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536-90-3

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536-90-3 Usage

Chemical Properties

Light yellow oily liquid with have characteristic amine (fishy) odors. soluble in alcohol, ether, benzene and dilute acid, slightly soluble in water. Anisidine exists as ortho-, meta-, and paraisomers.

Uses

Different sources of media describe the Uses of 536-90-3 differently. You can refer to the following data:
1. m-Anisidine is a highly poisonous monosubstituted aniline used as corrosion inhibitorsfor aluminum, copper and other metals in acidic solutions.
2. The unusually large amount of dibromo product produced upon bromination of m-anisidine may be attributed to the two doubly activeated positions. The best enantioselectivity of 97 % ee was observed for the reaction of m-anisidine in organocatalytic asymmetric three-component cyclization of cinnamaldehydes and primary amines with 1, 3-Dicarbonyl Compounds. Evidence for the control of 2nd-harmonic generation activities from the x-ray crystal-structures of the complexes of l-tartaric acid with m-anisidine and p-toluidine was determined.

Application

m-Anisidine is used in:The synthesis of N-substituted-3-chloro-2-azetidinones, which are potential anthelmintic agents.Rhodium-catalyzed synthesis of indoles and copper-catalyzed synthesis of benzimidazoles.In the preparation of azocalix[4]arene dyes.

Preparation

m-Aminoanisole is synthesized by reduction of m-nitrophenol after methylation on the hydroxyl group.A mixture of 35 g. (0.23 mole) of m-nitroanisole (p. 213), 110 ml. of methanol, and 7.5 ml. of concentrated hydrochloric acid is stirred and heated to boiling. Forty-two grams (0.75 gram atom) of iron filings is added in small portions over a 1-hour period, and refluxing and stirring are continued for 5 additional hours. The mixture is made strongly alkaline with sodium hydroxide and steam-distilled, the methanol which first distils over being collected separately. The remainder of the distillate is extracted with ether; the ethereal solu-tion is dried over anhydrous sodium sulfate and distilled. m-Anisidine (23.2 g. or 80%) is collected at 125°/13 mm.Reference: J. Chem. Soc, 1934, 1420; J. Chem. Soc, 127, 494 (1925).

Synthesis Reference(s)

The Journal of Organic Chemistry, 22, p. 333, 1957 DOI: 10.1021/jo01354a610Tetrahedron Letters, 24, p. 4121, 1983 DOI: 10.1016/S0040-4039(00)88277-5

General Description

M-anisidine appears as pale yellow oily liquid or dark red liquid. (NTP, 1992)

Air & Water Reactions

m-Anisidine may be sensitive to prolonged exposure to air and light. Insoluble in water.

Reactivity Profile

m-Anisidine is incompatible with strong oxidizers. m-Anisidine is also incompatible with acids, acid chlorides, acid anhydrides and chloroformates.

Fire Hazard

m-Anisidine is probably combustible.

Safety Profile

Moderately toxic by ingestion.Mutation data reported. When heated to decomposition itemits toxic vapors of NOx.

Purification Methods

o-Isomer impurity can be removed by steam distillation. Another possible impurity is the precursor 3-nitroanisole which can be removed as for the preceding o-isomer and fractionating using an efficient column. It is a yellow liquid. [Gilman & Kyle J Am Chem Soc 74 3027 1952, Bryson J Am Chem Soc 82 4858 1960, Kadaba & Massie J Org Chem 22 333 1957, Beilstein 13 IV 953.]

Check Digit Verification of cas no

The CAS Registry Mumber 536-90-3 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,3 and 6 respectively; the second part has 2 digits, 9 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 536-90:
(5*5)+(4*3)+(3*6)+(2*9)+(1*0)=73
73 % 10 = 3
So 536-90-3 is a valid CAS Registry Number.
InChI:InChI=1/C8H11NO/c1-2-10-8-5-3-4-7(9)6-8/h3-6H,2,9H2,1H3

536-90-3 Well-known Company Product Price

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  • Alfa Aesar

  • (A10815)  m-Anisidine, 98%   

  • 536-90-3

  • 50g

  • 335.0CNY

  • Detail
  • Alfa Aesar

  • (A10815)  m-Anisidine, 98%   

  • 536-90-3

  • 250g

  • 913.0CNY

  • Detail
  • Alfa Aesar

  • (A10815)  m-Anisidine, 98%   

  • 536-90-3

  • 1000g

  • 2955.0CNY

  • Detail

536-90-3SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name 3-Methoxyaniline

1.2 Other means of identification

Product number -
Other names m-Anisidine

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:536-90-3 SDS

536-90-3Synthetic 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;

536-90-3Relevant articles and documents

Ullmann reaction of picryl bromide in the presence of ultrasound

Nelson,Adolph

, p. 293 - 305 (1991)

Ultrasonic irradiation was found to promote the Ullman coupling of picryl bromide at or below room temperature. In the presence of excess copper, a long-lived intermediate is formed that is quenched upon work-up affording variable mixtures of trinitrobenzene and picric acid.

THE PLATINUM CATALYZED REDUCTION OF NITROARENES TO AMINOARENES WITH CARBON MONOXIDE AND WATER

Watanabe, Yoshihisa,Tsuji, Yasushi,Ohsumi, Tatsuya,Takeuchi, Ryo

, p. 4121 - 4122 (1983)

Nitroarenes were readily transformed to aminoarenes in excellent yields under mild conditions with carbon monoxide and water in the presence of a platinum catalyst.Triethylamine, SnCl4 and PPh3 are essential for the high catalytic activity.Nitroarenes are reduced chemoselectively by this procedure.

Selective Reduction of Nitroarenes to Arylamines by the Cooperative Action of Methylhydrazine and a Tris(N-heterocyclic thioamidate) Cobalt(III) Complex

Ioannou, Dimitris I.,Gioftsidou, Dimitra K.,Tsina, Vasiliki E.,Kallitsakis, Michael G.,Hatzidimitriou, Antonios G.,Terzidis, Michael A.,Angaridis, Panagiotis A.,Lykakis, Ioannis N.

, p. 2895 - 2906 (2021/02/27)

We report an efficient catalytic protocol that chemoselectively reduces nitroarenes to arylamines, by using methylhydrazine as a reducing agent in combination with the easily synthesized and robust catalyst tris(N-heterocyclic thioamidate) Co(III) complex [Co(κS,N-tfmp2S)3], tfmp2S = 4-(trifluoromethyl)-pyrimidine-2-thiolate. A series of arylamines and heterocyclic amines were formed in excellent yields and chemoselectivity. High conversion yields of nitroarenes into the corresponding amines were observed by using polar protic solvents, such as MeOH and iPrOH. Among several hydrogen donors that were examined, methylhydrazine demonstrated the best performance. Preliminary mechanistic investigations, supported by UV-vis and NMR spectroscopy, cyclic voltammetry, and high-resolution mass spectrometry, suggest a cooperative action of methylhydrazine and [Co(κS,N-tfmp2S)3] via a coordination activation pathway that leads to the formation of a reduced cobalt species, responsible for the catalytic transformation. In general, the corresponding N-arylhydroxylamines were identified as the sole intermediates. Nevertheless, the corresponding nitrosoarenes can also be formed as intermediates, which, however, are rapidly transformed into the desired arylamines in the presence of methylhydrazine through a noncatalytic path. On the basis of the observed high chemoselectivity and yields, and the fast and clean reaction processes, the present catalytic system [Co(κS,N-tfmp2S)3]/MeNHNH2 shows promise for the efficient synthesis of aromatic amines that could find various industrial applications.

Fabrication of palladium nanocatalyst supported on magnetic eggshell and its catalytic character in the catalytic reduction of nitroarenes in water

?al??kan, Melike,Akay, Sema,Baran, Talat,Kayan, Berkant

, (2021/07/21)

Aromatic nitro compounds, which have good solubility in water, are highly toxic and non-biodegradable are one of the most important industrial pollutants and have negative effects on human health, aquatic life and the environment. Therefore, the elimination of these harmful organic compounds has become an issue of great importance. For this, in this study we have developed a palladium nanocatalyst supported on Fe3O4-coated eggshell and characterized by FT-IR, XRD, XPS, FE-SEM, TG/DTG, BET, TEM and EDS techniques (Pd-Fe3O4-ES). Also, the quantitative analysis of Pd was determined using ICP-OES. The catalytic behavior of the designed Pd-Fe3O4-ES nanocatalyst was investigated against the catalytic reduction of several highly toxic nitro compounds using NaBH4 in water at room temperature. The progress of the reduction was followed using high performance liquid chromatography (HPLC). The catalytic studies revealed that the nitro compounds were converted into the desired amines by the Pd-Fe3O4-ES nanocatalyst using a very low dose of catalyst (15 mg) and short-duration reactions (81–360 s) in aqueous medium at ambient temperature. Furthermore, the Pd-Fe3O4-ES nanocatalyst showed good catalytic stability by retaining its activity after the fifth catalytic run.

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