191171-55-8 Usage
Description
2-Aminophenylboronic acid pinacol ester is an organic compound that serves as an important building block in the synthesis of various complex organic molecules. It is a cream-colored crystalline powder, which is a valuable reactant in the chemical industry due to its unique reactivity and functional groups.
Uses
Used in Pharmaceutical Industry:
2-Aminophenylboronic acid pinacol ester is used as a reactant for the synthesis of various pharmaceutical compounds, such as Indolo[3,4-cd]benzazepines, which are known for their potential applications in the treatment of various diseases. It is used for the synthesis of these compounds through Pictet-Spengler-type cyclizations, a widely employed method in organic chemistry for the formation of heterocyclic compounds.
Used in Antimicrobial Applications:
In the field of antimicrobial research, 2-Aminophenylboronic acid pinacol ester is used as a reactant for the synthesis of antimicrobial amphiphilic aryl peptideomimetics. These compounds have shown potential in combating drug-resistant bacteria and other pathogens, making them an important area of study in the development of new antimicrobial agents.
Used in Chemical Synthesis:
2-Aminophenylboronic acid pinacol ester is also used as a reactant in the synthesis of various other organic compounds, such as Pyridoquinazolines, benzo[h]naphthyridines, thienopyridine derivatives, dihydroquinolones, and methacrylamidophenylboronic acids. These compounds have diverse applications in the chemical industry, ranging from pharmaceuticals to materials science.
Overall, 2-Aminophenylboronic acid pinacol ester is a versatile and valuable compound in the fields of pharmaceuticals, antimicrobial research, and chemical synthesis, playing a crucial role in the development of new and innovative products.
Reactions
2-Aminophenylboronic acid pinacol ester is a reactant involved in synthesis of:
??Indolo[3,4-cd] benzazepines via Pictet-Spengler-type cyclizations
??Antimicrobial amphiphilic aryl peptideomimetics
??Pyridoquinazolines and benzo[h]naphthyridines via intramolecular electrophilic substitution reactions
??Thienopyridine derivatives
??Dihydroquinolones
??Methacrylamidophenylboronic acids
Check Digit Verification of cas no
The CAS Registry Mumber 191171-55-8 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,9,1,1,7 and 1 respectively; the second part has 2 digits, 5 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 191171-55:
(8*1)+(7*9)+(6*1)+(5*1)+(4*7)+(3*1)+(2*5)+(1*5)=128
128 % 10 = 8
So 191171-55-8 is a valid CAS Registry Number.
InChI:InChI=1/C12H18BNO2/c1-11(2)12(3,4)16-13(15-11)9-7-5-6-8-10(9)14/h5-8H,14H2,1-4H3
191171-55-8Relevant articles and documents
Self-activation and 1,8-stereoinduction in a boronate-substituted dienophile
Kennedy, Jason W. J.,Hall, Dennis G.
, p. 477 - 479 (2002)
The [4+2] cycloaddition of ortho-boronoanilide dienophile 4 with cyclopentadiene was found to proceed faster than both its para isomer 8 and the unsubstituted derivative 6, thereby confirming that self-activation by internal coordination is operative in the case of 4. Chiral boronic esters derivatives 9 and 10 provided a small level of remote 1,8-stereoinduction. These results show that dialkoxyboronic esters can operate as weak, internal Lewis acids and activate carbonyl-containing functionalities in cycloaddition reactions.
1,3,5-Tris(2′-aminophenyl)benzene: A novel platform for molecular receptors
Pia?tek, Piotr,S?omiany, Norbert
, p. 2027 - 2030 (2006)
The synthesis of a novel, rigid, aromatic platform for molecular receptors is described. 1,3,5-Tris(2′-aminophenyl)benzene was prepared via Suzuki-Miyaura cross-coupling reactions of 2-aminophenylboronic acid with 1,3,5-triiodobenzene in the presence of Ba(OH)2, Pd(OAc)2 and (2-biphenyl)dicyclohexylphosphine. Alternatively, one-pot borylation of 2-bromoaniline and cross-coupling of the resulting boronate ester with 1,3,5-triiodobenzene was investigated. Georg Thieme Verlag Stuttgart.
Recyclable Pd2dba3/XPhos/PEG-2000 System for Efficient Borylation of Aryl Chlorides: Practical Access to Aryl Boronates
Cai, Mingzhong,Huang, Bin,Luo, Chengkai,Xu, Caifeng
, (2021/12/02)
Pd2dba3/XPhos in poly(ethylene glycol) (PEG-2000) is shown to be a highly stable and efficient catalyst for the borylation of aryl chlorides with bis(pinacolato)diboron. The borylation reaction proceeds smoothly at 110 °C, delivering a wide variety of aryl boronates in good to excellent yields with high functional group tolerance. The crude products were easily isolated via simple extraction of the reaction mixture with cyclohexane. Moreover, both expensive Pd2dba3 and XPhos in PEG-2000 system could be readily recycled and reused more than six times without loss of catalytic efficiency.
Ruthenium-catalyzed regio- And site-selective: Ortho C-H borylation of phenol derivatives
Homma, Yuki,Fukuda, Kazuishi,Iwasawa, Nobuharu,Takaya, Jun
supporting information, p. 10710 - 10713 (2020/10/02)
Efficient synthesis of o-borylphenols is achieved through the Ru-catalyzed regio- and site-selective sp2 C-H borylation of aryl diphenylphosphinites followed by removal of the phosphorus directing group. A successful application to aryl phosphites enables practical one-pot borylation of phenols, demonstrating high synthetic utility of this protocol.