6-Azaindole

Base Information

• Chemical Name: 6-Azaindole
• CAS No.: 271-29-4
• Molecular Formula: C7H6N2
• Molecular Weight: 118.138
• Hs Code.: 29339980
• European Community (EC) Number: 664-233-5
• DSSTox Substance ID: DTXSID20181562
• Nikkaji Number: J1.862.984D,J72.956F
• Wikidata: Q72444314
• Mol file: 271-29-4.mol

Synonyms:6-azaindole

Chemical Property of 6-Azaindole

Chemical Property:

• Appearance/Colour: off-white to yellowish crystalline powder
• Vapor Pressure: 0.003mmHg at 25°C
• Melting Point: 136-137 °C
• Refractive Index: 1.697
• Boiling Point: 295.761 °C at 760 mmHg
• PKA: 14.66±0.30(Predicted)
• Flash Point: 137.4 °C
• PSA: 28.68000
• Density: 1.242 g/cm³
• LogP: 1.56290
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• Sensitive.: Air & Light Sensitive
• Water Solubility.: Soluble in water (hardly), methanol and chloroform.
• XLogP3: 1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 118.053098200
• Heavy Atom Count: 9
• Complexity: 103

Purity/Quality:

99% ^*data from raw suppliers

6-Azaindole ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CNC2=C1C=CN=C2
• Uses: 6-Azaindole is an indole derivative and useful synthetic intermediate.

Technology Process of 6-Azaindole

There total 16 articles about 6-Azaindole 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: 97.0%

tert-butyl 2-hydroxy-2,3-dihydro-1H-pyrrolo[2,3-c]pyridine-1-carboxylate (185139-01-9) → 6-azaindole (271-29-4)

Guidance literature:

With hydrogenchloride; In tetrahydrofuran; at 50 ℃; for 4.5h;

DOI:10.1055/s-1996-4312

Reference yield: 88.0%

(E)-3-amino-2-(2-ethoxyethenyl)pyridine (146336-81-4) → 6-azaindole (271-29-4)

Guidance literature:

With hydrogenchloride; In methanol; for 2h; Heating;

Reference yield: 86.0%

7-chloro-1H-pyrrolo[2,3-c]pyridine (357263-41-3) → 6-azaindole (271-29-4)

Guidance literature:

With hydrogen; In ethanol; under 1551.49 - 2068.65 Torr;

DOI:10.1021/jo0111614

upstream raw materials:

1H-pyrrolo[2,3-c]pyridine-3-carboxylic acid

(2,2-diethoxy-ethyl)-pyrrol-2-ylmethylen-amine

(E)-3-amino-2-(2-ethoxyethenyl)pyridine

tert-butyl 2-hydroxy-2,3-dihydro-1H-pyrrolo[2,3-c]pyridine-1-carboxylate

Refernces

• 1、 Adler,Albert. "-". . p. 1794. Retrieved 1960.
• 2、 Lee, Hsueh-Yun,Tsai, An-Chi,Chen, Mei-Chuan,Shen, Po-Jung,Cheng, Yun-Ching,Kuo, Ching-Chuan,Pan, Shiow-Lin,Liu, Yi-Min,Liu, Jin-Fen,Yeh, Teng-Kuang,Wang, Jing-Chi,Chang, Chi-Yen,Chang, Jang-Yang,Liou, Jing-Ping. "Azaindolylsulfonamides, with a more selective inhibitory effect on histone deacetylase 6 activity, exhibit antitumor activity in colorectal cancer HCT116 cells". . p. 4009 - 4022. Retrieved 2014/06/09.
• 3、 Blaazer, Antoni R.,Lange, Jos H.M.,Van Der Neut, Martina A.W.,Mulder, Arie,Den Boon, Femke S.,Werkman, Taco R.,Kruse, Chris G.,Wadman, Wytse J.. "Novel indole and azaindole (pyrrolopyridine) cannabinoid (CB) receptor agonists: Design, synthesis, structure-activity relationships, physicochemical properties and biological activity". experimental part. p. 5086 - 5098. Retrieved 2011/11/29.