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74-31-7

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74-31-7 Usage

Description

N,N'-Diphenyl-4-phenylenediamine (DPPD) is a rubber accelerant, formerly contained in the "black rubber mix". The most frequent occupational categories are in metal industry, homemakers, health services and laboratories, and building industries.

Chemical Properties

grey powder

Uses

Different sources of media describe the Uses of 74-31-7 differently. You can refer to the following data:
1. Polymerization inhibitor. Antioxidant for rubber, petroleum oils, feedstuffs.
2. N1,N4-Diphenylbenzene-1,4-diamine can be used to prepare low pressure change, high temperature resistant flame retardant silicone rubber.
3. N,N'-Diphenyl-4-phenylene diamine is an antioxidant for rubber, petroleum oils, and feed stuffs; stabilizer; a polymerization inhibitor; used to retard copper degradation; as an intermediate for dyes, drugs, plasties and detergents; antidegradant for nitrile-butadiene rubber, natural, styrene-butadiene, isoprene, butadiene, and ehloroprene rubbers.

Definition

ChEBI: An N-substituted diamine that is 1,4-phenylenediamine in which one hydrogen from each amino group is replaced by a phenyl group.

General Description

Gray or dark gray powder or flakes.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

N,N-Diphenyl-p-phenylenediamine may react with oxidizing materials . 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

N,N-Diphenyl-p-phenylenediamine is combustible. N,N-Diphenyl-p-phenylenediamine may form explosive dust-air mixtures.

Contact allergens

A rubber accelerant, formerly contained in “blackrubber mix.” The most frequent occupational categories are in the metal industry, homemakers, health services and laboratories, and the building industry.

Purification Methods

Crystallise the diamine from EtOH, chlorobenzene/pet ether or *benzene. It has also been crystallised from aniline, then extracted three times with absolute EtOH. [Beilstein 13 H 80.]

Check Digit Verification of cas no

The CAS Registry Mumber 74-31-7 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 7 and 4 respectively; the second part has 2 digits, 3 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 74-31:
(4*7)+(3*4)+(2*3)+(1*1)=47
47 % 10 = 7
So 74-31-7 is a valid CAS Registry Number.
InChI:InChI=1/C18H16N2/c1-3-7-15(8-4-1)19-17-11-13-18(14-12-17)20-16-9-5-2-6-10-16/h1-14,19-20H

74-31-7 Well-known Company Product Price

  • Brand
  • (Code)Product description
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  • Price
  • Detail
  • Alfa Aesar

  • (B23713)  N,N'-Diphenyl-p-phenylenediamine, 97%   

  • 74-31-7

  • 5g

  • 298.0CNY

  • Detail
  • Alfa Aesar

  • (B23713)  N,N'-Diphenyl-p-phenylenediamine, 97%   

  • 74-31-7

  • 25g

  • 907.0CNY

  • Detail
  • Alfa Aesar

  • (B23713)  N,N'-Diphenyl-p-phenylenediamine, 97%   

  • 74-31-7

  • 100g

  • 2315.0CNY

  • Detail
  • Aldrich

  • (292265)  N,N′-Diphenyl-p-phenylenediamine  98%

  • 74-31-7

  • 292265-5G

  • 405.99CNY

  • Detail
  • Aldrich

  • (292265)  N,N′-Diphenyl-p-phenylenediamine  98%

  • 74-31-7

  • 292265-25G

  • 1,037.79CNY

  • Detail

74-31-7SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 16, 2017

Revision Date: Aug 16, 2017

1.Identification

1.1 GHS Product identifier

Product name N,N'-diphenyl-1,4-phenylenediamine

1.2 Other means of identification

Product number -
Other names 1,4-Benzenediamine, N,N‘-diphenyl-

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Fillers
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:74-31-7 SDS

74-31-7Synthetic route

chlorobenzene
108-90-7

chlorobenzene

N-phenylphenylene-1,4-diamine
101-54-2

N-phenylphenylene-1,4-diamine

N,N'-diphenyl-1,4-phenylenediamine
74-31-7

N,N'-diphenyl-1,4-phenylenediamine

Conditions
ConditionsYield
With dicyclohexyl-(2′,4′,6′-triisopropyl-3,6-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine; chloro[2-(dicyclohexylphosphino)-3,6-dimethoxy-2’,4’,6’-triisopropyl-1,1’-biphenyl] [2-(2-aminoethyl)phenyl]palladium(II); sodium t-butanolate In 1,4-dioxane at 80℃; for 2h; Inert atmosphere; chemoselective reaction;99%
With 5-(di-tert-butylphosphino)-1′, 3′, 5′-triphenyl-1′H-[1,4′]bipyrazole; bis[chloro(1,2,3-trihapto-allylbenzene)palladium(II)]; sodium t-butanolate In toluene at 110℃; for 12h; Buchwald-Hartwig Coupling; Inert atmosphere; Glovebox; chemoselective reaction;87%
dimethanesulfonate hydroquinone
126150-65-0

dimethanesulfonate hydroquinone

aniline
62-53-3

aniline

N,N'-diphenyl-1,4-phenylenediamine
74-31-7

N,N'-diphenyl-1,4-phenylenediamine

Conditions
ConditionsYield
With potassium phosphate; bis[chloro(1,2,3-trihapto-allylbenzene)palladium(II)]; N-[2-(di(1-adamantyl)phosphino)phenyl]morpholine In 1,4-dioxane; tert-butyl alcohol at 110℃; Buchwald-Hartwig Coupling; Inert atmosphere; Glovebox; chemoselective reaction;98%
N4-(2-methylphenyl) benzene-1,4-diamine
66311-46-4

N4-(2-methylphenyl) benzene-1,4-diamine

N-phenylphenylene-1,4-diamine
101-54-2

N-phenylphenylene-1,4-diamine

phenol
108-95-2

phenol

A

N,N'-diphenyl-1,4-phenylenediamine
74-31-7

N,N'-diphenyl-1,4-phenylenediamine

B

N-phenyl-N'-tolyl-p-phenylenediamine
27173-16-6

N-phenyl-N'-tolyl-p-phenylenediamine

Conditions
ConditionsYield
With 5%-palladium/activated carbon In cyclohexanone at 250℃; for 6h; Autoclave; Inert atmosphere;A 94.4%
B 88.8%
N-phenylphenylene-1,4-diamine
101-54-2

N-phenylphenylene-1,4-diamine

phenol
108-95-2

phenol

N,N'-diphenyl-1,4-phenylenediamine
74-31-7

N,N'-diphenyl-1,4-phenylenediamine

Conditions
ConditionsYield
With 5%-palladium/activated carbon In cyclohexanone at 220℃; for 6h; Concentration; Autoclave; Inert atmosphere;93.6%
chlorobenzene
108-90-7

chlorobenzene

1,4-phenylenediamine
106-50-3

1,4-phenylenediamine

N,N'-diphenyl-1,4-phenylenediamine
74-31-7

N,N'-diphenyl-1,4-phenylenediamine

Conditions
ConditionsYield
With sodium t-butanolate; Ni(0)*2IPr In 1,4-dioxane at 100℃;92%
1.4-dibromobenzene
106-37-6

1.4-dibromobenzene

aniline
62-53-3

aniline

N,N'-diphenyl-1,4-phenylenediamine
74-31-7

N,N'-diphenyl-1,4-phenylenediamine

Conditions
ConditionsYield
With potassium hydroxide In N,N-dimethyl-formamide at 130℃; for 0.55h; Buchwald-Hartwig Coupling;91%
With 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; tris(dibenzylideneacetone)dipalladium (0)
bromochlorobenzene
106-39-8

bromochlorobenzene

aniline
62-53-3

aniline

N,N'-diphenyl-1,4-phenylenediamine
74-31-7

N,N'-diphenyl-1,4-phenylenediamine

Conditions
ConditionsYield
With dicyclohexyl(2-methoxy-6-methylbiphenyl-2,-yl)phosphine; potassium tert-butylate; palladium diacetate In 1,4-dioxane at 160℃; for 0.5h; Inert atmosphere; Microwave irradiation;86%
N,N' diphenyl-1,4 benzoquinone diimine

N,N' diphenyl-1,4 benzoquinone diimine

malononitrile
109-77-3

malononitrile

A

2-(2,5-bis(phenylamino)phenyl)malononitrile
1200190-23-3

2-(2,5-bis(phenylamino)phenyl)malononitrile

B

N,N'-diphenyl-1,4-phenylenediamine
74-31-7

N,N'-diphenyl-1,4-phenylenediamine

Conditions
ConditionsYield
Stage #1: malononitrile With tetrabutyl ammonium fluoride In water; acetonitrile at 20℃; Michael addition reaction; Inert atmosphere;
Stage #2: N,N' diphenyl-1,4 benzoquinone diimine In water; acetonitrile at 20 - 70℃; Michael addition reaction; Inert atmosphere;
A 80%
B n/a
N,N' diphenyl-1,4 benzoquinone diimine

N,N' diphenyl-1,4 benzoquinone diimine

ethyl 2-cyanoacetate
105-56-6

ethyl 2-cyanoacetate

A

ethyl 2-(2,5-bis(phenylamino)phenyl)-2-cyanoacetate
1200190-29-9

ethyl 2-(2,5-bis(phenylamino)phenyl)-2-cyanoacetate

B

N,N'-diphenyl-1,4-phenylenediamine
74-31-7

N,N'-diphenyl-1,4-phenylenediamine

Conditions
ConditionsYield
Stage #1: ethyl 2-cyanoacetate With tetrabutyl ammonium fluoride In water; acetonitrile at 20℃; Michael addition reaction; Inert atmosphere;
Stage #2: N,N' diphenyl-1,4 benzoquinone diimine In water; acetonitrile at 20 - 70℃; Michael addition reaction; Inert atmosphere;
A 77%
B n/a
N,N' diphenyl-1,4 benzoquinone diimine

N,N' diphenyl-1,4 benzoquinone diimine

methyl 2-cyanoacetate
105-34-0

methyl 2-cyanoacetate

A

methyl 2-(2,5-bis(phenylamino)phenyl)-2-cyanoacetate
1200190-26-6

methyl 2-(2,5-bis(phenylamino)phenyl)-2-cyanoacetate

B

N,N'-diphenyl-1,4-phenylenediamine
74-31-7

N,N'-diphenyl-1,4-phenylenediamine

Conditions
ConditionsYield
Stage #1: methyl 2-cyanoacetate With tetrabutyl ammonium fluoride In water; acetonitrile at 20℃; Michael addition reaction; Inert atmosphere;
Stage #2: N,N' diphenyl-1,4 benzoquinone diimine In water; acetonitrile at 20 - 70℃; Michael addition reaction; Inert atmosphere;
A 76%
B n/a
1-butanethiol
109-79-5

1-butanethiol

N,N'-diphenyl-1,4-phenylenediamine
6246-98-6, 73334-88-0, 73334-89-1

N,N'-diphenyl-1,4-phenylenediamine

A

C22H24N2S
911110-01-5

C22H24N2S

B

C26H32N2S2
911110-02-6

C26H32N2S2

C

N,N'-diphenyl-1,4-phenylenediamine
74-31-7

N,N'-diphenyl-1,4-phenylenediamine

Conditions
ConditionsYield
In tetrahydrofuran at 20℃; for 6h;A 74%
B 10%
C 11%
N,N' diphenyl-1,4 benzoquinone diimine

N,N' diphenyl-1,4 benzoquinone diimine

acetylacetone
123-54-6

acetylacetone

A

3-(2,5-bis(phenylamino)phenyl)pentane-2,4-dione
1200190-20-0

3-(2,5-bis(phenylamino)phenyl)pentane-2,4-dione

B

N,N'-diphenyl-1,4-phenylenediamine
74-31-7

N,N'-diphenyl-1,4-phenylenediamine

Conditions
ConditionsYield
Stage #1: acetylacetone With tetrabutyl ammonium fluoride In water; acetonitrile at 20℃; Michael addition reaction; Inert atmosphere;
Stage #2: N,N' diphenyl-1,4 benzoquinone diimine In water; acetonitrile at 20 - 70℃; Michael addition reaction; Inert atmosphere;
A 74%
B n/a
N,N' diphenyl-1,4 benzoquinone diimine

N,N' diphenyl-1,4 benzoquinone diimine

cyanoacetic acid tert-butyl ester
1116-98-9

cyanoacetic acid tert-butyl ester

A

t-butyl 2-(2,5-bis(phenylamino)phenyl)-2-cyanoacetate
1200190-32-4

t-butyl 2-(2,5-bis(phenylamino)phenyl)-2-cyanoacetate

B

N,N'-diphenyl-1,4-phenylenediamine
74-31-7

N,N'-diphenyl-1,4-phenylenediamine

Conditions
ConditionsYield
Stage #1: cyanoacetic acid tert-butyl ester With tetrabutyl ammonium fluoride In water; acetonitrile at 20℃; Michael addition reaction; Inert atmosphere;
Stage #2: N,N' diphenyl-1,4 benzoquinone diimine In water; acetonitrile at 20 - 70℃; Michael addition reaction; Inert atmosphere;
A 73%
B n/a
N,N' diphenyl-1,4 benzoquinone diimine

N,N' diphenyl-1,4 benzoquinone diimine

nitromethane
75-52-5

nitromethane

A

2-(nitromethyl)-N,N'-diphenyl-1,4-phenylenediamine
1200190-10-8

2-(nitromethyl)-N,N'-diphenyl-1,4-phenylenediamine

B

N,N'-diphenyl-1,4-phenylenediamine
74-31-7

N,N'-diphenyl-1,4-phenylenediamine

Conditions
ConditionsYield
Stage #1: nitromethane With tetrabutyl ammonium fluoride In water; acetonitrile at 20℃; Michael addition reaction; Inert atmosphere;
Stage #2: N,N' diphenyl-1,4 benzoquinone diimine In water; acetonitrile at 20 - 70℃; Michael addition reaction; Inert atmosphere;
A 72%
B 20%
N,N' diphenyl-1,4 benzoquinone diimine

N,N' diphenyl-1,4 benzoquinone diimine

Nitroethane
79-24-3

Nitroethane

A

2-(1-nitroethyl)-N1,N4-diphenylbenzene-1,4-diamine
1200190-13-1

2-(1-nitroethyl)-N1,N4-diphenylbenzene-1,4-diamine

B

N,N'-diphenyl-1,4-phenylenediamine
74-31-7

N,N'-diphenyl-1,4-phenylenediamine

Conditions
ConditionsYield
Stage #1: Nitroethane With tetrabutyl ammonium fluoride In water; acetonitrile at 20℃; Michael addition reaction; Inert atmosphere;
Stage #2: N,N' diphenyl-1,4 benzoquinone diimine In water; acetonitrile at 20 - 70℃; Michael addition reaction; Inert atmosphere;
A 70%
B n/a
N,N' diphenyl-1,4 benzoquinone diimine

N,N' diphenyl-1,4 benzoquinone diimine

2-nitropropane
79-46-9

2-nitropropane

A

N1,N4-diphenyl-2-(prop-1-en-2-yl)benzene-1,4-diamine
1200190-17-5

N1,N4-diphenyl-2-(prop-1-en-2-yl)benzene-1,4-diamine

B

N,N'-diphenyl-1,4-phenylenediamine
74-31-7

N,N'-diphenyl-1,4-phenylenediamine

Conditions
ConditionsYield
Stage #1: 2-nitropropane With tetrabutyl ammonium fluoride In water; acetonitrile at 20℃; Michael addition reaction; Inert atmosphere;
Stage #2: N,N' diphenyl-1,4 benzoquinone diimine In water; acetonitrile at 20 - 70℃; Michael addition reaction; Inert atmosphere;
A 68%
B n/a
bromobenzene
108-86-1

bromobenzene

N-phenylphenylene-1,4-diamine
101-54-2

N-phenylphenylene-1,4-diamine

N,N'-diphenyl-1,4-phenylenediamine
74-31-7

N,N'-diphenyl-1,4-phenylenediamine

Conditions
ConditionsYield
With 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate; bis(dibenzylideneacetone)-palladium(0) In toluene at 100℃;67%
1,4-cyclohexanedione-2,5-dicarboxylic acid
490-93-7

1,4-cyclohexanedione-2,5-dicarboxylic acid

aniline
62-53-3

aniline

N,N'-diphenyl-1,4-phenylenediamine
74-31-7

N,N'-diphenyl-1,4-phenylenediamine

Conditions
ConditionsYield
In various solvent(s) at 73℃; for 150h;53%
N-phenylphenylene-1,4-diamine
101-54-2

N-phenylphenylene-1,4-diamine

N,N'-diphenyl-1,4-phenylenediamine
74-31-7

N,N'-diphenyl-1,4-phenylenediamine

Conditions
ConditionsYield
palladium In 5,5-dimethyl-1,3-cyclohexadiene; cyclohexanone; nitrobenzene40%
cyclohexanone
108-94-1

cyclohexanone

4-nitro-aniline
100-01-6

4-nitro-aniline

A

4-ntrophenyl(phenyl)amine
836-30-6

4-ntrophenyl(phenyl)amine

B

N,N'-diphenyl-1,4-phenylenediamine
74-31-7

N,N'-diphenyl-1,4-phenylenediamine

Conditions
ConditionsYield
With styrene; 10 wt% Pd(OH)2 on carbon In 1,4-dioxane at 150℃; under 3750.38 Torr; for 12h; Flow reactor;A 29%
B 6%
N,N'-diphenyl-1,4-phenylenediamine
6246-98-6, 73334-88-0, 73334-89-1

N,N'-diphenyl-1,4-phenylenediamine

N,N'-diphenyl-1,4-phenylenediamine
74-31-7

N,N'-diphenyl-1,4-phenylenediamine

Conditions
ConditionsYield
With zinc
4-amino-phenol
123-30-8

4-amino-phenol

aniline
62-53-3

aniline

N,N'-diphenyl-1,4-phenylenediamine
74-31-7

N,N'-diphenyl-1,4-phenylenediamine

Conditions
ConditionsYield
With hydrogenchloride at 300℃;
With ammonium chloride at 300℃;
1.4-dibromobenzene
106-37-6

1.4-dibromobenzene

anthranilic acid
118-92-3

anthranilic acid

N,N'-diphenyl-1,4-phenylenediamine
74-31-7

N,N'-diphenyl-1,4-phenylenediamine

N,N'-diphenyl-1,4-phenylenediamine
6246-98-6, 73334-88-0, 73334-89-1

N,N'-diphenyl-1,4-phenylenediamine

aniline
62-53-3

aniline

A

N,N'-diphenyl-1,4-phenylenediamine
74-31-7

N,N'-diphenyl-1,4-phenylenediamine

B

azophenin
4435-12-5

azophenin

p-aminophenol hydrochloride
51-78-5

p-aminophenol hydrochloride

aniline
62-53-3

aniline

N,N'-diphenyl-1,4-phenylenediamine
74-31-7

N,N'-diphenyl-1,4-phenylenediamine

Conditions
ConditionsYield
at 220℃; unter Druck;
aniline
62-53-3

aniline

hydroquinone
123-31-9

hydroquinone

N,N'-diphenyl-1,4-phenylenediamine
74-31-7

N,N'-diphenyl-1,4-phenylenediamine

Conditions
ConditionsYield
With sodium hydrogen sulfate at 200℃;
With hydrogenchloride at 300℃;
With phosphoric acid at 260℃;
aniline
62-53-3

aniline

1,4-phenylenediamine
106-50-3

1,4-phenylenediamine

N,N'-diphenyl-1,4-phenylenediamine
74-31-7

N,N'-diphenyl-1,4-phenylenediamine

Conditions
ConditionsYield
With hydrogenchloride at 290℃;
ethanol
64-17-5

ethanol

N,N'-diphenyl-1,4-phenylenediamine
6246-98-6, 73334-88-0, 73334-89-1

N,N'-diphenyl-1,4-phenylenediamine

hydroquinone
123-31-9

hydroquinone

A

N,N'-diphenyl-1,4-phenylenediamine
74-31-7

N,N'-diphenyl-1,4-phenylenediamine

B

quinhydrone
106-34-3

quinhydrone

p-nitrosodiphenylamine
156-10-5

p-nitrosodiphenylamine

phenylhydrazine
100-63-0

phenylhydrazine

N,N'-diphenyl-1,4-phenylenediamine
74-31-7

N,N'-diphenyl-1,4-phenylenediamine

Conditions
ConditionsYield
With ethanol
2,2,4-trimethyl-6-hydroxy-1,2-dihydroquinoline
72107-05-2

2,2,4-trimethyl-6-hydroxy-1,2-dihydroquinoline

N,N'-diphenyl-1,4-phenylenediamine
6246-98-6, 73334-88-0, 73334-89-1

N,N'-diphenyl-1,4-phenylenediamine

A

2,2,4-trimethyl-6-oxo-2,6-dihydroquinoline
4071-18-5

2,2,4-trimethyl-6-oxo-2,6-dihydroquinoline

B

N,N'-diphenyl-1,4-phenylenediamine
74-31-7

N,N'-diphenyl-1,4-phenylenediamine

Conditions
ConditionsYield
In chlorobenzene at 23℃; Rate constant; Kinetics; other temps.;
N,N'-diphenyl-1,4-phenylenediamine
74-31-7

N,N'-diphenyl-1,4-phenylenediamine

acetic anhydride
108-24-7

acetic anhydride

N1-[4-methyl(phenyl)carboxamidophenyl]-N1-phenylacetamide
113510-51-3

N1-[4-methyl(phenyl)carboxamidophenyl]-N1-phenylacetamide

Conditions
ConditionsYield
With sodium acetate100%
With sodium acetate at 120 - 130℃; for 3h;97%
N,N'-diphenyl-1,4-phenylenediamine
74-31-7

N,N'-diphenyl-1,4-phenylenediamine

A

N,N'-diphenyl-1,4-phenylenediamine
6246-98-6, 73334-88-0, 73334-89-1

N,N'-diphenyl-1,4-phenylenediamine

B

benzene-1,2-dicarboxylic acid
88-99-3

benzene-1,2-dicarboxylic acid

Conditions
ConditionsYield
With monoperoxyphthalic acid In tetrahydrofuran at 25℃;A 88%
B 98%
N,N'-diphenyl-1,4-phenylenediamine
74-31-7

N,N'-diphenyl-1,4-phenylenediamine

dibutoxyphenylborane
7330-48-5

dibutoxyphenylborane

A

BN(C6H5)C6H4N(C6H5)

BN(C6H5)C6H4N(C6H5)

B

butan-1-ol
71-36-3

butan-1-ol

Conditions
ConditionsYield
In xylene at reflux 140-106°C for 165 h, then distilling butanol-borane azeotrop;A 98%
B n/a
formaldehyd
50-00-0

formaldehyd

N,N'-diphenyl-1,4-phenylenediamine
74-31-7

N,N'-diphenyl-1,4-phenylenediamine

N,N'-dimethyl-N,N'-diphenyl-1,4-phenylenediamine
17754-68-6

N,N'-dimethyl-N,N'-diphenyl-1,4-phenylenediamine

Conditions
ConditionsYield
With NaBH4CN; acetic acid at 20℃; for 2.5h; Methylation; reduction;97%
N,N'-diphenyl-1,4-phenylenediamine
74-31-7

N,N'-diphenyl-1,4-phenylenediamine

<1,4>benzothiazino<2,3-b>phenothiazine
111385-12-7

<1,4>benzothiazino<2,3-b>phenothiazine

Conditions
ConditionsYield
With iodine; sulfur at 180℃; for 24h;95%
Stage #1: N,N'-diphenyl-1,4-phenylenediamine With iodine; sulfur at 180 - 200℃; Inert atmosphere;
Stage #2: With sodium sulfide for 2h; Reflux;
64.3%
With iodine; sulfur
With hydrogen sulfide; iodine; sulfur; phenylhydrazine 1.) o-dichlorobenzene, reflux, 24 h 2.) 150 deg C; Yield given. Multistep reaction;
N,N'-diphenyl-1,4-phenylenediamine
74-31-7

N,N'-diphenyl-1,4-phenylenediamine

N,N'-dinitroso-N,N'-diphenyl-p-phenylenediamine
2716-09-8

N,N'-dinitroso-N,N'-diphenyl-p-phenylenediamine

Conditions
ConditionsYield
With trichloromelamine; silica gel; sodium nitrite In dichloromethane; water at 20℃; for 0.416667h;95%
4-bromobenzenecarbonitrile
623-00-7

4-bromobenzenecarbonitrile

N,N'-diphenyl-1,4-phenylenediamine
74-31-7

N,N'-diphenyl-1,4-phenylenediamine

C32H22N4

C32H22N4

Conditions
ConditionsYield
With potassium tert-butylate; tri tert-butylphosphoniumtetrafluoroborate In toluene at 120℃; Buchwald-Hartwig Coupling; Inert atmosphere; Sealed tube;95%
2-Picolinic acid
98-98-6

2-Picolinic acid

copper(ll) sulfate pentahydrate

copper(ll) sulfate pentahydrate

Terpinolene
586-62-9

Terpinolene

3-Iodotoluene
625-95-6

3-Iodotoluene

N,N'-diphenyl-1,4-phenylenediamine
74-31-7

N,N'-diphenyl-1,4-phenylenediamine

N,N'-diphenyl-N,N'-bis(3-methylphenyl)-1,4-phenylenediamine

N,N'-diphenyl-N,N'-bis(3-methylphenyl)-1,4-phenylenediamine

Conditions
ConditionsYield
With potassium carbonate In nitrogen; water; ethyl acetate; toluene94.9%
N,N'-diphenyl-1,4-phenylenediamine
74-31-7

N,N'-diphenyl-1,4-phenylenediamine

methyl iodide
74-88-4

methyl iodide

N,N'-dimethyl-N,N'-diphenyl-1,4-phenylenediamine
17754-68-6

N,N'-dimethyl-N,N'-diphenyl-1,4-phenylenediamine

Conditions
ConditionsYield
Stage #1: N,N'-diphenyl-1,4-phenylenediamine With methyllithium at -78℃;
Stage #2: methyl iodide at -60℃;
94%
N,N'-diphenyl-1,4-phenylenediamine
74-31-7

N,N'-diphenyl-1,4-phenylenediamine

potassium acrylate
10192-85-5

potassium acrylate

N-neopentyl-4-(4-methylpiperidinyl)-pyridinium chloride
95758-27-3

N-neopentyl-4-(4-methylpiperidinyl)-pyridinium chloride

3-Chloropropyltrimethoxysilan
2530-87-2

3-Chloropropyltrimethoxysilan

3-(trimethoxysilyl)propyl acrylate
4369-14-6

3-(trimethoxysilyl)propyl acrylate

Conditions
ConditionsYield
In methanol92.7%
1-(2'-ethylhexyl)-4-dimethylaminopyridinium chloride
109911-78-6

1-(2'-ethylhexyl)-4-dimethylaminopyridinium chloride

N,N'-diphenyl-1,4-phenylenediamine
74-31-7

N,N'-diphenyl-1,4-phenylenediamine

sodium methacrylate
5536-61-8

sodium methacrylate

3-Chloropropyltrimethoxysilan
2530-87-2

3-Chloropropyltrimethoxysilan

γ-methacryl-oxypropyl-trimethoxysilane
7727-32-4

γ-methacryl-oxypropyl-trimethoxysilane

Conditions
ConditionsYield
90.3%
N,N'-diphenyl-1,4-phenylenediamine
74-31-7

N,N'-diphenyl-1,4-phenylenediamine

4-N,N-diphenylamino-1-bromobenzene
36809-26-4

4-N,N-diphenylamino-1-bromobenzene

1-N,1-N,4-N-triphenyl-4-N-[4-(N-[4-(N-phenylanilino)phenyl]anilino)phenyl]benzene-1,4-diamine
141546-10-3

1-N,1-N,4-N-triphenyl-4-N-[4-(N-[4-(N-phenylanilino)phenyl]anilino)phenyl]benzene-1,4-diamine

Conditions
ConditionsYield
With tri-tert-butyl phosphine; potassium tert-butylate; palladium diacetate In toluene at 110℃; for 12h; Ullmann Condensation;87.9%
N,N'-diphenyl-1,4-phenylenediamine
74-31-7

N,N'-diphenyl-1,4-phenylenediamine

N,N’-diphenyl-p-benzoquinonediimine

N,N’-diphenyl-p-benzoquinonediimine

Conditions
ConditionsYield
With 1,4-diaza-bicyclo[2.2.2]octane; copper diacetate In dichloromethane at 20℃; for 7h;87%
With lead dioxide
With 4-(phenylimino)cyclohexa-2,5-dienone In chlorobenzene at 68.45℃; Equilibrium constant; Thermodynamic data; Further Variations:; Temperatures;
1-bromo-4-octylbenzene
51554-93-9

1-bromo-4-octylbenzene

N,N'-diphenyl-1,4-phenylenediamine
74-31-7

N,N'-diphenyl-1,4-phenylenediamine

bis-N,N'-(4-octylphenyl)-bis-N,N'-phenyl-1,4-phenylenediamine
1257423-28-1

bis-N,N'-(4-octylphenyl)-bis-N,N'-phenyl-1,4-phenylenediamine

Conditions
ConditionsYield
With tri-tert-butyl phosphine; palladium diacetate; sodium t-butanolate In toluene at 120℃; for 48h; Inert atmosphere;86%
N,N'-diphenyl-1,4-phenylenediamine
74-31-7

N,N'-diphenyl-1,4-phenylenediamine

isopropenylbenzene
98-83-9

isopropenylbenzene

phenylenediamine derivative

phenylenediamine derivative

Conditions
ConditionsYield
sulfuric acid Product distribution / selectivity;85%
3,3-Dimethylglutaric acid
4839-46-7

3,3-Dimethylglutaric acid

N,N'-diphenyl-1,4-phenylenediamine
74-31-7

N,N'-diphenyl-1,4-phenylenediamine

C25H20N2

C25H20N2

Conditions
ConditionsYield
With zinc(II) chloride for 0.0833333h; microwave irradiation;84%
1,5-pentanedioic acid
110-94-1

1,5-pentanedioic acid

N,N'-diphenyl-1,4-phenylenediamine
74-31-7

N,N'-diphenyl-1,4-phenylenediamine

C23H16N2

C23H16N2

Conditions
ConditionsYield
With zinc(II) chloride for 0.0833333h; microwave irradiation;83%
2,6-dimethyl-1-chlorobenzene
6781-98-2

2,6-dimethyl-1-chlorobenzene

N,N'-diphenyl-1,4-phenylenediamine
74-31-7

N,N'-diphenyl-1,4-phenylenediamine

N,N'-bis(1,3-dimethylphenyl)-N,N'-diphenyl-1,4-phenylenediamine

N,N'-bis(1,3-dimethylphenyl)-N,N'-diphenyl-1,4-phenylenediamine

Conditions
ConditionsYield
With bis(di-tert-butyl(2-butenyl)phosphine)dichloropalladium; sodium t-butanolate In o-xylene at 130 - 135℃; for 6h; Reagent/catalyst; Inert atmosphere;82%
N,N'-diphenyl-1,4-phenylenediamine
74-31-7

N,N'-diphenyl-1,4-phenylenediamine

phenylpropynoic acid methyl ester
4891-38-7

phenylpropynoic acid methyl ester

1,2-diphenyl-6-phenylamino-quinolin-4(1H)-one

1,2-diphenyl-6-phenylamino-quinolin-4(1H)-one

Conditions
ConditionsYield
With trifluorormethanesulfonic acid; copper(II) bis(trifluoromethanesulfonate) In 1,2-dichloro-ethane at 120℃; for 12h; regioselective reaction;82%
N,N'-diphenyl-1,4-phenylenediamine
74-31-7

N,N'-diphenyl-1,4-phenylenediamine

1-bromo-4-(2-(2-methoxyethoxy)ethoxy)benzene
112968-89-5

1-bromo-4-(2-(2-methoxyethoxy)ethoxy)benzene

C40H44N2O6

C40H44N2O6

Conditions
ConditionsYield
With tris-(dibenzylideneacetone)dipalladium(0); tributylphosphine; sodium t-butanolate In toluene for 5h; Buchwald-Hartwig Coupling; Inert atmosphere; Schlenk technique; Reflux;81%
N,N'-diphenyl-1,4-phenylenediamine
74-31-7

N,N'-diphenyl-1,4-phenylenediamine

1,4-Cyclohexanedione
637-88-7

1,4-Cyclohexanedione

N,N,N',N'-tetraphenyl-p-phenylenediamine
14118-16-2

N,N,N',N'-tetraphenyl-p-phenylenediamine

Conditions
ConditionsYield
toluene-4-sulfonic acid In toluene for 12h; Heating;80%
N,N'-diphenyl-1,4-phenylenediamine
74-31-7

N,N'-diphenyl-1,4-phenylenediamine

phenylacetyl chloride
103-80-0

phenylacetyl chloride

N,N'-diphenyl-N,N'-bis(2-phenacetyl)phenylene-1,4-diamine
351424-85-6

N,N'-diphenyl-N,N'-bis(2-phenacetyl)phenylene-1,4-diamine

Conditions
ConditionsYield
With pyridine In chloroform at 20℃; for 5h; Cooling with ice;80%
In 1,4-dioxane Heating;61%
N,N'-diphenyl-1,4-phenylenediamine
74-31-7

N,N'-diphenyl-1,4-phenylenediamine

A

C18H15N3O

C18H15N3O

B

N,N'-dinitroso-N,N'-diphenyl-p-phenylenediamine
2716-09-8

N,N'-dinitroso-N,N'-diphenyl-p-phenylenediamine

Conditions
ConditionsYield
With trichloromelamine; silica gel; sodium nitrite In dichloromethane; water at 20℃; for 0.5h;A 20%
B 80%

74-31-7Relevant articles and documents

Formation and photophysics of a stable concave-convex supramolecular complex of C60 and a substituted s-triazine derivative

Schuster, David I.,Rosenthal, Joel,MacMahon, Shaun,Jarowski, Peter D.,Alabi, Christopher A.,Guldi, Dirk M.

, p. 2538 - 2539 (2002)

Spectroscopic, electrochemical and computational data (show that C60 and a highly phenylated s-triazine derivative form a stable supramolecular complex at micromolar concentrations in solution at ambient temperatures, due to strong van der Waals attraction between their complementary surfaces.

Continuous Synthesis of Aryl Amines from Phenols Utilizing Integrated Packed-Bed Flow Systems

Ichitsuka, Tomohiro,Kobayashi, Shū,Koumura, Nagatoshi,Sato, Kazuhiko,Takahashi, Ikko

, p. 15891 - 15896 (2020/07/13)

Aryl amines are important pharmaceutical intermediates among other numerous applications. Herein, an environmentally benign route and novel approach to aryl amine synthesis using dehydrative amination of phenols with amines and styrene under continuous-flow conditions was developed. Inexpensive and readily available phenols were efficiently converted into the corresponding aryl amines, with small amounts of easily removable co-products (i.e., H2O and alkanes), in multistep continuous-flow reactors in the presence of heterogeneous Pd catalysts. The high product selectivity and functional-group tolerance of this method allowed aryl amines with diverse functional groups to be selectively obtained in high yields over a continuous operation time of one week.

Design, preparation and characterization of aerogel NiO-CuO-CoO/SiO2 nanocomposite as a reusable catalyst for C-N cross-coupling reaction

Ghasemi, Amir Hossein,Naeimi, Hossein

supporting information, p. 5056 - 5063 (2020/04/09)

Aerogels are porous, non-crystalline solid materials with high specific surface space, plentiful three-dimensional (3D) porous construction, ultra-low density and significant porosity. The aerogel nanocomposite is produced using sol-gel and supercritical drying processes. CO2 supercritical drying (SCD) is the most powerful process, ensuring optimal product properties such as high porosity, low density, and high thermal conductivity. On this account, we used the CO2 supercritical drying method to produce NiO-CuO-CoO/SiO2 nanocomposite aerogels and applied it as a reusable catalyst for the C-N cross-coupling reaction (Buchwald-Hartwig amination). Powerful catalytic activity for the C-N cross-coupling reaction was obtained for the new nanocomposite aerogel, that is, NiO-CuO-CoO/SiO2. The catalyst was characterized by X-ray Powder Diffraction (XRD), field emission scanning electron microscopy (FE-SEM), energy-dispersive X-ray spectroscopy (EDS), elemental mapping and Brunauer-Emmett-Teller (BET). Also, organic compounds were identified by melting point, Fourier-transform infrared spectroscopy (FT-IR) and hydrogen-1 nuclear magnetic resonance (1H NMR) analyses.

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