149682-75-7

Basic information

• Product Name: 2-Borono-1-pyrrolidinecarboxylicacid1-(1,1-dimethylethyl)ester
• Synonyms: (+/-)-1-(TERT-BUTOXYCARBONYL)PYRROLIDINE-2-BORONIC ACID;1-N-Boc-pyrrolidin-2-ylboronic acid;1-(Tert-butoxycarbonyl)pyrrolidin-2-ylboronic acid;1-(tert-butoxycarbonyl)pyrrolidin-2-yl-2-boronic acid;(N-(1,1-diMethylethoxycarbonyl)pyrrolidin-2-yl)boronic acid;N-Boc-pyrrolidin-2-yl]boronic Acid;1-pyrrolidinecarboxylic acid 2-broMo-1-(1,1-diMethylethyl)ester;1-N-Boc-pyrrolidin-2-ylboronic acid, 95+%
• CAS NO: 149682-75-7
• Molecular Formula: C₉H₁₈BNO₄
• Molecular Weight: 215.05452
• Product Categories: Chiral Compounds
• Mol File: 149682-75-7.mol

Chemical Properties

• Boiling Point: 349.226 °C at 760 mmHg
• Flash Point: 165.006 °C
• Appearance: /
• Density: 1.15 g/cm³
• Vapor Pressure: 2.89E-06mmHg at 25°C
• Refractive Index: 1.488
• Storage Temp.: Inert atmosphere,Store in freezer, under -20°C
• Solubility: Chloroform (Slightly, Heated), DMSO (Slightly)
• PKA: 9.94±0.20(Predicted)
• CAS DataBase Reference: 2-Borono-1-pyrrolidinecarboxylicacid1-(1,1-dimethylethyl)ester(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Borono-1-pyrrolidinecarboxylicacid1-(1,1-dimethylethyl)ester(149682-75-7)
• EPA Substance Registry System: 2-Borono-1-pyrrolidinecarboxylicacid1-(1,1-dimethylethyl)ester(149682-75-7)

Safety Data

• Hazardous Substances Data: 149682-75-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-Borono-1-pyrrolidinecarboxylic acid 1-(1,1-dimethylethyl)ester is used as a key intermediate in the synthesis of heterocyclic boronic acid compounds for pharmaceutical applications. Its unique structure allows for the development of novel drugs with potential therapeutic benefits, particularly in the treatment of various diseases and disorders.
Used in Chemical Research:
In the field of chemical research, 2-Borono-1-pyrrolidinecarboxylic acid 1-(1,1-dimethylethyl)ester serves as a valuable building block for the creation of complex organic molecules. Its reactivity and stability make it an ideal candidate for exploring new chemical reactions and developing innovative synthetic pathways.
Used in Material Science:
The unique properties of 2-Borono-1-pyrrolidinecarboxylic acid 1-(1,1-dimethylethyl)ester also make it a promising candidate for the development of new materials with specific properties. Its incorporation into polymers or other materials can lead to the creation of advanced materials with improved characteristics, such as enhanced stability, reactivity, or selectivity.

InChI:InChI=1/C9H18BNO4/c1-9(2,3)15-8(12)11-6-4-5-7(11)10(13)14/h7,13-14H,4-6H2,1-3H3

Upstream product

• 86953-79-9 tert-butyl pyrrolidine-1-carboxylate 
• 121-43-7 Trimethyl borate 
• 1333-74-0 hydrogen 
• 135884-31-0 N-boc-2-pyrroleboronic acid 
• 7732-18-5 water 

Downstream Products

• 138371-54-7 (±)-tert-butyl 2-(3-phenylpropanoyl)pyrrolidine-1-carboxylate 

Relevant articles and documents

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Amino terminus-blocked peptide boronate compounds of Formulas I and II are useful for inhibiting Fibroblast Activation Protein (FAP) and other proteases, and for treating disorders mediated by FAP. Methods of using the amino terminus blocked peptide boronate compounds, and stereoisomers, tautomers, solvates and pharmaceutically acceptable salts thereof, for in vitro, in situ, and in vivo diagnosis, prevention or treatment of such disorders in mammalian cells, or associated pathological conditions are disclosed.

HETEROCYCLIC BORONIC ACID COMPOUNDS

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Direct selection for catalysis from combinatorial antibody libraires using a boronic acid probe: Primary amide bond hydrolysis

This report describes a joint hybridoma and combinatorial antibody library approach to elicit catalysts for primary amide bond hydrolysis. By immunization with a trigonal boronic acid hapten 3a and construction of a Fab (antigen-binding fragment) library, a diastereoselective catalyst for hydrolysis of the tripeptide primary amide substrate la was selected. In contrast, no antibody catalyst was isolated by standard hybridoma methods of monoclonal antibody production following immunizations with hapten 3a. The active Fab, BL25, obeys Michaelis-Menten kinetic behavior (k(cat)/k(uncat) ca. 4 x 104, K(m) = 150 μM) and is competitively inhibited by a boronic acid hapten analog 3b (K(i) = 9 μM). Kinetic and binding studies both point to Fab selection of a hydrated tetrahedral anionic form of the boronic acid hapten 3a which serves to mimic the putative transition state 4 for catalysis of water addition to the primary amide bond. Fab-BL25 exhibits exquisite substrate selectivity, as a methyl ester analog of 1a is not accepted as a substrate. This work emphasises the power of the direct selection strategy when linked to screening of antibody combinatorial libraries and discloses the utility of boronic acids as haptens in acyl transfer processes.