the synthesis of the terminal alkyne compound. And/or like.

Synthesis of the C1-C27 Fragment of Stambomycin D Validates Modular Polyketide Synthase-Based Stereochemical Assignments

The stambomycins are a family of bioactive macrolides isolated from Streptomyces ambofaciens. Aside from two stereocenters installed through cytochrome P450 oxidations, their stereochemistry has been predicted by sequence analysis of the polyketide synthase. We report a synthesis of the C1-C27 fragment of stambomycin D, the spectroscopic data of which correlates well with that of the natural product, further validating predictive sequence analysis as a powerful tool for stereochemical assignment of complex polyketide natural products.

Synthesis of chiral branched allylamines through dual photoredox/nickel catalysis

Allylamines are versatile building blocks in the synthesis of various naturally occurring products and pharmaceuticals. In contrast to terminal allylamines, the methods of synthesis of their branched congeners with internal, stereodefined double bonds are less explored. This work describes a new approach for the preparation of allylaminesviacross-coupling of alkyl bromides with simple 3-bromoallylamines by merging the photoredox approach and Ni catalysis. The reaction proceeds under mild conditions, under blue light irradiation, and in the presence of an organic dye, 4CzIPN, as a photocatalyst. The scope of suitable reaction partners is broad, including alkyl bromides bearing reactive functionalities (e.g., esters, nitriles, aldehydes, ketones, epoxides) andN-protected allylamines, as well asN-allylated secondary and tertiary amines and heterocycles. The employment of non-racemic starting materials allows for rapid and easy construction of complex multifunctional allylamine derivatives without the loss of enantiomeric purity.