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4,4'-メチレンビス(N-メチルアニリン)

4,4'-Methylenebis(N-methylaniline)

HCID 15735
ノート反応
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
部分構造検索類似構造を探す

基本情報

CAS
1807-55-2
標準SMILES
CNc1ccc(Cc2ccc(NC)cc2)cc1
InChIKey
ZMVMYBGDGJLCHV-UHFFFAOYSA-N
分子式
C15H18N2
平均分子量
226.32 g/mol
単同位体質量
226.14699858

概要

structure given in first source

名称と識別子

優先名称
4,4'-Methylenebis(N-methylaniline)
IUPAC
N-methyl-4-[[4-(methylamino)phenyl]methyl]aniline
現地名
4,4'-メチレンビス(N-メチルアニリン)
英語名
4,4'-METHYLENEBIS(N-METHYLANILINE)
分子式
C15H18N2
分子量
226.32

名称と別名

4,4'-Methylenebis(N-methylaniline)N,N-Dimethyl-4,4'-methylenedianilineBis(N-methylanilino)methan4,4'-Methylenebis(N-methylbenzenamine)Benzenamine, 4,4'-methylenebis(N-methyl-HSDB 2631Benzenamine, 4,4'-methylenebis[N-methyl-N,N'-dimethyl-p-methylenedianilineUNII-7AUF08SV1MBis(N-methylanilino)methan [German]EINECS 217-309-3BRN 2109030
名称をさらに表示
4,4'-メチレンビス(N-メチルアニリン)4,4'-ビスメチルアミノジアミノジフェニルメタン4,4′-メチレンビス(N-メチルアニリン)N-メチル-4-{[4-(メチルアミノ)フェニル]メチル}アニリン4,4′-ビスメチルアミノジアミノジフェニルメタンDIMETHYLDIAMINODIPHENYLMETHANEBIS-(N-METHYL-ANILINO-)METHANEmethyl-[4-[4-(methylamino)benzyl]phenyl]amineN-methyl-4-[[4-(methylamino)phenyl]methyl]aniline
N,N'-Dimethyl-4,4'-methylenedianilineN,N-DMALBis(Nmethylaniline)methane2-13-00-00111 (Beilstein Handbook Reference)4,4'-Methylenebis[N-methylbenzenamine]BIS(4-(METHYLAMINO)PHENYL)METHANEDTXSID7061986BIS(N-METHYLANILINO)METHAN (GERMAN)

物性

構造計算による物性

XLogP
3.6
極性表面積
24.1 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
17
形式電荷
0
複雑度
179

実験および物理化学的性質

Chemical ClassesNitrogen Compounds -> Other Aromatics (Nitrogen)
SolubilitySoluble in carbon tetrachloride, carbon disulfide.
DecompositionWhen heated to decomposition it emits toxic fumes of NOx.
Vapor Pressure1.76X10-5 mm Hg at 25 °C (et)

物理化学的性質

融点
55 · 55-56 °C
沸点
357.94 °C · 357.94°C (rough estimate)
比重(密度)
0.9543 · 0.9543 (rough estimate)
屈折率
1.5 · 1.5000 (estimate)
酸解離定数(Pka)
5.33 · 5.33±0.19(Predicted)
Henry's Law Constant
3.4 · 3.4×104 mol/(m3Pa) at 25℃, HSDB (2015)
EPAの化学物質情報
4 · Benzenamine, 4,4'-methylenebis[N-methyl- (1807-55-2)

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。

危険有害性情報

Regulatory InformationChemical: Benzenamine, 4,4'-methylenebis[N-methyl-
Hazards SummaryEmergency treatment: Methemoglobinemia; [HSDB] See 4,4'-Methylenedianiline.

安全と保護具

Disposal Methods · 1 件

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.

毒性情報

Environmental Fate · 3 件

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 1.0X10+4(SRC), determined from a structure estimation method(2), indicates that 4,4'-methylenebis(N-methylaniline) is expected to be immobile in soil(SRC). Volatilization of 4,4'-methylenebis(N-methylaniline) from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 2.9X10-10 atm-cu m/mole(SRC), using a fragment constant estimation method(3). 4,4'-Methylenebis(N-methylaniline) is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 1.8X10-5 mm Hg at 25 °C(SRC), determined from a fragment constant method(4). Biodegradation data were not available(SRC, 2009).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 1.0X10+4(SRC), determined from a structure estimation method(2), indicates that 4,4'-methylenebis(N-methylaniline) is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 2.9X10-10 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). According to a classification scheme(5), an estimated BCF of 66(SRC), from an estimated log Kow of 3.28(7) and a regression-derived equation(8), suggests the potential for bioconcentration in aquatic organisms is moderate(SRC). Biodegradation data were not available(SRC, 2009).

化学と産業

薬理情報

Metabolism/Metabolites · 1 件

... The major urinary metabolite of 4,4'-[14C]-methylenebis(N,N-dimethyl)benzamine (RMK), representing 36% of the total radioactivity recovered in the urine /of rats/, was N,N'-diacetyl-4,4'-(hydroxymethylene)dianiline. In vitro microsomal metabolism of RMK involved demethylation. Products included N,N-dimethyl-4,4'-methylenedianiline, N,N'-dimethyl-4,4'-methylenedianiline, N-methyl-4,4'-methylenedianiline, and 4,4'-methylenedianiline, representing 44.7, 5.3, 11.8, and 6.9%, respectively, of the total radioactivity recovered from the reaction mixture. ...

Absorption, Distribution and Excretion · 1 件

Studies on the in vivo and in vitro disposition of 4,4'-[14C]-methylenebis(N,N-dimethyl)benzamine (reduced Michler's ketone, RMK) were performed. Osborne-Mendel rats retained, after 24 hr, 78% of a /oral/ dose of [14C]RMK. At 24 hr after an i.p. dose, fat, liver, and intestine represented major sites for deposition of radioactivity. ...

用途と製造

Uses · 2 件

Used as a chemical intermediate; [HSDB]

CHEMICAL INTERMEDIATE /SRP: Not Produced in USA/

U.S. Exports · 2 件

(1972) No Data

(1975) No Data

U.S. Imports · 2 件

(1972) No Data

(1975) No Data

U.S. Production · 2 件

(1972) No Data (NO PRODN REPORTED SINCE 1964)

(1975) No Data

Methods of ManufacturingPROBABLY BY THE REACTION OF FORMALDEHYDE WITH ORTHO-TOLUIDINE
General Manufacturing InformationBenzenamine, 4,4'-methylenebis[N-methyl-: ACTIVE

サプライヤー

関連反応

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化合物ノート

読み込み中…

このページの内容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

データベース識別子

CAS
1807-55-2
PubChem CID
15735
DTXSID
DTXSID7061986
UNII
7AUF08SV1M
EC Number
217-309-3
Nikkaji
J33.846J

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 4,4'-methylenebis(N-methylaniline), which has an estimated vapor pressure of 1.8X10-5 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase 4,4'-methylenebis(N-methylaniline) 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 3.6 hours(SRC), calculated from its rate constant of 1.1X10-10 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase 4,4'-methylenebis(N-methylaniline) may be removed from the air by wet or dry deposition(SRC). 4,4'-Methylenebis(N-methylaniline) contains chromophores that absorb at wavelengths >290 nm(4) and therefore may be susceptible to direct photolysis by sunlight(SRC).

Adverse EffectsMethemoglobinemia - The presence of increased methemoglobin in the blood; the compound is classified as secondary toxic effect
Soil Adsorption/Mobility · 1 件

Using a structure estimation method based on molecular connectivity indices(1), the Koc of 4,4'-methylenebis(N-methylaniline) can be estimated to be 1.0X10+4(SRC). According to a classification scheme(2), this estimated Koc value suggests that 4,4'-methylenebis(N-methylaniline) is expected to be immobile in soil.

Artificial Pollution Sources4,4'-Methylenebis(N-methylaniline)'s former production and use as a chemical intermediate may have resulted in its release to the environment through various waste streams(SRC).
Environmental Bioconcentration · 1 件

An estimated BCF of 66 was calculated for 4,4'-methylenebis(N-methylaniline)(SRC), using an estimated log Kow of 3.28(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 4,4'-methylenebis(N-methylaniline) is estimated as 2.9X10-10 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that 4,4'-methylenebis(N-methylaniline) is expected to be essentially nonvolatile from water surfaces(2). 4,4'-Methylenebis(N-methylaniline) is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 1.8E-5 mm Hg(SRC), determined from a fragment constant method(3).

Non-Human Toxicity Excerpts · 1 件

/GENOTOXICITY/ Although none of the microsomal metabolites was a direct-acting mutagen in the standard Salmonella typhimurium assay, all could be activated to mutagens when incubated with 9000 X g liver supernatants and reduced nicotinamide adenine dinucleotide phosphate. The activation of 4,4'-methylenedianiline to a mutagen suggests that the methyl groups of /reduced Michler's ketone, RMK)/ are not required for the conversion of RMK to a reactive electrophile.

Environmental Abiotic Degradation · 1 件

The rate constant for the vapor-phase reaction of 4,4'-methylenebis(N-methylaniline) with photochemically-produced hydroxyl radicals has been estimated as 1.1X10-10 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 3.6 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). 4,4'-Methylenebis(N-methylaniline) is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(2). 4,4'-Methylenebis(N-methylaniline) contains chromophores that absorb at wavelengths >290 nm(2) and therefore may be susceptible to direct photolysis by sunlight(SRC).

Probable Routes of Human ExposureOccupational exposure to 4,4'-methylenebis(N-methylaniline) may occur through dermal contact with this compound at workplaces where 4,4'-methylenebis(N-methylaniline) is produced or used. (SRC)
Environmental Fate/Exposure Summary · 1 件

4,4'-Methylenebis(N-methylaniline)'s former production and use as a chemical intermediate may have resulted in its release to the environment through various waste streams. If released to air, an estimated vapor pressure of 1.8X10-5 mm Hg at 25 °C indicates 4,4'-methylenebis(N-methylaniline) will exist in both the vapor and particulate phases in the atmosphere. Vapor-phase 4,4'-methylenebis(N-methylaniline) 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 3.6 hours. Particulate-phase 4,4'-methylenebis(N-methylaniline) will be removed from the atmosphere by wet or dry deposition. 4,4'-Methylenebis(N-methylaniline)contains chromophores that absorb at wavelengths >290 nm and therefore may be susceptible to direct photolysis by sunlight. If released to soil, 4,4'-methylenebis(N-methylaniline) is expected to have no mobility based upon an estimated Koc of 1.0X10+4. Volatilization from moist soil surfaces is not expected to be an important fate process based uponan estimated Henry's Law constant of 2.9X10-10 atm-cu m/mole. 4,4'-Methylenebis(N-methylaniline) is not expected to volatilize from dry soil surfaces based upon its vapor pressure. Biodegradation data were not available. If released into water, 4,4'-methylenebis(N-methylaniline) is expected to adsorb to suspended solids and sediment based upon the estimated Koc. No data are available pertaining to biodegradation in aquatic environments. Volatilization from water surfaces is not expected to be an important fate process based upon this compound's estimated Henry's Law constant. An estimated BCF of 66 suggests the potential for bioconcentration in aquatic organisms is moderate. Hydrolysis is not expected to be an important environmental fate process since this compound lacks functional groups that hydrolyze under environmental conditions. Occupational exposure to 4,4'-methylenebis(N-methylaniline) may occur through dermal contact with this compound at workplaces where 4,4'-methylenebis(N-methylaniline) is produced or used. (SRC)

Antidote and Emergency Treatment · 3 件

/SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand-valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR as necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Aniline and related compounds/

/SRP:/ Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). 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 shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 ml/kg up to 200 ml of water for dilution if the patent can swallow, has a strong gag reflex, and does not drool. Administer activated charcoal ... . /Aniline and related compounds/

/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's (LR) if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Consider vasopressors if hypotensive 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. DIRECT PHYSICIAN ORDER ONLY ... . Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Aniline and related compounds/

安全データ

tsca
TSCA listed
有毒物質データの
1807-55-2(Hazardous Substances Data)
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