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823-40-5 Usage

Definition

ChEBI: A diamine that is toluene in which both of the hydrogens ortho- to the methyl group are replaced by amino groups.

Production Methods

2,6-Toluenediamine is usually produced as a by-product with 2,4-TDA in mixtures containing 20% 2,6-isomer and 80% 2,4-isomer. It is used primarily in the manufacture of toluene diisocyanate, the predominant isocyanate in the flexible polyurethane foams and elastomers industry. Human exposure to 2,6-TDA may occur indirectly via exposure to toluene diisocyanate mixture containing 2,6- toluenediisocyanate, which is known to hydrolyze to 2,6- TDA rapidly upon contact with water. Workers in some plastics and elastomers industries may be exposed to atmosphere containing TDI.

General Description

Colorless prisms (from water).

Air & Water Reactions

Water soluble.

Reactivity Profile

2,6-Diaminotoluene 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.

Health Hazard

ACUTE/CHRONIC HAZARDS: 2,6-Diaminotoluene is toxic. It is a local irritant.

Fire Hazard

Flash point data for 2,6-Diaminotoluene are not available. 2,6-Diaminotoluene is probably combustible.

Check Digit Verification of cas no

The CAS Registry Mumber 823-40-5 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 8,2 and 3 respectively; the second part has 2 digits, 4 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 823-40:
(5*8)+(4*2)+(3*3)+(2*4)+(1*0)=65
65 % 10 = 5
So 823-40-5 is a valid CAS Registry Number.
InChI:InChI=1/C7H10N2/c1-5-6(8)3-2-4-7(5)9/h2-4H,8-9H2,1H3

823-40-5 Well-known Company Product Price

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

  • (L04278)  2,6-Diaminotoluene, 97%   

  • 823-40-5

  • 5g

  • 316.0CNY

  • Detail
  • Alfa Aesar

  • (L04278)  2,6-Diaminotoluene, 97%   

  • 823-40-5

  • 25g

  • 1041.0CNY

  • Detail
  • Sigma-Aldrich

  • (45921)  2-Methyl-m-phenylenediamine  analytical standard

  • 823-40-5

  • 45921-250MG

  • 377.91CNY

  • Detail
  • Aldrich

  • (148113)  2,6-Diaminotoluene  97%

  • 823-40-5

  • 148113-5G

  • 542.88CNY

  • Detail
  • Aldrich

  • (148113)  2,6-Diaminotoluene  97%

  • 823-40-5

  • 148113-25G

  • 508.95CNY

  • Detail

823-40-5SDS

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 2,6-diaminotoluene

1.2 Other means of identification

Product number -
Other names 1,3-Benzenediamine, 2-methyl-

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. CBI,Intermediates
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:823-40-5 SDS

823-40-5Synthetic route

2,6-dinitrotoluene
606-20-2

2,6-dinitrotoluene

2,6-Diaminotoluene
823-40-5

2,6-Diaminotoluene

Conditions
ConditionsYield
With hydrogen In methanol at 50℃; under 1500.15 Torr; for 0.666667h; Inert atmosphere;100%
With Fe3O4Rh; hydrazine hydrate In ethanol at 80℃; for 2h; Inert atmosphere;99%
With hydrogen In ethanol at 20℃; under 760.051 Torr; for 1h;99%
2,6-Toluene diisocyanate
91-08-7

2,6-Toluene diisocyanate

2,6-Diaminotoluene
823-40-5

2,6-Diaminotoluene

Conditions
ConditionsYield
With formic acid; trifluoroborane diethyl ether94%
With water In 1,2-dimethoxyethane at 37℃; for 0.0166667h; Kinetics; Further Variations:; Solvents; Reaction partners; Hydrolysis;10.7%
3-chloro-2-methylbenzenamine
87-60-5

3-chloro-2-methylbenzenamine

2,6-Diaminotoluene
823-40-5

2,6-Diaminotoluene

Conditions
ConditionsYield
With ammonium hydroxide; urea; copper(l) chloride at 160℃; under 17251.7 Torr; for 20h; Reagent/catalyst; Temperature; Pressure; Autoclave;85.5%
3-nitro-o-tolylamine
603-83-8

3-nitro-o-tolylamine

2,6-Diaminotoluene
823-40-5

2,6-Diaminotoluene

Conditions
ConditionsYield
With hydrogenchloride; tin; tin(ll) chloride auf dem Wasserbade;
With formic acid In ethanol; water at 20℃; for 1h;
With sodium tetrahydroborate In ethanol; water at 25℃; for 0.5h;
With hydrazine hydrate In ethanol at 80℃; for 0.483333h; Catalytic behavior;
With hydrazine hydrate In ethanol at 90℃; for 14h; Catalytic behavior; Green chemistry;
hydrogenchloride
7647-01-0

hydrogenchloride

3-nitro-o-tolylamine
603-83-8

3-nitro-o-tolylamine

tin

tin

2,6-Diaminotoluene
823-40-5

2,6-Diaminotoluene

ethanol
64-17-5

ethanol

2,6-dinitrotoluene
606-20-2

2,6-dinitrotoluene

palladium charcoal

palladium charcoal

A

2,6-Diaminotoluene
823-40-5

2,6-Diaminotoluene

B

2-hydroxylamino-6-nitrotoluene
5805-95-8

2-hydroxylamino-6-nitrotoluene

Conditions
ConditionsYield
Hydrogenation;
sulfuric acid
7664-93-9

sulfuric acid

2,6-dinitrotoluene
606-20-2

2,6-dinitrotoluene

vanadium compound

vanadium compound

A

2,6-Diaminotoluene
823-40-5

2,6-Diaminotoluene

B

3-nitro-o-tolylamine
603-83-8

3-nitro-o-tolylamine

C

6,6'-Dinitro-2,2'-azoxytoluene
5806-00-8

6,6'-Dinitro-2,2'-azoxytoluene

Conditions
ConditionsYield
bei der elektrolytischen Reduktion;
2,6-dinitrotoluene
606-20-2

2,6-dinitrotoluene

A

2,6-Diaminotoluene
823-40-5

2,6-Diaminotoluene

B

3-nitro-o-tolylamine
603-83-8

3-nitro-o-tolylamine

Conditions
ConditionsYield
In phosphate buffer pH=2; Electrochemical reaction;
(S)-2-Amino-4-[(R)-2-{3-[(R)-2-((S)-4-amino-4-carboxy-butyrylamino)-2-(carboxymethyl-carbamoyl)-ethylsulfanylcarbonylamino]-2-methyl-phenylcarbamoylsulfanyl}-1-(carboxymethyl-carbamoyl)-ethylcarbamoyl]-butyric acid
188910-15-8

(S)-2-Amino-4-[(R)-2-{3-[(R)-2-((S)-4-amino-4-carboxy-butyrylamino)-2-(carboxymethyl-carbamoyl)-ethylsulfanylcarbonylamino]-2-methyl-phenylcarbamoylsulfanyl}-1-(carboxymethyl-carbamoyl)-ethylcarbamoyl]-butyric acid

A

2,6-Diaminotoluene
823-40-5

2,6-Diaminotoluene

B

2-amino-6-isocyanatotoluene

2-amino-6-isocyanatotoluene

C

(S)-2-Amino-4-[(R)-2-(3-amino-2-methyl-phenylcarbamoylsulfanyl)-1-(carboxymethyl-carbamoyl)-ethylcarbamoyl]-butyric acid

(S)-2-Amino-4-[(R)-2-(3-amino-2-methyl-phenylcarbamoylsulfanyl)-1-(carboxymethyl-carbamoyl)-ethylcarbamoyl]-butyric acid

D

(S)-2-Amino-4-[(R)-1-(carboxymethyl-carbamoyl)-2-(3-isocyanato-2-methyl-phenylcarbamoylsulfanyl)-ethylcarbamoyl]-butyric acid

(S)-2-Amino-4-[(R)-1-(carboxymethyl-carbamoyl)-2-(3-isocyanato-2-methyl-phenylcarbamoylsulfanyl)-ethylcarbamoyl]-butyric acid

Conditions
ConditionsYield
With Hank's balanced salts solution at 25℃; for 72h; Kinetics; Product distribution; Further Variations:; Temperatures;
2,4-dinitrotoluene
121-14-2

2,4-dinitrotoluene

3,5-dinitrotoluene
618-85-9

3,5-dinitrotoluene

2,6-dinitrotoluene
606-20-2

2,6-dinitrotoluene

1-methyl-2,3-dinitrobenzene
602-01-7

1-methyl-2,3-dinitrobenzene

3,4-Dinitrotoluene
610-39-9

3,4-Dinitrotoluene

2,5-dinitrotoluene
619-15-8

2,5-dinitrotoluene

A

3,5-diaminotoluene
108-71-4

3,5-diaminotoluene

B

2,6-Diaminotoluene
823-40-5

2,6-Diaminotoluene

C

4-methylbenzene-1,3-diamine
95-80-7

4-methylbenzene-1,3-diamine

D

4-methyl-1,2-diaminobenzene
496-72-0

4-methyl-1,2-diaminobenzene

E

2-methyl-p-phenylenediamine
95-70-5

2-methyl-p-phenylenediamine

F

3-methyl-1,2-benzenediamine
2687-25-4

3-methyl-1,2-benzenediamine

Conditions
ConditionsYield
With hydrogen; nickel at 120 - 140℃; under 11251.1 - 22502.3 Torr; Product distribution / selectivity;
1-methyl-4-nitrobenzene
99-99-0

1-methyl-4-nitrobenzene

2,4-dinitrotoluene
121-14-2

2,4-dinitrotoluene

3,5-dinitrotoluene
618-85-9

3,5-dinitrotoluene

2,6-dinitrotoluene
606-20-2

2,6-dinitrotoluene

1-methyl-2,3-dinitrobenzene
602-01-7

1-methyl-2,3-dinitrobenzene

2,5-dinitrotoluene
619-15-8

2,5-dinitrotoluene

A

methylcyclohexylamine

methylcyclohexylamine

B

methylcyclohexyldiamine

methylcyclohexyldiamine

C

toluidine

toluidine

D

3,5-diaminotoluene
108-71-4

3,5-diaminotoluene

E

2,6-Diaminotoluene
823-40-5

2,6-Diaminotoluene

F

4-methylbenzene-1,3-diamine
95-80-7

4-methylbenzene-1,3-diamine

G

2-methyl-p-phenylenediamine
95-70-5

2-methyl-p-phenylenediamine

H

3-methyl-1,2-benzenediamine
2687-25-4

3-methyl-1,2-benzenediamine

Conditions
ConditionsYield
With hydrogen at 170 - 215.6℃; under 67.5068 Torr;
2,4-dinitrotoluene
121-14-2

2,4-dinitrotoluene

2,6-dinitrotoluene
606-20-2

2,6-dinitrotoluene

A

2,6-Diaminotoluene
823-40-5

2,6-Diaminotoluene

B

4-methylbenzene-1,3-diamine
95-80-7

4-methylbenzene-1,3-diamine

Conditions
ConditionsYield
With hydrogen; Ni hydrogenation catalyst In water at 120 - 122℃; under 18751.9 Torr;
With hydrogen; nickel In water at 180℃; under 19502 Torr; for 18 - 215h; Product distribution / selectivity;
With hydrogen; nickel on SiO2 and ZrO2 mixture In water at 116 - 126℃; under 18751.9 Torr; Product distribution / selectivity; Inert atmosphere; Industry scale;
1,2-dichloro-4-methyl-3,5-dinitro-benzene
53278-85-6

1,2-dichloro-4-methyl-3,5-dinitro-benzene

2,6-Diaminotoluene
823-40-5

2,6-Diaminotoluene

Conditions
ConditionsYield
With sodium hydroxide; calcium carbonate; aluminum nickel In methanol
2,6-diamino-3,4-dichlorotoluene

2,6-diamino-3,4-dichlorotoluene

2,6-Diaminotoluene
823-40-5

2,6-Diaminotoluene

Conditions
ConditionsYield
With calcium oxide In palladium on charcoal; isopropyl alcohol
2,6-dichlorotoluene
118-69-4

2,6-dichlorotoluene

2,6-Diaminotoluene
823-40-5

2,6-Diaminotoluene

Conditions
ConditionsYield
With ammonium hydroxide; C30H42NOP*C9H9ClPd In ethanol at 80℃; under 760.051 Torr; for 8h; Catalytic behavior; Temperature;58.3 g
2,6-Diaminotoluene
823-40-5

2,6-Diaminotoluene

chloroformic acid ethyl ester
541-41-3

chloroformic acid ethyl ester

ethyl N-(3-ethoxycarbonylamino-2-methylphenyl)carbamate
16648-51-4

ethyl N-(3-ethoxycarbonylamino-2-methylphenyl)carbamate

Conditions
ConditionsYield
With TEA In tetrahydrofuran for 1h; Heating;98%
In chloroform
2,6-Diaminotoluene
823-40-5

2,6-Diaminotoluene

2,5-hexanedione
110-13-4

2,5-hexanedione

2,6-di(2,5-dimethyl-1H-pyrrol-1-yl)toluene

2,6-di(2,5-dimethyl-1H-pyrrol-1-yl)toluene

Conditions
ConditionsYield
montmorillonite K-10 at 90℃; for 0.05h; modified Paal-Knorr synthesis; microwave heating;97%
2,6-Diaminotoluene
823-40-5

2,6-Diaminotoluene

dimethyl acetylenedicarboxylate
762-42-5

dimethyl acetylenedicarboxylate

2,6-bis(1,2-dicarbomethoxyvinylamino)toluene
49635-43-0

2,6-bis(1,2-dicarbomethoxyvinylamino)toluene

Conditions
ConditionsYield
In methanol; chloroform standing overnight;95%
In methanol at 0 - 20℃;
2,6-Diaminotoluene
823-40-5

2,6-Diaminotoluene

dimethyl acetylenedicarboxylate
762-42-5

dimethyl acetylenedicarboxylate

C19H22N2O8

C19H22N2O8

Conditions
ConditionsYield
In methanol; chloroform at 0 - 20℃; for 16h; Inert atmosphere; Schlenk technique;95%
2,6-Diaminotoluene
823-40-5

2,6-Diaminotoluene

4-formylphenyl 4-(dodecyloxy)benzoate
56800-36-3

4-formylphenyl 4-(dodecyloxy)benzoate

N,N'-bis[4-(4-n-dodecyloxybenzoyloxy)benzylidene]-(2-methyl-1,3-phenylene)diamine
1373878-22-8

N,N'-bis[4-(4-n-dodecyloxybenzoyloxy)benzylidene]-(2-methyl-1,3-phenylene)diamine

Conditions
ConditionsYield
With acetic acid In ethanol at 20℃; for 24h;93%
2,6-Diaminotoluene
823-40-5

2,6-Diaminotoluene

2-ethoxymethylene-3-oxobutanoic acid ethyl ester
3788-94-1

2-ethoxymethylene-3-oxobutanoic acid ethyl ester

C21H26N2O6

C21H26N2O6

Conditions
ConditionsYield
In ethanol at 70℃; for 0.333333h; Microwave irradiation; Inert atmosphere;93%
diisobutyl carbonate
539-92-4

diisobutyl carbonate

2,6-Diaminotoluene
823-40-5

2,6-Diaminotoluene

2,4-TDA
1187831-01-1

2,4-TDA

Conditions
ConditionsYield
With sodium isobutoxide at 120℃; for 0.5h; Inert atmosphere;92%
2,6-Diaminotoluene
823-40-5

2,6-Diaminotoluene

2-methyl-1,3-diaminocyclohexane

2-methyl-1,3-diaminocyclohexane

Conditions
ConditionsYield
With palladium on activated charcoal; hydrogen; sodium sulfate In 1,4-dioxane at 220℃; under 105011 Torr; for 6h; Solvent; Pressure; Temperature; Reagent/catalyst; Autoclave;91%
Hydrogenation;
With 5 wt% ruthenium/carbon; hydrogen; sodium nitrite In isopropyl alcohol at 170℃; under 62256.2 Torr; for 4h; Temperature; Autoclave;
2,6-Diaminotoluene
823-40-5

2,6-Diaminotoluene

Ethyl oxalyl chloride
4755-77-5

Ethyl oxalyl chloride

diethyl N,N'-[1,3-(2-methyl)phenyl]dioxalamate
47300-42-5

diethyl N,N'-[1,3-(2-methyl)phenyl]dioxalamate

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran for 1h; Reflux;90%
With triethylamine In N,N-dimethyl-formamide
2,6-Diaminotoluene
823-40-5

2,6-Diaminotoluene

diethyl 2-ethoxymethylenemalonate
87-13-8

diethyl 2-ethoxymethylenemalonate

diethyl 2-{[3-(2,2-bisethoxycarbonylvinylamino)-2-methylphenylamino]methylene}malonate
39595-13-6

diethyl 2-{[3-(2,2-bisethoxycarbonylvinylamino)-2-methylphenylamino]methylene}malonate

Conditions
ConditionsYield
In ethanol for 5h; Heating;90%
2,6-Diaminotoluene
823-40-5

2,6-Diaminotoluene

trifluoroacetic anhydride
407-25-0

trifluoroacetic anhydride

N-[3-(2,2-dimethylpropionylamino)-2-methylphenyl]-2,2-dimethylpropionamide
25116-07-8

N-[3-(2,2-dimethylpropionylamino)-2-methylphenyl]-2,2-dimethylpropionamide

Conditions
ConditionsYield
In tetrahydrofuran Cooling with ice;90%
dipropyl acetylenedicarboxylate
14447-02-0

dipropyl acetylenedicarboxylate

2,6-Diaminotoluene
823-40-5

2,6-Diaminotoluene

C27H38N2O8

C27H38N2O8

Conditions
ConditionsYield
In methanol; chloroform at 0 - 20℃; for 16h; Schlenk technique; Inert atmosphere;90%
2,6-Diaminotoluene
823-40-5

2,6-Diaminotoluene

C28H50O4

C28H50O4

C63H110N2O8

C63H110N2O8

Conditions
ConditionsYield
In methanol; chloroform at 0 - 20℃; for 16h; Schlenk technique; Inert atmosphere;88%
2,6-Diaminotoluene
823-40-5

2,6-Diaminotoluene

acetylenedicarboxylic acid di-n-hexyl ester

acetylenedicarboxylic acid di-n-hexyl ester

C39H62N2O8

C39H62N2O8

Conditions
ConditionsYield
In methanol; chloroform at 0 - 20℃; for 16h; Schlenk technique; Inert atmosphere;86%
2,6-Diaminotoluene
823-40-5

2,6-Diaminotoluene

ethyl acetoacetate
141-97-9

ethyl acetoacetate

(Z)-3-[3-((Z)-2-Ethoxycarbonyl-1-methyl-vinylamino)-2-methyl-phenylamino]-but-2-enoic acid ethyl ester
182410-18-0

(Z)-3-[3-((Z)-2-Ethoxycarbonyl-1-methyl-vinylamino)-2-methyl-phenylamino]-but-2-enoic acid ethyl ester

Conditions
ConditionsYield
With calcium sulfate; acetic acid In ethanol at 80℃; for 2h;85%
With copper(II) sulfate In ethanol at 80℃; for 4h;
methanol
67-56-1

methanol

2,6-Diaminotoluene
823-40-5

2,6-Diaminotoluene

N2,N2,N6,N6-tetrakis(methoxymethyl)-2,6-diaminotoluene

N2,N2,N6,N6-tetrakis(methoxymethyl)-2,6-diaminotoluene

Conditions
ConditionsYield
With oxygen at 120℃; under 7500.75 Torr; for 10h; Reagent/catalyst; Autoclave;85%
2,6-Diaminotoluene
823-40-5

2,6-Diaminotoluene

pivaloyl chloride
3282-30-2

pivaloyl chloride

N-[3-(2,2-dimethylpropionylamino)-2-methylphenyl]-2,2-dimethylpropionamide
25116-07-8

N-[3-(2,2-dimethylpropionylamino)-2-methylphenyl]-2,2-dimethylpropionamide

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran for 0.5h;84%
With pyridine
With triethylamine
1-bromo-4-tert-butylbenzene
3972-65-4

1-bromo-4-tert-butylbenzene

2,6-Diaminotoluene
823-40-5

2,6-Diaminotoluene

N1,N3-bis(4-tert-butylphenyl)-2-methylbenzene-1,3-diamine

N1,N3-bis(4-tert-butylphenyl)-2-methylbenzene-1,3-diamine

Conditions
ConditionsYield
With chloro[(tri-tert-butylphosphine)-2-(2-aminobiphenyl)]palladium (II); sodium t-butanolate In toluene at 90℃; for 12h; Inert atmosphere;81%
2,6-Diaminotoluene
823-40-5

2,6-Diaminotoluene

propynoic acid ethyl ester
623-47-2

propynoic acid ethyl ester

2,6-bis(2'-carboethoxyvinylamino)toluene

2,6-bis(2'-carboethoxyvinylamino)toluene

Conditions
ConditionsYield
In methanol for 24h; Ambient temperature;80%
2,6-Diaminotoluene
823-40-5

2,6-Diaminotoluene

indole-2,3-dione
91-56-5

indole-2,3-dione

3,3'-[(2-methyl-1,3-phenylene)dinitrilo]bis[1,3-dihydro-2H-indole-2-one]

3,3'-[(2-methyl-1,3-phenylene)dinitrilo]bis[1,3-dihydro-2H-indole-2-one]

Conditions
ConditionsYield
With acetic acid In ethanol for 19h; Heating;80%
2,6-Diaminotoluene
823-40-5

2,6-Diaminotoluene

4-chloro-6,7-dimethoxyquinoline-3-carbonitrile
214470-55-0

4-chloro-6,7-dimethoxyquinoline-3-carbonitrile

10,11-dimethoxy-4-methyldibenzo[c,f]-2,7-naphthyridine-3,6-diamine
936833-38-4

10,11-dimethoxy-4-methyldibenzo[c,f]-2,7-naphthyridine-3,6-diamine

Conditions
ConditionsYield
With pyridine hydrochloride In 2-ethoxy-ethanol at 210℃; under 1034.32 Torr; for 1h; Product distribution / selectivity; Microwave irradiation;80%
With pyridine hydrochloride In 2-ethoxy-ethanol at 130℃; for 8h; Product distribution / selectivity;65%
In 2-ethoxy-ethanol for 15h; Heating;
2,6-Diaminotoluene
823-40-5

2,6-Diaminotoluene

4-chloro-6,7-dimethoxyquinoline-3-carbonitrile
214470-55-0

4-chloro-6,7-dimethoxyquinoline-3-carbonitrile

A

10,11-dimethoxy-4-methyldibenzo[c,f]-2,7-naphthyridine-3,6-diamine
936833-38-4

10,11-dimethoxy-4-methyldibenzo[c,f]-2,7-naphthyridine-3,6-diamine

B

4-[(3-amino-2-methylphenyl)amino]-6,7-dimethoxyquinoline-3-carbonitrile

4-[(3-amino-2-methylphenyl)amino]-6,7-dimethoxyquinoline-3-carbonitrile

Conditions
ConditionsYield
With pyridine hydrochloride In 2-ethoxy-ethanol at 210℃; for 1h; Temperature; Time; Concentration; Microwave irradiation;A 79%
B n/a
2,6-Diaminotoluene
823-40-5

2,6-Diaminotoluene

2-dimethylaminomethylene-1,3-bis(dimethylimmonio)propane bistetrafluoroborate

2-dimethylaminomethylene-1,3-bis(dimethylimmonio)propane bistetrafluoroborate

7-amino-8-methylquinoline-3-carboxaldehyde
521074-55-5

7-amino-8-methylquinoline-3-carboxaldehyde

Conditions
ConditionsYield
Stage #1: 2,6-toluenediamine; 2-dimethylaminomethylene-1,3-bis(dimethylimmonio)propane bistetrafluoroborate In isopropyl alcohol for 16h; Reflux;
Stage #2: With hydrogenchloride In water at 20 - 70℃; for 5h;
Stage #3: With potassium carbonate In water; ethyl acetate at 90℃; for 16h;
77%
Stage #1: 2,6-toluenediamine; 2-dimethylaminomethylene-1,3-bis(dimethylimmonio)propane bistetrafluoroborate In isopropyl alcohol for 16h; Heating / reflux;
Stage #2: With hydrogenchloride; water In isopropyl alcohol at 70℃; for 5h;
Stage #3: With potassium carbonate In water; ethyl acetate at 90℃;
2,6-Diaminotoluene
823-40-5

2,6-Diaminotoluene

acetylenedicarboxylic acid diethyl ester
762-21-0

acetylenedicarboxylic acid diethyl ester

C23H30N2O8

C23H30N2O8

Conditions
ConditionsYield
In methanol; chloroform at 0 - 20℃; for 16h; Schlenk technique; Inert atmosphere;77%
2-methylphenyl bromide
95-46-5

2-methylphenyl bromide

2,6-Diaminotoluene
823-40-5

2,6-Diaminotoluene

2-methyl-N1,N3-di-o-tolylbenzene-1,3-diamine

2-methyl-N1,N3-di-o-tolylbenzene-1,3-diamine

Conditions
ConditionsYield
With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate In 1,4-dioxane at 110℃; Inert atmosphere;76.06%
2,6-Diaminotoluene
823-40-5

2,6-Diaminotoluene

4-formyl-3-hydroxyphenyl 4-n-dodecyloxy-3-fluorobenzoate
1363404-49-2

4-formyl-3-hydroxyphenyl 4-n-dodecyloxy-3-fluorobenzoate

N,N'-bis[4-(4-n-dodecyloxy-3-fluorobenzoyloxy)-2-hydroxybenzylidene]-(2-methyl-1,3-phenylene)diamine
1373878-32-0

N,N'-bis[4-(4-n-dodecyloxy-3-fluorobenzoyloxy)-2-hydroxybenzylidene]-(2-methyl-1,3-phenylene)diamine

Conditions
ConditionsYield
With acetic acid In ethanol at 20℃; for 24h;76%

823-40-5Relevant articles and documents

Sustainable and recyclable palladium nanoparticles–catalyzed reduction of nitroaromatics in water/glycerol at room temperature

Chen, Jin,Dai, Bencai,Liu, Changchun,Shen, Zhihao,Zhao, Yongde,Zhou, Yang

, p. 540 - 544 (2020/07/14)

Palladium nanoparticles with unique catalytic activity and high stability are synthesized. These nanoparticles exhibit excellent catalytic reduction activity for nitroaromatics in green solvents in the presence of H2 at ambient pressure and temperature. The prominent advantages of this nanotechnology include low consumption of catalyst, excellent chemoselectivity, high reusability of the catalyst, and environmentally green solvents.

Pd-Pt/modified GO as an efficient and selective heterogeneous catalyst for the reduction of nitroaromatic compounds to amino aromatic compounds by the hydrogen source

Salahshournia, Hossein,Ghiaci, Mehran

, (2019/02/14)

In this work, different nitroaromatic compounds were successfully reduced to their corresponding aromatic amines with excellent conversion and selectivity in methanol at 50?°C by using Pd-Pt nanoparticles immobilized on the modified grapheme oxide (m-GO) and hydrogen as the reducing source. The catalytic efficiency of Pd and Pd-Pt loading on the modified GO was investigated for the reduction of various nitroaromatic compounds, and the Pd-Pt/m-GO system demonstrated the highest conversion and selectivity. The catalyst was characterized by different techniques including FT-IR, Raman, UV–Vis, XRD, BET, XPS, FESEM, EDS, and TEM. The metal nanoparticles with the size of less than 10?nm were uniformly distributed on the m-GO. The catalyst could be reused at least five times without losing activity, showing the stability of the catalyst structure. Finally, the efficiency of the prepared catalyst was compared with Pd-Pt/AC, and Pd-Pt/GO catalysts.

Co-MOF-Derived Hierarchical Mesoporous Yolk-shell-structured Nanoreactor for the Catalytic Reduction of Nitroarenes with Hydrazine Hydrate

Yuan, Man,Zhang, Hongbo,Yang, Chen,Wang, Fanhao,Dong, Zhengping

, p. 3327 - 3338 (2019/07/04)

Porous nanoreactors demonstrate immense potential for applications in heterogeneous catalysis due to their excellent mass-transfer performance and stability. The design of a simple, universal strategy for fabricating nanoreactor catalysts is of significance for organic transformation. In this study, a nanoreactor with a hierarchical mesoporous yolk-shell structure was successfully prepared by the high-temperature carbonization of a ZIF-67@polymer composite. The core of the resultant Co@ZDC@mC material comprised Co NPs anchored in the ZIF-67-derived carbon framework, while the shell comprised resin-polymer-derived mesoporous carbon. The as-obtained Co@ZDC@mC-700 catalyst enriched reactants, efficiently catalyzed the reaction in the core, and permitted the desorption of the product from the nanoreactor. In the catalytic reduction of nitrobenzene with N2H4?H2O, Co@ZDC@mC-700 exhibited superior catalytic efficiency (TOF=1136.3 h?1). In addition, Co@ZDC@mC-700 exhibited excellent performance for the catalytic reduction of various functionalized nitroarenes, as well as good reusability and recyclability. Hence, a simple, useful approach for fabricating a metal-organic-framework-derived non-noble metal-based yolk-shell nanoreactor for effective catalytic transformation is proposed.

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