94-70-2

Basic information

• Product Name: o-Phenetidine
• Synonyms: Phthalhydroquinone-d4;Phthalic Alcoho-d4l;Pyrocatechin-d4;Pyrocatechol-d4;2-Aminophenetole 2-Ethoxyaniline;O-PHENETIDINE FOR SYNTHESIS 250 ML;o-Phenetidine >=97.0% (GC);Benzenamine,2-ethoxy-
• CAS NO: 94-70-2
• Molecular Formula: C₈H₁₁NO
• Molecular Weight: 137.18
• EINECS: 202-356-4
• Mol File: 94-70-2.mol
• Article Data: 18

Chemical Properties

• Melting Point: -20 °C
• Boiling Point: 231-233 °C(lit.)
• Flash Point: 177 °F
• Appearance: Deep red/Liquid
• Density: 1.051 g/mL at 25 °C(lit.)
• Vapor Pressure: 1 mm Hg ( 67 °C)
• Refractive Index: n20/D 1.555(lit.)
• Storage Temp.: Store at +15°C to +25°C.
• Solubility: 7g/l
• PKA: 4.43(at 28℃)
• Water Solubility: 0.5-1.0 g/100 mL at 24.5 ºC
• Merck: 14,7227
• BRN: 637069
• CAS DataBase Reference: o-Phenetidine(CAS DataBase Reference)
• NIST Chemistry Reference: o-Phenetidine(94-70-2)
• EPA Substance Registry System: o-Phenetidine(94-70-2)

Safety Data

• Hazard Codes: T,Xi
• Statements: 23/24/25-33
• Safety Statements: 28-36/37-45-28A
• RIDADR: UN 2311 6.1/PG 3
• WGK Germany: 2
• RTECS: SI6465300
• F: 8-10-23
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 94-70-2(Hazardous Substances Data)

Usage

Description

o-Phenetidine, also known as 2-phenylethylamine, is a substituted aniline and an aromatic ether with a reddish-brown oily liquid appearance. It is primarily used in the manufacture of acetophenetidin.

Uses

Used in Pharmaceutical Industry:
o-Phenetidine is used as an intermediate in the synthesis of various pharmaceutical compounds, particularly in the production of acetophenetidin. It plays a crucial role in the development of medications that target specific health conditions.
Used in Chemical Synthesis:
o-Phenetidine is utilized as a building block in the synthesis of various organic compounds and dyes. Its unique chemical structure allows it to be a versatile component in the creation of a wide range of chemical products.
Used in Research and Development:
o-Phenetidine serves as a valuable compound in scientific research and development, particularly in the study of substituted aniline and aromatic ether chemistry. It aids researchers in understanding the properties and potential applications of related compounds.

Preparation

o-Phenetidine is produced from 2- ethoxynitrobenzene by reduction with iron or by catalytic hydrogenation in the presence of precious-metal catalysts or Raney nickel.

Air & Water Reactions

o-Phenetidine is very sensitive to exposure to light and air. . Slightly soluble in water.

Reactivity Profile

o-Phenetidine neutralizes acids in exothermic reactions to form salts plus water. May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen may be generated in combination with strong reducing agents, such as hydrides.

Fire Hazard

o-Phenetidine is probably combustible.

InChI:InChI=1/C8H11NO/c1-2-10-8-6-4-3-5-7(8)9/h3-6H,2,9H2,1H3

Upstream product

• 123162-07-2 (2-Ethoxy-phenyl)-carbamic acid 2-morpholin-4-yl-ethyl ester 
• 7647-01-0 hydrogenchloride 
• 100-65-2 N-Phenylhydroxylamine 
• 17672-29-6 (2-ethoxyphenyl)hydrazine 
• 610-67-3 1-ethoxy-2-nitrobenzene 
• 103-73-1 Phenetole 
• 614-80-2 2-(acetylamino)phenol 
• 95-55-6 2-amino-phenol 
• 74-96-4 ethyl bromide 
• 103976-26-7 2-[(2-ethoxyphenylamino)methylene]malonic acid diethyl ester 
• 824-39-5 sodium o-nitrophenate 
• 824-38-4 potassium 2-nitrophenoxide 
• 88-75-5 2-hydroxynitrobenzene 
• 7664-93-9 sulfuric acid 

Downstream Products

• 78987-73-2 N,N-bis-(2-hydroxy-ethyl)-o-phenetidine 
• 41687-09-6 N-(2-ethoxyphenyl)-3-oxobutanamide 
• 42473-85-8 N-(2-ethoxy-phenyl)-phthalimide 
• 116594-77-5 N-o-phenetidinomethyl-phthalimide 
• 80260-84-0 acridin-9-yl-(2-ethoxy-phenyl)-amine 
• 41449-16-5 2-(2-ethoxy-phenyl)-4-nitro-isoindoline-1,3-dione 
• 3691-93-8 2-hydroxy-dibenzofuran-3-carboxylic acid o-phenetidide 
• 132649-40-2 2-(2-ethoxy-phenyl)-4,5,6,7-tetrachloro-isoindoline-1,3-dione 
• 581-08-8 2'-ethoxyacetanilide 

Relevant articles and documents

Superior activity and selectivity of heterogenized cobalt catalysts for hydrogenation of nitroarenes

The development of improved catalysts for highly selective hydrogenation of nitroarenes is described. For this purpose Co nanoparticles were supported on ordered mesoporous carbon CMK-3 and characterized in detail. The optimal CMK-3-CoPc catalyst exhibits excellent hydrogenation activity for several (hetero)aromatic nitro compounds and yielded the corresponding anilines under mild conditions (40 °C, 20 bar H2).

Investigation of hydro-lipophilic properties of n-alkoxyphenylhydroxynaphthalenecarboxamides ?

The evaluation of the lipophilic characteristics of biologically active agents is indispensable for the rational design of ADMET-tailored structure–activity models. N-Alkoxy-3-hydroxynaphthalene-2-carboxanilides, N-alkoxy-1-hydroxynaphthalene-2-carboxanilides, and N-alkoxy-2-hydroxynaphthalene-1-carboxanilides were recently reported as a series of compounds with antimycobacterial, antibacterial, and herbicidal activity. As it was found that the lipophilicity of these biologically active agents determines their activity, the hydro-lipophilic properties of all three series were investigated in this study. All 57 anilides were analyzed using the reversed-phase high-performance liquid chromatography method for the measurement of lipophilicity. The procedure was performed under isocratic conditions with methanol as an organic modifier in the mobile phase using an end-capped non-polar C18 stationary reversed-phase column. In the present study, a range of software lipophilicity predictors for the estimation of clogP values of a set of N-alkoxyphenylhydroxynaphthalenecarboxamides was employed and subsequently cross-compared with experimental parameters. Thus, the empirical values of lipophilicity (logk) and the distributive parameters (π) were compared with the corresponding in silico characteristics that were calculated using alternative methods for deducing the lipophilic features. To scrutinize (dis)similarities between the derivatives, a PCA procedure was applied to visualize the major differences in the performance of molecules with respect to their lipophilic profile, molecular weight, and violations of Lipinski’s Rule of Five.

Fe-Catalyzed Amination of (Hetero)Arenes with a Redox-Active Aminating Reagent under Mild Conditions

A novel and efficient Fe-catalyzed direct C?H amination (NH2) of arenes is reported using a new redox-active aminating reagent. The reaction is simple, and can be performed under air, mild, and redox-neutral conditions. This protocol has a broad substrate scope and could be used in the late-stage modification of bioactive compounds. Mechanistic studies demonstrate that a radical pathway could be involved in this transformation.