Pyridine, 3-(1H-1,2,3-triazol-4-yl)- (9CI)

Base Information

• Chemical Name: Pyridine, 3-(1H-1,2,3-triazol-4-yl)- (9CI)
• CAS No.: 120241-79-4
• Molecular Formula: C7H6 N4
• Molecular Weight: 146.151
• Hs Code.: 2933998090
• Mol file: 120241-79-4.mol

Synonyms:Pyridine,3-(1H-1,2,3-triazol-4-yl)- (9CI); 1H-1,2,3-Triazole, pyridine deriv.;3-(1H-1,2,3-Triazol-4-yl)pyridine

Chemical Property of Pyridine, 3-(1H-1,2,3-triazol-4-yl)- (9CI)

Chemical Property:

• Melting Point: 180-182 °C(Solv: ethyl acetate (141-78-6); ethyl ether (60-29-7))
• Boiling Point: 386.6±17.0 °C(Predicted)
• PKA: 7.54±0.70(Predicted)
• PSA: 54.46000
• Density: 1.296±0.06 g/cm3(Predicted)
• LogP: 0.86670
• Storage Temp.: 2-8°C

Purity/Quality:

99.3% ^*data from raw suppliers

3-(1H-1,2,3-Triazol-4-yl)pyridine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 3-(1H-1,2,3-Triazol-4-yl)pyridine is a reactant used in the synthesis of 4-aryl-1H-1,2,3-triazoles which possesses more Indoleamine 2,3-dioxygenase (IDO) inhibitory potency than the most commonly used 1-methyltryptophan.

Technology Process of Pyridine, 3-(1H-1,2,3-triazol-4-yl)- (9CI)

There total 14 articles about Pyridine, 3-(1H-1,2,3-triazol-4-yl)- (9CI) which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.0%

(2RS,3SR)-2,3-dibromo-3-(pyridin-3-yl)propanoic acid → 3-(1H-1,2,3-triazol-4-yl)pyridine (120241-79-4)

Guidance literature:

With copper(l) iodide; sodium azide; caesium carbonate; sodium L-ascorbate; In dimethyl sulfoxide; at 110 ℃; for 4h; Inert atmosphere; Sealed tube;

DOI:10.1055/s-0030-1258312

Reference yield: 91.0%

3-pyridinecarboxaldehyde (500-22-1) + nitromethane (75-52-5) → 4-(3-pyridyl)-2H-1,2,3-triazole (120241-79-4)

Guidance literature:

With aluminum (III) chloride; sodium azide; In dimethyl sulfoxide; at 80 ℃; for 12h;

Reference yield: 89.0%

4-methyl-N′-(1-(pyridin-3-yl)ethylidene)benzenesulfonohydrazide (453523-36-9) → 3-(1H-1,2,3-triazol-4-yl)pyridine (120241-79-4)

Guidance literature:

With sodium azide; methanesulfonic acid; iodine; In dimethyl sulfoxide; at 100 ℃; for 3h;

DOI:10.1021/acs.joc.9b02250

upstream raw materials:

3-Ethynylpyridine

3-pyridinecarboxaldehyde

nitromethane

3-(2-nitroethenyl)pyridine

Downstream raw materials:

3-(2-(3,5-dimethoxyphenyl)-2H-1,2,3-triazol-4-yl)pyridine

4-(4-pyridin-3-yl-[1,2,3]triazol-2-yl)-benzoic acid ethyl ester

4-(1-benzyl-3-piperidyl)-2-(methoxymethyl)-1,2,3-triazole

Refernces

• 1、 Zhang, Wensheng,Kuang, Chunxiang,Yang, Qing. "Palladium-catalyzed one-pot synthesis of 4-Aryl-1 H-1,2,3-triazoles from anti-3-Aryl-2,3-dibromopropanoic acids and sodium azide". . p. 283 - 287. Retrieved 2010.
• 2、 Shu, Wen-Ming,Zhang, Xun-Fang,Zhang, Xiang-Xiang,Li, Min,Wang, An-Jing,Wu, An-Xin. "Metal-Free Cascade [4 + 1] Cyclization Access to 4-Aryl- NH-1,2,3-triazoles from N-Tosylhydrazones and Sodium Azide". . p. 14919 - 14925. Retrieved 2019/11/11.
• 3、 -. "Method for preparing 4-aryl-NH-1,2,3-triazole by aid of aldehyde and sodium bisulfite adduct". Paragraph 0024. . Retrieved 2017/01/02.