4640-69-1

Basic information

• Product Name: 3,4-DIMETHOXYBENZOYLACETONITRILE
• Synonyms: 3,4-DIMETHOXYBENZOYLACETONITRILE;3-(3,4-DIMETHOXYPHENYL)-3-OXOPROPANENITRILE;3-(3,4-DIMETHOXY-PHENYL)-3-OXO-PROPIONITRILE;3,4-dimethoxbenzoylacetonitrile;3-(3,4-Dimethoxyphenyl)-3-oxopropanenitrile, 3-(3,4-Dimethoxyphenyl)-3-oxopropionitrile;3-(3,4-dimethoxyphenyl)-3-keto-propionitrile
• CAS NO: 4640-69-1
• Molecular Formula: C₁₁H₁₁NO₃
• Molecular Weight: 205.21
• Mol File: 4640-69-1.mol
• Article Data: 12

Chemical Properties

• Melting Point: 139-141°C
• Boiling Point: 377.5°C at 760 mmHg
• Flash Point: 165.1°C
• Appearance: /
• Density: 1.147g/cm³
• Vapor Pressure: 6.71E-06mmHg at 25°C
• Refractive Index: 1.517
• Storage Temp.: 2-8°C
• PKA: 8.05±0.12(Predicted)
• CAS DataBase Reference: 3,4-DIMETHOXYBENZOYLACETONITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: 3,4-DIMETHOXYBENZOYLACETONITRILE(4640-69-1)
• EPA Substance Registry System: 3,4-DIMETHOXYBENZOYLACETONITRILE(4640-69-1)

Safety Data

• Hazard Codes: Xi
• HazardClass: IRRITANT
• Hazardous Substances Data: 4640-69-1(Hazardous Substances Data)

Usage

Description

3,4-DIMETHOXYBENZOYLACETONITRILE, a chemical compound with the molecular formula C11H11NO3, is a nitrile derivative of 3,4-dimethoxybenzoylacetone. It is a white to off-white solid at room temperature and is commonly used as an intermediate in the synthesis of various pharmaceuticals and agrochemicals. As a building block, it is employed for the preparation of diverse heterocyclic compounds. It also serves as a reagent and precursor in research and development for the synthesis of biologically active molecules. However, due to potential health and environmental risks, it should be handled and used with caution.

Uses

Used in Pharmaceutical Industry:
3,4-DIMETHOXYBENZOYLACETONITRILE is used as an intermediate for the synthesis of various pharmaceuticals, contributing to the development of new drugs and medications. Its role in the creation of heterocyclic compounds makes it valuable in the production of a wide range of therapeutic agents.
Used in Agrochemical Industry:
In the agrochemical sector, 3,4-DIMETHOXYBENZOYLACETONITRILE is utilized as an intermediate in the synthesis of various agrochemicals, including pesticides and herbicides. Its involvement in the production of these chemicals helps to improve agricultural productivity and crop protection.
Used in Research and Development:
3,4-DIMETHOXYBENZOYLACETONITRILE is used as a reagent and precursor in research and development for the synthesis of biologically active molecules. Its application in this field aids scientists in discovering and creating new compounds with potential applications in medicine, agriculture, and other industries.
Used in the Synthesis of Heterocyclic Compounds:
3,4-DIMETHOXYBENZOYLACETONITRILE is used as a building block for the preparation of diverse heterocyclic compounds. These compounds are important in various chemical and pharmaceutical applications, making 3,4-DIMETHOXYBENZOYLACETONITRILE a valuable component in the synthesis of complex organic molecules.

InChI:InChI=1/C11H11NO3/c1-14-10-4-3-8(7-11(10)15-2)9(13)5-6-12/h3-4,7H,5H2,1-2H3

Upstream product

• 2150-38-1 methyl 3,4-dimethoxybenzoate 
• 75-05-8 acetonitrile 
• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 1116-98-9 cyanoacetic acid tert-butyl ester 
• 2859-78-1 4-Bromoveratrole 
• 82102-37-2 9-methyl-9H-fluorene-9-carbonyl chloride 
• 3943-77-9 ethyl veratrate 
• 3535-37-3 3,4-dimethoxybenzoic acid chloride 
• 151-50-8 potassium cyanide 

Downstream Products

• 179327-28-7 (2-amino-6-ethyl-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-3-yl)-(3,4-dimethoxy-phenyl)-methanone 
• 179327-24-3 2-amino-6-benzyl-3-(3,4-dimethoxybenzoyl)-4,5,6,7-tetrahydrothieno[2,3-c]pyridine 
• 199102-72-2 2-amino-7-benzyloxycarbonyl-3-(3,4-dimethoxybenzoyl)-4,5,6,7-tetrahydrothieno[2,3-b]pyridine 
• 199102-52-8 2-amino-6-benzoyl-3-(3,4-dimethoxybenzoyl)-4,5,6,7-tetrahydrothieno[2,3-c]pyridine 
• 179327-07-2 ethyl 6-chloromethyl-4-(3,4-dimethoxyphenyl)-2,3-dimethylthieno[2,3-b]pyridine-5-carboxylate 
• 244298-87-1 2-chloromethyl-4-(3,4-dimethoxy-phenyl)-benzo[4,5]thieno[2,3-b]pyridine-3-carboxylic acid ethyl ester 
• 179327-43-6 2-chloromethyl-4-(3,4-dimethoxy-phenyl)-7-ethyl-5,6,7,8-tetrahydro-9-thia-1,7-diaza-fluorene-3-carboxylic acid ethyl ester 
• 199101-54-7 ethyl 2-(diethylaminomethyl)-4-(3,4-dimethoxyphenyl)-5,6,7,8-tetrahydrothieno[2,3-b:5,4-c']dipyridine-3-carboxylate 
• 199102-09-5 ethyl 2-(diethylaminomethyl)-4-(3,4-dimethoxyphenyl)-5,6,7,8-tetrahydrothieno[2,3-b:5,4-b']dipyridine-3-carboxylate 
• 199102-02-8 ethyl 2-(diethylaminomethyl)-4-(3,4-dimethoxyphenyl)-5,6,7,8-tetrahydrothieno[2,3-b:4,5-c']dipyridine-3-carboxylate 
• 179327-39-0 ethyl 7-benzyl-2-chloromethyl-4-(3,4-dimethoxyphenyl)-5,6,7,8-tetrahydrothieno[2,3-b:5,4-c']dipyridine-3-carboxylate 
• 199102-55-1 7-benzoyl-2-chloromethyl-4-(3,4-dimethoxy-phenyl)-5,6,7,8-tetrahydro-9-thia-1,7-diaza-fluorene-3-carboxylic acid ethyl ester 
• 199102-75-5 ethyl 6-(4-chlorobenzoyl)-2-chloromethyl-4-(3,4-dimethoxyphenyl)-5,6,7,8-tetrahydrothieno[2,3-b:4,5-c']dipyridine-3-carboxylate 

Relevant articles and documents

Deadly KCN and pricey metal free track for accessing β-ketonitriles employing mild reaction conditions

A one pot synthesis of β-ketonitriles from readily accessible 3-chloropropenals using economically benign iodine, aqueous ammonia and sodium hydroxide solution, employing mild reaction conditions have been described. This report presents a convenient, inexpensive, highly toxic-matter-free and eco-friendly approach for β-ketonitriles.

Combining structure- and property-based optimization to identify selective FLT3-ITD inhibitors with good antitumor efficacy in AML cell inoculated mouse xenograft model

FLT3 mutation is among the most common genetic mutations in acute myeloid leukemia (AML), which is also related with poor overall survival and refractory in AML patients. Recently, FLT3 inhibitors have been approved for AML therapy. Herein, a series of new compounds with pyrazole amine scaffold was discovered, which showed potent inhibitory activity against FLT3-ITD and significant selectivity against both FLT3-ITD and AML cells expressing FLT3-ITD. Compound 46, possessing the most promising cellular activity, blocked the autophosphorylation of FLT3 pathway in MV4-11 cell line. Furthermore, the apoptosis and downregulation of P-STAT5 were also observed in tumor cells extracted from the MV4-11 cell xenografts model upon compound 46 treatment. Compound 46 was also metabolically stable in vitro and suppressed tumor growth significantly in MV4-11 xenografts model in vivo. Compound 46 showed no toxicity to the viscera of mice and caused no decrease in body weight of mice. In conclusion, the results of this study could provide valuable insights into discovery of new FLT3 inhibitors, and compound 46 was worthy of further development as potential drug candidate to treat AML.

Design, synthesis, and evaluation of 2-aryl-7-(3′,4′-dialkoxyphenyl)-pyrazolo[1,5-a]pyrimidines as novel PDE-4 inhibitors

Described herein is design, synthesis, and biological evaluation of novel series of 2-aryl-7-(3′,4′-dialkoxyphenyl)-pyrazolo[1,5-a]pyrimidines acting as inhibitors of type 4 phosphodiesterase (PDE4) which is known as a good target for the treatment of asthma and COPD. For this purpose, structure optimization was conducted with the aid of structure-based drug design using the known X-ray crystallography. Also, biological effects of these compounds on the target enzyme were evaluated by using in vitro assays, leading to the potent and selective PDE-4 inhibitor (IC50 10 nM).