60-09-3

Basic information

• Product Name: 4-AMINOAZOBENZENE
• Synonyms: 4-Aminoazobenzene,CI 11000;4-Aminoazobenzol;AAB;Aniline yellow,CI 11000;Aniline, p-(phenylazo)-;Azobenzene, 4-amino-;Brasilazina Oil Yellow G;C.I. Solvent Blue 7
• CAS NO: 60-09-3
• Molecular Formula: C₁₂H₁₁N₃
• Molecular Weight: 197.24
• EINECS: 200-453-6
• Product Categories: Intermediates of Dyes and Pigments;Solvent Dyestuff
• Mol File: 60-09-3.mol
• Article Data: 41

Chemical Properties

• Melting Point: 123-126 °C(lit.)
• Boiling Point: >360 °C(lit.)
• Flash Point: 171.9 °C
• Appearance: powder
• Density: 1.2828 (rough estimate)
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.6500 (estimate)
• PKA: 2.82(at 25℃)
• Water Solubility: 29.59mg/L(25 oC)
• Stability: Stable. Incompatible with strong oxidizing agents.
• Merck: 14,419
• BRN: 1913042
• CAS DataBase Reference: 4-AMINOAZOBENZENE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-AMINOAZOBENZENE(60-09-3)
• EPA Substance Registry System: 4-AMINOAZOBENZENE(60-09-3)

Safety Data

• Hazard Codes: T,N,Xi
• Statements: 45-50/53-36/37/38-20/21/22-46
• Safety Statements: 53-45-60-61-36/37/39-26-22
• RIDADR: UN 3077 9/PG 3
• WGK Germany: 3
• RTECS: BY8225000
• HazardClass: IRRITANT
• PackingGroup: III
• Hazardous Substances Data: 60-09-3(Hazardous Substances Data)

Usage

Description

This azoic coloring can be reduced in paraphenylenediamine (PPD). It ean be found in some semipermanent hair dyes, and patch tests are frequently positive (about 30%) in hairdressers with hand dermatitis. Because of cross-sensitivity, the detection of sensitization to p-aminoazobenzene may be assumed by a PPD test.

Chemical Properties

Different sources of media describe the Chemical Properties of 60-09-3 differently. You can refer to the following data:
1. 4-Aminoazobenzene forms yellow to tan crystals or orange needles.
2. powder

Uses

Different sources of media describe the Uses of 60-09-3 differently. You can refer to the following data:
1. In form of its salts in dyeing; intermediate in manufacture of Acid Yellow, diazo dyes and indulines.
2. as a dye for lacquer, varnish, wax products, oi! stains and styrene res ins; in insecticides; used as an intermediate in the manufacture of Acid Yellow, diazo dyes and indulines.

Preparation

commonly known as Aniline Yellow. (a) aniline?hydrochloride solution added to a aniline?diazonium salt, and slowly, until aniline?diazonium salt salt disappear so far. Then in contain a small amount of aniline?hydrochloride aniline?solution will product (Diazoaminobenzene) 30 ~ 40 ℃ heating 2 ~ 3 hours,??acidified to form 4-(Phenyldiazenyl)benzenamine??hydrochloride and crystalline precipitates. In order to obtain 4-(Phenyldiazenyl)benzenamine?times the company, and then 4-(Phenyldiazenyl)benzenamine hydrochloride dissolved in water and mercerized. (B) aniline?diazotization and coupling anilino-methanesulfonic acid, sodium hydroxide solution and then with boiled together, hydrolyzed mesylate.

Definition

ChEBI: Azobenzene substituted at one of the 4-positions by an amino group.

General Description

Odorless brownish-yellow needles with bluish coating, or an orange powder.

Air & Water Reactions

Dust may form an explosive mixture in air. Insoluble in water.

Reactivity Profile

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) [Sax, 2nd ed., 1965, p. 417].

Hazard

Possible carcinogen.

Fire Hazard

Flash point data for 4-AMINOAZOBENZENE are not available; however, 4-AMINOAZOBENZENE is probably combustible.

Contact allergens

This azoic coloring can be reduced in para-phenylenediamine (PPD). It can be found in some semi-permanent hair dyes and patch tests are frequently positive (about 30%) in hairdressers with hand dermatitis. Because of hydrolysis of the azo bond, the detection of sensitization to p-aminoazobenzene may be assumed by a PPD test.

Safety Profile

Confirmed carcinogen with experimental neoplastigenic and tumorigenic data. Poison by intraperitoneal route. An experimental teratogen. Mutation data reported. Used as a dye for lacquer, varnish, wax products, oil stains, and styrene resins. When heated to decomposition it emits toxic fumes of NOx. See also AMINES

Potential Exposure

An azo compound used in form of salts in dyeing; used as intermediate in manufacture of acid yellow and diazo dyes; in insecticides, waxes, lacquers, varnishes, stains, styrene resins

Shipping

UN2811 Toxic solids, organic, n.o.s., Hazard Class: 6.1; Labels: 6.1-Poisonous materials, Technical Name Required. UN3143 Dyes, solid, toxic, n.o.s. or Dye intermediates, solid, toxic, n.o.s., Hazard Class: 6.1; Labels: 6.1-Poisonous materials, Technical Name Required

Properties and Applications

green light yellow to red light yellow. Melting point is 127.5 ℃, its hydrochloride for blue crystal. Soluble in ethanol, slightly soluble in water for yellow. In concentrated sulfuric acid for brown, red after diluted solution; In hydrochloric acid solution for red, boil color disappear. Used for alcohol soluble paint, varnish, paraffin wax, oil, synthetic resin coloring. Standard Light Fastness Heat-resistant(℃) Water Sodium Carbonate(5%) Hydrochloric acid(5%) Melting point Stable ISO Good 125 140 Good Good Good

Standard

Light Fastness

Melting point

Stable

ISO

Good

Purification Methods

Crystallise this dye from EtOH, CCl4, pet ether/*C6H6, or a MeOH/H2O mixture. [Beilstein 16 IV 445.]

Incompatibilities

Dust may form explosive mixture with air. Azo compounds can detonate. This applies in particular to organic azides that have been sensitized by the addition of metal salts or strong acids. Toxic gases are formed by mixing materials of this class 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. Flammable gases are formed by mixing materials in this group with alkali metals. Explosive combination can occur with strong oxidizing agents, metal salts, peroxides, and sulfides. This chemicalis sensitive to prolonged exposure to heat. This chemical is incompatible with strong oxidizing agents

InChI:InChI=1/C12H11N3/c13-10-6-8-12(9-7-10)15-14-11-4-2-1-3-5-11/h1-9H,13H2

Synthetic route

1,3-Diphenyltriazen (297766-64-4) → aniline yellow (60-09-3)

Conditions	Yield
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) → aniline yellow (60-09-3)

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

aniline (62-53-3) → aniline yellow (60-09-3)

Conditions	Yield
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) → aniline yellow (60-09-3) + 2-aminoazobenzene (2835-58-7)

Conditions	Yield
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 (62-53-3) → aniline yellow (60-09-3)

Conditions	Yield
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) → aniline yellow (60-09-3) + 4-nitrohydrazobenzene (34139-26-9)

Conditions	Yield
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 (62-53-3) + 1,3-Diphenyltriazen (297766-64-4) → aniline yellow (60-09-3)

Conditions	Yield
at 40 - 45℃; for 1h; Inert atmosphere;	62%

o-toluidine (95-53-4) + 1,3-Diphenyltriazen (297766-64-4) → aniline yellow (60-09-3) + 2-methyl-4-phenylazo-aniline (1142-13-8)

Conditions	Yield
With K10-montmorillonite at 20℃; for 6h; Product distribution; Addition;	A 5% B 42%

p-toluidine (106-49-0) + 1,3-Diphenyltriazen (297766-64-4) → aniline yellow (60-09-3) + 4-methyl-2-phenylazoaniline (313485-86-8)

Conditions	Yield
With K10-montmorillonite at 20℃; for 6h; Product distribution; Addition;	A 21% B 36%

N,N-diethyl-4-phenylazoaniline N-oxide (108193-68-6) → aniline yellow (60-09-3) + N-ethyl-4-aminoazobenzene (2058-67-5) + 4-(diethylamino)azobenzene (2481-94-9)

Conditions	Yield
In benzene at 17℃; for 5h; Irradiation;	A 23% B 10% C 28%

quinoline (91-22-5) + quinoline hydrochloride (530-64-3) + 1,3-Diphenyltriazen (297766-64-4) → aniline yellow (60-09-3)

Conditions	Yield
at 40 - 50℃;

formic acid (64-18-6) + aniline hydrochloride (142-04-1) + benzene diazonium chloride (100-34-5) → aniline yellow (60-09-3)

Conditions	Yield
at 0℃;

ethanol (64-17-5) + 1,5-diphenyl-3-methylpentazene (41798-82-7) + aniline hydrochloride (142-04-1) → aniline yellow (60-09-3)

aniline hydrochloride (142-04-1) + 4-benzenesulfonylamino-benzenediazonium-betaine (36071-24-6) → N-phenylsulfonyl-1,4-phenylenediamine (5466-91-1) + aniline yellow (60-09-3)

Conditions	Yield
With aniline at 45℃;

acetic acid-[4-(3-phenyl-triazenyl)-anilide] (906715-99-9) + aniline hydrochloride (142-04-1) → aniline yellow (60-09-3) + 4,4'-Diaminoazobenzene (538-41-0)

Conditions	Yield
With aniline anschliessend Kochen des Reaktionsproduktes mit verd. Schwefelsaeure;

triphenyl-pentaaza-1,4-diene (30616-12-7) + aniline hydrochloride (142-04-1) → aniline yellow (60-09-3)

Conditions	Yield
With aniline at 40℃;
at 40℃;

1,4-bis-(N'-phenyl-hydrazino)-benzene (54915-74-1) → 1,4-bis-(phenyl-trans-azo)-benzene (36369-22-9) + aniline yellow (60-09-3) + aniline (62-53-3)

Conditions	Yield
at 180℃;

aniline hydrochloride (142-04-1) + sodium formate (141-53-7) + benzene diazonium chloride (100-34-5) → aniline yellow (60-09-3)

Conditions	Yield
at 0℃;

aniline hydrochloride (142-04-1) + benzene diazonium chloride (100-34-5) → aniline yellow (60-09-3)

Conditions	Yield
With formic acid
With hydrogenchloride

aniline hydrochloride (142-04-1) → aniline yellow (60-09-3)

Conditions	Yield
With aniline at 30 - 40℃; Darstellung;

anilinium nitrate (542-15-4) → aniline yellow (60-09-3)

Conditions	Yield
With tin acidic sodium; water at 100℃; dann mit Natronlauge;

benzene diazonium chloride (100-34-5) + acetic acid (64-19-7) + aniline (62-53-3) → aniline yellow (60-09-3) + Phenyl azide (622-37-7)

Conditions	Yield
Product distribution; verschiedene Temperaturen;

acetic acid (64-19-7) + 1,3-Diphenyltriazen (297766-64-4) → aniline yellow (60-09-3)

nitrobenzene (98-95-3) + 1,4-phenylenediamine (106-50-3) → aniline yellow (60-09-3) + 4,4'-Diaminoazobenzene (538-41-0)

Conditions	Yield
With sodium carbonate

3,4-dinitro-chlorobenzene (610-40-2) + aniline (62-53-3) → 5-chloro-2-nitro-N-phenylaniline (25781-92-4) + aniline yellow (60-09-3)

Conditions	Yield
anschl. mit HCl;

tetrachloromethane (56-23-5) + benzene diazonium chloride (100-34-5) + aniline (62-53-3) → aniline yellow (60-09-3) + Phenyl azide (622-37-7)

formic acid (64-18-6) + sodium formate (141-53-7) + benzene diazonium chloride (100-34-5) + aniline (62-53-3) → aniline yellow (60-09-3)

Conditions	Yield
beim Behandeln von Anilin-hydrochlorid;

benzenediazonium (2684-02-8) + ethanol (64-17-5) + aniline (62-53-3) → aniline yellow (60-09-3) + Phenyl azide (622-37-7) + 2,4,6-tribromophenol (118-79-6)

Conditions	Yield
beim Behandeln von Benzoldiazoniumperbromid;

p-benzoquinone oxime (637-62-7) + aniline (62-53-3) → azophenin (4435-12-5) + aniline yellow (60-09-3) + 1,4-phenylenediamine (106-50-3)

Conditions	Yield
at 100℃; bei der Einwirkung auf salzsaures Anilin;

N-phenyl-N'-2-naphthyl-triazene (19838-85-8) + aniline (62-53-3) → aniline yellow (60-09-3) + naphthalen-2-ylamine (91-59-8)

6,7-tetramethylene-1,2,3,4a,5-hexahydro-13H-benzimidazo[2,1-j]quinoline (55755-60-7) + aniline yellow (60-09-3) → C31H31N5 (128294-29-1)

Conditions	Yield
With manganese(IV) oxide In benzene for 1h; Ambient temperature;	100%

aniline yellow (60-09-3) + 2,2-[60]fullerenobutanal (367926-62-3) → C76H15N3

Conditions	Yield
With 3 A molecular sieve In benzene at 20℃; for 48h;	100%

8-quinolinol (148-24-3) + 4-fluorobenzaldehyde (459-57-4) + aniline yellow (60-09-3) → 7-{4-fluorophenyl-[4-(phenyldiazenyl)phenylamino]methyl}quinolin-8-ol (1343478-39-6)

Conditions	Yield
In ethanol; water at 20℃; Mannich Aminomethylation;	98%

4-nitrobenzaldehdye (555-16-8) + mercaptoacetic acid (68-11-1) + aniline yellow (60-09-3) → 2-(4-nitrophenyl)-3-(4-(phenyldiazenyl)phenyl)thiazolidin-4-one

Conditions	Yield
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) + 4-bromo-benzaldehyde (1122-91-4) + aniline yellow (60-09-3) → 2-(4-bromophenyl)-3-(4-(phenyldiazenyl)phenyl)thiazolidin-4-one

Conditions	Yield
With urazolium diacetate at 80℃; for 0.25h; Green chemistry;	98%

3-nitro-benzaldehyde (99-61-6) + mercaptoacetic acid (68-11-1) + aniline yellow (60-09-3) → 2-(3-nitrophenyl)-3-(4-(phenyldiazenyl)phenyl)thiazolidin-4-one

Conditions	Yield
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) + aniline yellow (60-09-3) → hexanediacid-bis<4-N-(4-phenylazophenyl)iminomethylphenyl>ester (134293-42-8)

Conditions	Yield
In toluene at 109℃; for 4h;	97%

m-bromobenzoic aldehyde (3132-99-8) + aniline yellow (60-09-3) → N-(3-bromobenzylidene)-4-(phenyldiazenyl)aniline (325779-49-5)

Conditions	Yield
at 110℃; for 0.0222222h; Microwave irradiation; neat (no solvent);	97%

8-quinolinol (148-24-3) + aniline yellow (60-09-3) + 4-dimethylamino-benzaldehyde (100-10-7) → C30H27N5O (1343478-34-1)

Conditions	Yield
In ethanol; water at 20℃; Mannich Aminomethylation;	97%

8-quinolinol (148-24-3) + 4-hydroxy-benzaldehyde (123-08-0) + aniline yellow (60-09-3) → 7-{4-hydroxyphenyl-[4-(phenyldiazenyl)phenylamino]methyl}quinolin-8-ol (1343478-36-3)

Conditions	Yield
In ethanol; water at 20℃; Mannich Aminomethylation;	97%

mercaptoacetic acid (68-11-1) + 3-Chlorobenzaldehyde (587-04-2) + aniline yellow (60-09-3) → 2-(3-chlorophenyl)-3-(4-(phenyldiazenyl)phenyl)thiazolidin-4-one

Conditions	Yield
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) + mercaptoacetic acid (68-11-1) + aniline yellow (60-09-3) → 2-(3-bromophenyl)-3-(4-(phenyldiazenyl)phenyl)thiazolidin-4-one

Conditions	Yield
With urazolium diacetate at 80℃; for 0.333333h; Green chemistry;	97%

1-ferrocenylmethanol (1273-86-5) + aniline yellow (60-09-3) → 4-{(ferrocenylmethyl)amino}azobenzene

Conditions	Yield
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) + 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)-23-(4-phenylazophenylazo)calix[4]arene (1264371-10-9)

Conditions	Yield
With hydrogenchloride; sodium acetate; sodium nitrite In methanol; water; N,N-dimethyl-formamide at 5 - 20℃;	96%

8-quinolinol (148-24-3) + aniline yellow (60-09-3) + 2-nitro-benzaldehyde (552-89-6) → C28H21N5O3 (1343478-37-4)

Conditions	Yield
In ethanol; water at 20℃; Mannich Aminomethylation;	96%

4-chlorobenzaldehyde (104-88-1) + mercaptoacetic acid (68-11-1) + aniline yellow (60-09-3) → 2-(4-chlorophenyl)-3-(4-(phenyldiazenyl)phenyl)thiazolidin-4-one

Conditions	Yield
With urazolium diacetate at 80℃; for 0.25h; Green chemistry;	96%

aniline yellow (60-09-3) → aniline (62-53-3) + 1,4-phenylenediamine (106-50-3)

Conditions	Yield
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) + 2-Bromoacetyl bromide (598-21-0) → p-(bromoacetamido)azobenzene (144800-02-2)

Conditions	Yield
With sodium carbonate In chloroform; water	95%

2-chloro-benzaldehyde (89-98-5) + aniline yellow (60-09-3) → N-(2-chlorobenzylidene)-4-(phenyldiazenyl)aniline (316137-19-6)

Conditions	Yield
at 110℃; for 0.0222222h; Microwave irradiation; neat (no solvent);	95%

3-nitro-benzaldehyde (99-61-6) + aniline yellow (60-09-3) → N-(3-nitrobenzylidene)-4-(phenyldiazenyl)aniline (111438-25-6)

Conditions	Yield
at 110℃; for 0.0222222h; Microwave irradiation; neat (no solvent);	95%

8-quinolinol (148-24-3) + 4-methoxy-benzaldehyde (123-11-5) + aniline yellow (60-09-3) → C29H24N4O2 (1343478-33-0)

Conditions	Yield
In ethanol; water at 20℃; Mannich Aminomethylation;	95%

iron(III) chloride hexahydrate + salicylaldehyde (90-02-8) + aniline yellow (60-09-3) → C38H28ClFeN6O2

Conditions	Yield
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 + salicylaldehyde (90-02-8) + aniline yellow (60-09-3) → C76H56Fe2N12O5

Conditions	Yield
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) + mercaptoacetic acid (68-11-1) + aniline yellow (60-09-3) → 2-(4-hydroxyphenyl)-3-(4-(phenyldiazenyl)phenyl)thiazolidin-4-one

Conditions	Yield
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) + 2-cyano-N-(4-(N-(thiazol-2 yl)sulfamoyl)phenyl)acetamide (33987-99-4) → (E)-2-oxo-N-(4-((E)-phenyldiazenyl)phenyl)-2-((4-(N-(thiazol-2-yl)sulfamoyl)phenyl)amino)acetohydrazonoyl cyanide

Conditions	Yield
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) + aniline yellow (60-09-3) → dimethyl 5-((4-(phenyldiazenyl)phenyl)carbamoyl)isophthalate

Conditions	Yield
With thionyl chloride In 1-methyl-pyrrolidin-2-one at 0 - 25℃; for 6h; Inert atmosphere;	94%

8-quinolinol (148-24-3) + 3,4-dimethoxy-benzaldehyde (120-14-9) + aniline yellow (60-09-3) → C30H26N4O3 (1343478-40-9)

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

Upstream product

• 142-04-1 aniline hydrochloride 
• 36071-24-6 4-benzenesulfonylamino-benzenediazonium-betaine 
• 141-53-7 sodium formate 
• 100-34-5 benzene diazonium chloride 
• 542-15-4 anilinium nitrate 
• 56-23-5 tetrachloromethane 
• 62-53-3 aniline 
• 64-18-6 formic acid 
• 2684-02-8 benzenediazonium 
• 64-17-5 ethanol 
• 622-74-2 N-phenyl-N'-p-tolyl-triazene 
• 95633-07-1 4-(phenyl-ONN-azoxy)aniline 
• 110490-31-8 2-(3-phenyl-triazenyl)-benzoic acid methyl ester 
• 4504-08-9 p-nitrophenyl-N,N,O-azoxybenzene 

Downstream Products

• 5422-79-7 N-(4-phenylazo-phenyl)-maleamic acid 
• 16435-01-1 4-((((E)-4-((E)-phenyldiazenyl)phenyl)imino)methyl)phenol 
• 744-66-1 N-(p-methoxybenzylidene)-p-aminoazobenzene 
• 16434-74-5 2-((4-(phenyldiazenyl)phenylimino)methyl)phenol 
• 2058-67-5 N-ethyl-4-aminoazobenzene 
• 655-86-7 2,3-diaminephenazine 
• 1161-45-1 1,4-bis-phenylazo-benzene 
• 73112-88-6 4,4'-bis(phenylazo)azobenzene 
• 3403-03-0 2-thioxo-thiazolidine-4,5-dione 5-[(4-phenylazo-phenyl)-hydrazone] 
• 41374-63-4 N-(p-Benzolazo-phenyl)-oxamidsaeure-ethylester 
• 100884-91-1 N-(2-Nitro-ethyl)-4-amino-azobenzol 
• 121968-19-2 1-(p-Benzolazo-phenylamino)-7-(p-benzolazo-phenylimino)-cyclohepta-1,3,5-trien 
• 65874-13-7 5-(2-chloro-phenyl)-3-(4-phenylazo-anilinomethyl)-3H-[1,3,4]oxadiazole-2-thione 
• 4308-02-5 phenyl-[4-phenyl-2-(4-phenylazo-anilino)-thiazol-5-yl]-methanone 

Relevant articles and documents

Solvent effects and energy transfer processes in luminescent composite

The combination of conjugated polymers and photochromic molecules can result in a composite, which can yield a new photoresponsive material. The efficiency of these materials is due to the process of energy transfer. In this work, the conjugated polymer poly (3-hexylthiophene-co-1,4-phenylene) (PTPh) was synthesized by Suzuki route and the photochromic molecule 4-aminoazobenzene (Azo), synthesized by diazonium salt coupling, were mixed forming a luminescent composite. This new material was obtained in four different solvents, in order to evaluate its influence. When the Azo is added in a solution of PTPh, it was observed a decrease of the emission spectra of the copolymer, indicating the suppression of PTPh due to F?ster's energy transfer from PTPh to Azo. The larger energy transfer has been found in ethanol. Density Functional Theory (DFT) calculations have been performed for Azo, an oligomeric model for the PTPh and a complex formed by the Azo and the oligomeric model for PTPh, with two different functionals. Computational results indicate the occurrence of C-H---π and N-H---S interactions in the optimized structure of PTPh/Azo complex. The LUMO orbital of the PTPh/Azo complex is mainly located in the Azo moiety, suggesting that Azo might receive energy from the polymer. Therefore, the joint computational-experimental study enables the understanding of the energy transfer that takes place in the PTPh/Azo systems.

Synthesis and experimental investigations on the photoconductivity of p-aminoazobenzene based non-conjugated polybenzoxazine system

In this paper, we report the study of a novel p-aminoazobenzene based non-conjugated, benzoxazine polymer, poly([4-(6-tert-butyl-4H-benzo[e][1,3]oxazin-3-yl)phenyl]-phenyldiazene) (AZO-PBZ) synthesized using solvent free, thermally activated cationic ring opening polymerization. The thermal, photophysical, electrochemical, and photoconducting properties of the polymer were investigated. The optical absorption band edges of AZO-PBZ thin film was observed at 555 nm. Photoinduced charge transfer nature of AZO-PBZ was studied by analyzing the fluorescence spectra and performing photoconductivity experiments. Incorporation of [6, 6]-phenyl-C61-butyric acid methyl ester denoted as PCBM into the polymer leads to quenching of the fluorescent intensity and exhibits significant photoconductivity. The photocurrent through the PCBM blend films was measured as a function of electric field to recognize the field dependence on carrier generation. Internal photocurrent efficiency of the polymer:PCBM blend samples was found to be in the order of 10?5 and photoconductive sensitivity was of the order of 10?11 S W?1cm, which is adequate for photorefractivity.

Cannabinoid receptor light-operated ligand and preparation method and application thereof

The invention relates to the technical field of biology, in particular to a novel cannabinoid receptor light-operated ligand and a preparation method and application thereof. Disclosed is the cannabinoid receptor light-operated ligand or the isomer prodrug, the solvate and the pharmaceutically acceptable salt of the cannabinoid receptor light-operated ligand, wherein the structural formula of thecannabinoid receptor light-operated ligand is A-linker-B; A is a transmembrane domain ligand structure, and B is a light-operated element; Linker is a subunit which is linear and has no activity on acannabinoid receptor light-operated ligand. According to the invention, the cannabinoid receptor ligand is integrated with azobenzene through a proper connector, so that the ligand configuration is changed under an illumination condition, and the activation or inhibition state of the cannabinoid receptor is regulated and controlled.

Photoreversible formation of nanotubes in water from an amphiphilic azobenzene derivative

An anionic azobenzene-appended derivative ofl-ValylGlycine self-assembles into nanotubes in water. Irradiation with 365 nm light provokestrans-cisisomerization of the azobenzene unit and subsequent tube disassembly. Thermal or photoinduced (457 nm light)

Synthesis method of p-phenylenediamine

The invention relates to a synthesis method of p-phenylenediamine, and belongs to the technical field of organic material preparation. Aniline adopted as a raw material undergoes a diazotization reaction and a heating rearrangement reaction to generate 4-aminoazobenzene, a proper amount of an acid is added, and the 4-aminoazobenzene is separated out; the 4-aminoazobenzene is dissolved in a propersolvent, a catalyst is added, the p-phenylenediamine product is obtained through a hydrogenation reduction reaction, filtration and reduced pressure distillation, and aniline is recovered as a byproduct and can be recycled as the raw material. Compared with an existing p-phenylenediamine production method, the method of the invention has the advantages of safe and environmentally-friendly preparation process, little emission of three wastes, easily available reaction raw materials, simple reaction steps, and high purity of the finally prepared product, so the method has good industrial implementation prospects.