224791-45-1

Basic information

• Product Name: Benzenamine, 2,2'-dithiobis[5-fluoro-
• Synonyms: 2-amino-4-fluorothiophenol disulfide;4,4'-difluoro-2,2'-diaminodiphenyl disulfide
• CAS NO: 224791-45-1
• Molecular Formula: C12H10F2N2S2
• Molecular Weight: 284.354
• Mol File: 224791-45-1.mol
• Article Data: 7

Chemical Properties

• Melting Point: 75-76 °C
• Boiling Point: 405.6±45.0 °C(Predicted)
• Density: 1.46±0.1 g/cm3(Predicted)
• CAS DataBase Reference: Benzenamine, 2,2'-dithiobis[5-fluoro-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzenamine, 2,2'-dithiobis[5-fluoro-(224791-45-1)
• EPA Substance Registry System: Benzenamine, 2,2'-dithiobis[5-fluoro-(224791-45-1)

Safety Data

• Hazardous Substances Data: 224791-45-1(Hazardous Substances Data)

Upstream product

• 458-05-9 1-(3-fluorophenyl)thiourea 
• 372-19-0 meta-fluoroaniline 
• 20358-07-0 2-amino-5-fluorobenzothiazole 

Downstream Products

• 872726-42-6 5-fluoro-2-(3-hydroxy-4-methoxyphenyl)-benzothiazole 
• 872726-44-8 NSC 721648 
• 872726-43-7 5-fluoro-2-(4-hydroxy-3-methoxyphenyl)-benzothiazole 
• 872726-34-6 5-fluoro-2-(4-methoxyphenyl)-1,3-benzothiazole 
• 872726-48-2 5-fluoro-2-(5-hydroxy-3,4-dimethoxyphenyl)benzothiazole 

Relevant articles and documents

Unexpected water addition to fluorinated 1,3λ4δ2,2,4-benzodithiadiazines with the formation of 2-amino-N-sulfinylbenzenesulfenamides

Fluoro-containing 1,3λ4δ2,2,4-benzodithiadiazines 2-4 unexpectedly add water to give previously unknown 2-amino-N-sulfinylbenzenesulfenamides 5-7 as the first derivatives of still undescribed 2-aminobenzenesulfenamide 10.

Synthesis and biological properties of benzothiazole, benzoxazole, and chromen-4-one analogues of the potent antitumor agent 2-(3,4-dimethoxyphenyl)-5- fluorobenzothiazole (PMX 610, NSC 721648)

New fluorinated 2-aryl-benzothiazoles, -benzoxazoles, and -chromen-4-ones have been synthesized and their activity against MCF-7 and MDA 468 breast cancer cell lines compared with the potent antitumor benzothiazole 5. Analogues such as 9a,b and 12a,d yielded submicromolar GI50 values in both cell lines; however, none of the new compounds approached 5 in terms of antitumor potency. For 5, binding to the aryl hydrocarbon receptor appeared to be necessary but not sufficient for growth inhibition.

Synthesis of carbon-11 labeled fluorinated 2-arylbenzothiazoles as novel potential PET cancer imaging agents

Fluorinated 2-arylbenzothiazoles are new potential antitumor drugs, which show potent and selective inhibitory activity against breast, lung, and colon cancer cell lines. Carbon-11 labeled fluorinated 2-arylbenzothiazoles may serve as novel probes for positron emission tomography (PET) to image tyrosine kinase in cancers. The preparation of 4-fluorinated 2-arylbenzothiazoles 4-fluoro-2-(3-benzloxy-4-methoxyphenyl)benzothiazole (6a) and 4-fluoro-2-(3,4-dimethoxyphenyl)benzothiazole (6b) was achieved by a modification of Jacobson thioanilide radical cyclization chemistry. Hydrogenolytic cleavage of the benzyl ether group of compound 6a using H2/Pd-C provided the precursor 4-fluoro-2-(3-hydroxy-4-methoxyphenyl)benzothiazole (7) for radiolabeling. Synthesis of radiolabeling precursors and the reference standards 5- and 6-fluorinated arylbenzothiazoles (11c-n) was achieved via the reaction of o-aminothiophenol disulfides with substituted benzaldehydes under reducing conditions. The target radiotracers carbon-11 labeled 4-, 5-, and 6-fluorinated arylbenzothiazoles (3-[11C]6b, 4-[11C]11c, 3-[11C]11c, 5-[11C]11f, 4-[11C]11f, 4-[11C]11i, 3-[11C]11i, 5-[11C]11l, and 4-[11C]11l) were prepared by O-[11C]methylation of the phenolic hydroxyl precursors (7, 11d, 11e, 11g, 11h, 11j, 11k, 11m, and 11n) with [11C]methyl triflate and isolated by solid-phase extraction (SPE) purification in 30-55% radiochemical yields.