Basic information
- Standard SMILES
Cc1ccccc1S- InChIKey
LXUNZSDDXMPKLP-UHFFFAOYSA-N- Molecular formula
- C7H8S
- Average molar mass
- 124.21 g/mol
- Monoisotopic mass
- 124.03467126
Overview
2-Methylbenzenethiol is a thiol.
Names & identifiers
- Preferred name
- 2-Thiocresol
- IUPAC
- 2-methylbenzenethiol
- English name
- 2-Methylbenzenethiol
- Molecular formula
- C7H8S
- Molecular weight
- 124.2
Names & synonyms
Show more names
Database identifiers
- CAS
137-06-4- PubChem CID
- 8712
- DTXSID
DTXSID8047135- ChEMBL
CHEMBL3182595- ChEBI
CHEBI:178255- UNII
- 6FU2EGI4VS
- EC Number
- 205-276-8
- Nikkaji
- J5.627H
Properties
Computed structural properties
- XLogP
- 2.9
- Topological polar surface area
- 1 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 1
- Rotatable bonds
- 0
- Heavy atoms
- 8
- Formal charge
- 0
- Complexity
- 70.8
Experimental & physicochemical properties
Density
1.041 @ 20 °C/4 °C
1.054-1.059
Solubility
Sol in alcohol, ether; insol in water
(in ethanol)
Boiling Point
195 °C
194.00 to 196.00 °C. @ 760.00 mm Hg
194-195 °C
Melting Point
15 °C
15 °C
Physicochemical properties
- Melting point
- 10 · 10-12 °C(lit.)
- Boiling point
- 195 °C · 195 °C(lit.)
- Density
- 1.054 g/mL · 1.054 g/mL at 25 °C(lit.)
- refractive index
- 20 · n20/D 1.578(lit.)
- FEMA
- 3240 · 3240 | O-TOLUENETHIOL
- FLAVIS Number
- 12.027 · 12.027 | 2-Methylbenzene-1-thiol
- Flash point
- 147 °F · 147 °F
- storage temp.
- 30 °C · Store below +30°C.
- form
- Liquid
- pka
- 1 · pK1:6.64 (25°C)
- Specific Gravity
- 1.055 · 1.055
- color
- Clear colorless to pale yellow
- Odor
- 0.1 % · at 0.10 % in propylene glycol. meaty sulfurous onion garlic egg rubber
- Odor Type
- meaty
- biological source
- synthetic
- explosive limit
- 1.1 % · 1.1%(V)
- Water Solubility
- insoluble
- Sensitive
- Stench
- Merck
- 14 · 14,9325
- JECFA Number
- 528 · 528
- BRN
- 774068 · 774068
- Henry's Law Constant
- 2.7 · 2.7×10-2 mol/(m3Pa) at 25℃, HSDB (2015)
- InChI
- 1S/C7H8S/c1-6-4-2-3-5-7(6)8/h2-5,8H,1H3
- InChIKey
- LXUNZSDDXMPKLP-UHFFFAOYSA-N
- SMILES
- Cc1ccccc1S
- LogP
- 2.98 · 2.98
- Substances Added to Food (formerly EAFUS)
- O-TOLUENETHIOL
- CAS DataBase Reference
- 137 · 137-06-4(CAS DataBase Reference)
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 6 FU2EGI4VS · 6FU2EGI4VS
- NIST Chemistry Reference
- 2 · Benzenethiol, 2-methyl-(137-06-4)
- EPA Substance Registry System
- 2 · Benzenethiol, 2-methyl- (137-06-4)
- UNSPSC Code
- 12352100 · 12352100
- NACRES
- 22 · NA.22
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 302 · H302+H312+H332-H315-H319-H227
- Precautionary statements
- 501 · P501-P261-P270-P210-P271-P264-P280-P370+P378-P337+P313-P305+P351+P338-P362+P364-P332+P313-P301+P312+P330-P302+P352+P312-P304+P340+P312-P403+P235
- target organs
- Respiratory system
- PPE
- Eyeshields, Gloves, type ABEK (EN14387) respirator filter
- Hazard Codes
- Xi,Xn
- Risk Statements
- 37 · 37/38-41-36/37/38-20/21/22
- Safety Statements
- 26 · 26-39-36/37/39-23
- RIDADR
- 2810 · 2810
- WGK Germany
- 3 · 3
- RTECS
- 8750000 · XT8750000
- Hazard Note
- Harmful/Irritant/Stench
- TSCA
- TSCA listed
- HazardClass
- 6.1 · 6.1
- PackingGroup
- III
- HS Code
- 29309090 · 29309090
- Storage Class
- 10 · 10 - Combustible liquids
- Hazard Classifications
- 2 Skin · Eye Irrit. 2Skin Irrit. 2STOT SE 3
- Hazardous Substances Data
- 137 · 137-06-4(Hazardous Substances Data)
- Toxicity
- 50 · mouse,LD50,intraperitoneal,100mg/kg (100mg/kg),National Technical Information Service. Vol. AD277-689,
- Excepted Quantities
- Max Inner Pack (30g or 30ml) and Max Outer Pack (1Kg or 1L)
Safety & regulation
GHS classification
GHS Classification
Danger
H302 (97%): Harmful if swallowed [Warning Acute toxicity, oral]
P260, P264, P270, P280, P301+P317, P301+P330+P331, P302+P361+P354, P304+P340, P305+P354+P338, P316, P321, P330, P363, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 1454 reports by companies from 13 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory Information
Chemical: Benzenethiol, 2-methyl-
Regulation (EC) No 1831/2003 (amended)
Benzenethiol, 2-methyl-: Does not have an individual approval but may be used under an appropriate group standard
Hazards Summary
Emergency treatment: Ortho-cresol; o-Cresol is corrosive to tissues; After absorption by any route, it can cause CNS depression, respiratory failure, seizures, methemoglobinemia, hemolytic anemia, and liver and kidney damage; [HSDB] A severe skin, eye, and respiratory tract irritant; Inhalation of high concentrations may cause CNS depression and pulmonary edema; [CHEMINFO] Safe when used as a flavoring agent in food; [JECFA] An irritant; Inhalation may cause CNS effects (strong odor will minimize inhalation exposure); [Alfa Aesar MSDS] See Cresol, all isomers.
Safety & protection
Disposal Methods
SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.
Toxicology
Environmental Fate
TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 440(SRC), determined from a structure estimation method(2), indicates that 2-thiocresol is expected to have moderate mobility in soil(SRC). The pKa of 2-thiocresol is 6.64(3) indicating that the anionic form of 2-thiocresol will exist in slightly acidic to basic soils and anions are expected to have higher mobility than the neutral species(SRC). Volatilization of 2-thiocresol from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 3.6X10-4 atm-cu m/mole(SRC), using a fragment constant estimation method(4). However, 2-thiocresol in the anionic form will not volatilize. 2-Thiocresol is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 0.816 mm Hg(5).
AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 440(SRC), determined from an estimation method(2), indicates that 2-thiocresol is expected to slightly adsorb to suspended solids and sediment(SRC). Volatilization of the neutral species from water surfaces is expected(3) based upon an estimated Henry's Law constant of 3.6X10-4 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 3 hrs and 5.2 days, respectively(SRC). A pKa of 6.64(5) indicates that the anionic form of 2-thiocresol will exist in slightly acidic to basic waters and the anionic form will not volatilize from water(SRC). According to a classification scheme(6), an estimated BCF of 62(SRC), from an estimated log Kow of 3.2(7) and a regression-derived equation(8), suggests the potential for bioconcentration in aquatic organisms is moderate.
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 2-thiocresol, which has a vapor pressure of 0.816 mm Hg at 25 °C(2), is expected to exist solely in the vapor-phase in the ambient atmosphere. Vapor- phase 2-thiocresol is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 27 hrs(SRC), calculated from its rate constant of 1.4X10-11 cu cm/molecule-sec at 25 °C(SRC) determined using a structure estimation method(3). Although thiocresols may be susceptible to photolysis, sufficient experimental data are not available to predict the relative importance of their photolysis in the environment(SRC).
Soil Adsorption/Mobility
Using a structure estimation method based on molecular connectivity indices(1), the Koc for 2-thiocresol can be estimated to be 440(SRC). According to a classification scheme(2), this estimated Koc value suggests that 2-thiocresol is expected to have moderate mobility in soil. The pKa of 2-thiocresol is 6.64(3) indicating that the anionic form of 2-thiocresol will exist in slightly acidic to basic soils and anions are expected to have higher mobility than the neutral species(SRC). Volatilization from moist soil surfaces is not expected to be an important fate process for the anionic species.
Environmental Bioconcentration
An estimated BCF of 62 was calculated for 2-thiocresol(SRC), using an estimated log Kow of 3.2(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is moderate.
Volatilization from Water/Soil
The Henry's Law constant for 2-thiocresol is estimated as 3.6X10-4 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that 2-thiocresol is expected to volatilize from water surfaces(2). Based on this Henry's Law constant, the volatilization half-life of the neutral species from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec)(2) is estimated as 3 hrs(SRC). The volatilization half-life of the neutral species from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec)(2) is estimated as 5.2 days(SRC). A pKa of 6.64(3) for 2-thiocresol indicates that the anionic form of 2-thiocresol will exist in slightly acidic to basic waters and the anionic form is not expected to volatilize from water(SRC). 2-Thiocresol's Henry's Law constant(1) indicates that volatilization of the neutral species from moist soil surfaces may occur(SRC). However, 2-thiocresol in the anionic form is not expected to volatilize. 2-Thiocresol is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 0.816 mm Hg(4).
Environmental Abiotic Degradation
The rate constant for the vapor-phase reaction of 2-thiocresol with photochemically-produced hydroxyl radicals has been estimated as 1.4X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half- life of about 27 hrs at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). 2-Thiocresol is not expected to undergo hydrolysis in the environment due to the lack of hydrolyzable functional groups(2). Although thiocresols may be susceptible to photolysis, sufficient experimental data are not available to predict the relative importance of their photolysis in the environment(SRC).
Environmental Fate/Exposure Summary
2-Thiocresol's possible production as an antiseptic and as a bleach in the manufacture of latex may result in its release to the environment through various waste streams. If released to air, a vapor pressure of 0.816 mm Hg at 25 °C indicates 2-thiocresol will exist solely in the vapor phase in the ambient atmosphere. Vapor-phase 2-thiocresol will be degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals; the half-life for this reaction in air is estimated to be 27 hrs. Although thiocresols may be susceptible to photolysis, sufficient experimental data are not available to predict the relative importance of their photolysis in the environment. If released to soil, 2-thiocresol is expected to have moderate mobility based upon an estimated Koc of 440. The pKa of 2-thiocresol is 6.64 indicating that the anionic form of 2-thiocresol will exist in slightly acidic to basic soils and these anions are expected to have higher mobility than the neutral species. Volatilization of the neutral species from moist soil surfaces is expected to be an important fate process based upon an estimated Henry's Law constant of 3.6X10-4 atm-cu m/mole. However, volatilization of the anionic species from moist soil surfaces does not occur. 2-Thiocresol is not expected to volatilize from dry soil surfaces based upon its vapor pressure. If released into water, 2-thiocresol is expected to slightly adsorb to suspended solids and sediment based upon the estimated Koc. Volatilization of the neutral species from water surfaces is expected to be an important fate process based upon this compound's estimated Henry's Law constant. However, based on the pKa, the anionic form of 2-thiocresol will exist in slightly acidic to basic waters and the anionic form does not volatilize from water. Estimated volatilization half-lives of the neutral species for a model river and model lake are 3 hrs and 5.2 days, respectively. An estimated BCF of 62 suggests the potential for bioconcentration in aquatic organisms is moderate. Hydrolysis is not expected to occur due to the lack of hydrolyzable functional groups. Occupational exposure to 2-thiocresol may occur through inhalation and dermal contact with this compound at workplaces where 2-thiocresol is produced or used. (SRC)
Safety data
- PPE
- Eyeshields, Gloves, type ABEK (EN14387) respirator filter
- wgk
- 3
- tsca
- TSCA listed
- rtecs
- XT8750000
- ridadr
- 2810
- hs_code
- 29309090
- Toxicity
- mouse,LD50,intraperitoneal,100mg/kg (100mg/kg),National Technical Information Service. Vol. AD277-689,
- risk_code
- 37/38-41-36/37/38-20/21/22
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xi,Xn
- hazard_note
- Harmful/Irritant/Stench
- safety_code
- 26-39-36/37/39-23
- hazard_class
- 6.1
- Storage Class
- 10 - Combustible liquids
- packing_group
- III
- target organs
- Respiratory system
- Hazard statements
- H302+H312+H332-H315-H319-H227
- Excepted Quantities
- Max Inner Pack (30g or 30ml) and Max Outer Pack (1Kg or 1L)
- Hazard Classifications
- Eye Irrit. 2Skin Irrit. 2STOT SE 3
- Precautionary statements
- P501-P261-P270-P210-P271-P264-P280-P370+P378-P337+P313-P305+P351+P338-P362+P364-P332+P313-P301+P312+P330-P302+P352+P312-P304+P340+P312-P403+P235
- Hazardous Substances Data
- 137-06-4(Hazardous Substances Data)
Chemistry & industry
Pharmacology
Uses & manufacturing
Uses
Used as a bleach in latex manufacturing, an antiseptic, and a dermatologic agent; [HSDB] Used as an intermediate in the manufacture of chemicals; [CHEMINFO] Used as flavoring agent; [JECFA]
Using Disinfectants or Biocides [Category: Clean]
Antiseptic; dermatologic /unspecified isomer/
As a bleach in the manufacture of latex /tolyl mercaptan, isomer not stated/
U.S. Production
(1977) NOT PRODUCED COMMERCIALLY IN USA
(1979) NOT PRODUCED COMMERCIALLY IN USA
Use Classification
Fragrance Ingredients
Flavoring Agents -> JECFA Flavorings Index
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
Applications
OccurrenceReported found in coffee
Uses2-Thiocresol performs a fungicidal and inhibitory activity against Histoplasma capsulatum. Reagent for molecular modeling and preparation of 4-hydroxy-5,6-dihydropyrones as inhibitors of HIV protease.
Upstream & downstream products
Upstream raw materials
Downstream products
Suppliers50 total
Additional notes
DefinitionChEBI: 2-Methylbenzenethiol is a thiol.
Related reactions
Linked notes
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