1822-51-1 Usage
Description
4-(Chloromethyl)pyridine hydrochloride is a yellow to orange fine crystalline powder that serves as an important raw material and intermediate in organic synthesis, pharmaceuticals, and agrochemicals. It is known for its ability to protect the carboxyl termini of peptides as 4-picolyl esters, providing a polar 'handle' that aids in the separation and purification of peptides.
Uses
Used in Organic Synthesis:
4-(Chloromethyl)pyridine hydrochloride is used as a reagent for the protection of carboxyl termini of peptides as 4-picolyl esters. This protection allows for the separation and purification of peptides, making it a valuable component in organic synthesis processes.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 4-(Chloromethyl)pyridine hydrochloride is used as an intermediate in the synthesis of various drugs. Its ability to protect carboxyl termini of peptides makes it a crucial component in the development of new pharmaceutical compounds.
Used in Agrochemicals:
4-(Chloromethyl)pyridine hydrochloride is also applied in the agrochemical industry as an intermediate for the synthesis of various agrochemical products. Its versatility in protecting carboxyl termini of peptides contributes to the development of effective agrochemicals.
Used in Peptide Synthesis:
4-(Chloromethyl)pyridine hydrochloride is used in conjunction with Amberlyst?15 resin in peptide synthesis. The group can be introduced in the presence of a base, such as tetramethylguanidine, and is stable to acid-catalyzed removal of Cbz protecting group. It can be removed by base, Na in liquid ammonia, or catalytic hydrogenolysis, making it a valuable tool in peptide synthesis.
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.]
Check Digit Verification of cas no
The CAS Registry Mumber 1822-51-1 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 1,8,2 and 2 respectively; the second part has 2 digits, 5 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 1822-51:
(6*1)+(5*8)+(4*2)+(3*2)+(2*5)+(1*1)=71
71 % 10 = 1
So 1822-51-1 is a valid CAS Registry Number.
InChI:InChI=1/C6H6ClN/c7-5-6-1-3-8-4-2-6/h1-4H,5H2
1822-51-1Relevant articles and documents
A 4 - chloromethyl pyridine hydrochloride synthetic method
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, (2019/06/05)
The invention belongs to the field of organic synthesis, in particular to a 4 - chloromethyl pyridine hydrochloride synthetic method, the method comprises the following steps: (1) to 4 - methyl pyridine as raw materials, takes water as a solvent, the potassium permanganate oxide it to 4 - pyridine carboxylic acid, wherein 4 - methyl pyridine with potassium permanganate in a molar ratio of 1: 2.1 - 2.3, the oxidation temperature is 75 - 80 °C, heating 35 min, the reaction is complete the reaction liquid is adjusted to be acidic, and then cooling and filtering to obtain 4 - pyridine carboxylic acid; (2) 4 - pyridine carboxylic acid with methanol under acidic conditions to produce the 4 - pyridine carboxylic acid methyl ester, wherein the 4 - pyridine carboxylic acid with methanol in a molar ratio of 1: 1.3; (3) reduction of 4 - pyridine carboxylic acid methyl ester for 4 - pyridine methanol; (4) 4 - pyridine methanol with thionyl chloride reaction to obtain the target product 4 - chloromethyl pyridine hydrochloride, 4 - pyridine methanol with thionyl chloride in a molar ratio of 1: 1.1 - 1.3.
Facile and Selective Synthesis of Chloromethylpyridines and Chloropyridines Using Diphosgene/Triphosgene
Narendar,Gangadasu,Ramesh, Ch.,Raju, B. China,Rao, V. Jayathirtha
, p. 1097 - 1103 (2007/10/03)
Diphosgene and triphosgene in the presence of amines were found to be an excellent chlorinating agents with high selectivity for the preparation of chloromethylpyridines and chloropyridines from picoline-N-oxides and pyridine-N-oxides respectively.
Novel 1,4-benzothiazephine and 1,5-benzothiazepine compounds as inhibitors of apical sodium co-dependent bile acid transport and taurocholate uptake
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, (2008/06/13)
Compounds, pharmaceutical compositions, and methods for the treatment of a hyperlipidemic condition in a subject. The compounds of the present invention are apical sodium co-dependent bile acid transport inhibitors and are 1,4-benzothiazepine and 1,5-benzothiazepine compounds corresponding to Formula I: wherein j, m, Y, Z, R1A, R1B, R2A, R2B and R6 are as defined in the specification.