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65181-78-4

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Basic Information
CAS No.: 65181-78-4
Name: N,N'-Bis(3-methylphenyl)-N,N'-bis(phenyl)benzidine
Article Data: 33
Molecular Structure:
Molecular Structure of 65181-78-4 (N,N'-Bis(3-methylphenyl)-N,N'-bis(phenyl)benzidine)
Formula: C38H32N2
Molecular Weight: 516.685
Synonyms: [1,1'-Biphenyl]-4,4'-diamine,N,N'-bis(3-methylphenyl)-N,N'-diphenyl- (9CI);4,4'-Bis[N-(3-methylphenyl)-N-phenylamino]biphenyl;ELA 4021;N,N'-Bis(3-methylphenyl)-N,N'-diphenylbenzidine;N,N'-Diphenyl-N,N-bis(3-methylphenyl)-1,1'-biphenyl-4,4'-diamine;N,N'-Diphenyl-N,N'-bis(3-methylphenyl)-p-benzidine;N,N'-Diphenyl-N,N'-bis(3-methylphenyl)[1,1'-biphenyl]-4,4'-diamine;N,N'-Diphenyl-N,N'-bis(3-methylphenyl)benzidine;N,N'-Diphenyl-N,N'-bis(m-tolyl)[1,1'-biphenyl]-4,4'-diamine;N,N'-Diphenyl-N,N'-di(3-methylphenyl)-4,4'-diaminobiphenyl;N,N'-Diphenyl-N,N'-di(3-methylphenyl)benzidine;N,N'-Diphenyl-N,N'-di-m-tolylbiphenyl-4,4'-diamine;
EINECS: 413-810-8
Density: 1.149 g/cm3
Melting Point: 169 °C
Boiling Point: 680.1 °C at 760 mmHg
Flash Point: 303.1 °C
Solubility: Insoluble in water
Appearance: solid
Hazard Symbols: DangerousN
Risk Codes: 36/37/38-51/53
Safety: 26-36/37/39-61
PSA: 6.48000
LogP: 10.91000
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Synthetic route
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meta-bromotoluene

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chlorobenzene

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p,p'-diaminobiphenyl

65181-78-4

4,4'-bis(m-tolylphenylamino)biphenyl

Conditions
ConditionsYield
With chloro[2-(dicyclohexylphosphino)-3 ,6-dimethoxy-2’,4’, 6’-triisopropyl- 1,1’-biphenyl] [2-(2-aminoethyl)phenyl]palladium(II); sodium t-butanolate; ruphos In 1,4-dioxane at 110℃; for 24h; Inert atmosphere;98%
...Expand

C40H32N2O4

65181-78-4

4,4'-bis(m-tolylphenylamino)biphenyl

Conditions
ConditionsYield
With copper(I) oxide; N,N,N,N,-tetramethylethylenediamine at 200℃; for 4h; Temperature; Large scale;93.5%
92-86-4

4-(4-bromophenyl)bromobenzene

1205-64-7

3-Methyldiphenylamine

65181-78-4

4,4'-bis(m-tolylphenylamino)biphenyl

Conditions
ConditionsYield
With palladium diacetate; tri-tert-butyl phosphine; sodium t-butanolate In o-xylene at 120℃; for 3h;91%
Stage #1: 3-Methyldiphenylamine With n-butyllithium
Stage #2: 4-(4-bromophenyl)bromobenzene With bis[tris(2-methylphenyl)phosphine]palladium In toluene at 100℃;		87%
With sodium t-butanolate; palladium diacetate; 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride In toluene at 20 - 130℃; Inert atmosphere;85.2%
3001-15-8

4,4'-diiodobiphenyl

1205-64-7

3-Methyldiphenylamine

65181-78-4

4,4'-bis(m-tolylphenylamino)biphenyl

Conditions
ConditionsYield
With potassium hydroxide; 1,10-Phenanthroline; copper(l) chloride In toluene at 125℃; for 5h; Ullmann condensation;85%
With copper; potassium carbonate; PEG-6000 In 1,2-dichloro-benzene for 22h; Heating / reflux;
CT-73; mixture of

CT-73; mixture of

65181-78-4

4,4'-bis(m-tolylphenylamino)biphenyl

Conditions
ConditionsYield
In n-heptane Purification / work up;84.4%
3001-15-8

4,4'-diiodobiphenyl

1205-64-7

3-Methyldiphenylamine

620-84-8

4-methyldiphenylamine

A

20441-06-9

N,N'-di(4''-methylphenyl)-N,N'-diphenyl-1,1'-biphenyl-4,4'-diamine

B

65181-78-4

4,4'-bis(m-tolylphenylamino)biphenyl

C

N,N'-diphenyl-N,N'-bis(3-methylphenyl)-[1,1-biphenyl]-4,4'-diamine

Conditions
ConditionsYield
With copper; potassium carbonate; polyethylene glycol at 90 - 205℃; for 17h; Heating / reflux;
Stage #1: 4,4'-diiodobiphenyl; 3-Methyldiphenylamine; 4-methyldiphenylamine With copper; PEG-6000 at 100℃; Neat (no solvent);
Stage #2: With potassium carbonate at 205℃; for 14h; Neat (no solvent);
...Expand
3001-15-8

4,4'-diiodobiphenyl

92115-21-4

N-methyl-N-phenyl-3-toluidine

65181-78-4

4,4'-bis(m-tolylphenylamino)biphenyl

Conditions
ConditionsYield
With copper; potassium carbonate; polyethylene glycol In 1,2-dichloro-benzene for 22h; Heating / reflux;
92-86-4

4-(4-bromophenyl)bromobenzene

1205-64-7

3-Methyldiphenylamine

122-39-4

diphenylamine

A

N,N,N'-tris-(phenyl)-N'-(m-tolyl)-benzidine

B

15546-43-7

N,N,N',N'-tetraphenyl-4,4'-diaminobiphenyl

C

65181-78-4

4,4'-bis(m-tolylphenylamino)biphenyl

Conditions
ConditionsYield
With potassium hydroxide; copper In Soltrol/70 at 165℃; for 7h; Product distribution / selectivity;
tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl at 139℃; for 6.5h; Product distribution / selectivity;
With calcium carbonate; zinc; 1,10-Phenanthroline; copper diacetate In xylene at 120℃; for 10.5h; Product distribution / selectivity;
...Expand
3001-15-8

4,4'-diiodobiphenyl

1205-64-7

3-Methyldiphenylamine

12775-96-1, 15158-11-9, 15721-63-8, 16941-75-6, 17493-86-6, 19498-52-3, 20499-83-6, 20499-84-7, 20499-85-8, 20499-86-9, 20573-10-8, 20573-11-9, 21595-51-7, 21595-52-8, 22206-52-6, 26445-28-3, 28959-95-7, 37362-93-9, 39417-05-5, 54603-16-6, 54603-23-5, 54603-32-6, 54603-40-6, 54603-48-4, 54603-81-5, 54603-89-3, 56316-56-4, 95985-91-4, 122297-32-9, 7440-50-8

copper

65181-78-4

4,4'-bis(m-tolylphenylamino)biphenyl

Conditions
ConditionsYield
With potassium hydroxide
...Expand
118-91-2

ortho-chlorobenzoic acid

65181-78-4

4,4'-bis(m-tolylphenylamino)biphenyl

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: caesium carbonate; copper; copper(II) oxide / water / 105 °C / Large scale
2: caesium carbonate; copper; copper(II) oxide / nitrobenzene / 3 h / 200 °C / Large scale
3: copper(I) oxide; N,N,N,N,-tetramethylethylenediamine / 4 h / 200 °C / Large scale
View Scheme
Raw Materials
591-17-3
3001-15-8
92-87-5
625-95-6
1205-64-7
92-86-4
531-91-9
108-90-7
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Chemistry

IUPAC: N-(3-Methylphenyl)-4-[4-(3-methyl-N-phenylanilino)phenyl]-N-phenylaniline
The Molecular Structure of (1,1'-Biphenyl)-4,4'-diamine, N4,N4'-bis(3-methylphenyl)-N4,N4'-diphenyl- (CAS NO.65181-78-4):
         
Molecular Formula: C38H32N2
Molecular Weight: 516.674080 g/mol
Stability: Stable. Incompatible with strong oxidizing agents. 
Nominal Mass: 516 Da
Average Mass: 516.6741 Da
Monoisotopic Mass: 516.256549 Da 
EINECS: 413-810-8
Index of Refraction: 1.671
Molar Refractivity: 168.18 cm3
Molar Volume: 449.5 cm3
Density: 1.149 g/cm3
Flash Point: 303.1 °C
Melting Point: 169 °C
Surface Tension: 50.3 dyne/cm
Enthalpy of Vaporization: 99.81 kJ/mol
Boiling Point: 680.1 °C at 760 mmHg
Vapour Pressure: 2.35E-18 mmHg at 25 °C 
Appearance of (1,1'-Biphenyl)-4,4'-diamine, N4,N4'-bis(3-methylphenyl)-N4,N4'-diphenyl- (CAS NO.65181-78-4): solid
Product Categories of (1,1'-Biphenyl)-4,4'-diamine, N4,N4'-bis(3-methylphenyl)-N4,N4'-diphenyl- (CAS NO.65181-78-4): electronic; pharmacetical; Biphenyl & Diphenyl ether; Electronic Chemicals; Electroluminescence; Functional Materials; Highly Purified Reagents; Other Categories; Refined Products by Sublimation; White powder 
Canonical SMILES: CC1=CC(=CC=C1)N(C2=CC=CC=C2)C3=CC=C(C=C3)C4=CC=C(C=C4)N(C5=CC=CC=C5)C6=CC=CC(=C6)C
InChI: InChI=1S/C38H32N2/c1-29-11-9-17-37(27-29)39(33-13-5-3-6-14-33)35-23-19-31(20-24-35)32-21-25-36(26-22-32)40(34-15-7-4-8-16-34)38-18-10-12-30(2)28-38/h3-28H,1-2H3
InChIKey: OGGKVJMNFFSDEV-UHFFFAOYSA-N

Safety Profile

Hazard Codes: DangerousN
Risk Statements: 36/37/38-51/53 
R36/37/38:Irritating to eyes, respiratory system and skin
R51/53:Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment
Safety Statements: 26-36/37/39-61 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection
S61:Avoid release to the environment. Refer to special instructions / safety data sheets
RIDADR: 3077

Specification

 (1,1'-Biphenyl)-4,4'-diamine, N4,N4'-bis(3-methylphenyl)-N4,N4'-diphenyl- (CAS NO.65181-78-4) is also called as N,N'-Bis(3-methylphenyl)-N,N'-diphenyl-(1,1'-biphenyl)-4,4'-diamine .