45676-04-8

Basic information

• Product Name: 1-tert-Butyl-1H-imidazole
• Synonyms: 1-tert-Butyl-1H-imidazole;1-t-ButyliMidazole;1-tert-Butylimidazole;1-tert-Butylimidazole
• CAS NO: 45676-04-8
• Molecular Formula: C₇H₁₂N₂
• Molecular Weight: 124.18358
• Mol File: 45676-04-8.mol
• Article Data: 15

Chemical Properties

• Boiling Point: 105°C/12mmHg(lit.)
• Flash Point: 85.8°C
• Appearance: /
• Density: 0.92g/cm³
• Vapor Pressure: 0.188mmHg at 25°C
• Refractive Index: 1.4800 to 1.4840
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 7.22±0.30(Predicted)
• CAS DataBase Reference: 1-tert-Butyl-1H-imidazole(CAS DataBase Reference)
• NIST Chemistry Reference: 1-tert-Butyl-1H-imidazole(45676-04-8)
• EPA Substance Registry System: 1-tert-Butyl-1H-imidazole(45676-04-8)

Safety Data

• Hazardous Substances Data: 45676-04-8(Hazardous Substances Data)

Usage

General Description

1-tert-Butyl-1H-imidazole is a chemical compound with the molecular formula C7H11N2. It is an imidazole derivative with a tert-butyl group attached to the nitrogen atom. 1-tert-Butyl-1H-imidazole is commonly used as a ligand in coordination chemistry and as a catalyst in organic synthesis. It has also been investigated for its potential use in pharmaceutical applications, particularly in the development of antiviral and anticancer drugs. 1-tert-Butyl-1H-imidazole is a white solid at room temperature and is soluble in various organic solvents. It is important to handle this compound with care, as it can be harmful if ingested, inhaled, or comes into contact with the skin.

InChI:InChI=1/C7H12N2/c1-7(2,3)9-5-4-8-6-9/h4-6H,1-3H3

Upstream product

• 288-32-4 1H-imidazole 
• 507-20-0 tertiary butyl chloride 
• 50-00-0 formaldehyd 
• 131543-46-9 Glyoxal 
• 75-64-9 tert-butylamine 
• 61640-27-5 1-(tert-butyl)-2-mercaptoimidazole 
• 590-42-1 tert-butyl isothiocyanate 
• 117983-76-3 1-tert-butyl-3-(2,2-diethoxyethyl)thiourea 
• 507-19-7 t-butyl bromide 

Downstream Products

• 90408-26-7 1-t-butylimidazol-2-yldiphenylmethanol 
• 937790-29-9 1-(tert-butyl)-3-(3,5-di-tertbutyl-2-hydroxyphenyl)-1H-imidazol-3-ium bromide 

Relevant articles and documents

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Steric effect of NHC ligands in Pd(II)–NHC-catalyzed non-directed C–H acetoxylation of simple arenes

Although there has been a lot of progress in oxidative arene C–H functionalization reactions catalyzed by Pd(II/IV) system, the non-directed, site-selective functionalization of arene molecules is still challenging. It has been established that ligands play a pivotal role in controlling rate- as well as selectivity-determining step in a catalytic cycle involving well-defined metal-ligand bonding. N-heterocyclic carbene (NHC) ligands have had a tremendous contribution in the recent extraordinary success of achieving high reactivity and excellent selectivity in many catalytic processes including cross-coupling and olefin-metathesis reactions. However, the immense potential of these NHC ligands in improving site-selectivity of non-directed catalytic C–H functionalization reactions of simple arenes is yet to be realized, where overriding the electronic bias on deciding selectivity is a burdensome task. The presented work demonstrated an initiative step in this regard. Herein, a series of well-defined discrete [Pd(NHCR′R)(py)I2] complexes with systematically varied degree of spatial congestion at the Pd centre, exerted through the R and R’ substituents on the NHC ligand, were explored in controlling the activity as well as the site-selectivity of non-directed acetoxylation of representative monosubstituted and disubstituted simple arenes (such as toluene, iodobenzene and bromobenzene, naphthalene and 1,2-dichlorobenzene). The resulting best yields were found to be 75% for toluene and 65% for bromobenzene with [Pd(NHCMePh)(py)I2], 75% for iodobenzene and 79% for naphthalene with [Pd(NHCMeMe)(py)I2], and 41% for 1,2-dichlorobenzene with [Pd(NHCCyCy)(py)I2]. Most importantly, with increasing the bulkiness of the NHC ligand in the complexes, the selectivity of the distal C-acetoxylated products in comparison to the proximal ones, was enhanced to a great extent in all cases. Considering the vast library of NHC ligands, this study underscores the future opportunity to develop more strategies to improve the activity and the crucial site-selectivity of C–H functionalization reactions in simple as well as complex organic molecules.

N-Heterocyclic carbene rhodium(i) complexes containing an axis of chirality: Dynamics and catalysis

The novel rhodium(i) complexes [RhCl(NBD)(NHC)] [NBD = norbornadiene, NHC = 1-benzyl-3-R-imidazolin-2-ylidene; R = Me (3a), Bz (3b), Tr (3c), tBu (3d)], containing on one nitrogen the benzyl substituent and on the other increasing bulky alkyl substituents were prepared. All the complexes display restricted rotation around the metal-carbene bond and yield conformational enantiomers. The stereodynamics and racemization barriers about the Rh-carbene have been determined by means of NMR spectroscopy for 3a-c, whereas for the bulkiest 3d only the lower limit (91 kJ mol-1) could be calculated. Whilst the racemization barriers obtained by DFT calculations for 3a,b and 3d matched the experimental values, in the case of 3c the latter (62.3 kJ mol-1) was much smaller with respect to the calculated one (101.7 kJ mol-1). The lower experimental barrier has been attributed to a dissociative pathway that produces a solvated ionic pair in the transition state. The catalytic activity of the neutral rhodium(i) complexes 3a and 3d in the hydrosilylation with HSiMe2Ph of the terminal alkynes PhC≡CH, TolC≡CH, nBuC≡CH, Et3SiC≡CH, and (CPh2OH)C≡CH has been investigated, and compared with the amide-functionalized [RhCl(NBD){1-(2-NHBoc-ethyl)-3-Me-imidazolin-2-ylidene}] (4) and with [RhCl(NBD){1-butyl-3-Me-imidazolin-2-ylidene}] (5).