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Basic Information
CAS No.: 139-59-3
Name: 4-Phenoxyaniline
Article Data: 92
Molecular Structure:
Molecular Structure of 139-59-3 (4-Phenoxyaniline)
Formula: C12H11NO
Molecular Weight: 185.225
Synonyms: Aniline,p-phenoxy- (6CI,7CI,8CI);4-(Phenyloxy)aniline;4-Amino-1-phenoxybenzene;4-Aminodiphenyl ether;4-Aminophenyl phenyl ether;4-Phenoxybenzenamine;4-Phenoxyphenylamine;NSC 4629;NSC 57084;NSC 61131;p-Aminophenyl phenyl ether;p-Phenoxyaniline;p-Phenoxyphenylamine;
EINECS: 205-367-2
Density: 1.141 g/cm3
Melting Point: 82-84 °C(lit.)
Boiling Point: 320 °C at 760 mmHg
Flash Point: 155.8 °C
Solubility: < 1 g/L (20 °C) in water
Appearance: brown to green-brown crystalline flakes or powder
Hazard Symbols: HarmfulXn, IrritantXi
Risk Codes: 22-36/37/38-43-68-50/53
Safety: 26-36/37/39-61-45-24
PSA: 35.25000
LogP: 3.64230
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Standards and Recommendations

Handling: Wash thoroughly after handling. Do not allow water to get into the container because of violent reaction. Avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and eyes.
Storage: Store in a cool, dry place. Store in a tightly closed container.

Specification

The IUPAC name of this chemical is 4-phenoxyaniline. With the CAS registry number 139-59-3, it is also named as 4-Aminodiphenyl ether. The product's categories are Intermediates of Dyes and Pigments; API Intermediates. It is brown to green-brown crystalline flakes or powder.

The other characteristics of this product can be summarized as: (1)ACD/LogP: 2.36; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2.29; (4)ACD/LogD (pH 7.4): 2.36; (5)ACD/BCF (pH 5.5): 31.1; (6)ACD/BCF (pH 7.4): 36.53; (7)ACD/KOC (pH 5.5): 389.05; (8)ACD/KOC (pH 7.4): 456.95; (9)#H bond acceptors: 2; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 3; (12)Index of Refraction: 1.618; (13)Molar Refractivity: 56.93 cm3; (14)Molar Volume: 162.3 cm3; (15)Polarizability: 22.56×10-24 cm3; (16)Surface Tension: 46.6 dyne/cm; (17)Enthalpy of Vaporization: 56.16 kJ/mol; (18)Vapour Pressure: 0.000327 mmHg at 25°C; (19)Rotatable Bond Count: 2; (20)Exact Mass: 185.084064; (21)MonoIsotopic Mass: 185.084064; (22)Topological Polar Surface Area: 35.2; (23)Heavy Atom Count: 14; (24)Complexity: 158.

Preparation of p-Phenoxyaniline: It can be obtained by (4-nitro-phenyl)-phenyl ether. This reaction needs reagent hydrazine monohydrate, catalyzer graphite powder (325 mesh) and solvent ethanol by heating. The reaction time is 2 hours. The yield is 87%.

Uses of p-Phenoxyaniline: It can be used as intermediate of pharmaceutical and dye. It also can react with chloroacetyl chloride to get chloro-acetic acid-(4-phenoxy-anilide). This reaction needs reagent pyridine and acetone.

When you are using this chemical, please be cautious about it as the following:
It is not only harmful if swallowed, but also irritating to eyes, respiratory system and skin. So people should avoid contact with skin. And it is very toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. If you want to contact this product, you must wear suitable protective clothing, gloves and eye/face protection. In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) In addition, it should be avoided release to the environment.  

People can use the following data to convert to the molecule structure.
1. SMILES:O(c1ccccc1)c2ccc(cc2)N
2. InChI:InChI=1/C12H11NO/c13-10-6-8-12(9-7-10)14-11-4-2-1-3-5-11/h1-9H,13H2