2-Amino-5-phenyl-3-furonitrile

Base Information

• Chemical Name: 2-Amino-5-phenyl-3-furonitrile
• CAS No.: 14742-32-6
• Molecular Formula: C11H8 N2 O
• Molecular Weight: 184.197
• Hs Code.: 2932190090
• European Community (EC) Number: 672-974-0
• DSSTox Substance ID: DTXSID70351238
• Nikkaji Number: J1.130.289K
• Wikidata: Q82127481
• ChEMBL ID: CHEMBL4071281
• Mol file: 14742-32-6.mol

Synonyms:2-amino-5-phenyl-3-furonitrile;14742-32-6;2-amino-5-phenylfuran-3-carbonitrile;MFCD00463472;3-Furancarbonitrile, 2-amino-5-phenyl-;2-Amino-3-cyano-5-phenylfuran;Maybridge1_000452;Oprea1_564550;Oprea1_639656;SCHEMBL1789380;CHEMBL4071281;HMS542M12;DTXSID70351238;UWTDTJWGYWUILP-UHFFFAOYSA-N;BBL028660;CCG-43413;STK978221;AKOS001106064;2-Amino-5-phenyl-furan-3-carbonitrile;FS-1440;SB61157;SDCCGMLS-0065836.P001;2-amino-5-phenyl-3-furonitrile, AldrichCPR;FT-0611189;EN300-14307;F16088;A808646;SR-01000633336-1;W-205659;Z99599908;F0777-1641

Chemical Property of 2-Amino-5-phenyl-3-furonitrile

Chemical Property:

• Vapor Pressure: 6.12E-06mmHg at 25°C
• Melting Point: 196 °C
• Boiling Point: 378.8°Cat760mmHg
• PKA: -1.66±0.10(Predicted)
• Flash Point: 182.9°C
• PSA: 62.95000
• Density: 1.26g/cm³
• LogP: 2.98168
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 184.063662883
• Heavy Atom Count: 14
• Complexity: 239

Purity/Quality:

98%min ^*data from raw suppliers

2-Amino-5-phenyl-3-furonitrile ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi,Xn
• Statements: 22-36
• Safety Statements: 26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C2=CC(=C(O2)N)C#N

Technology Process of 2-Amino-5-phenyl-3-furonitrile

There total 16 articles about 2-Amino-5-phenyl-3-furonitrile 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: 90.0%

5-Amino-2-phenyl-2,3-dihydro-furan-2,4-dicarbonitrile (100805-20-7) → 2-amino-5-phenylfuran-3-carbonitrile (14742-32-6)

Guidance literature:

With potassium hydroxide; water; In methanol; for 0.25h;

Reference yield: 89.0%

nitrostyrene (5153-67-3) + 2-(2-oxo-2-phenylethyl)malononitrile (14476-72-3) → 1-cyano-4-nitro-3,5-diphenylcyclopent-2-enecarboxamide + 2-amino-5-phenylfuran-3-carbonitrile (14742-32-6)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; dimethyl sulfoxide; at 25 ℃; for 5h; diastereoselective reaction;

DOI:10.1021/acs.orglett.8b00510

Reference yield: 87.0%

nitrostyrene (5153-67-3) + 2-(2-oxo-2-phenylethyl)malononitrile (14476-72-3) → 1-cyano-4-nitro-3,5-diphenylcyclopent-2-enecarboxamide + 1-cyano-4-nitro-3,5-diphenylcyclopent-2-enecarboxamide + 2-amino-5-phenylfuran-3-carbonitrile (14742-32-6)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; N,N-dimethyl-formamide; at 25 ℃; for 5h; Reagent/catalyst; Solvent; diastereoselective reaction;

DOI:10.1021/acs.orglett.8b00510

upstream raw materials:

2-(2-oxo-2-phenylethyl)malononitrile

α-bromoacetophenone

malononitrile

5-Amino-2-phenyl-2,3-dihydro-furan-2,4-dicarbonitrile

Downstream raw materials:

2-Amino-2-phenyl-5-cyano-7-phenylisoindoline-1,3-dione

4-Amino-2-(4-chloro-phenyl)-1,3-dioxo-7-phenyl-2,3-dihydro-1H-isoindole-5-carbonitrile

Refernces

• 1、 Khaledian, Omid,Yavari, Issa. "Copper-Catalyzed Tandem Dehydrocyanation and [3+2] Cyclo-addition Reactions of Phenacylmalononitriles: Regioselective Synthesis of Functionalized 4-Benzoyl-5-cyanopyrazoles under Mild Conditions". . p. 1379 - 1386. Retrieved 2020/04/27.
• 2、 Han, Jin,Kaspersen, Svein Jacob,Nervik, Sondre,N?rsett, Kristin G.,Sundby, Eirik,Hoff, B?rd Helge. "Chiral 6-aryl-furo[2,3-d]pyrimidin-4-amines as EGFR inhibitors". . p. 278 - 299. Retrieved 2016/06/14.