Benzidine supplier | CasNO.92-87-5

Name
Benzidine
EINECS 202-199-1
CAS No. 92-87-5
Article Data256
CAS DataBase
Density 1.156 g/cm³
Solubility Sparingly soluble in water. <0.1 g/100 mL at 22 °C
Melting Point 127-128 °C
Formula C₁₂H₁₂N₂
Boiling Point 358.7 °C at 760 mmHg
Molecular Weight 184.241
Flash Point 203.5 °C
Transport Information UN 1885 6.1/PG 2
Appearance off-white solid
Safety 53-45-60-61-36/37-16-7-36-26
Risk Codes 45-22-50/53-52/53-39/23/24/25-23/24/25-11-36/37/38-20/21/22
Molecular Structure
Hazard Symbols T,N,F,Xn
Synonyms Benzidine(8CI);4,4'-Bianiline;4,4'-Biphenyldiamine;4,4'-Diamino-1,1'-biphenyl;4,4'-Diaminobiphenyl;4,4'-Diaminodiphenyl;4,4'-Diphenylenediamine;4-(4-Aminophenyl)aniline;4'-Amino-[1,1'-biphenyl]-4-ylamine;C.I. Azoic DiazoComponent 112;Fast Corinth Base B;NSC 146476;p,p'-Bianiline;p,p'-Diaminobiphenyl;p-Diaminodiphenyl;
PSA 52.04000
LogP 3.68040

Synthetic route

: 92-86-4
4-(4-bromophenyl)bromobenzene

: 92-87-5
p,p'-diaminobiphenyl

Conditions

Conditions	Yield
With C24H12Cu2F9N4O7; tetrabutylammomium bromide; ammonia; caesium carbonate In water; ethylene glycol at 110 - 140℃; for 16h;	100%
With bis(tri-ortho-tolylphosphine)palladium(0); (R)-(-)-1-[(S)-2-(dicyclohexylphosphino)ferrocenyl]ethyl-di-tert-butylphosphine; ammonia; sodium t-butanolate In 1,4-dioxane at 100℃; for 12h; Inert atmosphere;	79%

: 540-37-4
p-aminoiodobenzene

: 92-87-5
p,p'-diaminobiphenyl

Conditions

Conditions	Yield
With magnesium In water at 100℃; for 2h; Sealed tube;	96%
With tetrabutylammomium bromide; palladium diacetate; potassium carbonate In water; N,N-dimethyl-formamide Buchwald-Hartwig Coupling;	75%
With tetrabutylammonium tetrafluoroborate In acetonitrile at 20℃; for 8h; Electrochemical reaction;	38%

: 1528-74-1
4,4'-dinitrobiphenyl

: 92-87-5
p,p'-diaminobiphenyl

Conditions

Conditions	Yield
With hydrazine In methanol at 50℃;	95%
With sodium tetrahydroborate In ethanol at 24.84℃; for 2h;	95%
With hydrazine hydrate In ethanol at 70℃; for 4h; chemoselective reaction;	93%

: 106-47-8
4-chloro-aniline

: 92-87-5
p,p'-diaminobiphenyl

Conditions

Conditions	Yield
With carbon dioxide; aluminium; 1-butyl-3-methylimidazolium trifluoromethanesulfonimide at 65℃; under 116262 Torr; for 16h; Ullmann reaction;	95%
With 4-(3'-butyl-1'-imidazolio)-1-butanesulfonic acid hydrogen sulfate; aluminium In carbon dioxide at 45℃; under 116262 Torr; for 16h; Ullmann reaction; Supercritical conditions;	94%
With sulphonic acid functionalized porphyrin meso-substituted triazolium anchored ionic liquid at 20℃; for 16h; Catalytic behavior; Time; Ullmann Condensation; Irradiation;	91%

: 106-40-1
4-bromo-aniline

: 92-87-5
p,p'-diaminobiphenyl

Conditions

Conditions	Yield
With palladium 10% on activated carbon; potassium acetate; bis(pinacol)diborane In ethanol at 60℃; for 8h; Suzuki-Miyaura Coupling; Inert atmosphere;	94.3%
With potassium carbonate In N,N-dimethyl-formamide for 0.75h;	90%
With magnesium In water at 100℃; for 3.5h; Sealed tube;	85%

: 3001-15-8
4,4'-diiodobiphenyl

: 92-87-5
p,p'-diaminobiphenyl

Conditions

Conditions	Yield
With copper(l) iodide; tetra(n-butyl)ammonium hydroxide; ammonia In water at 25℃; for 24h; Inert atmosphere; Sealed tube; chemoselective reaction;	91%

: 1221066-38-1
N4,N4'-bis(diphenylmethylene)biphenyl-4,4'-diamine

: 92-87-5
p,p'-diaminobiphenyl

Conditions

Conditions	Yield
With hydrogenchloride In tetrahydrofuran; water at 20℃; for 2h;	82%

: 586-78-7
para-nitrophenyl bromide

A: 106-40-1
4-bromo-aniline

B: 92-87-5
p,p'-diaminobiphenyl

Conditions

Conditions	Yield
With hydrazine hydrate In ethanol at 70℃; for 4h; chemoselective reaction;	A 82% B 7%

: 89415-43-0
(4-aminophenyl)boronic acid

: 92-87-5
p,p'-diaminobiphenyl

Conditions

Conditions	Yield
With dipotassium peroxodisulfate; potassium carbonate In water; acetone for 3h;	80%

: 122-66-7
diphenyl hydrazine

A: 492-17-1
2,4'-diaminobiphenyl

B: 92-87-5
p,p'-diaminobiphenyl

Conditions

Conditions	Yield
In ethanol; water	A 30% B 70%
With hydrogenchloride; lithium chloride In ethanol at 0℃; for 0.5h; Product distribution; kinetic isotope effects; reaction of var. labeled hydrazobenzenes, var. time;	A 91.5 mg B 15.8%
With hydrogenchloride; lithium chloride In ethanol at 0℃; for 0.5h;	A 91.5 mg B 15.8%

: 586-78-7
para-nitrophenyl bromide

: 92-87-5
p,p'-diaminobiphenyl

Conditions

Conditions	Yield
With L-Cysteine; potassium hydroxide In water; dimethyl sulfoxide at 100℃; for 0.333333h; Green chemistry;	70%
Multi-step reaction with 2 steps 1: copper / N,N-dimethyl-formamide / Heating 2: hydrazine; 3% Pd/C / ethanol / Heating View Scheme
Multi-step reaction with 2 steps 1: copper / N,N-dimethyl-formamide / 12 h / 160 °C 2: hydrazine; 3% Pd/C / ethanol / 12 h / 20 - 100 °C View Scheme

: 635-46-1
1,2,3,4-tetrahydroisoquinoline

: 1211-40-1
4-amino-4'-nitrobiphenyl

A: 91-22-5
quinoline

B: 92-87-5
p,p'-diaminobiphenyl

Conditions

Conditions	Yield
With nickel-nitrogen-doped carbon framework In water at 145℃; for 18h; Inert atmosphere; Sealed tube; Green chemistry;	A 68% B 70%

...Expand

: 122-66-7
diphenyl hydrazine

: 92-87-5
p,p'-diaminobiphenyl

Conditions

Conditions	Yield
With hydrogenchloride In water for 3h; Reflux;	67%
With hydrogenchloride In ethanol at 0℃; for 2.5h; Rearrangement;	51%
Thermodynamic data;

: 1227476-15-4
Azobenzene

A: 62-53-3
aniline

B: 92-87-5
p,p'-diaminobiphenyl

Conditions

Conditions	Yield
With LiCrH42LiCl2THF In tetrahydrofuran at 25℃; for 12h;	A 64% B 31%
With hydrogenchloride; N-benzylthiazolium bromide; benzaldehyde; triethylamine 1) MeOH, r.t., 20 h, 2) MeOH, HCl; Yield given. Multistep reaction. Yields of byproduct given;

: 636-98-6
p-nitrobenzene iodide

A: 92-87-5
p,p'-diaminobiphenyl

B: 540-37-4
p-aminoiodobenzene

Conditions

Conditions	Yield
With hydrazine hydrate In ethanol at 70℃; for 4h; chemoselective reaction;	A 27% B 55%

: 100-00-5
4-chlorobenzonitrile

: 92-87-5
p,p'-diaminobiphenyl

Conditions

Conditions	Yield
With L-Cysteine; potassium hydroxide In water; dimethyl sulfoxide at 100℃; for 0.666667h; Green chemistry;	55%

: 106-40-1
4-bromo-aniline

: 7440-66-6
zinc

A: 301300-48-1
NH2C6H4ZnBr

B: 62-53-3
aniline

C: 92-87-5
p,p'-diaminobiphenyl

Conditions

Conditions	Yield
With trifluoroacetic acid; cobalt(II) bromide; zinc dibromide In acetonitrile the mixt. in CH3CN was stirred at room temp., then arylbromide was added, stirred at room temp.; GC analysis;	A 40% B 52% C 0%

...Expand

: 98-95-3
nitrobenzene

A: 62-53-3
aniline

B: 1227476-15-4
Azobenzene

C: 92-87-5
p,p'-diaminobiphenyl

Conditions

Conditions	Yield
With lithium aluminium tetrahydride; titanium tetrachloride In diethyl ether at 20℃; for 15h; Solvent; Inert atmosphere;	A 48% B 25% C 5%

...Expand

: 92-52-4
biphenyl

A: 1454-80-4
1,1'-biphenyl-2,2'-diamine

B: 92-87-5
p,p'-diaminobiphenyl

Conditions

Conditions	Yield
With 9,10-Dicyanoanthracene; ammonia In water; acetonitrile for 20h; Irradiation;	A 13% B 43%

: 367-24-8
4-bromo-2-fluoroaniline

A: 2-fluorobenzidine

B: 448-97-5
3,3'-difluorobiphenyl-4,4'-diamine

C: 92-87-5
p,p'-diaminobiphenyl

Conditions

Conditions	Yield
With sodium hydroxide; sodium formate; cetyltrimethylammonim bromide; palladium on activated charcoal In water for 4h; Heating;	A 15% B 33% C 10%
Stage #1: 4-bromo-2-fluoroaniline With palladium on activated charcoal; sodium formate; cetyltrimethylammonim bromide; sodium hydroxide In water for 4h; Reflux; Stage #2: With sodium acetate for 20h; Reflux;

...Expand

: 106-39-8
bromochlorobenzene

: 52234-21-6
(adamantane-1,3-diyl)dimethanamine

A: 1287287-13-1
3-(4-chlorophenylaminomethyl)adamantane-1-carbaldehyde

B: 1287287-09-5
4-chloro-N-[3-(4-chlorophenylaminomethyl)adamantan-1-ylmethyl]aniline

C: 106-47-8
4-chloro-aniline

D: 92-87-5
p,p'-diaminobiphenyl

Conditions

Conditions	Yield
With 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; bis(dibenzylideneacetone)-palladium(0); sodium t-butanolate In 1,4-dioxane for 7h; Inert atmosphere; Reflux;	A 25% B 31% C 18% D 7%

...Expand

: 2515-46-0
3-methyl-1,5-diphenyl-4,5-dihydro-1H-pyrazole

A: 29475-88-5
trans-2-styrylindole

B: 1896-62-4
(E)-benzalacetone

C: 92-87-5
p,p'-diaminobiphenyl

Conditions

Conditions	Yield
With PPA; Polyphosphoric acid (PPA) at 170℃; for 0.666667h;	A 30% B n/a C 0.35 g

...Expand

: 2515-46-0
3-methyl-1,5-diphenyl-4,5-dihydro-1H-pyrazole

A: 29475-88-5
trans-2-styrylindole

B: 122-57-6
1-Phenylbut-1-en-3-one

C: 92-87-5
p,p'-diaminobiphenyl

Conditions

Conditions	Yield
With PPA at 130℃; Product distribution; Mechanism; studies of the Fischer indole synthesis;	A 25% B 21% C 18%
With PPA at 130℃;	A 25% B 21% C 18%

...Expand

: 106-37-6
1.4-dibromobenzene

: 51545-05-2
1,3-bis(aminoethyl)adamantane

A: C20H26BrNO

B: C26H33BrN2

C: 1287287-20-0
4-bromo-N-(2-{3-[2-(4-bromophenylamino)ethyl]adamantan-1-yl}ethyl)aniline

D: 106-40-1
4-bromo-aniline

E: 92-87-5
p,p'-diaminobiphenyl

Conditions

Conditions	Yield
With 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; bis(dibenzylideneacetone)-palladium(0); sodium t-butanolate In 1,4-dioxane for 7h; Inert atmosphere; Reflux;	A n/a B n/a C 11% D 7% E 9%

...Expand

: 7073-69-0
2-(2-bromophenyl)propanol

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

A: C15H17NO

B: 92-87-5
p,p'-diaminobiphenyl

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate Suzuki Coupling; Inert atmosphere;	A 10% B n/a

...Expand

: 109-99-9
tetrahydrofuran

: 24488-76-4
phenylcalcium iodide

A: 92-52-4
biphenyl

B: 1126-79-0
n-butyl phenyl ether

C: 1227476-15-4
Azobenzene

D: 92-87-5
p,p'-diaminobiphenyl

Conditions

Conditions	Yield
With dinitrogen monoxide Ambient temperature; Yield given;	A n/a B n/a C 6% D n/a
With dinitrogen monoxide Product distribution; Ambient temperature;	A n/a B n/a C 6% D n/a

...Expand

: 110-86-1
pyridine

: 855256-72-3
4,4'-Bis-(N'-phenyl-hydrazino)-biphenyl

: 64-19-7
acetic acid

A: 120623-26-9
4,4'-Bis-(phenyl-trans-azo)-biphenyl

B: 62-53-3
aniline

C: 1797-23-5
4'-phenylazo-biphenyl-4-ylamine

D: 92-87-5
p,p'-diaminobiphenyl

Conditions

Conditions	Yield
unter Kohlendioxid;

...Expand

: 636-98-6
p-nitrobenzene iodide

: 92-87-5
p,p'-diaminobiphenyl

Conditions

Conditions	Yield
With potassium hydroxide; hydrazine hydrate; palladium

: 108-24-7
acetic anhydride

: 92-87-5
p,p'-diaminobiphenyl

: 613-35-4
N,N'-Diacetylbenzidin

Conditions

Conditions	Yield
Acetylation;	100%
In acetone for 3h;	100%
for 0.00277778h; Green chemistry;	98%

: 92-87-5
p,p'-diaminobiphenyl

: benzidine dication

Conditions

Conditions	Yield
With ammonium vanadate; sulfuric acid	100%
With ammonium cerium(IV) nitrate; sulfuric acid In water

: 104-88-1
4-chlorobenzaldehyde

: 92-87-5
p,p'-diaminobiphenyl

: N4-[1-(4-Chloro-phenyl)-meth-(E)-ylidene]-biphenyl-4,4'-diamine

Conditions

Conditions	Yield
for 120h; Ambient temperature;	100%

: (NCNdipp)3Lu3(μ2-Me)3(μ3-Me)(μ3-CH2)

: 92-87-5
p,p'-diaminobiphenyl

: {(PhC(NC6H3iPr2-2,6)2)3Lu3(μ-Me)3(μ3-Me)}2{μ-η1:η1:η3:η3:η1:η1-N(C6H4)2N}

Conditions

Conditions	Yield
In tetrahydrofuran at 20℃; for 48h;	100%

: 774-74-3
2-(2,4-dichlorophenoxy)acetyl chloride

: 92-87-5
p,p'-diaminobiphenyl

: 2-(2,4-dichloro-phenoxy)-N-{4'-[2-(2,4-dichloro-phenoxy)-acetylamino]-biphenyl-4-yl}-acetamide

Conditions

Conditions	Yield
With sodium hydroxide; PEG-600 In dichloromethane; water at 20℃; for 1h; Acylation;	99%

: 37784-17-1
N-(tert-butoxycarbonyl)-D-proline

: 92-87-5
p,p'-diaminobiphenyl

: (2R,2'R)-di-tert-butyl 2,2'-(([1,1'-biphenyl]-4,4'-diylbis(azanediyl))bis(carbonyl))bis(pyrrolidine-1-carboxylate)

Conditions

Conditions	Yield
With N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In dichloromethane at 20℃; for 2h;	99%
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 2h;	99%

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

: 92-87-5
p,p'-diaminobiphenyl

: C34H36N2O2

Conditions

Conditions	Yield
With formic acid In methanol at 20℃; for 25h; Reflux;	99%

: 4314-19-6
bis(1H-benzo[d][1,2,3]triazol-1-yl)methanethione

: 92-87-5
p,p'-diaminobiphenyl

: N,N'-bis(benzotriazole-1-thiocarbamoyl)benzidine

Conditions

Conditions	Yield
In acetonitrile for 0.166667h; Milling; Green chemistry;	99%

: C9H11ClOSn

: 92-87-5
p,p'-diaminobiphenyl

: C30H30Cl2N2Sn2

Conditions

Conditions	Yield
In melt for 0.333333h;	99%

: 98-09-9
benzenesulfonyl chloride

: 92-87-5
p,p'-diaminobiphenyl

: 52945-06-9
N,N'-(biphenyl-4,4'-diyl)dibenzenesulfonamide

Conditions

Conditions	Yield
With pyridine In dichloromethane at 20℃; for 4h; pH=Ca. 8;	98%
With pyridine

: 591-17-3
meta-bromotoluene

: 108-90-7
chlorobenzene

: 92-87-5
p,p'-diaminobiphenyl

: 65181-78-4
4,4'-bis(m-tolylphenylamino)biphenyl

Conditions

Conditions	Yield
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

: 5396-30-5
9-chloro-1,2,3,4-tetrahydroacridine

: 76-05-1
trifluoroacetic acid

: 92-87-5
p,p'-diaminobiphenyl

: N-(4-{4-[(1,2,3,4-tetrahydroacridin-9-yl)amino]phenyl}phenyl)-1,2,3,4-tetrahydroacridin-9-amine tetra(trifluoroacetic acid)

Conditions

Conditions	Yield
Stage #1: 9-chloro-1,2,3,4-tetrahydroacridine; p,p'-diaminobiphenyl With trichlorophosphate In pentan-1-ol for 40h; Reflux; Stage #2: trifluoroacetic acid In water	98%

...Expand

: 24677-78-9
2,3-dihydroxybenzaldehyde

: 92-87-5
p,p'-diaminobiphenyl

: bis-(2,3-dihydroxy-benzylidene)-benzidine

Conditions

Conditions	Yield
In methanol	97%
With ethanol

: 24424-99-5
di-tert-butyl dicarbonate

: 92-87-5
p,p'-diaminobiphenyl

: 206182-66-3
tert-butyl (4'-amino-[1,1'-biphenyl]-4-yl)carbamate

Conditions

Conditions	Yield
With potassium carbonate In tetrahydrofuran; water; N,N-dimethyl-formamide at 20℃; for 5h;	97%
With sodium carbonate In 1,4-dioxane Ambient temperature;	90%
In 1,4-dioxane at 20℃; for 24h; Inert atmosphere;	85%
In 1,4-dioxane for 24.5h; Inert atmosphere;	85%
In 1,4-dioxane at 20℃; for 25h; Inert atmosphere;	85%

: 92-87-5
p,p'-diaminobiphenyl

: naphthalen-2-ylmethyl pyridine-2-carbimidothioate hydrobromide

: N,N'-([1,1'-biphenyl]-4,4'-diyl)dipicolinimidamide dihydrochloride

Conditions

Conditions	Yield
Stage #1: p,p'-diaminobiphenyl; naphthalen-2-ylmethyl pyridine-2-carbimidothioate hydrobromide In ethanol; acetonitrile at 20℃; Cooling with ice; Stage #2: With sodium hydroxide In ethanol at 0℃; pH=Ca. 10; Stage #3: With hydrogenchloride In ethanol at 0 - 20℃;	97%

: 1613522-41-0
1-(benzyloxy)-3-((2,4-difluorobenzyl)carbamoyl)-2-oxo-1,2-dihydro-1,8-naphthyridin-4-yl 4-methylbenzenesulfonate

: 92-87-5
p,p'-diaminobiphenyl

: 1613522-45-4
4-((4'-amino-[1,1'-biphenyl]-4-yl)amino)-1-(benzyloxy)-N-(2,4-difluorobenzyl)-2-oxo-1,2-dihydro-1,8-naphthyridine-3-carboxamide

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 50℃; for 1h;	97%

: 58125-40-9
2-(2-chloroacetamido)-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carbonitrile

: 92-87-5
p,p'-diaminobiphenyl

: 2-((4'-amino-[1,1'-biphenyl]-4-yl)amino)-N-(3-cyano-4,5,6,7-tetrahydrobenzo[b]thiophen-2-yl)acetamide

Conditions

Conditions	Yield
In 1,4-dioxane for 4h; Reflux;	97%

: 188047-59-8
C12H8ClN3OS

: 92-87-5
p,p'-diaminobiphenyl

: 1190107-86-8
C36H28Cl2N8O2S2

Conditions

Conditions	Yield
In acetonitrile at 20 - 25℃; for 0.75h; Sonication;	96%

: 123-11-5
4-methoxy-benzaldehyde

: 762-04-9
phosphonic acid diethyl ester

: 92-87-5
p,p'-diaminobiphenyl

: tetraethyl (1,4-phenylene bis(azanediyl))bis(p-methoxymethylene)diphosphonate

Conditions

Conditions	Yield
With 1,10-((ethane-1,2-diylbis(oxy))bis(ethane-2,1-diyl))bis(3-sulfo-1H benzimidazol-3-ium)chloride In neat (no solvent) at 50℃; for 1h; Green chemistry;	96%

...Expand

: 92-87-5
p,p'-diaminobiphenyl

: 1528-74-1
4,4'-dinitrobiphenyl

Conditions

Conditions	Yield
With tert.-butylhydroperoxide; potassium iodide In water; acetonitrile at 80℃; for 15h;	95%
With tert.-butylhydroperoxide; 3 A molecular sieve; zirconium(IV) tert-butoxide In dichloromethane for 5h; Ambient temperature;	90%
With sulfuric acid Diazotization.Behandlung der Diazoniumsalz-Loesung mit NaNO2 und Kupfer(I)-kupfer(II)-sulfit;

: 123-08-0
4-hydroxy-benzaldehyde

: 92-87-5
p,p'-diaminobiphenyl

: 132556-90-2
4-amino-4'-(p-hydroxy)benzylideneimino-1,1'-biphenyl

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In N,N-dimethyl-formamide at 80℃; for 4h;	95%
With piperidine In ethanol Heating;

: 5100-23-2
2-isocyanatobenzoyl chloride

: 92-87-5
p,p'-diaminobiphenyl

: 131526-24-4
3,3'-(4,4'-Biphenylene)bis(2,4-dioxo-1,2,3,4-tetrahydroquinazoline)

Conditions

Conditions	Yield
With triethylamine In toluene 1.) 1 h, 0 deg C, 2.) 1 h, room temperature, 3.) 36 h, reflux;	95%

: 64-18-6
formic acid

: 92-87-5
p,p'-diaminobiphenyl

: N-monoformylbenzidine

Conditions

Conditions	Yield
In di-isopropyl ether Heating;	95%

: 108-90-7
chlorobenzene

: 92-87-5
p,p'-diaminobiphenyl

: 531-91-9
N,N'-diphenyl-p-phenylenediamine

Conditions

Conditions	Yield
With sodium t-butanolate; Ni(0)*2IPr In 1,4-dioxane at 100℃;	95%
With palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium hydroxide In tetrahydrofuran; ethanol; water; toluene; tert-butyl alcohol at 100℃; for 16h; Glovebox; Inert atmosphere; Schlenk technique;	116.5 mg

: 90-02-8
salicylaldehyde

: 92-87-5
p,p'-diaminobiphenyl

: 70952-41-9
4,4'-bis{5-(1-formyl-2-hydroxyphenyl)azo}diphenyl

Conditions

Conditions	Yield
Stage #1: p,p'-diaminobiphenyl With hydrogenchloride; sodium nitrite In water Cooling with ice; Stage #2: salicylaldehyde With sodium hydroxide In water at 0 - 5℃;	95%
Multistep reaction.;	76%

: 90-46-0
9-hydroxyxanthene

: 92-87-5
p,p'-diaminobiphenyl

: 1408244-78-9
N4,N4'-di(9H-xanthen-9-yl)-[1,1'-biphenyl]-4,4’-diamine

Conditions

Conditions	Yield
With ferric hydrogen sulphate In ethanol for 0.5h; Reflux; regioselective reaction;	95%

Benzidine Consensus Reports

NTP 10th Report on Carcinogens. IARC Cancer Review: Human Limited Evidence IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 1 , (World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210)(1972),p. 80. ; Human Sufficient Evidence IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 29 , (World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210)(1982),p. 149. ; Animal Sufficient Evidence IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 1 , (World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210)(1972),p. 80. ; IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 29 , (World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210)(1982),p. 149. . EPA Genetic Toxicology Program. Community Right-To-Know List. Reported in EPA TSCA Inventory.

Benzidine Standards and Recommendations

OSHA PEL: OSHA: Cancer Suspect Agent
ACGIH TLV: Confirmed Human Carcinogen
DFG MAK: Human Carcinogen
DOT Classification: 6.1; Label: Poison

Benzidine Analytical Methods

For occupational chemical analysis use OSHA: #ID-65 or NIOSH: Benzidine in Urine (TLC), 8304; Benzidine in Urine (GC), 8306.

Benzidine Specification

The Benzidine with CAS registry number of 92-87-5 is also known as [1,1'-Biphenyl]-4,4'-diamine. The IUPAC name is 4-(4-Aminophenyl)aniline. It belongs to product categories of Intermediates of Dyes and Pigments; Azo dye; Amines; Aromatics; Method 8270More...Close...;8000 Series Solidwaste Methods; Analytical Standards; AromaticsChemical Class; AromaticsMethod Specific; BenzidinesEPA; Chemical Class; A-BMethod Specific; Aryl Amines MAK III, Category 1Alphabetic; Alpha Sort; B; BA - BHEnvironmental Standards; Benzidines; Oeko-Tex Standard 100; Volatiles/ Semivolatiles. Its EINECS registry number is 202-199-1. In addition, the formula is C₁₂H₁₂N₂ and the molecular weight is 184.24.

Physical properties about Benzidine are: (1)ACD/LogP: 1.56; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.5; (4)ACD/LogD (pH 7.4): 1.56; (5)ACD/BCF (pH 5.5): 7.83; (6)ACD/BCF (pH 7.4): 9.06; (7)ACD/KOC (pH 5.5): 145.68; (8)ACD/KOC (pH 7.4): 168.41; (9)#H bond acceptors: 2; (10)#H bond donors: 4; (11)#Freely Rotating Bonds: 3; (12)Polar Surface Area: 6.48Å²; (13)Index of Refraction: 1.667; (14)Molar Refractivity: 59.31 cm³; (15)Molar Volume: 159.2 cm³; (16)Polarizability: 23.51×10^-24cm³; (17)Surface Tension: 54.2 dyne/cm; (18)Density: 1.156 g/cm³; (19)Flash Point: 203.5 °C; (20)Enthalpy of Vaporization: 60.43 kJ/mol; (21)Boiling Point: 358.7 °C at 760 mmHg; (22)Vapour Pressure: 2.5E-05 mmHg at 25 °C.

Preparation of Benzidine: it is prepared in a two step process from nitrobenzene. First, the nitrobenzene is converted to 1,2-diphenylhydrazine, usually using iron powder as the reducing agent. Treatment of this hydrazine with mineral acids induces a rearrangement reaction to 4,4'-benzidine. Smaller amounts of other isomers are also formed. The benzidine rearrangement, which proceeds intramolecularly, is a classic mechanistic puzzle in organic chemistry.

Benzidine is prepared in a two step process from nitrobenzene.

Uses of Benzidine: it has been significantly withdrawn from use in most industries because it is so carcinogenic. In the past, benzidine was used to test for blood. An enzyme in blood causes the oxidation of benzidine to a distinctively blue-coloured derivative. The test for cyanide relies on similar reactivity. Such applications have largely been replaced by methods using phenolphthalein/hydrogen peroxide and luminol.

When you are using this chemical, please be cautious about it. As a chemical, it is irritating to eyes, respiratory system and skin. This chemical is very toxic to aquatic organisms and may cause long-term adverse effects in the aquatic environment. Besides, it's danger of very serious irreversible effects through inhalation, in contact with skin and if swallowed. This chemical even may cause cancer. During using it, wear suitable protective clothing, gloves and eye/face protection. Keep away from sources of ignition and keep container tightly closed. This material and its container must be disposed of as hazardous waste. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. What's more, if you feel unwell seek or accident happens medical advice immediately.

You can still convert the following datas into molecular structure:
1. SMILES: c2c(c1ccc(N)cc1)ccc(N)c2
2. InChI: InChI=1/C12H12N2/c13-11-5-1-9(2-6-11)10-3-7-12(14)8-4-10/h1-8H,13-14H2
3. InChIKey: HFACYLZERDEVSX-UHFFFAOYAX
4. Std. InChI: InChI=1S/C12H12N2/c13-11-5-1-9(2-6-11)10-3-7-12(14)8-4-10/h1-8H,13-14H2
5. Std. InChIKey: HFACYLZERDEVSX-UHFFFAOYSA-N

The toxicity data is as follows:

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Source
dog	LDLo	oral	200mg/kg (200mg/kg)	Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 58, Pg. 167, 1907.
mouse	LD50	intraperitoneal	110mg/kg (110mg/kg)	Progress in Mutation Research. Vol. 1, Pg. 682, 1981.
mouse	LD50	oral	214mg/kg (214mg/kg)	National Technical Information Service. Vol. PB214-270,
rabbit	LDLo	oral	200mg/kg (200mg/kg)	Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 58, Pg. 167, 1907.
rat	LD50	oral	309mg/kg (309mg/kg)	National Technical Information Service. Vol. PB214-270,

Product Name

Benzidine

Synthetic route

Benzidine Consensus Reports

Benzidine Standards and Recommendations

Benzidine Analytical Methods

Benzidine Specification

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