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o-Phenetidine

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o-Phenetidine

EINECS 202-356-4
CAS No. 94-70-2 Density 1.051 g/cm3
PSA 35.25000 LogP 2.24870
Solubility water: 0.5-1.0 g/100 mL at 24.5 °C Melting Point -20 °C
Formula C8H11NO Boiling Point 231.9 °C at 760 mmHg
Molecular Weight 137.181 Flash Point 99.2 °C
Transport Information UN 2311 6.1/PG 3 Appearance deep red liquid
Safety 28-36/37-45-28A Risk Codes 23/24/25-33
Molecular Structure Molecular Structure of 94-70-2 (o-Phenetidine) Hazard Symbols ToxicT,IrritantXi
Synonyms

o-Phenetidine(7CI,8CI);2-Aminophenetole;2-Ethoxyaniline;2-Ethoxybenzenamine;2-Ethoxyphenylamine;NSC 9818;o-Ethoxyaniline;

Article Data 45

o-Phenetidine Consensus Reports

Reported in EPA TSCA Inventory.

o-Phenetidine Specification

The IUPAC name of o-Phenetidine is 2-ethoxyaniline. With the CAS registry number 94-70-2, it is also named as 1-Amino-2-ethoxybenzene; 2-Ethoxybenzenamine. It is deep red liquid which is slightly soluble in water. Furthermore, this chemical is very sensitive to exposure to light and air. It neutralizes acids in exothermic reactions to form salts plus water. Flammable gaseous hydrogen may be generated in combination with strong reducing agents, such as hydrides. 

The other characteristics of this product can be summarized as: (1)ACD/LogP: 1.62; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.58; (4)ACD/LogD (pH 7.4): 1.62; (5)ACD/BCF (pH 5.5): 9.22; (6)ACD/KOC (pH 5.5): 166.28; (7)ACD/KOC (pH 7.4): 181.89; (8)#H bond acceptors: 2; (9)#H bond donors: 2; (10)#Freely Rotating Bonds: 3; (11)Index of Refraction: 1.544; (12)Molar Refractivity: 41.8 cm3; (13)Molar Volume: 132.2 cm3; (14)Polarizability: 16.57×10-24 cm3; (15)Surface Tension: 38.5 dyne/cm; (16)Enthalpy of Vaporization: 46.86 kJ/mol; (17)Vapour Pressure: 0.0608 mmHg at 25°C; (18)Rotatable Bond Count: 2; (19)Exact Mass: 137.084064; (20)MonoIsotopic Mass: 137.084064; (21)Topological Polar Surface Area: 35.2; (22)Heavy Atom Count: 10.

Preparation of o-Phenetidine: It can be obtained by 2-nitro-phenetole with reagent H2 and catalytic agent Pd.

Uses of o-Phenetidine: It is used as a dye, perfume, pharmaceutical intermediates. It is also used in organic synthesis. For example: It can react with nicotinonitrile to get N-(2-ethoxy-phenyl)-nicotinamidine. This reaction needs reagent Fe(NO3)3*9H2O, liq. NH3/powd. sodium and solvent diethyl ether. The reaction time is 3 hours. The yield is 70%.

When you are using this chemical, please be cautious about it as the following:
It is toxic by inhalation, in contact with skin and if swallowed. After contact with skin, wash immediately with plenty of soap-suds. If you want to contact this product, you must wear suitable protective clothing and gloves. In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)

People can use the following data to convert to the molecule structure.
1. Smiles: c1(c(cccc1)N)OCC;
2. InChI: InChI=1/C8H11NO/c1-2-10-8-6-4-3-5-7(8)9/h3-6H,2,9H2,1H3.

The following are the toxicity data which has been tested.

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LDLo oral 600mg/kg (600mg/kg)   Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. Vol. 52, Pg. 215, 1956.
rabbit LD50 oral 600mg/kg (600mg/kg)   Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. Vol. 52, Pg. 215, 1956.

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