Dimethyl (diazomethyl)phosphonate

Base Information

• Chemical Name: Dimethyl (diazomethyl)phosphonate
• CAS No.: 27491-70-9
• Molecular Formula: C₃H₇N₂O₃P
• Molecular Weight: 150.074
• UNII: WK47F6C50T
• DSSTox Substance ID: DTXSID60408487
• Nikkaji Number: J730.814K
• NSC Number: 294729
• Wikidata: Q27292692
• Mol file: 27491-70-9.mol

Synonyms:dimethyl diazomethylphosphonate;27491-70-9;Dimethyl (diazomethyl)phosphonate;diazo(dimethoxyphosphoryl)methane;Dimethylphosphonodiazomethane;Seyferth-gilbert reagent;Phosphonic acid, P-(diazomethyl)-, dimethyl ester;NSC-294729;Seyferth-gilbert reagent [MI];(Dimethoxyphosphoryl)diazomethane;WK47F6C50T;NSC294729;UNII-WK47F6C50T;SCHEMBL669123;DTXSID60408487;QUZMIAJIRIZFQN-UHFFFAOYSA-N;MFCD16876592;AKOS025402656;(diazomethyl) phosphonic acid dimethyl ester;CS-0197547;FT-0667394;P-(Diazomethyl)phosphonic Acid Dimethyl Ester;A903743;J-016788;Q27292692

Chemical Property of Dimethyl (diazomethyl)phosphonate

Chemical Property:

• Refractive Index: nD25 1.4585
• Boiling Point: bp0.42 59°
• PSA: 82.73000
• LogP: 0.81146
• Storage Temp.: -20°C Freezer, Under Inert Atmosphere
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: -0.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 150.01942909
• Heavy Atom Count: 9
• Complexity: 166

Purity/Quality:

98% ^*data from raw suppliers

DimethylDiazomethylphosphonate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COP(=O)(C=[N+]=[N-])OC
• Uses: Reagent for one-carbon homologation of aldehydes and ketones to alkynes. Seyferth-Gilbert Reagent

Technology Process of Dimethyl (diazomethyl)phosphonate

There total 3 articles about Dimethyl (diazomethyl)phosphonate 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:

dimethyl (2-oxopropyl)phosphonate (4202-14-6) → dimethyl 1-(1-diazo-2-oxopropyl)phosphonate (90965-06-3) + dimethyl diazomethylphosphonate (27491-70-9,28447-24-7,25411-73-8)

Guidance literature:

With fluorosulfonyl azide; potassium carbonate; In tetrahydrofuran; tert-butyl methyl ether; at 20 ℃; for 0.5h; Reagent/catalyst;

Reference yield:

4-acetamidobenzenesulfonyl azide (2158-14-7) → p-acetylaminobenzenesulfonamide (121-61-9) + dimethyl diazomethylphosphonate (27491-70-9,28447-24-7,25411-73-8)

Guidance literature:

With triethylamine; dimethyl (3,3,3-trifluoro-2,2-dihydroxypropyl)phosphonate; In acetonitrile; at 0 - 20 ℃;

DOI:10.1021/jo951944n

Reference yield:

dimethyl (3,3,3-trifluoro-2,2-dihydroxypropyl)phosphonate (153650-87-4) → p-acetylaminobenzenesulfonamide (121-61-9) + dimethyl diazomethylphosphonate (27491-70-9,28447-24-7,25411-73-8)

Guidance literature:

With 4-acetamidobenzenesulfonyl azide; triethylamine; In acetonitrile; at 0 - 20 ℃;

DOI:10.1021/jo951944n

upstream raw materials:

4-acetamidobenzenesulfonyl azide

dimethyl (3,3,3-trifluoro-2,2-dihydroxypropyl)phosphonate

dimethyl (2-oxopropyl)phosphonate

Downstream raw materials:

diphenyl acetylene

propargyl benzene

dimethyl <<(p-tolylsulfonyl)oxy>methyl>phosphonate

1-[1-[((E)-But-2-enyl)oxy]-meth-(Z)-ylidene]-2-methyl-cyclohexane

Refernces

• 1、 Brown, Dean G.,Velthuisen, Emil J.,Commerford, Jessica R.,Brisbois, Ronald G.,Hoye, Thomas R.. "A convenient synthesis of dimethyl (diazomethyl)phosphonate (Seyferth/Gilbert reagent)". . p. 2540 - 2541. Retrieved 2007/10/03.