Product Name

  • Name

    m-Anisidine

  • EINECS 208-651-4
  • CAS No. 536-90-3
  • Article Data222
  • CAS DataBase
  • Density 1.064 g/cm3
  • Solubility <0.1 g/100 mL at 19 °C in water
  • Melting Point ?1-1 °C(lit.)
  • Formula C7H9NO
  • Boiling Point 251 °C at 760 mmHg
  • Molecular Weight 123.155
  • Flash Point 109.6 °C
  • Transport Information UN 2431 6.1/PG 3
  • Appearance Pale yellow oily liquid or dark red liquid
  • Safety 26-60-61-45-36/37-28B
  • Risk Codes 22-36/37/38-50/53-51/53-33-26/27/28
  • Molecular Structure Molecular Structure of 536-90-3 (m-Anisidine)
  • Hazard Symbols VeryT+, DangerousN, HarmfulXn
  • Synonyms 1-Amino-3-methoxybenzene;3-Aminoanisole;3-Methoxyaniline;3-Methoxybenzenamine;3-Methoxyphenylamine;NSC 7631;m-Aminoanisole;m-Aminomethoxybenzene;m-Anisylamine;m-Methoxyaniline;Benzenamine, 3-methoxy-;
  • PSA 35.25000
  • LogP 1.85860

Synthetic route

3-methoxyphenyl bromide
2398-37-0

3-methoxyphenyl bromide

m-Anisidine
536-90-3

m-Anisidine

Conditions
ConditionsYield
With bis(tri-ortho-tolylphosphine)palladium(0); (R)-(-)-1-[(S)-2-(dicyclohexylphosphino)ferrocenyl]ethyl-di-tert-butylphosphine; ammonia; sodium t-butanolate In 1,4-dioxane at 80℃; for 5h; Inert atmosphere;99%
With copper(l) iodide; 2-carboxyquinoline N-oxide; potassium carbonate; ammonium hydroxide In dimethyl sulfoxide at 80℃; for 23h; Inert atmosphere;93%
With ammonium hydroxide; copper(l) iodide; diethylenetriaminopentaacetic acid; potassium hydroxide In water at 100℃; for 12h; Sealed tube;90%
1-chloro-3-methoxy-benzene
2845-89-8

1-chloro-3-methoxy-benzene

m-Anisidine
536-90-3

m-Anisidine

Conditions
ConditionsYield
With bis(tri-ortho-tolylphosphine)palladium(0); (R)-(-)-1-[(S)-2-(dicyclohexylphosphino)ferrocenyl]ethyl-di-tert-butylphosphine; ammonia; sodium t-butanolate In 1,4-dioxane at 100℃; for 12h; Inert atmosphere;99%
With C43H63ClFeNiP2; ammonia; sodium t-butanolate In 1,4-dioxane; toluene at 100℃; for 16h; Reagent/catalyst; Inert atmosphere;91%
With ammonium sulfate; bis(1,5-cyclooctadiene)nickel (0); sodium t-butanolate at 100 - 110℃; for 12h;88%
With bis(1,5-cyclooctadiene)nickel (0); (R)-1-[(Sp)-2-(dicyclohexylphosphanyl)ferrocenyl]ethyldicyclohexylphosphane; ammonia; sodium t-butanolate In 1,4-dioxane; toluene at 110℃; for 16h; Sealed tube;
carbonic acid dimethyl ester
616-38-6

carbonic acid dimethyl ester

m-Hydroxyaniline
591-27-5

m-Hydroxyaniline

m-Anisidine
536-90-3

m-Anisidine

Conditions
ConditionsYield
With dimanganese decacarbonyl at 180℃; for 1h;99%
3-nitroanisole
555-03-3

3-nitroanisole

m-Anisidine
536-90-3

m-Anisidine

Conditions
ConditionsYield
With isopropyl alcohol; potassium hydroxide for 0.133333h; Microwave irradiation; regioselective reaction;98%
With hydrogen In ethanol; water at 25℃; under 11251.1 Torr; for 6h; chemoselective reaction;98%
With nickel(II) oxide; ethanol; potassium hydroxide for 0.183333h; Microwave irradiation; sealed vessel;97%
3-methoxyphenyl azide
3866-16-8

3-methoxyphenyl azide

m-Anisidine
536-90-3

m-Anisidine

Conditions
ConditionsYield
With ammonium hydroxide at 90℃; for 0.166667h;98%
With zinc In methanol at 20℃; for 6h;94%
With aluminium(III) iodide In benzene for 0.166667h; Reduction; Heating;93%
N'-(3-methoxy-phenyl)-N,N-dimethyl-formamidine

N'-(3-methoxy-phenyl)-N,N-dimethyl-formamidine

m-Anisidine
536-90-3

m-Anisidine

Conditions
ConditionsYield
With hydrogen; palladium dihydroxide In water; tert-butyl alcohol at 20℃; under 3361.46 Torr; for 12h; Hydrogenolysis;98%
tert-butyl 3-methoxyphenylcarbamate
60144-52-7

tert-butyl 3-methoxyphenylcarbamate

m-Anisidine
536-90-3

m-Anisidine

Conditions
ConditionsYield
In 2,2,2-trifluoroethanol at 150℃; for 1h; microwave irradiation;95%
With 2,2,2-trifluoroethanol at 150℃; for 1h; Product distribution / selectivity; Microwave irradiation;95%
With 2,2,2-trifluoroethanol at 150℃; for 1h; Product distribution / selectivity; Microwave irradiation;95%
With 1,1,1,3',3',3'-hexafluoro-propanol at 150℃; for 0.5h; Product distribution / selectivity; Microwave irradiation;89%
1,2-bis(3-methoxyphenyl)diazene
6319-23-9

1,2-bis(3-methoxyphenyl)diazene

m-Anisidine
536-90-3

m-Anisidine

Conditions
ConditionsYield
With formic acid; zinc In methanol at 20℃; for 0.116667h;94%
With hydrazine hydrate In ethanol Heating;94%
With hydrazine hydrate; aluminium In ethanol Heating;94%
3-methoxy-1-iodobenzene
766-85-8

3-methoxy-1-iodobenzene

m-Anisidine
536-90-3

m-Anisidine

Conditions
ConditionsYield
With potassium phosphate; copper(l) iodide; N-((1-oxy-pyridin-2-yl)methyl)oxalamic acid; ammonia In water; dimethyl sulfoxide at 25℃; Schlenk technique; Inert atmosphere; Sealed tube; chemoselective reaction;94%
Stage #1: 3-methoxy-1-iodobenzene With copper(l) iodide; D-glucosamine hydrochloride; potassium carbonate In water; acetone at 90℃; for 0.166667h;
Stage #2: With ammonia In water; acetone at 90℃; for 24h;
90%
With copper(l) iodide; 2-carboxyquinoline N-oxide; potassium carbonate; ammonium hydroxide In dimethyl sulfoxide at 50℃; for 23h; Inert atmosphere;90%
3-methoxy-N-methylaniline
14318-66-2

3-methoxy-N-methylaniline

m-Anisidine
536-90-3

m-Anisidine

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;94%
N'-(3-methoxy-phenyl)-N,N-dibenzyl-formamidine

N'-(3-methoxy-phenyl)-N,N-dibenzyl-formamidine

m-Anisidine
536-90-3

m-Anisidine

Conditions
ConditionsYield
With hydrogen; palladium dihydroxide In water; tert-butyl alcohol under 3620.04 Torr; Ambient temperature;90%
With hydrogen; palladium dihydroxide In water; tert-butyl alcohol at 20℃; under 2844.31 Torr; for 5h; Hydrogenolysis;90%
3-methoxyphenyl triflate
66107-33-3

3-methoxyphenyl triflate

m-Anisidine
536-90-3

m-Anisidine

Conditions
ConditionsYield
Stage #1: 3-methoxyphenyl triflate With bis(bis(trimethylsilyl)amido)zinc(II); tri-tert-butyl phosphine; tetrabutylammomium bromide; lithium chloride; bis(dibenzylideneacetone)-palladium(0) In tetrahydrofuran at 50℃; for 24h;
Stage #2: With hydrogenchloride In tetrahydrofuran; diethyl ether
90%
1-(m-methoxyphenyl)-4,5-dihydro-5-hydroxy-1H-1,2,3-triazole
108429-51-2

1-(m-methoxyphenyl)-4,5-dihydro-5-hydroxy-1H-1,2,3-triazole

A

3-Methoxy-formanilid
27153-17-9

3-Methoxy-formanilid

B

m-Anisidine
536-90-3

m-Anisidine

Conditions
ConditionsYield
With n-butyllithium In tetrahydrofuran for 1.5h; Ambient temperature;A 89%
B 10%
m-Hydroxyaniline
591-27-5

m-Hydroxyaniline

methyl iodide
74-88-4

methyl iodide

m-Anisidine
536-90-3

m-Anisidine

Conditions
ConditionsYield
With sodium hydride In tetrahydrofuran at 0 - 20℃;87%
3-methoxyphenylboronic acid
10365-98-7

3-methoxyphenylboronic acid

m-Anisidine
536-90-3

m-Anisidine

Conditions
ConditionsYield
With copper(I) oxide; ammonium hydroxide; air In methanol at 20℃; for 16h;87%
With sodium hydroxide; hydroxylamine-O-sulfonic acid In water; acetonitrile at 100℃; for 0.25h; Microwave irradiation;87%
With copper(ll) sulfate pentahydrate; ammonia; sodium hydroxide In water at 20℃; under 760.051 Torr; for 4h;84%
With copper(I) oxide; ammonium hydroxide; oxygen; sodium hydroxide In water at 25℃; for 15h;82%
With sodium hydroxide; hydroxylamine-O-sulfonic acid In acetonitrile at 20℃; for 16h;78%
2-(3-methoxyphenoxy)propanamide
60770-72-1

2-(3-methoxyphenoxy)propanamide

m-Anisidine
536-90-3

m-Anisidine

Conditions
ConditionsYield
With potassium hydroxide In dimethyl sulfoxide at 140℃; for 8h; Green chemistry;87%
2,4,6-tri(3-methoxyphenoxy)-1,3,5-triazine

2,4,6-tri(3-methoxyphenoxy)-1,3,5-triazine

m-Anisidine
536-90-3

m-Anisidine

Conditions
ConditionsYield
With ammonium sulfate; bis(1,5-cyclooctadiene)nickel (0); sodium t-butanolate at 100 - 110℃; for 12h;87%
benzyl (3-methoxyphenyl)carbamate
108716-30-9

benzyl (3-methoxyphenyl)carbamate

m-Anisidine
536-90-3

m-Anisidine

Conditions
ConditionsYield
With methylmagnesium bromide; hydrogen; palladium diacetate; nickel diacetate In water at 45℃; for 16h;85%
3-methoxyphenyl azide
3866-16-8

3-methoxyphenyl azide

tributylgermanium hydride
998-39-0

tributylgermanium hydride

A

3-methoxy-2-tributylgermylaniline

3-methoxy-2-tributylgermylaniline

B

5-methoxy-2-tributylgermylaniline

5-methoxy-2-tributylgermylaniline

C

m-Anisidine
536-90-3

m-Anisidine

Conditions
ConditionsYield
With thiophenol In toluene for 0.5h; Heating;A 2%
B 3%
C 83%
ammonium hydroxide
1336-21-6

ammonium hydroxide

3-methoxyphenyl bromide
2398-37-0

3-methoxyphenyl bromide

m-Anisidine
536-90-3

m-Anisidine

Conditions
ConditionsYield
With copper(ll) sulfate pentahydrate; potassium phosphate tribasic heptahydrate; water; Sucrose In water at 90℃; for 15h; Catalytic behavior; Green chemistry;82%
methanol
67-56-1

methanol

3-Iodoaniline
626-01-7

3-Iodoaniline

m-Anisidine
536-90-3

m-Anisidine

Conditions
ConditionsYield
With copper(l) iodide; 1,10-Phenanthroline; caesium carbonate at 110℃; for 21h;78%
1,10-Phenanthroline
66-71-7

1,10-Phenanthroline

3-Iodoaniline
626-01-7

3-Iodoaniline

m-Anisidine
536-90-3

m-Anisidine

Conditions
ConditionsYield
With CuI; caesium carbonate In methanol78%
1-(3-methoxyphenyl)-2,5-dimethyl-1 H-pyrrole
32570-19-7

1-(3-methoxyphenyl)-2,5-dimethyl-1 H-pyrrole

m-Anisidine
536-90-3

m-Anisidine

Conditions
ConditionsYield
With hydroxylamine hydrochloride; triethylamine In ethanol at 80℃; for 16h;76%
N-(3-methoxyphenyl)-2,4-dinitrobenzenesulfonamide

N-(3-methoxyphenyl)-2,4-dinitrobenzenesulfonamide

A

S-(2,4-Dinitrophenyl)-cystein
3165-76-2

S-(2,4-Dinitrophenyl)-cystein

B

sulfur dioxide
7446-09-5

sulfur dioxide

C

m-Anisidine
536-90-3

m-Anisidine

Conditions
ConditionsYield
In aq. phosphate buffer for 0.5h; pH=7.4;A n/a
B 76%
C n/a
potassium 3-methoxyphenyltrifluoroborate

potassium 3-methoxyphenyltrifluoroborate

m-Anisidine
536-90-3

m-Anisidine

Conditions
ConditionsYield
With sodium hydroxide; hydroxylamine-O-sulfonic acid In water; acetonitrile at 100℃; for 0.25h; Microwave irradiation;76%
O-methylresorcine
150-19-6

O-methylresorcine

m-Anisidine
536-90-3

m-Anisidine

Conditions
ConditionsYield
Stage #1: O-methylresorcine With Nonafluorobutanesulfonyl fluoride; tris(trimethylsilyl)amine; potassium hexamethylsilazane In tetrahydrofuran at 60℃; for 5h; Schlenk technique; Inert atmosphere;
Stage #2: With hydrogenchloride In water at 20℃; for 0.0833333h; pH=3 - 4;
75%
Multi-step reaction with 2 steps
1.1: 81 percent / K3PO4 / toluene; H2O / 0 - 20 °C
2.1: P(t-Bu)3; Zn[N(SiMe3)2]2; Bu4NBr / Pd(dba)2; LiCl / tetrahydrofuran / 24 h / 50 °C
2.2: 90 percent / aq. HCl / tetrahydrofuran; diethyl ether
View Scheme
2-methoxy-phenol
90-05-1

2-methoxy-phenol

m-Anisidine
536-90-3

m-Anisidine

Conditions
ConditionsYield
Stage #1: 2-methoxy-phenol With Nonafluorobutanesulfonyl fluoride; tris(trimethylsilyl)amine; potassium hexamethylsilazane In tetrahydrofuran at 60℃; for 5h; Schlenk technique; Inert atmosphere;
Stage #2: With hydrogenchloride In water at 20℃; for 0.0833333h; pH=3 - 4;
72%
1-(3-methoxyphenyl)urea
139-77-5

1-(3-methoxyphenyl)urea

benzoic acid
65-85-0

benzoic acid

A

1-benzoyl-3-(3-methoxyphenyl)urea
37528-30-6

1-benzoyl-3-(3-methoxyphenyl)urea

B

m-Anisidine
536-90-3

m-Anisidine

Conditions
ConditionsYield
With ethyl phosphate; ethyl polyphosphate (ppe) at 100 - 105℃; for 1.5h;A 71%
B 4%
(3-methoxyphenyl)hydrazine
15384-39-1

(3-methoxyphenyl)hydrazine

m-Anisidine
536-90-3

m-Anisidine

Conditions
ConditionsYield
With titanium tetrachloride; magnesium In tetrahydrofuran at 20℃; Inert atmosphere;71%
acetic anhydride
108-24-7

acetic anhydride

m-Anisidine
536-90-3

m-Anisidine

m-methoxyacetanilide
588-16-9

m-methoxyacetanilide

Conditions
ConditionsYield
With pyridine In dichloromethane at 0 - 20℃;100%
With cadmium(II) oxide at 80℃; for 0.0833333h; Neat (no solvent); Microwave irradiation;97%
With 2,3,4,5,7,8,9,10-octahydropyrimido[1,2-a]azepin-1-ium acetate In neat (no solvent) at 50℃; for 0.5h; Green chemistry;96%
m-Anisidine
536-90-3

m-Anisidine

p-toluenesulfonyl chloride
98-59-9

p-toluenesulfonyl chloride

N-tosyl-m-anisidine
58750-87-1

N-tosyl-m-anisidine

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran at 20℃; for 28h;100%
With triethylamine In dichloromethane at 4℃;100%
With triethylamine In tetrahydrofuran at 20℃; for 15h;95%
m-Anisidine
536-90-3

m-Anisidine

[1,4]naphthoquinone
130-15-4

[1,4]naphthoquinone

2-(3-methoxyphenylamino)naphthalene-1,4-dione
64505-63-1

2-(3-methoxyphenylamino)naphthalene-1,4-dione

Conditions
ConditionsYield
In ethanol at 20℃; Reagent/catalyst;100%
With copper(II) acetate monohydrate; acetic acid at 60 - 70℃; for 0.5h; Under air;93%
With potassium tert-butylate In N,N-dimethyl-formamide at 20℃; for 2h;76%
m-Anisidine
536-90-3

m-Anisidine

3-methoxyphenyl azide
3866-16-8

3-methoxyphenyl azide

Conditions
ConditionsYield
With tert.-butylnitrite; trimethylsilylazide In acetonitrile at 0 - 20℃; for 1h;100%
With tert.-butylnitrite; trimethylsilylazide In acetonitrile at 0 - 20℃; for 3h; Inert atmosphere;99%
Stage #1: m-Anisidine With sulfuric acid; sodium nitrite In water; acetic acid at 0 - 5℃; for 0.166667h;
Stage #2: With sodium azide In water; acetic acid at 0 - 5℃; for 3h;
94%
m-Anisidine
536-90-3

m-Anisidine

methanesulfonyl chloride
124-63-0

methanesulfonyl chloride

N-(3-methoxyphenyl)methanesulfonamide
7022-24-4

N-(3-methoxyphenyl)methanesulfonamide

Conditions
ConditionsYield
With pyridine In dichloromethane at 20℃; Cooling with ice;100%
With pyridine In dichloromethane Ambient temperature;89%
With pyridine In dichloromethane at 20℃; for 12h;52.6%
m-Anisidine
536-90-3

m-Anisidine

trifluoroacetic anhydride
407-25-0

trifluoroacetic anhydride

N-(3-methoxyphenyl)-2,2,2-trifluoroacetamide
14818-55-4

N-(3-methoxyphenyl)-2,2,2-trifluoroacetamide

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran at 0 - 20℃; for 0.75h;100%
In diethyl ether
With pyridine In dichloromethane at 0 - 20℃; Inert atmosphere;
With triethylamine
at 20℃; for 3h; Inert atmosphere;
furfural
98-01-1

furfural

m-Anisidine
536-90-3

m-Anisidine

N-(furan-2-ylmethylene)-3-methoxyaniline
95124-20-2

N-(furan-2-ylmethylene)-3-methoxyaniline

Conditions
ConditionsYield
In methanol at 20℃; for 24h;100%
for 2h; Yield given;
With magnesium sulfate In ethanol at 20℃;
pivaloyl chloride
3282-30-2

pivaloyl chloride

m-Anisidine
536-90-3

m-Anisidine

N-(3-methoxyphenyl)pivalamide
56619-93-3

N-(3-methoxyphenyl)pivalamide

Conditions
ConditionsYield
With pyridine; dmap In dichloromethane at 0℃; for 1h;100%
With sodium carbonate monohydrate In water; ethyl acetate at 0℃; for 1h; Inert atmosphere;99.5%
With sodium carbonate monohydrate In water; ethyl acetate at 0℃; for 1h; Inert atmosphere;99.5%
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

m-Anisidine
536-90-3

m-Anisidine

tert-butyl 3-methoxyphenylcarbamate
60144-52-7

tert-butyl 3-methoxyphenylcarbamate

Conditions
ConditionsYield
copper(II) bis(tetrafluoroborate) at 30 - 33℃; for 0.166667h;100%
In tetrahydrofuran at 20℃;100%
With zinc(II) perchlorate In tert-butyl alcohol at 20℃; for 10h;99%
m-Anisidine
536-90-3

m-Anisidine

benzaldehyde
100-52-7

benzaldehyde

N-benzylidene-m-anisidine
5877-59-8

N-benzylidene-m-anisidine

Conditions
ConditionsYield
In ethanol for 1h; Sonication;100%
In toluene for 0.5h; Heating;85%
In ethanol for 1h; Heating;
m-Anisidine
536-90-3

m-Anisidine

2-isothiocyanatobenzylpyridinium bromide
109768-45-8

2-isothiocyanatobenzylpyridinium bromide

1-{2-[3-(3-Methoxy-phenyl)-thioureido]-benzyl}-pyridinium; bromide
109768-50-5

1-{2-[3-(3-Methoxy-phenyl)-thioureido]-benzyl}-pyridinium; bromide

Conditions
ConditionsYield
In methanol for 5h;100%
m-Anisidine
536-90-3

m-Anisidine

diethyl 2-ethoxymethylenemalonate
87-13-8

diethyl 2-ethoxymethylenemalonate

Diethyl 2-<(3-methoxyphenylamino)methylene>malonate
56881-19-7

Diethyl 2-<(3-methoxyphenylamino)methylene>malonate

Conditions
ConditionsYield
at 90 - 110℃; for 1h;100%
at 125℃; for 3h;99%
In neat (no solvent) at 120℃; for 0.75h;98%
m-Anisidine
536-90-3

m-Anisidine

trifluoromethyl dihydro-1,4-dioxin-3-carbonyl chloride

trifluoromethyl dihydro-1,4-dioxin-3-carbonyl chloride

5,6-dihydro-N-(3-methoxy)phenyl-2-trifluoromethyl-1,4-dioxin-3-carboxamide

5,6-dihydro-N-(3-methoxy)phenyl-2-trifluoromethyl-1,4-dioxin-3-carboxamide

Conditions
ConditionsYield
Stage #1: trifluoromethyl dihydro-1,4-dioxin-3-carbonyl chloride With pyridine; polystyrene-bound 4-hydroxy-3-nitrobenzophenone In dichloromethane at 20℃; for 24h; Acylation;
Stage #2: m-Anisidine With triethylamine In acetonitrile for 2.5h; Acylation; Heating;
100%
bis(trichloromethyl) carbonate
32315-10-9

bis(trichloromethyl) carbonate

m-Anisidine
536-90-3

m-Anisidine

3-methoxyphenyl isocyanate
18908-07-1

3-methoxyphenyl isocyanate

Conditions
ConditionsYield
With triethylamine In dichloromethane100%
In dichloromethane at 20℃; for 1.5h;
In toluene at 100℃; Cooling with ice;
m-Anisidine
536-90-3

m-Anisidine

3-tert-butyl-4-chloro-1-methyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid amide
851520-56-4

3-tert-butyl-4-chloro-1-methyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid amide

3-tert-butyl-4-[(3-methoxyphenyl)amino]-1-methyl-1H-pyrazolo[3,4-b]pyridine-5-carboxamide

3-tert-butyl-4-[(3-methoxyphenyl)amino]-1-methyl-1H-pyrazolo[3,4-b]pyridine-5-carboxamide

Conditions
ConditionsYield
In 1,4-dioxane Heating;100%
m-Anisidine
536-90-3

m-Anisidine

4-chloro-1-cyclohexyl-3-methyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid amide
851520-97-3

4-chloro-1-cyclohexyl-3-methyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid amide

1-cyclohexyl-4-[(3-methoxyphenyl)amino]-3-methyl-1H-pyrazolo[3,4-b]pyridine-5-carboxamide

1-cyclohexyl-4-[(3-methoxyphenyl)amino]-3-methyl-1H-pyrazolo[3,4-b]pyridine-5-carboxamide

Conditions
ConditionsYield
In 1,4-dioxane Heating;100%
propyl cyanide
109-74-0

propyl cyanide

m-Anisidine
536-90-3

m-Anisidine

butyl-(3-methoxy-phenyl)amine
31084-55-6

butyl-(3-methoxy-phenyl)amine

Conditions
ConditionsYield
With ammonium formate; palladium on activated charcoal In methanol; water at 20℃; for 4.5h;100%
m-Anisidine
536-90-3

m-Anisidine

propiononitrile
107-12-0

propiononitrile

A

3‐methoxy‐N‐propylaniline
31084-54-5

3‐methoxy‐N‐propylaniline

B

2-methoxy-N,N-dipropylaniline
35666-61-6

2-methoxy-N,N-dipropylaniline

Conditions
ConditionsYield
With ammonium formate; palladium on activated charcoal In methanol; water at 20℃; for 3h;A 100%
B n/a
3-methoxyphenyl bromide
2398-37-0

3-methoxyphenyl bromide

m-Anisidine
536-90-3

m-Anisidine

3-methoxy-N-(3-methoxyphenyl)benzenamine
92248-06-1

3-methoxy-N-(3-methoxyphenyl)benzenamine

Conditions
ConditionsYield
With palladium diacetate; caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In toluene at 110℃; for 48h; Buchwald-Hartwig amination;100%
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium t-butanolate In toluene at 100℃; for 18h; Buchwald-Hartwig Coupling; Inert atmosphere;72%
With 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate; tris-(dibenzylideneacetone)dipalladium(0) In toluene at 120℃;40%
With palladium diacetate; caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In toluene for 72h; Reflux; Inert atmosphere;
1,3-dibromobenzene
108-36-1

1,3-dibromobenzene

m-Anisidine
536-90-3

m-Anisidine

N,N'-bis(3-methoxyphenyl)-1,3-benzenediamine
202127-21-7

N,N'-bis(3-methoxyphenyl)-1,3-benzenediamine

Conditions
ConditionsYield
With sodium t-butanolate; palladium diacetate; bis(diphenylphosphinyl)ferrocene In toluene at 100 - 110℃; for 12h;100%
With [(π-cinnamyl)Pd(tBuXPhos)]OTf In water at 45℃; for 36h;91%
para-bromotoluene
106-38-7

para-bromotoluene

m-Anisidine
536-90-3

m-Anisidine

3-methoxy-N-(4-methylphenyl)aniline
123017-90-3

3-methoxy-N-(4-methylphenyl)aniline

Conditions
ConditionsYield
With caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; palladium diacetate In toluene for 16h; Buchwald-Hartwig amination; Heating;100%
With caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; palladium diacetate In toluene100%
With palladium diacetate; caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In toluene for 16h; Buchwald-Hartwig Coupling; Reflux; Inert atmosphere;100%
5-methoxymethylene-2,2-dimethyl-1,3-dioxane-4,6-dione
15568-85-1

5-methoxymethylene-2,2-dimethyl-1,3-dioxane-4,6-dione

m-Anisidine
536-90-3

m-Anisidine

5-(((3-methoxyphenyl)amino)methylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione
213699-52-6

5-(((3-methoxyphenyl)amino)methylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione

Conditions
ConditionsYield
In acetonitrile at 20℃; for 0.25h;100%
In isopropyl alcohol Heating;96%
In isopropyl alcohol at 70℃; for 1h;44%
6-fluoronicotinic acid
403-45-2

6-fluoronicotinic acid

m-Anisidine
536-90-3

m-Anisidine

6-fluoro-N-(3-methoxy-phenyl)-nicotinamide
945400-81-7

6-fluoro-N-(3-methoxy-phenyl)-nicotinamide

Conditions
ConditionsYield
With dicyclohexyl-carbodiimide; dmap In dichloromethane at 0 - 20℃; for 1h;100%
4-Trifluoromethylphenylacetic acid
32857-62-8

4-Trifluoromethylphenylacetic acid

m-Anisidine
536-90-3

m-Anisidine

N-(3-methoxy-phenyl)-2-(4-trifluoromethyl-phenyl)-acetamide
1111734-31-6

N-(3-methoxy-phenyl)-2-(4-trifluoromethyl-phenyl)-acetamide

Conditions
ConditionsYield
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 20℃; for 1h;100%
4-chlorobenzaldehyde
104-88-1

4-chlorobenzaldehyde

m-Anisidine
536-90-3

m-Anisidine

4-chloro-N-(3-methoxybenzyl)aniline
940363-85-9

4-chloro-N-(3-methoxybenzyl)aniline

Conditions
ConditionsYield
With sodium tetrahydroborate; triethylamine In methanol100%
N-benzylaminomethyl resin

N-benzylaminomethyl resin

m-Anisidine
536-90-3

m-Anisidine

C15H16N3OPol

C15H16N3OPol

Conditions
ConditionsYield
Stage #1: m-Anisidine With boron trifluoride diethyl etherate; isopentyl nitrite In tetrahydrofuran at -20℃; for 2h;
Stage #2: N-benzylaminomethyl resin In tetrahydrofuran; pyridine; acetonitrile at 20℃; Cooling; solid phase reaction;
100%
Stage #1: m-Anisidine With boron trifluoride diethyl etherate; isopentyl nitrite In tetrahydrofuran at -20℃; for 2h;
Stage #2: N-benzylaminomethyl resin With pyridine In tetrahydrofuran at -20 - 20℃; solid phase reaction;
100%
Stage #1: m-Anisidine With boron trifluoride diethyl etherate; isopentyl nitrite In tetrahydrofuran at -20℃; for 2h;
Stage #2: N-benzylaminomethyl resin With pyridine In tetrahydrofuran; acetonitrile at -20 - 20℃;
m-Anisidine
536-90-3

m-Anisidine

4-methoxy-benzaldehyde
123-11-5

4-methoxy-benzaldehyde

(4-methoxybenzylidene)(3-methoxyphenyl)amine
99497-93-5

(4-methoxybenzylidene)(3-methoxyphenyl)amine

Conditions
ConditionsYield
With acetic acid In N,N-dimethyl-formamide for 1h;100%
With TiO2 nanotubes at 20℃; for 3h; Neat (no solvent); Sunlight;98%
In methanol for 12h; Reflux;
m-Anisidine
536-90-3

m-Anisidine

butyryl chloride
141-75-3

butyryl chloride

N-(3-methoxyphenyl)butanamide
132118-40-2

N-(3-methoxyphenyl)butanamide

Conditions
ConditionsYield
With pyridine In dichloromethane at 20℃; for 18h; Inert atmosphere;100%
With dmap; triethylamine In dichloromethane at 0 - 20℃; for 18h; Inert atmosphere;82%
In dichloromethane
Stage #1: m-Anisidine With triethylamine In tetrahydrofuran at 0℃; for 0.333333h;
Stage #2: butyryl chloride In tetrahydrofuran at 20℃; for 13h;
Stage #1: m-Anisidine With triethylamine In tetrahydrofuran at 25℃; for 0.166667h;
Stage #2: butyryl chloride In tetrahydrofuran at 25℃; for 3h; Sealed tube;
methyl 4-iodosalicylate
18179-39-0

methyl 4-iodosalicylate

m-Anisidine
536-90-3

m-Anisidine

methyl 2-hydroxy-4-(3-methoxyphenylamino)benzoate
1644060-64-9

methyl 2-hydroxy-4-(3-methoxyphenylamino)benzoate

Conditions
ConditionsYield
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; palladium diacetate; caesium carbonate In toluene at 100℃; for 15.25h; Buchwald-Hartwig Coupling; Inert atmosphere;100%
para-iodoanisole
696-62-8

para-iodoanisole

m-Anisidine
536-90-3

m-Anisidine

3-methoxy-N-(4-methoxyphenyl)benzenamine
3661-49-2

3-methoxy-N-(4-methoxyphenyl)benzenamine

Conditions
ConditionsYield
With tris-(dibenzylideneacetone)dipalladium(0); potassium tert-butylate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In toluene at 100℃; for 20h; Inert atmosphere;100%
Stage #1: para-iodoanisole With palladium diacetate; caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In toluene for 0.75h; Inert atmosphere;
Stage #2: m-Anisidine In toluene at 90℃; for 14h; Inert atmosphere;
81%
With tri-tert-butyl phosphine; palladium diacetate; sodium t-butanolate In toluene at 100℃; for 12h; Inert atmosphere;77.7%
With tri-tert-butyl phosphine; palladium diacetate; sodium t-butanolate In toluene at 100℃; for 23h; Inert atmosphere;

m-Anisidine Chemical Properties


IUPAC Name: 3-Methoxyaniline
Molecular Weight: 123.15246 [g/mol]
Molecular Formula: C7H9NO
XLogP3: 0.9
H-Bond Donor: 1
H-Bond Acceptor: 2 
EINECS: 208-651-4
Product Categories: Anilines, Aromatic Amines and Nitro Compounds; Aniline 
Water Solubility: <0.1 g/100 mL at 19 ºC 
Index of Refraction: 1.555
Molar Refractivity: 37.16 cm3
Molar Volume: 115.7 cm3
Surface Tension: 39.3 dyne/cm
Density: 1.064 g/cm3
Flash Point: 109.6 °C
Enthalpy of Vaporization: 48.83 kJ/mol
Boiling Point: 251 °C at 760 mmHg
Vapour Pressure: 0.021 mmHg at 25 °C
Appearance: Pale yellow oily liquid or dark red liquid.
Melting Point: -1-1 °C(lit.)
Classification Code of m-Anisidine (CAS NO.536-90-3): Mutation data 

m-Anisidine Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
bird - wild LD50 oral 562mg/kg (562mg/kg)   Archives of Environmental Contamination and Toxicology. Vol. 12, Pg. 355, 1983.
quail LD50 oral 562mg/kg (562mg/kg)   Archives of Environmental Contamination and Toxicology. Vol. 12, Pg. 355, 1983.
 

m-Anisidine Safety Profile

Hazard Codes: HarmfulXn,DangerousN,VeryT+
Risk Statements: 22-36/37/38-50/53-51/53-33-26/27/28 
R22:Harmful if swallowed. 
R36/37/38:Irritating to eyes, respiratory system and skin. 
R50/53:Very toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment. 
R51/53:Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment. 
R33:Danger of cumulative effects. 
R26/27/28:Very toxic by inhalation, in contact with skin and if swallowed.
Safety Statements: 26-60-61-45-36/37-28B 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S60:This material and its container must be disposed of as hazardous waste. 
S61:Avoid release to the environment. Refer to special instructions / safety data sheets. 
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) 
S36/37:Wear suitable protective clothing and gloves. 
S28:After contact with skin, wash immediately with plenty of soap-suds.
RIDADR: UN 2431 6.1/PG 3
WGK Germany: 1
RTECS: BZ5408000
HazardClass: 6.1
PackingGroup: III

m-Anisidine Specification

  m-Anisidine (CAS NO.536-90-3), its Synonyms are 1-Amino-3-methoxybenzene ; 3-Aminoanisole ; 3-Methoxyaniline ; 3-Methoxybenzenamine ; m-Anisylamine ; m-Aminoanisole ; 3-Anisidine ; m-Methoxyaniline ; Benzenamine, 3-methoxy- . It is very poisonous for the blood leading to pink coloration of the skin and inner suffocation. Additionally its vapors are irritanting to eyes, mucous membranes, the respiratory system and skin.

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