53343-60-5

Basic information

• Product Name: 1,3,5-Cycloheptatriene-1-carboxylicacid,methylester(6CI,9CI)
• Synonyms: 1,3,5-Cycloheptatriene-1-carboxylicacid,methylester(6CI,9CI)
• CAS NO: 53343-60-5
• Molecular Formula: C₉H₁₀O₂
• Molecular Weight: 150.1745
• Product Categories: CARBOXYLICESTER
• Mol File: 53343-60-5.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 106-107 °C(Press: 16 Torr)
• Appearance: /
• Density: 1.075±0.06 g/cm3(Predicted)
• CAS DataBase Reference: 1,3,5-Cycloheptatriene-1-carboxylicacid,methylester(6CI,9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3,5-Cycloheptatriene-1-carboxylicacid,methylester(6CI,9CI)(53343-60-5)
• EPA Substance Registry System: 1,3,5-Cycloheptatriene-1-carboxylicacid,methylester(6CI,9CI)(53343-60-5)

Safety Data

• Hazardous Substances Data: 53343-60-5(Hazardous Substances Data)

Usage

Functional groups

Ester, Carboxylic Acid

Structure

Cyclic with a seven-membered ring

Physical state

Colorless liquid

Flammability

Flammable

Stability

More stable than the parent carboxylic acid compound due to the methyl ester group

Handling precautions

Should be handled with care

Applications

Building block in organic synthesis, used in the production of various organic compounds

Potential uses

Pharmaceutical, agrochemical, and materials science industries

Upstream product

• 544-25-2 Cyclohepta-1,3,5-triene 
• 27332-48-5 1-(cyclohepta-1,3,5-trien-1-yl)ethan-1-one 
• 27332-44-1 1,3,5-cycloheptatriene-1-carboxylic acid 
• 75-36-5 acetyl chloride 
• 67-56-1 methanol 
• 32399-46-5 7-(methoxycarbonyl)cycloheptatriene 
• 186581-53-3 diazomethane 

Downstream Products

• 93-58-3 benzoic acid methyl ester 
• 4122-56-9 methyl o-formylbenzoate 
• 194657-06-2 Methyl 6,7-dioxabicyclo[3.2.2]nona-2,8-diene-3-carboxylate 

Relevant articles and documents

Synthesis of Enantiopure 6,11-Methylene Lipoxin B4 Methyl Ester

The synthesis of Lipoxin B4 analogs (LXB4) to gain access to stabilized inflammation resolving compounds is an actual field of research. Focusing on variation and stabilization of the conjugated E,Z,E,E C6–C13 tetraene moiety of natural LXB4, a methylene bridge introduced between C6 and C11 suppresses any Z/E isomerization of the C8–C9 olefin. Intending to enable prospective structure variations in connection with the C1–C5 and C14–C20 fragments, a convergent total synthesis has been developed. Optically active C1–C12 building blocks were build-up from cycloheptatriene 1-carbonester (C6–C11, C21) and glutaryl chloride (C1–C5) using Friedel-Crafts-type acylation and chiral HPLC. The C13–C20 segment had been generated via a five-step sequence starting from heptanoyl chloride. Horner key olefination enabled the assembly of the carbon backbone. A final five-step sequence including a chelate Cram reduction of the unsaturated ketone moiety afforded the target 6,11-methylene LXB4 methyl ester.

Base-catalysed isomerization of 7-(methoxycarbonyl)-1,3,5-cycloheptatriene

In basic alcohol, 7-(methoxycarbonyl)-1,3,5-cycloheptatriene (7b) forms its 2-, 3- and 1-isomers (viz. 2b, 3b and 1b) in successive reactions.All isomers show specific hydrogen exchange in CD3ONa/CD3OD.For 3- and 1-(methoxycarbonyl)-1,3,5-cycloheptatriene vinylic hydrogen atoms are exchanged rather than the ''allylic'' 7-H atoms.