2,6-Dihydroxy-4-(trifluoromethyl)nicotinonitrile

Base Information

• Chemical Name: 2,6-Dihydroxy-4-(trifluoromethyl)nicotinonitrile
• CAS No.: 3335-46-4
• Molecular Formula: C7H3F3N2O2
• Molecular Weight: 204.108
• Hs Code.: 2933399090
• DSSTox Substance ID: DTXSID70382188
• Wikidata: Q72467069
• Mol file: 3335-46-4.mol

Synonyms:3335-46-4;2,6-dihydroxy-4-(trifluoromethyl)nicotinonitrile;3-Cyano-2,6-dihydroxy-4-(trifluoromethyl)pyridine;2,6-dihydroxy-4-(trifluoromethyl)pyridine-3-carbonitrile;2-hydroxy-6-oxo-4-(trifluoromethyl)-1H-pyridine-3-carbonitrile;MFCD06200911;2,6-Dihydroxy-3-cyano-4-(trifluoromethyl)pyridine;3-Pyridinecarbonitrile, 1,2-dihydro-6-hydroxy-2-oxo-4-(trifluoromethyl)-;C7H3F3N2O2;SCHEMBL9017997;DTXSID70382188;JRLZWXISQMMITA-UHFFFAOYSA-N;BCP26991;BBL100566;CL0198;STL554360;AKOS005063910;AKOS028109458;AC-9583;CS-W003264;SY007022;AM20051079;FT-0658012;2,6-dihydroxy-3-cyano-4-trifluoromethylpyridine;10X-0866;J-507486;3-cyano-2,6-dihydroxy-4-(trifluoromethyl)pyridine, AldrichCPR;2-Hydroxy-6-oxo-4-(trifluoromethyl)-1,6-dihydro-3-pyridinecarbonitrile;6-hydroxy-2-oxo-4-(trifluoromethyl)-1,2-dihydropyridine-3-carbonitrile

Chemical Property of 2,6-Dihydroxy-4-(trifluoromethyl)nicotinonitrile

Chemical Property:

• Appearance/Colour: white solid
• Vapor Pressure: 0.00258mmHg at 25°C
• Melting Point: 285°C
• Refractive Index: 1.508
• Boiling Point: 582.153 °C at 760 mmHg
• PKA: 2.57±0.58(Predicted)
• Flash Point: 305.875 °C
• PSA: 77.14000
• Density: 1.63 g/cm³
• LogP: 1.38328
• Storage Temp.: Inert atmosphere,Room Temperature
• XLogP3: 0.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 0
• Exact Mass: 204.01466183
• Heavy Atom Count: 14
• Complexity: 397

Purity/Quality:

99% ^*data from raw suppliers

3-Cyano-2,6-dihydroxy-4-(trifluoromethyl)pyridine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi,T
• Statements: 25-36
• Safety Statements: 26-45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=C(C(=C(NC1=O)O)C#N)C(F)(F)F
• Uses: 3-Cyano-2,6-dihydroxy-4-(trifluoromethyl)pyridine is used as a reagent in the synthesis of novel monoindolyl-4-trifluoromethylpyridines and bisindolyl-4-trifluoromethylpyridines which can be used as potential antitumor agents.

Technology Process of 2,6-Dihydroxy-4-(trifluoromethyl)nicotinonitrile

There total 1 articles about 2,6-Dihydroxy-4-(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: 63.0%

methyl 4,4,4-trifluoroacetoacetate (83643-84-9,488711-09-7) + cyanoacetic acid amide (107-91-5) → 2,6-dihydroxy-3-cyano-4-(trifluoromethyl)pyridine (3335-46-4)

Guidance literature:

With sodium methylate; In methanol; at 60 ℃; for 8h;

DOI:10.1016/S0960-894X(00)00704-6

Reference yield:

2,6-dihydroxy-3-cyano-4-(trifluoromethyl)pyridine (3335-46-4) → 4-(trifluoromethyl)nicotinic acid (158063-66-2)

Guidance literature:

Multi-step reaction with 4 steps

1: trichlorophosphate / dichloromethane; N,N-dimethyl-formamide / 6 h / 125 °C

2: sodium bromide; sulfuric acid

3: sodium carbonate; 5%-palladium/activated carbon; hydrogen / methanol / 6 h

4: sodium hydroxide / 5 h / 100 °C

With sulfuric acid; 5%-palladium/activated carbon; hydrogen; sodium carbonate; sodium bromide; sodium hydroxide; trichlorophosphate; In methanol; dichloromethane; N,N-dimethyl-formamide;

Reference yield:

2,6-dihydroxy-3-cyano-4-(trifluoromethyl)pyridine (3335-46-4) → 3-cyano-4-trifluoromethyl-2,6-bis[3'-(N-toluenesulfonylindolyl)]pyridine

Guidance literature:

Multi-step reaction with 2 steps

1: 80 percent / POCl₃ / 18 h / 140 °C

2: 60 percent / Pd(PPh₃)4; aq. Na₂CO₃ / methanol; benzene

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate; trichlorophosphate; In methanol; benzene; 2: Suzuki cross coupling;

DOI:10.1016/S0960-894X(00)00704-6

upstream raw materials:

methyl 4,4,4-trifluoroacetoacetate

cyanoacetic acid amide

Downstream raw materials:

2,6-dichloro-4-trifluoromethyl-3-pyridine carboxamide

4-(trifluoromethyl)nicotinic acid

Refernces