538-93-2 Usage
Description
Isobutylbenzene is an alkylbenzene that is benzene carrying an isobutyl substituent. It is synthesized by the isopropylation at the side chain over Na, K, and Cs exchanged zeolites. Isobutylbenzene is an organic, aromatic, neutral, and colorless liquid with a specific gravity of around 0.852. It is less dense than water, insoluble in water, and soluble in ethanol, ether, benzene, and acetone. The vapors of isobutylbenzene are heavier than air, and it has an odor resembling butylbenzene, tert-butylbenzene, ethylbenzene, or toluene.
Uses
Used in Perfumery:
Isobutylbenzene is used as an intermediate in the perfumery industry due to its distinct odor, which resembles that of butylbenzene, tert-butylbenzene, ethylbenzene, or toluene.
Used in Pharmaceutical Industry:
Isobutylbenzene is used as an intermediate for the synthesis of analgesic anti-inflammatory drugs, such as Ibuprofen, which are widely used for pain relief and reducing inflammation.
Used in Agricultural Research:
Isobutylbenzene is used as an internal standard in the study of increased pigmentation and floral scent levels in Pap1-transgenic petunia, which helps researchers understand the genetic factors affecting these traits in plants.
Preparation
Isobutylbenzene synthesis: Isobutyrophenone, underwent a Wolff–Kishner reduction using hydrazine hydrate and strong base conditions to synthesize isobutyl benzene. The solvent for this reaction was replaced with the more sustainable solvent glycerol. The glycerol for this reaction was obtained from the synthesis of biodiesel. The reaction was allowed to heat at reflux (149–155 °C) for a period of three hours. An average 51 % yield of isobutyl benzene was obtained from the solar synthesis, compared to a 55 % yield from an in-lab, electrical heating analysis.
Synthesis Reference(s)
Journal of the American Chemical Society, 73, p. 4343, 1951 DOI: 10.1021/ja01153a092Synthetic Communications, 26, p. 763, 1996 DOI: 10.1080/00397919608086751Tetrahedron Letters, 27, p. 6369, 1986 DOI: 10.1016/S0040-4039(00)87811-9
Hazard
Moderate fire risk. Toxic in high concentration, a skin and eye irritant.
Environmental fate
Biological. Oxidation of isobutylbenzene by Pseudomonas desmolytica S44B1 and
Pseudomonas convexa S107B1 yielded 3-isobutylcatechol and (+)-2-hydroxy-8-methyl-6-oxononanoic
acid (Jigami et al., 1975).
Chemical/Physical. Complete combustion in air yields carbon dioxide and water vapor.
Isobutylbenzene will not hydrolyze because it has no hydrolyzable functional group.
Check Digit Verification of cas no
The CAS Registry Mumber 538-93-2 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,3 and 8 respectively; the second part has 2 digits, 9 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 538-93:
(5*5)+(4*3)+(3*8)+(2*9)+(1*3)=82
82 % 10 = 2
So 538-93-2 is a valid CAS Registry Number.
InChI:InChI=1/C10H14/c1-9(2)8-10-6-4-3-5-7-10/h3-7,9H,8H2,1-2H3
538-93-2Relevant articles and documents
Synthesis of 1-(3-tert-butyldimethylsiloxy)phenyl-5,5-dimethyl-2,7,8-trioxabicyclo[4.2.0] octanes: New dioxetanes giving high chemiexcitation yields in thermolysis and in fluoride-induced CIEEL-decay
Matsumoto, Masakatsu,Murayama, Junko,Nishiyama, Masao,Mizoguchi, Yasuko,Sakuma, Toshimitsu,Watanabe, Nobuko
, p. 1523 - 1527 (2002)
Dioxetanes with annelated six-membered ring, 1-(3-tert-butyldimethylsiloxy)phenyl-5,5-dimethyl-2,7,8-trioxabicyclo[4.2.0] octanes (2a-2c) were synthesized by singlet oxygenation of the corresponding aryl-substituted dihydropyrans (3). Thermolysis of 2a-2c gave the corresponding ketoesters (5a-5c) as a normal decomposition product together with a considerable amount (23-26%) of ester (6) derived from Norrish type I reaction of the triplet-excited ester (5). On the other hand, treatment with tetrabutylammonium fluoride (TBAF) in DMSO induced rapid decomposition of 2 to emit blue light in high chemiexcitation yield (72-75%) of the oxyanion of a ketoester (10). These results show that the chemiexcitation efficiency of dioxetanes (2) was higher than that of their five-membered ring analog (1) not only for thermolysis and but also for the base-induced CIEEL.
Site-Specific Alkene Hydromethylation via Protonolysis of Titanacyclobutanes
Bartfield, Noah M.,Frederich, James H.,Law, James A.
supporting information, p. 14360 - 14364 (2021/05/27)
Methyl groups are ubiquitous in biologically active molecules. Thus, new tactics to introduce this alkyl fragment into polyfunctional structures are of significant interest. With this goal in mind, a direct method for the Markovnikov hydromethylation of alkenes is reported. This method exploits the degenerate metathesis reaction between the titanium methylidene unveiled from Cp2Ti(μ-Cl)(μ-CH2)AlMe2 (Tebbe's reagent) and unactivated alkenes. Protonolysis of the resulting titanacyclobutanes in situ effects hydromethylation in a chemo-, regio-, and site-selective manner. The broad utility of this method is demonstrated across a series of mono- and di-substituted alkenes containing pendant alcohols, ethers, amides, carbamates, and basic amines.
ISOBUTYL BENZENE AND A PROCESS FOR SYNTHESIS OF ISOBUTYL BENZENE BY USING A CATALYST
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Page/Page column 13; 16-17, (2020/12/11)
The present disclosure provides a process for the synthesis of isobutyl benzene by side chain alkylation of toluene in the presence of a catalyst. The catalyst used ub the process of present disclosure provides maximum conversion of toluene with high selectivity towards isobutyl benzene.