621-66-9

Basic information

• Product Name: 4-(phenylazo)-o-cresol
• Synonyms: 4-(phenylazo)-o-cresol;2-Methyl-4-(phenylazo)phenol;C.I.11840;C.I.Solvent Yellow 10;Oil Yellow WP
• CAS NO: 621-66-9
• Molecular Formula: C₁₃H₁₂N₂O
• Molecular Weight: 212.24718
• EINECS: 210-699-6
• Mol File: 621-66-9.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 338.1°C at 760 mmHg
• Flash Point: 158.3°C
• Appearance: /
• Density: 1.11g/cm³
• Vapor Pressure: 0.0001mmHg at 25°C
• Refractive Index: 1.587
• CAS DataBase Reference: 4-(phenylazo)-o-cresol(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(phenylazo)-o-cresol(621-66-9)
• EPA Substance Registry System: 4-(phenylazo)-o-cresol(621-66-9)

Safety Data

• Hazardous Substances Data: 621-66-9(Hazardous Substances Data)

Usage

Preparation

aniline diazotization, and o-Cresol coupling.

Properties and Applications

green light yellow to red yellow. Soluble in hot water for red light yellow, soluble in ethanol for green yellow. In ethanol from out of the crystallization product melting point is 126 ~ 128 ℃. In concentrated sulfuric acid for yellow brown, dilution after brick red solution; In hot concentrated hydrochloric acid in orange brown precipitation; In the heat of 2% sodium hydroxide solution for yellow orange. Used for oil, paraffin wax, cellulose paint color. Standard Light Fastness Heat-resistant(℃) water Sodium Carbonate(5%) Hydrochloric acid(5%) Melting point Stable ISO General 126～128 70≥170 Sublimation Well Well Well

Standard

Light Fastness

Melting point

Stable

ISO

General

Purification Methods

Crystallise the phenol from hexane or pet ether (m 130o). [Beilstein 16 II 59, 16 III 104, 16 IV 193.]

InChI:InChI=1/C13H12N2O/c1-10-9-12(7-8-13(10)16)15-14-11-5-3-2-4-6-11/h2-9,14H,1H3/b15-12-

Upstream product

• 2362-14-3 4,4'-cyclohexylidenedi-o-cresol 
• 100-34-5 benzene diazonium chloride 
• 2684-02-8 benzenediazonium 
• 95-48-7 ortho-cresol 
• 369-57-3 benzenediazonium tetrafluoroborate 
• 2467-25-6 bis(4-hydroxy-3-methylphenyl)methane 
• 7664-93-9 sulfuric acid 
• 62-53-3 aniline 

Downstream Products

• 101280-35-7 (2-methyl-4-phenylazo-phenoxy)-acetic acid methyl ester 
• 2835-96-3 4-amino-2-methylphenol 
• 1435-63-8 2-Methyl-4-(4-nitro-phenylazo)-phenol 
• 62-53-3 aniline 
• 100969-60-6 (2-methyl-4-phenylazo-phenoxy)-acetic acid 

Relevant articles and documents

Asymmetric azobenzene capable of solid-liquid conversion and preparation method of asymmetric azobenzene

The invention discloses asymmetric azobenzene capable of solid-liquid conversion and a preparation method of the asymmetric azobenzene. The structural formula of the asymmetric azobenzene capable of solid-liquid conversion prepared by the method is shown in the specification, wherein n is 2, 6 or 12; R is -CH3,-CH2CH3,-OCH3 or -OCH2CH3. The method is simple in reaction, simple and convenient to operate and high in yield. And the asymmetric azobenzene capable of solid-liquid conversion can realize solid-liquid conversion under the conditions of heating and ultraviolet lamp irradiation or pure heating, and has a certain application value.

Are two azo groups better than one? Investigating the photoresponse of polymer-bisazobenzene complexes

Azobenzene chromophores are an ideal choice for material applications where functionality needs to be activated in a precise remote-controlled fashion. The azobenzene stimuli-response falls into two categories, either based on efficient trans-to-cis photoisomerization and a high cis yield enabling on-off type functions, or relying on a fast trans-cis-trans cycling creating motion in the material system. Herein, we show that using bisazochromophores instead of the more common monoazobenzene derivatives makes a difference in the performance of light-responsive azopolymers, more specifically in photo-orientation and all-optical surface patterning. Our findings point out that polymer-bisazobenzene complexes are an attractive alternative as high-performance photoreponsive materials and that although their properties are highly sensitive to the extent of conjugation in the system, they can be designed into relatively transparent films with high performance for all-optical patterning.

MECHANISM OF AZO COUPLING. VI. REACTIONS OF THE p-NITROBENZENEDIAZONIUM ION WITH (PHENYLAZO)PHENOL AND ITS DERIVATIVES

According to the results of elemental analysis, high-performance liquid chromatography, and NMR, UV, and IR spectroscopy the preparatively isolated products of the reactions of the p-nitrobenzenediazonium ion with p-(phenylazo)phenol and its derivatives are derivatives of 4,4-bis(p-nitrophenylazo)-2,5-cyclohexadien-1-one.The products are stable in the solid state and in neutral media.In acid and alkaline media they are split with the formation of the nitrobenzenediazonium ion and the corresponding p-(phenylazo)phenols.The product with a cyclohexadienone structure is regarded as a model of the second of the two successively formed intermediate complexes in the azo coupling.