22080-96-2

Usage

Uses

Used in Pharmaceutical Industry:
4-Hydroxy-2,6-dimethoxybenzaldehyde is used as a test compound for investigating the bactericidal activity of benzaldehydes against various bacterial strains, including Campylobacter jejuni, Escherichia coli, Listeria monocytogenes, and Salmonella enterica. This application is significant in the development of new antimicrobial agents and understanding the effectiveness of benzaldehydes in combating bacterial infections.
Used in Chemical Synthesis:
In the field of chemical synthesis, 4-Hydroxy-2,6-dimethoxybenzaldehyde serves as a valuable intermediate for the creation of various complex organic molecules. Its unique structure allows for further functionalization and modification, making it a versatile building block in organic chemistry.
Used in Research and Development:
4-Hydroxy-2,6-dimethoxybenzaldehyde is also used in research and development settings, particularly in the study of chemical reactions and the synthesis of novel compounds. Its reactivity and structural features make it an interesting subject for scientific inquiry and potential applications in various industries.

Synthesis Reference(s)

Synthetic Communications, 21, p. 167, 1991 DOI: 10.1080/00397919108020808

InChI:InChI=1/C9H10O4/c1-12-8-3-6(11)4-9(13-2)7(8)5-10/h3-5,11H,1-2H3

Upstream product

• 500-99-2 3,5-dimethoxyphenol 
• 68-12-2 N,N-dimethyl-formamide 
• 7647-01-0 hydrogenchloride 
• 60-29-7 diethyl ether 
• 134778-17-9 (3,5-dimethoxyphenoxy)triisopropylsilane 
• 108-73-6 3,5-dihydroxyphenol 
• 103-70-8 Formanilid 

Downstream Products

• 22080-97-3 3,5-dimethoxy-4-methylphenol 
• 679428-14-9 1-benzyloxy-4-formyl-3,5-dimethoxybenzene 
• 925671-39-2 2,6-dimethoxy-4-[3-(perfluorooctyl)propyloxy]benzaldehyde 
• 22080-98-4 Phenylessigsaeure-(3.5-dimethoxy-4-methyl-phenylester) 
• 22080-99-5 6-Hydroxy-2,4-dimethoxy-3-methyl-desoxybenzoin 
• 22081-01-2 6-hydroxy-2,4,4'-trimethoxy-3-methyl-deoxybenzoin 
• 22081-03-4 2,4-Dimethoxy-phenylessigsaeure-(3,5-dimethoxy-4-methyl-phenylester) 
• 22081-04-5 6-Hydroxy-2,4,2',4'-tetramethoxy-3-methyl-desoxybenzoin 
• 1217490-66-8 [8-(4-benzyloxy-2,6-dimethoxyphenyl)-2,7-dimethylpyrazolo[1,5-a][1,3,5]triazin-4-yl]bis(2-methoxyethyl)amine 
• 1217490-69-1 4-{[bis(2-methoxyethyl)amino]-2,7-dimethyl-pyrazolo[1,5-a][1,3,5]triazin-8-yl}-3,5-dimethoxyphenol 
• 1217490-72-6 trifluoromethanesulfonic acid 4-{4-[bis(2-methoxyethyl)amino]-2,7-dimethylpyrazolo[1,5-a][1,3,5]triazin-8-yl}-3,5-dimethoxyphenyl ester 
• 1217490-78-2 [8-(4-bromo-2,6-dimethoxyphenyl)-2,7-dimethyl-pyrazolo[1,5-a][1,3,5]triazin-4-yl]bis(2-methoxyethyl)amine 
• 1217490-53-3 (4-benzyloxy-2,6-dimethoxyphenyl)acetonitrile 
• 1217490-54-4 2-(4-benzyloxy-2,6-dimethoxyphenyl)-3-oxobutyronitrile 

Relevant academic research and scientific papers

Scale-up of a Vilsmeier formylation reaction: Use of HEL Auto-MATE and simulation techniques for rapid and safe transfer to pilot plant from laboratory

The application of reaction calorimetry and process modelling to allow for the rapid and safe scale-up of a Vilsmeier formylation reaction to the pilot plant will be described. This transformation was a key step in the preparation of the backbone amide linker (the so-called "BAL" handle) for solid-phase chemistry. In particular, use was made of Auto-MATE equipment from Hazard Evaluation Laboratories (HEL) and "Reaction Simulator" software to derive a thermokinetic model which allowed us to simulate heat-flow data on-scale. The model was then refined using a HEL SIMULAR 1-L calorimeter, and a direct comparison of the data showed there to be a 20% error in the enthalpy data gathered from the smaller Auto-MATE. The use of a preformed Vilsmeier reagent and dichloromethane as a reaction solvent gave a "square-wave" profile typical of a feed-controlled reaction. These conditions were successfully scaled to a 50-L pilot-plant vessel.

Process for performing an isolated Pd(II)-mediated oxidation reaction

There is disclosed a process for performing an isolated Pd(II) mediated oxidation reaction electrochemically. The inventive process is performed on an electrode array device having a plurality of separately addressable electrodes. Preferably, the Pd(II) m

Compounds with growth hormone releasing properties

Compounds of peptide mimetic nature having the general formula I STR1 wherein a and b are independently 1 or 2, R1 and R2 are independently H or C1-6 alkyl, G and J are independently, inter alia, aromats, and D and E are independently several different groups are growth hormone secretagogous with improved bioavailability.

Formylations of anions with a 'Weinreb' formamide: N-methoxy-N-methylformamide

Treatment of organolithiums, Grignard reagents, or enolates with N-methoxy-N-methylformamide leads to formylated products in good yields without competing secondary processes.

Regioselective preparation of 4-formyl-3,5-dimethoxyphenol, an intermediate in the synthesis of the PAL solid-phase peptide synthesis handle

An improved procedure for preparation of 4-formyl-3,5-dimethoxyphenol is reported. The principal advantages of the new procedure over previous preparations are complete regioselectivity and higher yield.

Preparation and application of the 5-(4-(9-fluorenylmethyloxycarbonyl) aminomethyl-3,5-dimethoxyphenoxy)-valeric acid (PAL) handle for the solid-phase synthesis of C-terminal peptide amides under mild conditions1-3

The acid-labile 5-(4-(9-fluorenylmethyloxycarbonyl) aminomethyl-3,5-dimethoxyphenoxy)valeric acid (PAL) handle 1 is described for the solid-phase synthesis of C-terminal peptide amides. The pure para isomer of 1 was prepared by each of two efficient five-step routes, in overall yields from 52% to 74%. The handle 1 was coupled onto a variety of amino group-containing supports to provide a general starting point for stepwise assembly of peptide chains according to a wide range of chemistries. In particular, protocols based on the base-labile N(α)-9-fluorenylmethyloxycarbonyl (Fmoc) group worked well with PAL handle 1. For small model peptides, final cleavage of tert-butyl side-chain protecting groups and of the anchoring linkage proceeded smoothly in trifluroacetic acid-dichloromethane-dimethyl sulfide (14:5:1) (reagent A) at 25 °C for 2 h. For cleavage of complex peptides that contain several sensitive side-chain functionalities, or that include arginine residues blocked with the 4-methoxy-2,3,6-trimethylphenylsulfonyl (Mtr) or 2,2,5,7,8-pentamethylchroman-6-ylsulfonyl (Pmc) groups, a mixture of trifluoroacetic acid-thioanisole-1,2-ethanedithiol-anisole (90:5:3:2) (reagent R), applied for 2-8 h at 25 °C, was preferred. A side reaction involving alkylation at tryptophan was elucidated, and conditions were developed to minimize its occurrence. The methodology was demonstrated by syntheses of over a hundred peptides, among which acyl carrier protein (65-74) amide (natural and retro sequences), luteinizing hormone-releasing hormone, adipokinetic hormone, PHI porcine fragment (18-27), and human gastrin-I are highlighted in this report. In comparative studies, the yields and purities of peptide amides prepared with PAL were shown to be equivalent or superior to those found for products prepared by alternative procedures from the recent literature.

Trimethoxyphenyl Compounds, XI. Constituents of Hagenia abyssinica, 2: Synthesis of Phloracylophenones Containing One Phloroglucinol Unit

For the Koso constituents K6 and K8, we previously proposed the structures 1a, b and 2a, b.These assignments have been confirmed by synthesis. - Keywords: Flores koso, Revised Structure, Synthesis of Phloroglucinols

Naturally Occurring Dibenzofurans. Part 4. Synthesis of Dibenzofurandiols by Annelation of Benzofurans

Methyl 3-acetylbenzofuran-2-ylacetate (8) undergoes C-methylation affording methyl 2-(3-acetylbenzofuran-2-yl)propionate (13).These compounds and similar oxo esters undergo ready cyclization to dibenzofurandiols on treatment with sodium methoxide in boiling methanol.A convenient synthesis of dimethyl furan-2,5-diylacetate (30) is described, as are attempts to synthesize 1,3,7,9-tetramethoxy-2,8-dimethyldibenzofuran (3).

A C-Methylbiflavone from Cephalotaxus harringtonia K. Koch

6-C-Methyl-7-O-methylamentoflavone (1) isolated from the leaves of Cephalotaxus harringtonia K.Koch (Cephalotaxaceae) has been identified on the basis of the spectral data of its hexamethyl ether (1a) and its penta-acetate (1b).The location of the C-methyl group was first deduced from 1H n.m.r. studies with a lanthanide shift reagent and confirmed by a synthesis of the hexamethyl ether (1a).