Dimethyl [diazo(phenyl)methyl]phosphonate

Base Information

• Chemical Name: Dimethyl [diazo(phenyl)methyl]phosphonate
• CAS No.: 16965-72-3
• Molecular Formula: C9H11 N2 O3 P
• Molecular Weight: 226.172
• NSC Number: 287506
• DSSTox Substance ID: DTXSID80398619
• Nikkaji Number: J498.376I
• Mol file: 16965-72-3.mol

Synonyms:16965-72-3;DTXSID80398619;NSC287506;NSC-287506;Dimethyl [diazo(phenyl)methyl]phosphonate;alpha-Diazobenzylphosphonic acid dimethyl ester

Chemical Property of Dimethyl [diazo(phenyl)methyl]phosphonate

Chemical Property:

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Density: g/cm³
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 226.05072921
• Heavy Atom Count: 15
• Complexity: 299

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COP(=O)(C(=[N+]=[N-])C1=CC=CC=C1)OC
• General Description: [(Dimethoxyphosphoryl)(phenyl)methylidene]diazenium, also known as dimethyl phenyldiazomethylphosphonate or related names, is an α-diazo phosphonate compound that serves as a key intermediate in Rh(I)-catalyzed arylation reactions. It reacts with aryl boronic acids to form diarylmethylphosphonates through a proposed migratory insertion of rhodium carbene intermediates, enabling the synthesis of diverse phosphonate derivatives. [(dimethoxyphosphoryl)(phenyl)methylidene]diazenium is valuable in transition-metal-catalyzed transformations for constructing C–C bonds.

Technology Process of Dimethyl [diazo(phenyl)methyl]phosphonate

There total 8 articles about Dimethyl [diazo(phenyl)methyl]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: 88.0%

iodobenzene (591-50-4) + dimethyl 1-(1-diazo-2-oxopropyl)phosphonate (90965-06-3) → dimethyl α-diazobenzylphosphonate (16965-72-3)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate; In methanol; toluene; at 20 ℃; for 5h; Inert atmosphere;

DOI:10.1002/anie.201407653

Reference yield: 34.0%

→ dimethyl α-diazobenzylphosphonate (16965-72-3)

Guidance literature:

With 2-(3-(4-fluorophenoxy)-3-oxopropyl)benzenediazonium hexafluorophosphate (V); potassium carbonate; In tetrahydrofuran; at 0 - 20 ℃; for 0.25h;

Reference yield:

C16H19N2O5PS (28447-23-6) → dimethyl α-diazobenzylphosphonate (16965-72-3)

Guidance literature:

With sodium carbonate;

DOI:10.1021/jo00809a014

upstream raw materials:

dimethyl benzoylphosphonate

C₁₆H₁₉N₂O₅PS

anti-Benzoylphosphonsaeuredimethylester-p-tosylhydrazon

diazomethane

Downstream raw materials:

C₂₈H₃₀O₆P₂

[2-(Dimethoxy-phosphoryl)-2-phenyl-cyclopropyl]-phosphonic acid diethyl ester

[5,6-Dichloro-8-(dimethoxy-phosphoryl)-3,8-diphenyl-tricyclo[5.1.0.0^2,4]oct-5-en-3-yl]-phosphonic acid dimethyl ester

<7-Phenyl-norcaran-7-yl>-phosphonsaeure-dimethylester