Basic information
- Standard SMILES
Oc1ccc(Cl)cc1Sc1cc(Cl)ccc1O- InChIKey
ANUSOIHIIPAHJV-UHFFFAOYSA-N- Molecular formula
- C12H8Cl2O2S
- Average molar mass
- 287.2 g/mol
- Monoisotopic mass
- 285.9622061
Names & identifiers
- Preferred name
- Fenticlor
- IUPAC
- 4-chloro-2-(5-chloro-2-hydroxyphenyl)sulfanylphenol
- English name
- BIS(2-HYDROXY-5-CHLOROPHENYL) SULFIDE
- Molecular formula
- C12H8Cl2O2S
- Molecular weight
- 287.16
Names & synonyms
Show more names
Database identifiers
- CAS
97-24-5- PubChem CID
- 7329
- DTXSID
DTXSID4026137- ChEMBL
CHEMBL473535- ChEBI
CHEBI:556580- UNII
- D61659OVD0
- EC Number
- 202-568-7
- Nikkaji
- J4.947F
Properties
Computed structural properties
- XLogP
- 4.5
- Topological polar surface area
- 65.8 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 2
- Heavy atoms
- 17
- Formal charge
- 0
- Complexity
- 231
Experimental & physicochemical properties
Physical Description
2,2'-thiobis(4-chlorophenol) appears as white to cream-colored solid or pale yellow powder. White crystalline solid melting from 175.8-186.8 °C. Odorless and insoluble in water.
White to cream-colored solid or pale yellow powder; [CAMEO]
Physicochemical properties
- Melting point
- 175 °C · 175°C
- Boiling point
- 416.7 · 416.7±45.0 °C(Predicted)
- Density
- 1.4186 · 1.4186 (estimate)
- storage temp.
- Sealed in dry,Room Temperature
- form
- powder to crystal
- pka
- 7.91 · 7.91±0.48(Predicted)
- color
- White to Orange to Green
- Merck
- 14 · 14,4004
- Stability
- Stable. Incompatible with strong oxidizing agents.
- Cosmetics Ingredients Functions
- ANTIMICROBIAL
- LogP
- 4.4 · 4.400 (est)
- CAS DataBase Reference
- 97 · 97-24-5(CAS DataBase Reference)
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 61659 OVD0 · D61659OVD0
- EPA Substance Registry System
- Fenticlor (97-24-5)
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 315 · H315-H319
- Precautionary statements
- 264 · P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313
- Risk Statements
- 36 · 36/37/38
- Safety Statements
- 26 · 26-36/37/39
- RTECS
- 350000 · SN0350000
- HS Code
- 2930.9 · 2930.90.2900
- HazardClass
- IRRITANT
- Toxicity
- 250 mg/kg · LDLo intraperitoneal in mouse: 250mg/kg
Safety & regulation
GHS classification
GHS Classification
Danger
H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation];H317 (97.5%): May cause an allergic skin reaction [Warning Sensitization, Skin];H318 (97.5%): Causes serious eye damage [Danger Serious eye damage/eye irritation];H335 (97.5%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation];H413 (97.5%): May cause long lasting harmful effects to aquatic life [Hazardous to the aquatic environment, long-term hazard]
P261, P264, P264+P265, P271, P272, P273, P280, P302+P352, P304+P340, P305+P354+P338, P317, P319, P321, P332+P317, P333+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 40 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.;Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.
Hazard information
Reactivity Profile
2,2'-THIOBIS(4-CHLOROPHENOL) is incompatible with acids, diazo and azo compounds, halocarbons, isocyanates, aldehydes, alkali metals, nitrides, hydrides, and other strong reducing agents. Reactions with these materials may generate heat and toxic or flammable gases.
Safety & protection
First Aid
EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.;SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment.;INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing.;INGESTION: DO NOT INDUCE VOMITING. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. Be prepared to transport the victim to a hospital if advised by a physician. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. (NTP, 1992)
Nonfire Spill Response
SMALL SPILLS AND LEAKAGE: Should a spill occur while you are handling this chemical, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with 60-70% ethanol and transfer the dampened material to a suitable container. Use absorbent paper dampened with 60-70% ethanol to pick up any remaining material. Seal the absorbent paper, and any of your clothes, which may be contaminated, in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with 60-70% ethanol followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.;STORAGE PRECAUTIONS: You should store this material in a refrigerator. (NTP, 1992)
Personal Protective Equipment (PPE)
RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. (NTP, 1992)
Toxicology
Regulatory information
Safety data
- rtecs
- SN0350000
- hs_code
- 2930.90.2900
- Toxicity
- LDLo intraperitoneal in mouse: 250mg/kg
- risk_code
- 36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- safety_code
- 26-36/37/39
- hazard_class
- IRRITANT
- Hazard statements
- H315-H319
- Precautionary statements
- P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313
Chemistry & industry
Uses & manufacturing
Uses
Classification Code: Anti-infective, topical ; Antifungal agents [NLM, ChemIDplus] Used as a preservative in water circulation systems to prevent the growth of algae and slime; it has antimicrobial activity against bacteria, fungi, and algae; [Ullmann] Used in cosmetics (hair dressings and antifungal creams) sold outside the United States; also reported in workers handling thermoplastic resins; [Marks, p. 231]
Metal Machining [Category: Heat or Machine];Plastic Composites Manufacturing [Category: Industry];Dressing Hair [Category: Other]
Applications
UsesFungicide; especially used against Monosporium apiospermum: Reifferscheid, Seeliger, Dtsch. Med. Wochenschr. 80, 1841, 1850 (1955).
UsesFentichlor is a fungicide especially used against Monosporium apiospermum; topical antifungal and antibacterial agent in hairdressings, antifungal creams, and ointments; thermoplastic resin.
General DescriptionWhite to cream-colored solid or pale yellow powder. White crystalline solid melting from 175.8-186.8°C. Odorless and insolbule in water.
Preparation methods
PreparationFenticlor is produced (1) by the reaction of 4-chlorophenol with sulfur dichloride in the presence of AlCl3 or (2) by chlorination of 2,2'-thiobisphenol with chlorine in glacial acetic acid or with SO2Cl2 in dichlorobenzene. It shows a tendency to discoloration. Fenticlor has a broad range of antimicrobial action; it is, e.g., effective against bacteria, fungi, yeasts, and algae. Fenticlor is therefore used as a preservative for aqueous functional fluids and to control algae and slime in process water circulation systems.
Upstream & downstream products
Upstream raw materials
Downstream products
Suppliers44 total
Additional notes
DefinitionChEBI: An aryl sulfide having two 5-chloro-2-hydroxyphenyl groups attached to sulfur; an antiinfective drug mostly used in veterinary medicine.
Related reactions
Linked notes
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