6-(Trifluoromethyl)nicotinonitrile

Base Information

• Chemical Name: 6-(Trifluoromethyl)nicotinonitrile
• CAS No.: 216431-85-5
• Molecular Formula: C7H3F3N2
• Molecular Weight: 172.109
• Hs Code.: 29333990
• European Community (EC) Number: 623-840-5
• DSSTox Substance ID: DTXSID50380561
• Nikkaji Number: J995.238A
• Wikidata: Q72512140
• Mol file: 216431-85-5.mol

Synonyms:6-(Trifluoromethyl)nicotinonitrile;216431-85-5;5-cyano-2-(trifluoromethyl)pyridine;6-(trifluoromethyl)pyridine-3-carbonitrile;3-Pyridinecarbonitrile, 6-(trifluoromethyl)-;MFCD03001347;3-Cyano-6-(trifluoromethyl)pyridine;6-(Trifluoromethyl)-3-pyridinecarbonitrile;6-Trifluoromethyl-nicotinonitrile;SCHEMBL524167;6-Trifluoromethylnicotinonitrile;3-cyano-6-trifluoromethylpyridine;AMY3037;DTXSID50380561;BCP21706;CS-D0795;GEO-02389;AKOS005063491;AB12807;AC-2450;FS-1207;SY001241;A4650;C2698;FT-0620832;6-(Trifluoromethyl)pyridine-3-carbonitrile, 97%;W-200223

Chemical Property of 6-(Trifluoromethyl)nicotinonitrile

Chemical Property:

• Melting Point: 37-41 °C(lit.)
• Boiling Point: 200.8 °C at 760 mmHg
• PKA: -2.89±0.22(Predicted)
• Flash Point: 75.2 °C
• PSA: 36.68000
• Density: 1.37 g/cm³
• LogP: 1.97208
• Storage Temp.: Inert atmosphere,Room Temperature
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 0
• Exact Mass: 172.02483259
• Heavy Atom Count: 12
• Complexity: 202

Purity/Quality:

98% ^*data from raw suppliers

6-(Trifluoromethyl)nicotinonitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T+,Xi
• Hazard Codes: T+,Xi
• Statements: 28-37/38-41-43
• Safety Statements: 26-28-36/37/39-45

MSDS Files:

Useful:

• Canonical SMILES: C1=CC(=NC=C1C#N)C(F)(F)F
• Uses: 6-(Trifluoromethyl)nicotinonitrile can be used as CS-1R inhibitors.

Technology Process of 6-(Trifluoromethyl)nicotinonitrile

There total 2 articles about 6-(Trifluoromethyl)nicotinonitrile 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: 45.0%

3-cyanopyridin-1-ium-1-yl tris(2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenyl)borate + (trifluoromethyl)trimethylsilane (81290-20-2) → 4-(trifluoromethyl)nicotinonitrile (13600-43-6) + 6-(trifluoromethyl)nicotinonitrile (216431-85-5)

Guidance literature:

3-cyanopyridin-1-ium-1-yl tris(2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenyl)borate; (trifluoromethyl)trimethylsilane; With tetrabutylammonium triphenyldifluorosilicate; In ethyl acetate; at -40 ℃; for 11h; Molecular sieve; Inert atmosphere;

With bis-[(trifluoroacetoxy)iodo]benzene; In ethyl acetate; at 25 ℃; for 10h; regioselective reaction; Inert atmosphere;

DOI:10.1021/jacs.6b01753

Reference yield:

pyridine-3-carbonitrile (100-54-9,121697-66-3,1232169-17-3,68271-95-4) → 4-(trifluoromethyl)nicotinonitrile (13600-43-6) + 6-(trifluoromethyl)nicotinonitrile (216431-85-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: n-butyllithium / diethyl ether; hexane / 1 h / -78 °C / Inert atmosphere

1.2: -50 - 25 °C / Inert atmosphere

1.3: 12 h / 25 °C / Inert atmosphere

2.1: tetrabutylammonium triphenyldifluorosilicate / ethyl acetate / 11 h / -40 °C / Molecular sieve; Inert atmosphere

2.2: 10 h / 25 °C / Inert atmosphere

With n-butyllithium; tetrabutylammonium triphenyldifluorosilicate; In diethyl ether; hexane; ethyl acetate;

DOI:10.1021/jacs.6b01753

Reference yield: 98.0%

6-(trifluoromethyl)nicotinonitrile (216431-85-5) → 6-(trifluoromethyl)pyridine-3-carboxamide (386715-35-1)

Guidance literature:

With manganese(IV) oxide; water; In isopropyl alcohol; at 70 ℃; for 0.25h; under 5171.62 Torr;

DOI:10.1021/ol403591c

upstream raw materials:

(trifluoromethyl)trimethylsilane

pyridine-3-carbonitrile

Downstream raw materials:

6-trifluoromethylnicotinic acid

1-[(6-trifluoromethyl)-pyridine-3-yl]ethan-1-one

6-(trifluoromethyl)pyridine-3-carboxamide

2-phenyl-6-(trifluoromethyl)nicotinonitrile

Refernces