Product Name

  • Name

    3-(Methylamino)toluene

  • EINECS 211-795-0
  • CAS No. 696-44-6
  • Article Data68
  • CAS DataBase
  • Density 0.968 g/cm3
  • Solubility insoluble
  • Melting Point -10.08°C (estimate)
  • Formula C8H11N
  • Boiling Point 204.7 °C at 760 mmHg
  • Molecular Weight 121.182
  • Flash Point 77.3 °C
  • Transport Information UN 2810
  • Appearance clear yellow liquid
  • Safety 28-36/37-45-61-28A
  • Risk Codes 23/24/25-33-52/53
  • Molecular Structure Molecular Structure of 696-44-6 (3-(Methylamino)toluene)
  • Hazard Symbols ToxicT
  • Synonyms m-Toluidine,N-methyl- (6CI,7CI,8CI);N,3-Dimethylaniline;N,3-Dimethylbenzenamine;N-(3-Methylphenyl)methylamine;N-Methyl(3-methylphenyl)amine;N-Methyl-N-(3-methylphenyl)amine;N-Methyl-N-(m-tolyl)amine;N-Methyl-m-toluidine;NSC 9396;m,N-Dimethylaniline;
  • PSA 12.03000
  • LogP 2.10970

Synthetic route

methanol
67-56-1

methanol

1-amino-3-methylbenzene
108-44-1

1-amino-3-methylbenzene

N-methyl-m-toluidine
696-44-6

N-methyl-m-toluidine

Conditions
ConditionsYield
With C31H30ClIrN3O(1+)*F6P(1-); potassium tert-butylate at 130℃; for 12h;98%
With C19H37IrN4(2+)*2I(1-); potassium carbonate at 120℃; for 17h; Inert atmosphere; Schlenk technique; Sealed tube;90%
With triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone In dichloromethane at 20℃;
With hydrogen at 55℃; under 750.075 Torr; for 36h; Irradiation; Green chemistry;
With C19H24ClN2Ru; sodium hydroxide at 60℃; for 22h;99 %Chromat.
3-methyl-N-methylacetanilide
579-12-4

3-methyl-N-methylacetanilide

A

N-ethyl-N-methyl-3-methylaniline
15258-50-1

N-ethyl-N-methyl-3-methylaniline

B

N-methyl-m-toluidine
696-44-6

N-methyl-m-toluidine

Conditions
ConditionsYield
With triethyl borane; Triethoxysilane; sodium hydroxide In hexane at 80℃; for 6h; Reagent/catalyst; Solvent; Inert atmosphere; Sealed tube;A 2%
B 95%
Stage #1: 3-methyl-N-methylacetanilide With triethyl borane; 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane; potassium hydroxide In tetrahydrofuran at 100℃; for 24h; Inert atmosphere; Schlenk technique; Sealed tube;
Stage #2: With water; sodium hydroxide In tetrahydrofuran at 25℃; for 1h; Inert atmosphere; Schlenk technique; Sealed tube;
A 78%
B 11%
With sodium triethylborohydride In tetrahydrofuran at 80℃; for 6h; Inert atmosphere; Schlenk technique; High pressure; Sealed tube;A n/a
B 72%
formaldehyd
50-00-0

formaldehyd

1-amino-3-methylbenzene
108-44-1

1-amino-3-methylbenzene

N-methyl-m-toluidine
696-44-6

N-methyl-m-toluidine

Conditions
ConditionsYield
Stage #1: formaldehyd; 1-amino-3-methylbenzene With sodium methylate In methanol at 65℃; for 1h;
Stage #2: With sodium tetrahydroborate at 65℃; for 1.5h;
93%
With sodium tetrahydroborate; sodium methylate In methanol 1) room temp., 5 h, 2) reflux;89%
With methanol; sodium tetrahydroborate; sodium at 60℃; for 2h;82%
methanol
67-56-1

methanol

1-methyl-3-nitrobenzene
99-08-1

1-methyl-3-nitrobenzene

N-methyl-m-toluidine
696-44-6

N-methyl-m-toluidine

Conditions
ConditionsYield
With potassium tert-butylate at 130℃; for 24h; Sealed tube;93%
With [(N,N′-bis(diisopropylphosphino)-2,6-diaminopyridine)Mn(CO)3][Br]; potassium hydroxide at 110℃; for 16h; Molecular sieve; Sealed tube;80%
With [Ru(2-(6-methoxypyridin-2-yl)-1,10-phenanthroline)(MeCN)2Cl]Cl; sodium methylate at 110℃; for 12h; Green chemistry;87 %Chromat.
With platinum on carbon; potassium tert-butylate; hydrogen at 150℃; under 1500.15 Torr; for 24h; Autoclave;93 %Chromat.
mercaptoacetic acid
68-11-1

mercaptoacetic acid

N-methyl-N-nosyl-m-toluidine
211676-01-6

N-methyl-N-nosyl-m-toluidine

A

2-(4-nitrophenylthio)acetic acid
3406-75-5

2-(4-nitrophenylthio)acetic acid

B

N-methyl-m-toluidine
696-44-6

N-methyl-m-toluidine

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 20℃;A n/a
B 92%
3-Iodotoluene
625-95-6

3-Iodotoluene

methylamine
74-89-5

methylamine

N-methyl-m-toluidine
696-44-6

N-methyl-m-toluidine

Conditions
ConditionsYield
With copper(l) iodide; 6,7-dihydro-5H-quinolin-8-one oxime; potassium hydroxide In water at 25℃; for 24h; Inert atmosphere;90%
methanol
67-56-1

methanol

1-amino-3-methylbenzene
108-44-1

1-amino-3-methylbenzene

A

N,N-dimethyl-m-toluidine
121-72-2

N,N-dimethyl-m-toluidine

B

N-methyl-m-toluidine
696-44-6

N-methyl-m-toluidine

Conditions
ConditionsYield
With copper(I) oxide; hydrogenchloride; titanium(IV) oxide In water for 6h; UV-irradiation;A 83%
B 15%
With aluminum oxide at 350 - 400℃;
tert-butyl-methyl-3-tolylcarbamate

tert-butyl-methyl-3-tolylcarbamate

N-methyl-m-toluidine
696-44-6

N-methyl-m-toluidine

Conditions
ConditionsYield
With trifluoroacetic acid In dichloromethane at 25℃;83%
With trifluoroacetic acid In dichloromethane at 40℃; for 48h; Inert atmosphere; Schlenk technique;
With hydrogenchloride In water at 120℃;
1-methylamino-2-methyl-4,6-diphenylpyridinium tetrafluoroborate

1-methylamino-2-methyl-4,6-diphenylpyridinium tetrafluoroborate

A

2-methyl-4,6-diphenyl-pyridine
1912-16-9

2-methyl-4,6-diphenyl-pyridine

B

N-methyl-p-toluidine
623-08-5

N-methyl-p-toluidine

C

N-methyl-m-toluidine
696-44-6

N-methyl-m-toluidine

D

N,2-dimethylaniline
611-21-2

N,2-dimethylaniline

Conditions
ConditionsYield
In trifluoroacetic acid for 17h; Ambient temperature; Irradiation;A 81%
B n/a
C n/a
D n/a
carbonic acid dimethyl ester
616-38-6

carbonic acid dimethyl ester

1-amino-3-methylbenzene
108-44-1

1-amino-3-methylbenzene

A

N,N-dimethyl-m-toluidine
121-72-2

N,N-dimethyl-m-toluidine

B

N-methyl-m-toluidine
696-44-6

N-methyl-m-toluidine

Conditions
ConditionsYield
With 0.72KNaX-BS zeolite at 150℃; for 1h; Temperature;A 77%
B 22%
With NaY-BS zeolite at 150℃; for 1h;A 32%
B 43%
methanol
67-56-1

methanol

3-methylbenzoyl azide
71313-13-8

3-methylbenzoyl azide

N-methyl-m-toluidine
696-44-6

N-methyl-m-toluidine

Conditions
ConditionsYield
Stage #1: methanol; 3-methylbenzoyl azide at 70℃; for 3h; Inert atmosphere;
Stage #2: With C54H43ClN3P2Ru(1+)*F6P(1-); potassium carbonate at 140℃; Inert atmosphere;
77%
3-methyl-N-methylacetanilide
579-12-4

3-methyl-N-methylacetanilide

N-methyl-m-toluidine
696-44-6

N-methyl-m-toluidine

Conditions
ConditionsYield
With sodium triethylborohydride In tetrahydrofuran at 80℃; for 12h; Inert atmosphere; Schlenk technique; Glovebox; Sealed tube;72%
With hydrogenchloride In water; ethylene glycol at 20℃; for 3h; Inert atmosphere;
carbonic acid dimethyl ester
616-38-6

carbonic acid dimethyl ester

1-amino-3-methylbenzene
108-44-1

1-amino-3-methylbenzene

N-methyl-m-toluidine
696-44-6

N-methyl-m-toluidine

Conditions
ConditionsYield
With 0.94 HY-BS zeolite at 150℃; for 1h;67%
With binder-free FeHY-mmm zeolite In neat (no solvent) Sealed tube;
tert-butyl 1-allyl-2-methyl-2-(m-tolyl)hydrazinecarboxylate

tert-butyl 1-allyl-2-methyl-2-(m-tolyl)hydrazinecarboxylate

A

(E)-tert-butyl (3-(methyl(m-tolyl)amino)prop-1-en-1-yl)carbamate

(E)-tert-butyl (3-(methyl(m-tolyl)amino)prop-1-en-1-yl)carbamate

B

N-methyl-m-toluidine
696-44-6

N-methyl-m-toluidine

Conditions
ConditionsYield
With lithium diisopropyl amide In tetrahydrofuran; hexane at -78℃; for 3h; [1,2]-Wittig Rearrangement;A 62%
B 9%
N-methyl-N-phenylpropanamide
5827-78-1

N-methyl-N-phenylpropanamide

A

N-methyl-N-n-propylaniline
13395-54-5

N-methyl-N-n-propylaniline

B

N-methyl-m-toluidine
696-44-6

N-methyl-m-toluidine

Conditions
ConditionsYield
Stage #1: N-methyl-N-phenylpropanamide With triethyl borane; 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane; potassium hydroxide In tetrahydrofuran at 100℃; for 24h; Inert atmosphere; Schlenk technique; Sealed tube;
Stage #2: With water; sodium hydroxide In tetrahydrofuran at 25℃; for 1h; Inert atmosphere; Schlenk technique; Sealed tube;
A 61%
B 11%
methylamine
74-89-5

methylamine

N-methyl-m-toluidine
696-44-6

N-methyl-m-toluidine

Conditions
ConditionsYield
With copper In water at 100℃;52%
1-methoxy-2,6-dimethylpyridinium methyl sulfate
87117-15-5

1-methoxy-2,6-dimethylpyridinium methyl sulfate

A

2,6-dimethylpyridine
108-48-5

2,6-dimethylpyridine

B

N-methyl-m-toluidine
696-44-6

N-methyl-m-toluidine

Conditions
ConditionsYield
With Dimethylammonium sulphite In water at 150℃; for 24h;A 20%
B 42%
1-amino-3-methylbenzene
108-44-1

1-amino-3-methylbenzene

methyl iodide
74-88-4

methyl iodide

N-methyl-m-toluidine
696-44-6

N-methyl-m-toluidine

Conditions
ConditionsYield
man befreit das Produkt durch Ausfaellen seiner aether.Loesung mit Schwefelsaeure vom Toluidin, dampft die aether.Loesung ein, erhitzt den Rueckstand mit Eissigsaeureanhydrid und verseift das entstandene N-Methyl-;
Stage #1: 1-amino-3-methylbenzene 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;
1-amino-3-methylbenzene
108-44-1

1-amino-3-methylbenzene

methyl iodide
74-88-4

methyl iodide

A

N,N-dimethyl-m-toluidine
121-72-2

N,N-dimethyl-m-toluidine

B

N-methyl-m-toluidine
696-44-6

N-methyl-m-toluidine

1-amino-3-methylbenzene
108-44-1

1-amino-3-methylbenzene

trimethyl orthoformate
149-73-5

trimethyl orthoformate

N-methyl-m-toluidine
696-44-6

N-methyl-m-toluidine

Conditions
ConditionsYield
With sulfuric acid unter Entfernen des entstehenden Methanols auf 180grad und Erhitzen des danach isolierten Reaktionsprodukts mit wss.Salzsaeure;
N-methyl-N-(3-methylphenyl)carboxamide
39970-42-8

N-methyl-N-(3-methylphenyl)carboxamide

N-methyl-m-toluidine
696-44-6

N-methyl-m-toluidine

Conditions
ConditionsYield
With water Heating; Yield given;
With hydrogenchloride In water at 100℃; for 2.5h;
N-methyl-N-(3-methylphenyl)carboxamide
39970-42-8

N-methyl-N-(3-methylphenyl)carboxamide

A

formate
71-47-6

formate

B

N-methyl-m-toluidine
696-44-6

N-methyl-m-toluidine

Conditions
ConditionsYield
With sodium hydroxide In water at 30℃; Rate constant; Mechanism; also aq. DMSO;
3-methyl-N-methylacetanilide
579-12-4

3-methyl-N-methylacetanilide

A

acetate
71-50-1

acetate

B

N-methyl-m-toluidine
696-44-6

N-methyl-m-toluidine

Conditions
ConditionsYield
With sodium hydroxide In water; dimethyl sulfoxide at 90℃; Rate constant; Mechanism;
(Dimethoxy-phenyl-methyl)-methyl-m-tolyl-amine
79431-18-8

(Dimethoxy-phenyl-methyl)-methyl-m-tolyl-amine

A

α,α-dimethoxybenzyl cation
38092-03-4, 102651-95-6

α,α-dimethoxybenzyl cation

B

N-methyl-m-toluidine
696-44-6

N-methyl-m-toluidine

Conditions
ConditionsYield
With water In 1,4-dioxane at 25℃; Rate constant;
1-amino-3-methylbenzene
108-44-1

1-amino-3-methylbenzene

Acetic formic anhydride
2258-42-6

Acetic formic anhydride

N-methyl-m-toluidine
696-44-6

N-methyl-m-toluidine

Conditions
ConditionsYield
With dimethylsulfide borane complex 1) THF, r.t., 2 h, 2) THF, reflux, 3 h; Multistep reaction;
1-amino-3-methylbenzene
108-44-1

1-amino-3-methylbenzene

N-methyl-m-toluidine
696-44-6

N-methyl-m-toluidine

Conditions
ConditionsYield
With dimethylsulfide borane complex 1.) THF, RT, 2h, 2.) THF, reflux, 3 h; Multistep reaction;
Multi-step reaction with 3 steps
1: benzene / Heating
2: anhydrous potassium carbonate, sodium hydroxide, tetrabutylammonium hydrogensulphate / benzene / 1 h / 5 - 10 °C / Heating
3: water / Heating
View Scheme
Multi-step reaction with 3 steps
1.1: tert-butyl alcohol / 24 h / 40 °C / Inert atmosphere; Schlenk technique
2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.33 h / 0 °C / Inert atmosphere; Schlenk technique
2.2: 20 °C / Inert atmosphere; Schlenk technique
3.1: trifluoroacetic acid / dichloromethane / 48 h / 40 °C / Inert atmosphere; Schlenk technique
View Scheme
3-Methylacetanilide
537-92-8

3-Methylacetanilide

dimethyl sulfate
77-78-1

dimethyl sulfate

N-methyl-m-toluidine
696-44-6

N-methyl-m-toluidine

Conditions
ConditionsYield
With sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride 1.) benzene, water, 30 min, 2.) 2 h.; Multistep reaction;
methanol
67-56-1

methanol

1-amino-3-methylbenzene
108-44-1

1-amino-3-methylbenzene

aluminium oxide

aluminium oxide

A

N,N-dimethyl-m-toluidine
121-72-2

N,N-dimethyl-m-toluidine

B

N-methyl-m-toluidine
696-44-6

N-methyl-m-toluidine

Conditions
ConditionsYield
at 350 - 400℃;
N-m-tolyl-glycine nitrile

N-m-tolyl-glycine nitrile

A

N-(2-aminoethyl)-3-methylaniline
14088-79-0

N-(2-aminoethyl)-3-methylaniline

B

N-methyl-m-toluidine
696-44-6

N-methyl-m-toluidine

Conditions
ConditionsYield
With lithium aluminium tetrahydride; diethyl ether
N-methyl-m-toluidine
696-44-6

N-methyl-m-toluidine

3-methyl-N-nitroso-N-methylaniline
17485-25-5

3-methyl-N-nitroso-N-methylaniline

Conditions
ConditionsYield
With sodium azide In water; acetonitrile at 20℃;100%
With nitromethane; oxygen; copper(II) bis(trifluoromethanesulfonate); 1,8-diazabicyclo[5.4.0]undec-7-ene at 90℃; for 20h; Sealed tube;63%
With hydrogenchloride; sodium nitrite at 0 - 5℃;2.5%
N-methyl-m-toluidine
696-44-6

N-methyl-m-toluidine

4-chlorobenzoyl chloride
586-75-4

4-chlorobenzoyl chloride

4-bromo-N-methyl-N-(m-tolyl)benzamide

4-bromo-N-methyl-N-(m-tolyl)benzamide

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃; Inert atmosphere;100%
With triethylamine In dichloromethane at 0 - 20℃;99%
N-methyl-m-toluidine
696-44-6

N-methyl-m-toluidine

(S)-2,5-dihydropyrrole-1,2-dicarboxylic acid 1-tert-butyl ester
51154-06-4

(S)-2,5-dihydropyrrole-1,2-dicarboxylic acid 1-tert-butyl ester

tert-butyl (2S)-2-[methyl(m-tolyl)carbamoyl]-2,5-dihydropyrrole-1-carboxylate

tert-butyl (2S)-2-[methyl(m-tolyl)carbamoyl]-2,5-dihydropyrrole-1-carboxylate

Conditions
ConditionsYield
With pyridine; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide In ethyl acetate at 0 - 20℃; for 4h;100%
N-methyl-m-toluidine
696-44-6

N-methyl-m-toluidine

1-amino-3-methylbenzene
108-44-1

1-amino-3-methylbenzene

Conditions
ConditionsYield
With dichloro(dimethylglyoxime)(dimethylglyoximato)cobalt(III); (4,4'-di-tert-butyl-2,2'-dipyridyl)-bis-(2-phenylpyridine(-1H))-iridium(III) hexafluorophosphate; triethylamine In acetonitrile at -78℃; for 24h; Reagent/catalyst; Sealed tube; Inert atmosphere; Irradiation;100%
N-methyl-m-toluidine
696-44-6

N-methyl-m-toluidine

N,N-dimethyl-formamide
68-12-2, 33513-42-7

N,N-dimethyl-formamide

N-methyl-N-(3-methylphenyl)carboxamide
39970-42-8

N-methyl-N-(3-methylphenyl)carboxamide

Conditions
ConditionsYield
With zinc(II) phthalocyanine; carbon dioxide; phenylsilane at 25℃; under 3750.38 Torr; for 6h; Autoclave; chemoselective reaction;99%
N-methyl-m-toluidine
696-44-6

N-methyl-m-toluidine

1-Bromo-2-bromomethyl-benzene
3433-80-5

1-Bromo-2-bromomethyl-benzene

N-(2-bromobenzyl)-N-methyl-m-tolylamine
436845-45-3

N-(2-bromobenzyl)-N-methyl-m-tolylamine

Conditions
ConditionsYield
With potassium carbonate In acetonitrile for 4h; Heating;98%
5-bromothiophene-2-carbonyl chloride
31555-60-9

5-bromothiophene-2-carbonyl chloride

N-methyl-m-toluidine
696-44-6

N-methyl-m-toluidine

5-bromo-N-methyl-N-(3-methylphenyl)thiophene-2-carboxamide
1252464-84-8

5-bromo-N-methyl-N-(3-methylphenyl)thiophene-2-carboxamide

Conditions
ConditionsYield
With triethylamine at 0℃; for 3h;97%
With triethylamine In dichloromethane at 0℃; for 0.5h; Inert atmosphere;
N-methyl-m-toluidine
696-44-6

N-methyl-m-toluidine

4-amino-o-xylene
95-64-7

4-amino-o-xylene

Conditions
ConditionsYield
With aluminum oxide; aluminium trichloride for 0.0666667h; microwave irradiation;96%
carbon dioxide
124-38-9

carbon dioxide

N-methyl-m-toluidine
696-44-6

N-methyl-m-toluidine

N,N-dimethyl-m-toluidine
121-72-2

N,N-dimethyl-m-toluidine

Conditions
ConditionsYield
With diphenylsilane; caesium carbonate In acetonitrile at 80℃; under 750.075 Torr; for 72h; Schlenk technique; Inert atmosphere;95%
With phenylsilane; triphenylphosphine In tetrahydrofuran at 120℃; under 3750.38 Torr; for 24h; Autoclave; Green chemistry;93%
With dimanganese decacarbonyl; phenylsilane; C29H33N2P In acetonitrile at 100℃; under 750.075 Torr; for 15h;88%
3-(benzyloxy)-6-bromo-2,4,5-trimethylpyridine
1444336-77-9

3-(benzyloxy)-6-bromo-2,4,5-trimethylpyridine

N-methyl-m-toluidine
696-44-6

N-methyl-m-toluidine

5-(benzyloxy)-N,3,4,6-tetramethyl-N-m-tolylpyridin-2-amine

5-(benzyloxy)-N,3,4,6-tetramethyl-N-m-tolylpyridin-2-amine

Conditions
ConditionsYield
With tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate In toluene for 3h; Reflux;95%
carbon dioxide
124-38-9

carbon dioxide

N-methyl-m-toluidine
696-44-6

N-methyl-m-toluidine

N-methyl-N-(3-methylphenyl)carboxamide
39970-42-8

N-methyl-N-(3-methylphenyl)carboxamide

Conditions
ConditionsYield
With 1,10-Phenanthroline; phenylsilane; zinc diacetate In acetonitrile at 25℃; under 3750.38 Torr; for 4h; Autoclave;95%
With 2K(1+)*VOF4(2-)=K2{VOF4}; HSiPh3 In acetonitrile at 20℃; under 750.075 Torr; for 10h; Sealed tube; Autoclave;95%
With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 30℃; under 760.051 Torr; for 72h; Schlenk technique;93%
N-methyl-m-toluidine
696-44-6

N-methyl-m-toluidine

trifluoroacetic acid
76-05-1

trifluoroacetic acid

N,3-dimethyl-N-(2,2,2-trifluoroethyl)aniline

N,3-dimethyl-N-(2,2,2-trifluoroethyl)aniline

Conditions
ConditionsYield
With potassium phosphate; 18-crown-6 ether; phenylsilane In tetrahydrofuran at 80℃; for 12h; Glovebox; Molecular sieve; Schlenk technique;95%
oct-1-ene
111-66-0

oct-1-ene

N-methyl-m-toluidine
696-44-6

N-methyl-m-toluidine

3-methyl-N-(2-methyloctyl)aniline
1227053-80-6

3-methyl-N-(2-methyloctyl)aniline

Conditions
ConditionsYield
Stage #1: N-methyl-m-toluidine With N,N'-bis(2,6-dicyclopentyl-4-methoxyphenyl)formamidine; tetrabenzyl titanium at 20℃; for 0.333333h; Glovebox; Inert atmosphere;
Stage #2: oct-1-ene at 155℃; for 0.116667h; Sealed tube;
94%
With bis(indenyl)dimethyl-titanium In toluene at 105℃; for 24h; Inert atmosphere; regioselective reaction;84%
N-methyl-m-toluidine
696-44-6

N-methyl-m-toluidine

C8H8(2)H3N

C8H8(2)H3N

Conditions
ConditionsYield
With water-d2; silver trifluoromethanesulfonate In chloroform-d1 at 90℃; for 18h; regioselective reaction;94%
styrene
292638-84-7

styrene

carbon monoxide
201230-82-2

carbon monoxide

N-methyl-m-toluidine
696-44-6

N-methyl-m-toluidine

(S)-N-methyl-2-phenyl-N-(m-tolyl)propanamide

(S)-N-methyl-2-phenyl-N-(m-tolyl)propanamide

Conditions
ConditionsYield
With C52H52NO5P; palladium(II) iodide In tetrahydrofuran at 20℃; under 38002.6 Torr; for 72h; Autoclave; enantioselective reaction;94%
cyanoacetic acid
372-09-8

cyanoacetic acid

N-methyl-m-toluidine
696-44-6

N-methyl-m-toluidine

2-cyano-N-methyl-N-(m-tolyl)acetamide

2-cyano-N-methyl-N-(m-tolyl)acetamide

Conditions
ConditionsYield
Stage #1: cyanoacetic acid With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 20℃; for 3h;
Stage #2: N-methyl-m-toluidine With triethylamine In dichloromethane at 0 - 20℃;
93%
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0℃; for 1h; Inert atmosphere; Schlenk technique;81%
Stage #1: cyanoacetic acid With oxalyl dichloride In dichloromethane; N,N-dimethyl-formamide at 0 - 20℃; for 3h;
Stage #2: N-methyl-m-toluidine With triethylamine In dichloromethane; N,N-dimethyl-formamide at 0℃;
styrene
292638-84-7

styrene

N-methyl-m-toluidine
696-44-6

N-methyl-m-toluidine

3-methyl-N-(2-phenylpropyl)aniline
1041517-59-2

3-methyl-N-(2-phenylpropyl)aniline

Conditions
ConditionsYield
With pentakis(dimethylamido)tantalum In hexane at 140℃; for 96h; Inert atmosphere; Sealed tube; regioselective reaction;93%
formaldehyd
50-00-0

formaldehyd

C12H12N2O

C12H12N2O

N-methyl-m-toluidine
696-44-6

N-methyl-m-toluidine

C21H23N3O

C21H23N3O

Conditions
ConditionsYield
With C38H38N4O2Rh(1+)*F6P(1-) In acetonitrile at 20℃; for 7h; Mannich Aminomethylation; enantioselective reaction;93%
9-hydroxycalabaxanthone
35349-68-9

9-hydroxycalabaxanthone

bis(trichloromethyl) carbonate
32315-10-9

bis(trichloromethyl) carbonate

N-methyl-m-toluidine
696-44-6

N-methyl-m-toluidine

C33H33NO7

C33H33NO7

Conditions
ConditionsYield
Stage #1: bis(trichloromethyl) carbonate; N-methyl-m-toluidine With triethylamine In dichloromethane at 20℃; for 4h; Cooling with ice;
Stage #2: 9-hydroxycalabaxanthone With dmap In dichloromethane at 20℃; Cooling with ice;
92%
N-methyl-m-toluidine
696-44-6

N-methyl-m-toluidine

(+/-)-methyl 4-phenylbut-3-yn-2-yl carbonate

(+/-)-methyl 4-phenylbut-3-yn-2-yl carbonate

(R)-N,3-dimethyl-N-(4-phenylbut-3-yn-2-yl)aniline

(R)-N,3-dimethyl-N-(4-phenylbut-3-yn-2-yl)aniline

Conditions
ConditionsYield
With bis(1,5-cyclooctadiene)nickel (0); (R)-segphos In tert-Amyl alcohol at 60℃; for 48h; Glovebox; enantioselective reaction;91%
4-trifluoromethylbenzoic acid
455-24-3

4-trifluoromethylbenzoic acid

N-methyl-m-toluidine
696-44-6

N-methyl-m-toluidine

N,3-dimethyl-N-(4-(trifluoromethyl)benzyl)aniline

N,3-dimethyl-N-(4-(trifluoromethyl)benzyl)aniline

Conditions
ConditionsYield
With potassium phosphate; 18-crown-6 ether; phenylsilane In tetrahydrofuran at 80℃; for 12h; Glovebox; Molecular sieve; Schlenk technique;90%
1-(4-methylbenzensulfonyl)-4-phenyl-1H-1,2,3-triazole
884866-01-7

1-(4-methylbenzensulfonyl)-4-phenyl-1H-1,2,3-triazole

N-methyl-m-toluidine
696-44-6

N-methyl-m-toluidine

N-methyl-2-phenyl-N-(m-tolyl)-N'-tosylacetimidamide

N-methyl-2-phenyl-N-(m-tolyl)-N'-tosylacetimidamide

Conditions
ConditionsYield
In toluene at 120℃; for 12h; Inert atmosphere;89%
Ethyl bromodifluoroacetate
667-27-6

Ethyl bromodifluoroacetate

N-methyl-m-toluidine
696-44-6

N-methyl-m-toluidine

N-methyl-N-(3-methylphenyl)carboxamide
39970-42-8

N-methyl-N-(3-methylphenyl)carboxamide

Conditions
ConditionsYield
With water In N,N-dimethyl-formamide at 110℃; for 6h; Schlenk technique;89%
With copper (I) acetate; caesium carbonate; XPhos In N,N-dimethyl-formamide at 110℃; for 12h;79%
With copper (I) acetate; caesium carbonate; XPhos In water; N,N-dimethyl-formamide at 110℃; for 12h; Schlenk technique;79%
5-phenyl-3H-furan-2-one
1955-39-1

5-phenyl-3H-furan-2-one

N-methyl-m-toluidine
696-44-6

N-methyl-m-toluidine

N-methyl-N-(3-methylphenyl)-4-oxo-4-phenylbutanamide
1056199-48-4

N-methyl-N-(3-methylphenyl)-4-oxo-4-phenylbutanamide

Conditions
ConditionsYield
for 3h; Heating;87%

3-(Methylamino)toluene Chemical Properties

Molecule structure of 3-(Methylamino)toluene (CAS NO.696-44-6):

IUPAC Name: N,3-Dimethylaniline 
Molecular Weight: 121.17964 g/mol
Molecular Formula: C8H11
Density: 0.968 g/cm3 
Boiling Point: 204.7 °C at 760 mmHg 
Flash Point: 77.3 °C
Index of Refraction: 1.563
Molar Refractivity: 40.68 cm3
Molar Volume: 125.1 cm3
Surface Tension: 34.7 dyne/cm 
Enthalpy of Vaporization: 44.1 kJ/mol
Vapour Pressure: 0.259 mmHg at 25 °C 
Water Solubility: insoluble
XLogP3: 2.6
H-Bond Donor: 1
H-Bond Acceptor: 1
Rotatable Bond Count: 1
Exact Mass: 121.089149
MonoIsotopic Mass: 121.089149
Topological Polar Surface Area: 12
Heavy Atom Count: 9
Canonical SMILES: CC1=CC(=CC=C1)NC
InChI: InChI=1S/C8H11N/c1-7-4-3-5-8(6-7)9-2/h3-6,9H,1-2H3
InChIKey: FBGJJTQNZVNEQU-UHFFFAOYSA-N
EINECS: 211-795-0

3-(Methylamino)toluene Uses

 3-(Methylamino)toluene (CAS NO.696-44-6) is used as dye intermediates.

3-(Methylamino)toluene Safety Profile

Hazard Codes: ToxicT
Risk Statements: 23/24/25-33-52/53 
R23/24/25:Toxic by inhalation, in contact with skin and if swallowed. 
R33:Danger of cumulative effects. 
R52/53:Harmful to aquatic organisms, may cause long-term adverse effects in the aquatic environment.
Safety Statements: 28-36/37-45-61-28A 
S28:After contact with skin, wash immediately with plenty of soap-suds. 
S36/37:Wear suitable protective clothing and gloves. 
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) 
S61:Avoid release to the environment. Refer to special instructions / safety data sheets.
RIDADR: UN 2810 6.1/PG 3
WGK Germany: 3
HazardClass: 6.1(a)
PackingGroup: II

3-(Methylamino)toluene Specification

 3-(Methylamino)toluene (CAS NO.696-44-6) is also named as Aniline, N,m-dimethyl- ; N,3-Dimethylaniline ; N-3-Dimethylbenzenamine ; N-Methyl-3-methylaniline ; N-Methyl-m-toluidine ; NSC 9396 ; m,N-Dimethylaniline ; Benzenamine, N,3-dimethyl- . 3-(Methylamino)toluene (CAS NO.696-44-6) is clear yellow liquid.

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