14869-39-7

Basic information

• Product Name: 2'-ETHOXYACETOPHENONE
• Synonyms: 2-Ethoxy-1-phenylethanone;AURORA 22085;AKOS BBS-00006696;1-(2-ETHOXYPHENYL)ETHANONE;2-ACETYLPHENETOLE;2'-ETHOXYACETOPHENONE;2-ETHOXYACETOPHENONE;O-ETHOXY ACETOPHENONE
• CAS NO: 14869-39-7
• Molecular Formula: C₁₀H₁₂O₂
• Molecular Weight: 164.2
• Mol File: 14869-39-7.mol
• Article Data: 18

Chemical Properties

• Melting Point: 36-40 °C(lit.)
• Boiling Point: 243-244°C
• Flash Point: >230 °F
• Appearance: /
• Density: 1.0036
• Refractive Index: 1.5070 (estimate)
• CAS DataBase Reference: 2'-ETHOXYACETOPHENONE(CAS DataBase Reference)
• NIST Chemistry Reference: 2'-ETHOXYACETOPHENONE(14869-39-7)
• EPA Substance Registry System: 2'-ETHOXYACETOPHENONE(14869-39-7)

Safety Data

• Hazard Codes: Xi,T
• Statements: 22-26-36/37/38
• Safety Statements: 26-28-36/37-45
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 14869-39-7(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Journal of the American Chemical Society, 72, p. 5161, 1950 DOI: 10.1021/ja01167a100

Upstream product

• 62957-60-2 2-ethoxyacetonitrile 
• 64-17-5 ethanol 
• 3282-32-4 2-diazo-acetophenone 
• 4279-03-2 ethoxymethylmagnesium chloride 
• 100-47-0 benzonitrile 
• 13735-81-4 1-styrenyloxytrimethylsilane 
• 3188-13-4 ethyl chloromethyl ether 
• 611-74-5 N,N-dimethylbenzamide 
• 6175-45-7 2,2-diethoxyacetophenone 
• 16883-69-5 N-phenacylpyridinium bromide 
• 100-52-7 benzaldehyde 
• 22383-53-5 2-ethoxy-1-phenylethanol 
• 120-46-7 1,3-diphenylpropanedione 
• 122-51-0 orthoformic acid triethyl ester 

Downstream Products

• 137039-84-0 3-Ethoxy-2-phenyl-2-trimethylsilanyloxy-propionitrile 
• 64015-68-5 (2-ethoxyphenyl)glyoxal 
• 6175-45-7 2,2-diethoxyacetophenone 
• 137040-12-1 3-Ethoxy-2-hydroxy-2-phenyl-propionic acid 1-aza-bicyclo[2.2.2]oct-3-yl ester 
• 137040-05-2 3-Ethoxy-2-hydroxy-2-phenyl-propionic acid ethyl ester 
• 137039-91-9 3-Ethoxy-2-hydroxy-2-phenyl-propionamide 
• 137039-98-6 3-Ethoxy-2-hydroxy-2-phenyl-propionic acid 
• 94261-37-7 (+/-)-1-Aethoxy-5-N,N-diaethylamino-4-methyl-2-phenyl-pent-3-en-2-ol 
• 51179-79-4 2-((Z)-4-methoxy-6-methyl-7,8-dihydro-6H-[1,3]dioxolo[4,5-g]isoquinolin-5-ylidene)-1-phenyl-ethanone 
• 83463-84-7 3-ethoxy-4-methyl-2-phenylquinoline 
• 79598-11-1 2-Brom-2-ethoxy-1,3-diphenyl-propan-1,3-dion 
• 79597-99-2 2-Ethoxy-1,3-diphenyl-propan-1,3-dion 
• 79597-88-9 2-Ethoxy-1-hydroxy-1,3-diphenyl-1-propen-2-on 

Relevant articles and documents

Lithiomethyl ethyl ether from chloromethyl ethyl ether via a DTBB-catalysed lithiation

The reaction of equimolar amounts of chloromethyl ethyl ether (1) and a carbonyl compound [Bu(n)CHO, Bu(t)CHO, PhCHO, Pr(i)2CO, Bu(t)2CO, (CH2)4CO, 2-cyclohexenone, PhCOMe] with an excess of lithium powder (1:7 molar ratio) and a catalytic amount of DTBB (5 mol%) in THF at 0°C (Method A) leads, after hydrolysis, to the corresponding hydroxyethers 2. The reaction can be also carried out in a two-step process: tandem lithiation at -90°C and reaction with the electrophile [Bu(n)CHO,(CH2)4CO, PhCOMe, PhMe2SiCl, CO2, PhCN, PhCONMe2, CyNCO, PhN=CHPh] at -90 to -60°C (Method B).

Regioselective Vinylation of Remote Unactivated C(sp3)?H Bonds: Access to Complex Fluoroalkylated Alkenes

Regioselective incorporation of a particular functional group into aliphatic sites by direct activation of unreactive C?H bonds is of great synthetic value. Despite advances in radical-mediated functionalization of C(sp3)?H bonds by a hydrogen-atom transfer process, the site-selective vinylation of remote C(sp3)?H bonds still remains underexplored. Reported herein is a new protocol for the regioselective vinylation of unactivated C(sp3)?H bonds. The remote C(sp3)?H activation is promoted by a C-centered radical instead of the commonly used N and O radicals. The reaction possesses high product diversity and synthetic efficiency, furnishing a plethora of synthetically valuable E alkenes bearing tri-/di-/mono-fluoromethyl and perfluoroalkyl groups.

Direct Synthesis of α-Alkoxy Ketones by Oxidative C–O Bond Formation

A convenient method to prepare α-alkoxy ketones has been developed by oxidative coupling of aryl methyl ketones and alcohols. With aqueous tert-butyl hydroperoxide (6.0 equiv.) as the oxidant, tetrabutylammonium iodide (20 mol-%) as the catalyst, and TsNHNH2(1.0 equiv.) as the additive, ketones underwent direct alkoxylation to give α-methoxy or α-ethoxy ketones in moderate to good yields.