1-Cyano-4-fluoronaphthalene

Base Information

• Chemical Name: 1-Cyano-4-fluoronaphthalene
• CAS No.: 13916-99-9
• Molecular Formula: C11H6FN
• Molecular Weight: 171.174
• Hs Code.: 2926909090
• European Community (EC) Number: 670-852-1
• DSSTox Substance ID: DTXSID60371561
• Wikidata: Q82158925
• Mol file: 13916-99-9.mol

Synonyms:1-Cyano-4-fluoronaphthalene;13916-99-9;4-Fluoro-1-naphthonitrile;4-fluoronaphthalene-1-carbonitrile;1-Naphthalenecarbonitrile, 4-fluoro-;4-fluoro-1-naphthalenecarbonitrile;1-Naphthalenecarbonitrile,4-fluoro-;1-cyano-4-fluoronapthalene;4-cyano-1-fluoronaphthalene;SCHEMBL1363490;DTXSID60371561;XQSGYYNFKIQWAC-UHFFFAOYSA-N;4-Fluoro-naphthalene-1-carbonitrile;4-fluoranylnaphthalene-1-carbonitrile;MFCD00236656;AKOS006227997;PS-6453;CS-0090607;FT-0676146;E74221;EN300-196452;A807492;Z1201619982

Chemical Property of 1-Cyano-4-fluoronaphthalene

Chemical Property:

• Vapor Pressure: 0.000452mmHg at 25°C
• Melting Point: 89-91°C
• Refractive Index: 1.621
• Boiling Point: 314.9 °C at 760 mmHg
• Flash Point: 156.3 °C
• PSA: 23.79000
• Density: 1.22g/cm³
• LogP: 2.85058
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 171.048427358
• Heavy Atom Count: 13
• Complexity: 230

Purity/Quality:

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

1-Cyano-4-fluoronaphthalene ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 20/21/22
• Safety Statements: 26-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C(=CC=C2F)C#N

Technology Process of 1-Cyano-4-fluoronaphthalene

There total 5 articles about 1-Cyano-4-fluoronaphthalene 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: 88.4%

1-bromo-4-fluoronaphthalene (341-41-3) + potassium ferrocyanide → 4-fluoronaphthalene-1-carbonitrile (13916-99-9)

Guidance literature:

With palladium diacetate; sodium carbonate; In N,N-dimethyl acetamide; at 120 ℃; for 12h; Inert atmosphere;

DOI:10.1016/j.ejmech.2017.02.029

Reference yield: 88.0%

1-bromo-4-fluoronaphthalene (341-41-3) + copper(l) cyanide → 4-fluoronaphthalene-1-carbonitrile (13916-99-9)

Guidance literature:

In N,N-dimethyl-formamide; at 130 ℃; for 12h; Inert atmosphere;

DOI:10.2174/1573406412666160915163002

Reference yield: 45.0%

4-cyanopyridine N-oxide (14906-59-3) + 1-bromo-4-fluoronaphthalene (341-41-3) → 4-fluoronaphthalene-1-carbonitrile (13916-99-9)

Guidance literature:

With potassium fluoride; 4,4'-dimethyl-2,2'-bipyridines; trifluoroacetic acid; sodium iodide; nickel dichloride; zinc; In N,N-dimethyl acetamide; at 60 ℃; for 36h;

DOI:10.1021/acscatal.9b04586

upstream raw materials:

1-bromo-4-fluoronaphthalene

copper(I) cyanide

4-cyanopyridine N-oxide

Downstream raw materials:

4-(8-azabicyclo[3.2.1]oct-8-yl)naphthalene-1-carbonitrile

4-(3-hydroxy-8-azabicyclo[3.2.1]oct-8-yl)naphthalene-1-carbonitrile

4-methoxy-1-naphthalenecarbonitrile

Refernces

• 1、 Chen, Hui,Sun, Shuhao,Liu, Yahu A.,Liao, Xuebin. "Nickel-Catalyzed Cyanation of Aryl Halides and Hydrocyanation of Alkynes via C-CN Bond Cleavage and Cyano Transfer". . p. 1397 - 1405. Retrieved 2020/02/04.
• 2、 Zhang, Xiansheng,Wu, Jingwei,Liu, Wei,Liu, Yuqiang,Xie, Yafei,Shang, Qian,Zhou, Zhixing,Xu, Weiren,Tang, Lida,Wang, Jianwu,Zhao, Guilong. "Discovery of flexible naphthyltriazolylmethane-based thioacetic acids as highly active uric acid transporter 1 (URAT1) inhibitors for the treatment of hyperuricemia of gout". . p. 260 - 281. Retrieved 2017/05/31.