1,3-Di-tert-butylimidazol-2-ylidene

Base Information

• Chemical Name: 1,3-Di-tert-butylimidazol-2-ylidene
• CAS No.: 157197-53-0
• Molecular Formula: C11H20 N2
• Molecular Weight: 180.293
• Hs Code.: 29332900
• European Community (EC) Number: 677-194-4
• DSSTox Substance ID: DTXSID20449891
• Wikidata: Q72470038
• Mol file: 157197-53-0.mol

Synonyms:157197-53-0;1,3-Di-tert-butylimidazol-2-ylidene;1,3-Di-tert-butyl-1H-imidazol-3-ium-2-ide;1,3-ditert-butyl-2H-imidazol-1-ium-2-ide;1,3-DI-T-BUTYLIMIDAZOL-2-YLIDENE;ItBu;DTXSID20449891;MFCD03788921;SC11706;AS-65263;D3472;A907664;1,3-DI-TERT-BUTYL-1,3-DIHYDRO-2H-IMIDAZOL-2-YLIDENE;1,3-DI-TERT-BUTYLIMIDAZOL-2-YLIDENE;ITBU

Chemical Property of 1,3-Di-tert-butylimidazol-2-ylidene

Chemical Property:

• Vapor Pressure: 0.056mmHg at 25°C
• Melting Point: 71-72°C
• Boiling Point: 233.32°C at 760 mmHg
• Flash Point: 86.27°C
• PSA: 6.48000
• LogP: 2.25790
• Storage Temp.: Refrigerator
• Sensitive.: air sensitive, moisture sensitiv
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 180.162648646
• Heavy Atom Count: 13
• Complexity: 222

Purity/Quality:

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

1,3-Di-t-butylimidazol-2-ylidene ^*data from reagent suppliers

Safty Information:

• Statements: 36/37/38
• Safety Statements: 26-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)N1C=C[N+](=[C-]1)C(C)(C)C

Technology Process of 1,3-Di-tert-butylimidazol-2-ylidene

There total 12 articles about 1,3-Di-tert-butylimidazol-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: 78.0%

1,3-dimesitylimidazolium tetrafluoroborate → 1,3-di-tert-butylimidazol-2-ylidene (157197-53-0)

Guidance literature:

With potassium tert-butylate; sodium hydride; In tetrahydrofuran; for 12h; Schlenk technique; Inert atmosphere;

DOI:10.1021/acs.organomet.7b00838

Reference yield: 41.0%

C11H21N2(1+)*2BF4(1-)*H(1+) → 1,3-di-tert-butylimidazol-2-ylidene (157197-53-0)

Guidance literature:

With potassium tert-butylate; sodium hydride; In tetrahydrofuran; for 12h;

DOI:10.1021/ja043249f

Reference yield:

C17H11(1-)*C11H21N2(1+) → benzo[c]fluorene (205-12-9) + 1,3-di-tert-butylimidazol-2-ylidene (157197-53-0)

Guidance literature:

In tetrahydrofuran; at 25 ℃; Equilibrium constant;

DOI:10.1021/ja025628j

upstream raw materials:

1,3-di-tert-butyl-1H-imidazol-3-ium chloride

formaldehyd

Glyoxal

tert-butylamine

Downstream raw materials:

[tBu₂ImH][HB(C₆F₅)3]

1,3-di-tert-butylimidazolium-4-yl-tris(pentafluorophenyl)borate

Refernces

• 1、 Scott, Natalie M.,Dorta, Reto,Stevens, Edwin D.,Correa, Andrea,Cavallo, Luigi,Nolan, Steven P.. "Interaction of a bulky N-heterocyclic carbene ligand with Rh(I) and Ir(I). Double C-H activation and isolation of bare 14-electron Rh(III) and Ir(III) complexes". . p. 3516 - 3526. Retrieved 2005.
• 2、 Arduengo III, Anthony J.,Bock, Hans,Chen, Han,Denk, Michael,Dixon, David A.,Green, Jennifer C.,Hermann, Wolfgang A.,Jones, Nancy L.,Wagner, Matthias,West, Robert. "Photoelectron spectroscopy of a carbene/silylene/germylene series". . p. 6641 - 6649. Retrieved 1994.
• 3、 Bole, Leonie J.,Uzelac, Marina,Hernán-Gómez, Alberto,Kennedy, Alan R.,O'Hara, Charles T.,Hevia, Eva. "Progressing the Frustrated Lewis Pair Abilities of N-Heterocyclic Carbene/GaR3Combinations for Catalytic Hydroboration of Aldehydes and Ketones". supporting information. p. 13784 - 13796. Retrieved 2021/07/26.
• 4、 Kleeberg, Christian,Borner, Corinna. "Syntheses, Structures, and Reactivity of NHC Copper(I) Boryl Complexes: A Systematic Study". . p. 4136 - 4146. Retrieved 2018/11/23.