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METHYL 2,6-DICHLOROPYRIDINE-3-CARBOXYLA& is an organic compound that serves as an intermediate in the synthesis of various pharmaceuticals and agrochemicals. It is characterized by its chlorinated pyridine ring and carboxylate group, which can be further functionalized to produce a range of derivatives with diverse applications.

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  • 65515-28-8 Structure
  • Basic information

    1. Product Name: METHYL 2 6-DICHLOROPYRIDINE-3-CARBOXYLA&
    2. Synonyms: METHYL 2 6-DICHLOROPYRIDINE-3-CARBOXYLA&;methyl 2,6-dichloronicotinate (en);2,6-two chloroMethyl nicotinate;Methyl2,6-dichloronicotinate,97%;2,6-Dichloropyridine-3-carboxylic acid methyl ester;Methyl 2,6-dichloropyridin-3-carboxylate;3-Pyridinecarboxylic acid, 2,6-dichloro-, methyl ester
    3. CAS NO:65515-28-8
    4. Molecular Formula: C7H5Cl2NO2
    5. Molecular Weight: 206.027
    6. EINECS: N/A
    7. Product Categories: N/A
    8. Mol File: 65515-28-8.mol
  • Chemical Properties

    1. Melting Point: 56-60 °C(lit.)
    2. Boiling Point: 270.517 °C at 760 mmHg
    3. Flash Point: 117.405 °C
    4. Appearance: /
    5. Density: 1.426 g/cm3
    6. Vapor Pressure: 0.007mmHg at 25°C
    7. Refractive Index: 1.548
    8. Storage Temp.: Inert atmosphere,Room Temperature
    9. Solubility: N/A
    10. PKA: -4.55±0.10(Predicted)
    11. Sensitive: Air Sensitive
    12. CAS DataBase Reference: METHYL 2 6-DICHLOROPYRIDINE-3-CARBOXYLA&(CAS DataBase Reference)
    13. NIST Chemistry Reference: METHYL 2 6-DICHLOROPYRIDINE-3-CARBOXYLA&(65515-28-8)
    14. EPA Substance Registry System: METHYL 2 6-DICHLOROPYRIDINE-3-CARBOXYLA&(65515-28-8)
  • Safety Data

    1. Hazard Codes: Xn
    2. Statements: 22-36/37/38
    3. Safety Statements: 26-36
    4. WGK Germany: 3
    5. RTECS:
    6. HazardClass: IRRITANT
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 65515-28-8(Hazardous Substances Data)

65515-28-8 Usage

Uses

Used in Pharmaceutical Industry:
METHYL 2,6-DICHLOROPYRIDINE-3-CARBOXYLA& is used as a key intermediate in the synthesis of various pharmaceutical compounds. Its chlorinated pyridine ring and carboxylate group can be modified to produce a range of active pharmaceutical ingredients with different therapeutic properties.
Used in Agrochemical Industry:
METHYL 2,6-DICHLOROPYRIDINE-3-CARBOXYLA& is also used as a building block in the development of agrochemicals, such as herbicides and insecticides. Its unique chemical structure allows for the creation of compounds with targeted pest control properties, contributing to more effective and environmentally friendly agricultural practices.
Used in Organic Synthesis:
METHYL 2,6-DICHLOROPYRIDINE-3-CARBOXYLA& is utilized as a versatile starting material in organic synthesis, enabling the production of a variety of organic compounds with different functional groups and applications. Its reactivity and stability make it a valuable component in the synthesis of complex organic molecules.
Used in Replacement of Halides:
METHYL 2,6-DICHLOROPYRIDINE-3-CARBOXYLA& is used in the replacement of chlorides with fluorides using anhydrous nucleophilic fluoride salts generated from potassium fluoride and an arene transfer agent. This process allows for the selective substitution of halide groups, enabling the synthesis of novel compounds with improved properties and applications.

Check Digit Verification of cas no

The CAS Registry Mumber 65515-28-8 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 6,5,5,1 and 5 respectively; the second part has 2 digits, 2 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 65515-28:
(7*6)+(6*5)+(5*5)+(4*1)+(3*5)+(2*2)+(1*8)=128
128 % 10 = 8
So 65515-28-8 is a valid CAS Registry Number.
InChI:InChI=1/C7H5Cl2NO2/c1-12-7(11)4-2-3-5(8)10-6(4)9/h2-3H,1H3

65515-28-8 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
  • Price
  • Detail
  • Alfa Aesar

  • (H51092)  Methyl 2,6-dichloronicotinate, 97%   

  • 65515-28-8

  • 250mg

  • 632.0CNY

  • Detail
  • Alfa Aesar

  • (H51092)  Methyl 2,6-dichloronicotinate, 97%   

  • 65515-28-8

  • 1g

  • 1793.0CNY

  • Detail
  • Aldrich

  • (656437)  Methyl2,6-dichloropyridine-3-carboxylate  97%

  • 65515-28-8

  • 656437-1G

  • 2,255.76CNY

  • Detail

65515-28-8SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name Methyl 2,6-dichloropyridine-3-carboxylate

1.2 Other means of identification

Product number -
Other names methyl 2,6-dichloropyridine-3-carboxylate

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:65515-28-8 SDS

65515-28-8Relevant articles and documents

HETEROCYCLIC COMPOUNDS AS KINASE INHIBITORS

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Paragraph 0414, (2021/01/23)

Heterocyclic compounds as CDK4 or CDK6 or other CDK inhibitors are provided. The compounds may find use as therapeutic agents for the treatment of diseases and may find particular use in oncology.

2-AMINO-N-HETEROARYL-NICOTINAMIDES AS NAV1.8 INHIBITORS

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Page/Page column 103, (2020/05/28)

Novel compounds of the structural formula (I), and the pharmaceutically acceptable salts thereof, are inhibitors of Nav1.8 channel activity and may be useful in the treatment, prevention, management, amelioration, control and suppression of diseases mediated by Nav1.8 channel activity. The compounds of the present invention may be useful in the treatment, prevention or management of pain disorders, cough disorders, acute itch disorders, and chronic itch disorders.

BENZO[B][1,8]NAPHTHYRIDINE ACETIC ACID DERIVATIVES AND METHODS OF USE

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Page/Page column 126, (2020/12/01)

Compounds of Formula I or pharmaceutically acceptable salts or esters thereof capable of binding to and modulating the activity of a stimulator of interferon genes (STING) protein are provided. Methods involving compounds of Formula I as effective modulators of STING are also provided.

NOVEL NICOTINAMIDE DERIVATIVES OR SALTS THEREOF

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Paragraph 0563; 0564; 0697; 0698, (2018/09/08)

An object of the present invention is to provide to a compound and a pharmaceutical composition, which have excellent Syk-inhibitory activity. Th e present invention provides a nicotinamide derivative represented by the follo wing formula (I) (wherein R 1 represents a halogen atom; R 2 represents a C 1-12 alkyl group, a C 2-12 alkenyl group, a C 2-12 alkynyl group, a C 3-8 cycloalkyl g roup, an aryl group, an ar-C 1-6 alkyl group or a heterocyclic group, each opti onally having at least one substituent; R 3 represents an aryl group or a hetero cyclic group each optionally having at least one substituent; and R 4 and R 5 e ach independently represent a hydrogen atom; and R 2 and R 4 may form a cyc lic amino group optionally having at least one substituent together with the ni trogen atom to which they bind) or a salt thereof, and a pharmaceutical comp osition for use in the treatment of a Syk-related disease which comprises the nicotinamide derivative or a salt thereof.

A scalable and safe continuous flow procedure for in-line generation of diazomethane and its precursor MNU

Lehmann

supporting information, p. 1449 - 1453 (2017/05/10)

Diazomethane is a valuable C1-building block for organic synthesis. Due to its intrinsic reactivity and instability, handling of this reagent is associated with serious safety hazards. Herein we present a simple and robust continuous flow process, allowing a safe and on-demand generation of diazomethane with a productivity of 95-117 mmol h-1. The developed two-step process starts from non-hazardous N-methylurea, and generates and consumes N-methyl-N-nitrosourea (MNU) and diazomethane, thus enabling a safe and convenient scale-up to a multi-gram scale in a conventional synthesis laboratory.

Discovery of a 1-Methyl-3,4-dihydronaphthalene-Based Sphingosine-1-Phosphate (S1P) Receptor Agonist Ceralifimod (ONO-4641). A S1P1 and S1P5 Selective Agonist for the Treatment of Autoimmune Diseases

Kurata, Haruto,Kusumi, Kensuke,Otsuki, Kazuhiro,Suzuki, Ryo,Kurono, Masakuni,Komiya, Takaki,Hagiya, Hiroshi,Mizuno, Hirotaka,Shioya, Hiroki,Ono, Takeji,Takada, Yuka,Maeda, Tatsuo,Matsunaga, Norikazu,Kondo, Tetsu,Tominaga, Sachiko,Nunoya, Ken-Ici,Kiyoshi, Hidekazu,Komeno, Masaharu,Nakade, Shinji,Habashita, Hiromu

, p. 9508 - 9530 (2017/12/26)

The discovery of 1-({6-[(2-methoxy-4-propylbenzyl)oxy]-1-methyl-3,4-dihydronaphthalen-2-yl}methyl)azetidine-3-carboxylic acid 13n (ceralifimod, ONO-4641), a sphingosine-1-phosphate (S1P) receptor agonist selective for S1P1 and S1P5, is described. While it has been revealed that the modulation of the S1P1 receptor is an effective way to treat autoimmune diseases such as relapsing-remitting multiple sclerosis (RRMS), it was also reported that activation of the S1P3 receptor is implicated in some undesirable effects. We carried out a structure-activity relationship (SAR) study of hit compound 6 with an amino acid moiety in the hydrophilic head region. Following identification of a lead compound with a dihydronaphthalene central core by inducing conformational constraint, optimization of the lipophilic tail region led to the discovery of 13n as a clinical candidate that exhibited >30 000-fold selectivity for S1P1 over S1P3 and was potent in a peripheral lymphocyte lowering (PLL) test in mice (ED50 = 0.029 mg/kg, 24 h after oral dosing).

Structure-Guided Optimization of HIV Integrase Strand Transfer Inhibitors

Zhao, Xue Zhi,Smith, Steven J.,Maskell, Daniel P.,Métifiot, Mathieu,Pye, Valerie E.,Fesen, Katherine,Marchand, Christophe,Pommier, Yves,Cherepanov, Peter,Hughes, Stephen H.,Burke, Terrence R.

, p. 7315 - 7332 (2017/09/22)

Integrase mutations can reduce the effectiveness of the first-generation FDA-approved integrase strand transfer inhibitors (INSTIs), raltegravir (RAL) and elvitegravir (EVG). The second-generation agent, dolutegravir (DTG), has enjoyed considerable clinical success; however, resistance-causing mutations that diminish the efficacy of DTG have appeared. Our current findings support and extend the substrate envelope concept that broadly effective INSTIs can be designed by filling the envelope defined by the DNA substrates. Previously, we explored 1-hydroxy-2-oxo-1,2-dihydro-1,8-naphthyridine-3-carboxamides as an INSTI scaffold, making a limited set of derivatives, and concluded that broadly effective INSTIs can be developed using this scaffold. Herein, we report an extended investigation of 6-substituents as well the first examples of 7-substituted analogues of this scaffold. While 7-substituents are not well-tolerated, we have identified novel substituents at the 6-position that are highly effective, with the best compound (6p) retaining better efficacy against a broad panel of known INSTI resistant mutants than any analogues we have previously described.

TrkA KINASE INHIBITORS, COMPOSITIONS AND METHODS THEREOF

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Page/Page column 76, (2016/05/02)

The present invention is directed to substituted indole compounds of formula (I) which are tropomyosin-related kinase (Trk) family protein kinase inhibitors, and hence are useful in the treatment of pain, inflammation, cancer, restenosis, atherosclerosis, psoriasis, thrombosis, adisease, disorder, injury, or malfunction relating to dysmyelination or demyelination or a disease or disorder associated with abnormal activities of nerve growth factor (NGF) receptor TrkA.

Effects of the pyridine 3-substituent on regioselectivity in the nucleophilic aromatic substitution reaction of 3-substituted 2,6-dichloropyridines with 1-methylpiperazine studied by a chemical design strategy

Bach, Peter,Marczynke, Michaela,Giordanetto, Fabrizio

, p. 6940 - 6952 (2013/02/22)

A chemical design strategy has been used to select 3-substituted 2,6-dichloropyridines for the nucleophilic aromatic substitution reaction with 1-methylpiperazine. The aim was to study the dependency of the regioselectivity in these reactions on the character of the pyridine 3-substituent expressed by their lipophilicity (PI), size (MR), and inductive effect (Ip). Interestingly, the regioselectivity did not correlate with any of these parameters, but in a statistically significant manner with the Verloop steric parameter B1, as indicated by the p value of 0.006 (R2 = 0.45). This implies that bulky 3-substituents close to the pyridine ring induce regioselectivity towards the 6-position. Useful in practical synthesis is the different regioselectivity obtained with a carboxylic acid 3-substituent and precursors or derivatives thereof. Thus, in acetonitrile as solvent, 3-carboxylate and 3-amide substituents were preferred to obtain the 2-isomer (9:1 ratio of the 6-isomer), whereas the 3-cyano and 3-trifluoromethyl substitutents were preferred to obtain the 6-isomer (9:1 ratio of the 2-isomer). Analysis of the regioselectivity Rsel for the pyridine 2-position in the reaction of 2,6-dichloro-3-(methoxycarbonyl)pyridine with 1-methylpiperazine in 21 different solvents showed that Rsel could be predicted by the Kamlet-Taft equation: Rsel = 1.28990 + 0.03992α - 0.59417β - 0.46169π* (R2 = 0.95, p = 1.9 × 10-10). Rsel is thus mainly correlated with the ability of the solvent to function as a hydrogen-bond acceptor, as expressed by the solvatochromic β parameter. Thus, the 16:1 regioselectivity for the 2-isomer in DCM (β = 0.10) could be switched to a 2:1 selectivity for the 6-isomer in DMSO (β = 0.76). Copyright

NICOTINAMIDES AS JAK KINASE MODULATORS

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Page/Page column 43, (2012/05/07)

The present invention is directed to compounds of formula I and pharmaceutically acceptable salts, esters, and prodrugs thereof which are inhibitors of JAK kinase. The present invention is also directed to intermediates used in making such compounds, the preparation of such a compound, pharmaceutical compositions containing such a compound, methods of inhibition JAK kinase activity, methods of inhibition the platelet aggregation, and methods to prevent or treat a number of conditions mediated at least in part by JAK kinase activity, such as undesired thrombosis and Non Hodgkin's Lymphoma.

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