2944-47-0

Usage

Uses

Used in Pharmaceutical Industry:
2-Isopropylanisole is used as a starting material for the synthesis of (±)-shonanyl methyl ether and (±)-ferruginyl methyl ether, which are compounds with potential applications in the pharmaceutical industry.
Used in Chemical Synthesis:
In the chemical synthesis industry, 2-Isopropylanisole may be used in the preparation of 4-bromo-2-isopropylanisole via bromination using a lithium bromide/ammonium cerium(IV) nitrate system. 2-ISOPROPYLANISOLE can be further utilized in various chemical reactions and applications.
Additionally, 2-Isopropylanisole is used as a starting material in the multi-synthesis of (±)-shonanyl methyl ether, which can be employed in the development of new compounds and products in the chemical industry.

InChI:InChI=1/C10H14O/c1-8(2)9-6-4-5-7-10(9)11-3/h4-8H,1-3H3

Upstream product

• 10278-02-1 2-(2-methoxyphenyl)propene 
• 21022-73-1 2-(2'-methoxyphenyl)-2-propanol 
• 88-69-7 2-(1-methylethyl)phenol 
• 74-88-4 methyl iodide 
• 4132-48-3 1-methoxy-4-(1-methylethyl)benzene 
• 134435-50-0 (3-Isopropyl-4-methoxy-phenyl)-acetaldehyde 
• 616-38-6 carbonic acid dimethyl ester 
• 77-78-1 dimethyl sulfate 
• 71-23-8 propan-1-ol 
• 86119-84-8 phosphoric acid 
• 100-66-3 methoxybenzene 
• 67-63-0 isopropyl alcohol 
• 7446-70-0 aluminium trichloride 
• 643-28-7 2-isopropylaniline 

Downstream Products

• 88-69-7 2-(1-methylethyl)phenol 
• 1004-77-9 2-isopropylcyclohexanone 
• 43209-90-1 6-isopropylcyclohex-2-en-1-one 
• 24591-33-1 4-bromo-2-isopropylanisole 
• 6380-20-7 3-isopropylanisole 
• 4132-48-3 1-methoxy-4-(1-methylethyl)benzene 
• 1706-81-6 2-Isopropyl-1-methoxy-4-nitro-benzene 
• 94112-85-3 4-Oxo-4-(3'-isopropyl-4'-methoxyphenyl)butyric acid 
• 1025911-50-5 4-(3-Isopropyl-4-methoxy-phenyl)-4-oxo-butyric acid ethyl ester 
• 91251-42-2 3-Isopropyl-4-methoxy-phenylamine 
• 134435-51-1 (E)-2-(3-Isopropyl-4-methoxy-phenyl)-5,9-dimethyl-deca-4,8-dienenitrile 
• 61494-73-3 12-hydroxy-abieta-8,11,13-trien-3,7-dione 
• 134435-54-4 7-Isopropyl-6-methoxy-1,1,4a-trimethyl-2-phenylsulfanyl-4,4a,10,10a-tetrahydro-1H-phenanthren-9-one 
• 134435-53-3 7-Isopropyl-6-methoxy-1,1,4a-trimethyl-2-phenylsulfanyl-2,3,4,4a,10,10a-hexahydro-1H-phenanthren-9-one 

Relevant academic research and scientific papers

Acid mediated deprotection of N-isopropyl tertiary amides

Tertiary amides containing an N-isopropyl group were selectively deprotected by heating in methanesulfonic acid. The N-isopropyl group was removed selectively in the presence of other groups on the amide nitrogen such as methyl, primary alkyl, or aryl. The putative isopropyl cation was trapped by Friedel-Crafts alkylation of anisole when the latter was included as a co-solvent.

Friedel-Crafts alkylation of anisole in supercritical carbon dioxide: A comparative study of catalysts

The Friedel-Crafts alkylation of anisole with n-propanol was carried out over five different Bronsted solid acid catalysts using supercritical carbon dioxide as the reaction medium. The reaction temperature and pressure were evaluated in terms of selectivity for the monoalkylated products, conversion of the starting material, and the products' isomeric ratio. Desulfonation of the catalysts was observed when the temperature was increased above 150°C for the organic supported catalysts investigated Amberlyst 15 and Purolite CT-175, and above 200 to 250°C for the inorganic supported catalysts Nafion SAC-13 and Deloxan ASP I/7. A decrease in the catalytic performance of organic supported catalysts was observed with increasing pressure. This decrease was related to the phase behaviour of the reaction.

Total Synthesis of 1-Oxomiltirone and Arucadiol

A practical and efficient approach for the total synthesis of arucadiol and 1-oxomiltirone is reported. The key step which involves an intramolecular [4+2] cycloaddition catalyzed by gold(III) bromide or copper(II) triflate leads to the formation of 6-6-6-fused aromatic abietane core.

Total synthesis of (±)-Scrodentoid A

An efficient total synthesis of scrodentoid A was accomplished starting from a Hagemann's ester and a substituted (2-bromoethyl)benzene. Key reactions in this synthesis include C-alkylation of the Hagemann's ester, 6-endo-Trig cationic cyclization of an enone and Lewis acid promoted isomerization of a cis-fused ketone.

Iridium-Catalyzed C(sp3)?H Addition of Methyl Ethers across Intramolecular Carbon–Carbon Double Bonds Giving 2,3-Dihydrobenzofurans

Intramolecular addition of an O-methyl C(sp3)?H bond across a carbon-carbon double bond occurs in the iridium-catalyzed reaction of methyl 2-(propen-2-yl)phenyl ethers. The Ir/(S)-DTBM-SEGPHOS catalyst promotes the reaction efficiently in toluene at 110–135 °C to afford 3,3-dimethyl-2,3-dihydrobenzofurans. Enantioselective C(sp3)?H addition is achieved in the reaction of methyl 2-(1-siloxyethenyl)phenyl ethers, affording enantioenriched 3-hydroxy-2,3-dihydrobenzofuran derivatives with up to 96% ee. (Figure presented.).

Enantioselective, Lewis Base-Catalyzed Sulfenocyclization of Polyenes

A sulfenium-ion-initiated, catalytic, enantioselective polyene cyclization is described. Homogeranylarenes and ortho-geranylphenols undergo polycyclization in good yield, diastereoselectivity, and enantioselectivity. The stereodetermining step is the generation of an enantiomerically enriched thiiranium ion from a terminal alkene and a sulfenylating agent in the presence of a chiral Lewis basic catalyst. The use of hexafluoroisopropyl alcohol as the solvent is crucial to obtain good yields. The thioether moiety resulting from the reaction can be subsequently transformed into diverse oxygen and carbon functionality postcyclization. The utility of this method is demonstrated by the enantioselective syntheses of (+)-ferruginol and (+)-hinokiol.

Syntheses and evaluation of multicaulin and miltirone-like compounds as antituberculosis agents

Four multicaulin and miltirone-like phenanthrene derivatives were synthesised and evaluated as antituberculosis agents. The crucial step of the synthesis was Pschorr coupling of 4-(3-isopropyl-4-methoxyphenyl)-2-(2-aminophenyl)ethane (13) to give 2-isopro

Diisobutylaluminum hydride-promoted cyclization of silylated 1,3-dien-5-ynes: Application to total synthesis of a 20-norabietane derivative

The diisobutylaluminum hydride (DIBAL-H)-promoted benzocyclization, recently developed by this group, was adopted for the synthesis of a natural product containing a 9,10-dihydrophenanthrene skeleton to demonstrate its synthetic utility. One of the extrac

Pd-PEPPSI-IHeptCl: A General-Purpose, Highly Reactive Catalyst for the Selective Coupling of Secondary Alkyl Organozincs

Dichloro[1,3-bis(2,6-di-4-heptylphenyl)imidazol-2-ylidene](3-chloropyridyl)palladium(II) (Pd-PEPPSI-IHeptCl), a new, very bulky yet flexible Pd–N-heterocyclic carbene (NHC) complex has been evaluated in the cross-coupling of secondary alkylzinc

Efficient synthesis of sterically hindered arenes bearing acyclic secondary alkyl groups by suzuki-miyaura cross-couplings

Bulky P,P-O ligands were designed to inhibit isomerization and reduction side reactions during the cross coupling between sterically hindered aryl halides and alkylboronic acids. Suzuki-Miyaura cross-couplings between di-ortho-substituted aryl bromides and acyclic secondary alkylboronic acids have been achieved with high yields. The method has also enabled the preparation of ortho-alkoxy di-ortho-substituted arenes bearing isopropyl groups in excellent yields. The utility of the synthetic method has been demonstrated in a late-stage modification of estrone and in the application to a new synthetic route toward gossypol. No side reaction: The shown bulky P,P-O ligands (right) successfully inhibit isomerization and reduction side reactions of the cross-coupling of sterically hindered substrates such as di-ortho-substituted aryl bromides with acyclic secondary alkylboronic acids. The method also allows the preparation of ortho-alkoxy di-ortho-substituted isopropyl arenes in excellent yields.