2-(Trifluoromethyl)phenothiazine

Base Information

• Chemical Name: 2-(Trifluoromethyl)phenothiazine
• CAS No.: 92-30-8
• Molecular Formula: C13H8F3NS
• Molecular Weight: 267.274
• Hs Code.: 29349990
• European Community (EC) Number: 202-145-7
• NSC Number: 50438
• UNII: 877S053KX3
• DSSTox Substance ID: DTXSID3059050
• Nikkaji Number: J4.352D
• Wikidata: Q27164667
• Pharos Ligand ID: YQQ9DM716Z4Q
• ChEMBL ID: CHEMBL541018
• Mol file: 92-30-8.mol

Synonyms:trifluoromethylphenothiazine

Chemical Property of 2-(Trifluoromethyl)phenothiazine

Chemical Property:

• Appearance/Colour: yellow to green powder
• Vapor Pressure: 1.49E-10mmHg at 25°C
• Melting Point: 188-190 °C(lit.)
• Refractive Index: 1.531
• Boiling Point: 361.1 °C at 760 mmHg
• PKA: -2.60±0.20(Predicted)
• Flash Point: 172.2 °C
• PSA: 37.33000
• Density: 1.369 g/cm³
• LogP: 5.05160
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 0
• Exact Mass: 267.03295492
• Heavy Atom Count: 18
• Complexity: 307

Purity/Quality:

99.9% ^*data from raw suppliers

2-(Trifluoromethyl)phenothiazine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,Xi
• Hazard Codes: Xn,Xi
• Statements: 20/21/22-22
• Safety Statements: 36-37/39-26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)NC3=C(S2)C=CC(=C3)C(F)(F)F
• Uses: 2-(Trifluoromethyl)phenothiazine is used in the synthesis of antitubercolosis pharmaceuticals as well as antiproliferatives.

Technology Process of 2-(Trifluoromethyl)phenothiazine

There total 24 articles about 2-(Trifluoromethyl)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: 95.0%

10-<3-(4-methoxyethoxymethoxyethyl-1-piperazinyl)-3-oxopropyl>-2-trifluoromethyl-10H-phenothiazine (89507-40-4) → 2-(trifluoromethyl)-10H-phenothiazine (92-30-8) + 10-(3-hydroxy<3,3-2H2>propyl)-2-trifluoromethyl-10H-phenothiazine (89507-41-5)

Guidance literature:

With lithium aluminium deuteride; In diethyl ether; RT, 1 h, reflux, 30 min;

DOI:10.1002/jps.2600730123

Reference yield: 90.0%

1-Bromo-2-iodobenzene (583-55-1) + 2-amino-4-trifluoromethylthiophenol (19406-49-6) → 2-(trifluoromethyl)-10H-phenothiazine (92-30-8)

Guidance literature:

With copper(l) iodide; potassium carbonate; In dimethyl sulfoxide; at 120 ℃; for 48h; regioselective reaction; Inert atmosphere;

DOI:10.1039/c2cc30814b

Reference yield: 89.0%

o-bromothiophenol (6320-02-1) + 2-iodo-4-(trifluoromethyl)benzenamine (105202-02-6) → 2-(trifluoromethyl)-10H-phenothiazine (92-30-8)

Guidance literature:

o-bromothiophenol; 2-iodo-4-(trifluoromethyl)benzenamine; With ferric citrate; In N,N-dimethyl-formamide; at 110 ℃; Green chemistry;

With potassium carbonate; In N,N-dimethyl-formamide; at 110 ℃; regioselective reaction; Green chemistry;

DOI:10.2174/1570178615666180806114523

upstream raw materials:

N-(3-trifluoromethylphenyl)aniline

formic acid-[2-(2-nitro-5-trifluoromethyl-phenylsulfanyl)-anilide]

flufenamic acid

(2-nitro-4-(trifluoromethyl)phenyl)phenylthioether

Downstream raw materials:

2-chloro-1-(2-(trifluoromethyl)-10H-phenothiazin-10-yl)ethanone

10-[3-(4-Methoxy-phenyl)-propyl]-2-trifluoromethyl-10H-phenothiazine

10-[3-(3,4-Dimethoxy-phenyl)-propyl]-2-trifluoromethyl-10H-phenothiazine

3-(2-trifluoromethyl-phenothiazin-10-yl)propionitrile

Refernces

• 1、 Yao, Wubing,Li, Rongrong,Yang, Jianguo,Hao, Feiyue. "Hydride-catalyzed selectively reductive cleavage of unactivated tertiary amides using hydrosilane". . p. 3874 - 3878. Retrieved 2019/08/07.
• 2、 Zhou, Yue,Zeng, Qingle,Zhang, Li. "Transition-metal-free synthesis of phenothiazines from S-2-acetamidophenyl ethanethioate and ortho-dihaloarenes". supporting information. p. 710 - 715. Retrieved 2017/03/27.