1219501-75-3

Basic information

• Product Name: 1-BROMO-3,5-DIMERCAPTOBENZENE
• Synonyms: 5-BROMO-1,3-BENZENEDITHIOL;1-BROMO-3,5-DIMERCAPTOBENZENE
• CAS NO: 1219501-75-3
• Molecular Formula: C₆H₅BrS₂
• Molecular Weight: 221.14
• EINECS: 691-460-7
• Product Categories: Sulfur Compounds (for Synthesis);Synthetic Organic Chemistry
• Mol File: 1219501-75-3.mol
• Article Data: 1

Chemical Properties

• Melting Point: 76.0 to 80.0 °C
• Appearance: /
• Storage Temp.: Refrigerator
• Solubility: soluble in Methanol
• CAS DataBase Reference: 1-BROMO-3,5-DIMERCAPTOBENZENE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-BROMO-3,5-DIMERCAPTOBENZENE(1219501-75-3)
• EPA Substance Registry System: 1-BROMO-3,5-DIMERCAPTOBENZENE(1219501-75-3)

Safety Data

• Hazardous Substances Data: 1219501-75-3(Hazardous Substances Data)

Usage

Uses

5-BROMO-1,3-BENZENEDITHIOL is a useful research chemical.

Synthetic route

1,3-di(tert-butylsulfanyl)-5-bromobenzene → 5-bromobenzene-1,3-dithiol (1219501-75-3)

Conditions	Yield
Stage #1: 1,3-di(tert-butylsulfanyl)-5-bromobenzene With aluminum (III) chloride In toluene at 20℃; for 65h; Inert atmosphere; Stage #2: With hydrogenchloride; water; sodium chloride In toluene; pentane	88%

3,5-difluorobromobenzene (461-96-1) → 5-bromobenzene-1,3-dithiol (1219501-75-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: 1-methyl-pyrrolidin-2-one / 20 °C / Cooling with ice 2: aluminum (III) chloride / toluene / 65 h / 20 °C / Inert atmosphere View Scheme

5-bromobenzene-1,3-dithiol (1219501-75-3) → 5-bromobenzene-1,3-bis(sulfur chlorotetrafluoride)

Conditions	Yield
Stage #1: 5-bromobenzene-1,3-dithiol With potassium fluoride In acetonitrile at 20℃; for 2h; Inert atmosphere; Cooling with ice; Stage #2: With chlorine In acetonitrile at 20℃; Inert atmosphere; Cooling with ice;	65%
With potassium fluoride; chlorine In acetonitrile at 20℃; Cooling with ice;

5-bromobenzene-1,3-dithiol (1219501-75-3) → 1,3-bis(pentafluorosulfanyl)-5-bromobenzene (432028-10-9)

Conditions	Yield
With fluorine In acetonitrile at -5℃; for 0.666667h; Inert atmosphere;	25%
Multi-step reaction with 2 steps 1: potassium fluoride; chlorine / acetonitrile / 20 °C / Cooling with ice 2: antimony pentafluoride / dichloromethane / 5 h / -85 - -15 °C View Scheme

Upstream product

• 795274-44-1 1,3-di(tert-butylsulfanyl)-5-bromobenzene 
• 461-96-1 3,5-difluorobromobenzene 

Downstream Products

• 432028-10-9 1,3-bis(pentafluorosulfanyl)-5-bromobenzene 

Relevant articles and documents

Discovery of practical production processes for arylsulfur pentafluorides and their higher homologues, bis- and tris(sulfur pentafluorides): Beginning of a new era of "super-trifluoromethyl" arene chemistry and its industry

Various arylsulfur pentafluorides, ArSF5, have long been desired in both academic and industrial areas, and ArSF5 compounds have attracted considerable interest in many areas such as medicines, agrochemicals, and other new materials, since the highly stable SF5 group is considered a "super-trifluoromethyl group" due to its significantly higher electronegativity and lipophilicity. This article describes the first practical method for the production of various arylsulfur pentafluorides and their higher homologues, bis- and tris(sulfur pentafluorides), from the corresponding diaryl disulfides or aryl thiols. The method consists of two steps: (Step 1) treatment of a diaryl disulfide or an aryl thiol with chlorine in the presence of an alkali metal fluoride, and (step 2) treatment of the resulting arylsulfur chlorotetrafluoride with a fluoride source, such as ZnF2, HF, and Sb(III/V) fluorides. The intermediate arylsulfur chlorotetrafluorides were isolated by distillation or recrystallization and characterized. The aspects of these new reactions are revealed and reaction mechanisms are discussed. As the method offers considerable improvement over previous methods in cost, yield, practicality, applicability, and large-scale production, the new processes described here can be employed as the first practical methods for the economical production of various arylsulfur pentafluorides and their higher homologues, which could then open up a new era of "super-trifluoromethyl" arene chemistry and its applications in many areas.