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N-Methyl-4-anisidine
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Name

N-Methyl-4-anisidine

 EINECS 227-735-1
CAS No. 5961-59-1 Density 1.032 g/cm3
PSA 21.26000 LogP 1.80990
Solubility N/A Melting Point 33-36 °C(lit.)
Formula C8H11NO Boiling Point 252.4 °C at 760 mmHg
Molecular Weight 137.181 Flash Point 87.2 °C
Transport Information N/A Appearance white to greyish-brown crystal. low melting mass
Safety 22-24/25-36/37 Risk Codes 20/21/22
Molecular Structure Molecular Structure of 5961-59-1 (N-METHYL-P-ANISIDINE) Hazard Symbols
Synonyms

p-Anisidine,N-methyl- (7CI,8CI);4-(Methylamino)anisole;4-Methoxy-N-methylaniline;4-Methoxy-N-methylbenzenamine;N-(4-Methoxyphenyl)-N-methylamine;

Article Data 207

N-Methyl-4-anisidine Synthetic route

7451-55-0

ethyl 4-methoxyphenylcarbamate

5961-59-1

N-methyl-N-(4-methoxyphenyl)amine

Conditions
ConditionsYield
With lithium aluminium tetrahydride In tetrahydrofuran for 2h; Heating / reflux;100%
With lithium aluminium tetrahydride In tetrahydrofuran at 60℃;
With lithium aluminium tetrahydride In diethyl ether Inert atmosphere; Reflux;
50-00-0

formaldehyd

104-94-9

4-methoxy-aniline

5961-59-1

N-methyl-N-(4-methoxyphenyl)amine

Conditions
ConditionsYield
With butyl triphenylphosphonium tetraborate at 20℃; for 0.183333h;99%
With 3 weight% Pd/C; hydrogen In methanol at 80℃; under 3800.26 Torr; Reagent/catalyst; Autoclave;94.2%
Stage #1: formaldehyd; 4-methoxy-aniline With sodium methylate In methanol at 20℃; for 5h;
Stage #2: With sodium tetrahydroborate In methanol for 1.75h; Heating;		80%
67-56-1

methanol

104-94-9

4-methoxy-aniline

5961-59-1

N-methyl-N-(4-methoxyphenyl)amine

Conditions
ConditionsYield
With cesiumhydroxide monohydrate; (1,4-dimethyl-5,7-diphenyl-1,2,3,4-tetrahydro-6H-cyclopenta[b]pyrazin-6-one) irontricarbonyl complex3 at 110℃; Catalytic behavior; Reagent/catalyst; Temperature; Schlenk technique; Inert atmosphere;99%
With potassium tert-butylate; C49H50Cl2Ir2N5O(1+)*F6P(1-) at 130℃; for 4h;99%
With C12H16IrN4O2(1+)*BF4(1-); potassium hydroxide at 120℃; for 5h; Irradiation; Inert atmosphere; Sealed tube;95%
108874-78-8

N-(4-methoxyphenyl)-N-methyl-S-phenylthiohydroxylamine

A

882-33-7

diphenyldisulfane

B

5961-59-1

N-methyl-N-(4-methoxyphenyl)amine

Conditions
ConditionsYield
With boron trifluoride diethyl etherate In acetonitrile for 0.166667h; Mechanism; Product distribution; Ambient temperature; various solvents, Lewis acids, and N-methylbenzenesulfenanilide;A 97%
B 40%

4-cyano-N-(4-methoxyphenyl)-N-methylbenzenesulfonamide

5961-59-1

N-methyl-N-(4-methoxyphenyl)amine

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene; 1-dodecylthiol In water; N,N-dimethyl-formamide for 12h; Inert atmosphere;97%
5279-51-6

4-methoxy-N-methylformanilide

5961-59-1

N-methyl-N-(4-methoxyphenyl)amine

Conditions
ConditionsYield
With C18H37ClMoNO2P2; hydrogen; sodium triethylborohydride In tetrahydrofuran; toluene at 130℃; under 37503.8 Torr; for 24h; Autoclave; Glovebox;96%
With hydrogenchloride In water for 1.5h; Reflux;74%
With water Heating; Yield given;
With aluminum oxide; potassium fluoride for 0.333333h; microwave irradiation;

tert-butyl (4-methoxyphenyl)methylcarbamate

5961-59-1

N-methyl-N-(4-methoxyphenyl)amine

Conditions
ConditionsYield
With trifluoroacetic acid In dichloromethane at 25℃;96%
With trifluoroacetic acid In dichloromethane at 40℃; for 48h; Inert atmosphere; Schlenk technique;
With hydrogenchloride In water at 120℃;
35813-38-8

N-(4-methoxyphenyl)-N-methylacetamide

A

6114-15-4

4-methoxy-N-ethyl-N-methylaniline

B

5961-59-1

N-methyl-N-(4-methoxyphenyl)amine

Conditions
ConditionsYield
With triethyl borane; Triethoxysilane; sodium hydroxide In hexane at 80℃; for 6h; Reagent/catalyst; Solvent; Inert atmosphere; Sealed tube;A 3%
B 96%
With sodium triethylborohydride In tetrahydrofuran at 80℃; for 12h; Inert atmosphere; Schlenk technique; Glovebox; Sealed tube;A n/a
B 72%
With sodium triethylborohydride In tetrahydrofuran at 80℃; for 6h; Inert atmosphere; Schlenk technique; High pressure; Sealed tube;A n/a
B 72%
67-56-1

methanol

100-17-4

para-methoxynitrobenzene

5961-59-1

N-methyl-N-(4-methoxyphenyl)amine

Conditions
ConditionsYield
With potassium tert-butylate; C49H50Cl2Ir2N5O(1+)*F6P(1-) at 130℃; for 10h;96%
With [iridium(I)Br(carbonyl)2(κ1C-tBuImCH2PyCH2OMe)]; caesium carbonate at 129.84℃; for 5h; Catalytic behavior; Mechanism; Inert atmosphere; Glovebox; Green chemistry;92%
With rhodium(III) chloride hydrate; potassium tert-butylate at 130℃; for 48h; Sealed tube; High pressure;82%
35813-38-8

N-(4-methoxyphenyl)-N-methylacetamide

5961-59-1

N-methyl-N-(4-methoxyphenyl)amine

Conditions
ConditionsYield
Stage #1: N-(4-methoxyphenyl)-N-methylacetamide With sulfuric acid; water for 2h; Heating / reflux;
Stage #2: With sodium hydroxide; water Product distribution / selectivity;		95.86%
With potassium methanolate; C26H32MnN4O4 In butan-1-ol at 135℃; for 45h;63%
With hydrogenchloride In water; ethylene glycol for 24h; Reflux; Inert atmosphere;
With hydrogenchloride In water; ethylene glycol at 20℃; for 3h; Inert atmosphere;

N-Methyl-4-anisidine Chemical Properties

IUPAC Name: 4-methoxy-N-methylaniline
Synonyms of N-Methyl-4-anisidine (CAS NO.5961-59-1): 1-Methylamino-4-methoxybenzene ; 4-Methoxy-N-methylaniline ; 4-Methoxy-N-methylbenzenamine ; N-Methyl-p-anisidine ; p-Methoxy-N-methylaniline ; Benzenamine, 4-methoxy-N-methyl- (9CI) ; p-Anisidine, N-methyl- (8CI)
CAS NO: 5961-59-1
Molecular Formula: C8H11NO
Molecular Weight: 137.18
Molecular Structure:
EINECS: 227-735-1 
H bond acceptors: 2
H bond donors: 1
Freely Rotating Bonds: 2
Polar Surface Area: 12.47 Å2
Index of Refraction: 1.553
Molar Refractivity: 42.54 cm3
Molar Volume: 132.8 cm3
Surface Tension: 34.8 dyne/cm
Density: 1.032 g/cm3
Flash Point: 87.2 °C
Enthalpy of Vaporization: 48.98 kJ/mol
Boiling Point: 252.4 °C at 760 mmHg
Vapour Pressure: 0.0194 mmHg at 25°C 
Melting Point: 33-36 °C(lit.)
Appearance: white to greyish-brown crystal. low melting mass
SMILES: O(c1ccc(NC)cc1)C
InChI: InChI=1/C8H11NO/c1-9-7-3-5-8(10-2)6-4-7/h3-6,9H,1-2H3
InChIKey: JFXDIXYFXDOZIT-UHFFFAOYAN
Std. InChI: InChI=1S/C8H11NO/c1-9-7-3-5-8(10-2)6-4-7/h3-6,9H,1-2H3
Std. InChIKey: JFXDIXYFXDOZIT-UHFFFAOYSA-N
Product Categories of N-Methyl-4-anisidine (CAS NO.5961-59-1): Aromatics

N-Methyl-4-anisidine Safety Profile

Safety Information about N-Methyl-4-anisidine (CAS NO.5961-59-1):
Hazard Codes: HarmfulXn
Risk Statements: 20/21/22
R20/21/22: Harmful by inhalation, in contact with skin and if swallowed.
Safety Statements: 22-24/25-36/37
S22:Do not breathe dust. 
S24/25: Avoid contact with skin and eyes. 
S36/37: Wear suitable protective clothing and gloves.
WGK Germany: 3
F: 10

N-Methyl-4-anisidine Specification

General Information: As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear.
Extinguishing Media: Use water spray, dry chemical, carbon dioxide, or chemical foam. 
Handling: Avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and eyes.
Storage: Store in a cool, dry place. Store in a tightly closed container.

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