3H-1,3-benzazaphosphole

Base Information

• Chemical Name: 3H-1,3-benzazaphosphole
• CAS No.: 32881-50-8
• Molecular Formula: C₇H₆NP
• Molecular Weight: 135.105
• DSSTox Substance ID: DTXSID30580486
• Nikkaji Number: J3.305.076C
• Wikidata: Q82471328
• Mol file: 32881-50-8.mol

Synonyms:3H-1,3-benzazaphosphole;1H-1,3-Benzazaphosphole;32881-50-8;SCHEMBL3076418;SCHEMBL3076422;DTXSID30580486;AKOS006352533

Chemical Property of 3H-1,3-benzazaphosphole

Chemical Property:

• PSA: 12.89000
• LogP: 2.26610
• XLogP3: 1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 135.023786193
• Heavy Atom Count: 9
• Complexity: 105

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)N=CP2

Technology Process of 3H-1,3-benzazaphosphole

There total 5 articles about 3H-1,3-benzazaphosphole 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:

(2-formylamido)benzenephosphonic acid diethyl ester → o-Phospholino-N-methylanilin (84759-23-9) + 1H-1,3-benzazaphosphole (32881-50-8)

Guidance literature:

(2-formylamido)benzenephosphonic acid diethyl ester; With lithium aluminium tetrahydride; In diethyl ether; at -10 - 20 ℃; for 72h; Inert atmosphere;

With water; In diethyl ether;

DOI:10.1002/hc.21111

Reference yield:

2-bromo-N-(tert-butoxycarbonyl)aniline (78839-75-5) → 1-Boc-2-phosphinoaniline + 1H-1,3-benzazaphosphole (32881-50-8)

Guidance literature:

Multi-step reaction with 2 steps

1: palladium diacetate / 0.5 h / 175 °C / Inert atmosphere

2: lithium aluminium tetrahydride / diethyl ether / Inert atmosphere

With lithium aluminium tetrahydride; palladium diacetate; In diethyl ether;

DOI:10.1039/c0dt00881h

Reference yield:

2-bromoaniline (615-36-1) → o-Phospholino-N-methylanilin (84759-23-9) + 1H-1,3-benzazaphosphole (32881-50-8)

Guidance literature:

Multi-step reaction with 3 steps

1.1: copper(II) oxide / Heating

2.1: palladium dichloride / 0.17 h / 180 °C / Inert atmosphere

2.2: 180 - 185 °C / Inert atmosphere

3.1: lithium aluminium tetrahydride / diethyl ether / 72 h / -10 - 20 °C / Inert atmosphere

With lithium aluminium tetrahydride; copper(II) oxide; palladium dichloride; In diethyl ether;

DOI:10.1002/hc.21111

upstream raw materials:

N-(tert-butoxycarbonyl)-2-aminophenylphosphonic acid diethyl ester

2-bromo-N-(tert-butoxycarbonyl)aniline

2-bromoaniline

N-(2-bromophenyl)formamide

Refernces

Cyclization of C-phosphorylated (P^III) arylformamidines to 3H-1,3-benzazaphospholes

10.1016/j.tet.2011.08.007

The study focuses on the synthesis of 3H-1,3-benzazaphospholes, a class of potential organophosphorus ligands, from C-phosphorylated P(III) arylformamidines. The researchers investigated the influence of various electron-donating and electron-withdrawing substituents on the cyclization reaction rate, as well as the impact of steric effects at the phosphorus atom. They proposed a plausible mechanism for the cyclization based on DFT calculations and experimental evidence. The study utilized a range of arylformamidines with different substituents, such as dimethylamino, methoxy, and trifluoromethyl groups, to explore their effects on the cyclization process. The purpose of these chemicals was to modify the reactivity and stability of the intermediates and products in the synthesis of benzazaphospholes, providing insights into the structure-activity relationships in these reactions. The study also explored the impact of adding ammonium salts on the cyclization rate, suggesting different catalytic effects for various anions.