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24549-06-2

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24549-06-2 Usage

Chemical Properties

Liquid

Uses

Different sources of media describe the Uses of 24549-06-2 differently. You can refer to the following data:
1. 2-Ethyl-6-methylaniline is an intermediate for the production of alachlor, butachlor, metolachlor-herbicides, tiafentiurone-insecticide, carbodiimide and RIM-PUR Product Data Sheet
2. 2-Ethyl-6-methylaniline is used for the oral toxicity and lipophilicity studies of alkylanilines on rats.
3. 2-Ethyl-6-methylaniline was used in the preparation of racemic esters of N-(2-ethyl-6-methylphenyl)alanine (NEMPA).

General Description

A clear liquid with a pungent odor. Water insoluble and less dense than water. Hence floats on water.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

6-Ethyl-o-toluidine 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. May generate hydrogen, a flammable gas, in combination with strong reducing agents such as hydrides.

Health Hazard

Inhalation causes weakness, reduction in respiratory rate, coma, gradual respiratory failure, and mild cyanosis (high concentrations). Causes severe irritation of the eyes. Ingestion may produce cyanosis.

Check Digit Verification of cas no

The CAS Registry Mumber 24549-06-2 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 2,4,5,4 and 9 respectively; the second part has 2 digits, 0 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 24549-06:
(7*2)+(6*4)+(5*5)+(4*4)+(3*9)+(2*0)+(1*6)=112
112 % 10 = 2
So 24549-06-2 is a valid CAS Registry Number.
InChI:InChI=1/C9H13N/c1-3-8-6-4-5-7(2)9(8)10/h4-6H,3,10H2,1-2H3

24549-06-2 Well-known Company Product Price

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  • Alfa Aesar

  • (A12796)  2-Ethyl-6-methylaniline, 98%   

  • 24549-06-2

  • 100g

  • 242.0CNY

  • Detail
  • Alfa Aesar

  • (A12796)  2-Ethyl-6-methylaniline, 98%   

  • 24549-06-2

  • 500g

  • 1088.0CNY

  • Detail
  • Alfa Aesar

  • (A12796)  2-Ethyl-6-methylaniline, 98%   

  • 24549-06-2

  • 2500g

  • 4613.0CNY

  • Detail

24549-06-2SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name 2-ethyl-6-methylaniline

1.2 Other means of identification

Product number -
Other names EINECS 246-309-6

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Intermediates,Ion exchange agents
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:24549-06-2 SDS

24549-06-2Synthetic route

tert-butyl 2-(2-ethyl-6-methylphenyl)-1-(4-nitrophenyl)hydrazinecarboxylate
1616514-62-5

tert-butyl 2-(2-ethyl-6-methylphenyl)-1-(4-nitrophenyl)hydrazinecarboxylate

acetic anhydride
108-24-7

acetic anhydride

A

6-ethyl-o-toluidine
24549-06-2

6-ethyl-o-toluidine

B

N-(2-ethyl-6-methyl-4-((4-nitrophenyl)amino)phenyl)acetamide

N-(2-ethyl-6-methyl-4-((4-nitrophenyl)amino)phenyl)acetamide

C

1-(2-ethyl-6-methylphenyl)-2-(4-nitrophenyl)diazene
1616514-83-0

1-(2-ethyl-6-methylphenyl)-2-(4-nitrophenyl)diazene

D

3′-ethyl-5′-methyl-5-nitro-1,1′-biphenyl-2,4′-diamine
1616514-70-5

3′-ethyl-5′-methyl-5-nitro-1,1′-biphenyl-2,4′-diamine

E

4-nitro-aniline
100-01-6

4-nitro-aniline

Conditions
ConditionsYield
Stage #1: tert-butyl 2-(2-ethyl-6-methylphenyl)-1-(4-nitrophenyl)hydrazinecarboxylate With hydrogenchloride In ethanol; water at 20℃; for 2h; Inert atmosphere; Reflux;
Stage #2: acetic anhydride
A 11%
B 3%
C 26%
D 3%
E 20%
Stage #1: tert-butyl 2-(2-ethyl-6-methylphenyl)-1-(4-nitrophenyl)hydrazinecarboxylate With hydrogenchloride In ethanol for 2h; Inert atmosphere; Reflux;
Stage #2: acetic anhydride Overall yield = 52 %; regioselective reaction;
A 11%
B 3%
C 26%
D 3%
E 20%
tert-butyl 2-(2-ethyl-6-methylphenyl)-1-(4-(trifluoromethyl)phenyl)hydrazinecarboxylate
1616514-65-8

tert-butyl 2-(2-ethyl-6-methylphenyl)-1-(4-(trifluoromethyl)phenyl)hydrazinecarboxylate

A

4-trifluoromethylphenylamine
455-14-1

4-trifluoromethylphenylamine

B

6-ethyl-o-toluidine
24549-06-2

6-ethyl-o-toluidine

C

3′-ethyl-5′-methyl-5-trifluoromethyl-1,1′-biphenyl-2,4′-diamine
1616514-73-8

3′-ethyl-5′-methyl-5-trifluoromethyl-1,1′-biphenyl-2,4′-diamine

D

3-ethyl-5-methyl-N1-[4-(trifluoromethyl)phenyl]benzene-1,4-diamine
1616514-79-4

3-ethyl-5-methyl-N1-[4-(trifluoromethyl)phenyl]benzene-1,4-diamine

E

1-(2-ethyl-6-methylphenyl)-2-(4-(trifluoromethyl)phenyl)diazene
1616514-85-2

1-(2-ethyl-6-methylphenyl)-2-(4-(trifluoromethyl)phenyl)diazene

Conditions
ConditionsYield
With hydrogenchloride In ethanol; water at 20℃; for 2h; Inert atmosphere; Reflux;A 10%
B 6%
C 10%
D 18%
E 12%
With hydrogenchloride In ethanol for 2h; Inert atmosphere; Reflux; Overall yield = 50 %; regioselective reaction;A 10%
B 6%
C 10%
D 18%
E 12%
2-methyl-6-ethylnitrobenzene
102878-74-0

2-methyl-6-ethylnitrobenzene

6-ethyl-o-toluidine
24549-06-2

6-ethyl-o-toluidine

Conditions
ConditionsYield
With sodium hydroxide; sodium dithionite
ethene
74-85-1

ethene

o-toluidine
95-53-4

o-toluidine

6-ethyl-o-toluidine
24549-06-2

6-ethyl-o-toluidine

1-Methyl-3-ethylbenzene
620-14-4

1-Methyl-3-ethylbenzene

6-ethyl-o-toluidine
24549-06-2

6-ethyl-o-toluidine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sulfuric acid; nitric acid
2: Na2S2O4; aq.-ethanolic NaOH
View Scheme
p-nitrobenzene iodide
636-98-6

p-nitrobenzene iodide

N'-Boc-N-(2-ethyl-6-methylphenyl)hydrazine
1639128-65-6

N'-Boc-N-(2-ethyl-6-methylphenyl)hydrazine

A

6-ethyl-o-toluidine
24549-06-2

6-ethyl-o-toluidine

B

3′-ethyl-5′-methyl-5-nitro-1,1′-biphenyl-2,4′-diamine
1616514-70-5

3′-ethyl-5′-methyl-5-nitro-1,1′-biphenyl-2,4′-diamine

C

4-nitro-aniline
100-01-6

4-nitro-aniline

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1,10-Phenanthroline; caesium carbonate; copper(l) iodide / N,N-dimethyl-formamide / 20 - 80 °C / Inert atmosphere
2: hydrogenchloride / ethanol; water / 2 h / 20 °C / Inert atmosphere; Reflux
View Scheme
4-Iodobenzotrifluoride
455-13-0

4-Iodobenzotrifluoride

N'-Boc-N-(2-ethyl-6-methylphenyl)hydrazine
1639128-65-6

N'-Boc-N-(2-ethyl-6-methylphenyl)hydrazine

A

4-trifluoromethylphenylamine
455-14-1

4-trifluoromethylphenylamine

B

6-ethyl-o-toluidine
24549-06-2

6-ethyl-o-toluidine

C

3′-ethyl-5′-methyl-5-trifluoromethyl-1,1′-biphenyl-2,4′-diamine
1616514-73-8

3′-ethyl-5′-methyl-5-trifluoromethyl-1,1′-biphenyl-2,4′-diamine

D

1-(2-ethyl-6-methylphenyl)-2-(4-(trifluoromethyl)phenyl)diazene
1616514-85-2

1-(2-ethyl-6-methylphenyl)-2-(4-(trifluoromethyl)phenyl)diazene

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1,10-Phenanthroline; caesium carbonate; copper(l) iodide / N,N-dimethyl-formamide / 20 - 80 °C / Inert atmosphere
2: hydrogenchloride / ethanol; water / 2 h / 20 °C / Inert atmosphere; Reflux
View Scheme
6-ethyl-o-toluidine
24549-06-2

6-ethyl-o-toluidine

4-bromo-2-ethyl-6-methylbenzenamine
70598-49-1

4-bromo-2-ethyl-6-methylbenzenamine

Conditions
ConditionsYield
With N-Bromosuccinimide In N,N-dimethyl-formamide at 0 - 20℃;100%
With N-Bromosuccinimide In N,N-dimethyl-formamide at 20℃; for 0.166667h;100%
With sulfuric acid; dihydrogen peroxide; boric acid; potassium bromide In water at 20℃; for 3h;78%
phenylglyoxylyl chloride
25726-04-9

phenylglyoxylyl chloride

6-ethyl-o-toluidine
24549-06-2

6-ethyl-o-toluidine

C17H17NO2
1266932-87-9

C17H17NO2

Conditions
ConditionsYield
With triethylamine In toluene100%
6-ethyl-o-toluidine
24549-06-2

6-ethyl-o-toluidine

C21H33NO2
1349188-26-6

C21H33NO2

C30H44N2O
1349188-63-1

C30H44N2O

Conditions
ConditionsYield
With acetic acid In toluene100%
6-ethyl-o-toluidine
24549-06-2

6-ethyl-o-toluidine

pyruvoyl chloride
5704-66-5

pyruvoyl chloride

C12H15NO2
1267003-21-3

C12H15NO2

Conditions
ConditionsYield
With triethylamine In toluene100%
1-bromo-2-methylnaphtalene
2586-62-1

1-bromo-2-methylnaphtalene

6-ethyl-o-toluidine
24549-06-2

6-ethyl-o-toluidine

N-(2-ethyl-6-methylphenyl)-2-methylnaphthale N-1-amine

N-(2-ethyl-6-methylphenyl)-2-methylnaphthale N-1-amine

Conditions
ConditionsYield
With tris-(dibenzylideneacetone)dipalladium(0); trineopentyl phosphine; sodium t-butanolate In toluene at 80℃; for 48h; Buchwald-Hartwig Coupling; Inert atmosphere;100%
6-ethyl-o-toluidine
24549-06-2

6-ethyl-o-toluidine

chloroacetyl chloride
79-04-9

chloroacetyl chloride

2-chloro-N-(2-ethyl-6-methylphenyl)-N-[(1-methylethoxy)methyl]acetamide
86763-47-5

2-chloro-N-(2-ethyl-6-methylphenyl)-N-[(1-methylethoxy)methyl]acetamide

Conditions
ConditionsYield
Stage #1: 6-ethyl-o-toluidine With Methoxyacetone; toluene-4-sulfonic acid In toluene at 88℃; for 10h;
Stage #2: With hydrogen at 50℃; under 56255.6 Torr; for 4.5h; Autoclave; Inert atmosphere;
Stage #3: chloroacetyl chloride With sodium carbonate In water; toluene at 25℃; for 0.5h; Reagent/catalyst;
98.6%
Methoxyacetone
5878-19-3

Methoxyacetone

6-ethyl-o-toluidine
24549-06-2

6-ethyl-o-toluidine

2-methyl-6-ethyl-N-(1-methyl-2-methoxyethyl)aniline
51219-00-2, 118604-69-6, 118604-70-9

2-methyl-6-ethyl-N-(1-methyl-2-methoxyethyl)aniline

Conditions
ConditionsYield
With phosphoric acid; palladium on activated charcoal; hydrogen In toluene at 70℃; under 11251.1 Torr; for 0.5h; Autoclave;98%
bis(benzyloxy)methane
2749-70-4

bis(benzyloxy)methane

6-ethyl-o-toluidine
24549-06-2

6-ethyl-o-toluidine

2-methyl-6-ethyl-N-(benzyloxymethyl)aniline

2-methyl-6-ethyl-N-(benzyloxymethyl)aniline

Conditions
ConditionsYield
In chlorobenzene at 125 - 132℃; for 11h;97.6%
diisopropoxymethane
2568-89-0

diisopropoxymethane

6-ethyl-o-toluidine
24549-06-2

6-ethyl-o-toluidine

2-methyl-6-ethyl-N-(isopropoxymethyl)aniline

2-methyl-6-ethyl-N-(isopropoxymethyl)aniline

Conditions
ConditionsYield
In chlorobenzene at 130 - 132℃; for 13h;97.2%
bis-methoxymethoxy-methane
13353-03-2

bis-methoxymethoxy-methane

6-ethyl-o-toluidine
24549-06-2

6-ethyl-o-toluidine

2-methyl-6-ethyl-N-(methoxymethoxymethyl)aniline

2-methyl-6-ethyl-N-(methoxymethoxymethyl)aniline

Conditions
ConditionsYield
In benzene at 75 - 80℃; for 18h;97.2%
6-ethyl-o-toluidine
24549-06-2

6-ethyl-o-toluidine

2-Bromoacetyl bromide
598-21-0

2-Bromoacetyl bromide

2-bromo-N-(2'-ethyl-6'-methylphenyl)acetamide
70529-06-5

2-bromo-N-(2'-ethyl-6'-methylphenyl)acetamide

Conditions
ConditionsYield
With triethylamine at 0℃; for 1h; Inert atmosphere;97%
With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 1.5h; bromoacetylation;
With sodium carbonate In water for 0.5h; pH=8 - 9;
6-ethyl-o-toluidine
24549-06-2

6-ethyl-o-toluidine

4-Nitrobenzenesulfonyl chloride
98-74-8

4-Nitrobenzenesulfonyl chloride

N-(2-ethyl-6-methylphenyl)-4-nitrobenzenesulfonamide

N-(2-ethyl-6-methylphenyl)-4-nitrobenzenesulfonamide

Conditions
ConditionsYield
With pyridine In dichloromethane at 20℃; for 2.5h;97%
With pyridine In dichloromethane at -10 - 25℃; for 18h; Solvent; Reagent/catalyst; Cooling with ice;92.9%
With pyridine In dichloromethane at -10 - 25℃; for 18h; Solvent; Reagent/catalyst; Cooling with ice;92.9%
methanol
67-56-1

methanol

(R)-(-)-epichlorohydrin
51594-55-9

(R)-(-)-epichlorohydrin

6-ethyl-o-toluidine
24549-06-2

6-ethyl-o-toluidine

(R)-1-((2-ethyl-6-methylphenyl)amino)-3-methoxypropan-2-ol
1578258-67-9

(R)-1-((2-ethyl-6-methylphenyl)amino)-3-methoxypropan-2-ol

Conditions
ConditionsYield
Stage #1: methanol; (R)-(-)-epichlorohydrin; 6-ethyl-o-toluidine at 70℃; for 6h; Reflux;
Stage #2: With potassium hydroxide at 10 - 30℃; for 8h;
96%
dipropoxymethane
505-84-0

dipropoxymethane

6-ethyl-o-toluidine
24549-06-2

6-ethyl-o-toluidine

2-methyl-6-ethyl-N-(propoxymethyl)aniline

2-methyl-6-ethyl-N-(propoxymethyl)aniline

Conditions
ConditionsYield
In toluene at 105 - 110℃; for 12h;95.2%
Methoxyacetone
5878-19-3

Methoxyacetone

6-ethyl-o-toluidine
24549-06-2

6-ethyl-o-toluidine

(S)-2-ethyl-N-(1-methoxypropan-2-yl)-6-methylaniline
118604-70-9

(S)-2-ethyl-N-(1-methoxypropan-2-yl)-6-methylaniline

Conditions
ConditionsYield
With hydrogen at 80℃; under 37503.8 Torr; for 3h; Pressure; Reagent/catalyst; Autoclave;95%
6-ethyl-o-toluidine
24549-06-2

6-ethyl-o-toluidine

p-toluenesulfonyl chloride
98-59-9

p-toluenesulfonyl chloride

N-(2-ethyl-6-methylphenyl)-4-methylbenzenesulfonamide
135518-57-9

N-(2-ethyl-6-methylphenyl)-4-methylbenzenesulfonamide

Conditions
ConditionsYield
With pyridine Heating / reflux;93%
6-ethyl-o-toluidine
24549-06-2

6-ethyl-o-toluidine

chromium(0) hexacarbonyl
199620-14-9, 13007-92-6

chromium(0) hexacarbonyl

(6-ethyl-2-methylaniline)tricarbonylchromium
93596-66-8

(6-ethyl-2-methylaniline)tricarbonylchromium

Conditions
ConditionsYield
With tetrahydrofuran In tetrahydrofuran; dibutyl ether under N2, educts heated under reflux in n-Bu2O/THF for 22 h in the dark, cooled; filtered through Kieselguhr, evapd. in vac., rinsed with petroleum ether, dissolved in acetone, refiltered, pptd. by addn. of light petroleum, recrystd. from acetone/light petroleum; elem. anal.;93%
6-ethyl-o-toluidine
24549-06-2

6-ethyl-o-toluidine

Acetic formic anhydride
2258-42-6

Acetic formic anhydride

C10H13NO
312488-22-5

C10H13NO

Conditions
ConditionsYield
With sodium hydrogencarbonate In dichloromethane; water at 0 - 20℃;93%
6-ethyl-o-toluidine
24549-06-2

6-ethyl-o-toluidine

maleic acid
110-16-7

maleic acid

N-(2-ethyl-6-methylphenyl)-maleimide
56746-13-5

N-(2-ethyl-6-methylphenyl)-maleimide

Conditions
ConditionsYield
With sodium acetate In ice-water; di-isopropyl ether92.9%
(E)-4-chloropent-2-ene
18610-33-8

(E)-4-chloropent-2-ene

6-ethyl-o-toluidine
24549-06-2

6-ethyl-o-toluidine

2-methyl-6-ethyl-4-(1-methyl-2-butenyl)aniline

2-methyl-6-ethyl-4-(1-methyl-2-butenyl)aniline

Conditions
ConditionsYield
at 170℃;92%
at 170℃; for 2h;86%
1-bromo-2-isopropylbenzene
7073-94-1

1-bromo-2-isopropylbenzene

6-ethyl-o-toluidine
24549-06-2

6-ethyl-o-toluidine

2-ethyl-N-(2-isopropylphenyl)-6-methylaniline

2-ethyl-N-(2-isopropylphenyl)-6-methylaniline

Conditions
ConditionsYield
With tris-(dibenzylideneacetone)dipalladium(0); trineopentyl phosphine; sodium t-butanolate In toluene at 80℃; for 16h; Buchwald-Hartwig Coupling; Inert atmosphere;91%
6-ethyl-o-toluidine
24549-06-2

6-ethyl-o-toluidine

trichloroacetic acid
76-03-9

trichloroacetic acid

2,2,2-Trichloro-N-(2-ethyl-6-methyl-phenyl)-acetamide
113260-60-9

2,2,2-Trichloro-N-(2-ethyl-6-methyl-phenyl)-acetamide

Conditions
ConditionsYield
With phosphorus trichloride at 110℃; for 0.5h;90%
6-ethyl-o-toluidine
24549-06-2

6-ethyl-o-toluidine

C27H20ClNO4S

C27H20ClNO4S

C36H32N2O4S

C36H32N2O4S

Conditions
ConditionsYield
In ethylene glycol at 120℃; for 18h;89.88%
(E)-4-chloropent-2-ene
18610-33-8

(E)-4-chloropent-2-ene

6-ethyl-o-toluidine
24549-06-2

6-ethyl-o-toluidine

N-(1-methyl-2-butenyl)-2-methyl-6-ethylaniline

N-(1-methyl-2-butenyl)-2-methyl-6-ethylaniline

Conditions
ConditionsYield
With triethylamine for 4h; Heating;89%
Product distribution; various anilines and α-chloroalkenes;
3,4-dichloro-2-pentene
26423-64-3

3,4-dichloro-2-pentene

6-ethyl-o-toluidine
24549-06-2

6-ethyl-o-toluidine

4-(2-chloro-1-methyl-2-butenyl)-2,6-methyethylaniline

4-(2-chloro-1-methyl-2-butenyl)-2,6-methyethylaniline

Conditions
ConditionsYield
at 170℃;89%
6-ethyl-o-toluidine
24549-06-2

6-ethyl-o-toluidine

phenylacetylene
536-74-3

phenylacetylene

(2-Ethyl-6-methyl-phenyl)-[1-phenyl-eth-(E)-ylidene]-amine

(2-Ethyl-6-methyl-phenyl)-[1-phenyl-eth-(E)-ylidene]-amine

Conditions
ConditionsYield
With tetrafluoroboric acid diethyl ether; dodecacarbonyl-triangulo-triruthenium at 100℃; for 12h; Addition; Hydroamination;89%
6-ethyl-o-toluidine
24549-06-2

6-ethyl-o-toluidine

dimethylglyoxal
431-03-8

dimethylglyoxal

bis[N,N'-(2-ethyl-6-methylphenyl)imino]-1,2-dimethylethane

bis[N,N'-(2-ethyl-6-methylphenyl)imino]-1,2-dimethylethane

Conditions
ConditionsYield
With formic acid In methanol for 24h; Friedel-Crafts Acylation; Reflux;89%
6-ethyl-o-toluidine
24549-06-2

6-ethyl-o-toluidine

dimedone
126-81-8

dimedone

4-cyanobenzaldehyde
105-07-7

4-cyanobenzaldehyde

C33H36N2O2

C33H36N2O2

Conditions
ConditionsYield
With saponin immobilized on magnetite nanoparticles doped with copper ions In water at 20℃; for 0.416667h;89%
6-ethyl-o-toluidine
24549-06-2

6-ethyl-o-toluidine

itaconic acid anhydride
2170-03-8

itaconic acid anhydride

N-(2-Ethyl-6-methyl-phenyl)-2-methylene-succinamic acid
126404-36-2

N-(2-Ethyl-6-methyl-phenyl)-2-methylene-succinamic acid

Conditions
ConditionsYield
In benzene for 0.5h; Ambient temperature;87%
6-ethyl-o-toluidine
24549-06-2

6-ethyl-o-toluidine

N-(2-ethyl-6-methylphenyl)-4-styrylbenzenamine

N-(2-ethyl-6-methylphenyl)-4-styrylbenzenamine

Conditions
ConditionsYield
With tris-(dibenzylideneacetone)dipalladium(0); sodium; sodium t-butanolate; tricyclohexylphosphine In o-xylene at 120℃; for 5h; Inert atmosphere;86%

24549-06-2Relevant articles and documents

Regioselectivity of the ortho- and para-semidine, and diphenyline rearrangements

Yang, Zhanhui,Hou, Shili,He, Wei,Cheng, Baoxiang,Jiao, Peng,Xu, Jiaxi

, p. 2186 - 2195 (2016/04/09)

The regioselectivity of the o-semidine, p-semidine, and diphenyline rearrangements of unsymmetrical N,N′-diarylhydrazines was studied experimentally. The results indicate that their electron-rich nitrogen atom is first protonated and then the electron-poor non-protonated nitrogen atom undergoes an N[1,3]-sigmatropic shift to the ortho-position of the electron-rich aryl rings, generating key intermediates. The intermediates can undergo (1) a direct proton transfer to give o-semidines, (2) a second N[1,3]-shift of the electron-poor nitrogen atom and then proton transfer to furnish p-semidines, and (3) a [3,3]-sigmatropic shift and subsequent proton transfer to yield diphenylines. It is the first N[1,3]-sigmatropic shift step that plays an important role in controlling the regioselectivity in the three rearrangements, further determining the structures of o-semidines, p-semidines, and diphenylines. The current results provide new insights into the o/p-semidine and diphenyline rearrangements and useful information for controlling and predicting the structures of the rearrangement products.

New diamines and a process for their production

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, (2008/06/13)

New aminoalkyl anilines having the formula: STR1 wherein k is 0 or 1; QNH2 is a residue of formula STR2 which is situated in one of the positions of the benzene ring ortho or para to the amino group and wherein n is an integer from 1 to 15, R1 is C1 -C8 alkyl, R2 is C1 -C4 alkyl or R1 and R2, together with the carbon atom to which they are attached, form a C5 -C8 cycloalkylene residue, R3 is H or C1 -C6 alkyl, C3 -C8 cycloalkyl, or C6 -C10 aryl; and R4 and R5 are H or C1 -C4 alkyl; as well as the corresponding salts of compounds of formula I with organic or inorganic acids and metal salt complexes; process for their production; and their use as intermediates for polyamides.

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