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2,5-Dichloropyridine

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2,5-Dichloropyridine Basic information
Uses
Product Name:2,5-Dichloropyridine
Synonyms:2,5-Dichloropyridine, 98% 5GR;2,5- twochlorine pyridine;2,5-Dichiloropyridine;2,5-Chloro pyridine;2,5-dichloro-pyridin;2,5-DICHLORPYRIDINE;2,5-Dichloropyridine97%;Dichloropyridine
CAS:16110-09-1
MF:C5H3Cl2N
MW:147.99
EINECS:240-278-2
Product Categories:Chlorinated heterocyclic series;Pyridines, Pyrimidines, Purines and Pteredines;Halides;Pyridines;Chloropyridines;Halopyridines;Boronic Acid;C5Heterocyclic Building Blocks;Halogenated Heterocycles;Heterocyclic Building Blocks;Pyridine;pyridine derivative;Building Blocks;C5;Chemical Synthesis;Halogenated Heterocycles;Heterocyclic Building Blocks;alkyl chloride;bc0001
Mol File:16110-09-1.mol
2,5-Dichloropyridine Structure
2,5-Dichloropyridine Chemical Properties
Melting point 59-62 °C (lit.)
Boiling point 190-191 °C
density 1.5159 (rough estimate)
refractive index 1.5500 (estimate)
Fp 112 °C
storage temp. Inert atmosphere,Room Temperature
pka-2.25±0.10(Predicted)
form Crystalline Solid
color White to slightly yellow
Water Solubility insoluble
BRN 108886
InChIInChI=1S/C5H3Cl2N/c6-4-1-2-5(7)8-3-4/h1-3H
InChIKeyGCTFDMFLLBCLPF-UHFFFAOYSA-N
SMILESC1(Cl)=NC=C(Cl)C=C1
CAS DataBase Reference16110-09-1(CAS DataBase Reference)
Safety Information
Hazard Codes Xi,Xn
Risk Statements 36/37/38-22
Safety Statements 26-37/39-36
RIDADR UN2811
WGK Germany 3
RTECS US8225000
Hazard Note Harmful
HazardClass IRRITANT
HazardClass 6.1
HS Code 29333990
Storage Class11 - Combustible Solids
Hazard ClassificationsEye Irrit. 2
Skin Irrit. 2
STOT SE 3
MSDS Information
ProviderLanguage
2,5-Dichloropyridine English
SigmaAldrich English
ACROS English
ALFA English
2,5-Dichloropyridine Usage And Synthesis
Uses2,5-Dichloropyridine is a reagent used in chemical synthesis. It has been used to synthesize 4-benzodiazepine-2,5 diones as Hdm2 antagonists and inhibitors of ERK protein kinase.
Chemical Propertieswhite to slightly yellow crystalline solid
Uses2,5-Dichloropyridine was used in the synthesis of 6-halo-pyridin-3-yl boronic acids and esters. It undergoes cross-coupling reaction with arylboronic acids in the presence of [1,4-bis-(diphenylphosphine)butane]palladium (II) dichloride as catalyst.
Synthesis Reference(s)Synthetic Communications, 20, p. 2971, 1990 DOI: 10.1080/00397919008051514
General Description2,5-Dichloropyridine undergoes cross-coupling reaction with arylboronic acids in the presence of [1,4-bis-(diphenylphosphine)butane]palladium (II) dichloride as catalyst.
Synthesis
2,5-Dibromopyridine

624-28-2

2,5-Dichloropyridine

16110-09-1

General procedure for the synthesis of 2,5-dichloropyridine from 2,5-dibromopyridine: Catalyst 1 (10 mol%), 2,5-dibromopyridine (1.0 mmol), tetramethylammonium chloride (Me4NCl, 2.0 mmol), and ethanol (EtOH, 2.0 mL) were added to a Schlenk tube under nitrogen protection. Schlenk tubes were sealed using polytetrafluoroethylene (Teflon) valves and the reaction mixture was stirred at 100 °C. The reaction process was monitored by gas chromatography (GC) analysis. After completion of the reaction, the solvent was removed under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent ratio petroleum ether/ethyl acetate = 10:1) to give 2,5-dichloropyridine. The yield of the product was determined by high-resolution gas chromatography-mass spectrometry (GC-MS) analysis and the structure was confirmed by comparing its physical properties and spectral data with known compounds.

References[1] Applied Catalysis A: General, 2014, vol. 472, p. 178 - 183
[2] Chemical Communications, 2012, vol. 48, # 76, p. 9468 - 9470
Tag:2,5-Dichloropyridine(16110-09-1) Related Product Information
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