844-26-8

Basic information

• Product Name: BITHIONOL SULFOXIDE
• Synonyms: 2,2’-sulfinylbis(4,6-dichloro-pheno;6,6’-sulfinylbis(2,4-dichlorophenol);bitins;disto-5-cogla;distobitin;sulphene;BITHIONOL SULFOXIDE;LABOTEST-BB LT00772303
• CAS NO: 844-26-8
• Molecular Formula: C₁₂H₆Cl₄O₃S
• Molecular Weight: 372.05
• EINECS: 212-679-2
• Mol File: 844-26-8.mol
• Article Data: 2

Chemical Properties

• Melting Point: 220 °C(Solv: methanol (67-56-1))
• Boiling Point: 532.7 °C at 760 mmHg
• Flash Point: 276 °C
• Appearance: Off white to tinch pink crystalline powder
• Density: 1.86 g/cm³
• PKA: 4.79±0.48(Predicted)
• CAS DataBase Reference: BITHIONOL SULFOXIDE(CAS DataBase Reference)
• NIST Chemistry Reference: BITHIONOL SULFOXIDE(844-26-8)
• EPA Substance Registry System: BITHIONOL SULFOXIDE(844-26-8)

Safety Data

• WGK Germany: 3
• RTECS: SM8800000
• Hazardous Substances Data: 844-26-8(Hazardous Substances Data)

Usage

General Description

Bithionol sulfoxide is a synthetic organic compound with the chemical formula C10H6Br2O2S. It is an antifungal and antibacterial agent that has been used in the treatment of various skin conditions, including acne and seborrheic dermatitis. Bithionol sulfoxide works by inhibiting the growth and reproduction of fungi and bacteria on the skin, making it effective in treating infections caused by these microorganisms. It is available in topical formulations and is generally well-tolerated, with limited side effects when used as directed. However, its use has become limited due to potential toxicity and environmental concerns, and it is no longer widely used in medical practice.

Synthetic route

2,4-dichlorophenol (120-83-2) → bithionol sulfoxide (844-26-8)

Conditions	Yield
With aluminum (III) chloride; thionyl chloride In dichloromethane at 0 - 22℃; for 8h; Inert atmosphere;	71%
With aluminium trichloride; thionyl chloride; 1,2-dichloro-ethane
With aluminum (III) chloride; thionyl chloride In dichloromethane at 22℃; for 8h;

bithionol (97-18-7) → bithionol sulfoxide (844-26-8)

Conditions	Yield
With dihydrogen peroxide; acetic acid at 60℃;
Multi-step reaction with 3 steps 1: acetic acid 2: aqueous H2O2; acetic acid 3: aq.-ethanolic NaOH View Scheme

bis-(2-acetoxy-3,5-dichloro-phenyl)-sulfoxide (861011-20-3) → bithionol sulfoxide (844-26-8)

Conditions	Yield
With sodium hydroxide

bis-(2-acetoxy-3,5-dichloro-phenyl)-sulfide (57548-01-3) → bithionol sulfoxide (844-26-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: aqueous H2O2; acetic acid 2: aq.-ethanolic NaOH View Scheme

bithionol sulfoxide (844-26-8) → 4,6,4',6'-tetrachloro-2,2'-sulfonyl-di-phenol (4568-36-9)

Conditions	Yield
With dihydrogen peroxide; acetic acid

bithionol sulfoxide (844-26-8) → bis-(2-acetoxy-3,5-dichloro-phenyl)-sulfoxide (861011-20-3)

bithionol sulfoxide (844-26-8) → bis-(2-acetoxy-3,5-dichloro-phenyl)-sulfone

Conditions	Yield
Multi-step reaction with 2 steps 1: glacial acetic acid; aqueous H2O2 View Scheme

bithionol sulfoxide (844-26-8) → bithionol (97-18-7)

Conditions	Yield
With acetic acid; zinc at 100℃; for 4h;
With acetic acid; zinc at 100℃; for 4h; Inert atmosphere;

bithionol sulfoxide (844-26-8) → C26H32Cl4N2O6S

Conditions	Yield
Multi-step reaction with 2 steps 1: acetic acid; zinc / 4 h / 100 °C / Inert atmosphere 2: potassium carbonate / N,N-dimethyl-formamide / 60 °C View Scheme

bithionol sulfoxide (844-26-8) → C16H16Cl4N2O2S

Conditions	Yield
Multi-step reaction with 3 steps 1: acetic acid; zinc / 4 h / 100 °C / Inert atmosphere 2: potassium carbonate / N,N-dimethyl-formamide / 60 °C 3: trifluoroacetic acid / dichloromethane / 18 h / 20 °C View Scheme

Upstream product

• 57548-01-3 bis-(2-acetoxy-3,5-dichloro-phenyl)-sulfide 
• 120-83-2 2,4-dichlorophenol 
• 861011-20-3 bis-(2-acetoxy-3,5-dichloro-phenyl)-sulfoxide 
• 97-18-7 bithionol 

Downstream Products

• 4568-36-9 4,6,4',6'-tetrachloro-2,2'-sulfonyl-di-phenol 
• 861011-20-3 bis-(2-acetoxy-3,5-dichloro-phenyl)-sulfoxide 
• 97-18-7 bithionol 

Relevant articles and documents

ANTIBIOTIC COMPOUNDS

The present application provides compounds and methods for treating bacterial infections, including bacterial infections caused by MRSA.