3-(Methoxycarbonyl)bicyclo[1.1.1]pentane-1-carboxylic acid

Name: 3-(Methoxycarbonyl)bicyclo[1.1.1]pentane-1-carboxylic acid
Brand: ChemScene
Availability: InStock
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CAS No. 83249-10-9
Cat. No. CS-W001056
Purity≥98%
MDL No.MFCD20638314

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3-(Methoxycarbonyl)bicyclo[1.1.1]pentane-1-carboxylic acid|CS-W001056

Structure of 83249-10-9

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General Information

CAS No. 83249-10-9
Cat. No. CS-W001056
Purity ≥98%
MDL No. MFCD20638314
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₈H₁₀O₄
Molecular Weight 170.16
Synonym(s) None
SMILES O=C(O)C12CC(C(=O)OC)(C1)C2

Description

D-Isosorbide is used as a reagent in the preparation of detergents, agrochemicals, cleansers, cosmetics and vasodilators. It is also employed as a pharmaceutical intermediate for dimethyl ether and mono- and dinitrate derivatives, which is used as vasodilators and coronary disease therapeutics. It is used in the treatment of hydrocephalus and glaucoma. It finds application as a building block for polymers like polycarbonates and polyesters.

Application

3-(Methoxycarbonyl)bicyclo[1.1.1]pentane-1-carboxylic acid serves as a rigid, sterically constrained building block for medicinal chemistry and synthetic methodology development. Its bicyclic core imparts high conformational stability, while the flanking ester and carboxylic acid groups enable versatile functionalization via standard transformations. The molecule exhibits excellent bench stability and facilitates efficient purification, making it well-suited for use in coupling reactions, heterocycle synthesis, and scaffold diversification within robust synthetic workflows.

Synthesis

Route1
- 83249-09-6
- ~63%
- In-stock
  
  83249-10-9
References
- Applequist, Douglas E.; Renken, Terry L.; Wheeler, James W. Journal of Organic Chemistry, 1982 , vol. 47, # 25 p. 4985 - 4995
Route2
- 311-75-1
- ~%
- In-stock
  
  83249-10-9
References
- Pellicciari; Raimondo; Marinozzi; Natalini; Costantino; Thomsen Journal of Medicinal Chemistry, 1996 , vol. 39, # 15 p. 2874 - 2876
Route3
- 105542-93-6
- ~%
- In-stock
  
  83249-10-9
References
- Kaszynski, Piotr; Michl, Josef Journal of Organic Chemistry, 1988 , vol. 53, # 19 p. 4593 - 4594

Safety Information

Download SDS

GHS Pictogram :	GHS No : GHS06
Signal Word : Danger	UN#: 2811
Class : 6.1	Packing Group : Ⅲ
Hazard Statements : H301
Precautionary Statements : P301+P330+P331

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Computational Chemistry Data

TPSA 63.6
LogP 0.4143
H_Acceptors 3
H_Donors 1
Rotatable_Bonds 2

Other Classifications

Building Blocks Functional Group Ester

Building Blocks Skeleton Bridge Rings compounds Other bridge ring compounds

Building Blocks Skeleton Fatty ring compounds Cyclobutane compounds

Chemical Biology Pharmaceutical Development and Drug Discovery Research Reagents Specialized Building Blocks for Drug Discovery Bicyclo[1.1.1]pentane Building Blocks

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3-(Methoxycarbonyl)bicyclo[1.1.1]pentane-1-carboxylic acid

CAS No. 83249-10-9

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