| Identification | Back Directory | [Name]
Bicyclo[1.1.1]pentane-1,3-dicarboxylic acid | [CAS]
56842-95-6 | [Synonyms]
o[1.1.1]pentane-1,3-dicarboxyL
1,3-Bicyclo[1.1.1]pentanedicarboxylic acid
Bicyclo[1.1.1]pentane-1,3-dicarboxylic acid
1,1'-Bicyclo[1,1,1]pentane-1,3-dicarboxylic acid | [Molecular Formula]
C7H8O4 | [MDL Number]
MFCD20621127 | [MOL File]
56842-95-6.mol | [Molecular Weight]
156.14 |
| Chemical Properties | Back Directory | [Melting point ]
260 °C (sublm) | [Boiling point ]
205.3±20.0 °C(Predicted) | [density ]
1.864±0.06 g/cm3(Predicted) | [storage temp. ]
Sealed in dry,Room Temperature | [form ]
solid | [pka]
4.23±0.40(Predicted) | [color ]
White to off-white | [InChI]
InChI=1S/C7H8O4/c8-4(9)6-1-7(2-6,3-6)5(10)11/h1-3H2,(H,8,9)(H,10,11) | [InChIKey]
SBLRPOGZAJTJEG-UHFFFAOYSA-N | [SMILES]
C12(C(O)=O)CC(C(O)=O)(C1)C2 |
| Hazard Information | Back Directory | [Chemical Properties]
Bicyclo[1.1.1]pentane-1,3-dicarboxylic acid is a white to off-white solid at room temperature and pressure. It exhibits significant acidity and poor chemical stability. It is poorly soluble in water and low-polarity organic solvents, but exhibits some solubility in highly polar organic solvents. The compound contains two carboxylic acid units and possesses the common physical and chemical properties of alkyl carboxylic acids. It can undergo chlorination with thionyl chloride to yield the corresponding acyl chloride derivatives, and can also undergo condensation with alcohols in the presence of condensing agents to yield the corresponding ester derivatives. Furthermore, literature reports indicate that bicyclo[1.1.1]pentane-1,3-dicarboxylic acid can undergo decarboxylative fluorination with fluorination reagents, making it a promising candidate for the synthesis of fluorinated bicyclo[1.1.1]pentane derivatives. | [Uses]
Bicyclo[1.1.1]pentane-1,3-dicarboxylic Acid is a starting material for polymers. A useful reagent for click chemistry and biological studies. | [Synthesis]
The general procedure for the synthesis of bicyclo[1.1.1]pentane-1,3-dicarboxylic acid using 1,1'-(bicyclo[1.1.1]pentane-1,3-diyl)diethyl ketone as a starting material was as follows: compound 4 (23 g) was dissolved in dioxane (100 mL), followed by a slow, titrational addition to a sodium hypochlorite solution (1 L) over a temperature range of 10 °C to 15 °C. The reaction mixture was stirred continuously at this temperature for 4 hours. Upon completion of the reaction, sodium thiosulfate (6 g) was added to quench the reaction. The reaction solution was washed with chloroform (400mL x 3). The aqueous phase was acidified with concentrated hydrochloric acid to pH less than 1, followed by extraction with ethyl acetate (500 mL × 3). All ethyl acetate extracts were combined, washed with saturated brine and dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated to give compound 5 (11.5 g) in 50% yield. | [References]
[1] Journal of Organic Chemistry, 1988, vol. 53, # 19, p. 4593 - 4594
[2] European Journal of Organic Chemistry, 2017, vol. 2017, # 43, p. 6450 - 6456
[3] Journal of Medicinal Chemistry, 2012, vol. 55, # 7, p. 3414 - 3424
[4] Patent: CN105294442, 2016, A. Location in patent: Paragraph 0006; 0011
[5] Journal of Medicinal Chemistry, 1996, vol. 39, # 15, p. 2874 - 2876 |
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