HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
Huagongshe Open Program:[email protected]AI access: llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.7.8
  1. Home
  2. /Compound

4,4'-Methylenebis(N-methylaniline)

HCID 15735
NotesReactions
Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
Substructure searchFind similar structures

Basic information

CAS
1807-55-2
Standard SMILES
CNc1ccc(Cc2ccc(NC)cc2)cc1
InChIKey
ZMVMYBGDGJLCHV-UHFFFAOYSA-N
Molecular formula
C15H18N2
Average molar mass
226.32 g/mol
Monoisotopic mass
226.14699858

Overview

structure given in first source

Names & identifiers

Preferred name
4,4'-Methylenebis(N-methylaniline)
IUPAC
N-methyl-4-[[4-(methylamino)phenyl]methyl]aniline
English name
4,4'-METHYLENEBIS(N-METHYLANILINE)
Molecular formula
C15H18N2
Molecular weight
226.32

Names & synonyms

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
Show more names
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)

Database identifiers

CAS
1807-55-2

Properties

Computed structural properties

XLogP
3.6
Topological polar surface area
24.1 Ų
Hydrogen bond donors
2
Hydrogen bond acceptors
2
Rotatable bonds
4
Heavy atoms
17
Formal charge
0
Complexity
179

Experimental & physicochemical properties

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)

Physicochemical properties

Melting point
55 · 55-56 °C
Boiling point
357.94 °C · 357.94°C (rough estimate)
Density
0.9543 · 0.9543 (rough estimate)
refractive index
1.5 · 1.5000 (estimate)
pka
5.33 · 5.33±0.19(Predicted)
Henry's Law Constant
3.4 · 3.4×104 mol/(m3Pa) at 25℃, HSDB (2015)
FDA UNII
7 AUF08SV1M · 7AUF08SV1M
EPA Substance Registry System

Safety & regulation

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

Hazard information

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

Safety & protection

Disposal Methods · 1 item

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.

Toxicology

Environmental Fate · 3 items

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).

Chemistry & industry

Pharmacology

Metabolism/Metabolites · 1 item

... 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 item

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. ...

Uses & manufacturing

Uses · 2 items

Used as a chemical intermediate; [HSDB]

CHEMICAL INTERMEDIATE /SRP: Not Produced in USA/

U.S. Exports · 2 items

(1972) No Data

(1975) No Data

U.S. Imports · 2 items

(1972) No Data

(1975) No Data

U.S. Production · 2 items

(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

Related reactions

0 records
New reaction record

No reaction records under the current filter.

Compound notes

Loading…

On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
PubChem CID
15735
DTXSID
DTXSID7061986
UNII
7AUF08SV1M
EC Number
217-309-3
Nikkaji
J33.846J
4 · Benzenamine, 4,4'-methylenebis[N-methyl- (1807-55-2)
TSCA
TSCA listed
Hazardous Substances Data
1807 · 1807-55-2(Hazardous Substances Data)

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 item

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 item

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 item

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 item

/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 item

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 item

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 items

/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/

Safety data

tsca
TSCA listed
Hazardous Substances Data
1807-55-2(Hazardous Substances Data)

Suppliers4 total

武汉丰泰威远科技有限公司+86-27-8746-5837 +86-18627785180 · [email protected]
武汉丰泰威远科技有限公司027-87465837 19945049750 · [email protected]
陕西缔都医药化工有限公司029-029-81120477 17792793610 · [email protected]
Shaanxi Dideu New Materials Co. Ltd18192503167 · [email protected]