(1-DIAZO-2-OXO-PROPYL)-PHOSPHONIC ACID DIMETHYL ESTER

Base Information

• Chemical Name: (1-DIAZO-2-OXO-PROPYL)-PHOSPHONIC ACID DIMETHYL ESTER
• CAS No.: 90965-06-3
• Molecular Formula: C5H9 N2 O4 P
• Molecular Weight: 192.111
• Hs Code.: 29319090
• European Community (EC) Number: 692-521-0
• UNII: 96G79J0LR6
• DSSTox Substance ID: DTXSID70455381
• Nikkaji Number: J1.192.388G
• Mol file: 90965-06-3.mol

Synonyms:Phosphonicacid, (1-diazo-2-oxopropyl)-, dimethyl ester (9CI); 1-Diazo-1-(dimethylphosphono)acetone; Bestmann-Ohira reagent; Dimethyl(1-azo-2-oxopropyl)phosphonate; Dimethyl (1-azoacetonyl)phosphonate; Dimethyl(1-diazo-2-oxopropyl)phosphonate; Dimethyl (acetyldiazomethyl)phosphonate;Ohira-Bestmann phosphonate; Ohira-Bestmann reagent; Ohira's reagent; a-Azido-a-(dimethyl phosphono)acetone

Chemical Property of (1-DIAZO-2-OXO-PROPYL)-PHOSPHONIC ACID DIMETHYL ESTER

Chemical Property:

• Refractive Index: n20/D1.352-1.354
• Flash Point: 2℃
• PSA: 99.80000
• Density: 1.28
• LogP: 0.77066
• Storage Temp.: 2-8°C
• Solubility.: Chloroform, Methanol (Slightly)
• XLogP3: -0.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 192.02999377
• Heavy Atom Count: 12
• Complexity: 273

Purity/Quality:

98% ^*data from raw suppliers

Dimethyl (1-Diazo-2-oxopropyl)phosphonate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F,Xn
• Hazard Codes: F,Xn
• Statements: 11-20/21/22-36
• Safety Statements: 16-26-36/37

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)C(=[N+]=[N-])P(=O)(OC)OC
• Uses: Reagent for transformation of aldehydes to terminal alkynes and ketones to methyl enol ethers. 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.

Technology Process of (1-DIAZO-2-OXO-PROPYL)-PHOSPHONIC ACID DIMETHYL ESTER

There total 5 articles about (1-DIAZO-2-OXO-PROPYL)-PHOSPHONIC ACID DIMETHYL ESTER which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

dimethyl (2-oxopropyl)phosphonate (4202-14-6) → dimethyl 1-(1-diazo-2-oxopropyl)phosphonate (90965-06-3)

Guidance literature:

dimethyl (2-oxopropyl)phosphonate; With sodium hydride; In tetrahydrofuran; mineral oil; benzene; at 20 ℃; for 1h; Inert atmosphere; Cooling with ice;

With 4-toluenesulfonyl azide; In tetrahydrofuran; mineral oil; benzene; at 20 ℃; Inert atmosphere;

DOI:10.1016/j.ejmech.2016.06.057

Reference yield: 88.35%

4-toluenesulfonyl azide (941-55-9) + dimethyl (2-oxopropyl)phosphonate (4202-14-6) → dimethyl 1-(1-diazo-2-oxopropyl)phosphonate (90965-06-3)

Guidance literature:

dimethyl (2-oxopropyl)phosphonate; With sodium hydride; In tetrahydrofuran; at 0 ℃; for 1h;

4-toluenesulfonyl azide; at 0 ℃; for 0.5h;

Reference yield:

dimethyl (2-oxopropyl)phosphonate (4202-14-6) + 4-acetamidobenzenesulfonyl azide (2158-14-7) → dimethyl 1-(1-diazo-2-oxopropyl)phosphonate (90965-06-3)

Guidance literature:

With potassium carbonate; In tetrahydrofuran; at 0 ℃; for 48h;

DOI:10.1002/hlca.200590235

upstream raw materials:

dimethyl (2-oxopropyl)phosphonate

4-acetamidobenzenesulfonyl azide

4-toluenesulfonyl azide

Downstream raw materials:

tert-butyl (R)-4-ethynyl-2,2-dimethyloxazolidine-3-carboxylate

(2R,3S)-1-O-tritylhex-5-yne-1,2,3-triol

O-tert-butyl N-(S)-(5-methylhex-1-yn-3-yl)carbamate

1-undecyne

Refernces

• 1、 Chuh, Kelly N.,Batt, Anna R.,Zaro, Balyn W.,Darabedian, Narek,Marotta, Nicholas P.,Brennan, Caroline K.,Amirhekmat, Arya,Pratt, Matthew R.. "The New Chemical Reporter 6-Alkynyl-6-deoxy-GlcNAc Reveals O-GlcNAc Modification of the Apoptotic Caspases That Can Block the Cleavage/Activation of Caspase-8". . p. 7872 - 7885. Retrieved 2017.
• 2、 Schillinger, Eva-Kathrin,Kuemin, Michael,Digennaro, Angela,Mena-Osteritz, Elena,Schmid, Sylvia,Wennemers, Helma,Baeuerle, Peter. "Guiding suprastructure chirality of an oligothiophene by a single amino Acid". . p. 4511 - 4521. Retrieved 2013.
• 3、 -. "Application of FSO2N3 in preparation of diazo reagent". Paragraph 0103-0106. . Retrieved 2021/06/06.
• 4、 Bowen, James I.,Crump, Matthew P.,Wang, Luoyi,Willis, Christine L.. "Ambruticins: tetrahydropyran ring formation and total synthesis". supporting information. p. 6210 - 6215. Retrieved 2021/07/28.