41789-37-1

Basic information

• Product Name: 2,6-DICHLORO-3-(CHLOROMETHYL)PYRIDINE
• Synonyms: 2,6-DICHLORO-3-(CHLOROMETHYL)PYRIDINE;2,6-Dichloro-3-picolyl chloride;2,6-Dichloro-3-pyridylmethyl chloride;3-(Chloromethyl)-2,6-dichloropyridine;PYRIDINE, 2,6-DICHLORO-3-(CHLOROMETHYL)-;2,6-Dichlor-3-chlormethylpyridine
• CAS NO: 41789-37-1
• Molecular Formula: C₆H₄Cl₃N
• Molecular Weight: 196.46
• EINECS: 604-604-1
• Mol File: 41789-37-1.mol
• Article Data: 5

Chemical Properties

• Melting Point: 89-90°
• Boiling Point: 285.5 °C at 760 mmHg
• Flash Point: 153.7 °C
• Appearance: /
• Density: 1.463
• Vapor Pressure: 0.00479mmHg at 25°C
• Refractive Index: 1.567
• Storage Temp.: 2-8°C
• PKA: -3.34±0.10(Predicted)
• CAS DataBase Reference: 2,6-DICHLORO-3-(CHLOROMETHYL)PYRIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,6-DICHLORO-3-(CHLOROMETHYL)PYRIDINE(41789-37-1)
• EPA Substance Registry System: 2,6-DICHLORO-3-(CHLOROMETHYL)PYRIDINE(41789-37-1)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 41789-37-1(Hazardous Substances Data)

Usage

General Description

2,6-Dichloro-3-(chloromethyl)pyridine, also known as DCP, is a chemical compound with the molecular formula C7H5Cl3N. It is a chlorinated derivative of pyridine and is commonly used as an intermediate in the synthesis of pharmaceuticals, agrochemicals, and other organic compounds. DCP is a white crystalline solid with a strong, pungent odor and is highly soluble in organic solvents. It is classified as a hazardous substance due to its potential for causing skin and eye irritation, and it is also considered to be toxic to aquatic organisms. Additionally, DCP is a known mutagen and may pose risks to human health and the environment if not handled properly.

InChI:InChI=1/C6H4Cl3N/c7-3-4-1-2-5(8)10-6(4)9/h1-2H,3H2

Upstream product

• 55304-90-0 2,6-dichloro-3-(hydroxymethyl)pyridine 
• 55304-73-9 2,6-dichloro-pyridine-3-carbaldehyde 
• 873-41-6 3,5,6-trichlorotriazine 
• 557-40-4 Allyl ether 
• 22162-53-4 10,11-dihydro-5H-benzo[e]pyrrolo[1,2-a][1,4]diazepine 

Downstream Products

• 1255701-21-3 (R)-8-chloro-4-methyl-2-phenyl-2,3,4,5-tetrahydropyrido[3,2-f][1,4]oxazepine 
• 1255701-22-4 (R)-2-(((2,6-dichloropyridin-3-yl)methyl)(methyl)amino)-1-phenylethanol 
• 1255701-25-7 (R)-8-chloro-2-phenyl-2,3,4,5-tetrahydropyrido[3,2-f][1,4]oxazepine 
• 1375706-15-2 (R)-4-Methyl-N-(5-(4-methyl-1H-imidazol-1-yl)pyridin-2-yl)-2-phenyl-2,3,4,5-tetrahydropyrido[3,2-f][1,4]oxazepin-8-amine 
• 1375706-18-5 (R)-4-Methyl-N-(5-(1-methyl-1H-pyrazol-4-yl)pyridin-2-yl)-2-phenyl-2,3,4,5-tetrahydropyrido[3,2-f][1,4]oxazepin-8-amine 
• 1375707-05-3 (R)-5-(2-Methoxy-6-(4-methyl-2-phenyl-2,3,4,5-tetrahydropyrido[3,2-f][1,4]oxazepin-8-ylamino)pyridin-3-yl)-1-methylpyridin-2(1H)-one 
• 1375707-17-7 (2R)-N-[6-Methoxy-5-(2-methyloxazol-5-yl)-2-pyridyl]-4-methyl-2-phenyl-3,5-dihydro-2H-pyrido[3,2-f][1,4]oxazepin-8-amine 
• 1375707-38-2 (2R)-N-[6-Methoxy-5-(1H-pyrazol-4-yl)-2-pyridyl]-4-methyl-2-phenyl-3,5-dihydro-2H-pyrido[3,2-f][1,4]oxazepin-8-amine 
• 1375711-77-5 tert-butyl 4-[2-methoxy-6-[[(2R)-4-methyl-2-phenyl-3,5-dihydro-2H-pyrido[3,2-f][1,4]oxazepin-8-yl]amino]-3-pyridyl]pyrazole-1-carboxylate 
• 1255700-52-7 (R)-2-(8-(4-(6,7-dihydro-5H-pyrrolo[2,1-c][1,2,4]triazol-3-yl)phenylamino)-2-phenyl-2,3-dihydropyrido[3,2-f][1,4]oxazepin-4(5H)-yl)ethanol 
• 1255701-85-9 (R)-tert-butyl 8-(3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenylamino)-2-phenyl-2,3-dihydropyrido[3,2-f][1,4]oxazepine-4(5H)-carboxylate 
• 1255701-88-2 (R)-tert-butyl 8-(6-methoxy-5-(1-methyl-1H-pyrazol-4-yl)pyridin-2-ylamino)-2-phenyl-2,3-dihydropyrido[3,2-f][1,4]oxazepine-4(5H)-carboxylate 
• 1255700-78-7 (R)-8-(3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenylamino)-N,N-dimethyl-2-phenyl-2,3-dihydropyrido[3,2-f][1,4]oxazepine-4(5H)-carboxamide 
• 1255701-90-6 (R)-tert-butyl 8-(5-(1-methyl-1H-pyrazol-4-yl)pyridin-2-ylamino)-2-phenyl-2,3-dihydropyrido[3,2-f][1,4]oxazepine-4(5H)-carboxylate 

Relevant articles and documents

Intramolecular Diels-Alder reactions from trichloro-1,2,4-triazine and 1,5- And 1,6-dienes

The initial dihydropyridines from Diels-Alder addition of dienes to trichloro-1,2,4-triazine, and loss of N2, undergo intramolecular addition with hexa-1,5-diene and cyclo-octa-1,5-diene, also [1,5]H sigmatropic shift with diallyl ether, and [1,5]H shift and partial aromatisation with cyclododeca-1,5,9-triene.

Synthesis of phantasmidine

Reaction of 6-chloro-2-fluoro-3-pyridineacetamide with 1,2- bis(trimethylsilyloxy)cyclobutene in ether saturated with hydrogen chloride afforded the keto amide in 85% yield. In the key step, treatment of the keto amide with aqueous KOH in t-BuOH resulted in a tandem intramolecular aldol reaction-intramolecular nucleophilic aromatic substitution sequence to give the tetracylic lactam in 46% yield. Reduction of the lactam with BH3 in THF gave phantasmidine in 67% yield.

Diels-Alder reactions of trichloro-1,2,4-triazine: Intramolecular additions with 1,5 and 1,6 dienes

Trichloro-1,2,4-triazine reacts with cycloheptene and cyclododecene to give the 2,6-dichloropyridine derivatives 6 and 7 via an intermediate dihydropyridine formed by Diels-Alder addition and loss of N2, and with cyclopenta-1,3-diene and indene by addition of a second molecule of alkene to the intermediate dihydropyridine. Bicyclo[2.2.1]hepta-2,5-diene and quadricyclane give mainly 2,3,6-trichloropyridine by loss of cyclopentadiene from the intermediate dihydropyridine. With hexa-1,5-diene, the dihydropyridine is trapped by an intramolecular Diels-Alder reaction, forming tricyclic compounds 17 and 18. With diallyl ether, the dihydropyridine partly undergoes intramolecular cycloaddition to give 23 and partly [1,5]-sigmatropic shift of hydrogen before intramolecular cycloaddition to give 25. With cyclododeca1,5,9-triene formation of pyridine derivatives is incomplete and the immediate precursor can be trapped with water.