1,3-Bis(2,6-diisopropylphenyl)imidazol-2-ylidene

Base Information

• Chemical Name: 1,3-Bis(2,6-diisopropylphenyl)imidazol-2-ylidene
• CAS No.: 244187-81-3
• Molecular Formula: C27H36N2
• Molecular Weight: 388.596
• Hs Code.: 29332900
• European Community (EC) Number: 679-548-3
• DSSTox Substance ID: DTXSID10460737
• Wikidata: Q72445072
• Mol file: 244187-81-3.mol

Synonyms:1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene

Chemical Property of 1,3-Bis(2,6-diisopropylphenyl)imidazol-2-ylidene

Chemical Property:

• Vapor Pressure: 8.11E-09mmHg at 25°C
• Melting Point: 213-217 °C
• Boiling Point: 464.8 °C at 760 mmHg
• Flash Point: 204.1 °C
• PSA: 6.48000
• LogP: 7.81790
• Storage Temp.: ?20°C
• Sensitive.: air sensitive, moisture sensitiv
• Solubility.: soluble in Methanol
• XLogP3: 8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 6
• Exact Mass: 388.287849157
• Heavy Atom Count: 29
• Complexity: 503

Purity/Quality:

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

1,3-Bis(2,6-Diisopropylphenyl)imidazol-2-ylidene ^*data from reagent suppliers

Safty Information:

• Statements: 10
• Safety Statements: 16

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)C1=C(C(=CC=C1)C(C)C)N2C=C[N+](=[C-]2)C3=C(C=CC=C3C(C)C)C(C)C
• Uses: Ligand for Pd complexes for amination reaction of aryl halides; used as C-C bond formation reaction, e.g. Kumada-Tamao-Corriu reaction, Suzuki coupling, and Stille coupling.

Technology Process of 1,3-Bis(2,6-diisopropylphenyl)imidazol-2-ylidene

There total 23 articles about 1,3-Bis(2,6-diisopropylphenyl)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: 97.0%

1,3-bis(2,6-diisopropylphenyl)-4,5-dihydroimidazole trafluoroborate → 1,3-bis-(2,6-diisopropylphenyl)-imidazol-2-ylidene (244187-81-3)

Guidance literature:

With potassium tert-butylate; In tetrahydrofuran; for 6h;

DOI:10.1021/ja0286876

Reference yield: 95.0%

1,3-bis[2,6-diisopropylphenyl]imidazolium chloride (250285-32-6) → 1,3-bis-(2,6-diisopropylphenyl)-imidazol-2-ylidene (244187-81-3)

Guidance literature:

With [Fe(η5-cyclopentadienyl)(η-benzene)]; oxygen; In tetrahydrofuran-d8; at 20 ℃; for 0.0166667h;

DOI:10.1021/ja058421+

Reference yield: 90.0%

1,3-bis[2,6-bis(1-methylethyl)phenyl]-1,3-dihydro-2H-imidazol-2-ylidene monohydrochloride → 1,3-bis-(2,6-diisopropylphenyl)-imidazol-2-ylidene (244187-81-3)

Guidance literature:

With potassium tert-butylate;

DOI:10.1016/S0022-328X(03)00458-3

upstream raw materials:

1,3-bis[2,6-diisopropylphenyl]imidazolium chloride

2,6-diisopropylbenzenamine

(1E,2E)-N¹,N²-bis(2,6-diisopropylphenyl)-ethane-1,2-diimine

1,2-bis(2,6-diisopropylphenylimino)ethane

Downstream raw materials:

1,3-bis-(2,6-diisopropylphenyl)-4,5-dichloroimidazol-2-ylidene

1,3-bis(2,6-diisopropylphenyl)imidazolylium-2-carboxylate

(p-cymene)Ru(1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene)Cl₂

(1,3-bis-(2,6-diisopropylphenyl)imidazolin-2-ylidene)*AlH₃

Refernces

• 1、 Lv, Aifeng,Freitag, Matthias,Chepiga, Kathryn M.,Sch?fer, Andreas H.,Glorius, Frank,Chi, Lifeng. "N-Heterocyclic-Carbene-Treated Gold Surfaces in Pentacene Organic Field-Effect Transistors: Improved Stability and Contact at the Interface". . . Retrieved 2018.
• 2、 Liger, Fran?ois,Cadarossanesaib, Florence,Iecker, Thibaut,Tourvieille, Christian,Le Bars, Didier,Billard, Thierry. "11C-Labeling: Intracyclic Incorporation of Carbon-11 into Heterocycles". . p. 6968 - 6972. Retrieved 2019.
• 3、 Zuo, Gang,Louie, Janis. "Highly active nickel, catalysts for the isomerization of unactivated vinyl cyclopropanes to cyclopentenes". . p. 2277 - 2279. Retrieved 2004.
• 4、 Roy, Matthew M.D.,Baird, Samuel R.,Ferguson, Michael J.,Rivard, Eric. "Toward N-heterocyclic carbene stabilized zinc sulfides". . p. 173 - 175. Retrieved 2021.
• 5、 Dible, Benjamin R.,Sigman, Matthew S.. "Unusual reactivity of molecular oxygen with π-allylnickel(N-heterocyclic carbene) chloride complexes". . p. 872 - 873. Retrieved 2003.
• 6、 Bertrand, Guy,Grotjahn, Douglas B.,Jazzar, Rodolphe,Junor, Glen P.,Vermersch, Fran?ois,Yazdani, Sima. "Stable Singlet Carbenes as Organic Superbases". supporting information. p. 27253 - 27257. Retrieved 2021/11/22.