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100-61-8

Basic Information
CAS No.: 100-61-8
Name: Benzenamine, N-methyl-
Article Data: 864
Cas Database
Molecular Structure:
Molecular Structure of 100-61-8 (Benzenamine, N-methyl-)
Formula: C6H5NH(CH3)
Molecular Weight: 107.155
Synonyms: (Methylamino)benzene;AI3-19498;Aniline, N-methyl-;CCRIS 2870;HSDB 1654;Methylphenylamine;Monomethylaniline;
EINECS: 202-870-9
Density: 0.984 g/cm3
Melting Point: -57 °C(lit.)
Boiling Point: 196.249 °C at 760 mmHg
Flash Point: 78.889 °C
Solubility: 30 g/L
Appearance: pale yellow to brown liquid
Hazard Symbols: ToxicT,DangerousN
Risk Codes: 23/24/25-33-50/53
Safety: 28-36/37-45-60-61-28A
Transport Information: UN 2294 6.1/PG 3
PSA: 12.03000
LogP: 1.80130
Synthetic route
614-30-2

N-methyl-N-phenyl-benzenemethanamine

100-61-8

N-methylaniline

Conditions
ConditionsYield
With palladium 10% on activated carbon; hydrogen In methanol at 20℃; for 1.5h;100%
With hydrogenchloride; hydrogen; palladium on activated charcoal In methanol for 0.25h; Product distribution; Hydrogenolysis;91%
With sulfuric acid; nickel In methanol; water at 40℃; for 2h;84%
With triethylsilane; potassium tert-butylate at 130℃; for 18h; Sealed tube; Inert atmosphere;65%
With titanium(III) chloride; lithium In tetrahydrofuran for 22h; Heating;55%
86518-04-9

1-tert-butyl-N,1,1-trimethyl-N-phenylsilanamine

100-61-8

N-methylaniline

Conditions
ConditionsYield
With silica gel In ethanol; water at 20℃; for 2h;100%
591-50-4

iodobenzene

74-89-5

methylamine

100-61-8

N-methylaniline

Conditions
ConditionsYield
With copper In water at 100℃; for 12h; Ullmann reaction;99.8%
With copper(l) iodide; 6,7-dihydro-5H-quinolin-8-one oxime; potassium hydroxide In water at 25℃; for 24h; Inert atmosphere;95%
With potassium hydroxide In N,N-dimethyl-formamide at 110℃; for 24h; Buchwald-Hartwig Coupling;65%
With Cu2O nanoparticles (Cu2O-NPs) synthesized in n-Bu4POAc from CuCO3 In water at 75℃; for 16h; Concentration; Ionic liquid;65 %Spectr.
With copper In water at 100℃; for 24h; Sealed tube;
108-86-1

bromobenzene

74-89-5

methylamine

100-61-8

N-methylaniline

Conditions
ConditionsYield
With copper In water at 100℃; for 12h; Ullmann reaction;99.6%
With potassium hydroxide In N,N-dimethyl-formamide at 110℃; for 20h; Buchwald-Hartwig Coupling;52%
With tetrakis(triphenylphosphine) palladium(0); caesium carbonate; triphenylphosphine In o-xylene at 160℃; for 12h; Inert atmosphere;
67-56-1

methanol

62-53-3

aniline

100-61-8

N-methylaniline

Conditions
ConditionsYield
With C21H36BrMnNO2P2; potassium tert-butylate at 100℃; for 24h; Catalytic behavior; Reagent/catalyst; Time;99%
With cesiumhydroxide monohydrate; (1,4-dimethyl-5,7-diphenyl-1,2,3,4-tetrahydro-6H-cyclopenta[b]pyrazin-6-one) irontricarbonyl complex3 at 110℃; Schlenk technique; Inert atmosphere;99%
With C31H30ClIrN3O(1+)*F6P(1-); potassium tert-butylate at 130℃; for 12h; Catalytic behavior; Reagent/catalyst; Temperature;99%
1934-92-5

N-methyl-N-phenyl-benzamide

100-61-8

N-methylaniline

Conditions
ConditionsYield
With triethyl borane; Triethoxysilane; sodium hydroxide In hexane at 80℃; for 6h; Solvent; Reagent/catalyst; Inert atmosphere; Sealed tube;99%
With sodium triethylborohydride In tetrahydrofuran at 80℃; for 6h; Inert atmosphere; Schlenk technique; High pressure; Sealed tube;97%
Multi-step reaction with 3 steps
1: 48 percent / P2S5 / dioxane / 2 h / Ambient temperature
2: tetrahydrofuran / Ambient temperature
3: 44 percent Spectr. / NaBH4, ZnCl2 / methanol / 2 h
View Scheme
With C18H37ClMoNO2P2; hydrogen; sodium triethylborohydride In tetrahydrofuran; toluene at 100℃; under 37503.8 Torr; for 24h; Autoclave; Glovebox;28 %Chromat.
124-38-9

carbon dioxide

1145-27-3

N,N’-dimethyl-N,N’-diphenylmethanediamine

A

121-69-7

N,N-dimethyl-aniline

B

100-61-8

N-methylaniline

Conditions
ConditionsYield
With diphenylsilane; cesium formate In acetonitrile at 50℃; under 750.075 Torr; Green chemistry;A 99%
B n/a
55577-65-6

2,N-dimethyl-N-phenylpropanamide

100-61-8

N-methylaniline

Conditions
ConditionsYield
With triethyl borane; Triethoxysilane; sodium hydroxide In hexane at 80℃; for 6h; Solvent; Reagent/catalyst; Inert atmosphere; Sealed tube;99%
With sodium triethylborohydride In tetrahydrofuran at 80℃; for 6h; Inert atmosphere; Schlenk technique; High pressure; Sealed tube;88%
5827-78-1

N-methyl-N-phenylpropanamide

100-61-8

N-methylaniline

Conditions
ConditionsYield
With triethyl borane; Triethoxysilane; sodium hydroxide In hexane at 80℃; for 6h; Inert atmosphere; Sealed tube;99%
With sodium triethylborohydride In tetrahydrofuran at 80℃; for 6h; Inert atmosphere; Schlenk technique; High pressure; Sealed tube;94%
618-40-6

1-Methyl-1-phenylhydrazine

100-61-8

N-methylaniline

Conditions
ConditionsYield
With hydrogen; lithium 1-naphthalenide; nickel dichloride In tetrahydrofuran at 20℃; under 760.051 Torr; for 1h;98%
With titanium(III) chloride; water In tetrahydrofuran pH=7; Reflux; Alkaline aq. solution; Inert atmosphere;83%
With Wilkinson's catalyst In methanol at 25℃; for 24h;80%
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    MSDS/COA Download

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    Appearance Light yellow to brown oily liquid Color,Chroma --- Assay,GC 99%min Aniline 0.2% max N,N-Dimethyl aniline 0.7% max Water,KF 0.1% max Density 0.987-0.994 Appearance: Light yellow to brown oily liquid Port:Shanghai, Hangzhou

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Consensus Reports

Reported in EPA TSCA Inventory.

Standards and Recommendations

OSHA PEL: TWA 0.5 ppm (skin)
ACGIH TLV: TWA 0.5 ppm (skin)
DFG MAK: 0.5 ppm (2.2 mg/m3)
DOT Classification:  6.1; Label: KEEP AWAY FROM FOOD

Analytical Methods

For occupational chemical analysis use NIOSH: Monomethylamiline S153.

Specification

The N-Methylaniline is a toxic organic compound with the chemical formula C6H5NH(CH3). With the CAS registry number 100-61-8, it is also known as Anilinomethane. It belongs to the product categories of Intermediates of Dyes and Pigments; Anilines, Aromatic Amines and Nitro Compounds; Organics. Its EINECS registry number is 202-870-9. Its IUPAC name is called N-methylaniline. It is used as a latent and coupling solvent and is also used is as an intermediate for dyes, agrochemicals and other organic products manufacturing.

Physical properties of N-Methylaniline: (1)ACD/LogP: 1.71; (2)ACD/LogD (pH 5.5): 1.648; (3)ACD/LogD (pH 7.4): 1.711; (4)ACD/BCF (pH 5.5): 10.174; (5)ACD/BCF (pH 7.4): 11.757; (6)ACD/KOC (pH 5.5): 175.664; (7)ACD/KOC (pH 7.4): 203; (8)#H bond acceptors: 1; (9)#H bond donors: 1; (10)#Freely Rotating Bonds: 1; (11)Index of Refraction: 1.573; (12)Molar Refractivity: 35.862 cm3; (13)Molar Volume: 108.89 cm3; (14)Surface Tension: 35.699 dyne/cm; (15)Density: 0.984 g/cm3; (16)Flash Point: 78.889 °C; (17)Enthalpy of Vaporization: 43.245 kJ/mol; (18)Boiling Point: 196.249 °C at 760 mmHg; (19)Vapour Pressure: 0.402 mmHg at 25°C.

Preparation of N-Methylaniline: this chemical can be prepared by N,N-dimethyl-aniline. This reaction will need reagents potassium 12-tungstocobaltate(III), AcOK and solvents acetonitrile, H2O. The reaction time is 4 hours with reaction temperature of 20 °C.

N-Methylaniline can be prepared by N,N-dimethyl-aniline

Uses of N-Methylaniline: it can be used to produce N,N'-Dimethylsulfinyldianilin at temperature of -78 °C. This reaction will need reagents NEt3, SOCl2 and solvent diethyl ether with reaction time of 1 hour. The yield is about 35%.

N-Methylaniline can be prepared by N,N-dimethyl-aniline

When you are using this chemical, please be cautious about it as the following:
This chemical that at low levels can cause damage to health. It may present an immediate or delayed danger to one or more components of the environment. It is toxic by inhalation, in contact with skin and if swallowed. After contact with skin, you should wash immediately with plenty of ... (to be specified by the manufacturer). In case of accident or if you feel unwell seek medical advice immediately (show the label where possible).

You can still convert the following datas into molecular structure:
(1)Canonical SMILES: CNC1=CC=CC=C1
(2)InChI: InChI=1S/C7H9N/c1-8-7-5-3-2-4-6-7/h2-6,8H,1H3
(3)InChIKey: AFBPFSWMIHJQDM-UHFFFAOYSA-N

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
cat LDLo intravenous 24mg/kg (24mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

LUNGS, THORAX, OR RESPIRATION: DYSPNEA

LUNGS, THORAX, OR RESPIRATION: CYANOSIS
Journal of Industrial Hygiene and Toxicology. Vol. 31, Pg. 1, 1949.
guinea pig LDLo oral 1200mg/kg (1200mg/kg) PERIPHERAL NERVE AND SENSATION: FLACCID PARALYSIS WITHOUT ANESTHESIA (USUALLY NEUROMUSCULAR BLOCKAGE)

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION
U.S. Public Health Service, Public Health Bulletin. Vol. 271, Pg. 16, 1941.
guinea pig LDLo subcutaneous 1200mg/kg (1200mg/kg) PERIPHERAL NERVE AND SENSATION: FLACCID PARALYSIS WITHOUT ANESTHESIA (USUALLY NEUROMUSCULAR BLOCKAGE)

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION
U.S. Public Health Service, Public Health Bulletin. Vol. 271, Pg. 16, 1941.
rabbit LDLo intravenous 24mg/kg (24mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

LUNGS, THORAX, OR RESPIRATION: DYSPNEA

LUNGS, THORAX, OR RESPIRATION: CYANOSIS
Journal of Industrial Hygiene and Toxicology. Vol. 31, Pg. 1, 1949.
rabbit LDLo oral 280mg/kg (280mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

LUNGS, THORAX, OR RESPIRATION: DYSPNEA

LUNGS, THORAX, OR RESPIRATION: CYANOSIS
Journal of Industrial Hygiene and Toxicology. Vol. 31, Pg. 1, 1949.

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