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122-37-2

Basic Information
CAS No.: 122-37-2
Name: Phenol,4-(phenylamino)-
Article Data: 68
Cas Database
Molecular Structure:
Molecular Structure of 122-37-2 (Phenol,4-(phenylamino)-)
Formula: C12H11NO
Molecular Weight: 185.225
Synonyms: Phenol,p-anilino- (8CI);4-(Phenylamino)phenol;4-Anilinophenol;N-(4-Hydroxyphenyl)aniline;N-Phenyl-p-aminophenol;NSC1543;VTI 1;VTI 1 (phenol);p-(Phenylamino)phenol;p-Anilinophenol;p-Hydroxydiphenylamine;p-Hydroxyldiphenylamine;p-Oxydiphenylamine;
EINECS: 204-538-9
Density: 1.203 g/cm3
Melting Point: 69 - 72 °C
Boiling Point: 330.7 °C at 760 mmHg
Flash Point: 146.2 °C
Solubility: soluble in alcohol, ether, acetone, chloroform and benzene, slightly soluble in water, dilute alkali and inorganic acids
Appearance: The common product is reddish brown casting body and the refined products is orange
Hazard Symbols: HarmfulXn
Risk Codes: 37/38-41-22
Safety: 26-36/37/39-36/39
Transport Information: UN 2811
PSA: 32.26000
LogP: 3.20880
Synthetic route
945-51-7

1,1'-sulfinylbisbenzene

123-30-8

4-amino-phenol

122-37-2

4-anilinophenol

Conditions
ConditionsYield
With SingaCycle-A1; sodium t-butanolate In tetrahydrofuran at 60℃; for 6h; Inert atmosphere; regioselective reaction;98%
100-02-7

4-nitro-phenol

591-50-4

iodobenzene

122-37-2

4-anilinophenol

Conditions
ConditionsYield
With sodium tetrahydroborate at 120℃; for 4h;97%
2406-04-4

4-(phenylimino)cyclohexa-2,5-dienone

122-37-2

4-anilinophenol

Conditions
ConditionsYield
With triethylsilane; palladium diacetate In 2,2,2-trifluoroethanol at 20℃; for 0.333333h;95%
With 2,5-bis(1,1-dimethylethyl)-1,4-benzenediol; trichloroacetic acid In chlorobenzene at 25.05℃; Kinetics; Further Variations:; Reagents;
With N,N'-diphenyl-1,4-phenylenediamine In chlorobenzene at 68.45℃; Equilibrium constant; Thermodynamic data; Further Variations:; Temperatures;
591-50-4

iodobenzene

123-30-8

4-amino-phenol

122-37-2

4-anilinophenol

Conditions
ConditionsYield
With 0.068 mol% Ni(II) and 0.026 mol% Pd(II) complexed in pyridine grafted demetalated chlorophyll b co-polymer modified SiO2 shell on Fe3O4 core at 120℃; for 2.6h;95%
With potassium phosphate; copper(l) iodide In N,N-dimethyl-formamide at 80℃; for 16h; Inert atmosphere;64%
108-86-1

bromobenzene

123-30-8

4-amino-phenol

122-37-2

4-anilinophenol

Conditions
ConditionsYield
With chloro[2-(dicyclohexylphosphino)-3,6-dimethoxy-2',4',6'-triisopropyl-1,1'-biphenyl][2-(2-aminoethyl)phenyl]palladium(ll); sodium t-butanolate In 1,4-dioxane at 110℃; for 1h; Inert atmosphere;92%
With 0.068 mol% Ni(II) and 0.026 mol% Pd(II) complexed in pyridine grafted demetalated chlorophyll b co-polymer modified SiO2 shell on Fe3O4 core at 120℃; for 3h;92%
With chloro[2-(dicyclohexylphosphino)-3 ,6-dimethoxy-2’,4’, 6’-triisopropyl- 1,1’-biphenyl] [2-(2-aminoethyl)phenyl]palladium(II); sodium t-butanolate In 1,4-dioxane at 90℃; for 2h; Buchwald-Hartwig Coupling; Inert atmosphere;82.37%
With copper(l) iodide
13515-47-4

4-(phenylamino)phenyl acetate

122-37-2

4-anilinophenol

Conditions
ConditionsYield
With potassium carbonate In methanol at 20℃; for 4h;92%
540-38-5

4-Iodophenol

98-95-3

nitrobenzene

122-37-2

4-anilinophenol

Conditions
ConditionsYield
With sodium tetrahydroborate at 120℃; for 6.5h;92%
108-86-1

bromobenzene

100-02-7

4-nitro-phenol

122-37-2

4-anilinophenol

Conditions
ConditionsYield
With sodium tetrahydroborate at 120℃; for 4.5h;92%
101-02-0

triphenyl phosphite

122-37-2

4-anilinophenol

Conditions
ConditionsYield
With aniline; hydroquinone In water91%
540-38-5

4-Iodophenol

62-53-3

aniline

122-37-2

4-anilinophenol

Conditions
ConditionsYield
With copper(l) iodide; C12H13N3O; triethylamine In diethylene glycol dimethyl ether at 30℃; for 15h; Sealed tube;90%
With 0.068 mol% Ni(II) and 0.026 mol% Pd(II) complexed in pyridine grafted demetalated chlorophyll b co-polymer modified SiO2 shell on Fe3O4 core at 120℃; for 5h;90%
With potassium phosphate; copper(l) iodide; N',N'-diphenyl-1H-pyrrole-2-carbohydrazide In diethylene glycol at 20℃; Sealed tube;84%
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Consensus Reports

Reported in EPA TSCA Inventory.

Specification

The IUPAC name of this chemical is 4-anilinophenol. With the CAS registry number 122-37-2 and EINECS 204-538-9, it is also named as 4-Hydroxydiphenylamine. The product's category is Anilines, Aromatic Amines and Nitro Compounds. The common product is reddish brown casting body and the refined products is orange. It is soluble in alcohol, ether, acetone, chloroform and benzene, slightly soluble in water, dilute alkali and inorganic acids. What's more, this chemical can be obtained by the reaction of aniline and paradioxybenzene. When heated to decomposition it emits toxic fumes of NOx. So the storage environment should be well-ventilated, low-temperature and dry. Keep p-Anilinophenol separate from raw materials of food.

The other characteristics of this product can be summarized as: (1)ACD/LogP: 2.82; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2.82; (4)ACD/LogD (pH 7.4): 2.82; (5)ACD/BCF (pH 5.5): 82.3; (6)ACD/BCF (pH 7.4): 82.16; (7)ACD/KOC (pH 5.5): 817.81; (8)ACD/KOC (pH 7.4): 816.4; (9)#H bond acceptors: 2; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 3; (12)Polar Surface Area: 32.26 Å2; (13)Index of Refraction: 1.67; (14)Molar Refractivity: 57.5 cm3; (15)Molar Volume: 153.9 cm3; (16)Surface Tension: 53.1 dyne/cm; (17)Enthalpy of Vaporization: 59.6 kJ/mol; (18)Vapour Pressure: 8.52E-05 mmHg at 25°C; (19)Rotatable Bond Count: 2; (20)Tautomer Count: 4; (21)Exact Mass: 185.084064; (22)MonoIsotopic Mass: 185.084064; (23)Topological Polar Surface Area: 32.3; (24)Heavy Atom Count: 14; (25)Complexity: 158.

Uses of p-Anilinophenol: It is used as intermediate in medicine, dye, pesticide and rubber additives. It also can react with iodoethane to get (4-ethoxy-phenyl)-phenyl-amine. This reaction needs reagent 10percent potassium hydroxyde and solvent ethanol. The yield is 52%.

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 respiratory system and skin. And it has risk of serious damage to the eyes. 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.

People can use the following data to convert to the molecule structure. 
1. Smiles:c1(Nc2ccccc2)ccc(O)cc1
2. InChI:InChI=1/C12H11NO/c14-12-8-6-11(7-9-12)13-10-4-2-1-3-5-10/h1-9,13-14H

The following are the toxicity data which has been tested.

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mammal (species unspecified) LD50 oral 3300mg/kg (3300mg/kg) LUNGS, THORAX, OR RESPIRATION: CYANOSIS Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 40(10), Pg. 114, 1975.
mouse LD50 intraperitoneal 200mg/kg (200mg/kg) LUNGS, THORAX, OR RESPIRATION: CYANOSIS

BLOOD: METHEMOGLOBINEMIA-CARBOXYHEMOGLOBIN
National Technical Information Service. Vol. OTS0571980,
mouse LD50 intravenous 60mg/kg (60mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 12, Pg. 1123, 1962.
mouse LD50 oral 1600mg/kg (1600mg/kg) LUNGS, THORAX, OR RESPIRATION: CYANOSIS

BLOOD: METHEMOGLOBINEMIA-CARBOXYHEMOGLOBIN
National Technical Information Service. Vol. OTS0571980,
rat LD50 intraperitoneal 200mg/kg (200mg/kg) LUNGS, THORAX, OR RESPIRATION: CYANOSIS

BLOOD: METHEMOGLOBINEMIA-CARBOXYHEMOGLOBIN
National Technical Information Service. Vol. OTS0571980,
rat LD50 oral 3300mg/kg (3300mg/kg) AUTONOMIC NERVOUS SYSTEM: OTHER (DIRECT) PARASYMPATHOMIMETIC

BEHAVIORAL: GENERAL ANESTHETIC

BLOOD: METHEMOGLOBINEMIA-CARBOXYHEMOGLOBIN
Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 27(3), Pg. 52, 1983.