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N-Methylaniline

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Name

N-Methylaniline

EINECS 202-870-9
CAS No. 100-61-8 Density 0.984 g/cm3
PSA 12.03000 LogP 1.80130
Solubility 30 g/L Melting Point -57 °C(lit.)
Formula C6H5NH(CH3) Boiling Point 196.249 °C at 760 mmHg
Molecular Weight 107.15 Flash Point 78.889 °C
Transport Information UN 2294 6.1/PG 3 Appearance pale yellow to brown liquid
Safety 28-36/37-45-60-61-28A Risk Codes 23/24/25-33-50/53
Molecular Structure Molecular Structure of 100-61-8 (Benzenamine, N-methyl-) Hazard Symbols ToxicT,DangerousN
Synonyms

(Methylamino)benzene;AI3-19498;Aniline, N-methyl-;CCRIS 2870;HSDB 1654;Methylphenylamine;Monomethylaniline;

 

N-Methylaniline 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%
93-61-8

N-methyl-N-phenylformamide

100-61-8

N-methylaniline

Conditions
ConditionsYield
With 1,3-Dimethoxybenzene; trichlorophosphate In dichloromethane at 40℃; for 24h; Product distribution; other carboxamides, var. solvents, var. temp., var. time, var. reagents mole ratio;97%
With C18H37ClMoNO2P2; hydrogen; sodium triethylborohydride In tetrahydrofuran; toluene at 100℃; under 37503.8 Torr; for 24h; Catalytic behavior; Reagent/catalyst; Solvent; Pressure; Temperature; Autoclave; Glovebox;94%
With aluminum oxide; potassium fluoride for 0.333333h; microwave irradiation;80%
5827-78-1

N-methyl-N-phenylpropanamide

A

13395-54-5

N-methyl-N-n-propylaniline

B

100-61-8

N-methylaniline

Conditions
ConditionsYield
With triethyl borane; sodium hydroxide In hexane at 80℃; for 6h; Inert atmosphere; Sealed tube;A 1%
B 97%
579-10-2

N-acetyl-N-methylaniline

100-61-8

N-methylaniline

Conditions
ConditionsYield
With 40% potassium fluoride/alumina at 85℃; for 0.0666667h; Microwave irradiation; Neat (no solvent);96%
With 9,10-dihydroanthracene; sodium triethylborohydride In tetrahydrofuran at 80℃; for 6h; Solvent; Reagent/catalyst; Inert atmosphere; Schlenk technique; High pressure; Sealed tube;86%
With [RuCl2(2-(diphenylphosphino)-N-((6-((diphenylphosphino)methyl)pyridin-2-yl)methyl)ethan-1-amine)]; potassium tert-butylate; hydrogen In tetrahydrofuran at 100℃; under 37503.8 Torr; for 20h; Catalytic behavior; Autoclave; chemoselective reaction;85%
108-90-7

chlorobenzene

74-89-5

methylamine

100-61-8

N-methylaniline

Conditions
ConditionsYield
With C38H49N2P*C9H10ClPd In 1,4-dioxane at 20℃; for 18h; Inert atmosphere; Schlenk technique;96%
With potassium hydroxide In N,N-dimethyl-formamide at 110℃; for 24h; Buchwald-Hartwig Coupling;45%
With water; copper(l) chloride at 220℃;
614-00-6

N-methyl-N-nitrosoaniline

100-61-8

N-methylaniline

Conditions
ConditionsYield
With triethylsilane; hydrogen iodide In dichloromethane at 20℃; for 0.25h; Reagent/catalyst;95%
With sodium tetrahydroborate; titanium tetrachloride In 1,2-dimethoxyethane for 14h; Ambient temperature;92%
With iron; acetic acid
28685-60-1

N-carbomethoxy-N-methylaniline

100-61-8

N-methylaniline

Conditions
ConditionsYield
With methyllithium; lithium bromide In tetrahydrofuran at 0℃; for 1h;95%
With sodium hydrogen telluride In N,N-dimethyl-formamide at 70 - 75℃; for 5h;82%
With Benzeneselenol; sodium hydride 1.) THF, 2.) HMPA, 10 h, reflux; Yield given. Multistep reaction;
109-73-9

N-butylamine

3-methyl-2-(N-methylanilino)benzothiazolium toluene-p-sulphonate

A

70038-63-0

butyl-(3-methyl-3H-benzothiazol-2-ylidene)-amine

B

100-61-8

N-methylaniline

Conditions
ConditionsYield
In dichloromethane at 25℃; for 3h;A 95%
B 88%
at 25℃; for 3h;A 95%
B 88%

Indazol-1-ylmethyl-phenyl-amine

100-61-8

N-methylaniline

Conditions
ConditionsYield
With lithium aluminium tetrahydride In diethyl ether at 25℃; for 5h; var. aminals deriv. of hydroxymethylindazole;95%
90-10-8

N-methylbenzenesulfonanilide

100-61-8

N-methylaniline

Conditions
ConditionsYield
With diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate; potassium tert-butylate In dimethyl sulfoxide at 20℃; for 17h; Reagent/catalyst; Inert atmosphere; Schlenk technique; Irradiation; Sealed tube;95%
With trimethylsilyl iodide In acetonitrile at 82℃; for 12h;91%
With chloro-trimethyl-silane; sodium iodide In acetonitrile for 3h; Heating;86%

C20H20N2O4

100-61-8

N-methylaniline

Conditions
ConditionsYield
With benzyltriethylammonium tetrathiomolybdate In acetonitrile at 28℃; for 0.5h;95%
50-00-0

formaldehyd

62-53-3

aniline

100-61-8

N-methylaniline

Conditions
ConditionsYield
With butyl triphenylphosphonium tetraborate at 20℃; for 0.25h;94%
With (CuAl)O(x); hydrogen In tetrahydrofuran at 120℃; under 3750.38 Torr; for 9h; Catalytic behavior; Reagent/catalyst; Solvent;89%
With hydrogen In 1,4-dioxane at 60℃; under 7500.75 Torr; for 24h; Autoclave;88%
2621-79-6

ethyl N-methyl-N-phenylcarbamate

100-61-8

N-methylaniline

Conditions
ConditionsYield
With methyllithium; lithium bromide In tetrahydrofuran at 0℃; for 1h;94%
121-69-7

N,N-dimethyl-aniline

A

50-00-0

formaldehyd

B

100-61-8

N-methylaniline

Conditions
ConditionsYield
With {Ru(IV)O(2,2`-bipyridine)(PPh3)}(ClO4)2 In acetonitrile at 21℃; Rate constant; Kinetics; Thermodynamic data; other Ru(IV) complex catalyst, ΔH(excit), ΔS(excit) determined;A n/a
B 94%
With dihydrogen peroxide; FePp In ethanol at 38℃; for 0.166667h; Product distribution; borate buffer, pH 9; further educts;
With phosphate buffer; dihydrogen peroxide; cytochrome c at 30℃; Equilibrium constant; Rate constant; also in the presence of phosphate bilayer;

N-methyl-N-tritylaniline

100-61-8

N-methylaniline

Conditions
ConditionsYield
Stage #1: N-methyl-N-tritylaniline With naphthalene; lithium In tetrahydrofuran at 0℃; for 1h;
Stage #2: With water In tetrahydrofuran at 0 - 20℃;
94%
618-40-6

1-Methyl-1-phenylhydrazine

135-19-3

β-naphthol

A

2834-92-6

1-amino-2-naphthol

B

100-61-8

N-methylaniline

Conditions
ConditionsYield
In ethylene glycol at 80℃; Solvent; Temperature; Inert atmosphere; regioselective reaction;A 88%
B 94%
at 80℃; for 4h;A 0.43 g
B 0.50 g

{Ru(IV)O(2,2`-bipyridine)(PPh3)}(ClO4)2

121-69-7

N,N-dimethyl-aniline

A

512844-06-3

{Ru(2,2'-bipyridine)2(NCMe)(PPPh3)}(2+)

B

100-61-8

N-methylaniline

Conditions
ConditionsYield
In acetonitrile Kinetics; byproducts: CH2O; stoicheiometric oxidation of N,N-dimethylaniline by the Ru complex in MeCN at 21°C; spectrophotometrical determination of the rate constant;A n/a
B 94%
103-84-4

Acetanilid

77-78-1

dimethyl sulfate

A

579-10-2

N-acetyl-N-methylaniline

B

100-61-8

N-methylaniline

Conditions
ConditionsYield
With hexamethylenetetramine hydrobromide; potassium carbonate In benzene at 8 - 10℃; for 0.75h;A 93%
B n/a
64999-94-6

N-methyl-N-phenyl-4-nitrobenzene sulphonamide

68-11-1

mercaptoacetic acid

A

3406-75-5

2-(4-nitrophenylthio)acetic acid

B

100-61-8

N-methylaniline

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 20℃;A n/a
B 93%
62-53-3

aniline

74-88-4

methyl iodide

100-61-8

N-methylaniline

Conditions
ConditionsYield
With C24H52B20Cl2Rh2Se2 In toluene at 20℃; for 1.66667h;93%
Stage #1: aniline With n-butyllithium In tetrahydrofuran; hexane at -40℃; for 0.25h; Inert atmosphere;
Stage #2: methyl iodide In tetrahydrofuran; hexane at -60 - 20℃; for 8h; Inert atmosphere;
With potassium carbonate In N,N-dimethyl-formamide at 55℃; for 24h; Sealed tube;
556-52-5

oxiranyl-methanol

100-61-8

N-methylaniline

42871-95-4

3-(methyl(phenyl)amino)propane-1,2-diol

Conditions
ConditionsYield
In methanol for 48h; Reflux;100%
In ethanol at 120℃; for 0.333333h; Microwave irradiation;81%
102-92-1

cinnamoyl chloride

100-61-8

N-methylaniline

27687-46-3

N-methyl-N-phenylcinnamamide

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃; Inert atmosphere;100%
In dichloromethane at 20℃; for 1h;97%
With triethylamine In ethyl acetate at 0 - 20℃;79%
622-78-6

Benzyl isothiocyanate

100-61-8

N-methylaniline

70741-04-7

N'-benzyl-N-methyl-N-phenyl-thiourea

Conditions
ConditionsYield
In ethanol at 25 - 30℃; for 1h;100%
With ethanol
103-72-0

phenyl isothiocyanate

100-61-8

N-methylaniline

4949-93-3

1-methyl-1,3-diphenyl-thiourea

Conditions
ConditionsYield
In ethanol at 25 - 30℃; for 1h;100%
Wavelength; Reagent/catalyst; Darkness;97%
In ethanol for 0.166667h; Heating;60%
4755-77-5

Ethyl oxalyl chloride

100-61-8

N-methylaniline

1457-86-9

ethyl-2-(methyl(phenyl)amino)-2-oxoacetate

Conditions
ConditionsYield
With triethylamine In dichloromethane for 0.5h; Ambient temperature;100%
With triethylamine In dichloromethane at 0 - 20℃;85%
With pyridine
With pyridine In dichloromethane for 5h; Ambient temperature;
107-13-1

acrylonitrile

100-61-8

N-methylaniline

94-34-8

N-(2-cyanoethyl)-N-methylaniline

Conditions
ConditionsYield
With 1,1,1,3',3',3'-hexafluoro-propanol at 20℃; under 10501100 Torr; for 17h; Michael Addition;100%
With Ps-AlCl3 at 70℃; for 3h; Michael Addition; chemoselective reaction;99%
With SBA-15-supported Co(II) complex at 20℃; for 3h; Michael condensation;82%
598-21-0

2-Bromoacetyl bromide

100-61-8

N-methylaniline

29182-97-6

N-methyl-2-bromoacetanilide

Conditions
ConditionsYield
With triethylamine In ethyl acetate at 0 - 25℃; for 0.5h;100%
In dichloromethane at 0 - 20℃; for 1h;98%
With triethylamine In dichloromethane at 20℃; for 16h;88%
2284-20-0

4-Methoxyphenyl isothiocyanate

100-61-8

N-methylaniline

N'-(4-methoxy-phenyl)-N-methyl-N-phenyl-thiourea

Conditions
ConditionsYield
In ethanol at 25 - 30℃; for 1h;100%
88-88-0

2,4,6-trinitrochlorobenzene

100-61-8

N-methylaniline

56042-31-0

N-methyl-2,4,6-trinitrodiphenylamine

Conditions
ConditionsYield
In acetonitrile at 25℃;100%
With ethanol
With ethanol; sodium acetate
109-69-3

n-Butyl chloride

100-61-8

N-methylaniline

3416-49-7

N-butyl-N-methylaniline

Conditions
ConditionsYield
With 3-(2-ethoxy-2-oxoethyl)-1-methyl-1H-imidazol-3-ium chloride at 90℃; for 3h; Inert atmosphere; Green chemistry;100%
100-61-8

N-methylaniline

614-69-7

2-tolyl isothiocyanate

N-methyl-N-phenyl-N'-o-tolyl-thiourea

Conditions
ConditionsYield
In ethanol at 25 - 30℃; for 1h;100%
100-61-8

N-methylaniline

1985-12-2

4-Bromophenyl isothiocyanate

107775-44-0

N-methyl-N-phenyl-N'-p-bromophenylthiourea

Conditions
ConditionsYield
In ethanol at 25 - 30℃; for 1h;100%
100-61-8

N-methylaniline

614-00-6

N-methyl-N-nitrosoaniline

Conditions
ConditionsYield
With oxygen; nitrogen(II) oxide In 1,2-dichloro-ethane for 24h; Product distribution; Mechanism; Ambient temperature; other amines, other solvents, var. time;100%
With oxygen; nitrogen(II) oxide In 1,2-dichloro-ethane for 24h; Ambient temperature;100%
With toluene-4-sulfonic acid; methoxybenzene; sodium nitrite In dichloromethane at 20℃; chemoselective reaction;100%
762-42-5

dimethyl acetylenedicarboxylate

100-61-8

N-methylaniline

125735-97-9

2-(methylphenylamino)but-2-enedioic acid dimethyl ester

Conditions
ConditionsYield
In water at 20℃; for 2h; Michael-type addition;100%
In water at 20℃;71%
In water at 0 - 20℃; for 2h;69%
In diethyl ether
100-52-7

benzaldehyde

100-61-8

N-methylaniline

614-30-2

N-methyl-N-phenyl-benzenemethanamine

Conditions
ConditionsYield
With sodium tris(acetoxy)borohydride In 1,2-dichloro-ethane at 18℃; for 4h; Solvent; Reagent/catalyst; Green chemistry;100%
With hydrogen In toluene at 140℃; under 22502.3 Torr; for 18h;98%
With sodium tetrahydroborate at 20℃; for 0.0333333h; Neat (no solvent); grinding;97%
10242-31-6

1-(4-nitrophenoxy)-2,4,6-trinitrobenzene

100-61-8

N-methylaniline

56042-31-0

N-methyl-2,4,6-trinitrodiphenylamine

Conditions
ConditionsYield
In [D3]acetonitrile at 25℃;100%
In benzene at 30℃;
In benzene at 30℃; Mechanism; Rate constant; various concentrations of N-methylaniline;
In acetonitrile at 25℃; Kinetics; Further Variations:; Solvents;
In [D3]acetonitrile at 25℃; Kinetics; Further Variations:; Solvents;
33842-02-3, 529510-96-1

dichloromethylenedimethyliminium chloride

100-61-8

N-methylaniline

341029-31-0

N,N,N'-Trimethyl-N'-phenyl-carbamidchlorid

Conditions
ConditionsYield
In dichloromethane100%

1,5-diethoxy-1,5-diphenylpenta-2,4-dienylium perchlorate

100-61-8

N-methylaniline

1,5-di(N-methyl-N-phenylamino)-1,5-diphenylpenta-2,4-dienylium perchlorate

Conditions
ConditionsYield
for 0.166667h;100%

1,3,4,6-tetrakis(isopropylthio)thieno<3,4-c>thiophenium bis(tetrafluoroborate)

100-61-8

N-methylaniline

N-<(isopropylthio)-<2,5-bis(isopropylthio)-4-isopropylthio(thiocarbonyl)-3-thienyl>methylene>-N-methyl-N-phenylammonium tetrafluoroborate

Conditions
ConditionsYield
In acetonitrile at -30℃; for 0.5h;100%
100-61-8

N-methylaniline

22696-39-5

N-hydroxy-N-methylaniline

Conditions
ConditionsYield
With 4-hydroperoxy-5-ethyl-3-methyllumiflavine In tert-butyl alcohol at 30℃; Rate constant;100%
With sodium perborate; Dihydrate sodium molybdate In acetic acid at 50℃; for 1h; Kinetics; Thermodynamic data; Catalytic behavior; Temperature;71%
With α-D-glucose 6-phosphate; oxygen; NADP; cyclohexanone monooxygenase at 25℃; for 24h; pH=8.6; Enzymatic reaction;
With air; cyclohexanone monooxygenase from Escherichia coli; NADPH In water at 25℃; pH=8.6; Enzyme kinetics;
With α-D-glucose 6-phosphate; cyclohexanone monooxygenase from Escherichia coli; NADP; glucose-6-phosphate dehydrogenase; air In water at 25℃; for 24h; pH=8.6;
22128-62-7

carbonochloridic acid, chloromethyl ester

100-61-8

N-methylaniline

186353-05-9

[N-methyl-N-phenyl]carbamic acid chloromethyl ester

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃;100%
With triethylamine In dichloromethane at 0 - 5℃; for 4h;73%
106-43-4

para-chlorotoluene

100-61-8

N-methylaniline

38158-65-5

N,4-dimethyl-N-phenylaniline

Conditions
ConditionsYield
With johnphos; sodium t-butanolate; palladium diacetate In toluene at 20℃; for 19h; Arylation;100%
With potassium tert-butylate; Pd(0) N-heterocyclic carbene-phosphine In 1,4-dioxane at 100℃;99%
With potassium hydroxide; bis(tri-tert-butylphosphine)palladium(0); cetyltrimethylammonim bromide In water; toluene at 90℃; for 19h;99%
100-61-8

N-methylaniline

287721-05-5

4-[phenyl(endo-8-methyl-8-azabicyclo[3.2.1]octan-3-yl)amino]benzoic acid

N-methyl-4-[(8-methyl-8-aza-bicyclo[3.2.1]oct-3-yl)-phenyl-amino]-N-phenyl-benzamide

Conditions
ConditionsYield
With N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate Acylation;100%
2845-89-8

1-chloro-3-methoxy-benzene

100-61-8

N-methylaniline

3-methoxy-N-methyl-N-phenyl-benzenamine

Conditions
ConditionsYield
With 2'-dicyclohexylphosphanyl-6-methoxy-biphenyl-3-sulfonic acid; palladium diacetate; sodium t-butanolate In diethylene glycol dimethyl ether at 120℃; for 72h; Buchwald-Hartwig Coupling; Inert atmosphere;100%
With sodium t-butanolate; palladium diacetate In toluene at 80℃; for 1h; Buchwald-Hartwig amination;97%
With potassium tert-butylate; C36H43Cl2N3OPd In toluene at 130℃; for 12h; Buchwald-Hartwig Coupling; Inert atmosphere; Schlenk technique;96%
100-61-8

N-methylaniline

5-bromo-10,20-diphenylporphyrinatonickel(II)

C39H27N5(2-)*Ni(2+)

Conditions
ConditionsYield
With 18-crown-6 ether; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate; palladium diacetate In tetrahydrofuran at 68℃; for 3h;100%
100-61-8

N-methylaniline

2937-50-0

Allyl chloroformate

allyl N-methyl-N-phenylcarbamate

Conditions
ConditionsYield
With sodium hydride In tetrahydrofuran at 20℃; for 1h;100%
With sodium hydrogencarbonate In tetrahydrofuran at 20℃; for 2h;94%
100-61-8

N-methylaniline

844821-65-4

(benzenemethylthio)difluoroethanoyl chloride

844821-66-5

2-(benzenemethylthio)-2,2-difluoroethanoyl (N-methyl)anilide

Conditions
ConditionsYield
In diethyl ether at -78 - 20℃;100%
865094-47-9

isopropenyl (5-tert-butyl-2-(p-tolyl)-2H-pyrazol-3-yl)carbamate

100-61-8

N-methylaniline

N-(5-tert-butyl-2-(p-tolyl)-2H-pyrazol-3-yl)-N'-methyl-N'-phenylurea

Conditions
ConditionsYield
With 1-Methylpyrrolidine In tetrahydrofuran at 23℃; for 22h;100%
13089-11-7

methyl 3,3,3-trifluoropyruvate

100-61-8

N-methylaniline

3,3,3-trifluoro-2-hydroxy-2-(4-methylamino-phenyl)-propionic acid methyl ester

Conditions
ConditionsYield
at 20℃; for 0.0833333h; Friedel-Crafts reaction;100%

N-Methylaniline Consensus Reports

Reported in EPA TSCA Inventory.

N-Methylaniline 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

N-Methylaniline Analytical Methods

For occupational chemical analysis use NIOSH: Monomethylamiline S153.

N-Methylaniline 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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