4-(5-Fluoro-1,3-benzothiazol-2-yl)-2-methylaniline

Base Information

• Chemical Name: 4-(5-Fluoro-1,3-benzothiazol-2-yl)-2-methylaniline
• CAS No.: 260443-89-8
• Molecular Formula: C14H11FN2S
• Molecular Weight: 258.319
• European Community (EC) Number: 809-097-1
• NSC Number: 703786
• UNII: 3J3GHW53E4
• DSSTox Substance ID: DTXSID80327929
• Nikkaji Number: J1.233.528H
• Wikidata: Q82090074
• ChEMBL ID: CHEMBL286593
• Mol file: 260443-89-8.mol

Synonyms:2-(4-amino-3-methylphenyl)-5-fluorobenzothiazole;2-NMPh-FBzT;5F-203

Chemical Property of 4-(5-Fluoro-1,3-benzothiazol-2-yl)-2-methylaniline

Chemical Property:

• PSA: 67.15000
• LogP: 4.57420
• Storage Temp.: 2-8°C
• Solubility.: DMSO: soluble20mg/mL, clear
• XLogP3: 3.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 258.06269769
• Heavy Atom Count: 18
• Complexity: 302

Purity/Quality:

99%+, ^*data from raw suppliers

5-Fluoro203 ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xn
• Statements: 22

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(C=CC(=C1)C2=NC3=C(S2)C=CC(=C3)F)N
• Uses: 5-Fluoro 203 is a cytotoxic agent which actiates AhR signaling, inducing transcription of CYP1A1 which leads to the formation of DNA adducts and cell cycle arrest.

Technology Process of 4-(5-Fluoro-1,3-benzothiazol-2-yl)-2-methylaniline

There total 10 articles about 4-(5-Fluoro-1,3-benzothiazol-2-yl)-2-methylaniline 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: 71.0%

4-amino-N-(5-fluoro-2-iodophenyl)-3-methylbenzamide → 4-(5-fluorobenzothiazol-2-yl)-2-methylphenylamine (260443-89-8)

Guidance literature:

4-amino-N-(5-fluoro-2-iodophenyl)-3-methylbenzamide; With sodiumsulfide nonahydrate; In N,N-dimethyl-formamide; at 80 ℃; for 12h; Schlenk technique; Sealed tube;

With hydrogenchloride; In N,N-dimethyl-formamide; at 20 ℃; for 10h;

DOI:10.1016/j.mcat.2022.112115

Reference yield: 71.0%

bis[4-fluoro-2-(3-methyl-4-nitrobenzoyl)aminophenyl] disulfide → 4-(5-fluorobenzothiazol-2-yl)-2-methylphenylamine (260443-89-8)

Guidance literature:

With hydrogenchloride; tin(ll) chloride; In ethanol; for 15h; Heating;

DOI:10.1021/jm001104n

Reference yield: 48.0%

5-fluoro-2-(3-methyl-4-nitrophenyl)benzothiazole (260443-96-7) → 4-(5-fluorobenzothiazol-2-yl)-2-methylphenylamine (260443-89-8)

Guidance literature:

With tin(II) chloride hydrate; In ethanol; for 3h; Reflux;

DOI:10.1016/j.bmc.2015.09.052

upstream raw materials:

5-fluoro-2-(3-methyl-4-nitrophenyl)benzothiazole

2-bromo-5-fluoroaniline

3-methyl-4-nitro-benzoyl chloride

N-(2-bromo-5-fluorophenyl)-3-methyl-4-nitrobenzothioamide

Refernces

• 1、 Stone, Erica L.,Citossi, Francesca,Singh, Rajinder,Kaur, Balvinder,Gaskell, Margaret,Farmer, Peter B.,Monks, Anne,Hose, Curtis,Stevens, Malcolm F.G.,Leong, Chee-Onn,Stocks, Michael,Kellam, Barrie,Marlow, Maria,Bradshaw, Tracey D.. "Antitumour benzothiazoles. Part 32: DNA adducts and double strand breaks correlate with activity; Synthesis of 5F203 hydrogels for local delivery". supporting information. p. 6891 - 6899. Retrieved 2015/11/11.
• 2、 Ma, Dawei,Xue, Peng,Jiang, Yongwen,Xie, Siwei,Zhang, Xiaojing,Dong, Jinhua. "Efficient and economical access to substituted benzothiazoles: Copper-catalyzed coupling of 2-haloanilides with metal sulfides and subsequent condensation". supporting information; experimental part. p. 4222 - 4225. Retrieved 2009/11/30.