834-50-4

Basic information

• Product Name: Bicyclo[2.2.2]octane-1,4-dicarboxylic acid, Monoethyl ester
• Synonyms: Bicyclo[2.2.2]octane-1,4-dicarboxylic acid, Monoethyl ester;1-Ethoxycarbonylbicyclo[2.2.2]octane-4-carboxylic acid;4-(Ethoxycarbonyl)bicyclo-[2.2.2]octane-1-carboxylic acid;Bicyclo[2.2.2]octane-1,4-dicarboxylic acid 1-ethyl ester;NSC 177416
• CAS NO: 834-50-4
• Molecular Formula: C₁₂H₁₈O₄
• Molecular Weight: 226.26892
• Mol File: 834-50-4.mol

Chemical Properties

• Boiling Point: 336.8 °C at 760 mmHg
• Flash Point: 125.2 °C
• Appearance: /
• Density: 1.265g/cm³
• Vapor Pressure: 2.06E-05mmHg at 25°C
• Refractive Index: 1.543
• CAS DataBase Reference: Bicyclo[2.2.2]octane-1,4-dicarboxylic acid, Monoethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Bicyclo[2.2.2]octane-1,4-dicarboxylic acid, Monoethyl ester(834-50-4)
• EPA Substance Registry System: Bicyclo[2.2.2]octane-1,4-dicarboxylic acid, Monoethyl ester(834-50-4)

Safety Data

• Hazardous Substances Data: 834-50-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Bicyclo[2.2.2]octane-1,4-dicarboxylic acid, Monoethyl ester is used as a key intermediate in the synthesis of various pharmaceuticals for its unique bicyclic structure and reactivity, contributing to the development of novel drugs with improved therapeutic properties.
Used in Agrochemical Industry:
In the agrochemical sector, Bicyclo[2.2.2]octane-1,4-dicarboxylic acid, Monoethyl ester is utilized as a precursor in the production of agrochemicals, such as pesticides and herbicides, due to its ability to enhance the effectiveness and selectivity of these compounds.
Used in Advanced Materials:
Bicyclo[2.2.2]octane-1,4-dicarboxylic acid, Monoethyl ester is employed as a building block in the development of advanced materials, including polymers and composites, leveraging its unique structural features to impart desirable properties such as enhanced stability, strength, and functionality.
Overall, Bicyclo[2.2.2]octane-1,4-dicarboxylic acid, Monoethyl ester is a multifaceted chemical compound with a broad spectrum of applications across different industries, making it an essential component in the field of organic synthesis and product manufacturing.

InChI:InChI=1/C12H18O4/c1-2-16-10(15)12-6-3-11(4-7-12,5-8-12)9(13)14/h2-8H2,1H3,(H,13,14)

Upstream product

• 1659-75-2 Bicyclo<2.2.2.>octan-1,4-dicarbonsauere-ethylester 
• 787-07-5 diethyl 1,4-cyclohexanedione-2,5-dicarboxylate 
• 1686-98-2 2,5-Bis-ethylendimercapto-bicyclo<2,2,2>octan-1,4-dicarbonsaeure-diethylester 
• 843-59-4 Diethyl 2,5-Dioxobicyclo<2.2.2>octane-1,4-dicarboxylate 
• 41034-55-3 (+/-)-dispiro[[1,3]dithiane-2,2'-bicyclo[2.2.2]octane-5',2''-[1,3]dithiane]-1',4'-dicarboxylic acid diethyl ester 

Downstream Products

• 79663-72-2 ethyl 1-(aminocarbonyl)bicyclo<2.2.2>octane-4-carboxylate 
• 1299425-88-9 ethyl 4-iodobicyclo[2.2.2]octane-1-carboxylate 
• 905457-33-2 4-iodo-N-(2-(4-(2-methoxyphenyl)piperazin-1-yl)ethyl)-N-(pyridin-2-yl)bicyclo[ 2.2.2]octane-1-carboxamide 
• 1299426-08-6 4-iodo-N-(2-(4-(2-hydroxyphenyl)piperazin-1-yl)ethyl)-N-(pyridin-2-yl)bicyclo[ 2.2.2]octane-1-carboxamide 
• 80745-61-5 4-iodobicyclo<2.2.2>octane-1-carboxylic acid 
• 2346-09-0 ethyl 4-(hydroxymethyl)bicyclo[2.2.2]octane-1-carboxylate 
• 1350822-02-4 ethyl 4-(iodomethyl)bicyclo[2.2.2]octane-1-carboxylate 
• 54829-94-6 4-cyano-bicyclo[2.2.2]octane-1-carboxylic acid ethyl ester 
• 13595-17-0 4-amino-bicyclo[2.2.2]octane-1-carboxylic acid 
• 788-71-6 4-ethoxycarbonylamino-bicyclo[2.2.2]octane-1-carboxylic acid ethyl ester 
• 15941-09-0 4-cyanobicyclo<2.2.2>octane-1-carboxylic acid 
• 444344-94-9 N-[4-[[(2,4-diamino-6-pteridinyl)methyl]amino]bicyclo[2.2.2]octane-1-carbonyl]-L-glutamic acid dimethyl ester 
• 444344-92-7 N-[4-[[(benzyloxy)carbonyl]amino]bicyclo[2.2.2]octane-1-carbonyl]-L-glutamic acid dimethyl ester 
• 444344-93-8 N-(4-aminobicyclo[2.2.2]octane-1-carbonyl)-L-glutamic acid dimethyl ester 

Relevant articles and documents

Design, synthesis, radiolabeling, and in vitro and in vivo evaluation of bridgehead iodinated analogues of N -{2-[4-(2-methoxyphenyl)piperazin-1-yl] ethyl}- N -(pyridin-2-yl)cyclohexanecarboxamide (WAY-100635) as potential SPECT ligands for the 5-HT1A receptor

Here we describe the design, synthesis, and pharmacological profile of 5-HT1A receptor ligands related to 1 (WAY-100635). The cyclohexyl moiety in 1 and its O-desmethylated analogue 3 were replaced by the bridgehead iodinated bridge-fused rings: adamantyl, cubyl, bicyclo[2.2.2]octyl, or bicyclo[2.2.1]heptyl. All analogues displayed a (sub)nanomolar affinity for the 5-HT1A receptor in vitro. Compounds 6b and 7b appeared to be selective for this receptor over other relevant receptors and could easily be iodinated with radioactive iodine-123. In humane hepatocytes, [ 123I]6b showed a low propensity for amide hydrolysis and a stable carbon-iodine bond. The biodistribution of [123I]6b and [ 123I]7b in rats revealed that the carbon-iodine bond was also stable in vivo. Unfortunately, the brain uptake and the specificity for both radioligands were significantly lower than those of the parent molecule 1. In conclusion, the designed tracers are not suitable for SPECT imaging.