2,2'-メチレンビス(6-tert-ブチル-p-クレゾール)

2,2'-Methylenebis(4-methyl-6-tert-butylphenol)

HCID 8398CAS 119-47-1

基本情報

標準SMILES
Cc1cc(Cc2cc(C)cc(C(C)(C)C)c2O)c(O)c(C(C)(C)C)c1
InChIKey
KGRVJHAUYBGFFP-UHFFFAOYSA-N
分子式
C23H32O2
平均分子量
340.5 g/mol
単同位体質量
340.24023026

名称と識別子

優先名称
2,2'-Methylenebis(4-methyl-6-tert-butylphenol)
IUPAC
2-tert-butyl-6-[(3-tert-butyl-2-hydroxy-5-methylphenyl)methyl]-4-methylphenol
現地名
2,2'-メチレンビス(6-tert-ブチル-p-クレゾール)
英語名
2,2'-Methylenebis(4-methyl-6-tert-butylphenol)
分子式
C23H32O2
分子量
340.5

名称と別名

119-47-12,2'-Methylenebis(6-tert-butyl-p-cresol)Antioxidant 22462,2'-Methylenebis(4-methyl-6-tert-butylphenol)Antioxidant BKFAntioxidant 1Anti OxCyanox 2246Advastab 405Lederle 2246Chemanox 21Catolin 14
名称をさらに表示
2,2'-メチレンビス(6-tert-ブチル-p-クレゾール)スミライザーMDP-S抗酸化剤1ロウィノックス22M46抗Ox酸化防止剤1ヨシノックス2246R2,2'-メチレンビス[4-メチル-6-(tert-ブチル)フェノール]酸化防止剤OMB2,2'-メチレンビス[6-tert-ブチル-4-メチルフェノール]2,2'-メチレンビス(4-メチル-6-tert-ブチルフェノール)アギドール22,2'-メチレンビス[6-(1,1-ジメチルエチル)-4-メチルフェノール]抗酸化剤22462,2'-メチリデンビス(6-tert-ブチル-4-メチルフェノール)抗酸化剤BKF2,2'-メチレンビス(6-tert-ブチル-4-メチルフェノール)6,6'-メチレンビス[2-(tert-ブチル)-4-メチルフェノール]4,4'-ジメチル-6,6'-ジ(tert-ブチル)[2,2'-メチレンビス(フェノール)]アンチOx2246ao2246BKFMethylenebisbutylcresolMETHYLENE DI-t-BUTYLCRESOLao1Bisalkofen BPantioxRalox 46
Vulkanox bkfNocrac NS 6Plastanox 2246Bisaklofen BPSumilizer MDPAO 1 (Antioxidant)Synox 5ltAlterungsschutzmittel BKF

データベース識別子

CAS
119-47-1
PubChem CID
8398
DTXSID
DTXSID4020870
ChEMBL
CHEMBL460648
ChEBI
CHEBI:172336
UNII
KVM0X4X57B
EC Number
204-327-1
Nikkaji
J36.831H

物性

構造計算による物性

XLogP
7.2
極性表面積
40.5 Ų
水素結合供与体数
2
水素結合受容体数
2
回転可能結合数
4
重原子数
25

実験および物理化学的性質

LogPLog Kow = 6.25
Density1.07-1.10 kg/L
Color/FormOff-white powder
Solubility · 2 件

Soluble in oxygen and aromatic solvents.

Water solubility = 0.02 mg/l.

Melting Point118-128 °C
Physical Description · 2 件

Liquid; Dry Powder; Other Solid; Dry Powder

Off-white solid; [HSDB]

物理化学的性質

融点
123 · 123-127 °C(lit.)
沸点
187 ℃ · 187℃
比重(密度)
1.04 g/cm3 · 1.04g/cm3
蒸気圧
1 hPa · <1 hPa
屈折率
1.448 · 1.4480 (estimate)
闪点
195 °C · 195°C(383°F)

安全と法規制

GHS分類

GHS Classification · 6 件

Danger

H360F: May damage fertility [Danger Reproductive toxicity]

P203, P280, P318, P405, and P501 (click each P-code to see the statement)

This chemical does not meet GHS hazard criteria for 15.4% (153 of 995) of reports.

危険有害性情報

Regulatory Information · 6 件

Chemical: Phenol, 2,2′-methylenebis[6-(1,1-dimethylethyl)-4-methyl-

Hazard Traits - Reproductive Toxicity;Authoritative List - EC Annex VI CMRs - Cat. 1B;Report - if used as a fragrance or flavor ingredient

Phenol, 2,2'-methylenebis[6-(1,1-dimethylethyl)-4-methyl- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Phenol, 2,2'-methylenebis[6-(1,1-dimethylethyl)-4-methyl- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Status: Active Update: 10-10-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/13380

Substance: 6,6'-di-tert-butyl-2,2'-methylenedi-p-cresol;EC: 204-327-1;Date of inclusion: >17-Jan-2022;Reason for inclusion: Toxic for reproduction (Article 57c)

Methylene bis methyl butyl phenol: Does not have an individual approval but may be used under an appropriate group standard

Other Safety InformationIMAP assessments - Phenol, 2,2'-methylenebis[6-(1,1-dimethylethyl)-4-methyl-: Human health tier II assessment
Hazards Summary · 1 件

Chronic high dose oral studies with rodents caused functional changes in the nervous system and liver and morphological changes to testes; [HSDB] A moderate eye irritant, based on animal studies; Although acute oral LD50 is more than 5,000 mg/kg, male reproductive effects were observed in sperm and histopathological changes to testes in test groups of 42.3 mg/kg and higher (NOAEL male reproductive toxicity = 12.2 mg/kg/day); [eChemPortal: SIDSUNEP] An eye irritant; [MSDSonline]

Hazard Classes and Categories · 4 件

Repr. 1B (25.2%);Repr. 2 (46.2%);Aquatic Chronic 4 (47.4%)

Reproductive toxicity - category 1B

Reproductive toxicity - Category 1B;Specific target organ toxicity - Repeated exposure - Category 2 (reproductive organs (male));Hazardous to the aquatic environment (Long-term) - Category 4

Repr. 1B

安全と保護具

Disposal Methods · 1 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.

毒性情報

Body BurdenBis(2-hydroxy-3-tert-butyl-5-methylphenyl)methane has been qualitatively detected in two samples of human adipose tissue from a 45 and over age group in the Western Region(1).
Interactions · 1 件

WHEN ADDED TO THE DIET FOR 4 MONTHS BEFORE TOPICAL APPLICATION OF BENZO[A]PYRENE & THEN UNTIL DEVELOPMENT OF MALIGNANCY BY THE INDUCED PAPILLOMAS, EXTRACTS FROM POLYETHYENE OR POLYPROPYLENE PRODUCTS, CONTAINING LOW AMOUNTS OF BIS(2-HYDROXY-3-TERT-BUTYL-5- METHYLPHENYL)METHANE, HAD AN INHIBITORY EFFECT ON THE CARCINOGENIC PROCESS.

Environmental Fate · 3 件

TERRESTRIAL FATE: Based on a recommended classification scheme(1), an estimated Koc value of 59800(SRC), determined from an experimental log Kow(2) and a recommended regression-derived equation(3), indicates that bis(2-hydroxy-3-tert-butyl-5-methylphenyl)methane will have no mobility in soil(SRC). Volatilization of bis(2-hydroxy-3-tert-butyl-5-methylphenyl)methane may not be important from moist soil surfaces(SRC) given an estimated Henry's Law constant of 7.9X10-12 atm-cu m/mole(4,SRC), or from dry soil surfaces(SRC) based on an estimated vapor pressure of 2.5X10-9 mm Hg(5,SRC). Based on a MITI biodegradation test, bis(2-hydroxy-3-tert-butyl-5-methylphenyl)methane will not biodegrade in soil(2).

AQUATIC FATE: Based on a recommended classification scheme(1), an estimated Koc value of 59800(SRC), determined from an experimental log Kow(2) and a recommended regression-derived equation(3), indicates that bis(2-hydroxy-3-tert-butyl-5-methylphenyl)methane will adsorb to suspended solids and sediment(SRC) in the water. Bis(2-hydroxy-3-tert-butyl-5-methylphenyl)methane should not volatilize from water surfaces based on an estimated Henry's Law constant of 7.9X10-12 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). Experimental BCF values of 23-37 and 60-125 at 1 and 0.1 mg/L(2), suggest that bis(2-hydroxy-3-tert-butyl-5-methylphenyl)methane will bioconcentrate in aquatic organisms(SRC) according to a recommended classification scheme(5). Based on a MITI biodegradation test, bis(2-hydroxy-3-tert-butyl-5-methylphenyl)methane will not biodegrade in water(2).

ATMOSPHERIC FATE: According to a suggested classification scheme(1), an estimated vapor pressure of 2.5X10-9 mm Hg at 25 °C(2,SRC) indicates that bis(2-hydroxy-3-tert-butyl-5-methylphenyl)methane will exist in the particulate phase in the ambient atmosphere. Particulate-phase bis(2-hydroxy-3-tert-butyl-5-methylphenyl)methane may be physically removed from the air by wet and dry deposition(SRC).

Adverse Effects · 1 件

Occupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation.;Reproductive Toxin - A chemical that is toxic to the reproductive system, including defects in the progeny and injury to male or female reproductive function. Reproductive toxicity includes developmental effects. See Guidelines for Reproductive Toxicity Risk Assessment.

Soil Adsorption/Mobility · 1 件

The Koc of bis(2-hydroxy-3-tert-butyl-5-methylphenyl)methane is estimated as approximately 59800(SRC), using an experimental log Kow of 6.25(1) and a regression-derived equation(2,SRC). According to a recommended classification scheme(3), this estimated Koc value suggests that bis(2-hydroxy-3-tert-butyl-5-methylphenyl)methane will be immobile in soil and strongly adsorbed to suspended solids and sediment in water(SRC).

TSCA Test Submissions · 1 件

2,2'-Bis(6-t-butyl-p-cresyl)methane (CAS # 119-47-1) was evaluated for dermal sensitization in humans. The test substance (25% concentration) was applied to the back of 25 adult males for a course of five (5) 48-hour exposures with 1-day rest periods. The test substance was applied to the same site which had been previously irritated by treatment with 5% sodium lauryl sulfate for 1-day. Two weeks after the last exposure, a challenge patch test of .5 g (10% concentration) of test substance was applied at a naive site under an occlusive dressing. The test substance was not irritating or allergic.

法規制情報

Regulatory Information · 6 件

Chemical: Phenol, 2,2′-methylenebis[6-(1,1-dimethylethyl)-4-methyl-

Hazard Traits - Reproductive Toxicity;Authoritative List - EC Annex VI CMRs - Cat. 1B;Report - if used as a fragrance or flavor ingredient

Phenol, 2,2'-methylenebis[6-(1,1-dimethylethyl)-4-methyl- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Phenol, 2,2'-methylenebis[6-(1,1-dimethylethyl)-4-methyl- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Status: Active Update: 10-10-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/13380

Substance: 6,6'-di-tert-butyl-2,2'-methylenedi-p-cresol;EC: 204-327-1;Date of inclusion: >17-Jan-2022;Reason for inclusion: Toxic for reproduction (Article 57c)

Methylene bis methyl butyl phenol: Does not have an individual approval but may be used under an appropriate group standard

安全データ

wgk
1
tsca
TSCA listed
rtecs
PA3500000
毒性
LD50 orally in Rabbit: 4880 mg/kg LD50 dermal Rabbit > 2000 mg/kg
hs_code
29072900
risk_code
36-62-53

化学と産業

用途と製造

Uses · 5 件

Used as an antioxidant and stabilizer for polymers (ABS, polypropylene, polyacetal, rubber, latex, and adhesives); [HSDB]

Plastic Composites Manufacturing [Category: Industry]

Stabilizer used in styrenic and olefin polymers and polyoxymethylene homo and copolymers.

Antioxidant (ABS, polypropylene, polyacetal, rubber, latex, adhesives).

Plastics -> Typical concentration range in plastic materials -> 0.5%

U.S. Production2023: 1,000,000 - <2,500,000 lb;2022: 1,000,000 - <2,500,000 lb;2021: 1,000,000 - <2,500,000 lb;2020: 2,500,000 - <4,000,000 lb
Consumer UsesAntioxidant
Industry UsesNot Known or Reasonably Ascertainable;UV stabilizer;Processing aids not otherwise specified;Antioxidant
Methods of ManufacturingReacting 2-t-butyl-p-cresol with formaldehyde through a carbonyl condensation.
Formulations/PreparationsSolid form
応用分野 · 3 件

用途酸化防止剤。

使用LOWINOX® 22M46 stabilizer is a non-discoloring antioxidant based on a sterically hindered alkylated bis-phenol.

一般的な説明2,2′-Methylenebis(6-tert-butyl-4-methylphenol) is a phenolic antioxidant commonly used in increasing the oxidation stability in rubber and plastic industries.

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関連反応

28 件

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