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| CAS No.: | 1689-82-3 |
|---|---|
| Name: | 4-PHENYLAZOPHENOL |
| Article Data: | 135 |
| Molecular Structure: | |
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| Formula: | C12H10N2O |
| Molecular Weight: | 198.224 |
| Synonyms: | C.I.Solvent Yellow 7 (7CI,8CI);Phenol, 4-(phenylazo)- (9CI);Phenol, p-phenylazo-(5CI);4-(Phenylazo)phenol;4-(Phenyldiazenyl)phenol;p-Hydroxyazobenzene;p-(Phenylazo)phenol;C.I. 11800;NSC 3177;4-(Phenylhydrazinylidene)cyclohexa-2,5-dien-1-one; |
| EINECS: | 216-880-6 |
| Density: | 1.13 g/cm3 |
| Melting Point: | 150-152 °C(lit.) |
| Boiling Point: | 369.812 °C at 760 mmHg |
| Flash Point: | 233.646 °C |
| Solubility: | Soluble in alcohol, ether, dilute alkali solution and concentrated sulfuric acid, slightly soluble in hot water, insoluble in water |
| Appearance: | Orange columnar solid |
| Hazard Symbols: |
 Xi
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| Risk Codes: | 36/37/38 |
| Safety: | 26-36 |
| PSA: | 44.95000 |
| LogP: | 3.80760 |
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Consensus Reports
IARC Cancer Review: Group 3 IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 7 , 1987,p. 56.(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) ; Animal Inadequate Evidence IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 8 , 1975,p. 157.(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) . Reported in EPA TSCA Inventory.
Specification
The 4-Hydroxyazobenzene with CAS registry number of 1689-82-3 is also known as Phenol,4-(2-phenyldiazenyl)-. The IUPAC name is 4-(Phenylhydrazinylidene)cyclohexa-2,5-dien-1-one. Its EINECS registry number is 216-880-6. In addition, the formula is C12H10N2O and the molecular weight is 198.22. This chemical is a orange columnar solid and should be sealed in cool, dry place away from oxidants or alkali. Besides, it is soluble in alcohol, ether, dilute alkali solution and concentrated sulfuric acid, slightly soluble in hot water, insoluble in water.
Physical properties about 4-Hydroxyazobenzene are: (1)ACD/LogP: 3.23; (2)ACD/LogD (pH 5.5): 3; (3)ACD/LogD (pH 7.4): 3; (4)ACD/BCF (pH 5.5): 171; (5)ACD/BCF (pH 7.4): 166; (6)ACD/KOC (pH 5.5): 1378; (7)ACD/KOC (pH 7.4): 1339; (8)#H bond acceptors: 3; (9)#H bond donors: 1; (10)#Freely Rotating Bonds: 3; (11)Index of Refraction: 1.596; (12)Molar Refractivity: 59.709 cm3; (13)Molar Volume: 175.445 cm3; (14)Surface Tension: 44.548 dyne/cm; (15)Density: 1.13 g/cm3; (16)Flash Point: 233.646 °C; (17)Enthalpy of Vaporization: 64.086 kJ/mol; (18)Boiling Point: 369.812 °C at 760 mmHg.
Preparation of 4-Hydroxyazobenzene: it is prepared by diazotization, coupling reaction of aniline. Firstly, aniline and sodium nitrite solution are added to reactor under stirring at the temperature of 5 °C when hydrochloric acid and crushed ice have been added. Secondly, slowly adding the reacion solution to phenol sodium salt solution with crushed ice under stirring. After feeding, the solution is continuely stirred for 15 minutes at the temperature below 15 °C. At last, product is obtained by centrifugation, washing and drying.
Uses of 4-Hydroxyazobenzene: it can be used as organic synthesis intermediate and indicator. For example, it is used to produce (4-chloro-phenyl)-phenyl-diazene. The reaction occurs with reagent POCl3 and solvent dimethylformamide with other condition of heating for 5 hours. The yield is about 80%.
When you are using this chemical, please be cautious about it. As a chemical, it is irritating to eyes, respiratory system and skin. During using it, wear suitable protective clothing. If contact with eyes accidently, rinse immediately with plenty of water and seek medical advice.
You can still convert the following datas into molecular structure:
1. Canonical SMILES: C1=CC=C(C=C1)NN=C2C=CC(=O)C=C2
2. InChI: InChI=1S/C12H10N2O/c15-12-8-6-11(7-9-12)14-13-10-4-2-1-3-5-10/h1-9,13H
3. InChIKey: JTSBGMZPPPULTA-UHFFFAOYSA-N
The toxicity data is as follows:
| Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
|---|---|---|---|---|---|
| mouse | LD50 | intraperitoneal | 75mg/kg (75mg/kg) | National Technical Information Service. Vol. AD691-490, | |
| mouse | LDLo | oral | 800mg/kg (800mg/kg) | Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. Vol. 60, Pg. 209, 1964. |