Product Name

  • Name

    4-Aminoazobenzene

  • EINECS 200-453-6
  • CAS No. 60-09-3
  • Article Data137
  • CAS DataBase
  • Density 1.12 g/cm3
  • Solubility 29.59mg/L(25 oC)
  • Melting Point 123-126 °C(lit.)
  • Formula C12H11N3
  • Boiling Point 360.7 °C at 760 mmHg
  • Molecular Weight 197.239
  • Flash Point 171.9 °C
  • Transport Information UN 3077 9/PG 3
  • Appearance powder
  • Safety 53-45-60-61
  • Risk Codes 45-50/53
  • Molecular Structure Molecular Structure of 60-09-3 (4-Aminoazobenzene)
  • Hazard Symbols ToxicT; DangerousN; CorrosiveC
  • Synonyms Benzenamine,4-(phenylazo)- (9CI);C.I. Solvent Yellow 1 (7CI,8CI);4-(Phenylazo)aniline;4-(Phenylazo)benzenamine;4-Aminoazobenzol;Aniline yellow;Brasilazina Oil Yellow G;C.I. 11000;Cellitazol R;Ceres Yellow R;Fast SpiritYellow;Fat Yellow AAB;NSC 2032;Oil Soluble Aniline Yellow;Oil Yellow AAB;Oil Yellow AB;Oil Yellow AN;Oil Yellow B;Organol Yellow 2A;Solvent Yellow1;Somalia Yellow 2G;Sudan Yellow R;p-(Phenylazo)aniline;p-Aminoazobenzene;p-Aminoazobenzol;p-Aminodiphenylimide;
  • PSA 50.74000
  • LogP 4.26540

Synthetic route

1,3-Diphenyltriazen
297766-64-4

1,3-Diphenyltriazen

aniline yellow
60-09-3

aniline yellow

Conditions
ConditionsYield
With K10-montmorillonite-H+ at 20℃; for 3h; Product distribution; Isomerization;100%
Mechanism;
With sodium hydroxide at 50℃; pH=8;
With hydrogenchloride In methanol; water at 40℃; for 2h; Temperature; Solvent;
4-(N'-phenyl-hydrazino)-aniline
19689-52-2

4-(N'-phenyl-hydrazino)-aniline

aniline yellow
60-09-3

aniline yellow

Conditions
ConditionsYield
With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical In ethanol at 60℃; for 12h; Green chemistry;95%
aniline
62-53-3

aniline

aniline yellow
60-09-3

aniline yellow

Conditions
ConditionsYield
Stage #1: With bentonite GB clay; sodium nitrite at 0 - 5℃; for 1h;
Stage #2: aniline at 0 - 20℃;
94%
With hydrogenchloride; sodium nitrite In water at 0 - 5℃;80%
Stage #1: aniline With hydrogenchloride; sodium nitrite In water at 0 - 5℃; for 1.16667h;
Stage #2: aniline With hydrogenchloride In water at 0 - 5℃; for 3h;
Stage #3: With ammonia In water
71%
1,3-Diphenyltriazen
297766-64-4

1,3-Diphenyltriazen

A

aniline yellow
60-09-3

aniline yellow

B

2-aminoazobenzene
2835-58-7

2-aminoazobenzene

Conditions
ConditionsYield
With hydrogenchloride In ethanol at 30℃; for 48h;A 75%
B 8.2%
With hydrogenchloride In methanol at 30℃; for 48h; Product distribution; var. solvents;A 64%
B 5.8%
With hydrogenchloride In tert-butyl alcohol at 30℃; for 48h;A 61%
B 14%
aniline hydrochloride
142-04-1

aniline hydrochloride

aniline
62-53-3

aniline

aniline yellow
60-09-3

aniline yellow

Conditions
ConditionsYield
Stage #1: aniline With hydrogenchloride; sodium nitrite In water at 0 - 5℃; for 1h;
Stage #2: aniline hydrochloride In water at 0 - 5℃; for 3h;
Stage #3: With ammonia In water
73%
4-nitroazobenzene
2491-52-3

4-nitroazobenzene

A

aniline yellow
60-09-3

aniline yellow

B

4-nitrohydrazobenzene
34139-26-9

4-nitrohydrazobenzene

Conditions
ConditionsYield
With sodium dithionite; 1,1′-dioctyl-4,4′-bipyridinium; potassium carbonate In water; acetonitrile at 35℃; for 1h;A 20%
B 62%
aniline hydrochloride
142-04-1

aniline hydrochloride

aniline
62-53-3

aniline

1,3-Diphenyltriazen
297766-64-4

1,3-Diphenyltriazen

aniline yellow
60-09-3

aniline yellow

Conditions
ConditionsYield
at 40 - 45℃; for 1h; Inert atmosphere;62%
o-toluidine
95-53-4

o-toluidine

1,3-Diphenyltriazen
297766-64-4

1,3-Diphenyltriazen

A

aniline yellow
60-09-3

aniline yellow

B

2-methyl-4-phenylazo-aniline
1142-13-8

2-methyl-4-phenylazo-aniline

Conditions
ConditionsYield
With K10-montmorillonite at 20℃; for 6h; Product distribution; Addition;A 5%
B 42%
p-toluidine
106-49-0

p-toluidine

1,3-Diphenyltriazen
297766-64-4

1,3-Diphenyltriazen

A

aniline yellow
60-09-3

aniline yellow

B

4-methyl-2-phenylazoaniline
313485-86-8

4-methyl-2-phenylazoaniline

Conditions
ConditionsYield
With K10-montmorillonite at 20℃; for 6h; Product distribution; Addition;A 21%
B 36%
N,N-diethyl-4-phenylazoaniline N-oxide
108193-68-6

N,N-diethyl-4-phenylazoaniline N-oxide

A

aniline yellow
60-09-3

aniline yellow

B

N-ethyl-4-aminoazobenzene
2058-67-5

N-ethyl-4-aminoazobenzene

C

4-(diethylamino)azobenzene
2481-94-9

4-(diethylamino)azobenzene

Conditions
ConditionsYield
In benzene at 17℃; for 5h; Irradiation;A 23%
B 10%
C 28%
quinoline
91-22-5

quinoline

quinoline hydrochloride
530-64-3

quinoline hydrochloride

1,3-Diphenyltriazen
297766-64-4

1,3-Diphenyltriazen

aniline yellow
60-09-3

aniline yellow

Conditions
ConditionsYield
at 40 - 50℃;
formic acid
64-18-6

formic acid

aniline hydrochloride
142-04-1

aniline hydrochloride

benzene diazonium chloride
100-34-5

benzene diazonium chloride

aniline yellow
60-09-3

aniline yellow

Conditions
ConditionsYield
at 0℃;
ethanol
64-17-5

ethanol

1,5-diphenyl-3-methylpentazene
41798-82-7

1,5-diphenyl-3-methylpentazene

aniline hydrochloride
142-04-1

aniline hydrochloride

aniline yellow
60-09-3

aniline yellow

aniline hydrochloride
142-04-1

aniline hydrochloride

4-benzenesulfonylamino-benzenediazonium-betaine
36071-24-6

4-benzenesulfonylamino-benzenediazonium-betaine

A

N-phenylsulfonyl-1,4-phenylenediamine
5466-91-1

N-phenylsulfonyl-1,4-phenylenediamine

B

aniline yellow
60-09-3

aniline yellow

Conditions
ConditionsYield
With aniline at 45℃;
acetic acid-[4-(3-phenyl-triazenyl)-anilide]
906715-99-9

acetic acid-[4-(3-phenyl-triazenyl)-anilide]

aniline hydrochloride
142-04-1

aniline hydrochloride

A

aniline yellow
60-09-3

aniline yellow

B

4,4'-Diaminoazobenzene
538-41-0

4,4'-Diaminoazobenzene

Conditions
ConditionsYield
With aniline anschliessend Kochen des Reaktionsproduktes mit verd. Schwefelsaeure;
triphenyl-pentaaza-1,4-diene
30616-12-7

triphenyl-pentaaza-1,4-diene

aniline hydrochloride
142-04-1

aniline hydrochloride

aniline yellow
60-09-3

aniline yellow

Conditions
ConditionsYield
With aniline at 40℃;
at 40℃;
1,4-bis-(N'-phenyl-hydrazino)-benzene
54915-74-1

1,4-bis-(N'-phenyl-hydrazino)-benzene

A

1,4-bis-(phenyl-trans-azo)-benzene
36369-22-9

1,4-bis-(phenyl-trans-azo)-benzene

B

aniline yellow
60-09-3

aniline yellow

C

aniline
62-53-3

aniline

Conditions
ConditionsYield
at 180℃;
aniline hydrochloride
142-04-1

aniline hydrochloride

sodium formate
141-53-7

sodium formate

benzene diazonium chloride
100-34-5

benzene diazonium chloride

aniline yellow
60-09-3

aniline yellow

Conditions
ConditionsYield
at 0℃;
aniline hydrochloride
142-04-1

aniline hydrochloride

benzene diazonium chloride
100-34-5

benzene diazonium chloride

aniline yellow
60-09-3

aniline yellow

Conditions
ConditionsYield
With formic acid
With hydrogenchloride
aniline hydrochloride
142-04-1

aniline hydrochloride

aniline yellow
60-09-3

aniline yellow

Conditions
ConditionsYield
With aniline at 30 - 40℃; Darstellung;
anilinium nitrate
542-15-4

anilinium nitrate

aniline yellow
60-09-3

aniline yellow

Conditions
ConditionsYield
With tin acidic sodium; water at 100℃; dann mit Natronlauge;
benzene diazonium chloride
100-34-5

benzene diazonium chloride

acetic acid
64-19-7

acetic acid

aniline
62-53-3

aniline

A

aniline yellow
60-09-3

aniline yellow

B

Phenyl azide
622-37-7

Phenyl azide

Conditions
ConditionsYield
Product distribution; verschiedene Temperaturen;
acetic acid
64-19-7

acetic acid

1,3-Diphenyltriazen
297766-64-4

1,3-Diphenyltriazen

aniline yellow
60-09-3

aniline yellow

nitrobenzene
98-95-3

nitrobenzene

1,4-phenylenediamine
106-50-3

1,4-phenylenediamine

A

aniline yellow
60-09-3

aniline yellow

B

4,4'-Diaminoazobenzene
538-41-0

4,4'-Diaminoazobenzene

Conditions
ConditionsYield
With sodium carbonate
3,4-dinitro-chlorobenzene
610-40-2

3,4-dinitro-chlorobenzene

aniline
62-53-3

aniline

A

5-chloro-2-nitro-N-phenylaniline
25781-92-4

5-chloro-2-nitro-N-phenylaniline

B

aniline yellow
60-09-3

aniline yellow

Conditions
ConditionsYield
anschl. mit HCl;
tetrachloromethane
56-23-5

tetrachloromethane

benzene diazonium chloride
100-34-5

benzene diazonium chloride

aniline
62-53-3

aniline

A

aniline yellow
60-09-3

aniline yellow

B

Phenyl azide
622-37-7

Phenyl azide

formic acid
64-18-6

formic acid

sodium formate
141-53-7

sodium formate

benzene diazonium chloride
100-34-5

benzene diazonium chloride

aniline
62-53-3

aniline

aniline yellow
60-09-3

aniline yellow

Conditions
ConditionsYield
beim Behandeln von Anilin-hydrochlorid;
benzenediazonium
2684-02-8

benzenediazonium

ethanol
64-17-5

ethanol

aniline
62-53-3

aniline

A

aniline yellow
60-09-3

aniline yellow

B

Phenyl azide
622-37-7

Phenyl azide

C

2,4,6-tribromophenol
118-79-6

2,4,6-tribromophenol

Conditions
ConditionsYield
beim Behandeln von Benzoldiazoniumperbromid;
p-benzoquinone oxime
637-62-7

p-benzoquinone oxime

aniline
62-53-3

aniline

A

azophenin
4435-12-5

azophenin

B

aniline yellow
60-09-3

aniline yellow

C

1,4-phenylenediamine
106-50-3

1,4-phenylenediamine

Conditions
ConditionsYield
at 100℃; bei der Einwirkung auf salzsaures Anilin;
N-phenyl-N'-2-naphthyl-triazene
19838-85-8

N-phenyl-N'-2-naphthyl-triazene

aniline
62-53-3

aniline

A

aniline yellow
60-09-3

aniline yellow

B

naphthalen-2-ylamine
91-59-8

naphthalen-2-ylamine

6,7-tetramethylene-1,2,3,4a,5-hexahydro-13H-benzimidazo[2,1-j]quinoline
55755-60-7

6,7-tetramethylene-1,2,3,4a,5-hexahydro-13H-benzimidazo[2,1-j]quinoline

aniline yellow
60-09-3

aniline yellow

C31H31N5
128294-29-1

C31H31N5

Conditions
ConditionsYield
With manganese(IV) oxide In benzene for 1h; Ambient temperature;100%
aniline yellow
60-09-3

aniline yellow

2,2-[60]fullerenobutanal
367926-62-3

2,2-[60]fullerenobutanal

C76H15N3

C76H15N3

Conditions
ConditionsYield
With 3 A molecular sieve In benzene at 20℃; for 48h;100%
8-quinolinol
148-24-3

8-quinolinol

4-fluorobenzaldehyde
459-57-4

4-fluorobenzaldehyde

aniline yellow
60-09-3

aniline yellow

7-{4-fluorophenyl-[4-(phenyldiazenyl)phenylamino]methyl}quinolin-8-ol
1343478-39-6

7-{4-fluorophenyl-[4-(phenyldiazenyl)phenylamino]methyl}quinolin-8-ol

Conditions
ConditionsYield
In ethanol; water at 20℃; Mannich Aminomethylation;98%
4-nitrobenzaldehdye
555-16-8

4-nitrobenzaldehdye

mercaptoacetic acid
68-11-1

mercaptoacetic acid

aniline yellow
60-09-3

aniline yellow

2-(4-nitrophenyl)-3-(4-(phenyldiazenyl)phenyl)thiazolidin-4-one

2-(4-nitrophenyl)-3-(4-(phenyldiazenyl)phenyl)thiazolidin-4-one

Conditions
ConditionsYield
With urazolium diacetate at 80℃; for 0.333333h; Catalytic behavior; Reagent/catalyst; Temperature; Green chemistry;98%
With L-proline functionalized SiO2 coated Fe3O4 nanoparticles for 0.133333h; Catalytic behavior; Reagent/catalyst; Milling; Green chemistry;98%
mercaptoacetic acid
68-11-1

mercaptoacetic acid

4-bromo-benzaldehyde
1122-91-4

4-bromo-benzaldehyde

aniline yellow
60-09-3

aniline yellow

2-(4-bromophenyl)-3-(4-(phenyldiazenyl)phenyl)thiazolidin-4-one

2-(4-bromophenyl)-3-(4-(phenyldiazenyl)phenyl)thiazolidin-4-one

Conditions
ConditionsYield
With urazolium diacetate at 80℃; for 0.25h; Green chemistry;98%
3-nitro-benzaldehyde
99-61-6

3-nitro-benzaldehyde

mercaptoacetic acid
68-11-1

mercaptoacetic acid

aniline yellow
60-09-3

aniline yellow

2-(3-nitrophenyl)-3-(4-(phenyldiazenyl)phenyl)thiazolidin-4-one

2-(3-nitrophenyl)-3-(4-(phenyldiazenyl)phenyl)thiazolidin-4-one

Conditions
ConditionsYield
With L-proline functionalized SiO2 coated Fe3O4 nanoparticles for 0.133333h; Milling; Green chemistry;98%
With urazolium diacetate at 80℃; for 0.333333h; Green chemistry;96%
bis(4-formylphenyl)hexanedioate
118677-45-5

bis(4-formylphenyl)hexanedioate

aniline yellow
60-09-3

aniline yellow

hexanediacid-bis<4-N-(4-phenylazophenyl)iminomethylphenyl>ester
134293-42-8

hexanediacid-bis<4-N-(4-phenylazophenyl)iminomethylphenyl>ester

Conditions
ConditionsYield
In toluene at 109℃; for 4h;97%
m-bromobenzoic aldehyde
3132-99-8

m-bromobenzoic aldehyde

aniline yellow
60-09-3

aniline yellow

N-(3-bromobenzylidene)-4-(phenyldiazenyl)aniline
325779-49-5

N-(3-bromobenzylidene)-4-(phenyldiazenyl)aniline

Conditions
ConditionsYield
at 110℃; for 0.0222222h; Microwave irradiation; neat (no solvent);97%
8-quinolinol
148-24-3

8-quinolinol

aniline yellow
60-09-3

aniline yellow

4-dimethylamino-benzaldehyde
100-10-7

4-dimethylamino-benzaldehyde

C30H27N5O
1343478-34-1

C30H27N5O

Conditions
ConditionsYield
In ethanol; water at 20℃; Mannich Aminomethylation;97%
8-quinolinol
148-24-3

8-quinolinol

4-hydroxy-benzaldehyde
123-08-0

4-hydroxy-benzaldehyde

aniline yellow
60-09-3

aniline yellow

7-{4-hydroxyphenyl-[4-(phenyldiazenyl)phenylamino]methyl}quinolin-8-ol
1343478-36-3

7-{4-hydroxyphenyl-[4-(phenyldiazenyl)phenylamino]methyl}quinolin-8-ol

Conditions
ConditionsYield
In ethanol; water at 20℃; Mannich Aminomethylation;97%
mercaptoacetic acid
68-11-1

mercaptoacetic acid

3-Chlorobenzaldehyde
587-04-2

3-Chlorobenzaldehyde

aniline yellow
60-09-3

aniline yellow

2-(3-chlorophenyl)-3-(4-(phenyldiazenyl)phenyl)thiazolidin-4-one

2-(3-chlorophenyl)-3-(4-(phenyldiazenyl)phenyl)thiazolidin-4-one

Conditions
ConditionsYield
With L-proline functionalized SiO2 coated Fe3O4 nanoparticles for 0.133333h; Milling; Green chemistry;97%
With urazolium diacetate at 80℃; for 0.416667h; Green chemistry;88%
m-bromobenzoic aldehyde
3132-99-8

m-bromobenzoic aldehyde

mercaptoacetic acid
68-11-1

mercaptoacetic acid

aniline yellow
60-09-3

aniline yellow

2-(3-bromophenyl)-3-(4-(phenyldiazenyl)phenyl)thiazolidin-4-one

2-(3-bromophenyl)-3-(4-(phenyldiazenyl)phenyl)thiazolidin-4-one

Conditions
ConditionsYield
With urazolium diacetate at 80℃; for 0.333333h; Green chemistry;97%
1-ferrocenylmethanol
1273-86-5

1-ferrocenylmethanol

aniline yellow
60-09-3

aniline yellow

4-{(ferrocenylmethyl)amino}azobenzene

4-{(ferrocenylmethyl)amino}azobenzene

Conditions
ConditionsYield
With KU-2 cation-exchanger In dichloromethane stirring a mixt. of ferrocenemethanol and 4-aminoazobenzene with a cation exchanger (KU-2, H form) for 4 h; addn. of ether, exchanger filtered off, solvent removed (vac.);96.5%
aniline yellow
60-09-3

aniline yellow

25,26,27-tribenzoyloxy-28-hydroxy-5,11,17-tri-(tert-butyl)calix[4]arene
180332-12-1, 872985-06-3

25,26,27-tribenzoyloxy-28-hydroxy-5,11,17-tri-(tert-butyl)calix[4]arene

25,26,27-tribenzoyloxy-28-hydroxy-5,11,17-tri-(tert-butyl)-23-(4-phenylazophenylazo)calix[4]arene
1264371-10-9

25,26,27-tribenzoyloxy-28-hydroxy-5,11,17-tri-(tert-butyl)-23-(4-phenylazophenylazo)calix[4]arene

Conditions
ConditionsYield
With hydrogenchloride; sodium acetate; sodium nitrite In methanol; water; N,N-dimethyl-formamide at 5 - 20℃;96%
8-quinolinol
148-24-3

8-quinolinol

aniline yellow
60-09-3

aniline yellow

2-nitro-benzaldehyde
552-89-6

2-nitro-benzaldehyde

C28H21N5O3
1343478-37-4

C28H21N5O3

Conditions
ConditionsYield
In ethanol; water at 20℃; Mannich Aminomethylation;96%
4-chlorobenzaldehyde
104-88-1

4-chlorobenzaldehyde

mercaptoacetic acid
68-11-1

mercaptoacetic acid

aniline yellow
60-09-3

aniline yellow

2-(4-chlorophenyl)-3-(4-(phenyldiazenyl)phenyl)thiazolidin-4-one

2-(4-chlorophenyl)-3-(4-(phenyldiazenyl)phenyl)thiazolidin-4-one

Conditions
ConditionsYield
With urazolium diacetate at 80℃; for 0.25h; Green chemistry;96%
aniline yellow
60-09-3

aniline yellow

A

aniline
62-53-3

aniline

B

1,4-phenylenediamine
106-50-3

1,4-phenylenediamine

Conditions
ConditionsYield
With formic acid; zinc In methanol at 20℃; for 0.0833333h;A 95%
B 93%
With hydrazine hydrate; aluminium In ethanol Heating;A 94%
B 93%
With ammonium acetate; zinc In methanol at 20℃; for 0.05h;A n/a
B 93%
aniline yellow
60-09-3

aniline yellow

2-Bromoacetyl bromide
598-21-0

2-Bromoacetyl bromide

p-(bromoacetamido)azobenzene
144800-02-2

p-(bromoacetamido)azobenzene

Conditions
ConditionsYield
With sodium carbonate In chloroform; water95%
2-chloro-benzaldehyde
89-98-5

2-chloro-benzaldehyde

aniline yellow
60-09-3

aniline yellow

N-(2-chlorobenzylidene)-4-(phenyldiazenyl)aniline
316137-19-6

N-(2-chlorobenzylidene)-4-(phenyldiazenyl)aniline

Conditions
ConditionsYield
at 110℃; for 0.0222222h; Microwave irradiation; neat (no solvent);95%
3-nitro-benzaldehyde
99-61-6

3-nitro-benzaldehyde

aniline yellow
60-09-3

aniline yellow

N-(3-nitrobenzylidene)-4-(phenyldiazenyl)aniline
111438-25-6

N-(3-nitrobenzylidene)-4-(phenyldiazenyl)aniline

Conditions
ConditionsYield
at 110℃; for 0.0222222h; Microwave irradiation; neat (no solvent);95%
8-quinolinol
148-24-3

8-quinolinol

4-methoxy-benzaldehyde
123-11-5

4-methoxy-benzaldehyde

aniline yellow
60-09-3

aniline yellow

C29H24N4O2
1343478-33-0

C29H24N4O2

Conditions
ConditionsYield
In ethanol; water at 20℃; Mannich Aminomethylation;95%
iron(III) chloride hexahydrate

iron(III) chloride hexahydrate

salicylaldehyde
90-02-8

salicylaldehyde

aniline yellow
60-09-3

aniline yellow

C38H28ClFeN6O2

C38H28ClFeN6O2

Conditions
ConditionsYield
Stage #1: salicylaldehyde; aniline yellow With triethylamine In ethanol
Stage #2: iron(III) chloride hexahydrate In ethanol at 20℃; for 12h; Inert atmosphere;
95%
iron(III) chloride hexahydrate

iron(III) chloride hexahydrate

salicylaldehyde
90-02-8

salicylaldehyde

aniline yellow
60-09-3

aniline yellow

C76H56Fe2N12O5

C76H56Fe2N12O5

Conditions
ConditionsYield
Stage #1: salicylaldehyde; aniline yellow With triethylamine In ethanol
Stage #2: iron(III) chloride hexahydrate In ethanol at 20℃; for 12h; Inert atmosphere;
95%
4-hydroxy-benzaldehyde
123-08-0

4-hydroxy-benzaldehyde

mercaptoacetic acid
68-11-1

mercaptoacetic acid

aniline yellow
60-09-3

aniline yellow

2-(4-hydroxyphenyl)-3-(4-(phenyldiazenyl)phenyl)thiazolidin-4-one

2-(4-hydroxyphenyl)-3-(4-(phenyldiazenyl)phenyl)thiazolidin-4-one

Conditions
ConditionsYield
With L-proline functionalized SiO2 coated Fe3O4 nanoparticles for 0.2h; Milling; Green chemistry;95%
With urazolium diacetate at 80℃; for 0.5h; Green chemistry;89%
aniline yellow
60-09-3

aniline yellow

2-cyano-N-(4-(N-(thiazol-2 yl)sulfamoyl)phenyl)acetamide
33987-99-4

2-cyano-N-(4-(N-(thiazol-2 yl)sulfamoyl)phenyl)acetamide

(E)-2-oxo-N-(4-((E)-phenyldiazenyl)phenyl)-2-((4-(N-(thiazol-2-yl)sulfamoyl)phenyl)amino)acetohydrazonoyl cyanide

(E)-2-oxo-N-(4-((E)-phenyldiazenyl)phenyl)-2-((4-(N-(thiazol-2-yl)sulfamoyl)phenyl)amino)acetohydrazonoyl cyanide

Conditions
ConditionsYield
Stage #1: aniline yellow With hydrogenchloride; sodium nitrite In water for 1h; Cooling with ice;
Stage #2: 2-cyano-N-(4-(N-(thiazol-2 yl)sulfamoyl)phenyl)acetamide With pyridine In water at 0 - 5℃;
95%
3,5-bis(methoxycarbonyl)benzoic acid
38588-64-6

3,5-bis(methoxycarbonyl)benzoic acid

aniline yellow
60-09-3

aniline yellow

dimethyl 5-((4-(phenyldiazenyl)phenyl)carbamoyl)isophthalate

dimethyl 5-((4-(phenyldiazenyl)phenyl)carbamoyl)isophthalate

Conditions
ConditionsYield
With thionyl chloride In 1-methyl-pyrrolidin-2-one at 0 - 25℃; for 6h; Inert atmosphere;94%
8-quinolinol
148-24-3

8-quinolinol

3,4-dimethoxy-benzaldehyde
120-14-9

3,4-dimethoxy-benzaldehyde

aniline yellow
60-09-3

aniline yellow

C30H26N4O3
1343478-40-9

C30H26N4O3

Conditions
ConditionsYield
In ethanol; water at 20℃; Mannich Aminomethylation;94%

4-(Phenylazo)aniline Chemical Properties

Molecule structure of 4-Aminoazobenzene (CAS NO.60-09-3) :

IUPAC Name: 4-phenyldiazenylaniline 
Molecular Weight: 197.23584 g/mol
Molecular Formula: C12H11N3 
Density: 1.12 g/cm3 
Melting Point: 127 deg C
Boiling Point: 360.7 °C at 760 mmHg 
Flash Point: 171.9 °C
Molar Volume: 174.9 cm3
Polarizability: 24.09*10-24 cm3
Surface Tension: 45.6 dyne/cm 
Enthalpy of Vaporization: 60.64 kJ/mol 
pKa Dissociation Constant: 2.82
log P (octanol-water): 3.41
Water Solubility: 32 mg/L
Henry's Law Constant: 8.70E-11 atm-m3/mole
Atmospheric OH Rate Constant: 4.34E-11 cm3/molecule-sec 
XLogP3: 3.4
H-Bond Donor: 1
H-Bond Acceptor: 3
Rotatable Bond Count: 2
Tautomer Count: 2
Exact Mass: 197.095297
MonoIsotopic Mass; 197.095297
Topological Polar Surface Area: 50.7
Heavy Atom Count: 15
Complexity: 201
Canonical SMILES: C1=CC=C(C=C1)N=NC2=CC=C(C=C2)N
InChI: InChI=1S/C12H11N3/c13-10-6-8-12(9-7-10)15-14-11-4-2-1-3-5-11/h1-9H,13H2
InChIKey: QPQKUYVSJWQSDY-UHFFFAOYSA-NEINECS: 200-453-6
Product Categories: Intermediates of Dyes and Pigments; Solvent Dyestuff

4-(Phenylazo)aniline Uses

 4-Aminoazobenzene (CAS NO.60-09-3) is used as dye intermediates. And it is used for the synthesis of azo dyes, disperse dyes, oxazine dyes; also used in the system paints and pigments, as well as alcohol-soluble yellow and pH indicator.

4-(Phenylazo)aniline Production

Inputs phenlyaniline and sodium nitrite solution to the reactor, at 30-40 °C stirring, at 2.5-3h to add 30% hydrochloric acid, then heated to 50-55 °C for translocation.

4-(Phenylazo)aniline Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 200mg/kg (200mg/kg)   National Technical Information Service. Vol. AD277-689,

4-(Phenylazo)aniline Safety Profile

Hazard Codes: ToxicT, DangerousN, IrritantXi
Risk Statements: 45-50/53
R45: May cause cancer
R50/53: Very toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment
Safety Statements: 53-45-60-61
S53: Avoid exposure - obtain special instructions before use 
S45: In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible) 
S60: This material and its container must be disposed of as hazardous waste 
S61: Avoid release to the environment. Refer to special instructions / safety data sheets
RIDADR: UN 3077 9/PG 3
WGK Germany: 3
RTECS: BY8225000
Hazardous Substances Data: 60-09-3(Hazardous Substances Data)

4-(Phenylazo)aniline Specification

 4-Aminoazobenzene (CAS NO.60-09-3) is also called 4-(Phenylazo)aniline ; 4-(Phenylazo)benzenamine ; 4-Amino-1,1'-azobenzene ; 4-Aminoazobenzol ; 4-Benzeneazoaniline ; Aminoazobenzene ; Aniline Yellow ; Aniline, p-(phenylazo)- ; Azobenzene, 4-amino- ; Benzenamine, 4-(phenylazo)- ; Brasilazina Oil Yellow G . 4-Aminoazobenzene (CAS NO.60-09-3) is odorless brownish-yellow needles with bluish coating, or an orange powder. It is insoluble in water and soluble in ethanol, ether, chloroform, benzene and oil. Dust may form an explosive mixture in air. 4-Aminoazobenzene can detonate, particularly if sensitized by the presence of metal salts or strong acids. May form toxic gases with acids, aldehydes, amides, carbamates, cyanides, inorganic fluorides, halogenated organics, isocyanates, ketones, metals, nitrides, peroxides, phenols, epoxides, acyl halides, and strong oxidizing or reducing agents. May form flammable gases with alkali metals. May react explosively with strong oxidizing agents, metal salts, peroxides, and sulfides. Emits toxic fumes of oxides of nitrogen when heated to decomposition (over 350 °C) . Flash point data for 4-Aminoazobenzenecan are not available; however, 4-Aminoazobenzenecan is probably combustible.

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