4-Nitrophenyl diphenylphosphinate

Base Information

• Chemical Name: 4-Nitrophenyl diphenylphosphinate
• CAS No.: 10259-20-8
• Molecular Formula: C18H14 N O4 P
• Molecular Weight: 339.287
• Hs Code.: 2931900090
• UNII: TBU9ZZ2FN9
• Nikkaji Number: J496.757G
• Mol file: 10259-20-8.mol

Synonyms:4-nitrophenyl-DPP;O-4-(nitrophenyl)diphenyl phosphinate

Chemical Property of 4-Nitrophenyl diphenylphosphinate

Chemical Property:

• Vapor Pressure: 1.76E-09mmHg at 25°C
• Boiling Point: 495.7°Cat760mmHg
• Flash Point: 253.6°C
• PSA: 91.70000
• Density: 1.33g/cm³
• LogP: 4.42590
• XLogP3: 4.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 339.06604493
• Heavy Atom Count: 24
• Complexity: 436

Purity/Quality:

98%,99%, ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)P(=O)(C2=CC=CC=C2)OC3=CC=C(C=C3)[N+](=O)[O-]
• General Description: 1-Diphenylphosphoryloxy-4-nitro-benzene (or p-nitrophenyl diphenylphosphinate) is a compound involved in nucleophilic substitution reactions, particularly with hydroxide (OH^-) and hydroperoxide (HOO^-) ions. Kinetic studies reveal that its alkaline hydrolysis proceeds via a concerted mechanism, as evidenced by linear Yukawa-Tsuno plots (ρ = 0.95, r = 0.55), indicating partial negative charge development on the leaving group oxygen. The reactivity of OH^- surpasses that of ethoxide (EtO^-) despite the latter's higher basicity, suggesting that nucleophilicity is not solely dictated by basicity. Additionally, the α-effect is observed in reactions with HOO^-, further highlighting its role in nucleophilic processes.

Technology Process of 4-Nitrophenyl diphenylphosphinate

There total 6 articles about 4-Nitrophenyl diphenylphosphinate 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: 93.0%

4-nitro-phenol (100-02-7,78813-13-5,89830-32-0) + Diphenylphosphine oxide (4559-70-0) → 4-nitrophenyl diphenylphosphinate (10259-20-8)

Guidance literature:

With methyl-triphenylphosphonium iodide; caesium carbonate; In chloroform; at 20 ℃; for 1h;

DOI:10.1002/ejoc.202000385

Reference yield: 89.0%

4-nitro-phenol (100-02-7,78813-13-5,89830-32-0) + Diphenylphosphinic chloride (1499-21-4) → 4-nitrophenyl diphenylphosphinate (10259-20-8)

Guidance literature:

With triethylamine; In benzene; for 0.5h; Heating;

DOI:10.1023/A:1010471710580

Reference yield: 69.0%

(4-nitrophenyl) N-(4-nitrophenoxycarbonyl)trichloroimidate + Ethyl diphenylphosphinite (719-80-2) → α-(4-nitrophenoxy)-β,β-dichlorovinyl isocyanate + 4-nitrophenyl diphenylphosphinate (10259-20-8)

Guidance literature:

In benzene; at 5 ℃; for 24h;

DOI:10.1007/s11176-005-0082-8

upstream raw materials:

4-nitro-phenol

Diphenylphosphinic chloride

Ethyl diphenylphosphinite

diphenyl-phosphinic acid

Downstream raw materials:

4-nitro-phenol

diphenyl(piperidin-1-yl)phosphine oxide

2,4,6-tris(4-methoxyphenyl)-2,4,6-trisulfanylene-1,3,5,2,4,6-trioxatriphosphinane

p-nitrophenyl diphenylphosphinothionate

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