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3-(Methylamino)toluene
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Name

3-(Methylamino)toluene

 EINECS 211-795-0
CAS No. 696-44-6 Density 0.968 g/cm3
PSA 12.03000 LogP 2.10970
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;

Article Data 68

3-(Methylamino)toluene Synthetic route

67-56-1

methanol

108-44-1

1-amino-3-methylbenzene

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.
579-12-4

3-methyl-N-methylacetanilide

A

15258-50-1

N-ethyl-N-methyl-3-methylaniline

B

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%
50-00-0

formaldehyd

108-44-1

1-amino-3-methylbenzene

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%
67-56-1

methanol

99-08-1

1-methyl-3-nitrobenzene

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.
68-11-1

mercaptoacetic acid

211676-01-6

N-methyl-N-nosyl-m-toluidine

A

3406-75-5

2-(4-nitrophenylthio)acetic acid

B

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%
625-95-6

3-Iodotoluene

74-89-5

methylamine

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%
67-56-1

methanol

108-44-1

1-amino-3-methylbenzene

A

121-72-2

N,N-dimethyl-m-toluidine

B

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

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

A

1912-16-9

2-methyl-4,6-diphenyl-pyridine

B

623-08-5

N-methyl-p-toluidine

C

696-44-6

N-methyl-m-toluidine

D

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
616-38-6

carbonic acid dimethyl ester

108-44-1

1-amino-3-methylbenzene

A

121-72-2

N,N-dimethyl-m-toluidine

B

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%

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: C8H11N 
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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