Description

1,3-Bis(1-adamantyl)benzimidazolium chloride (CAS No. 852634-41-4) is a highly specialized organic compound with the molecular formula C₂₇H₃₅ClN₂. This benzimidazolium salt features two adamantyl groups, which confer exceptional steric bulk and chemical stability, making it a valuable precursor for N-heterocyclic carbene (NHC) ligands in organometallic catalysis. The compound exhibits high purity (>98%) and is supplied as a crystalline solid, ideal for research applications requiring precise stoichiometry. Its unique structure enables applications in asymmetric synthesis, polymerization catalysts, and materials science. Store under inert conditions to maintain stability.

Properties

• CAS Number: 852634-41-4
• Complexity: 556
• IUPAC Name: 1,3-bis(1-adamantyl)benzimidazol-3-ium;chloride
• InChI: InChI=1S/C27H35N2.ClH/c1-2-4-25-24(3-1)28(26-11-18-5-19(12-26)7-20(6-18)13-26)17-29(25)27-14-21-8-22(15-27)10-23(9-21)16-27;/h1-4,17-23H,5-16H2;1H/q+1;/p-1
• InChI Key: GMYUUHXEUIPSKA-UHFFFAOYSA-M
• Exact Mass: 422.2488768
• Molecular Formula: C27H35ClN2
• Molecular Weight: 423.0
• SMILES: C1C2CC3CC1CC(C2)(C3)N4C=[N+](C5=CC=CC=C54)C67CC8CC(C6)CC(C8)C7.[Cl-]
• Topological: 8.8
• Monoisotopic Mass: 422.2488768
• Synonyms: 852634-41-4, 1,3-Bis(1-adamantyl)benzimidazolium chloride, 999-183-6, 1,3-bis(1-adamantyl)-benzimidazolium chloride, 1,3-Di(adamantan-1-yl)-1H-benzo[d]imidazol-3-ium chloride, 1,3-BIS-(ADMANT-1-YL)-BENZIMIDAZOLIUM CHLORIDE, 1,3-Bis(1-adamanthyl)benzimidazolium chloride, MFCD08705246, SCHEMBL1077515, CS-0203313, H38092, 1,3-bis(1-adamantyl)benzimidazol-3-ium;chloride, 1,3-Bis(1-adamanthyl)benzimidazolium chloride, 95%, 1,3-Bis(1-adamantyl)benzimidazolium chloride,min. 97%, 1,3-Di(adamantan-1-yl)-1H-benzo[d]imidazol-3-iumchloride

Application

1,3-Bis(1-adamantyl)benzimidazolium chloride is primarily used as a precursor for sterically hindered N-heterocyclic carbene (NHC) ligands, which are pivotal in transition-metal catalysis for C-C bond formation. Its bulky adamantyl groups enhance catalyst stability and selectivity in asymmetric organic transformations. Researchers also employ it in the development of ionic liquids and polymeric materials due to its rigid, hydrophobic framework. The compound is particularly useful in exploring novel catalytic systems for pharmaceutical and fine chemical synthesis.

Safety and Hazards

GHS Hazard Statements

• H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
• H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
• H335 (100%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

Precautionary Statements

• P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501

Hazard Classes and Categories

• Skin Irrit. 2 (100%)
• Eye Irrit. 2 (100%)
• STOT SE 3 (100%)

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