258278-28-3

Basic information

• Product Name: 1,3-Bis(2,6-di-i-propylphenyl)-4,5-dihydroimidazol-2-ylidine,min.98%
• Synonyms: 1,3-Bis(2,6-di-i-propylphenyl)-4,5-dihydroimidazol-2-ylidine,min.98%;1,3-Bis(2,6-di-i-propylphenyl)-4,5-dihydroimidazol-2-ylidine, min. 98%;1,3-Bis(2,6-diisopropylphenyl)imidazolidin-2-ylidene;1,3-Bis(2,6-di-i-propylphenyl)imidazolidin-2-ylidene;1,3-Bis(2,6-diisopropylphenyl)-4,5-dihydro-1H-imidazol-3-ium-2-ide;1,3-Bis(2,6-di-i-propylphenyl)-4,5-dihydroimidazol-2-ylidine,98%;SIPr;1,3-bis(2,6-diisopropylphenyl)-4,5-dihydroimidazol-2-ylidene
• CAS NO: 258278-28-3
• Molecular Formula: C₂₇H₃₈N₂
• Molecular Weight: 390.611
• Product Categories: N-heterocyclic carbene
• Mol File: 258278-28-3.mol
• Article Data: 7

Chemical Properties

• Melting Point: 170-175°C
• Boiling Point: 487.5°C at 760 mmHg
• Flash Point: 215.5°C
• Appearance: white to off-white/Powder
• Vapor Pressure: 1.19E-09mmHg at 25°C
• Storage Temp.: ?20°C
• Solubility: DMSO (Slightly), Ethyl Acetate (Slightly)
• Sensitive: air sensitive, moisture sensitiv
• Stability: Moisture Sensitive
• CAS DataBase Reference: 1,3-Bis(2,6-di-i-propylphenyl)-4,5-dihydroimidazol-2-ylidine,min.98%(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-Bis(2,6-di-i-propylphenyl)-4,5-dihydroimidazol-2-ylidine,min.98%(258278-28-3)
• EPA Substance Registry System: 1,3-Bis(2,6-di-i-propylphenyl)-4,5-dihydroimidazol-2-ylidine,min.98%(258278-28-3)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 258278-28-3(Hazardous Substances Data)

Usage

Uses

SIPr is used as a reagent in the synthesis of mononuclear [(η6-arene)Ni(N-heterocyclic carbene)] complexes which are useful precursors of the Ni0-NHC unit.

InChI:InChI=1/C27H38N2/c1-18(2)22-11-9-12-23(19(3)4)26(22)28-15-16-29(17-28)27-24(20(5)6)13-10-14-25(27)21(7)8/h9-14,18-21H,15-16H2,1-8H3

Upstream product

• 250285-32-6 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride 
• 244187-81-3 1,3-bis-(2,6-diisopropylphenyl)-imidazol-2-ylidene 
• 684283-54-3 1,3-diisopropylbenzimidazol-2-ylidene hydroiodide 
• 1176938-29-6 N,N'-di(2,6-diisopropylphenyl)formamidine 
• 1034137-22-8 1,3-bis[2,6-bis(1-methylethyl)phenyl]-4,5-dihydro-1H-imidazolium bromide 
• 74663-75-5 1,2-bis(2,6-diisopropylphenylimino)ethane 
• 24544-04-5 2,6-diisopropylbenzenamine 
• 258278-25-0 1,3-bis[(2,6-diisopropyl)phenyl]imidazolinium chloride 

Downstream Products

• 478980-01-7 (η3-allyl)(N,N'-bis(2,6-diisopropylphenyl)-4,5-dihydroimidazol-2-ylidene)chloropalladium(II) 
• 840493-74-5 1,3-bis(2,6-diisopropylphenyl)imidazolin-2-imine 
• 1309607-00-8 C₉H₁₈NO^(1-)*C₂₇H₃₉N₂⁽¹⁺⁾ 
• 1309607-02-0 C₁₅H₂₃O^(1-)*C₂₇H₃₉N₂⁽¹⁺⁾ 
• 367940-34-9 [Pd(N,N'-bis[2,6-(diisopropyl)phenyl]imidazolin-2-ylidene)₂] 
• 1352951-79-1 Br^(1-)*C₂₇H₃₈Br₃N₂Si⁽¹⁺⁾ 
• 1352951-80-4 C₂₇H₃₈Br₂N₂Si 
• 1352951-85-9 C₂₇H₃₈Cl₂N₂Si 

Relevant articles and documents

Stable Singlet Carbenes as Organic Superbases

A simple experimental procedure for scaling carbene Br?nsted basicity is described. The results highlight the strong basicity of pyrazol-4-ylidenes, a type of mesoionic carbene, also named cyclic-bentallenes (CBA). They are more basic (pKaH >42.7 in acetonitrile) than the popular proazaphosphatrane Verkade bases, and even the Schwesinger phosphazene superbase P4(tBu). The basicity of these compounds can readily be tuned, and they are accessible in multigram quantities. These results open new avenues for carbon centered superbases.

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.

Expanded ring diaminocarbene palladium complexes: Synthesis, structure, and Suzuki-Miyaura cross-coupling of heteroaryl chlorides in water

A series of new 6- and 7-membered N-heterocyclic carbene (NHC) complexes of palladium (NHC)Pd(cinn)Cl (cinn = cinnamyl = 3-phenylallyl) were synthesized and characterized structurally in the solid state. The influence of ring size (5, 6 or 7) and bulkiness of N-aryl substituents (Mes = 2,4,6-trimethylphenyl, or Dipp = 2,6-diisopropylphenyl) in carbenes on palladium catalysed Suzuki-Miyaura cross-coupling was revealed. Due to the unique stereoelectronic properties of expanded ring NHCs, a versatile, highly efficient green protocol of coupling of heteroaromatic chlorides and bromides with boronic acids has been developed. High quantitative yields of biaryls were achieved with water as solvent, under air, using low catalyst and phase transfer agent loadings, and with mild and environmentally benign base NaHCO3. The Royal Society of Chemistry 2013.