1,3-Bis(1-adamantyl)imidazol-2-ylidene

Base Information

• Chemical Name: 1,3-Bis(1-adamantyl)imidazol-2-ylidene
• CAS No.: 131042-77-8
• Molecular Formula: C23H32 N2
• Molecular Weight: 336.52
• DSSTox Substance ID: DTXSID90436293
• Nikkaji Number: J1.137.607J
• Wikidata: Q72462603
• Mol file: 131042-77-8.mol

Synonyms:1,3-bis(1-adamantyl)-2H-imidazole;1,3-bis(1-adamantyl)imidazol-2-ylidene;131042-77-8;1,3-Di(1-adamantyl)-4-imidazoline;Arduengo's carbene;1,3-diadamantylimidazole;SCHEMBL469272;SCHEMBL16800814;DTXSID90436293;CS-0203310;1,3-BIS(ADAMANTAN-1-YL)-2,3-DIHYDRO-1H-IMIDAZOLE

Chemical Property of 1,3-Bis(1-adamantyl)imidazol-2-ylidene

Chemical Property:

• Melting Point: 240-241°C
• Refractive Index: 1.641
• PSA: 6.48000
• LogP: 4.59850
• Sensitive.: air sensitive, moisture sensitiv
• XLogP3: 6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 338.272199093
• Heavy Atom Count: 25
• Complexity: 485

Purity/Quality:

98%Min ^*data from raw suppliers

1,3-Bis(1-adamantyl)imidazol-2-ylidene, min. 98% ARDUENGO'S CARBENE ^*data from reagent suppliers

Safty Information:

• Pictogram(s): R10:
• Hazard Codes: R10:
• Statements: 10
• Safety Statements: 9-16

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C2CC3CC1CC(C2)(C3)N4CN(C=C4)C56CC7CC(C5)CC(C7)C6

Technology Process of 1,3-Bis(1-adamantyl)imidazol-2-ylidene

There total 3 articles about 1,3-Bis(1-adamantyl)imidazol-2-ylidene 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: 74.0%

1,3-di(adamantan-1-yl)-1H-imidazol-3-ium tetrafluoroborate (286014-42-4) → IAd (131042-77-8)

Guidance literature:

With potassium tert-butylate; In tetrahydrofuran; at 20 ℃; for 5h; Inert atmosphere;

DOI:10.1246/cl.2012.298

Reference yield:

1,3-di(adamantan-1-yl)-1H-imidazol-3-ium chloride (131042-78-9) → IAd (131042-77-8)

Guidance literature:

With sodium hydride; dimethyl sulfoxide; In tetrahydrofuran; Ambient temperature;

DOI:10.1021/ja00001a054

Reference yield:

1-Adamantanamine (768-94-5) → IAd (131042-77-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: chloroform / 1 h / 20 °C

1.2: 0 - 60 °C

2.1: potassium tert-butylate / tetrahydrofuran / 5 h / 20 °C / Inert atmosphere

With potassium tert-butylate; In tetrahydrofuran; chloroform;

DOI:10.1246/cl.2012.298

upstream raw materials:

1,3-di(adamantan-1-yl)-1H-imidazol-3-ium chloride

1,3-di(adamantan-1-yl)-1H-imidazol-3-ium tetrafluoroborate

1-Adamantanamine

Downstream raw materials:

[((1,3-di-1-adamanthylimidazolin-2-ylidene)(+1H))][(hydride)B(pentafluorophenyl)3]

[(C₃H₂N₂(Ad)2)B(pentafluorophenyl)3]

Refernces

• 1、 Barnett, Christopher,Cole, Marcus L.,Harper, Jason B.. "Steric Properties of N-Heterocyclic Carbenes affect the Performance of Electronic Probes". supporting information. p. 4954 - 4958. Retrieved 2021/12/02.
• 2、 Miyazaki, Yosuke,Yamada, Yuuya,Nakao, Yoshiaki,Hiyama, Tamejiro. "Regioselective hydrocarbamoylation of 1-alkenes". supporting information; experimental part. p. 298 - 300. Retrieved 2012/05/20.