538-93-2 Usage
Chemical Properties
Isobutyl Benzene is an organic, aromatic, neutral and colourless liquid that has a specific gravity of around 0.852. Less dense than water and insoluble in water, soluble in ethanol, ether, benzene and acetone. Vapors heavier than air.
Physical properties
Clear, colorless, liquid with an odor resembling butylbenzene, tert-butylbenzene, ethylbenzene, or
toluene. An odor threshold concentration of 80 μg/kg was reported (quoted, Verschueren, 1983)
Uses
Isobutylbenzene is used as an intermediate for perfumery and analgesic anti-inflammatory (Ibuprofen). It is also used as an internal standard in the study of increased pigmentation and floral scent levels in Pap1-transgenic petunia.
Definition
ChEBI: Isobutylbenzene is an alkylbenzene that is benzene carrying an isobutyl substituent.
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
General Description
Isobutylbenzene is synthesized by the isopropylation at the side chain over Na, K and Cs exchanged zeolites.
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.
Zn-Mediated Hydrodeoxygenation of Tertiary Alkyl Oxalates
Ye, Yang,Ma, Guobin,Yao, Ken,Gong, Hegui
supporting information, p. 1625 - 1628 (2021/01/18)
Herein we describe a general, mild, and scalable method for hydrodeoxygenation of readily accessible tertiary alkyl oxalates by Zn/silane under Ni-catalyzed conditions. The reduction method is suitable for an array of structural motifs derived from tertiary alcohols that bear diverse functional groups, including the synthesis of a key intermediate en route to estrone.
Photocatalytic transfer hydrogenolysis of aromatic ketones using alcohols
Gao, Zhuyan,Han, Jianyu,Hong, Feng,Lei, Lijun,Li, Hongji,Liu, Huifang,Luo, Nengchao,Wang, Feng
, p. 3802 - 3808 (2020/07/09)
A mild method of photocatalytic deoxygenation of aromatic ketones to alkyl arenes was developed, which utilized alcohols as green hydrogen donors. No hydrogen evolution during this transformation suggested a mechanism of direct hydrogen transfer from alcohols. Control experiments with additives indicated the role of acid in transfer hydrogenolysis, and catalyst characterization confirmed a larger number of Lewis acidic sites on the optimal Pd/TiO2 photocatalyst. Hence, a combination of hydrogen transfer sites and acidic sites may be responsible for efficient deoxygenation without additives. The photocatalyst showed reusability and achieved selective reduction in a variety of aromatic ketones.