4,4''-Diamino-p-terphenyl supplier

Name
4,4''-DIAMINO-P-TERPHENYL
EINECS 677-188-1
CAS No. 3365-85-3
Article Data18
CAS DataBase
Density 1.159 g/cm³
Solubility
Melting Point 242-244 °C
Formula C₁₈H₁₆N₂
Boiling Point 484.2 °C at 760 mmHg
Molecular Weight 260.338
Flash Point 296.3 °C
Transport Information
Appearance
Safety 45-53
Risk Codes 20/21/22-45
Molecular Structure
Hazard Symbols
Synonyms [p-Terphenyl]-4,4''-diamine(7CI,8CI);p-Terphenyl-4',4''-diamine (6CI);1,4-Bis(4-aminophenyl)benzene;4,4'-p-Phenylenedianiline;4,4''-Diamino-p-terphenyl;4,4''-p-Terphenyldiamine;p,p''-Diamino-p-terphenyl;p-Terphenylenediamine;
PSA 52.04000
LogP 5.34740

Synthetic route

: 3282-11-9
p,p-dinitro-p-terphenyl

: 3365-85-3
4,4''-diamino-p-terphenyl

Conditions

Conditions	Yield
With palladium 10% on activated carbon; hydrazine In ethanol for 6h; Inert atmosphere; Reflux;	100%
With hydrogen; palladium on activated charcoal In tetrahydrofuran for 18h;	99%
With 3% Pd/C; hydrazine In ethanol Heating;	77%

: 106-37-6
1.4-dibromobenzene

: 214360-73-3
4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)aniline

: 3365-85-3
4,4''-diamino-p-terphenyl

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In water; toluene for 24h; Schlenk technique; Inert atmosphere; Heating;	52%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In water; toluene for 24h; Schlenk technique; Inert atmosphere; Heating;	52%
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,4-dioxane; water at 110℃; for 48h; Inert atmosphere;	48%

: 4612-26-4
1,4-Phenyldiboronic acid

: 3365-85-3
4,4''-diamino-p-terphenyl

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 76 percent / K2CO3 / tetrakis(triphenylphosphine)palladium(0) / tetrahydrofuran / 18 h / Heating 2: 99 percent / H2 / Pd/C / tetrahydrofuran / 18 h View Scheme

: 586-78-7
para-nitrophenyl bromide

: 3365-85-3
4,4''-diamino-p-terphenyl

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 76 percent / K2CO3 / tetrakis(triphenylphosphine)palladium(0) / tetrahydrofuran / 18 h / Heating 2: 99 percent / H2 / Pd/C / tetrahydrofuran / 18 h View Scheme

: 92-94-4
[1,1';4',1'']terphenyl

: 3365-85-3
4,4''-diamino-p-terphenyl

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: fuming HNO3 / acetic acid 2: SnCl2, aq. HCl View Scheme
Multi-step reaction with 2 steps 1: HNO3 / acetic acid 2: H2, Py / Raney-Ni / 100 °C / 60800 - 65360 Torr View Scheme

: 99-65-0
meta-dinitrobenzene

: 3365-85-3
4,4''-diamino-p-terphenyl

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: N-Bromosuccinimide; sulfuric acid / 60 °C 2: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / tetrahydrofuran / 48 h / Reflux; Inert atmosphere 3: palladium 10% on activated carbon; hydrazine / ethanol / 6 h / Inert atmosphere; Reflux View Scheme

: 18242-39-2
3,5-dinitrobromobenzene

: 3365-85-3
4,4''-diamino-p-terphenyl

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / tetrahydrofuran / 48 h / Reflux; Inert atmosphere 2: palladium 10% on activated carbon; hydrazine / ethanol / 6 h / Inert atmosphere; Reflux View Scheme

: 106-40-1
4-bromo-aniline

: 3365-85-3
4,4''-diamino-p-terphenyl

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: triethylamine; bis-triphenylphosphine-palladium(II) chloride / 1,4-dioxane / 12 h / 120 °C / Schlenk technique; Inert atmosphere 2: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / water; toluene / 24 h / Schlenk technique; Inert atmosphere; Heating View Scheme
Multi-step reaction with 2 steps 1: bis-triphenylphosphine-palladium(II) chloride; triethylamine / 1,4-dioxane / 12 h / 120 °C / Schlenk technique; Inert atmosphere 2: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / water; toluene / 24 h / Schlenk technique; Inert atmosphere; Heating View Scheme

: 106-37-6
1.4-dibromobenzene

: 3365-85-3
4,4''-diamino-p-terphenyl

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: bis(dibenzylideneacetone)-palladium(0); tricyclohexylphosphine; potassium acetate / 1,4-dioxane / Heating 2: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran; water / Heating 3: hydrazine; 3% Pd/C / ethanol / Heating View Scheme
Multi-step reaction with 3 steps 1.1: potassium acetate; bis(dibenzylideneacetone)-palladium(0); tricyclohexylphosphine / 1,4-dioxane / 4.33 h / 110 °C 2.1: potassium carbonate / tetrahydrofuran; water / 0.33 h / 100 °C 2.2: 5 h / 100 °C 3.1: hydrazine; 3% Pd/C / ethanol / 12 h / 100 °C View Scheme

: 99770-93-1
benzene-1,4-diboronic acid bispinacol ester

: 3365-85-3
4,4''-diamino-p-terphenyl

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: potassium carbonate / tetrahydrofuran; water / 0.33 h / 100 °C 1.2: 5 h / 100 °C 2.1: hydrazine; 3% Pd/C / ethanol / 12 h / 100 °C View Scheme

: 3365-85-3
4,4''-diamino-p-terphenyl

: 708-06-5
2-hydroxynaphthalene-1-carbaldehyde

: 1236010-45-9
1,1'-[(4,4''-p-terphenylene)bis(iminomethyl)]bis(2-naphthol)

Conditions

Conditions	Yield
With formic acid In methanol; dichloromethane Reflux;	98%

: 3972-65-4
1-bromo-4-tert-butylbenzene

: 3365-85-3
4,4''-diamino-p-terphenyl

: N4,N4,N4″,N4″-tetrakis(4-(tert-butyl)phenyl)-[1,1′:4′,1″-terphenyl]-4,4″-diamine

Conditions

Conditions	Yield
With tri-tert-butyl phosphine; potassium tert-butylate; bis(dibenzylideneacetone)-palladium(0) In toluene at 80℃; for 69.5h; Inert atmosphere;	97%

: 37942-07-7
3,5-di-tert-butyl-2-hydroxybenzaldehyde

: 3365-85-3
4,4''-diamino-p-terphenyl

: 6,6'-[(4,4"-p-terphenylene)bis(iminomethyl)]bis(2,4-di-tert-butylphenol)

Conditions

Conditions	Yield
With formic acid In methanol; dichloromethane Reflux;	93%

: 24623-65-2
3-tert-butyl-2-hydroxybenzaldehyde

: 3365-85-3
4,4''-diamino-p-terphenyl

: 6,6'-[(4,4"-p-terphenylene)bis(iminomethyl)]bis(2-tert-butylphenol)

Conditions

Conditions	Yield
With formic acid In methanol; dichloromethane Reflux;	91%

: 3365-85-3
4,4''-diamino-p-terphenyl

: 16182-04-0
Ethoxycarbonyl isothiocyanate

: 916653-34-4
4,4''-bis(N'-ethoxycarbonylthiourea)-[1,1';4',1'']terphenyl

Conditions

Conditions	Yield
In dichloromethane at 20℃; for 24h;	89%

: 3365-85-3
4,4''-diamino-p-terphenyl

: 916653-34-4
4,4''-bis(N'-ethoxycarbonylthiourea)-[1,1';4',1'']terphenyl

Conditions

Conditions	Yield
With Ethoxycarbonyl isothiocyanate In dichloromethane at 20℃; for 24h;	89%

: 3365-85-3
4,4''-diamino-p-terphenyl

: 90-02-8
salicylaldehyde

: 2,2'-[(4,4"-p-terphenylene)bis(iminomethyl)]-diphenol

Conditions

Conditions	Yield
With formic acid In methanol; dichloromethane Reflux;	84%

: 108-86-1
bromobenzene

: 3365-85-3
4,4''-diamino-p-terphenyl

: N4,N4”-diphenylamine[1,1':4',1”-terphenyl]-4,4”-diamine

Conditions

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate In toluene for 5h; Inert atmosphere; Reflux;	83.6%

: 3365-85-3
4,4''-diamino-p-terphenyl

: 322474-21-5
N,N'-bis-Boc-S-methyl-isothiourea

: 4,4''-bis-(N',N''-t-butoxycarbonyl)guanidino-[1,1';4',1'']terphenyl

Conditions

Conditions	Yield
With triethylamine; mercury dichloride In N,N-dimethyl-formamide at 20℃; for 24h;	79%
With triethylamine; mercury dichloride In N,N-dimethyl-formamide at 20℃; for 24h;	79%

: 3365-85-3
4,4''-diamino-p-terphenyl

: 4,4'-diazidoterphenyl

Conditions

Conditions	Yield
Stage #1: 4,4''-diamino-p-terphenyl With hydrogenchloride; sodium nitrite In water at 0℃; for 0.5h; Cooling with ice; Stage #2: With sodium azide In water at 0℃; for 2h; Cooling with ice;	78.1%
Stage #1: 4,4''-diamino-p-terphenyl With sodium nitrite In water for 2h; Stage #2: With sodium azide In water for 2h;	45.6%

: 3365-85-3
4,4''-diamino-p-terphenyl

: 4β-bromo-4-desoxypodophyllotoxin

: 4'',4'''-[bis-(4β-N-4-desoxypodophyllotoxin)]-p-terphenyldiamine

Conditions

Conditions	Yield
With tetra-(n-butyl)ammonium iodide; triethylamine In tetrahydrofuran at 20℃; for 6h;	75%

: 3365-85-3
4,4''-diamino-p-terphenyl

: 75-03-6
ethyl iodide

: 68-12-2, 33513-42-7
N,N-dimethyl-formamide

: 53693-66-6
p,p"-bis-diethylamino-p-terphenyl

Conditions

Conditions	Yield
With calcium carbonate In N-methyl-acetamide; water	70%

...Expand

: 27550-59-0
4-hydroxyphthalic anhydride

: 3365-85-3
4,4''-diamino-p-terphenyl

: C34H20N2O6

Conditions

Conditions	Yield
With propionic acid at 150℃; for 10h;	70%

: 3365-85-3
4,4''-diamino-p-terphenyl

: meri-4,4''-diamino-p-terphenylochinon-diimoniumperchlorat

Conditions

Conditions	Yield
With potassium dichromate; perchloric acid; acetic acid In water	55.5%

: (CO)5CrC(OCH2CH3)CCC6H4CCC(OCH2CH3)Cr(CO)5

: 3365-85-3
4,4''-diamino-p-terphenyl

: [(CO)5CrC(OCH2CH3)CHC(NHC6H4C6H4C6H4NH2)]2C6H4

Conditions

Conditions	Yield
In tetrahydrofuran Schlenk techniques used, 7c (0.32 mmol) added to THF soln. of 5a (0.16 mmol) in THF under Ar, stirred for 2 h at room temp.; solvent removed under vac., chromd. (SiO2, hexane/AcOEt) under Ar pressure; elem. anal.;	47%

: 797056-47-4
2'-bromospiro[cyclopentane-1,9'-fluorene]

: 3365-85-3
4,4''-diamino-p-terphenyl

: C86H72N2

Conditions

Conditions	Yield
With sodium t-butanolate; bis-triphenylphosphine-palladium(II) chloride In xylene at 130℃; for 24h;	41%

: 797056-48-5
2'-bromo(spiro[cyclohexane-1,9'[9H]fluoren])

: 3365-85-3
4,4''-diamino-p-terphenyl

: C90H80N2

Conditions

Conditions	Yield
With sodium t-butanolate; bis-triphenylphosphine-palladium(II) chloride In xylene at 130℃; for 24h;	36%

: copper(II) perchlorate hexahydrate

: 4097-89-6
2,2',2''-triaminotriethylamine

: 3365-85-3
4,4''-diamino-p-terphenyl

: [(copper(II))2(tris(2-aminoethyl)amine)2(4,4'-p-terphenylenediamine)](perchlorate)4

Conditions

Conditions	Yield
In N,N-dimethyl-formamide tren (2 mmol) added to soln. of Cu(ClO4)2*6H2O (2 mmol) under stirring, NH2(C6H4)3NH2 (1 mmol) soln. added dropwise; soln. filtered off, Et2O slow diffused into soln., crystd. for one week at room temp., collected, air dried; elem. anal.;	31%

...Expand

: 75-44-5
phosgene

: 3365-85-3
4,4''-diamino-p-terphenyl

: terphenyl-4,4''-diisocyanate

Conditions

Conditions	Yield
In various solvent(s) for 3h; Condensation; Heating;	20%

: 3365-85-3
4,4''-diamino-p-terphenyl

: 918497-00-4
α-chlorobenzaldehyde phenylhydrazone

: C44H30N6

Conditions

Conditions	Yield
Stage #1: 4,4''-diamino-p-terphenyl; α-chlorobenzaldehyde phenylhydrazone With triethylamine In tetrahydrofuran for 24h; Reflux; Stage #2: With palladium 10% on activated carbon; 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane for 24h;	14%

: (tris(3,5-dimethylpyrazol-1-yl)hydroborate)(nitrosyl)diiodomolybdenum-toluene (1/1)

: 3365-85-3
4,4''-diamino-p-terphenyl

: [MoNOBH((CH3)2C3HN2)3(NHC6H4)2C6H4]3

Conditions

Conditions	Yield
With Na In toluene soln. of Mo-complex and ligand in toluene contg. Na was heated under reflux, stirred for 18 h under N2, cooled; filtered, solvent was removed in vacuo, sepd. by column chromy. with CH2Cl2/hexane; elem. anal.;	2%

: 13669-05-1
1,4-bis(thiophen-2-yl)butane-1,4-dione

: 3365-85-3
4,4''-diamino-p-terphenyl

: C42H28N2S4

Conditions

Conditions	Yield
With acetic acid In toluene for 48h; Knorr Pyrazole Synthesis; Inert atmosphere; Reflux;
In acetic acid; toluene at 130℃; for 72h; Inert atmosphere;	0.24%

: 3365-85-3
4,4''-diamino-p-terphenyl

: 4084-45-1
1,4-bis[2-(4-hydroxyphenyl)-2-propylene]benzene

Conditions

Conditions	Yield
With hydrogenchloride Diazotization.Einleiten von Wasserdampf;

: 3365-85-3
4,4''-diamino-p-terphenyl

: 118-55-8
phenyl Salicylate

: 117042-61-2
N,N'-p-terphenyl-4,4''-diyl-bis-salicylamide

Conditions

Conditions	Yield
With 1-Methylnaphthalene

: 3365-85-3
4,4''-diamino-p-terphenyl

: 21615-34-9
2-Methoxybenzoyl chloride

: 133326-34-8
4,4''-Bis-(2-methoxy-benzoylamino)-p-terphenyl

Conditions

Conditions	Yield
With pyridine

4,4''-Diamino-p-terphenyl Specification

The 4,4''-Diamino-p-terphenyl, with the CAS registry number 3365-85-3, has the systematic name of 1,1':4',1''-terphenyl-4,4''-diamine. And the molecular formula of the chemical is C₁₈H₁₆N₂.

The characteristics of this chemical are as followings: (1)ACD/LogP: 3.22; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 3.17; (4)ACD/LogD (pH 7.4): 3.22; (5)ACD/BCF (pH 5.5): 146.69; (6)ACD/BCF (pH 7.4): 164.73; (7)ACD/KOC (pH 5.5): 1196.24; (8)ACD/KOC (pH 7.4): 1343.32; (9)#H bond acceptors: 2; (10)H bond donors: 4; (11)#Freely Rotating Bonds: 4; (12)Polar Surface Area: 6.48 Å²; (13)Index of Refraction: 1.67; (14)Molar Refractivity: 83.9 cm³; (15)Molar Volume: 224.5 cm³; (16)Polarizability: 33.26×10^-24cm³; (17)Surface Tension: 52.9 dyne/cm; (18)Density: 1.159 g/cm³; (19)Flash Point: 296.3 °C; (20)Enthalpy of Vaporization: 74.95 kJ/mol; (21)Boiling Point: 484.2 °C at 760 mmHg; (22)Vapour Pressure: 1.57E-09 mmHg at 25°C.

You should be very cautious while dealing with this chemical. It is harmful by inhalation, in contact with skin and if swallowed, and it may cause cancer. Therefore, you had better take the following instructions: Avoid exposure - obtain special instruction before use; In case of accident or if you feel unwell, seek medical advice immediately (show label where possible).

Addtionally, the following datas could be converted into the molecular structure:
(1)SMILES: c3c(c1ccc(N)cc1)ccc(c2ccc(N)cc2)c3
(2)InChI: InChI=1/C18H16N2/c19-17-9-5-15(6-10-17)13-1-2-14(4-3-13)16-7-11-18(20)12-8-16/h1-12H,19-20H2
(3)InChIKey: QBSMHWVGUPQNJJ-UHFFFAOYAO

Product Name

4,4''-DIAMINO-P-TERPHENYL

Synthetic route

4,4''-Diamino-p-terphenyl Specification

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