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2,3,6-トリメチルフェノール

2,3,6-Trimethylphenol

HCID 17016
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基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
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基本情報

CAS
2416-94-6
標準SMILES
Cc1ccc(C)c(O)c1C
InChIKey
QQOMQLYQAXGHSU-UHFFFAOYSA-N
分子式
C9H12O
平均分子量
136.19 g/mol
単同位体質量
136.088815

概要

2,3,6-Trimethylphenol is a hydroxytoluene.

名称と識別子

優先名称
2,3,6-Trimethylphenol
IUPAC
2,3,6-trimethylphenol
現地名
2,3,6-トリメチルフェノール
英語名
2,3,6-Trimethylphenol
分子式
C9H12O
分子量
136.19

名称と別名

2,3,6-TRIMETHYLPHENOL2416-94-63-HydroxypseudocumenePhenol, 2,3,6-trimethyl-1-Hydroxy-2,3,6-trimethylbenzeneDTXSID6022187HSDB 5876UNII-05WKL2L5LJEINECS 219-330-305WKL2L5LJNSC 91509NSC-91509
名称をさらに表示
2,3,6-トリメチルフェノール3-ヒドロキシプソイドクメン2,3,6-トリメチルフェノ-ル2,3,6トリメチルフェノル3-ヒドロキシシュードクメン2,3,6‐トリメチルフェノール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

データベース識別子

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

物性

構造計算による物性補完中

XLogP
2.7
極性表面積
20.2 Ų
水素結合供与体数
1
水素結合受容体数
1
回転可能結合数
0
重原子数
10
形式電荷
0
複雑度
111

実験および物理化学的性質

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

log Kow = 2.67

2.67

2.67

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

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 件

226 °C

226.00 °C. @ 760.00 mm Hg

228 °C

Melting Point · 2 件

58 °C

63.5 - 64 °C

Vapor Pressure · 2 件

0.03 [mmHg]

安全と法規制

安全情報は参考情報です。供給元の安全データシート(SDS)、適用法令、専門家による評価に代わるものではありません。

GHS分類

GHS Classification · 6 件

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]

危険有害性情報

Regulatory Information · 4 件

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 件

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 件

Skin Corr. 1C (29.7%)

Acute toxicity (Oral) - Category 4

安全と保護具

Disposal Methods · 2 件

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.

化学と産業

薬理情報

Cellular LocationsMembrane

用途と製造

Uses · 2 件

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 件

(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 件

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

Flavoring Agents -> JECFA Flavorings Index

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

General Manufacturing Information · 3 件

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.

応用分野 · 3 件

用途有機合成原料。

用途ビタミンEの合成のための重要な原料、ポリフェニレンオキシド樹脂修飾のためのコモノマー

2,3,6-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.

関連反応

51 件
反応記録を作成
HRID 9684 の反応式
HRID 9684反応物としてuspto-grants-2006_08
HRID 48195 の反応式
HRID 48195反応物としてuspto-grants-2004_03
HRID 65800 の反応式
HRID 65800生成物としてuspto-grants-1978_12
HRID 65804 の反応式
HRID 65804生成物としてuspto-grants-1978_12
HRID 65809 の反応式
HRID 65809反応物としてuspto-grants-1978_12
HRID 85008 の反応式
HRID 85008反応物としてuspto-grants-2014_09
HRID 85009 の反応式
HRID 85009反応物としてuspto-grants-2014_09
HRID 85010 の反応式
HRID 85010反応物としてuspto-grants-2014_09
1 / 7 ページ

化合物ノート

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0.035 mm Hg at 25 °C

Physical Description · 3 件

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]

物理化学的性質

融点
59 · 59-62 °C(lit.)
沸点
215 °C · 215°C
比重(密度)
0.94 · 0.940
屈折率
1.5115 · 1.5115 (estimate)
FEMA
3963 · 3963 | 2,3,6-TRIMETHYLPHENOL
闪点
100 · 100
貯蔵温度
Inert atmosphere,Room Temperature
溶解性
0.1 g/mL、透明 · メタノール: 0.1 g/mL、透明
酸解離定数(Pka)
10.77 · 10.77±0.15(Predicted)
外見
powder to crystal
色
White to Orange to Green
臭い (Odor)
殺菌剤の臭い
水溶解度
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)
主な用途
フレーバーそして香料
化粧品成分の機能
香料
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 データベース
2416 · 2416-94-6(CAS DataBase Reference)
NISTの化学物質情報
2 · Phenol, 2,3,6-trimethyl-(2416-94-6)
EPAの化学物質情報
2 · 2,3,6-Trimethylphenol (2416-94-6)

化学的性質

化学的特性White or light yellow solid

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

Personal Protective Equipment (PPE) · 3 件

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/

毒性情報

Environmental Fate · 3 件

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 件

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 件

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 件

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 件

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 件

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 件

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 件

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 件

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/

安全データ

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
化審法
(3)-540, (4)-57, (9)-899
hazard_code
C,Xi
safety_code
26-39-24/25-45-36/37/39-36/37
hazard_class
8
packing_group
III
Hazard Classifications
Eye Dam. 1Skin Irrit. 2Skin Sens. 1
ストレージクラス
11 - Combustible Solids
有毒物質データの
2416-94-6(Hazardous Substances Data)
使用
調製方法 · 1 件

2,3,6-Trimethylphenol is produced selectively by gas phase methylation of m-cresol with methanol at 300–460 ℃ under normal pressure on ortho-selective metal oxide catalysts, as used for the selective methylation of phenol. The reaction occurs in multitube reactors with a fixed catalyst. The reaction temperature to be maintained depends on the catalyst used in each case. Iron oxide catalysts modified with oxides of other metals (e.g., Zn, Cr and Sn, or Mg and Si) are particularly suitable for the process.

上流・下流製品情報

上流原料

3-ペンタノン4-メチル-2-ペンタノン2,5,6-トリメチル-2-シクロヘキセン-1-オン1-(トリメチルシリル)-1-プロピン2,5-ジメチルフェノールメタノール2,3-ジメチルフェノール2,5-ジメチルフランm-クレゾール2-プロピン