6-CHLOROMETHYL-2-CYANOPYRIDINE
-
6-CHLOROMETHYL-2-CYANOPYRIDINE
structure -
-
CAS No:
135450-23-6
-
Formula:
C7H5ClN2
-
Chemical Name:
6-CHLOROMETHYL-2-CYANOPYRIDINE
-
Synonyms:
6-(Chloromethyl)-2-cyanopyridine;6-Chloromethyl-2-cyanopyridine;6-(chloromethyl)pyridine-2-carbonitrile;6-(chloromethyl)picolinonitrile;6-(Chloromethyl)-2-pyridinecarbonitrile;2-Pyridinecarbonitrile, 6-(chloromethyl)-;ACMC-209xhm;KSC169S4P;SCHEMBL9297038;CTK0G9947
- Categories:
-
CAS No:
Safety Information
24/25
|Danger|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P260, P264, P270, P280, P301+P312, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P310, P321, P330, P363, P405, and P501|The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.
6-CHLOROMETHYL-2-CYANOPYRIDINE Use and Manufacturing
General procedure: 4-((5-(2-aminopyridin-3-yl)isoxazol-3-yl)methyl)phenol (Intermediate C, 80mg, 0.30mmol) was dissolved in DMF (lmL) and potassium 2-methylpropane-2-olate (1M in THF, 0.33mL, 0.33mmol) was added dropwise. The mixture was stirred for 5min and a solution of 3-(bromomethyl)-5-methylisoxazole (63.2mg, 0.36mmol) in DMF (0.5mL) was added. The resulting mixture was stirred for 30min and directly purified by column chromatography (Si02, hexane/ethyl acetate). Fraction containing the product were concentrated under reduced pressure and further purified by reversed phase flash chromatography (C18, acetonitrile/water) to yield 3-(3-(4-((lH-pyrazol-l-yl)methyl)benzyl)isoxazol-5-yl)pyridin-2-amine (7lmg, 0.20mmol, 66%) as a white solid. 400 MHz l NMR (CDCl3) d 8.13 (s, 1H), 7.70 (dd , J= 7.7, 1.8 Hz, 1H), 7.24 - 7.16 (m, 2H), 6.98 - 6.89 (m, 2H), 6.70 (dd, J= 7.7, 4.8 Hz, 1H), 6.23 (s, 1H), 6.10 (d, J= 1.1 Hz, 1H), 5.44 (s, 2H), 5.09 (s, 2H), 3.99 (s, 2H), 2.42 (d, .7= 0.9 Hz, 3H). MS: 363.3 [M+H]+.120mg of triazacyclononane protected by a monoHoc (0.4 mmol, 1 eq.) are dissolved in 50 mE of dry acetonitrile under argon with 252 mg of anhydrous anhydrous Na2CO3 (2, 4 mmol, 6 eq.). A 151 mg solution of compound 26 (1 mmol, 2.5 eq.) in dry acetonitrile is then added and the mixture is stirred for 12 hours at 60 C. under argon. After cooling, the mixture is filtered on sintered and evaporated. The residue is taken up by dichloromethane and purified on an alumina column (activity III eluent: dichloromethane followed by ethyl acetate) to give 160 mg of compound 27 in the form of a white pasty solid (R=83%). 'H-NMR (300 MHz, CDC13) oe (ppm)=7.79 (dt, 3J=8 Hz, 4J=1 Hz, 2H), 7.70 (bd, J=8 Hz, 2H), 7.57 (dt, 3J=8Hz, 4J=1 Hz, 2H), 3.91 (s, 4H), 3.36 (m, 4H), 3.03 (m, 4H), 2.66 (m, 4H), 1.47 (s, 9H). EC-MS: [M+H]=462.2 mlz.Charge Cl-nitrile (180 g) into a rector containing THF (540 g). Charge NaT (185.7 g) to the reactor and stirred at 50 C. After reaction completion, the reactor is cooled to 0 C. In another reactor, charge t-BuOK (145.6 g) and THF (320 g). Add (S)-tetrahydrofuran-3-ol (311.9 g) into the reactor while maintaining internal temperature below 50 Cto deprotonate the alcohol. Stir until t-BuOK dissolves. Add THF-OK / THF solution into 6-(iodomethyl)picolinonitrile solution (compound 6) while maintaining internal temperature below 10 C. Stir at room temperature until reaction completion. Concentrate the solution to remove THF solvent. Add ethyl acetate (630 g) and wash by water (420 g). Extract water phase by ethyl acetate (630 g). Combine organic layer and concentrate to obtain oil crude 374 g. The residue was distilled under vaccum (P=3-4 torr, internal temperature 174 C to 188 C) to obtain (S)-6-(((tetrahydrofuran-3-yl)oxy)methyl)picolinonitrile (compound 7) as an oily product (204g, >96% purity; 74% yield)
6-(Chloromethyl)-2-pyridinecarbonitrile is used in the preparation of thiazole derivatives as antiulcer and antimicrobial agents.
Computed Properties
Molecular Weight:152.58
XLogP3:0.9
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:1
Exact Mass:152.0141259
Monoisotopic Mass:152.0141259
Topological Polar Surface Area:36.7
Heavy Atom Count:10
Complexity:149
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
Recommended Suppliers of 6-CHLOROMETHYL-2-CYANOPYRIDINE
-
![China]()
CN
5 YRS
Business licensedTrader Supplier of Intermediates,Building blocks,API,Silicones,Peptides,Lab chemicals,Biochemicals,Pharmaceuticals,Screening Compounds,Food Additives -
![China]()
CN
8 YRS
Business licensedDistributor Supplier of Garenoxacinmesylatehydrate,Ethyl7-bromo-1-cyclopropyl-8-(difluoromethoxy)-4-o,(R)-5-bromo-1-methyl-2-Tritylisoindoline,(R)-(1-methyl-2-trityl-isoindolin-5-yl)boronicacid,(R)-2-(1-methyl-2-trityl-isoindolin-5-yl)-1,3,6,2-InquiryCAS No.: 135450-23-6Grade: Pharmaceutical GradeContent: 98% -
![China]()
CN
5 YRS
Business licensedTrader Supplier of Peptides,Chemicals,API,AdditivesInquiryCAS No.: 135450-23-6Grade: Pharmaceutical GradeContent: 99% -
![China]()
CN
3 YRS
Business licensed Certified factoryManufactory Supplier of Dyes,Textile agent,Medical intermediate,API,Pigments,Basic Chemicals
Learn More Other Chemicals
-
(2E)-3-(1-METHYL-1H-PYRROL-2-YL)ACRYLIC ACID
51485-76-8
-
Benadryl N-oxide hydrochloride
13168-00-8
-
6-CHLORO-3-IODO-IMIDAZO[1,2-A]PYRIDINE
885275-59-2
-
(2-Bromophenyl)diphenylphosphine Formula
62336-24-7
-
1-Morpholinocyclopentene Formula
936-52-7
-
4-[2-(Boc-amino)ethoxy]-benzoic acid Formula
168892-66-8
-
3-amino-5-bromopyridine-2-carboxylic acid Structure
870997-85-6
-
2-Amino-6-methylpyridine Structure
1824-81-3
-
What is 3-Bromo-2-methylthiophene
30319-05-2
-
What is THIOPHEN-2-YLMETHYL-PHOSPHONICACIDDIETHYLESTER
2026-42-8