Phenylethynylphosphonic acid

Base Information

• Chemical Name: Phenylethynylphosphonic acid
• CAS No.: 4672-31-5
• Molecular Formula: C8H7 O3 P
• Molecular Weight: 182.116
• DSSTox Substance ID: DTXSID301297285
• ChEMBL ID: CHEMBL1482747
• Mol file: 4672-31-5.mol

Synonyms:phenylethynylphosphonic acid;MLS000105116;Oprea1_075013;4672-31-5;1-Phosphono-2-phenylacetylene;SCHEMBL4796203;CHEMBL1482747;(2-phenylethynyl)phosphonic acid;NBUGGOCWWMRVRX-UHFFFAOYSA-N;DTXSID301297285;P-(2-Phenylethynyl)phosphonic acid;AKOS006275756;SMR000055045

Chemical Property of Phenylethynylphosphonic acid

Chemical Property:

• PSA: 67.34000
• LogP: 1.17330
• XLogP3: 0.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 182.01328108
• Heavy Atom Count: 12
• Complexity: 248

Purity/Quality:

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)C#CP(=O)(O)O

Technology Process of Phenylethynylphosphonic acid

There total 8 articles about Phenylethynylphosphonic acid 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:

phenylethynyl-phosphonic acid dimethyl ester (33802-53-8) → phenylethynylphosphonic acid (4672-31-5)

Guidance literature:

With trimethylsilyl bromide; In dichloromethane; at 20 ℃; for 16h;

DOI:10.1021/ja510477q

Reference yield:

phenylacetylene (536-74-3) → phenylethynylphosphonic acid (4672-31-5)

Guidance literature:

Multi-step reaction with 2 steps

1: benzene; phosphorus (V)-chloride / und Behandeln des Reaktionsprodukts mit Wasser worden

2: ethanolic KOH-solution

With potassium hydroxide; phosphorus pentachloride; benzene;

Reference yield:

-(1-iodo-2-(phenylsulfonyl)vinyl)benzene → phenylethynylphosphonic acid (4672-31-5)

Guidance literature:

Multi-step reaction with 3 steps

1: potassium carbonate / acetone / 5 h / Reflux

2: tetrahydrofuran / 60 °C

3: trimethylsilyl bromide / dichloromethane / 16 h / 20 °C

With trimethylsilyl bromide; potassium carbonate; In tetrahydrofuran; dichloromethane; acetone;

DOI:10.1021/ja510477q

upstream raw materials:

(β-chlorostyryl)phosphonic acid

diethyl phenylethynylphosphonate

1-chlorostyrene

phenylacetylene

Downstream raw materials:

(2-phenylethyl)phosphonic acid

Refernces

• 1、 Kluczyk,Szefczyk,Amrhein,Zon. "(E)-cinnamic acid analogues as inhibitors of phenylalanine ammonia-lyase and of anthocyanin biosynthesis". . p. 583 - 592. Retrieved 2007/10/03.