5673-07-4

Usage

Uses

Used in Chemical Synthesis:
2,6-Dimethoxytoluene is used as an organic chemical synthesis intermediate for various applications in the chemical industry. Its unique structure allows it to be a versatile building block for the synthesis of a wide range of compounds, including pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Fragrance Industry:
Due to its pleasant aromatic odor, 2,6-dimethoxytoluene is also utilized in the fragrance industry as a component in the formulation of perfumes, colognes, and other scented products. Its ability to blend well with other fragrance ingredients makes it a valuable addition to the perfumer's palette.
Used in Dyes and Pigments:
2,6-DIMETHOXYTOLUENE's aromatic nature and chemical structure make it suitable for use in the production of dyes and pigments. It can be employed as a starting material or intermediate in the synthesis of various colorants used in the textile, plastics, and printing industries.
Used in Laboratory Research:
2,6-Dimethoxytoluene is also used in laboratory research as a reagent or starting material for the synthesis of various organic compounds. Its availability and relatively simple structure make it a popular choice for researchers working on the development of new chemical entities and materials.

Synthesis Reference(s)

Journal of the American Chemical Society, 78, p. 771, 1956 DOI: 10.1021/ja01585a020

Purification Methods

Sublime 2,6-dimethoxytoluene in vacuo. Distil it (preferably under reduced pressure) and/or recrystallise it from pentane, EtOH or aqueous MeOH. [Sankaraman et al. J Am Chem Soc 109 5235 1987]. [Beilstein 6 H 872, 6 III 4513, 6 IV 5877.]

InChI:InChI=1/C9H12O2/c1-7-8(10-2)5-4-6-9(7)11-3/h4-6H,1-3H3

Upstream product

• 6971-52-4 3-methoxy-2-methylphenol 
• 608-25-3 2-methylbenzene-1,3-diol 
• 77-78-1 dimethyl sulfate 
• 151-10-0 1,3-Dimethoxybenzene 
• 2785-97-9 (2,6-dimethoxyphenyl)lithium 
• 3392-97-0 2,6-dimethoxybenzaldehyde 
• 67-56-1 methanol 
• 16700-55-3 2,6-dimethoxybenzyl alcohol 
• 64-17-5 ethanol 
• 634-36-6 1,2,3-trimethoxybenzene 
• 60319-07-5 trifluoromethanesulfonic acid 2,6-dimethoxyphenyl ester 
• 594-27-4 tetramethylstannane 
• 74-88-4 methyl iodide 
• 2065-27-2 methyl 2,6-dimethoxybenzoate 

Downstream Products

• 855890-85-6 1-(2-hydroxy-4-methoxy-3-methyl-phenyl)-heptadecan-1-one 
• 1466-76-8 2-6-dimethoxybenzoic acid 
• 22794-95-2 1-bromo-2,4-dimethoxy-3-methylbenzene 
• 7149-92-0 2,4-dimethoxy-3-methylbenzaldehyde 
• 77942-03-1 1-(2,4-dimethoxy-3-methylphenyl)-2-methylbut-2-en-1-one 
• 96938-84-0 1-Benzyl-5-chloro-4-(2-hydroxy-4-methoxy-3-methylbenzoyl)-1H-1,2,3-triazole 
• 96938-86-2 1-Benzyl-5-chloro-4-(2,4-dimethoxy-3-methylphenylthio)-1H-1,2,3-triazole 
• 96938-85-1 1-Benzyl-5-chloro-4-(2-hydroxy-4-methoxy-3-methylphenylthio)-1H-1,2,3-triazole 
• 6971-52-4 3-methoxy-2-methylphenol 
• 84568-08-1 5-Bromo-2-methoxy-3-methyl-1,4-benzoquinone 
• 123266-78-4 (E)-3-(2-Azido-6-benzyloxy-3,5-dimethoxy-4-methyl-phenyl)-1-phenyl-propenone 
• 109365-01-7 1,3-dimethoxy-2-methyl-4-nitrobenzene 
• 105103-98-8 2,4-dimethoxy-3-methyl-1-chlorobenzene 
• 102333-30-2 2,4-dimethoxy-3-methylbenzenesulfinyl chloride 

Relevant academic research and scientific papers

Exhaustive Reduction of Esters Enabled by Nickel Catalysis

We report a one-step procedure to directly reduce unactivated aryl esters into their corresponding tolyl derivatives. This is achieved by an organosilane-mediated ester hydrosilylation reaction and subsequent Ni/NHC-catalyzed hydrogenolysis. The resulting conditions provide a direct and efficient alternative to multi-step procedures for this transformation that often require the use of hazardous metal hydrides. Applications in the synthesis of -CD3-containing products, derivatization of bioactive molecules, and chemoselective reduction in the presence of other C-O bonds are demonstrated.

Mild partial deoxygenation of esters catalyzed by an oxazolinylborate-coordinated rhodium silylene

An electrophilic, coordinatively unsaturated rhodium complex supported by borate-linked oxazoline, oxazoline-coordinated silylene, and N-heterocyclic carbene donors [{κ3-N,Si,C-PhB(OxMe2)(OxMe2SiHPh)ImMes}Rh(H)CO][HB(C6F5)3] (2, OxMe2 = 4,4-dimethyl-2-oxazoline; ImMes = 1-mesitylimidazole) is synthesized from the neutral rhodium silyl {PhB(OxMe2)2ImMes}RhH(SiH2Ph)CO (1) and B(C6F5)3. The unusual oxazoline-coordinated silylene structure in 2 is proposed to form by rearrangement of an unobserved isomeric cationic rhodium silylene species [{PhB(OxMe2)2ImMes}RhH(SiHPh)CO][HB(C6F5)3] generated by H abstraction. Complex 2 catalyzes reductions of organic carbonyl compounds with silanes to give hydrosilylation products or deoxygenation products. The pathway to these reactions is primarily influenced by the degree of substitution of the organosilane. Reactions with primary silanes give deoxygenation of esters to ethers, amides to amines, and ketones and aldehydes to hydrocarbons, whereas tertiary silanes react to give 1,2-hydrosilylation of the carbonyl functionality. In contrast, the strong Lewis acid B(C6F5)3 catalyzes the complete deoxygenation of carbonyl compounds to hydrocarbons with PhSiH3 as the reducing agent.

Hydrogenation of substituted aromatic aldehydes: Nucleophilic trapping of the reaction intermediate, application to the efficient synthesis of methylene linked flavanol dimers

The synthesis of dimeric flavanols is the consequence of the possible trapping of the reaction intermediates generated in the course of the reductive hydrogenation of substituted benzaldehydes. The scope of this reaction is investigated.

Phenyl benzisoxazoles as estrogenic agents

This invention provides estrogen receptor modulators of formula I, having the structure wherein, R1, R2, and R3 are as defined in the specification, or a pharmaceutically acceptable salt thereof.

Method for orthometalation of a carbocyclic aromatic derivative bearing at least an electron donor group

The invention concerns a method for orthometalation of a carbocyclic aromatic derivative bearing at least an electron donor group, characterised in that it consists in reacting said carbocyclic aromatic derivative with an efficient amount of at least one alkaline metal in the presence of a compound of formula (I): RX, wherein: R represents a hydrocarbon radical having 1 to 20 carbon atoms which can be a saturated or unsaturated, linear or branched, acyclic aliphatic radical; a saturated or unsaturated, monocyclic or polycyclic cycloaliphatic radical; a saturated or unsaturated, linear or branched aliphatic radical bearing a cyclic substituent; and X represents a bromine or chlorine atom.

Palladium-Catalyzed Cross-Coupling Reactions of Highly Hindered, Electron-Rich Phenol Triflates and Organostannanes

The palladium-catalyzed cross-coupling reaction of highly hindered, electron-rich phenol triflates and organostannanes (Stille reaction) has been studied in a systematic manner.The following are its salient features: (1) electron-rich phenol triflates require triphenylphosphine to undergo palladium-catalyzed cross-couplings; (2) in general, efficient reactions take place only when larger-than-usual amounts (10-15percent) of palladium are employed.On the reagent side, alkyl- (methyl only), allyl-, vinyl- and alkinylstannanes undergo efficient cross-couplings with the titlesubstrates.However, some limitations to this novel entry to 2-substituted resorcinols exist in regard to both substrates and reagents.Thus, conformationally rigid (hexasubstituted) aryl triflates behave poorly, demethylation being an important side reaction.Moreover, alkyl groups other than methyl cannot be introduced because β elimination occurs more rapidly.The potentially powerful synthesis of hindered biaryls has also been studied briefly.In the present conditions, the reaction appears to be limited by the presence of ortho substituents on the arylstannane moiety.

The Alkali Metal Reduction of Trimethoxybenzenes in Hydrocarbon Solvents

A series of trimethoxybenzenes was subjected to reduction in hydrocarbon solvents. 1,2,3-Trimethoxybenzene (1) and 1,2,4-trimethoxybenzene (2) underwent selective demethoxylation in high yields, whereas the 1,3,5-substituted isomer 3 proved resistant to the reduction conditions.The reactions mechanism involves the fission of a methoxyl radical from an initial radical anion.The accompanying side-reactions, i.e. demethylation and deoxygenation, may be suppressed by the addition of n-butanol as a proton source.

Palladium catalyzed cross-coupling of phenol triflates with organostannanes. A versatile approach for the synthesis of substituted resorcinol dimethyl ethers.

2,6-Dimethoxy-substituted phenol triflates undergo efficient Pd(0) catalyzed cross coupling with organostannanes, thus providing an easy access to substituted resorcinol dimethyl ethers, a common building block of many aromatic polyketides.

REGIOSELECTIVE REDUCTIVE ALKYLATION OF 1,2,3-TRIMETHOXYBENZENE

The 2-methoxyl group of 1,2,3-trimethoxybenzene and its 5-methyl-substituted homologue is removed under electron transfer conditions and replaced with an alkyl group in a one-pot procedure.

Synthesis of 9a-Deoxymitomycin Congeners

The protected mitosane (23) is prepared in stereospecific manner.The key reactions included in the synthetic scheme are (i) Lewis acid-mediated Claisen-type rearrangement of the penta-2,4-dienyl aryl ether (10) to the penta-2,4-dienylphenol (11), (ii) the regioselective incorporation of the alkoxymethyl group at the 1-position of the pentadienyl side-chain in the protected pentadienylhydroquinone (12), and (iii) the stereospecific copper-catalysed double cyclization of the azido(penta-2,4-dienyl)quinone (15) to the 3H-pyrroloindole-5,8-dione (16) in one step.Subsequent stereospecific introduction of the aziridine ring furnishes the target compound (23).