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

General Description

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

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

• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 75-05-8 acetonitrile 
• 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 
• 2150-38-1 methyl 3,4-dimethoxybenzoate 
• 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 
• 199102-74-4 2-amino-5-(4-chlorobenzoyl)-3-(3,4-dimethoxybenzoyl)-4,5,6,7-tetrahydro-thieno[3,2-c]pyridine 
• 244298-89-3 (2-amino-4,5,6,7-tetrahydrobenzo[b]thiophen-3-yl)-(3,4-dimethoxyphenyl)methanone 
• 179327-04-9 2-amino-3-(3,4-dimethoxybenzoyl)-4,5-dimethylthiophene 
• 1029095-72-4 (Z)-2-cyano-1-(3,4-dimethoxyphenyl)vinyl trifluoromethanesulfonate 
• 1401219-51-9 N-(3-(3,4-dimethoxyphenyl)-1-(p-tolyl)-1H-pyrazol-5-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide 
• 1476782-09-8 5-(3,4-dimethoxyphenyl)furan-2,3,4-tricarbonitrile 
• 1082912-26-2 (2-amino-4-phenylthiophen-3-yl)(3,4-dimethoxyphenyl)methanone 
• 1265048-93-8 2-(3,4-dimethoxybenzoyl)-3-phenylbut-2-enenitrile 
• 199102-71-1 ω-cyano-4-isopropoxy-3-methoxyacetophenone 
• 208519-08-8 3-(3,4-dimethoxyphenyl)-2H-pyrazol-5-amine 

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).