| Identification | More | [Name]
4-(Chloromethyl)pyridine hydrochloride | [CAS]
1822-51-1 | [Synonyms]
4-(CHLOROMETHYL)PYRIDINE HYDROCHLORIDE
4-(CHLOROMETHYL)PYRIDINIUM CHLORIDE
4-PICOLYL CHLORIDE HYDROCHLORIDE
TIMTEC-BB SBB003917
4-Picolyl chloride HCl (65% in water)
4-(Chloromethyl)pyridine HCL
4-Plcolyl Chloride Hydrochloride
Pyridine, 4-(chloromethyl)-, hydrochloride
4-Picolyl chloride
4-PICOLYL CHLORIDE HYDROCHLORIDE 98+%
4-PICOLYLCHLORIDE 4-CHLOROMETHYL PYRIDINE
4-CHLOROMETHYLPYRIDINE HYDROCHLORIDE (4-PICOLYLCHLORIDE HYDROCHLORIDE)
4-(Chloromethyl) Pyridine HCL 99%
4-(Chloromethyl)pyridine hydrochloride ,98%
4-Chloromethylpyridine hydrochloride (4-Picolylchloride hydrochl | [EINECS(EC#)]
217-350-7 | [Molecular Formula]
C6H7Cl2N | [MDL Number]
MFCD00012826 | [Molecular Weight]
164.03 | [MOL File]
1822-51-1.mol |
| Chemical Properties | Back Directory | [Appearance]
YELLOW TO ORANGE FINE CRYSTALLINE POWDER | [Melting point ]
166-173 °C(lit.) | [storage temp. ]
2-8°C
| [solubility ]
soluble in DMSO, Methanol | [form ]
Fine Crystalline Powder | [color ]
Yellow to orange | [Water Solubility ]
750 g/L (20 ºC) | [Sensitive ]
Hygroscopic | [Detection Methods]
T,NMR | [BRN ]
3689154 | [InChI]
InChI=1S/C6H6ClN.ClH/c7-5-6-1-3-8-4-2-6;/h1-4H,5H2;1H | [InChIKey]
ZDHKVKPZQKYREU-UHFFFAOYSA-N | [SMILES]
C1=NC=CC(CCl)=C1.[H]Cl | [CAS DataBase Reference]
1822-51-1(CAS DataBase Reference) | [Storage Precautions]
Moisture sensitive |
| Safety Data | Back Directory | [Symbol(GHS) ]
GHS05 | [Signal word ]
Danger | [Hazard statements ]
H314 | [Precautionary statements ]
P260-P280-P303+P361+P353-P304+P340+P310-P305+P351+P338-P363 | [Hazard Codes ]
C,Xi | [Risk Statements ]
R34:Causes burns.
R4:Forms very sensitive explosive metallic compounds.
R22:Harmful if swallowed.
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
S36:Wear suitable protective clothing . | [RIDADR ]
UN 3261 8/PG 3
| [WGK Germany ]
3
| [F ]
3-10 | [Hazard Note ]
Corrosive | [HazardClass ]
8 | [PackingGroup ]
III | [HS Code ]
29333999 | [Storage Class]
8A - Combustible corrosive hazardous materials | [Hazard Classifications]
Skin Corr. 1B |
| Hazard Information | Back Directory | [Chemical Properties]
YELLOW TO ORANGE FINE CRYSTALLINE POWDER | [Uses]
It finds its application as a reagent for protection of carboxyl termini of peptides as 4-picolyl esters, providing a polar 'handle' which aids in separation and purification of the peptide. The group can be introduced in the presence of a base, e.g. tetramethylguanidine, is stable to acid-catalyzed removal of Cbz protecting group and can be removed by base, Na in liquid ammonia or catalytic hydrogenolysis. It is also applied in conjunction with Amberlyst?15 resin in peptide synthesis. It is an important raw material and intermediate used in organic synthesis, pharmaceuticals and agrochemicals. | [Application]
4-Picolyl Chloride Hydrochloride is used for protection of alcohols, phenols, thiols, and carboxylic acids. | [Synthesis]
Synthesis of 4-chloromethylpyridine hydrochloride (21): 4-Pyridine methanol (20) (54.4 g, 0.50 mol) was dissolved in 202 ml of acetonitrile. The solution was slowly added dropwise to a mixed solution containing thionyl chloride (65.3 g, 0.55 mol) and acetonitrile (109 ml) at 50 °C. After the dropwise addition was completed, the reaction mixture was continued to be stirred at 50 °C for 1 hour. After completion of the reaction, the mixture was cooled to room temperature to give a slurry product (quantitative yield) of 4-chloromethylpyridine hydrochloride (21). The product was characterized by 1H-NMR (DMSO-d6, with TMS as internal standard): δ 5.09 (s, 2H), 8.09 (d, J = 6.6 Hz, 2H), 8.94 (d, J = 6.6 Hz, 2H). | [storage]
The free base is reported to be unstable, and should be
generated shortly before use. | [Purification Methods]
Purify it by recrystallisation from EtOH or EtOH/dry Et2O. It melts between 171o and 175o, and the clear melt resolidifies on further heating at 190o and turns red to black at 280o but does not melt again. The picrate-hydrochloride (prepared in EtOH) has m 146-147o. The free base is an oil. [Mosher & Tessieri J Am Chem Soc 73 4925 1951, Beilstein 20 III/IV 2752.] | [References]
[1] Patent: US2003/195363, 2003, A1. Location in patent: Page/Page column 13
[2] Patent: US6057448, 2000, A
[3] ChemMedChem, 2015, vol. 10, # 11, p. 1875 - 1883 |
|
| Company Name: |
J & K SCIENTIFIC LTD.
|
| Telephone: |
18210857532 18210857532 |
| Website: |
https://www.jkchemical.com |
| Company Name: |
Alfa Aesar
|
| Telephone: |
400-6106006 |
| Website: |
http://chemicals.thermofisher.cn |
| Company Name: |
Energy Chemical
|
| Telephone: |
400-0056266 |
| Website: |
www.energy-chemical.com |
|