60-09-3 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
Check Digit Verification of cas no
The CAS Registry Mumber 60-09-3 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 6 and 0 respectively; the second part has 2 digits, 0 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 60-09:
(4*6)+(3*0)+(2*0)+(1*9)=33
33 % 10 = 3
So 60-09-3 is a valid CAS Registry Number.
InChI:InChI=1/C12H11N3/c13-10-6-8-12(9-7-10)15-14-11-4-2-1-3-5-11/h1-9H,13H2
60-09-3Relevant articles and documents
Solvent effects and energy transfer processes in luminescent composite
Menandro, Alessandra S.,Oliveira, Hueder P. M.,Péres, Laura O.,Siqueira, Leonardo J. A.
, (2020)
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
Pillai, Jisha J.,Abbas, Anshad,Narayanan, Sona,Sreekumar,Kartha, C. Sudha,Joseph, Rani
, p. 330 - 337 (2018)
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
-
Paragraph 0066; 0073; 0106-0112, (2021/01/24)
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
Angulo-Pachón, César A.,Galindo, Francisco,Miravet, Juan F.,Navarro-Barreda, Diego
supporting information, p. 11545 - 11548 (2021/11/12)
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)