4-Morpholinobenzonitrile

Base Information

• Chemical Name: 4-Morpholinobenzonitrile
• CAS No.: 10282-31-2
• Molecular Formula: C11H12N2O
• Molecular Weight: 188.229
• Hs Code.: 2934999090
• European Community (EC) Number: 680-190-5
• NSC Number: 698610
• DSSTox Substance ID: DTXSID10327876
• Nikkaji Number: J829.910B
• Wikidata: Q82089996
• ChEMBL ID: CHEMBL1988902
• Mol file: 10282-31-2.mol

Synonyms:4-Morpholinobenzonitrile;10282-31-2;4-(4-Cyanophenyl)morpholine;4-morpholin-4-ylbenzonitrile;4-(morpholin-4-yl)benzonitrile;Benzonitrile, 4-(4-morpholinyl)-;MFCD00100115;4-(4-Morpholinyl)benzonitrile;NSC698610;4-(4-Cyanobenzene)morpholine;4-Morpholin-4-yl-benzonitrile;Benzonitrile,4-(4-morpholinyl)-;Maybridge3_004519;N-(4-cyanophenyl)morpholine;SCHEMBL39646;4(4-morpholinyl) benzonitrile;4-(4-morpholinyl) Benzonitrile;CHEMBL1988902;DTXSID10327876;CHEBI:194885;HMS1443N09;STL411563;AKOS000218410;FS-2630;NSC-698610;IDI1_015906;AC-17779;NCI60_035307;SY007192;C2008;CS-0067771;FT-0758903;EN300-37335;Z168802120

Chemical Property of 4-Morpholinobenzonitrile

Chemical Property:

• Vapor Pressure: 1.01E-05mmHg at 25°C
• Melting Point: 85 °C
• Refractive Index: 1.583
• Boiling Point: 371.7 °C at 760mmHg
• PKA: 1.69±0.40(Predicted)
• Flash Point: 178.6 °C
• PSA: 36.26000
• Density: 1.17 g/cm³
• LogP: 1.45988
• Storage Temp.: Sealed in dry,Room Temperature
• Water Solubility.: Soluble in water.
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 188.094963011
• Heavy Atom Count: 14
• Complexity: 219

Purity/Quality:

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

4-Morpholinobenzonitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1COCCN1C2=CC=C(C=C2)C#N

Technology Process of 4-Morpholinobenzonitrile

There total 42 articles about 4-Morpholinobenzonitrile 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%

morpholine (110-91-8,99108-56-2) + 4-Cyanochlorobenzene (623-03-0) → 4-morpholinobenzonitrile (10282-31-2)

Guidance literature:

With 2-(dicyclohexylphosphino)-4'-(N,N-dimethylamino)-1,1'-biphenyl; at 20 ℃;

DOI:10.1021/ja902679b

Reference yield: 100.0%

morpholine (110-91-8,99108-56-2) + 4-bromobenzenecarbonitrile (623-00-7) → 4-morpholinobenzonitrile (10282-31-2)

Guidance literature:

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; palladium 10% on activated carbon; caesium carbonate; In cyclopentyl methyl ether; for 24h; Inert atmosphere; Reflux;

DOI:10.1002/adsc.200800417

Reference yield: 98.0%

4-bromophenyl-morpholine (30483-75-1) + potassium ferrocyanide → 4-morpholinobenzonitrile (10282-31-2)

Guidance literature:

With dichloro[bis{1-(dicyclohexylphosphanyl)piperidine}]palladium; sodium carbonate; In 1-methyl-pyrrolidin-2-one; at 140 ℃; for 8h; Inert atmosphere;

DOI:10.1002/chem.201102936

upstream raw materials:

morpholine

4-fluorobenzonitrile

4-cyanophenyl trifluoromethanesulfonate

4-Cyanochlorobenzene

Downstream raw materials:

(4-(5-ethyl-[1,6]naphthyridin-7-yl)phenyl)morpholine

C₂₃H₂₅N₃OSi

(4-(5-ethynyl-[1,6]naphthyridin-7-yl)phenyl)morpholine

trifluoromethanesulphonic acid 7-(4-morpholin-4-yl-phenyl)-[1,6]naphthyridin-5-yl ester

Refernces

• 1、 Viciu, Mihai S.,Kelly III, Roy A.,Stevens, Edwin D.,Naud, Frederic,Studer, Martin,Nolan, Steven P.. "Synthesis, characterization, and catalytic activity of N-heterocyclic carbene (NHC) palladacycle complexes". . p. 1479 - 1482. Retrieved 2003.
• 2、 Zhang, Xiao-Xiang,Harris, Michele C.,Sadighi, Joseph P.,Buchwald, Stephen L.. "The use of palladium chloride as a precatalyst for the amination of aryl bromides". . p. 1799 - 1805. Retrieved 2001.
• 3、 Motiwala, Hashim F.,Yin, Qin,Aubé, Jeffrey. "Improved schmidt conversion of aldehydes to nitriles using azidotrimethylsilane in 1,1,1,3,3,3-Hexafluoro-2-Propanol". . . Retrieved 2016.
• 4、 Al-Amin, Mohammad,Honma, Tetsuo,Hoshiya, Naoyuki,Shuto, Satoshi,Arisawa, Mitsuhiro. "Ligand-free Buchwald-Hartwig aromatic aminations of aryl halides catalyzed by low-leaching and highly recyclable sulfur-modified gold-supported palladium material". . p. 1061 - 1068. Retrieved 2012.
• 5、 Thapa, Kiran,Paul, Piyali,Bhattacharya, Samaresh. "A group of diphosphine-thiosemicarbazone complexes of palladium: Efficient precursors for catalytic C–C and C–N coupling reactions". . p. 232 - 239. Retrieved 2019.
• 6、 Louie, Janis,Driver, Michael S.,Hamann, Blake C.,Hartwig, John F.. "Palladium-Catalyzed Amination of Aryl Triflates and Importance of Triflate Addition Rate". . p. 1268 - 1273. Retrieved 1997.
• 7、 Kim, Miji,Shin, Taeil,Lee, Ansoo,Kim, Hyunwoo. "Synergistic Ligand Effect between N-Heterocyclic Carbene (NHC) and Bicyclic Phosphoramidite (Briphos) Ligands in Pd-Catalyzed Amination". . p. 3253 - 3258. Retrieved 2018.
• 8、 Tasler, Stefan,Lipshutz, Bruce H.. "Nickel-on-charcoal-catalyzed aromatic aminations and Kumada couplings: Mechanistic and synthetic aspects". . p. 1190 - 1199. Retrieved 2003.
• 9、 Sawatzky, Ryan S.,Ferguson, Michael J.,Stradiotto, Mark. "Thieme Chemistry Journals Awardees - Where Are They Now? Efficient Cross-Coupling of Secondary Amines/Azoles and Activated (Hetero)Aryl Chlorides Using an Air-Stable DPEPhos/Nickel Pre-Catalyst". . p. 1586 - 1591. Retrieved 2017.
• 10、 Ahany Kamangar, Sheida,Hashemi Salehi, Mirmehdi,Hekmati, Malak,Hemmati, Saba,Yousefi, Mohammad. "Cu(I)-anchored polyvinyl alcohol coated-magnetic nanoparticles as heterogeneous nanocatalyst in Ullmann-type C–N coupling reactions". . . Retrieved 2020.