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4-Methylbenzenethiol

HCID 7811
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Basic informationNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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Basic information

CAS
106-45-6
Standard SMILES
Cc1ccc(S)cc1
InChIKey
WLHCBQAPPJAULW-UHFFFAOYSA-N
Molecular formula
C7H8S
Average molar mass
124.21 g/mol
Monoisotopic mass
124.03467143

Names & identifiers

Preferred name
4-Methylbenzenethiol
IUPAC
4-methylbenzenethiol
English name
p-Toluenethiol
Molecular formula
C7H8S
Molecular weight
124.2

Names & synonyms

4-Methylbenzenethiolp-Thiocresol106-45-6p-Toluenethiol4-Methylthiophenol4-THIOCRESOLp-Tolyl mercaptan4-Toluenethiolp-Methylthiophenolp-Tolylthiolp-Mercaptotoluenep-Thiolcresol
Show more names
para-thiocresolp-Thiocreso4-MERCAPTOTOLUENE4-TOLYL MERCAPTAN
p-Methylbenzenethiol1-Mercapto-4-methylbenzenep-Methylphenyl mercaptan4-Methylphenyl mercaptanUSAF EK-5104-MethylphenylmercaptanToluene, 4-mercapto-DTXSID5048188

Database identifiers

CAS
106-45-6
PubChem CID
7811
DTXSID
DTXSID5048188
ChEMBL
CHEMBL119359
UNII
6L2WW9XYZO
EC Number
203-399-1
Nikkaji
J5.051B

Properties

Computed structural propertiesFilling in

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
62

Experimental & physicochemical properties

Density1.2475 @ 55°C
Color/FormLeaflets
SolubilityInsol in water; sol in alcohol, ether
Flash Point68 °C
Boiling Point · 2 items

195 °C @ 760 mm Hg

195 °C @760 [mm Hg]

DecompositionWhen heated to decomposition it emits toxic fumes of /sulfur oxides/.
Melting Point43-44 °C
Odor ThresholdOdor detection in air= 1.0X10-4 mg/l (gas) chemically pure
Vapor Pressure · 3 items

0.8 [mmHg]

0.807 mm Hg @ 25 °C

0.807 [mm Hg] @25 °C

Physical DescriptionWhite solid with an extremely offensive odor; [CHEMINFO] Crystalline solid with a stench; [Alfa Aesar MSDS]

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 5 items

Danger

H301 (25%): Toxic if swallowed [Danger Acute toxicity, oral];H302 (62.5%): Harmful if swallowed [Warning Acute toxicity, oral];H311 (25%): Toxic in contact with skin [Danger Acute toxicity, dermal];H312 (62.5%): Harmful in contact with skin [Warning Acute toxicity, dermal];H315 (56.2%): Causes skin irritation [Warning Skin corrosion/irritation];H318 (25%): Causes serious eye damage [Danger Serious eye damage/eye irritation];H319 (62.5%): Causes serious eye irritation [Warning Serious eye damage/eye irritation];H330 (18.8%): Fatal if inhaled [Danger Acute toxicity, inhalation];H331 (12.5%): Toxic if inhaled [Danger Acute toxicity, inhalation];H332 (56.2%): Harmful if inhaled [Warning Acute toxicity, inhalation];H335 (50%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

P260, P261, P262, P264, P264+P265, P270, P271, P280, P284, P301+P316, P301+P317, P302+P352, P304+P340, P305+P351+P338, P305+P354+P338, P316, P317, P319, P320, P321, P330, P332+P317, P337+P317, P361+P364, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 16 reports by companies from 10 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

Regulatory Information4-Methylthiophenol: Does not have an individual approval but may be used under an appropriate group standard
Hazards SummaryEmergency treatment: Phenol and related agents; [HSDB] An irritant; Inhalation may cause CNS effects (strong odor will minimize inhalation exposure); [Alfa Aesar MSDS] See Phenol.

Chemistry & industry

Uses & manufacturing

Uses · 4 items

Used as an antiseptic, dermatologic agent, and bleach in the manufacture of latex; [HSDB] Used as an intermediate in the manufacture of chemicals; [CHEMINFO]

Using Disinfectants or Biocides [Category: Clean]

Antiseptic; dermatologic /Unspecified isomer/

As a bleach in the manufacture of latex /tolyl mercaptan, isomer not stated/

General Manufacturing InformationBenzenethiol, 4-methyl-: ACTIVE

Applications

Usesp-Thiocresol is used as a pharmaceutical intermediate.

Upstream & downstream products

Upstream raw materials

O-ethyl hydrogen dithiocarbonateP-TOLYL DISULFIDESodium p-toluenesulfinate4-Tolylboronic acid4-Methylaniline hydrochloride2-MethylbenzenethiolDimethyl disulfidep-Toluenesulfonamide(4-Methylthio)toluenep-Toluenesulfonic acid4-Chlorotoluenep-Toluidine

Related reactions

214 records
New reaction record
HRID 6690 reaction equation
HRID 6690As reactantuspto-grants-2006_08
HRID 9886 reaction equation
HRID 9886As reactantuspto-grants-2006_08
HRID 14357 reaction equation
HRID 14357As reactantuspto-grants-2010_06
HRID 15207 reaction equation
HRID 15207As reactantuspto-grants-2010_06
HRID 15209 reaction equation
HRID 15209As reactantuspto-grants-2010_06
HRID 15213 reaction equation
HRID 15213As reactantuspto-grants-2010_06
HRID 28115 reaction equation
HRID 28115As reactantuspto-grants-1980_09
HRID 64483 reaction equation
HRID 64483As reactantuspto-grants-2016_09
Page 1 of 27

Compound notes

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Dissociation ConstantspKa= 6.82 @ 25 °C
Kovats Retention Index · 2 items

1082

1048;1048;1047;1048

Physicochemical properties

Melting point
84 · 84-86(lit.)
Boiling point
195 °C · 195 °C(lit.)
Density
1.022 · 1.0220
vapor density
6.2 · 6.2 (vs air)
vapor pressure
10 mm · 10 mm Hg ( 71 °C)
refractive index
1.542 · 1.5420 (estimate)
Flash point
155 °F · 155 °F
storage temp.
30 °C · Store below +30°C.
solubility
Chloroform (Slightly), Methanol (Slightly)
form
Fused Solid
pka
1 · pK1:6.52 (25°C)
color
White to yellow
Water Solubility
slightly soluble
Sensitive
Stench
Merck
14 · 14,9325
BRN
605761 · 605761
Henry's Law Constant
2.7 · 2.7×10-2 mol/(m3Pa) at 25℃, HSDB (2015)
Stability
Smelly, Air Sensitive
InChI
1S/C7H8S/c1-6-2-4-7(8)5-3-6/h2-5,8H,1H3
InChIKey
WLHCBQAPPJAULW-UHFFFAOYSA-N
SMILES
Cc1ccc(S)cc1
LogP
2.98 · 2.980 (est)
CAS DataBase Reference
106 · 106-45-6(CAS DataBase Reference)
EWG's Food Scores
1 · 1
FDA UNII
6 L2WW9XYZO · 6L2WW9XYZO
NIST Chemistry Reference
4 · Benzenethiol, 4-methyl-(106-45-6)
EPA Substance Registry System
4 · Benzenethiol, 4-methyl- (106-45-6)
UNSPSC Code
12352105 · 12352105
NACRES
23 · NA.23
Symbol(GHS)
6 · GHS06
Signal word
Danger
Hazard statements
301 · H301+H311+H331-H315-H319
Precautionary statements
501 · P501-P261-P270-P271-P264-P280-P337+P313-P305+P351+P338-P361+P364-P332+P313-P301+P310+P330-P302+P352+P312-P304+P340+P311-P403+P233-P405
PPE
95 · Eyeshields, Gloves, type N95 (US)
Hazard Codes
Xi,Xn
Risk Statements
36 · 36/37/38-20/21/22
Safety Statements
26 · 26-36-36/37/39-60-36/37-9
RIDADR
2811 · 2811
WGK Germany
3 · 3
RTECS
8925000 · XT8925000
F
13 · 13
Hazard Note
Harmful/Stench
TSCA
TSCA listed
HazardClass
6.1 · 6.1
PackingGroup
III
HS Code
29309070 · 29309070
Storage Class
11 · 11 - Combustible Solids
Hazard Classifications
2 · Eye Irrit. 2
Hazardous Substances Data
106 · 106-45-6(Hazardous Substances Data)
Toxic Combustion ProductsWhen heated to decomp, it emits toxic fumes of /sulfur oxides/.
Hazard Classes and CategoriesAcute Tox. 3 (25%);Acute Tox. 4 (62.5%);Acute Tox. 3 (25%);Acute Tox. 4 (62.5%);Skin Irrit. 2 (56.2%);Eye Irrit. 2 (62.5%);Acute Tox. 2 (18.8%);Acute Tox. 3 (12.5%);Acute Tox. 4 (56.2%);STOT SE 3 (50%)

Safety & protection

Disposal Methods · 1 item

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.

Protective Action Criteria (PAC) · 3 items

0.66 [mg/m3]

7.2 [mg/m3]

43 [mg/m3]

Toxicology

Environmental Fate · 3 items

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 430(SRC), determined from a structure estimation method(2), indicates that 4-thiocresol is expected to have moderate mobility in soil(SRC). The pKa of 4-thiocresol is 6.82(3) indicating that the anionic form of 4-thiocresol will exist in slightly acidic to basic soils and anions are expected to have higher mobility than the neutral species(SRC). Volatilization of 4-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, 4-thiocresol in the anionic form will not volatilize. 4-Thiocresol is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 0.807 mm Hg(5).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 430(SRC), determined from an estimation method(2), indicates that 4-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 6.82(5) indicates that the anionic form of 4-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), 4-thiocresol, which has a vapor pressure of 0.807 mm Hg at 25 °C(2), is expected to exist solely in the vapor-phase in the ambient atmosphere. Vapor-phase 4-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).

Adverse EffectsNeurotoxin - Other CNS neurotoxin
Effluent ConcentrationsThe concentration of 4-thiocresol in a raw sludge from a wood preservation operation has been reported to be 0.52 g/l(1).
Soil Adsorption/Mobility · 1 item

Using a structure estimation method based on molecular connectivity indices(1), the Koc for 4-thiocresol can be estimated to be 430(SRC). According to a classification scheme(2), this estimated Koc value suggests that 4-thiocresol is expected to have moderate mobility in soil. The pKa of 4-thiocresol is 6.82(3) indicating that the anionic form of 4-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.

Artificial Pollution Sources4-Thiocresol's possible production as an antiseptic(1) may result in its release to the environment through various waste streams(SRC).
Environmental Bioconcentration · 1 item

An estimated BCF of 62 was calculated for 4-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 · 1 item

The Henry's Law constant for 4-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 4-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 6.82(3) for 4-thiocresol indicates that the anionic form of 4-thiocresol will exist in slightly acidic to basic waters and the anionic form is not expected to volatilize from water(SRC). 4-Thiocresol's Henry's Law constant(1) indicates that volatilization of the neutral species from moist soil surfaces may occur(SRC). However, 4-thiocresol in the anionic form is not expected to volatilize. 4-Thiocresol is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 0.807 mm Hg(4).

Non-Human Toxicity ExcerptsPoisonous by intraperitoneal route.
Environmental Abiotic Degradation · 1 item

The rate constant for the vapor-phase reaction of 4-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 approximately 27 hrs at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). 4-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).

Probable Routes of Human ExposureOccupational exposure to 4-thiocresol may occur through inhalation and dermal contact with this compound at workplaces where 4-thiocresol is produced. (SRC)
Environmental Fate/Exposure Summary · 1 item

4-Thiocresol's possible production as an antiseptic may result in its release to the environment through various waste streams. If released to air, a vapor pressure of 0.807 mm Hg at 25 °C indicates 4-thiocresol will exist solely in the vapor phase in the ambient atmosphere. Vapor-phase 4-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, 4-thiocresol is expected to have moderate mobility based upon an estimated Koc of 430. The pKa of 4-thiocresol is 6.82 indicating that the anionic form of 4-thiocresol will exist in slightly acidic to basic soils and these anions are expected to have higher mobility than the neutral species. Volatilization 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 will not occur. 4-Thiocresol is not expected to volatilize from dry soil surfaces based upon its vapor pressure. If released into water, 4-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 4-thiocresol will exist in slightly acidic to basic waters and the anionic form will 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 expec

Non-Human Toxicity ValuesLD50 Mouse ip 200 mg/kg

Regulatory information

Regulatory Information4-Methylthiophenol: Does not have an individual approval but may be used under an appropriate group standard

Safety data

F
13
PPE
Eyeshields, Gloves, type N95 (US)
wgk
3
tsca
TSCA listed
rtecs
XT8925000
ridadr
2811
hs_code
29309070
risk_code
36/37/38-20/21/22
Signal word
Danger
Symbol(GHS)
GHS06
hazard_code
Xi,Xn
hazard_note
Harmful/Stench
safety_code
26-36-36/37/39-60-36/37-9
hazard_class
6.1
Storage Class
11 - Combustible Solids
packing_group
III
Hazard statements
H301+H311+H331-H315-H319
Hazard Classifications
Eye Irrit. 2
Precautionary statements
P501-P261-P270-P271-P264-P280-P337+P313-P305+P351+P338-P361+P364-P332+P313-P301+P310+P330-P302+P352+P312-P304+P340+P311-P403+P233-P405
Hazardous Substances Data
106-45-6(Hazardous Substances Data)
Sodium p-toluenesulfonate

Downstream products

5-Methyl-1-benzothiophene-2-carbaldehydep-Toluenesulfinic acid2-[(4-Methylphenyl)thio]-5-nitrobenzaldehyde6-Nitroveratraldehyde4-Toluenesulfonylacetic acid2-[(4-Methylphenyl)sulfonyl]ethanol2,2'-[[9,10-Dihydro-9,10-dioxo-6-[(4-methylphenyl)thio]anthracene-1,4-diyl]diimino]bis[5-methylbenzenesulfonic acid sodium] salt