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87-59-2

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87-59-2 Usage

Chemical Properties

brown liquid

Uses

Reagent used in the preparation of non-steroidal anti-inflammatory drugs, dyes and pesticides.

General Description

Dark brown liquid.

Air & Water Reactions

Slightly soluble in water.

Reactivity Profile

2,3-Dimethylaniline reacts with strong oxidizing agents and hypochlorite bleaches . Neutralizes acids in exothermic reactions to form salts plus water. May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen may be generated in combination with strong reducing agents, such as hydrides.

Fire Hazard

2,3-Dimethylaniline is combustible.

Safety Profile

A poison. Moderately toxic by ingestion. Mutation data reported. When heated to decomposition it emits toxic fumes of NOx. See also other xylidine entries.

Purification Methods

Purify vic-xylidine by conversion into a derivative (see below), recrystallise the derivative, decompose the derivative with aqueous NaOH and fractionally distil the liquid base. The acetyl derivative has m 135o (from EtOH), and the formyl derivative has m 102o (from EtOH). [Beilstein 12 H 1101, 12 III 2438, 12 IV 2497.]

Check Digit Verification of cas no

The CAS Registry Mumber 87-59-2 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 8 and 7 respectively; the second part has 2 digits, 5 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 87-59:
(4*8)+(3*7)+(2*5)+(1*9)=72
72 % 10 = 2
So 87-59-2 is a valid CAS Registry Number.
InChI:InChI=1/C8H11N/c1-6-4-3-5-8(9)7(6)2/h3-5H,9H2,1-2H3

87-59-2 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
  • Price
  • Detail
  • Alfa Aesar

  • (A10918)  2,3-Dimethylaniline, 98%   

  • 87-59-2

  • 500g

  • 926.0CNY

  • Detail
  • Alfa Aesar

  • (A10918)  2,3-Dimethylaniline, 98%   

  • 87-59-2

  • 2500g

  • 3412.0CNY

  • Detail
  • Sigma-Aldrich

  • (Y0001081)  MefenamicacidimpurityA  European Pharmacopoeia (EP) Reference Standard

  • 87-59-2

  • Y0001081

  • 1,880.19CNY

  • Detail
  • USP

  • (1211254)  2,3-Dimethylaniline  United States Pharmacopeia (USP) Reference Standard

  • 87-59-2

  • 1211254-50MG

  • 14,500.98CNY

  • Detail

87-59-2Synthetic route

1-tert-butyl-N-(2,3-dimethylphenyl)-1,1-dimethylsilanamine
1321455-35-9

1-tert-butyl-N-(2,3-dimethylphenyl)-1,1-dimethylsilanamine

2,3-Dimethylaniline
87-59-2

2,3-Dimethylaniline

Conditions
ConditionsYield
With silica gel In ethanol; water at 20℃; for 2h;100%
2,3-dimethylnitrobenzene
83-41-0

2,3-dimethylnitrobenzene

2,3-Dimethylaniline
87-59-2

2,3-Dimethylaniline

Conditions
ConditionsYield
With sodium sulfide; tetrabutylammomium bromide In water; toluene at 80℃; for 0.75h; Zinin reduction;96.8%
Stage #1: 2,3-dimethylnitrobenzene In water at 20℃; for 0.05h; Green chemistry;
Stage #2: With glycerol In water at 20℃; for 1.5h; Green chemistry;
95%
With sodium tetrahydroborate In water at 60 - 70℃; for 0.133333h; Green chemistry;95%
2-amino-6-methylbenzoic acid methyl ester
18595-13-6

2-amino-6-methylbenzoic acid methyl ester

2,3-Dimethylaniline
87-59-2

2,3-Dimethylaniline

Conditions
ConditionsYield
With sodium bis(2-methoxyethoxy)aluminium dihydride In toluene for 3h; Heating;75%
o-xylene
95-47-6

o-xylene

A

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

4-amino-o-xylene

B

2,3-Dimethylaniline
87-59-2

2,3-Dimethylaniline

Conditions
ConditionsYield
With tris-(2-chloro-ethyl)-amine; trifluorormethanesulfonic acid; trifluoroacetic acid In chloroform at 25℃; for 1h;A 44%
B 30%
bei der Nitrierung und Hydrierung des Reaktionsprodukts in Gegenwart von Nickel bei 180-190grad;
With xenon difluoride; trimethylsilyl isocyanate; trifluorormethanesulfonic acid In dichloromethane at -78℃;
3,4-dimethylbenzoic acid
619-04-5

3,4-dimethylbenzoic acid

A

3,4-Dimethylphenol
95-65-8

3,4-Dimethylphenol

B

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

4-amino-o-xylene

C

2,3-Dimethylaniline
87-59-2

2,3-Dimethylaniline

Conditions
ConditionsYield
With ammonia; water; copper(II) oxide at 220℃; for 0.5h;A 3.5%
B 43.1%
C 0.9%
2,3-dibromo-5,6-dimethyl-aniline

2,3-dibromo-5,6-dimethyl-aniline

2,3-Dimethylaniline
87-59-2

2,3-Dimethylaniline

Conditions
ConditionsYield
With sodium amalgam
Methyl fluoride
593-53-3

Methyl fluoride

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

1-amino-3-methylbenzene

A

2,5-Dimethylaniline
95-78-3

2,5-Dimethylaniline

B

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

4-amino-o-xylene

C

2,3-Dimethylaniline
87-59-2

2,3-Dimethylaniline

Conditions
ConditionsYield
With oxygen In gaseous matrix at 80℃; Irradiation;A 29 % Spectr.
B 25 % Spectr.
C 46 % Spectr.
2,3-Dichloro-[1,4]naphthoquinone; compound with 2,3-dimethyl-phenylamine

2,3-Dichloro-[1,4]naphthoquinone; compound with 2,3-dimethyl-phenylamine

A

2,3-Dichloro-1,4-naphthoquinone
117-80-6

2,3-Dichloro-1,4-naphthoquinone

B

2,3-Dimethylaniline
87-59-2

2,3-Dimethylaniline

Conditions
ConditionsYield
In dichloromethane at 21.9℃; Equilibrium constant;
2,3-Dichloro-[1,4]naphthoquinone; compound with 2,3-dimethyl-phenylamine

2,3-Dichloro-[1,4]naphthoquinone; compound with 2,3-dimethyl-phenylamine

A

2,3-Dichloro-1,4-naphthoquinone
117-80-6

2,3-Dichloro-1,4-naphthoquinone

B

2,3-Dimethylaniline
87-59-2

2,3-Dimethylaniline

Conditions
ConditionsYield
In dichloromethane at 21.9℃; Equilibrium constant;
3-nitro-o-xylene

3-nitro-o-xylene

2,3-Dimethylaniline
87-59-2

2,3-Dimethylaniline

Conditions
ConditionsYield
With iron; acetic acid
vic nitro-o-xylene

vic nitro-o-xylene

2,3-Dimethylaniline
87-59-2

2,3-Dimethylaniline

Conditions
ConditionsYield
With iron; acetic acid
xylidine

xylidine

2,3-Dimethylaniline
87-59-2

2,3-Dimethylaniline

Conditions
ConditionsYield
With acetic acid in mehrere Stufen;
methanol
67-56-1

methanol

aniline
62-53-3

aniline

A

2,3-Dimethylaniline
87-59-2

2,3-Dimethylaniline

B

Dimethyl-p-toluidine
99-97-8

Dimethyl-p-toluidine

C

homologous/ues (CH3)2C6H3*N(CH3)2 and (CH3)3C6H2*N(CH3)2

homologous/ues (CH3)2C6H3*N(CH3)2 and (CH3)3C6H2*N(CH3)2

D

(CH3)4C6H*N(CH3)2

(CH3)4C6H*N(CH3)2

Conditions
ConditionsYield
at 280 - 300℃; bei der Einwirkung auf salzsaures Anilin im Autoklaven;
hydrogenchloride
7647-01-0

hydrogenchloride

4-(2,3-dimethyl-phenylazo)-2,3-dimethyl-aniline
53877-42-2

4-(2,3-dimethyl-phenylazo)-2,3-dimethyl-aniline

tin

tin

A

1,4-diamino-2,3-dimethylbenzene
5306-96-7

1,4-diamino-2,3-dimethylbenzene

B

2,3-Dimethylaniline
87-59-2

2,3-Dimethylaniline

N-(2,3-dimethylphenyl)hydroxylamine
3096-62-6

N-(2,3-dimethylphenyl)hydroxylamine

alcoholic KOH-solution

alcoholic KOH-solution

A

bis-(2,3-dimethyl-phenyl)-diazene-N-oxide
19618-11-2

bis-(2,3-dimethyl-phenyl)-diazene-N-oxide

B

2,3-Dimethylaniline
87-59-2

2,3-Dimethylaniline

C

3-nitro-o-xylene

3-nitro-o-xylene

sulfuric acid
7664-93-9

sulfuric acid

tetramethyl-[1,4]benzoquinone-(2,3-dimethyl-phenylimine)-imine
861319-17-7

tetramethyl-[1,4]benzoquinone-(2,3-dimethyl-phenylimine)-imine

A

Duroquinone
527-17-3, 70128-24-4

Duroquinone

B

2,3-Dimethylaniline
87-59-2

2,3-Dimethylaniline

2,3-dimethyl-6-(trisopropylsilyl)aniline
476170-48-6

2,3-dimethyl-6-(trisopropylsilyl)aniline

2,3-Dimethylaniline
87-59-2

2,3-Dimethylaniline

Conditions
ConditionsYield
With trifluoroacetic acid In hexane for 5h; Heating;0.65 g
2-methoxycarbonyl-3-methyl-6-(trisopropylsilyl)aniline
110036-12-9

2-methoxycarbonyl-3-methyl-6-(trisopropylsilyl)aniline

2,3-Dimethylaniline
87-59-2

2,3-Dimethylaniline

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 3.85 g / Red-Al / toluene / 3 h / Heating
2: 0.65 g / trifluoroacetic acid / hexane / 5 h / Heating
View Scheme
2-methoxycarbonyl-3-methyl-6,N-bis(trisopropylsilyl)aniline
476170-47-5

2-methoxycarbonyl-3-methyl-6,N-bis(trisopropylsilyl)aniline

2,3-Dimethylaniline
87-59-2

2,3-Dimethylaniline

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 91 percent / KF; HCl; water / methanol / 2 h / Heating
2: 75 percent / Red-Al / toluene / 3 h / Heating
View Scheme
Multi-step reaction with 3 steps
1: 62 percent / KF; HCl; water / methanol / 2 h / Heating
2: 3.85 g / Red-Al / toluene / 3 h / Heating
3: 0.65 g / trifluoroacetic acid / hexane / 5 h / Heating
View Scheme
dimethylaniline oxide

dimethylaniline oxide

1-amino-9,10-anthracenedione
82-45-1

1-amino-9,10-anthracenedione

A

dianthraquinone-N,N'-dihydroazine

dianthraquinone-N,N'-dihydroazine

B

2,3-Dimethylaniline
87-59-2

2,3-Dimethylaniline

Conditions
ConditionsYield
With potassium hydroxide; sodium hydroxide
2,3-Dimethylaniline
87-59-2

2,3-Dimethylaniline

trifluoroacetic anhydride
407-25-0

trifluoroacetic anhydride

N-(2,3-dimethylphenyl)-2,2,2-trifluoroacetamide
14719-31-4

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

Conditions
ConditionsYield
In dichloromethane for 1h; Further stages;100%
With triethylamine In dichloromethane for 1h; Ambient temperature;87%
In diethyl ether
In dichloromethane at 0 - 20℃; for 12h;
2-Bromoacetyl bromide
598-21-0

2-Bromoacetyl bromide

2,3-Dimethylaniline
87-59-2

2,3-Dimethylaniline

2-bromo-N-(2',3'-dimethylphenyl)acetamide
349120-89-4

2-bromo-N-(2',3'-dimethylphenyl)acetamide

Conditions
ConditionsYield
With triethylamine at 0℃; for 1h; Inert atmosphere;100%
With sodium carbonate In water pH=9 - 10;99%
With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 1.5h; bromoacetylation;
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

2,3-Dimethylaniline
87-59-2

2,3-Dimethylaniline

N-tert-butyloxycarbonyl-2,3-dimethylaniline
876353-79-6

N-tert-butyloxycarbonyl-2,3-dimethylaniline

Conditions
ConditionsYield
With sodium carbonate In methanol at 20℃; for 1.5h;100%
In neat (no solvent) at 80℃; for 0.166667h; Green chemistry; chemoselective reaction;98%
at 20℃; for 0.0833333h; Green chemistry;95%
With pyridinium trifluroacetate In neat (no solvent) at 20℃; for 0.3h; Green chemistry;93%
In tetrahydrofuran for 12h; Reflux;
triethanolamine
102-71-6

triethanolamine

2,3-Dimethylaniline
87-59-2

2,3-Dimethylaniline

6,7-dimethyl-1H-indole
55199-24-1

6,7-dimethyl-1H-indole

Conditions
ConditionsYield
With tin(ll) chloride; ruthenium trichloride; triphenylphosphine In 1,4-dioxane at 180℃; for 20h;99%
2,3-Dimethylaniline
87-59-2

2,3-Dimethylaniline

MORPHIN
57-27-2

MORPHIN

codeine
76-57-3

codeine

Conditions
ConditionsYield
With potassium carbonate In 5,5-dimethyl-1,3-cyclohexadiene99%
N-tert-butoxycarbonyl-L-leucine
13139-15-6

N-tert-butoxycarbonyl-L-leucine

2,3-Dimethylaniline
87-59-2

2,3-Dimethylaniline

(S)-Boc-L-Leu-N'-(2,3-dimethylphenyl)amide

(S)-Boc-L-Leu-N'-(2,3-dimethylphenyl)amide

Conditions
ConditionsYield
Stage #1: N-tert-butoxycarbonyl-L-leucine With 4-methyl-morpholine; isobutyl chloroformate In tetrahydrofuran at 0℃; for 0.5h; Inert atmosphere; Schlenk technique;
Stage #2: 2,3-Dimethylaniline In tetrahydrofuran at 0 - 20℃; Inert atmosphere; Schlenk technique;
99%
acetic anhydride
108-24-7

acetic anhydride

2,3-Dimethylaniline
87-59-2

2,3-Dimethylaniline

N-(2,3-dimethylphenyl)acetamide
134-98-5

N-(2,3-dimethylphenyl)acetamide

Conditions
ConditionsYield
With Ni2B-Cu2O nanocomposite In neat (no solvent) at 40℃; for 0.0166667h; Reagent/catalyst;98%
In chloroform at 20℃; for 2h;88%
With pyridine at 0 - 20℃;80%
Benzoyl isothiocyanate
532-55-8

Benzoyl isothiocyanate

2,3-Dimethylaniline
87-59-2

2,3-Dimethylaniline

1-benzoyl-3-(2,3-dimethylphenyl)thiourea
83697-76-1

1-benzoyl-3-(2,3-dimethylphenyl)thiourea

Conditions
ConditionsYield
In acetone at 20℃; for 1h;98%
In tetrahydrofuran at 60 - 65℃; for 0.166667h; Microwave irradiation;92%
In acetone85%
N-Boc-D-Leu
16937-99-8

N-Boc-D-Leu

2,3-Dimethylaniline
87-59-2

2,3-Dimethylaniline

N-Boc-D-Leu-N'-(2,3-dimethylphenyl)amide

N-Boc-D-Leu-N'-(2,3-dimethylphenyl)amide

Conditions
ConditionsYield
Stage #1: N-Boc-D-Leu With 4-methyl-morpholine; isobutyl chloroformate In tetrahydrofuran at 0℃; for 0.5h; Inert atmosphere; Schlenk technique;
Stage #2: 2,3-Dimethylaniline In tetrahydrofuran at 0 - 20℃; Inert atmosphere; Schlenk technique;
98%
4-chloromethoxybenzene
623-12-1

4-chloromethoxybenzene

2,3-Dimethylaniline
87-59-2

2,3-Dimethylaniline

C15H17NO

C15H17NO

Conditions
ConditionsYield
With 2'-dicyclohexylphosphanyl-6-hydroxy-biphenyl-3-sulfonic acid; palladium diacetate; sodium t-butanolate In diethylene glycol dimethyl ether at 120℃; for 14h; Buchwald-Hartwig Coupling; Inert atmosphere;98%
benzenesulfonyl chloride
98-09-9

benzenesulfonyl chloride

2,3-Dimethylaniline
87-59-2

2,3-Dimethylaniline

2,3-dimethyl-N-(phenylsulfonyl)aniline
126494-77-7

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

Conditions
ConditionsYield
With pyridine In dichloromethane97%
C10H14O5
845870-02-2

C10H14O5

2,3-Dimethylaniline
87-59-2

2,3-Dimethylaniline

dimethyl (1S,2S,4S,5S)-4-(2,3-dimethylphenylamino)-5-hydroxycyclohexane-1,2-dicarboxylate
1254946-88-7

dimethyl (1S,2S,4S,5S)-4-(2,3-dimethylphenylamino)-5-hydroxycyclohexane-1,2-dicarboxylate

Conditions
ConditionsYield
With indium(III) bromide In dichloromethane at 20℃; for 15h;97%
2-azidobenzaldehyde
16714-25-3

2-azidobenzaldehyde

2,3-Dimethylaniline
87-59-2

2,3-Dimethylaniline

C15H14N2

C15H14N2

Conditions
ConditionsYield
at 100℃; under 10343.2 Torr; Microwave irradiation;97%
phenylethane 1,2-diol
93-56-1

phenylethane 1,2-diol

2,3-Dimethylaniline
87-59-2

2,3-Dimethylaniline

6,7-dimethyl-2-phenyl-1H-indole
33555-28-1

6,7-dimethyl-2-phenyl-1H-indole

Conditions
ConditionsYield
With tetrafluoroboric acid diethyl ether; {[(PCy3)(CO)RuH]4(μ-O)(μ-OH)2}; cyclopentene In 1,4-dioxane at 120℃; for 14h; Sealed tube; Schlenk technique; Inert atmosphere; regioselective reaction;97%
2-acetyl-benzoic acid
577-56-0

2-acetyl-benzoic acid

2,3-Dimethylaniline
87-59-2

2,3-Dimethylaniline

2-(2,3-dimethylphenyl)-3-methyleneisoindolin-1-one

2-(2,3-dimethylphenyl)-3-methyleneisoindolin-1-one

Conditions
ConditionsYield
With 3-(1,1-dioxido-4-(3-(3-(3-sulfopropyl)-1H-imidazol-3-ium-1-yl)propyl)thiomorpholino-4-ium)propane-1-sulfonate trifluoromethanesulfonate In acetic acid butyl ester at 100℃; for 8h; Green chemistry;97%
chloroacetyl chloride
79-04-9

chloroacetyl chloride

2,3-Dimethylaniline
87-59-2

2,3-Dimethylaniline

2-chloro-N-(2, 3-dimethylphenyl)acetamide
2564-07-0

2-chloro-N-(2, 3-dimethylphenyl)acetamide

Conditions
ConditionsYield
With sodium hydroxide In dichloromethane; water for 18h;96%
With potassium carbonate In acetone at 20℃;83%
In benzene for 5h; Heating;60%
2,3-Dimethylaniline
87-59-2

2,3-Dimethylaniline

2-chloro-N-(2, 3-dimethylphenyl)acetamide
2564-07-0

2-chloro-N-(2, 3-dimethylphenyl)acetamide

Conditions
ConditionsYield
96%
bromochlorobenzene
106-39-8

bromochlorobenzene

2,3-Dimethylaniline
87-59-2

2,3-Dimethylaniline

2,3-dimethyl-4',4
1616092-86-4

2,3-dimethyl-4',4"-dichlorotriphenylamine

Conditions
ConditionsYield
With bis-triphenylphosphine-palladium(II) chloride; triphenylphosphine; sodium t-butanolate In o-xylene for 12h; Inert atmosphere; Reflux; Schlenk technique;96%
3-chlorobenzoyl isothiocyanate
66090-36-6

3-chlorobenzoyl isothiocyanate

2,3-Dimethylaniline
87-59-2

2,3-Dimethylaniline

1-(3-chlorobenzoyl)-3-(2,3-dimethylphenyl)thiourea

1-(3-chlorobenzoyl)-3-(2,3-dimethylphenyl)thiourea

Conditions
ConditionsYield
In tetrahydrofuran at 60 - 65℃; under 760.051 Torr; for 0.025h; Microwave irradiation;96%
potassium methanethiolate
26385-24-0

potassium methanethiolate

2,3-Dimethylaniline
87-59-2

2,3-Dimethylaniline

1,2-dimethyl-3-(methylsulfanyl)benzene
66794-10-3

1,2-dimethyl-3-(methylsulfanyl)benzene

Conditions
ConditionsYield
Stage #1: 2,3-Dimethylaniline With sulfuric acid at 50℃; for 0.5h;
Stage #2: With sodium nitrite In water at -10 - -5℃; for 1h;
Stage #3: potassium methanethiolate In water at 20 - 35℃; for 4h;
95.8%
2,3-Dimethylaniline
87-59-2

2,3-Dimethylaniline

sodium thiomethoxide
5188-07-8

sodium thiomethoxide

1,2-dimethyl-3-(methylsulfanyl)benzene
66794-10-3

1,2-dimethyl-3-(methylsulfanyl)benzene

Conditions
ConditionsYield
Stage #1: 2,3-Dimethylaniline With hydrogenchloride In water at 50℃; for 0.5h;
Stage #2: With sodium nitrite In water at -5 - 0℃; for 1h;
Stage #3: sodium thiomethoxide In water at 35℃; for 2h;
95.5%
2,3-Dimethylaniline
87-59-2

2,3-Dimethylaniline

3-nitrobenzenesulphonyl chloride
121-51-7

3-nitrobenzenesulphonyl chloride

3-nitro-N-(2,3-dimethylphenyl)benzenesulfonamide
250697-59-7

3-nitro-N-(2,3-dimethylphenyl)benzenesulfonamide

Conditions
ConditionsYield
With 4-methyl-morpholine In dichloromethane at 0℃;95%
With 4-methyl-morpholine In dichloromethane at 0℃; for 12h; Acylation;95%
With 4-methyl-morpholine In dichloromethane at 0 - 20℃; Substitution;
tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

2,3-Dimethylaniline
87-59-2

2,3-Dimethylaniline

1-tert-butyl-N-(2,3-dimethylphenyl)-1,1-dimethylsilanamine
1321455-35-9

1-tert-butyl-N-(2,3-dimethylphenyl)-1,1-dimethylsilanamine

Conditions
ConditionsYield
Stage #1: 2,3-Dimethylaniline With methyllithium In 2-methyltetrahydrofuran; diethyl ether at 0℃; Inert atmosphere;
Stage #2: tert-butyldimethylsilyl chloride In 2-methyltetrahydrofuran; diethyl ether at 0 - 20℃; Inert atmosphere;
95%
phenylacetylene
536-74-3

phenylacetylene

2,3-Dimethylaniline
87-59-2

2,3-Dimethylaniline

2,3-dimethyl-N-(1-phenylethylidene)benzenamine
1272320-35-0

2,3-dimethyl-N-(1-phenylethylidene)benzenamine

Conditions
ConditionsYield
With silver trifluoromethanesulfonate; C17H25Cl2N3OPtS In toluene at 120℃; for 12h; Reagent/catalyst;95%
With trifluorormethanesulfonic acid; [(S(CH2CH2C3H2N2(Bn))2-κ3C,C',S)PdBr]Br In toluene at 100℃; for 12h;48 %Chromat.
para-bromotoluene
106-38-7

para-bromotoluene

2,3-Dimethylaniline
87-59-2

2,3-Dimethylaniline

2,3,4’,4’’-tetramethyltriphenylamine
1616092-85-3

2,3,4’,4’’-tetramethyltriphenylamine

Conditions
ConditionsYield
With bis-triphenylphosphine-palladium(II) chloride; triphenylphosphine; sodium t-butanolate In o-xylene for 12h; Inert atmosphere; Reflux; Schlenk technique;95%
2-bromoanisole
578-57-4

2-bromoanisole

2,3-Dimethylaniline
87-59-2

2,3-Dimethylaniline

(2,3-dimethyl-phenyl)-(2-methoxyphenyl)-amine

(2,3-dimethyl-phenyl)-(2-methoxyphenyl)-amine

Conditions
ConditionsYield
With tris-(dibenzylideneacetone)dipalladium(0); (RSp,SRp)-tert-butyl([2.2]paracyclophan-4-yl)phosphine oxide; sodium t-butanolate In toluene at 105℃; Buchwald-Hartwig Coupling;95%
With 2'-dicyclohexylphosphanyl-6-methoxy-biphenyl-3-sulfonic acid; palladium diacetate; sodium t-butanolate In diethylene glycol dimethyl ether at 120℃; for 48h; Buchwald-Hartwig Coupling; Inert atmosphere;27%
2-bromonaphthalene
580-13-2

2-bromonaphthalene

2,3-Dimethylaniline
87-59-2

2,3-Dimethylaniline

(2,3-dimethylphenyl)(2-naphthyl)amine

(2,3-dimethylphenyl)(2-naphthyl)amine

Conditions
ConditionsYield
With 2'-dicyclohexylphosphanyl-6-methoxy-biphenyl-3-sulfonic acid; palladium diacetate; sodium t-butanolate In diethylene glycol dimethyl ether at 120℃; for 96h; Buchwald-Hartwig Coupling; Inert atmosphere;95%
2,3-Dimethylaniline
87-59-2

2,3-Dimethylaniline

ortho-chlorobenzoic acid
118-91-2

ortho-chlorobenzoic acid

mefenamic Acid
61-68-7

mefenamic Acid

Conditions
ConditionsYield
Stage #1: ortho-chlorobenzoic acid With sodium carbonate In N,N-dimethyl-formamide at 80℃; for 0.5h;
Stage #2: 2,3-Dimethylaniline With manganese(II) acetate In water; N,N-dimethyl-formamide; toluene at 120 - 130℃; Reagent/catalyst;
94.8%
Stage #1: ortho-chlorobenzoic acid With sodium carbonate In N,N-dimethyl-formamide at 80℃; for 1.16667h;
Stage #2: 2,3-Dimethylaniline With copper In water; N,N-dimethyl-formamide; toluene at 104 - 123℃;
91.3%
With copper; sodium carbonate In N,N-dimethyl-formamide at 140℃; for 2h;90%

87-59-2Relevant articles and documents

Electrophilic Amination of Methylbenzenes with the System NaN 3-AlCl3-HCl. Effects of the Solvent, Crown Ether, and Substrate Structure

Borodkin,Elanov,Popov,Pokrovskii,Shubin

, p. 672 - 679 (2003)

Using mesitylene and o-xylene as examples, it was shown that the solvent nature strongly affects the conversion of methylbenzenes in electrophilic amination with the system NaN3-AlCl3-HCl. Two-parameter correlations were found between the substrate conversion, on the one hand, and dielectric constant and number of heavy atoms in the solvent, on the other. A considerable solvent effect on the regioselectivity of amination of o-xylene was observed. The presence of 18-crown-6 weakly affects the ratio of isomeric amines, but the conversion of o-xylene sharply decreases. Solid aromatic substrates, such as durene and pentamethylbenzene can also be involved in electrophilic amination with the system NaN3-AlCl3-HCl. On the basis of the experimental data and the results of quantum-chemical calculations, participation of a nitrenium intermediate in this reaction was postulated.

-

Tarabrin et al.

, (1976)

-

Pd nanoparticles/graphene quantum dot supported on chitosan as a new catalyst for the reduction of nitroarenes to arylamines

Kalanpour, Nastaran,Nejati, Saeid,Keshipour, Sajjad

, p. 1243 - 1250 (2020/10/29)

A new heterogeneous catalyst was obtained by growing graphene quantum dots on chitosan and subsequent immobilization of Pd nanoparticles. The catalyst after characterization was used in the reduction of nitroarenes to the corresponding amines by NaBH4 as a weak reducing agent of nitro compounds. The catalyst exhibited excellent catalytic activity and selectivity under mild reaction conditions in water as a green solvent during 1?h. Additionally, the catalyst can be reused for five consecutive runs without any significant decrease in its activity and selectivity.

The immobilized Cu nanoparticles on magnetic montmorillonite (MMT?Fe3O4?Cu): As an efficient and reusable nanocatalyst for reduction and reductive-acetylation of nitroarenes with NaBH4

Zeynizadeh, Behzad,Rahmani, Soleiman,Tizhoush, Hengameh

, (2019/11/28)

In this study, the immobilization of copper nanoparticles on superparamagnetic montmorillonite, MMT?Fe3O4?Cu, was studied. Magnetically nanoparticles (MNPs) of iron oxide (Fe3O4) were primarily prepared by a chemical co-precipitation method. Next, the prepared Fe3O4 MNPs were intercalated within the interlamellar spaces and external surface of sodium-exchanged montmorillonite. Finally, Cu NPs were immobilized on magnetic montmorillonite by a simply mixing of an aqueous solution of CuCl2·2H2O with MMT?Fe3O4 followed by the reduction with NaBH4. Characterization of MMT?Fe3O4 clay system represented that through the immobilization of Fe3O4 MNPs, disordered-layers structure of MMT was easily reorganized to an ordered-layers arrangement. The synthesized composite systems were characterized using FT-IR, SEM, EDX, XRD, VSM, BET and ICP-OES analyses. SEM analysis exhibited that dispersion of Cu NPs, with the size distribution of 15–25 nm, on the surface of magnetic clay was taken place perfectly. BET surface analysis indicated that after the immobilization of Fe3O4 and Cu species, the surface area and total pore volume of MMT?Fe3O4?Cu system was decreased. Next, the Cu-clay nanocomposite system showed a perfect catalytic activity towards reduction of nitroarenes to anilines as well as reductive-acetylation of nitroarenes to acetanilides using NaBH4 and Ac2O in water as a green and economic solvent. The copper magnetic clay catalyst can be easily separated from the reaction mixture by an external magnetic field and reused for six consecutive cycles without the significant loss of its catalytic activity.

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