637-59-2 Usage
Description
1-Bromo-3-phenylpropane, a colorless to light yellow liquid, is an organic compound with the molecular formula C9H11Br. It is characterized by the presence of a bromine atom attached to a three-carbon propane chain, with a phenyl group attached to the second carbon.
Uses
1. Used in Pharmaceutical Industry:
1-Bromo-3-phenylpropane is used as a synthetic intermediate for the development of MraY natural inhibitors. These inhibitors serve as potent antibacterial agents, targeting bacterial cell wall synthesis and providing a means to combat bacterial infections.
2. Used in Chemical Research:
1-Bromo-3-phenylpropane is utilized in the preparation of quinolinone derivatives, which are known for their potent and selective inhibition of monoamine oxidase-B (MAO-B). This application is particularly relevant in the field of neuroscience and psychiatric research, as MAO-B inhibitors can be used to treat conditions such as Parkinson's disease and major depressive disorder.
3. Used in Organic Synthesis:
In addition to its pharmaceutical applications, 1-Bromo-3-phenylpropane can be employed as a versatile building block in various organic synthesis processes. Its unique structure allows for further functionalization and modification, making it a valuable compound in the synthesis of a wide range of organic molecules.
Synthesis Reference(s)
Chemical and Pharmaceutical Bulletin, 31, p. 4189, 1983 DOI: 10.1248/cpb.31.4189
Purification Methods
Wash the bromide successively with conc H2SO4, water, 10% aqueous Na2CO3 and again with water, then dry it with CaCl2 and fractionally distil it just before use. [Beilstein 5 IV 982.]
Check Digit Verification of cas no
The CAS Registry Mumber 637-59-2 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 6,3 and 7 respectively; the second part has 2 digits, 5 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 637-59:
(5*6)+(4*3)+(3*7)+(2*5)+(1*9)=82
82 % 10 = 2
So 637-59-2 is a valid CAS Registry Number.
InChI:InChI=1/C9H11Br/c10-8-4-7-9-5-2-1-3-6-9/h1-3,5-6H,4,7-8H2
637-59-2Relevant articles and documents
Recent advances in heterolytic nucleofugal leaving groups
Lepore, Salvatore D.,Mondal, Deboprosad
, p. 5103 - 5122 (2007)
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Iron(II) and Copper(I) Control the Total Regioselectivity in the Hydrobromination of Alkenes
Cruz, Daniel A.,Sinka, Victoria,De Armas, Pedro,Steingruber, Hugo Sebastian,Fernández, Israel,Martín, Víctor S.,Miranda, Pedro O.,Padrón, Juan I.
supporting information, p. 6105 - 6109 (2021/08/18)
A new method that allows the complete control of the regioselectivity of the hydrobromination reaction of alkenes is described. Herein, we report a radical procedure with TMSBr and oxygen as common reagents, where the formation of the anti-Markovnikov product occurs in the presence of parts per million amounts of the Cu(I) species and the formation of the Markovnikov product occurs in the presence of 30 mol % iron(II) bromide. Density functional theory calculations combined with Fukui's radical susceptibilities support the obtained results.
Boron tribromide as a reagent for anti-Markovnikov addition of HBr to cyclopropanes
Chen, Shuming,Gieuw, Matthew H.,Houk, K. N.,Ke, Zhihai,Yeung, Ying-Yeung
, p. 9426 - 9433 (2020/10/02)
Although radical formation from a trialkylborane is well documented, the analogous reaction mode is unknown for trihaloboranes. We have discovered the generation of bromine radicals from boron tribromide and simple proton sources, such as water ortert-butanol, under open-flask conditions. Cyclopropanes bearing a variety of substituents were hydro- and deuterio-brominated to furnish anti-Markovnikov products in a highly regioselective fashion. NMR mechanistic studies and DFT calculations point to a radical pathway instead of the conventional ionic mechanism expected for BBr3