7314-44-5

Usage

Uses

Used in Pharmaceutical Industry:
2,4-Dimethoxybenzyl alcohol is used as a medical intermediate for the synthesis of various pharmaceutical compounds. Its ability to react with different reagents and form new compounds makes it a valuable component in the development of drugs with specific therapeutic properties.
Used in Chemical Synthesis:
In the field of chemical synthesis, 2,4-Dimethoxybenzyl alcohol serves as a versatile building block for creating a range of organic compounds. Its reactivity with trifluoroacetic acid and subsequent conversion to calix[4]resorcinarene octamethyl ether and the derived octa-acetate highlights its potential in synthesizing complex molecules for various applications.
Used in Research and Development:
2,4-Dimethoxybenzyl alcohol is also utilized in research and development settings, where its unique chemical properties are explored for potential applications in creating new materials, improving existing compounds, and understanding the underlying chemical reactions involved in their formation.

InChI:InChI=1/C9H12O3/c1-11-8-4-3-7(6-10)9(5-8)12-2/h3-5,10H,6H2,1-2H3

Upstream product

• 613-45-6 2,4-Dimethoxybenzaldehyde 
• 91-52-1 2,4 dimethoxybenzoic acid 
• 67-56-1 methanol 
• 67-63-0 isopropyl alcohol 
• 91-01-0 1,1-Diphenylmethanol 
• 53088-00-9 2-phenyl-2,3-dihydro-1H-benzoimidazole 
• 2150-41-6 methyl 2, 4-dimethoxybenzoate 
• 89-86-1 4-hydroxysalicylic acid 
• 98-85-1 1-Phenylethanol 
• 6496-89-5 2,4-dimethoxyphenylacetic acid 

Downstream Products

• 55791-52-1 1-(chloromethyl)-2,4-dimethoxybenzene 
• 46316-13-6 1-(2,4-Dimethoxybenzyl)-1-methylhydrazin 
• 157886-16-3 Fmoc-Asp(Ot-Bu)-ODbn 
• 17715-70-7 1,3-dimethoxy-4-fluorobenzene 
• 613-45-6 2,4-Dimethoxybenzaldehyde 
• 82770-23-8 (2,4-dimethoxyphenyl)methyl 1-(2-propenyl)-4-pentenyl carbonate 
• 258876-09-4 2,4-dimethoxybenzyl phenylacetate 
• 161919-74-0 1-bromomethyl-2,4-dimethoxybenzene 
• 181823-27-8 2-(2,4-Dimethoxy-benzylsulfanyl)-nicotinic acid 
• 114719-65-2 (2,4-dimethoxyphenyl)methanethiol 
• 216067-79-7 N-[(2,4-Dimethoxyphenyl)methyl]phthalimide 
• 221675-75-8 2,4-dimethoxybenzyl 2-methylpropanoate 
• 334936-14-0 [bis-(2,2,2-trifluoro-ethoxy)-phosphoryl]-acetic acid 2,4-dimethoxy-benzyl ester 
• 99585-22-5 benzo[h]quinoline-5,6-diol 

Relevant academic research and scientific papers

High yield synthesis of the parent C-unsubstituted calix[4]resorcinarene octamethyl ether

Treatment of 2,4-dimethoxybenzyl alcohol with trifluoroacetic acid (TFA, 5% in CHCl3) affords, in almost quantitative yield calix[4]resorcinarene octamethyl ether, which on demethylation and acetylation yields the derived octa-acetate.

Nickel catalyzed sustainable synthesis of benzazoles and purines: Via acceptorless dehydrogenative coupling and borrowing hydrogen approach

Herein we report nickel-catalyzed sustainable synthesis of a few chosen five-membered fused nitrogen heterocycles such as benzimidazole, purine, benzothiazole, and benzoxazole via acceptorless dehydrogenative functionalization of alcohols. Using a bench stable, easy to prepare, and inexpensive Ni(ii)-catalyst, [Ni(MeTAA)] (1a), featuring a tetraaza macrocyclic ligand (tetramethyltetraaza[14]annulene (MeTAA)), a wide variety of polysubstituted benzimidazole, purine, benzothiazole, and benzoxazole derivatives were prepared via dehydrogenative coupling of alcohols with 1,2-diaminobenzene, 4,5-diaminopyrimidine, 2-aminothiphenol, and 2-aminophenol, respectively. A wide array of benzimidazoles were also prepared via a borrowing hydrogen approach involving alcohols as hydrogen donors and 2-nitroanilines as hydrogen acceptors. A few control experiments were performed to understand the reaction mechanism.

Synthesis of acyclic and cyclic phosphonates based on substituted 2-hydroxybenzylic alcohols

A convenient synthesis of benzylic phosphonates and 2,3-dihydrobenzo[d][1,2]oxaphosphole 2-oxides substituted at the aromatic ring, as well as their precursors, 2-hydroxybenzylic alcohols, from the derivatives of salicylic aldehyde, salicylic acid, and 2-hydroxyacetophenone bearing an additional hydroxy or methoxy group at the para position of the aromatic ring was developed. For the first time, the possibility of selective demethylation of the methoxy group positioned ortho to the methylene phosphonate fragment with retention of the methoxy group at the para position was shown.

On the Necessity of Nucleobase Protection for 2-Thiouracil for Fmoc-Based Pseudo-Complementary Peptide Nucleic Acid Oligomer Synthesis

A selection of benzyl-based protecting groups for thiouracil (SU) for the synthesis of pseudo-complementary peptide nucleic acid (PNA) has been evaluated. The 4-methoxybenzyl-protecting group that has found use for SU during Boc-based oligomerization is also suitable for Fmoc-based oligomerization. Furthermore, it is demonstrated that SU protection is unnecessary for the successful synthesis of thiouracil-containing PNA. The new 2-thiothymine (ST) PNA monomer has also been prepared and incorporated into an oligomer and its binding to complementary PNA evaluated.

Novel indole and triazole based hybrid molecules exhibit potent anti-adipogenic and antidyslipidemic activity by activating Wnt3a/β-catenin pathway

Obesity and dyslipidemia is the two facet of metabolic syndrome, which needs further attention. Recent studies indicate triazole and indole derivatives have remarkable anti-obesity/antidyslipidemic activity. To harness the above-mentioned potential, a series of novel triazole clubbed indole derivatives were prepared using click chemistry and evaluated for anti-adipogenic activity. Based on the structure-activity relationship, essential functional groups which potentiate anti-adipogenic activity were identified. The lead compound 13m exhibited potent anti-adipogenic activity compared to its parent compounds with the IC-50 value of 1.67 μM. Further evaluation of anti-adipogenic activity was conducted in different cell lines such as C3H10T1/2 and hMSC with positive result. The anti-adipogenic effect of compound 13m was most prominent in the early phase of adipogenesis, which is driven by the G1 to S phase cell cycle arrest during mitotic clonal expansion. The mechanistic study suggests that compound 13m exhibit anti-adipogenic property by activating Wnt3a/β-catenin pathway, a known suppressor of key adipogenic genes PPARγ and C/EBPα. It is noteworthy that the compound 13m also reduced serum triglyceride, LDL and total cholesterol in Syrian Golden hamster model of dyslipidemia. The anti-adipogenic activity of compound 13m can also be correlated with decreased expression of PPARγ and increased expression of β-catenin in epididymal white adipose tissue (eWAT) in vivo. The compound 13m also increased the expression of genes involved in reverse cholesterol transport (RCT) such as PPARα and LXR1α indicating another mechanism by which compound 13m ameliorates dyslipidemia in Syrian Golden hamster model. Overall this study provides a unique perspective into the anti-adipogenic/antidyslipidemic property of triazole and indole hybrids molecules with further scope to increase the anti-adipogenic potency for therapeutic intervention of obesity and metabolic syndrome.

Transfer hydrogenation and hydration of aromatic aldehydes and nitriles using heterogeneous NiO nanofibers as a catalyst

A simple and efficient hydrogen transfer reaction of aldehydes and hydration of nitriles using nickel oxide nanofibers (NiO NFs) as a heterogeneous catalyst is reported. NiO NFs prepared by electrospinning technique was cubic (confirmed by XRD) with an average diameter of 80 nm (obtained from HR-TEM) and utilized as a nanocatalyst for heterogeneous transfer hydrogenation of aromatic aldehydes and hydration of aromatic nitriles. All the reaction products produced with minimum reaction time and maximum yield were confirmed using GC-MS with NIST library. Furthermore, heterogeneity of the catalyst was confirmed with ICP-MS analysis. The as-prepared catalyst was reused for six cycles and was found to be efficient. Hence, the present catalytic synthesis of alcohols and amides may be an economically viable process.

Cobalt complex catalyzed atom-economical synthesis of quinoxaline, quinoline and 2-alkylaminoquinoline derivatives

A new phosphine-free Co(ii) complex-catalyzed synthesis of various quinoxalines via dehydrogenative coupling of vicinal diols with both o-phenylenediamines and 2-nitroanilines is reported. This complex was also effective for the synthesis of quinolines. The practical aspect of this catalytic system was revealed by the one-pot synthesis of 2-alkylaminoquinolines.

A nickel catalyzed acceptorless dehydrogenative approach to quinolines

A general, efficient and environmentally benign, one-step synthesis of substituted quinoline derivatives was achieved by acceptorless dehydrogenative coupling of o-aminobenzylalcohols with ketones and secondary alcohols catalyzed by a cheap, earth abundant and easy to prepare nickel catalyst [Ni(MeTAA)], featuring a tetraaza macrocyclic ligand (tetramethyltetraaza[14]annulene (MeTAA)). A wide variety of substituted quinolines were synthesized in high yields starting from readily available o-aminobenzylalcohols and ketones or secondary alcohols. A few controlled reactions were carried out to establish the acceptorless dehydrogenative nature of the reactions.

Heterobimetallic tin(II) oxido clusters of the type [{Sn6(μ3-O)4(μ3-OCH2R)4} {W(CO)5}4] and [{Sn5(μ3-O)2(μ-OCH2R)4(μ3-OCH2R)2}{Fe(CO)4}2]

Reaction of the tin(II) alkoxides bis(2-methoxyphenylmethanolate)tin(II) (1) and bis(2,4-dimethoxyphenylmethanolate)tin(II) (2) with [W(CO)5(thf)] and [Fe2(CO)9], respectively, gave the heterobimetallic tin(II) oxido clusters [{Sn6(μ3-O)4(μ3-OCH2R)4}{W(CO)5}4] [3, R[dbnd6]C6H4(OCH3)-2); 4, R[dbnd6]C6H3(OCH3)2-2,4] and [{Sn5(μ3-O)2(μ-OCH2R)4(μ3-OCH2R)2}{Fe(CO)4}2] [5, R[dbnd6]C6H3(OCH3)2-2,4] which were isolated reproducibly with fair yield as a result of partial hydrolysis in the presence of moisture. The metal oxido clusters are composed of polynuclear tin(II) oxido cages entrapped by arylmethanolato ligands and coordinated to metal carbonyl moieties via lone pairs of electrons at tin. The compounds were analyzed by single crystal X-ray diffraction analysis (1, 4·2THF and 5), elemental analyses, ATR-IR spectroscopy and1H,13C{1H} and119Sn{1H) NMR spectroscopy in solution as well as in solid state.

FeCl3-catalyzed self-cleaving deprotection of methoxyphenylmethyl-protected alcohols

4-Methoxyphenylmethyl ethers are widely utilized as alcohol protecting groups. FeCl3 effectively catalyzes the deprotection of methoxyphenylmethyl-type ethers in a self-cleaving manner to produce oligomeric derivatives and alcohols. Remarkably, the highly pure mother alcohols can be obtained without silica gel column chromatography by using the 2,4-dimethoxyphenylmethyl group as a protective group.