131042-77-8

Basic information

• Product Name: 1,3-BIS(1-ADAMANTYL)IMIDAZOL-2-YLIDENE
• Synonyms: ARDUENGO'S CARBENE;1,3-BIS(1-ADAMANTYL)IMIDAZOL-2-YLIDENE;1,3-Bis(1-adamantyl)imidazol-2-ylidene,min.98%ARDUENGO'SCARBENE;1,3-Bis(1-adaMantyl)iMidazol-2-ylidene ARDUENGO'S CARBENE;1,3-Bis(1-adamantyl)-1,3-dihydro-2H-imidazol-2-ylidene;1,3-Bis(adamantan-1-yl)-1,3-dihydro-2H-imidazol-2-ylidene;1,3-Diadamantylimidazol-2-ylidene;1,3-Bis(1-adamantyl)imidazol-2-ylidene,98% ARDUENGO'S CARBENE
• CAS NO: 131042-77-8
• Molecular Formula: C₂₃H₃₂N₂
• Molecular Weight: 336.51
• Mol File: 131042-77-8.mol
• Article Data: 5

Chemical Properties

• Melting Point: 240-241°C
• Appearance: white/crystal
• Refractive Index: 1.641
• Sensitive: air sensitive, moisture sensitiv
• CAS DataBase Reference: 1,3-BIS(1-ADAMANTYL)IMIDAZOL-2-YLIDENE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-BIS(1-ADAMANTYL)IMIDAZOL-2-YLIDENE(131042-77-8)
• EPA Substance Registry System: 1,3-BIS(1-ADAMANTYL)IMIDAZOL-2-YLIDENE(131042-77-8)

Safety Data

• Statements: 10
• Safety Statements: 9-16
• RIDADR: 1325
• Hazardous Substances Data: 131042-77-8(Hazardous Substances Data)

Usage

General Description

1,3-BIS(1-ADAMANTYL)IMIDAZOL-2-YLIDENE, also known as ADAIM, is a type of N-heterocyclic carbene (NHC) which belongs to the class of compounds containing a nitrogen atom in a heterocyclic compound. It is a relatively strong base and nucleophile, and is predominantly used as a ligand in metal complex catalysts, being involved in many catalytic transformations. This chemical has an imidazole ring with an adamantly group on either side of the nitrogen atom, which can stabilize the carbene and make it more robust for various reactions. As a result of this, ADAIM is a highly effective catalyst and has found use in industries ranging from pharmaceuticals to agriculture.

InChI:InChI=1/C23H34N2/c1-2-25(23-12-19-6-20(13-23)8-21(7-19)14-23)15-24(1)22-9-16-3-17(10-22)5-18(4-16)11-22/h1-2,16-21H,3-15H2/t16-,17+,18-,19-,20+,21-,22-,23-

Upstream product

• 286014-42-4 1,3-di(adamantan-1-yl)-1H-imidazol-3-ium tetrafluoroborate 
• 768-94-5 1-Adamantanamine 
• 131042-78-9 1,3-di(adamantan-1-yl)-1H-imidazol-3-ium chloride 

Downstream Products

• 1313574-26-3 [((1,3-di-1-adamanthylimidazolin-2-ylidene)(+1H))][(hydride)B(pentafluorophenyl)3] 
• 1313574-27-4 [(C₃H₂N₂(Ad)2)B(pentafluorophenyl)3] 

Relevant articles and documents

A stable crystalline carbene

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A closer look at the reactivity between N-heterocyclic carbenes and fluoroalkenes

The fundamental reactivity leading to N-heterocyclic fluoroalkene adducts is explored in detail, featuring a total of 15 N-heterocyclic carbenes (NHCs) with various electronic and steric environments. The activity of these carbenes towards tetrafluoroethylene (TFE), hexafluoropropene (HFP), trifluoroethylene (HTFE) and vinylidene fluoride (VDF) is assessed in THF and toluene. Attempts were made to correlate the observed reactivity with electronic (Tolman Electronic Parameters) and steric (% buried volume) parameters unique to each NHC, but a trend has yet to be fully determined. However, the unique steric constraints of a cyclic (alkyl)(amino)carbene (CAAC) were shown to modify the initial point of nucleophilic attack on HTFE, providing selective transformation to a different adduct than has been observed to date with all reactions involving this fluoroalkene.

Construction of tetrasubstituted carbon by an organocatalyst: Cyanation reaction of ketones and ketimines catalyzed by a nucleophilic N-heterocyclic carbene

A method for cyanation reaction of ketones and ketimines having lower reactivity than aldehydes and aldimines with TMSCN in the presence of N-heterocyclic carbene prepared from 1,3-bis(2,4,6-trimethylphenyl)imidazolium chloride and potassium tert-butoxide