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2,3,6-Trimethylphenol

HCID 17016
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Grundinformationen

CAS
2416-94-6
Standard-SMILES
Cc1ccc(C)c(O)c1C
InChIKey
QQOMQLYQAXGHSU-UHFFFAOYSA-N
Summenformel
C9H12O
Durchschnittliche Molmasse
136,19 g/mol
Monoisotopische Masse
136,088815

Überblick

2,3,6-Trimethylphenol is a hydroxytoluene.

Namen und Bezeichner

Bevorzugter Name
2,3,6-Trimethylphenol
IUPAC
2,3,6-trimethylphenol
Lokaler Name
2,3,6-Trimethylphenol
Englischer Name
2,3,6-Trimethylphenol
Summenformel
C9H12O
Molmasse
136.19

Namen und Synonyme

2,3,6-TRIMETHYLPHENOL2416-94-63-HydroxypseudocumenePhenol, 2,3,6-trimethyl-1-Hydroxy-2,3,6-trimethylbenzeneDTXSID6022187HSDB 5876UNII-05WKL2L5LJEINECS 219-330-305WKL2L5LJNSC 91509NSC-91509
Weitere Namen anzeigen
2,3,6-TrimethylpenolPhenol,2,3,6-trimethyl-FEMA 39632,3,6-trimethylTrimethylphenol,95%2,3,6-Trimethy/pheno2,3,6-trimethyl-phenoIbrutinib Impurity 151
DTXCID602187FEMA NO. 3963EC 219-330-32,3,6-TRIMETHYLPHENOL [FHFI]2,3,6-TRIMETHYLPHENOL [HSDB]3HydroxypseudocumeneRefChem:81455Phenol, 2,3,6trimethyl

Datenbank-Bezeichner

CAS
2416-94-6
PubChem CID
17016
DTXSID
DTXSID6022187
ChEMBL
CHEMBL3182738
ChEBI
CHEBI:169180
UNII
05WKL2L5LJ
EC Number
219-330-3
Nikkaji
J116.743J

Eigenschaften

Berechnete StruktureigenschaftenWird ergänzt

XLogP
2,7
Polarare Oberfläche (TPSA)
20,2 Ų
H-Brücken-Donoren
1
H-Brücken-Akzeptoren
1
Frei drehbare Bindungen
0
Schwere Atome
10
Formalladung
0
Komplexität
111

Experimentelle und physikochemische Eigenschaften

Chemical ClassesOther Classes -> Phenols
SpringerMaterials Properties13C nuclear magnetic resonance spectrum
LogP · 3 Einträge

log Kow = 2.67

2.67

2.67

Food AdditivesFLAVORING AGENT OR ADJUVANT -> FDA Substance added to food
Flavoring AgentsEU Flavoring substances
Solubility · 5 Einträge

Very soluble in ethanol, ether, benzene.

Water solubility of 1,580 mg/l at 25 °C.

1.58 mg/mL at 25 °C

insoluble in water

50% soluble in ethyl alcohol (in ethanol)

Flash Point100 °C
Boiling Point · 3 Einträge

226 °C

226.00 °C. @ 760.00 mm Hg

228 °C

Melting Point · 2 Einträge

Sicherheit und Regulatorisches

Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.

GHS-Klassifizierung

GHS Classification · 6 Einträge

Danger

H314 (29.7%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]

P260, P261, P264, P264+P265, P272, P280, P301+P330+P331, P302+P352, P302+P361+P354, P304+P340, P305+P354+P338, P316, P317, P321, P332+P317, P333+P317, P362+P364, P363, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 303 reports by companies from 10 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Warning

H302: Harmful if swallowed [Warning Acute toxicity, oral]

Gefahrenhinweise

Regulatory Information · 4 Einträge

Chemical: Phenol, 2,3,6-trimethyl-

Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)

REACH registered substance: 2,3,6-trimethylphenol (EC: 219-330-3)

Phenol, 2,3,6-trimethyl-: Does not have an individual approval but may be used under an appropriate group standard

Hazards Summary · 1 Eintrag

Safe when used as a flavoring agent in food; [JECFA] A corrosive substance that can cause injury to the skin, eyes, and respiratory tract; Inhalation may cause chemical pneumonitis and pulmonary edema; Readily absorbed through skin; [MSDSonline] See Phenol.

Hazard Classes and Categories · 2 Einträge

Skin Corr. 1C (29.7%)

Acute toxicity (Oral) - Category 4

Sicherheit und Schutzausrüstung

Disposal Methods · 2 Einträge

Chemie und Industrie

Pharmakologische Informationen

Cellular LocationsMembrane

Verwendung und Herstellung

Uses · 2 Einträge

Used as a starting material for Vitamin E and as a co-monomer for the modification of polyphenylene oxide resins; [HSDB]

Starting material for Vitamin E; co-monomer for the modification of polyphenylene oxide resins.

U.S. Imports(1982) 3.29X10+7 G (PRINCIPAL CUSTOMS DISTRIBUTORS)
U.S. Production · 2 Einträge

(1977) AT LEAST 4.54X10+8 G

(1982) PROBABLY GREATER THAN 2.27X10+6 G

Methods of ManufacturingPrepared by gas phase methylation of m-cresol with methanol at 300-460 °C under normal pressures on ortho-selective catalysts. Also by methylation of 2,6-xylenol on gamma aluminum oxide.
Use Classification · 3 Einträge

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

Flavoring Agents -> JECFA Flavorings Index

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

General Manufacturing Information · 3 Einträge

Phenol, 2,3,6-trimethyl-: ACTIVE

FUNGICIDAL CONSTITUENTS AGAINST RHIZOCTONIA SOLANI & ALTERNARIA MALI WERE ISOLATED FROM KUNTAN (CALCINED RICE CHAFF) SMOKE. THE FUNGICIDAL CONSTITUENTS WERE PHENOLICS, INCLUDING 2,3,6-TRIMETHYLPHENOL.

2,3,6-Trimethylphenol is formed in small quantities as byproducts in the production of cresol and xylenol.

Anwendungen · 1 Eintrag

Verwenden2,3,6-Trimethylphenol is used as intermediate for synthetic vitamin E. It is used for manufacturing 2, 3, 5-Trimethylhydroquinone. It is used as intermediate for antioxidants and plastics. It is used as a comonomer for the modification of polyphenylene oxide resins.

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58 °C

63.5 - 64 °C

Vapor Pressure · 2 Einträge

0.03 [mmHg]

0.035 mm Hg at 25 °C

Physical Description · 3 Einträge

Solid; [IUCLID] Light yellow crystalline lumps; [MSDSonline]

Solid

White crystalline solid

Collision Cross Section130.9 Ų [M-H]- [CCS Type: DT; Buffer gas: N2; Ionization: ESI-; Dataset: TOXCAST; Source Identifier: DTXSID6022187]

Physikochemische Eigenschaften

Schmelzpunkt
59 · 59-62 °C(lit.)
Siedepunkt
215 °C · 215°C
Dichte
0.94 · 0.940
Brechungsindex
1.5115 · 1.5115 (estimate)
FEMA
3963 · 3963 | 2,3,6-TRIMETHYLPHENOL
Flammpunkt
100 · 100
storage temp.
Inert atmosphere,Room Temperature
Löslichkeit
0.1 g/mL, · methanol: 0.1 g/mL, clear
pka
10.77 · 10.77±0.15(Predicted)
Aggregatzustand
powder to crystal
Farbe
White to Orange to Green
Geruch (Odor)
char. antiseptic odor
Wasserlöslichkeit
1.42 g/L · 1.42g/L at 25℃
JECFA Number
737 · 737
Henry's Law Constant
2.5 · 2.5×100 mol/(m3Pa) at 25℃, Duchowicz et al. (2020)
Major Application
flavors and fragrances
Kosmetik-Inhaltsstoffe Funktionen
PERFUMING
InChI
1S/C9H12O/c1-6-4-5-7(2)9(10)8(6)3/h4-5,10H,1-3H3
InChIKey
QQOMQLYQAXGHSU-UHFFFAOYSA-N
SMILES
Cc1ccc(C)c(O)c1C
LogP
2.8 · 2.80
CAS Datenbank
2416 · 2416-94-6(CAS DataBase Reference)
NIST chemische Informationen
2 · Phenol, 2,3,6-trimethyl-(2416-94-6)
EPA chemische Informationen
2 · 2,3,6-Trimethylphenol (2416-94-6)

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.

The following wastewater treatment technologies have been investigated for trimethylphenol: Activated carbon. /Trimethylphenol/

Personal Protective Equipment (PPE) · 3 Einträge

ORGANIC CANISTER MASK; FACE SHIELD; RUBBER GLOVES; OTHER PROTECTIVE CLOTHING TO PREVENT CONTACT WITH SKIN. /DIMETHYL PHENOL/

/IN FIRE CONDITIONS/ WEAR GOGGLES AND SELF CONTAINED BREATHING APPARATUS. /DIMETHYL PHENOL/

Wear appropriate chemical protective gloves, boots and goggles. /Dimethyl phenol/

Toxikologische Informationen

Environmental Fate · 3 Einträge

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 700(SRC), determined from a log Kow of 2.67(2) and a regression-derived equation(3), indicates that 2,3,6-trimethylphenol is expected to have low mobility in soil(SRC). Volatilization of 2,3,6-trimethylphenol from moist soil surfaces is expected to occur slowly(SRC) given an estimated Henry's Law constant of 3.9X10-6 atm-cu m/mole(SRC) from its vapor pressure, 0.035 mm Hg(4), and water solubility, 1,580 mg/l at 25 °C(5). 2,3,6-Trimethylphenol is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(4). 2,3,6-Trimethylphenol, at an initial concentration of 0.37 mg/l, underwent no degradation when incubated in coal tar-contaminated groundwater in an anaerobic digester for 8 weeks(6), suggesting that biodegradation under anaerobic conditions will not be important; biodegradability under aerobic conditions is unknown(SRC).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 700(SRC), determined from a log Kow of 2.67(2) and a regression-derived equation(3), indicates that 2,3,6-trimethylphenol is expected to adsorb to suspended solids and sediment in water(SRC). Volatilization from water surfaces is expected to occur(3) based upon an estimated Henry's Law constant of 3.9X10-6 atm-cu m/mole(SRC) from its vapor pressure, 0.035 mm Hg(4), and water solubility, 1,580 mg/l at 25 °C(5). Volatilization half-lives for a model river and model lake are 11 and 84 days, respectively(SRC), using an estimation method(3). According to a classification scheme(6), an estimated BCF value of 60(SRC), from a log Kow of 2.67(2) and a regression-derived equation(3), suggests that bioconcentration in aquatic organisms is moderate(SRC). 2,3,6-Trimethylphenol, at an initial concentration of 0.37 mg/l, underwent no degradation when incubated in coal tar-contaminated groundwater in an anaerobic digester for 8 weeks(7).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 2,3,6-trimethylphenol, which has a vapor pressure of 0.035 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase 2,3,6-trimethylphenol 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 3 hours(SRC) from its estimated rate constant of 1.3X10-10 cu cm/molecule-sec at 25 °C(3).

Adverse EffectsDermatotoxin - Skin burns.
Soil Adsorption/Mobility · 1 Eintrag

The Koc of 2,3,6-trimethylphenol is estimated as 700(SRC), using a log Kow of 2.67(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that 2,3,6-trimethylphenol is expected to have low mobility in soil(SRC).

Artificial Pollution Sources · 1 Eintrag

2,3,6-Trimethylphenol's production and use as a comonomer for the modification of polyphenylene oxide resins and as a starting material in vitamin E synthesis(1) may result in its release to the environment through various waste streams(SRC).

Environmental Biodegradation2,3,6-Trimethylphenol, at an initial concentration of 0.37 mg/l, underwent no degradation when incubated in coal tar-contaminated groundwater in an anaerobic digester for 8 weeks(1).
Environmental Bioconcentration · 1 Eintrag

An estimated BCF of 60 was calculated for 2,3,6-trimethylphenol(SRC), using a log Kow of 2.67(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(SRC).

Volatilization from Water/Soil · 1 Eintrag

The Henry's Law constant for 2,3,6-trimethylphenol is estimated as 3.9X10-6 atm-cu m/mole(SRC) from its experimental values for vapor pressure, 0.035 mm Hg(1), and water solubility, 1,580 mg/l(2). This Henry's Law constant indicates that 2,3,6-trimethylphenol is expected to volatilize from water surfaces(3). Based on this Henry's Law constant, the volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec)(3) is estimated as 11 days(SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec)(3) is estimated as approximately 84 days(SRC). 2,3,6-Trimethylphenol's estimated Henry's Law constant(1,2) indicates that volatilization from moist soil surfaces may occur(SRC). 2,3,6-Trimethylphenol is not expected to volatilize from dry soil surfaces(SRC) based upon the vapor pressure of this compound(1).

Environmental Abiotic Degradation · 1 Eintrag

The rate constant for the vapor-phase reaction of 2,3,6-trimethylphenol with photochemically-produced hydroxyl radicals has been estimated as 1.3X10-10 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 3 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). 2,3,6-Trimethylphenol is not expected to undergo hydrolysis in the environment due to the lack of hydrolyzable functional groups(2).

Probable Routes of Human ExposureOccupational exposure to 2,3,6-trimethylphenol may occur through inhalation and dermal contact with this compound at workplaces where 2,3,6-trimethylphenol is produced or used. (SRC)
Environmental Water Concentrations · 1 Eintrag

GROUNDWATER: 2,3,6-Trimethylphenol was detected in groundwater in the vicinity of the wood treatment facilities of the American Creosote Works in Pensacola, FL, at max concns of 0.67 ppm (6 m), 0.12 ppm (12 m), 0.28 ppm (18 m), 0.15 ppm (24 m)(1). 2,3,6-Trimethylphenol was identified, not quantified, in an aquifer in St. Louis Park, MN which was contaminated during the operation of a coal tar distillation and wood treatment facility(2).

Environmental Fate/Exposure Summary · 1 Eintrag

2,3,6-Trimethylphenol's production and use as a comonomer for the modification of polyphenylene oxide resins and as a starting material in vitamin E synthesis may result in its release to the environment through various waste streams. If released to air, a vapor pressure of 0.035 mm Hg at 25 °C indicates 2,3,6-trimethylphenol will exist solely as a vapor in the ambient atmosphere. Vapor-phase 2,3,6-trimethylphenol 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 3 hours. If released to soil, 2,3,6-trimethylphenol is expected to have low mobility based upon an estimated Koc of 700. Volatilization from moist soil surfaces is expected to occur slowly based upon an estimated Henry's Law constant of 3.9X10-6 atm-cu m/mole. 2,3,6-Trimethylphenol is not expected to volatilize from dry soil surfaces based on its vapor pressure. Based on limited information, this compound does not appear to biodegrade under anaerobic conditions; biodegradability under aerobic conditions is unknown. If released into water, 2,3,6-trimethylphenol is expected to adsorb to suspended solids and sediment in the water column based upon the estimated Koc. Volatilization from water surfaces is expected based upon this compound's estimated Henry's Law constant. Estimated volatilization half-lives for a model river and model lake are 11 and 84 days, respectively. The potential for bioconcentration in aquatic organisms is moderate based on an estimated BCF value of 60. This compound is not expected to undergo hydrolysis in the environment due to the lack of hydrolyzable functional groups. Occupational exposure to 2,3,6-trimethylphenol may occur through inhalation and dermal contact with this compound at workplaces where 2,3,6-trimethylphenol is produced or used. (SRC)

Antidote and Emergency Treatment · 2 Einträge

Basic treatment: Establish a patent airway. Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if necessary. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with normal saline during transport ... . Administer activated charcoal ... . Dilution may be contraindicated because it may increase absorption. Do not use emetics ... . Cover skin burns with dry sterile dressings after decontamination ... . /Phenols and Related compounds/

Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in respiratory arrest. Positive-pressure ventilation techniques with a bag-valve-mask device may be beneficial. Monitor cardiac rhythm and treat arrhythmias if necessary ... . Start an IV with D5W TKO /SRP: "To keep open", minimal flow rate/. Use lactated Ringer's if signs of hypovolemia are present. Watch for signs of fluid overload. Consider drug therapy for pulmonary edema ... . For hypotension with signs of hypovolemia, administer fluid cautiously. Consider vasopressors for hypotension with a normal fluid volume. Watch for signs of fluid overload ... . Administer 1% solution methylene blue if patient is symptomatic with severe hypoxia, cyanosis, and cardiac compromise not responding to oxygen. ... . Treat seizures with diazepam (Valium) ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Phenols and Related Compounds/

Sicherheitsdaten

wgk
1
tsca
TSCA listed
ridadr
UN 2430 8/PG 3
hs_code
2907.19.2000
risk_code
37/38-41-36/37/38-34-43-38
hazard_code
C,Xi
safety_code
26-39-24/25-45-36/37/39-36/37
hazard_class
8
packing_group
III
Speicherklasse
11 - Combustible Solids
Giftige Stoffe Daten
2416-94-6(Hazardous Substances Data)
Hazard Classifications
Eye Dam. 1Skin Irrit. 2Skin Sens. 1

Vor- und nachgelagerte Produkte

Vorgelagerte Rohstoffe

Pentan-3-on4-Methylpentan-2-on2,5,6-Trimethylcyclohex-2-en-1-on1-(Trimethylsilyl)prop-1-in2,5-XylenolMethanol2,3-Xylenol2,5-Dimethylfuranm-KresolPropin