4-Quinolineacetonitrile

Base Information

• Chemical Name: 4-Quinolineacetonitrile
• CAS No.: 14003-46-4
• Molecular Formula: C11H8 N2
• Molecular Weight: 168.198
• Hs Code.: 2933499090
• NSC Number: 85366
• DSSTox Substance ID: DTXSID60292762
• Nikkaji Number: J1.426.157E
• Wikidata: Q82031198
• ChEMBL ID: CHEMBL1888570
• Mol file: 14003-46-4.mol

Synonyms:2-(QUINOLIN-4-YL)ACETONITRILE;14003-46-4;4-Quinolineacetonitrile;2-quinolin-4-ylacetonitrile;MLS002694628;NSC85366;4-Chinolyl-acetonitril;Quinoline-4-acetonitrile;quinolin-4-ylacetonitrile;NCIOpen2_001088;SCHEMBL349073;CHEMBL1888570;DTXSID60292762;CKTDILDXLGTRNG-UHFFFAOYSA-N;HMS3094O19;NSC-85366;AKOS008969278;SB67801;BS-51696;SMR001560553;CS-0270251;FT-0648380;EN300-1602311

Chemical Property of 4-Quinolineacetonitrile

Chemical Property:

• Vapor Pressure: 3.03E-05mmHg at 25°C
• Boiling Point: 355.9°Cat760mmHg
• Flash Point: 123.3°C
• PSA: 36.68000
• Density: 1.176g/cm³
• LogP: 2.30088
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 168.068748264
• Heavy Atom Count: 13
• Complexity: 215

Purity/Quality:

98%min ^*data from raw suppliers

4-Quinolineacetonitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C(=CC=N2)CC#N
• Uses: 4-Quinolineacetonitrile is an reagent used in the synthetic preparation of potential bone morphogenetic protein (BMP) signaling inhibitor.

Technology Process of 4-Quinolineacetonitrile

There total 11 articles about 4-Quinolineacetonitrile 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: 77.0%

quinoline-4-carboxaldehyde (4363-93-3) + diethyl cyanophosphonate (2942-58-7) → 2-(quinolin-4-yl)acetonitrile (14003-46-4)

Guidance literature:

quinoline-4-carboxaldehyde; diethyl cyanophosphonate; With lithium cyanide; In tetrahydrofuran; at 20 ℃;

With samarium diiodide; tert-butyl alcohol; In tetrahydrofuran; at 20 ℃;

DOI:10.1016/S0040-4039(03)00427-1

Reference yield:

potassium cyanide + 4-(chloromethyl)quinoline (5632-17-7) → 2-(quinolin-4-yl)acetonitrile (14003-46-4)

Guidance literature:

In N,N-dimethyl-formamide; at 20 - 80 ℃;

Reference yield:

4-(chloromethyl)quinoline (5632-17-7) → 2-(quinolin-4-yl)acetonitrile (14003-46-4)

Guidance literature:

With sodium cyanide; In N,N-dimethyl-formamide; at 20 ℃;

DOI:10.1016/j.bmcl.2008.06.052

upstream raw materials:

C₆H₄NCH₂CHCCH₂

methyl(phenyl)cyanamide

3-[4]quinolyl-2-hydroxyimino-propionic acid

benzoyloxy-[4]quinolyl-acetonitrile

Downstream raw materials:

2-[4]quinolyl-3c-(4-dimethylamino-phenyl)-acrylonitrile

[4]quinolyl-(4-dimethylamino-phenylimino)-acetonitrile

ethyl 4-quinolineacetate

4-quinolin-4-yl-2H-pyrazol-3-ylamine

Refernces

• 1、 Cuny, Gregory D.,Yu, Paul B.,Laha, Joydev K.,Xing, Xuechao,Liu, Ji-Feng,Lai, Carol S.,Deng, Donna Y.,Sachidanandan, Chetana,Bloch, Kenneth D.,Peterson, Randall T.. "Structure-activity relationship study of bone morphogenetic protein (BMP) signaling inhibitors". supporting information; body text. p. 4388 - 4392. Retrieved 2009/04/06.
• 2、 Klemm, L.H.,Lu, Jennifer J.,Greene, Diana S.,Boisvert, William. "Chemistry of Thienopyridines. XXXV. Synthesis, Tautomerism, and Reactions of Quinoline and Thienopyridine Systems Which Bear a 1-Carboethoxy-1-cyanomethyl Substituent in the Pyridine Ring, Part 2". . p. 1467 - 1472. Retrieved 2007/10/02.