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N,N-Diphenyl-p-phenylenediamine

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Name

N,N-Diphenyl-p-phenylenediamine

EINECS 200-806-4
CAS No. 2350-01-8 Density 1.168 g/cm3
PSA 29.26000 LogP 5.31980
Solubility N/A Melting Point 144.0 to 148.0 °C
Formula C18H16N2 Boiling Point 436.9 °C at 760 mmHg
Molecular Weight 260.338 Flash Point 193.3 °C
Transport Information N/A Appearance N/A
Safety Risk Codes N/A
Molecular Structure Molecular Structure of 2350-01-8 (N,N-Diphenyl-p-phenylenediamine) Hazard Symbols N/A
Synonyms

1,4-Benzenediamine,N,N-diphenyl- (9CI);p-Phenylenediamine, N,N-diphenyl- (7CI,8CI);4-(Diphenylamino)aniline;4-(N,N-Diphenylamino)aniline;4-Aminotriphenylamine;N,N-Diphenyl-1,4-phenylenediamine;N,N-Diphenyl-4-aminoaniline;N-(4-Aminophenyl)-N,N-diphenylamine;NSC231610;p-(Diphenylamino)aniline;p-Aminotriphenylamine;N,N-diphenylbenzene-1,4-diamine;

Article Data 47

N,N-Diphenyl-p-phenylenediamine Synthetic route

4316-57-8

4-nitrophenyldiphenylamine

2350-01-8

4-aminotriphenylamine

Conditions
ConditionsYield
With tin; acetic acid98%
With tin; acetic acid98%
With palladium 10% on activated carbon; hydrogen In tetrahydrofuran under 3000.3 Torr; for 3h;96%
144393-34-0

4-bromo-N-(4-bromophenyl)-N-(4-nitrophenyl)amine

A

1-N,1-N-bis(4-bromophenyl)benzene-1,4-diamine

B

4-amino-3,4',4''-tribromotriphenylamine

C

2350-01-8

4-aminotriphenylamine

Conditions
ConditionsYield
Stage #1: 4-nitrophenyl-bis(4'-bromophenyl)amine With tin; acetic acid at 75℃; for 1h;
Stage #2: at 65℃; for 9h;
A 87%
B 12%
C 1%
36809-26-4

4-N,N-diphenylamino-1-bromobenzene

2350-01-8

4-aminotriphenylamine

Conditions
ConditionsYield
With tri-tert-butyl phosphine; lithium hexamethyldisilazane; bis(dibenzylideneacetone)-palladium(0) In toluene at 20℃; for 20h;77%
Stage #1: 4-N,N-diphenylamino-1-bromobenzene With tri-tert-butyl phosphine; lithium hexamethyldisilazane; bis(dibenzylideneacetone)-palladium(0) In toluene at 20℃; for 4h; Inert atmosphere;
Stage #2: With trifluoroacetic acid
74%
With copper(l) iodide; ammonia; caesium carbonate In water; N,N-dimethyl-formamide; acetylacetone at 100℃; for 12h;
Multi-step reaction with 2 steps
1: sodium t-butanolate; bis(dibenzylideneacetone)-palladium(0); (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / toluene / 20 h / 95 °C / Inert atmosphere
2: hydrogenchloride / tetrahydrofuran; water / 0.5 h / 20 °C
View Scheme
4316-56-7

(p-chlorophenyl)diphenylamine

2350-01-8

4-aminotriphenylamine

Conditions
ConditionsYield
With bis[chloro(1,2,3-trihapto-allylbenzene)palladium(II)]; N-[2-(di(1-adamantyl)phosphino)phenyl]morpholine; ammonia; sodium t-butanolate In 1,4-dioxane at 65℃; for 24h; Inert atmosphere; chemoselective reaction;68%
122-39-4

diphenylamine

106-40-1

4-bromo-aniline

2350-01-8

4-aminotriphenylamine

Conditions
ConditionsYield
With water; sodium t-butanolate In N,N-dimethyl-formamide at 120℃; for 10h; Schlenk technique;55%
606-88-2

N,N,N'-triphenylhydrazine

2350-01-8

4-aminotriphenylamine

Conditions
ConditionsYield
With hydrogenchloride; tin(ll) chloride
7647-01-0

hydrogenchloride

4316-57-8

4-nitrophenyldiphenylamine

tin

tin

2350-01-8

4-aminotriphenylamine

64-17-5

ethanol

4316-57-8

4-nitrophenyldiphenylamine

64-19-7

acetic acid

zinc

zinc

2350-01-8

4-aminotriphenylamine

144393-34-0

4-bromo-N-(4-bromophenyl)-N-(4-nitrophenyl)amine

A

4-amino-4'-bromotriphenylamine

B

4-amino-3,4'-dibromotriphenylamine

C

4-amino-3,4',4''-tribromotriphenylamine

D

2350-01-8

4-aminotriphenylamine

Conditions
ConditionsYield
With tin; acetic acid for 8h; Heating; Further byproducts given;A 6 % Chromat.
B 13 % Chromat.
C 32 % Chromat.
D 4 % Chromat.
122-39-4

diphenylamine

2350-01-8

4-aminotriphenylamine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: NaH / dimethylformamide
2: hydrazine / Pd/C / ethanol / Heating
View Scheme
Multi-step reaction with 2 steps
1: K2CO3 / dimethylsulfoxide / 10 h / 145 - 150 °C
2: Sn; aq. HCl / ethanol / Heating
View Scheme
Multi-step reaction with 2 steps
1: K2CO3; copper; nitrobenzene
2: zinc; alcohol; glacial acetic acid / unter Kuehlung
View Scheme

N,N-Diphenyl-p-phenylenediamine Specification

The 1,4-Benzenediamine,N1,N1-diphenyl-, with the CAS registry number 2350-01-8, has the systematic name of N,N-diphenylbenzene-1,4-diamine. It is also called ,N-Diphenyl-p-phenylenediamine. And the molecular formula of this chemical is C18H16N2.

The physical properties of 1,4-Benzenediamine,N1,N1-diphenyl- are as following: (1)ACD/LogP: 4.16; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 3.98; (4)ACD/LogD (pH 7.4): 4.16; (5)ACD/BCF (pH 5.5): 567.46; (6)ACD/BCF (pH 7.4): 845.91; (7)ACD/KOC (pH 5.5): 2902.79; (8)ACD/KOC (pH 7.4): 4327.18; (9)#H bond acceptors: 2; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 4; (12)Polar Surface Area: 6.48 Å2; (13)Index of Refraction: 1.681; (14)Molar Refractivity: 84.33 cm3; (15)Molar Volume: 222.8 cm3; (16)Polarizability: 33.43×10-24cm3; (17)Surface Tension: 53.9 dyne/cm; (18)Density: 1.168 g/cm3; (19)Flash Point: 193.3 °C; (20)Enthalpy of Vaporization: 69.35 kJ/mol; (21)Boiling Point: 436.9 °C at 760 mmHg; (22)Vapour Pressure: 7.78E-08 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES: c3c(N(c1ccccc1)c2ccc(cc2)N)cccc3
(2)InChI: InChI=1/C18H16N2/c19-15-11-13-18(14-12-15)20(16-7-3-1-4-8-16)17-9-5-2-6-10-17/h1-14H,19H2
(3)InChIKey: UXKQNCDDHDBAPD-UHFFFAOYAQ

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