4277-14-9

Basic information

• Product Name: 5-methyl-2-(propan-2-yl)cyclohexyl 4-nitrobenzoate
• Synonyms: 2-Isopropyl-5-methylcyclohexyl 4-nitrobenzoate; Cyclohexanol, 5-methyl-2-(1-methylethyl)-, 4-nitrobenzoate
• CAS NO: 4277-14-9
• Molecular Formula: C₁₇H₂₃NO₄
• Molecular Weight: 305.3688
• Mol File: 4277-14-9.mol
• Article Data: 15

Chemical Properties

• Boiling Point: 419.1°C at 760 mmHg
• Flash Point: 158.6°C
• Density: 1.13g/cm³
• Vapor Pressure: 3.11E-07mmHg at 25°C
• Refractive Index: 1.533
• CAS DataBase Reference: 5-methyl-2-(propan-2-yl)cyclohexyl 4-nitrobenzoate(CAS DataBase Reference)
• NIST Chemistry Reference: 5-methyl-2-(propan-2-yl)cyclohexyl 4-nitrobenzoate(4277-14-9)
• EPA Substance Registry System: 5-methyl-2-(propan-2-yl)cyclohexyl 4-nitrobenzoate(4277-14-9)

Safety Data

• Hazardous Substances Data: 4277-14-9(Hazardous Substances Data)

Upstream product

• 2216-51-5 (-)-menthol 
• 99-77-4 ethyl 4-nitrobenzoate 
• 122-04-3 4-nitro-benzoyl chloride 
• 62-23-7 4-nitro-benzoic acid 
• 67392-57-8 (1R,2S,5R)-5-methyl-2-(1-methylethyl)cyclohexyl ester of diphenylphosphinous acid 
• 15356-70-4 menthol 

Downstream Products

• 5447-71-2 (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 4-aminobenzoate 
• 75350-80-0 8-fluoromenthyl p-nitrobenzoate 
• 75350-81-1 1,8-difluoromenthol p-nitrobenzoate 
• 2216-51-5 (-)-menthol 
• 75350-82-2 isopulegol 

Relevant articles and documents

Copper-free Sandmeyer-type Reaction for the Synthesis of Sulfonyl Fluorides

A copper-free Sandmeyer-type fluorosulfonylation reaction is reported. Utilizing Na2S2O5 and Selectfluor as the sulfur dioxide and fluorine sources, respectively, aryldiazonium salts were transformed into sulfonyl fluorides. The one-pot direct synthesis of sulfonyl fluorides from aromatic amines was also realized via in situ diazotization. The practicality of this method was demonstrated by the broad functional group tolerance, gram-scale synthesis, and late-stage fluorosulfonylation of natural products and pharmaceuticals.

Systematic Evaluation of 2-Arylazocarboxylates and 2-Arylazocarboxamides as Mitsunobu Reagents

2-Arylazocarboxylate and 2-arylazocarboxamide derivatives can serve as replacements of typical Mitsunobu reagents such as diethyl azodicarboxylate. A systematic investigation of the reactivity and physical properties of those azo compounds has revealed that they have an excellent ability as Mitsunobu reagents. These reagents show similar or superior reactivity as compared to the known azo reagents and are applicable to the broad scope of substrates. pKa and steric effects of substrates have been investigated, and the limitation of the Mitsunobu reaction can be overcome by choosing suitable reagents from the library of 2-arylazocarboxylate and 2-aryl azocarboxamide derivatives. Convenient recovery of azo reagents is available by one-pot iron-catalyzed aerobic oxidation, for example. SC-DSC analysis of representative 2-arylazocarboxylate and 2-arylazocarboxamide derivatives has shown high thermal stability, indicating that these azo reagents possess lower chemical hazard compared with typical azo reagents.

Synthesis, antimicrobial evaluation, and QSAR analysis of 2-isopropyl-5-methylcyclohexanol derivatives

A series of 2-isopropyl-5-methylcyclohexanol derivatives were synthesized and evaluated for their antibacterial activity against Gram-positive Staphylococcus aureus and Bacillus subtilis and Gram-negative Escherichia coli and in vitro antifungal activity against Candida albicans and Aspergillus niger. The results of antimicrobial activity demonstrated that the compounds 10, 20, and 21 were the most active ones among the synthesized compounds. The QSAR studies revealed the importance of dipole moment (μ), total energy (Te), and topological parameters (κ1 and κ3) in describing the antimicrobial activity of 2-isopropyl-5-methylcyclohexanol derivatives. Springer Science+Business Media, LLC 2011.