56842-95-6

Basic information

• Product Name: Bicyclo[1.1.1]pentane-1,3-dicarboxylic acid
• Synonyms: Bicyclo[1.1.1]pentane-1,3-dicarboxylic acid;1,3-Bicyclo[1.1.1]pentanedicarboxylic acid
• CAS NO: 56842-95-6
• Molecular Formula: C₇H₈O₄
• Molecular Weight: 156.13602
• Mol File: 56842-95-6.mol
• Article Data: 14

Chemical Properties

• Melting Point: 260 °C (sublm)
• Boiling Point: 205.3±20.0 °C(Predicted)
• Appearance: /
• Density: 1.864±0.06 g/cm3(Predicted)
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 4.23±0.40(Predicted)
• CAS DataBase Reference: Bicyclo[1.1.1]pentane-1,3-dicarboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: Bicyclo[1.1.1]pentane-1,3-dicarboxylic acid(56842-95-6)
• EPA Substance Registry System: Bicyclo[1.1.1]pentane-1,3-dicarboxylic acid(56842-95-6)

Safety Data

• Hazardous Substances Data: 56842-95-6(Hazardous Substances Data)

Usage

Description

Bicyclo[1.1.1]pentane-1,3-dicarboxylic acid is an organic compound featuring a bicyclic structure with two carboxylic acid functional groups. It is known for its unique molecular geometry and reactivity, making it a versatile building block in various chemical applications.

Uses

Used in Polymer Synthesis:
Bicyclo[1.1.1]pentane-1,3-dicarboxylic acid is used as a monomer for the production of polymers, specifically in the synthesis of high-performance materials with unique mechanical and thermal properties. Its bicyclic structure contributes to the stability and rigidity of the resulting polymers.
Used in Click Chemistry:
Bicyclo[1.1.1]pentane-1,3-dicarboxylic acid serves as a useful reagent in click chemistry, a set of powerful and versatile reactions that rapidly form new chemical bonds. Its carboxylic acid groups facilitate the formation of stable and selective products, making it a valuable component in the synthesis of complex molecular structures.
Used in Biological Studies:
Bicyclo[1.1.1]pentane-1,3-dicarboxylic acid is also utilized in biological research as a starting material for the development of novel bioactive compounds. Its unique structure allows for the creation of new molecules with potential applications in drug discovery and the study of biological processes.

Upstream product

• 65862-02-4 2,2-Dichloro-bicyclo[1.1.1]pentane-1,3-dicarboxylic acid monomethyl ester 
• 124-38-9 carbon dioxide 
• 35634-10-7 [1.1.1]propellane 
• 105542-93-6 1-(1-hydroxyethyl)-3-(1-oxoethyl)bicyclo<1.1.1>pentane 
• 115913-30-9 1,1′-(bicyclo[1.1.1]pentane-1,3-diyl)bis(ethan-1-one) 
• 83249-10-9 3‐(methoxycarbonyl)bicyclo[1.1.1]pentane‐1‐carboxylic acid 
• 134-81-6 benzil 
• 311-75-1 bicyclo[1.1.1]pentane 
• 65862-03-5 methyl 3-phenyl-2,2-dichlorobicyclo<1.1.1>pentanecarboxylate 
• 83249-09-6 methyl 3-phenylbicyclo<1.1.1>pentane-1-carboxylate 
• 83249-04-1 3-phenylbicyclo<1.1.1>pentane-1-carboxylic acid 
• 290-37-9 1,4-pyrazine 
• 431-03-8 dimethylglyoxal 
• 115913-32-1 dimethyl bicyclo<1.1.1>pentane-1,3-dicarboxylate 

Downstream Products

• 115913-32-1 dimethyl bicyclo<1.1.1>pentane-1,3-dicarboxylate 
• 82783-71-9 1,3 dibromobicyclo[1.1.1]pentane 
• 115913-31-0 1,3-bis(chlorocarbonyl)bicyclo<1.1.1>pentane 
• 82783-71-9 1,3-dibromobicyclo<1.1.1>pentane 
• 83249-10-9 3‐(methoxycarbonyl)bicyclo[1.1.1]pentane‐1‐carboxylic acid 
• 156329-62-3 3-(hydroxymethyl)bicyclo[1.1.1]pentane-1-carbonitrile 
• 180464-87-3 methyl 3-(hydroxylmethyl)bicyclo[1.1.1]pentane-1-carboxylate 
• 180464-92-0 3-formylbicyclo[1.1.1]pentane-1-carboxylic acid methyl ester 
• 180465-00-3 3-[(R)-Cyano-((R)-2-hydroxy-1-phenyl-ethylamino)-methyl]-bicyclo[1.1.1]pentane-1-carboxylic acid methyl ester 
• 180464-96-4 3-[(S)-Cyano-((R)-2-hydroxy-1-phenyl-ethylamino)-methyl]-bicyclo[1.1.1]pentane-1-carboxylic acid methyl ester 
• 1370705-39-7 3-(hydroxymethyl)bicyclo[1.1.1]pentane-1-carbonitrile 
• 1370705-40-0 (R)-2-{4-chloro-N-[(3-cyanobicyclo[1.1.1]pentan-1-yl)methyl]phenylsulfonamide}-5,5,5-trifluoropentanamide 
• 1370705-38-6 (R)-2-{N-{[3-(1,2,4-oxadiazol-3-yl)bicyclo[1.1.1]pentan-1-yl]-methyl}-4-chlorophenylsulfonamido}-5,5,5-trifluoropentanamide 
• 146038-53-1 3-fluorobicyclo<1.1.1>pentane-1-carboxylic acid 

Relevant articles and documents

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Bicyclo[1.1.1]pentane-Derived Building Blocks for Click Chemistry

Syntheses of bicyclo[1.1.1]pentane-derived azides and terminal alkynes – interesting substrates for click reactions – are described. With a few exceptions, these compounds were prepared in two or three steps starting from common synthetic intermediates – the corresponding carboxylic acids. The key step in the synthesis of 1-azidobicyclo[1.1.1]pentanes is a copper-catalysed diazo-transfer reaction with imidazole-1-sulfonyl azide. The preparation of bicyclo[1.1.1]pentyl-substituted alkynes relies on a Seyferth–Gilbert homologation with dimethyl 1-diazo-2-oxopropylphosphonate (Ohira–Bestmann reagent). Both types of target compounds were found to be suitable substrates for click reactions, and thus they are promising building blocks for medicinal, combinatorial and bioconjugate chemistry. A practically important side result of this study was a multigram preparation of Boc-monoprotected 1,3-diaminobicyclo[1.1.1]pentane – a representative bicyclic conformationally restricted diamine derivative.

Design, Synthesis, and Application of an Optimized Monofluorinated Aliphatic Label for Peptide Studies by Solid-State19F NMR Spectroscopy

A conformationally restricted monofluorinated α-amino acid, (3-fluorobicyclo[1.1.1]pentyl)glycine (F-Bpg), was designed as a label for the structural analysis of membrane-bound peptides by solid-state19F NMR spectroscopy. The compound was synthesized and validated as a19F label for replacing natural aliphatic α-amino acids. Calculations suggested that F-Bpg is similar to Leu/Ile in terms of size and lipophilicity. The19F NMR label was incorporated into the membrane-active antimicrobial peptide PGLa and provided information on the structure of the peptide in a lipid bilayer.