49609-84-9

Basic information

• Product Name: 2-Chloronicotinyl chloride
• Synonyms: 2-CHLORONICOTINIC ACID CHLORIDE;2-CHLORONICOTINOYL CHLORIDE;2-CHLORONICOTINYL CHLORIDE;2-CHLOROPYRIDINE-3-CARBONYL CHLORIDE;2-Chloro-3-pyridine carboxylic acid chloride;2-Chloronictinoyl Chloride;2-Chloronicotinyl chloride, 98+%;2-Chloronicotinoylchloride,98+%
• CAS NO: 49609-84-9
• Molecular Formula: C₆H₃Cl₂NO
• Molecular Weight: 176
• EINECS: -0
• Product Categories: ACIDHALIDE;Pyridine;Pyridines;Chloropyridines;Halopyridines;C6Heterocyclic Building Blocks;Halogenated Heterocycles;Heterocyclic Building Blocks;pyridine series;Aromatics;Heterocycles
• Mol File: 49609-84-9.mol

Chemical Properties

• Melting Point: 38 °C
• Boiling Point: 96 °C
• Flash Point: >110°C
• Appearance: White to beige-yellow/Low Melting Solid
• Density: 1.2942 (rough estimate)
• Vapor Pressure: 0.036mmHg at 25°C
• Refractive Index: 1.5680 (estimate)
• Storage Temp.: 0-10°C
• Solubility: Chloroform, DMSO, Ethyl Acetate
• PKA: -2.00±0.10(Predicted)
• Sensitive: Moisture Sensitive
• BRN: 119022
• CAS DataBase Reference: 2-Chloronicotinyl chloride(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Chloronicotinyl chloride(49609-84-9)
• EPA Substance Registry System: 2-Chloronicotinyl chloride(49609-84-9)

Safety Data

• Hazard Codes: C
• Statements: 14-29-34
• Safety Statements: 22-26-30-36/37/39-45-8-27
• RIDADR: 3096
• WGK Germany: 3
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 49609-84-9(Hazardous Substances Data)

Usage

Uses

Used in Pesticide Industry:
2-Chloronicotinyl chloride is used as an intermediate in the production of the synergistic pesticide Boscalid. This pesticide is known for its effectiveness in controlling various pests and diseases in crops, thereby enhancing agricultural productivity and crop protection.
Used in Pharmaceutical Industry:
2-Chloronicotinyl chloride is also utilized in the preparation of thieno[2.3-b]pyrrole derivatives, which are cannabinoid receptor agonists. These agonists have potential applications in the monoand combination therapy of various diseases, offering new treatment options and improving patient outcomes.

InChI:InChI=1/C6H5Cl2N/c7-4-5-2-1-3-9-6(5)8/h1-3H,4H2

Upstream product

• 609-71-2 2-hydroxy-3-carboxypyridine 
• 2398-81-4 Nicotinic acid N-oxide 
• 2942-59-8 2-chloronicotinic acid 
• 97510-86-6 potassium 2-chloro-nicotinate 
• 1452-94-4 ethyl 2-chloronicotinate 
• 123-91-1 1,4-dioxane 
• 121495-79-2 2-chloropyridine-3-carbonyl chloride hydrochloride 
• 59-67-6 nicotinic acid 
• 6602-54-6 2-chloro-3-pyridinecarbonitrile 
• 35905-85-2 2-bromonicotinic acid 
• 152361-99-4 ethyl 2-chloro-2-cyano-5-oxopentanoate 

Downstream Products

• 40134-18-7 methyl 2-chloropyridine-3-carboxylate 
• 56149-29-2 2-chloro-N-phenylpyridine-3-carboxamide 
• 53062-98-9 (2-chloropyridin-3-yl)(morpholino)methanone 
• 85678-83-7 5-Oxo-5H-<1,3>thiazolo<3,2-a>pyrido<3,2-e>pyrimidine 
• 85678-90-6 N-(1,3-Thiazol-2-yl)-2-chloropyridine-3-carboxamide 
• 109321-39-3 N-(1,3,4-Thiadiazol-2-yl)-2-chloropyridine-3-carboxamide 
• 85678-91-7 2-Chloro-N-(4-methyl-thiazol-2-yl)-nicotinamide 
• 152038-51-2 2-Chloro-N-(2'-chloro-5'-pyridinyl)pyridine-3-carboxamide 
• 132312-86-8 2-Chloro-N-(2'-chloro-3'-pyridinyl)-3-pyridinecarboxamide 
• 100791-06-8 4-(2-Chloro-pyridine-3-carbonyl)-5-methyl-1,3-dihydro-imidazol-2-one 
• 110545-74-9 (2-chloro-3-pyridinyl)<2-(4-morpholinyl)-1-cyclohexen-1-yl>methanone 
• 153615-34-0 2-<(2-chloro-3-pyridinyl)carbonyl>-1-cyclohexen-1-yl-2-chloro-3-pyridinecarboxylate 
• 109321-51-9 2-Chloro-N-(4-phenyl-thiazol-2-yl)-nicotinamide 
• 109321-40-6 2-Chloro-N-(5-phenyl-[1,3,4]thiadiazol-2-yl)-nicotinamide 

Relevant articles and documents

Substituted-nicotinyl thiourea derivatives bearing pyrimidine moiety: Synthesis and biological evaluation

A series of substituted-nicotinyl thiourea derivatives containing pyrimidine ring were synthesized in good to excellent yield using PEG-400 as solid-liquid phase transfer catalyst under ultrasonic irradiation. The structures of all newly synthesized compounds were elucidated and confirmed by IR, 1H NMR and elemental analysis. The preliminary biological tests show that some of the target compounds present good inhibitory activities against the root and stalk of dicotyledon plants and are safe for monocotyledon plants.

Ligand-free copper-catalyzed efficient one-pot access of benzo[b]pyrido[3,2-f][1,4]oxazepinones through O-heteroarylation-Smiles rearrangement-cyclization cascade

Efficient synthesis of a library of novel benzopyrido[1,4]oxazepinones was accomplished by Cs2CO3-mediated one-pot coupling of N-substituted-o-chloronicotinamides and o-halogenated phenols using cuprous oxide catalysis in DMF at 120 °C through an O-heteroarylation-Smiles rearrangement-cyclization cascade (16 examples). The C-N bond construction process is biased in favour of Smiles rearrangement allowing regioselective generation of these tricyclic molecular architectures essentially free from Goldberg-N-arylation products in good to excellent yields.

NAD(P+/NAD(P)H models. 83. Molecular asymmetry with a carbonyl group: Electronically controlled stereochemistry in the reaction of NAD(P)+/NAD(P)H analogs

The N-methylpyridinium salt of 6,7-dihydro-6-methyl-5-oxopyridino[3,2-d]-2-benzazepin has been synthesized. The salt has axial chirality with respect to the orientation of the carbonyl dipole. An enantiomer of the cation has been obtained as the iodide sa

Novel 2-chloro-8-arylthiomethyldipyridodiazepinone derivatives with activity against HIV-1 reverse transcriptase

Based on the molecular modeling analysis against Y181C HIV-1 RT, dipyridodiazepinone derivatives containing an unsubstituted lactam nitrogen and 2-chloro-8-arylthiomethyl were synthesized via an efficient route. Some of them were evaluated for their antiviral activity against HIV-1 RT subtype E and were found to exhibit virustatic activity comparable to some clinically used therapeutic agents.

Synthesis and process optimization of Boscalid by catalyst Pd-PEPPSI-IPrDtBu-An

The purpose of this research was to reduce the amount of noble metal palladium catalyst and improve the catalytic performance in the Suzuki–Miyaura cross-coupling reaction, which is the key step in the synthesis of Boscalid. Taking o-bromonitrobenzene and p-chlorophenylboronic acid as raw materials, three kinds of Pd-PEPPSI-IPr catalysts were synthesized and employed in the Suzuki reaction, and then the biaryl product was subjected to reduction and condensation reaction to give Boscalid. Under the optimal reaction conditions, the result showed that the catalytic system exhibits highest catalytic efficiency under aerobic conditions, giving the 2-(4-chlorophenyl)nitrobenzene in over 99 % yield. Moreover, the Pd-PEPPSI-IPrDtBu-An catalyst was minimized to 0.01 mol%. The synthesis process was mild, the post-treatment was simple, and the production cost was reduced, which makes it suitable for industrial production.

Pyrido[2,3-b][1,5]benzoxazepin-5(6H)-one derivatives as CDK8 inhibitors

CDK8 is a cyclin-dependent kinase that forms part of the mediator complex, and modulates the transcriptional output from distinct transcription factors involved in oncogenic control. Overexpression of CDK8 has been observed in various cancers, representing a potential target for developing novel CDK8 inhibitors in cancer therapeutics. In the course of our investigations to discover new CDK8 inhibitors, we designed and synthesized tricyclic pyrido[2,3-b][1,5]benzoxazepin-5(6H)-one derivatives, by introduction of chemical complexity in the multi-kinase inhibitor Sorafenib taking into account the flexibility of the P-loop motif of CDK8 protein observed after analysis of structural information of co-crystallized CDK8 inhibitors. In vitro evaluation of the inhibitory activity of the prepared compounds against CDK8 led us to identify compound 2 as the most potent inhibitor of the series (IC50 = 8.25 nM). Co-crystal studies and the remarkable selectivity profile of compound 2 are presented. Compound 2 showed moderate reduction of phosphorylation of CDK8 substrate STAT1 in cells, in line with other reported Type II CDK8 inhibitors. We propose herein an alternative to find a potential therapeutic use for this chemical series.

INHIBITORS OF INDOLEAMINE 2,3-DIOXYGENASE AND METHODS OF THEIR USE

The present invention provides a compound of formula (II): an inhibitor of indoleamine 2,3-dioxygenase (IDO), which may be used as medicaments for the treatment of proliferative disorders, such as cancer, viral infections and/or autoimmune diseases. Its prodrugs are disclosed.

New green technology for preparation of 2-chloronicotinic acid

The invention relates to a new green technology for preparation of 2-chloronicotinic acid. The technology includes: adopting nicotinic acid (I) as the raw material, conducting hydrogen peroxide N-oxidation under the action of a catalyst in a water system to obtain nicotinic acid N-oxide (II), then under the action of organic base, conducting phosphorus oxychloride chlorination to synthesize 2-chloronicotinyl chloride (III), and then performing hydrolysis and refining to obtain 2-chloronicotinic acid (IV). The method avoids the use of benzene and acetic acid, has the advantages of short process, safety and environmental protection, good product quality and high yield, is an environment-friendly green synthetic route, and is suitable for industrial production.

A fluorine-containing thiazole aromatic amide compound and use thereof

The invention discloses a thiazole fluoride-containing aromatic amide compound, which has a structure as shown in the general formula I in the description, wherein R is shown in the description. The compound shown in the general formula I has excellent st

Mechanism of Acylative Oxidation-Reduction-Condensation Reactions Using Benzoisothiazolones as Oxidant and Triethylphosphite as Stoichiometric Reductant

We previously described a new organocatalytic oxidation-reduction-condensation for amide/peptide construction. The reaction system relies on triethylphosphite as the stoichiometric reductant and organocatalytic benzoisothiazolone/O2 in air as the oxidant. The reaction was assumed to generate catalytic quantities of S-acylthiosalicylamides as electrophiles, which are rapidly intercepted by amine reactants to generate amides/peptides and o-mercaptobenzamides. The latter are then gently reoxidized to the benzoisothiazolones under Cu-catalyzed aerobic conditions to complete the catalytic cycle. To gain a mechanistic understanding, we describe herein our studies of the stoichiometric generation of S-acylthiosalicylamides under oxidation-reduction-condensation conditions from a variety of benzoisothiazolones and carboxylic acids using triethylphosphite as the terminal reductant. These studies have revealed the presence of more than one reaction pathway when benzoisothiazolones react with triethylphosphite (including a rapid, direct deoxygenation of certain classes of benzoisothiazolones by triethylphosphite) and allow the identification of optimal reaction characteristics (benzoisothiazolone structure and solvent) for the generation of thioesters. These explorations will inform our efforts to develop highly effective and robust organocatalytic oxidation-reduction-condensation reactions that are based on the benzoisothiazolone and related motifs.