15547-89-4

Basic information

• Product Name: 2-(3-METHOXYPHENYL)CYCLOHEXANONE
• Synonyms: 2-(3-METHOXYPHENYL)CYCLOHEXANONE;2-(3-METHOXYPHENYL)CYCLOHEXANONE, TECH., 90%;2-(3-Methoxyphenyl)cyclohexanone, tech.,90%;2-(3-Methoxyphenyl)cyclohexanone,90%,tech.;2-(3-Methoxyphenyl)cyclohexanone technical grade, 90%;2-(3-METHOXYPHENYL)CYCLOHEXANON;2-(3-methoxyphenyl)cyclohexan-1-one
• CAS NO: 15547-89-4
• Molecular Formula: C₁₃H₁₆O₂
• Molecular Weight: 204.26
• EINECS: 239-602-5
• Product Categories: C13 to C14;Carbonyl Compounds;Ketones
• Mol File: 15547-89-4.mol
• Article Data: 17

Chemical Properties

• Boiling Point: 140-142°C 0,2mm
• Flash Point: >230 °F
• Appearance: /
• Density: 1.1 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.000144mmHg at 25°C
• Refractive Index: n20/D 1.546(lit.)
• CAS DataBase Reference: 2-(3-METHOXYPHENYL)CYCLOHEXANONE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(3-METHOXYPHENYL)CYCLOHEXANONE(15547-89-4)
• EPA Substance Registry System: 2-(3-METHOXYPHENYL)CYCLOHEXANONE(15547-89-4)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• Hazardous Substances Data: 15547-89-4(Hazardous Substances Data)

Usage

Chemical Properties

clear colorless liquid

Uses

2-(3-Methoxyphenyl)cyclohexanone may be used as starting reagent for the synthesis of octahydrophenanthrene, an important intermediate in the synthesis of morphinans. It may be used in the synthesis of 2-methyl-5-phenyl morphan.

Synthesis Reference(s)

The Journal of Organic Chemistry, 20, p. 1197, 1955 DOI: 10.1021/jo01126a008

General Description

2-(3-Methoxyphenyl)cyclohexanone is an aromatic ketone. It is a clear, colorless liquid. 2-(3-Methoxyphenyl)cyclohexanone is reported to participate in the synthesis of 9-azamorphinan.

InChI:InChI=1/C13H16O2/c1-15-11-6-4-5-10(9-11)12-7-2-3-8-13(12)14/h4-6,9,12H,2-3,7-8H2,1H3/t12-/m0/s1

Upstream product

• 36282-40-3 (3-methoxyphenyl)magnesium bromide 
• 822-87-7 2-Chlorocyclohexanone 
• 2398-37-0 3-methoxyphenyl bromide 
• 108-94-1 cyclohexanone 
• 10365-98-7 3-methoxyphenylboronic acid 
• 766-85-8 3-methoxy-1-iodobenzene 
• 286-20-4 cyclohexane-1,2-epoxide 
• 768-66-1 2,2,6,6-tetramethyl-piperidine 
• 766-51-8 2-Chloroanisole 
• 31600-88-1 m-methoxyphenyllithium 
• 2562-37-0 1-nitrocyclohexene 
• 6651-36-1 1-(Trimethylsilyloxy)cyclohexene 
• 21300-30-1 lithium 1-cyclohexenolate 
• 100-66-3 methoxybenzene 

Downstream Products

• 1172637-92-1 2-(3-Methoxy-phenyl)-2-propyl-cyclohexanone 
• 440090-07-3 2-(3-methoxyphenyl)-2,3,4,5-tetradihydrooxepine 
• 440089-99-6 7-(3,4-dimethoxyphenyl)oxepan-2-one 
• 19626-25-6 2-(3-methoxyphenyl)-2-ethoxycarbonylmethylcyclohexanone 
• 1884-40-8 6-(3-methoxyphenyl)-6-oxohexanoic acid 
• 53661-21-5 2-(2-dimethylamino-ethyl)-2-(3-methoxy-phenyl)-cyclohexanone 
• 76778-38-6 2-ethyl-2-(3-methoxyphenyl)cyclohexanone 

Relevant articles and documents

PREPARATION AND REACTIVITY OF λ6-VERATROLEMANGANESE TRICARBONYL TETRAFLUOROBORATE

Reaction of pentacarbonylmanganese tetrafluoroborate with veratrole (1,2-dimethoxybenzene) affords η6-veratrolemanganese tricarbonyl tetrafluoroborate in 66percent yield.This complex does not react satisfactorily with alkyllithium compounds, but it does undergo highly regioselective reaction with the lithium enolate of cyclohexanone, ortho to the MeO substituent.The product was converted to 2-(2,3-dimethoxyphenyl)cyclohexanone, thereby giving a novel and unique method for regioselective functionalization of veratrole.Similarly, anisolemanganese tricarbonyl tetrafluoroborate, and 4-bromoveratrolemanganese tricarbonyl tetrafluoroborate were prepared and their reactivity toward the enolate nucleophile was examined.

Selective C-C Bond Cleavage of Cycloalkanones by NaNO2/HCl

A novel selective fragmentation of cycloalkanones by NaNO2/HCl has been established. The C-C bond cleavage reaction proceeds smoothly under mild conditions, selectively affording versatile keto acids or oxime acids. The methodology can streamline the synthesis of valuable chiral molecules and isocoumarins from readily available feedstocks.

Diversity-Oriented Synthesis of Bioactive Azaspirocycles

A collection of novel azaspirocyclic β-arylethylamines was prepared in good yield and excellent diastereoselectivity by an expedient strategy that features condensation of a cyclic ketone with an amino allylsilane and a tandem aza-Sakurai cyclization to generate several different spirocyclic N-heterocycles. Subsequent elaboration of the spirocyclic scaffold was achieved via Pictet-Spengler cyclizations, Suzuki cross-coupling reactions, N-functionalizations, and olefin refunctionalization reactions to create a diverse library of compounds, several of which have nanomolar affinity for the sigma 1 receptor and transmembrane protein 97 (TMEM97).