ContaminantDB: Bithionol

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (4)XML

Record Information

Version

1.0

Creation Date

2016-05-22 03:31:16 UTC

Update Date

2026-05-14 18:10:37 UTC

Accession Number

CHEM016424

Identification

Common Name

Bithionol

Class

Small Molecule

Description

An aryl sulfide that is diphenyl sulfide in which each phenyl group is substituted at position 2 by hydroxy and at positions 3 and 5 by chlorine. A fungicide and anthelmintic, it was used in various topical drug products for the treatment of liver flukes, but withdrawn after being shown to be a potent photosensitizer with the potential to cause serious skin disorders.

Contaminant Sources

ToxCast & Tox21 Chemicals

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2,2'-Dihydroxy-3,3',5,5'-tetrachlorodiphenyl sulfide	ChEBI
2,2'-Thiobis(4,6-dichlorophenol)	ChEBI
2-Hydroxy-3,5-dichlorophenyl sulfide	ChEBI
Bis(3,5-dichloro-2-hydroxyphenyl) sulfide	ChEBI
Bithin	ChEBI
Bithionol sulfide	ChEBI
2,2'-Dihydroxy-3,3',5,5'-tetrachlorodiphenyl sulphide	Generator
2-Hydroxy-3,5-dichlorophenyl sulphide	Generator
Bis(3,5-dichloro-2-hydroxyphenyl) sulphide	Generator
Bithionol sulphide	Generator
Bitin	MeSH

Chemical Formula

C₁₂H₆Cl₄O₂S

Average Molecular Mass

356.052 g/mol

Monoisotopic Mass

353.884 g/mol

CAS Registry Number

97-18-7

IUPAC Name

2,4-dichloro-6-[(3,5-dichloro-2-hydroxyphenyl)sulfanyl]phenol

Traditional Name

bitin

SMILES

OC1=C(SC2=C(O)C(Cl)=CC(Cl)=C2)C=C(Cl)C=C1Cl

InChI Identifier

InChI=1S/C12H6Cl4O2S/c13-5-1-7(15)11(17)9(3-5)19-10-4-6(14)2-8(16)12(10)18/h1-4,17-18H

InChI Key

JFIOVJDNOJYLKP-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as diarylthioethers. These are organosulfur compounds containing a thioether group that is substituted by two aryl groups.

Kingdom

Organic compounds

Super Class

Organosulfur compounds

Class

Thioethers

Sub Class

Aryl thioethers

Direct Parent

Diarylthioethers

Alternative Parents

Substituents

Diarylthioether
1,3-dichlorobenzene
4-halophenol
2-halophenol
2-chlorophenol
4-chlorophenol
Thiophenol ether
Chlorobenzene
Halobenzene
Phenol
Monocyclic benzene moiety
Aryl halide
Aryl chloride
Benzenoid
Sulfenyl compound
Organooxygen compound
Organochloride
Organohalogen compound
Organic oxygen compound
Hydrocarbon derivative
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

aryl sulfide (CHEBI:3131 )
polyphenol (CHEBI:3131 )
dichlorobenzene (CHEBI:3131 )
organochlorine pesticide (CHEBI:3131 )
bridged diphenyl fungicide (CHEBI:3131 )
bridged diphenyl antifungal drug (CHEBI:3131 )

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.0017 g/L	ALOGPS
logP	6.12	ALOGPS
logP	5.97	ChemAxon
logS	-5.3	ALOGPS
pKa (Strongest Acidic)	4.89	ChemAxon
pKa (Strongest Basic)	-7.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	40.46 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	81.92 m³·mol⁻¹	ChemAxon
Polarizability	31.3 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0aor-0319000000-435a514099cbd5198501	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 45V, Negative	splash10-03dl-0900000000-684715f22d6e281ceb85	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 60V, Negative	splash10-03dl-0900000000-f1f9ecff11b990a79e9b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Negative	splash10-03dl-0900000000-c7ff76fb8e23902d9da0	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 15V, Negative	splash10-0udi-0109000000-3a73c9a59c804e137c76	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 75V, Negative	splash10-03kc-0900000000-8ef5e3d659c81e67ae2a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 90V, Negative	splash10-022i-2900000000-e4a0e278b9a2e67380a6	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 75V, Positive	splash10-03kc-0900000000-36cb9c1d601dab6970a4	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 90V, Positive	splash10-022i-2900000000-58c9d055e731de6ae0da	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0209000000-aff65a21aef363fc90c6	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udi-0009000000-894168ccc4396cacbb73	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03di-0900000000-159b93778441331acb03	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0009000000-8307400ffa40e9a68249	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-0109000000-684d16a2f39a2ea46a45	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-03di-1901000000-1dc626bf9e6509dd3387	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0209000000-d5fce7281e8b969c8497	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udi-0209000000-86d0032836270302c58b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-1942000000-a641fd0d439b9383ece7	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0009000000-2b3095a2931d5865ad23	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0f6x-1749000000-100437b9f8f4f2a74e15	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-001l-9800000000-22ac5226dad083ff8c6e	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

Not Available

Uses/Sources

Not Available

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

DB04813

HMDB ID

HMDB0249278

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Bithionol

Chemspider ID

2313

ChEBI ID

3131

PubChem Compound ID

Not Available

Kegg Compound ID

C07967

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

1. https://www.ncbi.nlm.nih.gov/pubmed/?term=17129675

2. https://www.ncbi.nlm.nih.gov/pubmed/?term=24495391

Bithionol (CHEM016424)

Structure for CHEM016424: Bithionol