10-Methylphenanthrene-9-carbonitrile

Base Information

• Chemical Name: 10-Methylphenanthrene-9-carbonitrile
• CAS No.: 17024-15-6
• Molecular Formula: C₁₆H₁₁N
• Molecular Weight: 217.27
• Hs Code.: 2926909090
• NSC Number: 154728
• DSSTox Substance ID: DTXSID70302866
• Nikkaji Number: J151.374E
• Wikidata: Q82047914
• Mol file: 17024-15-6.mol

Synonyms:10-methylphenanthrene-9-carbonitrile;17024-15-6;NSC 154728;NSC154728;9-Cyano-10-methylphenanthrene;DTXSID70302866;NSC-154728

Chemical Property of 10-Methylphenanthrene-9-carbonitrile

Chemical Property:

• Vapor Pressure: 1.7E-07mmHg at 25°C
• Boiling Point: 427°Cat760mmHg
• Flash Point: 213.5°C
• PSA: 23.79000
• Density: 1.18g/cm³
• LogP: 4.17308
• XLogP3: 4.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 217.089149355
• Heavy Atom Count: 17
• Complexity: 326

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(C2=CC=CC=C2C3=CC=CC=C13)C#N

Technology Process of 10-Methylphenanthrene-9-carbonitrile

There total 6 articles about 10-Methylphenanthrene-9-carbonitrile 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: 87.0%

(E)-3-(2-iodophenyl)but-2-enenitrile + 2-(trimethylsilyl)phenyl trifluoromethanesulfonate (88284-48-4) → 10-methylphenanthrene-9-carbonitrile (17024-15-6)

Guidance literature:

With cesium fluoride; bis-diphenylphosphinomethane; bis(dibenzylideneacetone)-palladium⁽⁰⁾; In toluene; acetonitrile; at 110 ℃; for 14h; Inert atmosphere;

DOI:10.1021/acs.orglett.6b00558

Reference yield: 57.0%

2-(2-bromophenyl)-2-oxoacetic acid (26767-16-8) + (E)-3-(2-iodophenyl)but-2-enenitrile → 10-methylphenanthrene-9-carbonitrile (17024-15-6)

Guidance literature:

With trifuran-2-yl-phosphane; palladium diacetate; lithium tert-butoxide; Trimethylacetic acid; In N,N-dimethyl acetamide; at 20 - 120 ℃; for 12.25h; regioselective reaction; Sealed tube;

DOI:10.1021/acs.orglett.1c03517

Reference yield: 56.0%

2-(2-bromophenyl)acetonitrile (19472-74-3) + (2-acetylphenyl)boronic acid (308103-40-4) → 10-methylphenanthrene-9-carbonitrile (17024-15-6)

Guidance literature:

With caesium carbonate; DavePhos; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In ethanol; toluene; at 120 - 150 ℃; for 0.166667h; microwave irradiation;

DOI:10.1021/jo702001n

upstream raw materials:

9-bromo-10-methyl-phenanthrene

copper(I) cyanide

2-(2-bromophenyl)acetonitrile

(2-acetylphenyl)boronic acid

Downstream raw materials:

10-methyl-phenanthrene-9-carboxylic acid amide

Refernces

• 1、 Jiang, Guomin,Ye, Hao,Shi, Lei,Dai, Hong,Wu, Xin-Xing. "Palladium-Catalyzed Sequential Vinyl C–H Activation/Dual Decarboxylation: Regioselective Synthesis of Phenanthrenes and Cyclohepta[1,2,3-de]naphthalenes". supporting information. p. 9398 - 9402. Retrieved 2021/12/09.
• 2、 Young, Ha Kim,Lee, Hyuk,Yeong, Joon Kim,Bum, Tae Kim,Heo, Jung-Nyoung. "Direct one-pot synthesis of phenanthrenes via Suzuki-Miyaura coupling/aldol condensation cascade reaction". . p. 495 - 501. Retrieved 2008/09/17.