12H-Benzo[b]phenothiazine

Base Information

• Chemical Name: 12H-Benzo[b]phenothiazine
• CAS No.: 258-08-2
• Molecular Formula: C16H11 N S
• Molecular Weight: 249.336
• NSC Number: 81120
• DSSTox Substance ID: DTXSID80948698
• Nikkaji Number: J39.640K
• Wikidata: Q82926520
• ChEMBL ID: CHEMBL1450360
• Mol file: 258-08-2.mol

Synonyms:12H-Benzo[b]phenothiazine;258-08-2;12H-Benzo(b)phenothiazine;Benzo[b]phenothiazine;MLS000737083;12H-5-THIA-12-AZATETRACENE;SR-01000780654;SR-01000780654-3;NSC81120;cid_255516;SCHEMBL8602753;CHEMBL1450360;BDBM65958;DTXSID80948698;IWKDFAWZFVGWAH-UHFFFAOYSA-N;HMS2806C19;NSC-81120;SMR000444068

Chemical Property of 12H-Benzo[b]phenothiazine

Chemical Property:

• Vapor Pressure: 6.36E-09mmHg at 25°C
• Boiling Point: 467.7°Cat760mmHg
• Flash Point: 236.7°C
• Density: 1.274g/cm³
• XLogP3: 5.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 249.06122053
• Heavy Atom Count: 18
• Complexity: 306

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C=C3C(=CC2=C1)NC4=CC=CC=C4S3

Technology Process of 12H-Benzo[b]phenothiazine

There total 9 articles about 12H-Benzo[b]phenothiazine 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: 40.0%

2-amino-benzenethiol (137-07-5) + 2,3-naphthalenediol (92-44-4) → benzophenothiazine (258-08-2)

Guidance literature:

at 200 ℃;

DOI:10.1055/a-1304-4575

Reference yield:

2-amino-3-(2-bromophenylthio)naphthalene → benzophenothiazine (258-08-2)

Guidance literature:

With chloro-(2-dicyclohexylphosphino-2’,6’-diisopropoxy-1,1‘-biphenyl)[2-(2-aminoethyl)phenyl] palladium(ll) methyl-tert-butyl ether adduct; sodium t-butanolate; ruphos; In toluene; at 110 ℃; Inert atmosphere;

DOI:10.1246/cl.180304

Reference yield:

S-(2-bromophenyl)-S-methylsulfilimine → benzophenothiazine (258-08-2)

Guidance literature:

Multi-step reaction with 2 steps

1: cesium fluoride / acetonitrile / 24 h / 20 °C / Inert atmosphere

2: chloro-(2-dicyclohexylphosphino-2’,6’-diisopropoxy-1,1‘-biphenyl)[2-(2-aminoethyl)phenyl] palladium(ll) methyl-tert-butyl ether adduct; ruphos; sodium t-butanolate / toluene / 110 °C / Inert atmosphere

With chloro-(2-dicyclohexylphosphino-2’,6’-diisopropoxy-1,1‘-biphenyl)[2-(2-aminoethyl)phenyl] palladium(ll) methyl-tert-butyl ether adduct; cesium fluoride; sodium t-butanolate; ruphos; In toluene; acetonitrile; 2: |Buchwald-Hartwig Coupling;

DOI:10.1246/cl.180304

upstream raw materials:

2-amino-benzenethiol

2,3-naphthalenediol

12H-Benzophenothiazine-6,11-dione

acetic acid

Refernces

• 1、 Dadashi-Silab, Sajjad,Pan, Xiangcheng,Matyjaszewski, Krzysztof. "Phenyl Benzo[b]phenothiazine as a Visible Light Photoredox Catalyst for Metal-Free Atom Transfer Radical Polymerization". . p. 5972 - 5977. Retrieved 2017.
• 2、 Matsuzawa, Tsubasa,Uchida, Keisuke,Yoshida, Suguru,Hosoya, Takamitsu. "Synthesis of diverse phenothiazines by direct thioamination of arynes with S-(o-bromoaryl)-S-methylsulfilimines and subsequent intramolecular BuchwaldHartwig amination". . p. 825 - 828. Retrieved 2018/07/05.