Adamantane-2-carbonitrile

Base Information

• Chemical Name: Adamantane-2-carbonitrile
• CAS No.: 35856-00-9
• Molecular Formula: C11 H15 N
• Molecular Weight: 161.247
• European Community (EC) Number: 958-888-9
• Nikkaji Number: J89.057J
• Mol file: 35856-00-9.mol

Synonyms:adamantane-2-carbonitrile;2-adamantanecarbonitrile;35856-00-9;MFCD03105191;2-cyanoadamantane;(1r,3r,5r,7r)-adamantane-2-carbonitrile;SCHEMBL1726623;SCHEMBL12420559;SCHEMBL12508912;SCHEMBL21147695;SCHEMBL24066458;KHCMWKSXPURXRL-UHFFFAOYSA-N;AKOS004122867;AKOS006277227;AS-79709;SY323027;CS-0100829;P19856;EN300-1581764;Z1436192933

Chemical Property of Adamantane-2-carbonitrile

Chemical Property:

• Melting Point: 177 °C(Solv: hexane (110-54-3))
• Boiling Point: 283.5±9.0 °C(Predicted)
• PSA: 23.79000
• Density: 1.06±0.1 g/cm3(Predicted)
• LogP: 2.58228
• XLogP3: 3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 161.120449483
• Heavy Atom Count: 12
• Complexity: 219

Purity/Quality:

99% ^*data from raw suppliers

Adamantane-2-carbonitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C2CC3CC1CC(C2)C3C#N

Technology Process of Adamantane-2-carbonitrile

There total 13 articles about Adamantane-2-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: 99.0%

2-Adamantanone (700-58-3) + [(p-methylphenyl)sulfonylmethyl]isonitrile (38622-91-2,36635-61-7) → 2-adamantanecarbonitrile (35856-00-9)

Guidance literature:

With potassium tert-butylate; In 1,2-dimethoxyethane; ethanol; at 5 - 40 ℃; for 1.5h;

DOI:10.1002/adsc.201600156

Reference yield: 96.0%

C13H17N3O2 (666748-75-0) → 2-adamantanecarbonitrile (35856-00-9)

Guidance literature:

With methanol; sodium methylate;

DOI:10.2174/157017811797249452

Reference yield: 88.0%

trimethylsilyl cyanide (7677-24-9) + 2-adamantanecarbonyl chloride (40079-92-3) → 2-adamantanecarbonitrile (35856-00-9)

Guidance literature:

With bis(1,5-cyclooctadiene)nickel ⁽⁰⁾; triphenylphosphine; In toluene; at 110 ℃; for 1h; Schlenk technique; Inert atmosphere;

DOI:10.1021/acs.orglett.9b02398

upstream raw materials:

2-Adamantanone

[(p-methylphenyl)sulfonylmethyl]isonitrile

Phosphoric acid 2-cyano-adamantan-2-yl ester diethyl ester

N-methylene-1-(p-tolylsulfonyl)methylamine

Downstream raw materials:

adamantan-2-yl(phenyl)methanone

2-Adamantylphenylketimin

1-((3r,5r,7r)-adamantan-1-yl)ethan-1-one

(2-adamantyl)dimethylcarbinol

Refernces

• 1、 Zoidis, Grigoris,Kolocouris, Nicolas. "Facile and effective synthesis of spirocycloalkanones". . p. 531 - 535. Retrieved 2011.
• 2、 -. "Preparation method of alkyl nitrile compound". Paragraph 0249-0251; 0255-0257. . Retrieved 2020/05/14.
• 3、 Wang, Zhenhua,Wang, Xiu,Ura, Yasuyuki,Nishihara, Yasushi. "Nickel-Catalyzed Decarbonylative Cyanation of Acyl Chlorides". supporting information. p. 6779 - 6784. Retrieved 2019/08/26.