40296-46-6

Basic information

• Product Name: Ethyl 4,6-dichloronicotinate
• Synonyms: 4,6-DICHLOROPYRIDINE-3-CARBOXYLIC ACID ETHYL ESTER;4,6-DICHLORONICOTINIC ACID ETHYL ESTER;ETHYL 4,6-DICHLORONICOTINATE;2,4-Dichloro-5-carbethoxypyridine;4,6-Dichloronicotinic acid ethyl ester ,97%;ethyl 4,6-dichloronicotinate (en);Ethyl 4,6-dichloronicotinate ,97%;ethyl 4,6-dichloropyridine-3-carboxylate
• CAS NO: 40296-46-6
• Molecular Formula: C₈H₇Cl₂NO₂
• Molecular Weight: 220.05
• Product Categories: Pyridine series;Boronic Acid
• Mol File: 40296-46-6.mol
• Article Data: 33

Chemical Properties

• Melting Point: 32-34°
• Boiling Point: 85°C/0.01mmHg(lit.)
• Flash Point: 120.9 °C
• Appearance: Yellow/Liquid
• Density: 1.367 g/cm³
• Vapor Pressure: 0.00484mmHg at 25°C
• Refractive Index: 1.54
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility: Soluble in methanol.
• PKA: -1.24±0.10(Predicted)
• CAS DataBase Reference: Ethyl 4,6-dichloronicotinate(CAS DataBase Reference)
• NIST Chemistry Reference: Ethyl 4,6-dichloronicotinate(40296-46-6)
• EPA Substance Registry System: Ethyl 4,6-dichloronicotinate(40296-46-6)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36
• HazardClass: IRRITANT
• Hazardous Substances Data: 40296-46-6(Hazardous Substances Data)

Usage

Description

Ethyl 4,6-dichloronicotinate is a white solid that serves as a crucial intermediate in the synthesis of various compounds, including pharmaceuticals, agrochemicals, and dyes. Its chemical structure allows it to participate in multiple reactions, making it a versatile building block in the development of new molecules with potential applications in different industries.

Uses

Used in Pharmaceutical Industry:
Ethyl 4,6-dichloronicotinate is used as a key intermediate for the preparation of (acylamino)aminonaphthyridinones, which are analogs of novobiocin and act as Hsp90 inhibitors. These compounds exhibit antitumor activities in human breast cancer cell lines and can influence apoptosis and cell cycle progression, making them promising candidates for cancer treatment.
Used in Organic Synthesis:
Ethyl 4,6-dichloronicotinate is utilized as an important raw material and intermediate in organic synthesis, where it can be employed to create a wide range of chemical products. Its reactivity and structural features make it a valuable component in the development of new molecules with various applications.
Used in Agrochemical Industry:
In the agrochemical industry, Ethyl 4,6-dichloronicotinate is used as a starting material for the synthesis of various agrochemicals, such as pesticides and herbicides. Its role in this industry is to provide a foundation for the development of effective and environmentally friendly solutions for crop protection.
Used in Dye Industry:
Ethyl 4,6-dichloronicotinate is also used as a fine chemical intermediate in the dye industry. Its chemical properties allow it to be incorporated into the synthesis of various dyes, contributing to the development of new colorants with improved properties and applications.

InChI:InChI=1/C8H7Cl2NO2/c1-2-13-8(12)5-4-11-7(10)3-6(5)9/h3-4H,2H2,1H3

Upstream product

• 73027-79-9 4,6-dichloro-nicotinic acid 
• 64-17-5 ethanol 
• 141-52-6 sodium ethanolate 
• 107836-75-9 4,6-dichloropyridine-3-carbonyl chloride 
• 105-50-0 diethyl 1,3-acetonedicarboxylate 
• 6975-44-6 4-Hydroxy-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid ethyl ester 
• 6975-44-6 4,6-dihydroxynicotinic acid ethyl ester 

Downstream Products

• 73027-79-9 4,6-dichloro-nicotinic acid 
• 845655-96-1 6-chloro-4-hydrazino-nicotinic acid ethyl ester 
• 107836-75-9 4,6-dichloropyridine-3-carbonyl chloride 
• 1417792-29-0 C₁₅H₁₅NO₂ 
• 29051-45-4 4-methyl-6-phenyl-nicotinic acid 
• 1442474-48-7 3-(3-(5-(3-(3,5-difluorophenyl)ureido)-4-fluoro-2-methylphenyl)-1-ethyl-2-oxo-1,2-dihydro-1,6-naphthyridin-7-yl)-1,1-dimethylurea 
• 1442474-55-6 N-(1-ethyl-3-(4-fluoro-2-methyl-5-(3-phenylureido)phenyl)-2-oxo-1,2-dihydro-1,6-naphthyridin-7-yl)azetidine-1-carboxamide 
• 1442474-57-8 1-(5-(1-ethyl-7-((6-methylpyridin-3-yl)amino)-2-oxo-1,2-dihydro-1,6-naphthyridin-3-yl)-2-fluoro-4-methylphenyl)-3-phenylurea 
• 1442474-59-0 1-(5-(7-chloro-1-ethyl-2-oxo-1,2-dihydro-1,6-naphthyridin-3-yl)-2,4-difluorophenyl)-3-phenylurea 
• 1442474-60-3 3-(3-(2,4-difluoro-5-(3-phenylureido)phenyl)-1-ethyl-2-oxo-1,2-dihydro-1,6-naphthyridin-7-yl)-1,1-dimethylurea 
• 1442474-61-4 3-(dimethylamino)-N-(1-ethyl-3-(4-fluoro-2-methyl-5-(3-phenylureido)phenyl)-2-oxo-1,2-dihydro-1,6-naphthyridin-7-yl)azetidine-1-carboxamide 
• 1442474-64-7 1-(5-(1-ethyl-7-((1-methyl-1H-pyrazol-4-yl)amino)-2-oxo-1,2-dihydro-1,6-naphthyridin-3-yl)-2-fluoro-4-methylphenyl)-3-phenylurea 
• 1442470-62-3 3-(5-amino-2-chloro-4-fluorophenyl)-1-ethyl-7-(tetrahydro-2H-pyran-4-ylamino)-1,6-naphthyridin-2(1H)-one 
• 1442470-63-4 3-(5-amino-2-chloro-4-fluorophenyl)-1-ethyl-7-(3-methoxypropylamino)-1,6-naphthyridin-2(1H)-one 

Relevant articles and documents

Design, synthesis and anti-HIV evaluation of novel diarylnicotinamide derivatives (DANAs) targeting the entrance channel of the NNRTI binding pocket through structure-guided molecular hybridization

Through a structure-based molecular hybridization approach, a novel series of diarylnicotinamide derivatives (DANAs) targeting the entrance channel of HIV-1 NNRTIs binding pocket (NNIBP) were rationally designed, synthesized and evaluated for their anti-H

Novel approach towards 3,7-disubstituted 1,6-naphthyridin-4(1H)-ones exploiting cross-coupling and SNAr reactions of a dihalogenated compound

A new route towards the synthesis of a series of 3,7-disubstituted 1,6-naphthyridin-4(1H)-ones in moderate to good yields is reported. The strategy involves the preparation of a 3,7-dihalogenated compound that undergoes differential functionalization using palladium-catalyzed cross-coupling and SNAr reactions.

Quinolone amides as antitrypanosomal lead compounds with In Vivo activity

Human African trypanosomiasis (HAT) is a major tropical disease for which few drugs for treatment are available, driving the need for novel active compounds. Recently, morpholino-substituted benzyl amides of the fluoroquinolone-type antibiotics were identified to be compounds highly active against Trypanosoma brucei brucei. Since the lead compound GHQ168 was challenged by poor water solubility in previous trials, the aim of this study was to introduce structural variations to GHQ168 as well as to formulate GHQ168 with the ultimate goal to increase its aqueous solubility while maintaining its in vitro antitrypanosomal activity. The pharmacokinetic parameters of spray-dried GHQ168 and the newly synthesized compounds GHQ242 and GHQ243 in mice were characterized by elimination half-lives ranging from 1.5 to 3.5 h after intraperitoneal administration (4 mice/compound), moderate to strong human serum albumin binding for GHQ168 (80%) and GHQ243 (45%), and very high human serum albumin binding (>99%) for GHQ242. For the lead compound, GHQ168, the apparent clearance was 112 ml/h and the apparent volume of distribution was 14 liters/kg of body weight (BW). Mice infected with T. b. rhodesiense (STIB900) were treated in a stringent study scheme (2 daily applications between days 3 and 6 postinfection). Exposure to spray-dried GHQ168 in contrast to the control treatment resulted in mean survival durations of 17 versus 9 days, respectively, a difference that was statistically significant. Results that were statistically insignificantly different were obtained between the control and the GHQ242 and GHQ243 treatments. Therefore, GHQ168 was further profiled in an early-treatment scheme (2 daily applications at days 1 to 4 postinfection), and the results were compared with those obtained with a control treatment. The result was statistically significant mean survival times exceeding 32 days (end of the observation period) versus 7 days for the GHQ168 and control treatments, respectively. Spray-dried GHQ168 demonstrated exciting antitrypanosomal efficacy.