Bicyclo[1.1.1]pentane-1,3-dicarboxylic acid, MonoMethyl ester Chemical Properties

Melting point:

138-139 °C(Solv: chloroform (67-66-3); heptane (142-82-5))

Boiling point:

272.2±40.0 °C(Predicted)

Density 

1.559±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

form 

powder to crystal

pka

4.50±0.40(Predicted)

color 

White to Orange to Green

InChI

InChI=1S/C8H10O4/c1-12-6(11)8-2-7(3-8,4-8)5(9)10/h2-4H2,1H3,(H,9,10)

InChIKey

UJZHYIMESNWEQA-UHFFFAOYSA-N

SMILES

C12(C(OC)=O)CC(C(O)=O)(C1)C2

Safety Information

RIDADR 

UN2811

HS Code 

2917198090

Bicyclo[1.1.1]pentane-1,3-dicarboxylic acid, MonoMethyl ester Usage And Synthesis

Uses

Bicyclo[1.1.1]pentane-1,3-dicarboxylic Acid, 1-methyl Ester acts as a reagent for the synthesis and in the biopharmaceutical evaluation of imatinib analogs. Also functions as a reagent for the preparation and in biological evaluation of novel bicyclo[1.1.1]pentane-based acidic amino acids as glutamate receptors ligands It is a COVID19-related research product.

Synthesis

The general procedure for the synthesis of methyl bicyclo[1.1.1]pentane-1-carboxylate-3-carboxylate from oxalyl chloride monomethyl ester and the compound (CAS:35634-10-7) was as follows: first, a solution of [1.1.1]propeller in Et2O (500 mL; 161 mmol, 1 eq.) was prepared independently, along with ethyl chloroacetate (16.3 mL, 177 mmol, 1.1 eq.) solution in Et2O (49.7 mL). The entire reactor was flushed for 5 min using pure Et2O (pump 1: 4.0 mL/min, pump 2: 0.5 mL/min). Subsequently, a solution of reagent (2) was injected at a flow rate of 4.0 mL/min at 0 to -80 °C, followed by a solution of reagent (3) at a flow rate of 0.5 mL/min at room temperature. The photoreactor was placed in an ice bath (volume 58 mL; FEP tube rotated over a lamp). After the reaction mixture left the photoreactor, it was quenched using an alkaline aqueous solution of NaOH, KOH, NaHCO3, or KHCO3. After vigorous stirring for 2 h, the aqueous layer was separated and acidified to pH = 1. Subsequently, the mixture was extracted with DCM (3 × 500 mL). The combined organic layers were dried over MgSO4, filtered and concentrated under reduced pressure to afford 3-(methoxycarbonyl)bicyclo[1.1.1]pentane-1-carboxylic acid (9, 17.5 g, 103 mmol, 63% yield), the product being a pale yellow solid.

References

[1] Patent: WO2017/157932, 2017, A1. Location in patent: Page/Page column 27

Bicyclo[1.1.1]pentane-1,3-dicarboxylic acid, MonoMethyl ester(83249-10-9)Related Product Information

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