13388-75-5

Usage

Uses

Used in Organic Synthesis:
3,5-DIMETHOXYPHENYLACETONITRILE is used as a synthetic intermediate for the production of various organic compounds. Its unique structure allows it to be a versatile building block in the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 3,5-DIMETHOXYPHENYLACETONITRILE is used as a key component in the development of new drugs. Its chemical properties make it suitable for the synthesis of molecules with potential therapeutic applications, contributing to the discovery of novel treatments for various diseases.
Used in Agrochemical Industry:
3,5-DIMETHOXYPHENYLACETONITRILE also finds application in the agrochemical industry, where it is used in the synthesis of active ingredients for pesticides and other crop protection products. Its role in creating effective and environmentally friendly agrochemicals is crucial for modern agriculture.
Used in Specialty Chemicals:
In the specialty chemicals sector, 3,5-DIMETHOXYPHENYLACETONITRILE is employed as a precursor for the production of various high-value compounds. Its unique structure and reactivity make it an essential component in the synthesis of dyes, fragrances, and other specialty chemicals used in a wide range of applications.

Purification Methods

Crystallise the nitrile from MeOH or pet ether (b 90-110o). [Adams et al. J Am Chem Soc 70 664 1948, Sankaraman et al. J Am Chem Soc 109 5235 1987, Beilstein 10 I 198, 10 II 269, 10 III 1470.]

InChI:InChI=1/C10H11NO2/c1-12-9-5-8(3-4-11)6-10(7-9)13-2/h5-7H,3H2,1-2H3

Upstream product

• 6652-32-0 3,5-dimethoxybenzylchloride 
• 143-33-9 sodium cyanide 
• 17715-69-4 1-Bromo-2,4-dimethoxybenzene 
• 75-05-8 acetonitrile 
• 20469-65-2 1-bromo-3,5-dimethoxybenzene 
• 7311-34-4 3,5-dimethoxybenzaldehdye 
• 7677-24-9 trimethylsilyl cyanide 
• 877-88-3 3,5-dimethoxybenzyl bromide 
• 99-10-5 3,5-Dihydroxybenzoic acid 
• 773837-37-9 sodium cyanide 
• 2150-37-0 methyl 3,5-dimethoxybenzoate 
• 1132-21-4 3,5-dimethoxybenzoic acid 
• 705-76-0 3,5-dimethoxybenzyl alcohol 
• 151-50-8 potassium cyanide 

Downstream Products

• 25413-24-5 2-(3,5-dimethoxy-phenyl)-5-(4-methoxy-phenyl)-3-oxo-valeronitrile 
• 4670-10-4 (3,5-dimethoxyphenyl)acetic acid 
• 3213-28-3 3,5-dimethoxyphenethylamine 
• 22972-63-0 α,α-dimethyl-3,5-dimethoxyphenylacetonitrile 
• 66154-60-7 2-(3,5-dimethoxy-phenyl)-acetoacetonitrile 
• 114327-09-2 2-(3,5-dimethoxy-benzyl)-1,3-diphenyl-imidazolidine 
• 131196-71-9 1-(2,4-dihydroxyphenyl)-2-(3,5-dimethoxyphenyl)ethanone 
• 861064-92-8 ethyl 2-cyano-2-(3,5-dimethoxyphenyl)acetate 
• 15601-15-7 1-Cyan-1-(3,5-methoxy-phenyl)-heptanon-⁽²⁾ 
• 93427-22-6 (3,5-dimethoxy-2-nitrophenyl)acetonitrile 
• 75018-83-6 17β-tert-Butoxy-1,3-dimethoxy-9-oxo-9,10-seco-1,3,5(10)-oestratrien-6-α-carbonitril 
• 82055-07-0 17β-tert-Butoxy-1,3-dimethoxy-9-oxo-9,10-seco-1,3,5(10)-oestratrien-6β-carbonitril 
• 153742-19-9 methyl 2-cyano-2-(3,5-dimethoxyphenyl) acetate 
• 120353-00-6 α-isopropyl-3,5-dimethoxyphenylacetonitrile 

Relevant academic research and scientific papers

Synthesis and bioactivity evaluation of 2,3-diaryl acrylonitrile derivatives as potential anticancer agents

Thirty novel derivatives of 2,3-diaryl acrylonitrile were synthesized and evaluated for biological activity. Preliminary investigations of antitumor activity in vitro showed that most of the synthesized compounds have significant antiproliferative effects

Asymmetric total synthesis of nigerone and ent-nigerone: Enantioselective oxidative biaryl coupling of highly hindered naphthols

An enantioselective synthesis of the chiral bisnaphthopyrone natural product nigerone and its enantiomer, ent-nigerone, has been realized. The use of constrained 2-naphthol substrates was critical to producing highly functionalized chiral 1,1′-binaphthols via asymmetric oxidative biaryl coupling with 1,5-diaza-cis-decalin copper complexes. The final natural product was formed via a key eight-step isomerization process of the coupling product, bisisonigerone, and proceeded with retention of the biaryl con iguration. The axial configurations of bisisonigerone and nigerone were definitively established by a combination of circular dichroism (CD) measurements and quantum chemical CD calculations.

Stereoselective Total Synthesis of (-)-(2 S,4 R)-3′-Methoxyl Citreochlorol: Preparation and Use of New Proline-Based Auxiliary for Asymmetric Acetate Aldol Reaction

The first stereoselective total synthesis of (-)-(2S,4R)-3′-methoxy citreochlorol and (-)-(2S,4S)-3′-methoxy citreochlorol is demonstrated. A proline-based imidazolidinone was synthesized and used as chiral auxiliary for asymmetric acetate aldol reaction to generate initial chirality in the targeted molecule. Geminal dichloromethane functionality was introduced by the addition of in situ generated dichloromethyllithium to Weinreb's amide functional group.

FGFR INHIBITOR AND APPLICATION THEREOF

An azatricyclic compound (as represented by formula I) which acts as an inhibitor of fibroblast growth factor receptors (FGFR), as well as a pharmaceutical composition thereof, a preparation method, and a use therefor in the treatment of FGFR-mediated diseases. The azatricyclic compound exerts an effect by means of participating in the regulation of a plurality of processes such as cell proliferation, apoptosis, migration, neovascularization, and the like. AA%%%Formula (I).

Cyano-containing resveratrol analogue and preparation method and purpose thereof

The invention provides a cyano-containing resveratrol analogue and a preparation method and application thereof, and relates to the field of medical compounds. A structure of the cyano-containing resveratrol analogue is shown in the formula of the description; 3,5-dihydroxy-benzoic acid is mainly used as a raw material, and the cyano-containing resveratrol analogue is prepared by the following steps of methylation, reduction, brominating, Abozove rearrangement, Wittig-Hornor reaction and Knoevenegal reaction; in the preparation process of the cyano-containing resveratrol analogue, the chemical substances with lower toxicity, such as trimethylsilyl cyanide and tetrabutylammonium fluoride, are used for replacing chemicals with higher toxicity, such as sodium cyanide or potassium cyanide, to introduce cyano, so that the damage to the health of an operator is greatly decreased, and the serious harm to environments is avoided. The preparation method has the advantages that the yield is higher, the environment-friendly effect is good, and multiple types of cyano-containing resveratrol analogue with anti-cancer activity on cells can be obtained.

Mutasynthesis of Glycopeptide Antibiotics: Variations of Vancomycin's AB-Ring Amino Acid 3,5-Dihydroxyphenylglycine

In the mutasynthetic approach, the ΔdpgA mutant of the vancomycin-type glycopeptide antibiotic producer Amycolatopsis balhimycina, which is deficient in the synthesis of 3,5-dihydroxyphenylglycine (DPg), was supplemented with synthetic DPg analogues to obtain the corresponding modified glycopeptides. Sterically more demanding 3,5-disubstituted methoxy derivatives as well as monosubstituted DPg analogues were accepted as substrates. These facts indicate that steric and electronic requirements suffice in several cases for the oxidative closure of the AB ring, thus leading to the generation of novel antibiotically active glycopeptide derivatives. The results represent a further step in evaluating the potential of mutasynthesis for peptidic secondary metabolites. Copyright

Radical-mediated cyclisation of ω-aryl-β-dicarbonyl compounds to tetrahydrobenzocyclohepten-6-ones, hexahydrobenzocycloocten-6-ones and naphthalen-2(1H)-ones

Manganese(III) acetate in acetic acid promotes efficient radical-mediated oxidative cyclisation of ε-aryl-β-dicarbonyl and Z-γ,δ-unsaturated δ-aryl-β-dicarbonyl compounds carrying electron-releasing groups in the aromatic ring, forming 6,7,8,9-tetrahydro-5H-benzocyclohepten-6-ones and naphthalen-2(1H)-ones, respectively. The process is accompanied by secondary acetoxylation at the activated benzylic position of the initial cyclisation products, and is exemplified by the conversions of the ε- and δ-aryl-β-dicarbonyl compounds 6 and 11 into the benzocycloheptenone 18 and the naphthalenone 21, respectively. Application of the oxidation to the formation of 8-membered hexahydro- and tetrahydro-benzocycloocten-6-ones 19 and 22 from ζ-aryl-β-dicarbonyl and Z-γ,δ-unsaturated ζ-aryl-β-dicarbonyl compounds is limited by low reactivity, and in the latter case, by radical rearrangement followed by cyclisation to a tetralin.

A Total Synthesis of the Sesquiterpene Quinone Metachromin-A

The first total synthesis of the marine natural product metachromin A was accomplished through a convergent synthesis amenable to the preparation of synthetic analogues.The main features of this synthesis are the introduction the oxygenation at C17 employing a Thiele acetoxylation reaction and a stereoselective Horner-Wadsworth-Emmons coupling of a nonstabilized phosphonate with a methyl ketone derivative to generate the required (E)-trisubstituted double bond.

ARYNIC CONDENSATION OF NITRILE ANIONS IN THE PRESENCE OF THE COMPLEX BASE NaNH2-CH3CH2(OCH2CH2)2ONa

Nitrile anions are easily condensed with aryl halides in the presence of Complex Base NaNH2-CH3CH2(OCH2CH2)2ONa via the intermediate arynes.