4-Fluoro-7-azaindole

Base Information

• Chemical Name: 4-Fluoro-7-azaindole
• CAS No.: 640735-23-5
• Molecular Formula: C7H5FN2
• Molecular Weight: 136.129
• Hs Code.: 2933998090
• DSSTox Substance ID: DTXSID80461514
• Nikkaji Number: J1.994.511A
• Wikidata: Q72479059
• Mol file: 640735-23-5.mol

Synonyms:4-Fluoro-7-azaindole;640735-23-5;4-fluoro-1H-pyrrolo[2,3-b]pyridine;MFCD08272231;1H-PYRROLO[2,3-B]PYRIDINE, 4-FLUORO-;SCHEMBL1467702;DTXSID80461514;YZTWCWYRUCKWDR-UHFFFAOYSA-N;CS-B0842;AKOS005145754;PB15996;4-fluoranyl-1H-pyrrolo[2,3-b]pyridine;DS-10880;AM20061859;FT-0660880;A834632;J-515326

Chemical Property of 4-Fluoro-7-azaindole

Chemical Property:

• Appearance/Colour: Off-White Solid
• Melting Point: 118-120°C
• PKA: 13.28±0.40(Predicted)
• Density: 1.370±0.06 g/cm3(Predicted)
• Storage Temp.: Refrigerator
• Solubility.: Dichloromethane, Ethyl Acetate, Methanol, THF
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 136.04367633
• Heavy Atom Count: 10
• Complexity: 129

Purity/Quality:

98%,99%, ^*data from raw suppliers

4-Fluoro-7-azaindole ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CNC2=NC=CC(=C21)F
• Uses: 4-Fluoro-7-azaindole (cas# 640735-23-5) is a compound useful in organic synthesis.

Technology Process of 4-Fluoro-7-azaindole

There total 10 articles about 4-Fluoro-7-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: 100.0%

4-fluoro-1-[tris(propan-2-yl)silyl]-1H-pyrrolo[2,3-b]pyridine (640735-25-7) → 4-fluoro-1H-pyrrolo[2,3-b]pyridine (640735-23-5)

Guidance literature:

With tetrabutyl ammonium fluoride;

DOI:10.1021/ol036030z

Reference yield: 44.0%

4-amino-1H-pyrrolo<2,3-b>pyridine (74420-00-1) → 1H-pyrrolo<2,3-b>pyridin-4-ol (1,7-Dideazahypoxanthine) (74420-02-3) + 4-fluoro-1H-pyrrolo[2,3-b]pyridine (640735-23-5)

Guidance literature:

With tetrafluoroboric acid; sodium nitrite; In water; at 0 - 20 ℃; for 22h;

DOI:10.1021/ol036030z

Reference yield:

4-chloro-7-azaindole (55052-28-3) → 4-fluoro-1H-pyrrolo[2,3-b]pyridine (640735-23-5)

Guidance literature:

Multi-step reaction with 4 steps

1.1: AcCl; NaI / acetonitrile / Heating

1.2: 52 percent / aq. NaOH / tetrahydrofuran / 40 °C

2.1: 99 percent / NaH / tetrahydrofuran / Heating

3.1: n-butyllithium / diethyl ether / -78 °C

3.2: 71 percent / N-fluorobenzenesulfonimide / tetrahydrofuran / -78 °C

4.1: 100 percent / TBAF / tetrahydrofuran / 20 °C

With n-butyllithium; tetrabutyl ammonium fluoride; sodium hydride; acetyl chloride; sodium iodide; In tetrahydrofuran; diethyl ether; acetonitrile;

DOI:10.1016/j.tetlet.2007.01.003

upstream raw materials:

4-amino-1H-pyrrolo<2,3-b>pyridine

4-fluoro-1-[tris(propan-2-yl)silyl]-1H-pyrrolo[2,3-b]pyridine

4-iodo-1H-pyrrolo[2,3-b]pyridine

4-iodo-1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridine

Downstream raw materials:

4-fluoro-3-nitro-1H-pyrrolo[2,3-b]pyridine

Refernces

• 1、 -. "OXADIAZINE COMPOUNDS AND METHODS OF USE THEREOF". Paragraph 0722. . Retrieved 2017/03/14.
• 2、 Thibault, Carl,L'Heureux, Alexandre,Bhide, Rajeev S.,Ruel, Rejean. "Concise and Efficient Synthesis of 4-Fluoro-1H-pyrrolo[2,3-b]pyridine". . p. 5023 - 5025. Retrieved 2007/10/03.