772-33-8 Usage
Uses
Used in Chemical Synthesis:
2-Hydroxy-5-nitrobenzyl bromide is used as a reagent for sulfhydryl modification, allowing for the covalent attachment of 2-HYDROXY-5-NITROBENZYL BROMIDE to sulfhydryl-containing molecules. This modification can alter the properties and reactivity of the target molecules, which is useful in the development of new chemical entities and the study of molecular interactions.
Used in Pharmaceutical and Biochemical Research:
In the pharmaceutical and biochemical research industries, 2-Hydroxy-5-nitrobenzyl bromide is used as a reagent for the covalent modification of tryptophan and tryptophan residues in proteins. This modification can help researchers study the structure, function, and stability of proteins, as well as their interactions with other biomolecules.
Used in Immunology:
2-Hydroxy-5-nitrobenzyl bromide has been used in the covalent modification of tryptophan residues in monoclonal immunoglobulins. This modification can affect the immunological properties of these antibodies, potentially enhancing their specificity, affinity, or stability for use in diagnostic or therapeutic applications.
Overall, 2-Hydroxy-5-nitrobenzyl bromide is a valuable chemical reagent with applications in various scientific fields, including chemical synthesis, pharmaceutical and biochemical research, and immunology. Its ability to modify specific functional groups in biomolecules makes it a versatile tool for the development and study of new compounds and the understanding of molecular interactions.
Synthesis Reference(s)
Journal of the American Chemical Society, 86, p. 1448, 1964 DOI: 10.1021/ja01061a045
Purification Methods
Crystallise the bromide from *benzene or *benzene/ligroin. It is slightly soluble in EtOH, soluble in *C6H6 and AcOH, and very soluble in ligroin. [Beilstein 6 H 367.]
Check Digit Verification of cas no
The CAS Registry Mumber 772-33-8 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 7,7 and 2 respectively; the second part has 2 digits, 3 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 772-33:
(5*7)+(4*7)+(3*2)+(2*3)+(1*3)=78
78 % 10 = 8
So 772-33-8 is a valid CAS Registry Number.
InChI:InChI=1/C7H6BrNO3/c8-4-5-3-6(9(11)12)1-2-7(5)10/h1-3,10H,4H2/p-1
772-33-8Relevant academic research and scientific papers
Substituent effects on oxidation-induced formation of quinone methides from arylboronic ester precursors
Cao, Sheng,Christiansen, Robin,Peng, Xiaohua
, p. 9050 - 9058 (2013/07/26)
A series of arylboronic esters containing different aromatic substituents and various benzylic leaving groups (Br or N+Me3Br -) have been synthesized. The substituent effects on their reactivity with H2O2 and formation of quinone methide (QM) have been investigated. NMR spectroscopy and ethyl vinyl ether (EVE) trapping experiments were used to determine the reaction mechanism and QM formation, respectively. QMs were not generated during oxidative cleavage of the boronic esters but by subsequent transformation of the phenol products under physiological conditions. The oxidative deboronation is facilitated by electron-withdrawing substituents, such as aromatic F, NO2, or benzylic N+Me 3Br-, whereas electron-donating substituents or a better leaving group favor QM generation. Compounds containing an aromatic CH 3 or OMe group, or a good leaving group (Br), efficiently generate QMs under physiological conditions. Finally, a quantitative relationship between the structure and activity has been established for the arylboronic esters by using a Hammett plot. The reactivity of the arylboronic acids/esters and the inhibition or facilitation of QM formation can now be predictably adjusted. This adjustment is important as some applications may benefit and others may be limited by QM generation. Tunable quinone methide formation: Aromatic substituents and the benzylic leaving group strongly affect the H 2O2-induced formation of quinone methides (QMs) from arylboronic esters (see scheme). The reactivity of arylboronic esters can be predictably adjusted by varying substituents. Copyright
