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

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

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

• 35634-10-7 [1.1.1]propellane 
• 134-81-6 benzil 
• 431-03-8 dimethylglyoxal 
• 115913-32-1 dimethyl bicyclo<1.1.1>pentane-1,3-dicarboxylate 
• 98577-44-7 1,1-bis(chloromethyl)-2,2-dibromocyclopropane 
• 65862-03-5 methyl 3-phenyl-2,2-dichlorobicyclo<1.1.1>pentane-1-carboxylic acid 
• 83249-09-6 methyl 3-phenylbicyclo<1.1.1>pentane-1-carboxylate 
• 30493-96-0 methyl 3-phenylbicyclo<1.1.0>butane-1-carboxylate 
• 36126-39-3 methyl 3-bromo-3-phenylcyclobutane-1-carboxylate 
• 227935-29-7 methyl 3-phenylcyclobutane-1-carboxylate 
• 83249-04-1 3-phenylbicyclo<1.1.1>pentane-1-carboxylic acid 
• 290-37-9 1,4-pyrazine 
• 83249-04-1 3-phenylbicyclo<1.1.1>pentane-1-carboxylic acid 
• 83249-09-6 methyl 3-phenylbicyclo<1.1.1>pentane-1-carboxylate 

Downstream Products

• 82783-71-9 1,3 dibromobicyclo[1.1.1]pentane 
• 115913-31-0 1,3-bis(chlorocarbonyl)bicyclo<1.1.1>pentane 
• 146038-53-1 3-fluorobicyclo<1.1.1>pentane-1-carboxylic acid 
• 115913-32-1 dimethyl bicyclo<1.1.1>pentane-1,3-dicarboxylate 
• 676371-64-5 3-((tert-butoxycarbonyl)amino)bicyclo[1.1.1]pentane-1-carboxylic acid methyl ester 
• 262852-01-7 (3-fluorobicyclo[1.1.1]pentane-1-yl)methanol 
• 303752-38-7 3-((tert-butoxycarbonyl)amino)bicyclo[1.1.1]pentane-1-carboxylic acid 
• 82783-71-9 1,3-dibromobicyclo<1.1.1>pentane 
• 262852-00-6 1-(3-fluoro-1-bicyclo[1.1.1]pentanyl)ethanone 
• 83249-10-9 3‐(methoxycarbonyl)bicyclo[1.1.1]pentane‐1‐carboxylic acid 

Relevant articles and documents

Large-Scale Synthesis and Modifications of Bicyclo[1.1.1]pentane-1,3-dicarboxylic Acid (BCP)

In flow photochemical addition of propellane to diacetyl allowed construction of the bicyclo[1.1.1]pentane (BCP) core in a 1 kg scale within 1 day. Haloform reaction of the formed diketone in batch afforded bicyclo[1.1.1]pentane-1,3-dicarboxylic acid in a

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.

Preparation method for bicyclo [1.1.1] pentane-1,3-dicarboxylic acid dimethylester

The invention relates to a preparation method for bicyclo [1.1.1] pentane-1,3-dicarboxylic acid dimethylester, and mainly solves the technical problem that a method suitable for industrial synthesis does not exist at present. The preparation method comprises the following six steps: firstly, reacting a compound (1) and bromoform under an alkaline condition to obtain a compound (2); secondly, reacting the compound (2) and lithium methide to obtain a compound (3); thirdly, illuminating the compound (3) and diacetyl by a high-pressure mercury lamp to obtain a compound (4); fourthly, treating with sodium hypochlorite to obtain a compound (5); fifthly, reacting the compound (5) and thionyl chloride to obtain a compound (6); and finally, treating the compound (6) under the effect of methanol to obtain a compound (7) which is a final product. A reaction formula is as shown in the specification, and the acquired bicyclo [1.1.1] pentane-1,3-dicarboxylic acid dimethylester is a useful midbody or product for synthesis of many drugs.

A practical metal-free homolytic aromatic alkylation protocol for the synthesis of 3-(pyrazin-2-yl)bicyclo[1.1.1]pentane-1-carboxylic acid

As a part of our ongoing synthetic quest to expand the frontiers of contemporary medicinal chemistry, we now report an expedient synthesis of a potentially useful bicyclo[1.1.1]pentane building block, 3-(pyrazin-2-yl)bicyclo[1.1.1]pentane-1-carboxylic acid. This report also showcases the application of this motif as a probe in a biological study.

Application of the bicyclo[1.1.1]pentane motif as a nonclassical phenyl ring bioisostere in the design of a potent and orally active γ-secretase inhibitor

Replacement of the central, para-substituted fluorophenyl ring in the γ-secretase inhibitor 1 (BMS-708,163) withthe bicyclo[1.1.1]pentane motif led to the discovery of compound 3, an equipotent enzyme inhibitor with significant improvements in passive permeability and aqueous solubility. The modified biopharmaceutical properties of 3 translated into excellent oral absorption characteristics (～4-fold Cmax and AUC values relative to 1) in a mouse model of γ-secretase inhibition. In addition, SAR studies into other fluorophenyl replacements indicate the intrinsic advantages of the bicyclo[1.1.1]pentane moiety over conventional phenyl ring replacements with respect to achieving an optimal balance of properties (e.g., γ-secretase inhibition, aqueous solubility/permeability, in vitro metabolic stability). Overall, this work enhances the scope of the [1.1.1]-bicycle beyond that of a mere spacer unit and presents a compelling case for its broader application as a phenyl group replacement in scenarios where the aromatic ring count impacts physicochemical parameters and overall drug-likeness.

Compounds and methods based on [1.1.1]propellane

Molecular bulding beams, liquid crystals, and surfactants in the form of compounds based on [1.1.1]propellane, including poly[1.1.1]propellanes. Molecular building beams having a telomeric or polymeric chain staff, and linking groups functionalized on one or both ends of the staff. A system for linking the beams to connecting units to construct molecular structures of various forms, such as whips, combs, scaffoldings, nets, or stars. Other broad aspects of the invention provide liquid crystals and surfactants. The liquid crystals include telomeric or polymeric compounds functionalized with flexible end groups, while the surfactant compounds are functionalized with surface active end groups. Methods of synthesizing the various compounds ar also provided.

Toward a molecular-size "Tinkertoy" construction set. Preparation of terminally functionalized [n]staffanes from [1.1.1]propellane

A facile but low-yield synthesis of [n]staffanes (the oligomers of [1.1.1.]propellane 1, n =1-5) functionalized on one or both ends is described, and their properties are summarized. The substituents are -COOCH3, -n-C4H9, -C6H5, -Br, -I, and -SCOCH3, and their conversion to others, such as -COOH, -COCH3 and -SH, is demonstrated. It is proposed that these rod-shaped molecules will be useful in the development of a molecular-size civil engineering construction set analogous to children's toy construction sets.