35730-27-9

Basic information

• Product Name: 1,3-Cyclopentadiene-1-carboxylic acid, methyl ester (6CI,9CI)
• Synonyms: 1,3-Cyclopentadiene-1-carboxylic acid, methyl ester (6CI,9CI)
• CAS NO: 35730-27-9
• Molecular Formula: C₇H₈O₂
• Molecular Weight: 124.13722
• Product Categories: ACIDHALIDE
• Mol File: 35730-27-9.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 170.7°Cat760mmHg
• Flash Point: 55.6°C
• Appearance: /
• Density: 1.119g/cm³
• Vapor Pressure: 1.45mmHg at 25°C
• Refractive Index: 1.51
• CAS DataBase Reference: 1,3-Cyclopentadiene-1-carboxylic acid, methyl ester (6CI,9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-Cyclopentadiene-1-carboxylic acid, methyl ester (6CI,9CI)(35730-27-9)
• EPA Substance Registry System: 1,3-Cyclopentadiene-1-carboxylic acid, methyl ester (6CI,9CI)(35730-27-9)

Safety Data

• Hazardous Substances Data: 35730-27-9(Hazardous Substances Data)

Usage

Usage

Building block in the synthesis of pharmaceuticals and agrochemicals

Physical state

Colorless liquid

Odor

Strong, fruity

Flammability

Flammable

Primary use

Intermediate in the production of various chemicals

Additional use

Synthesis of organic compounds

Health hazards

Potential irritant to skin, eyes, and respiratory system

Safety measures

Proper protective measures required for use and handling

InChI:InChI=1/C7H8O2/c1-9-7(8)6-4-2-3-5-6/h2-4H,5H2,1H3

Upstream product

• 119-36-8 methyl salicylate 
• 110210-71-4 dimethano-1,4,5,8 hexahydro-1,4,4a,5,8,8a naphtalene carboxylate-4a de methyle 
• 67-56-1 methanol 
• 124-38-9 carbon dioxide 
• 542-92-7 cyclopenta-1,3-diene 
• 3604-36-2 methyl bicyclo[2.2.1]hepta-2,5-diene-2-carboxylate 

Downstream Products

• 4630-80-2 methyl cyclopentane carboxylate 
• 75444-03-0 endo-Tricyclo<3.2.1.0^2,4>octyl-1-carbinyl Tosylate 
• 75444-04-1 endo-Tricyclo<3.2.1.0^2,4>octane-1-carboxylic Acid 
• 30778-59-7 diazocyclopentadien-2-ylcarboxylic acid 
• 127820-44-4 5-[2,2-Dimethyl-prop-(E)-ylidene]-cyclopenta-1,3-dienecarboxylic acid methyl ester 
• 75421-03-3 methyl endo-tricyclo<3.2.1.0^2,4>-oct-6-ene-1-carboxylate 

Relevant articles and documents

Ketene-Ketene interconversion. 6-Carbonylcyclohexa-2,4-dienone-hepta-1,2,4, 6-tetraene-1,7-dione-6-oxocyclohexa-2,4-dienylidene and wolff rearrangement to fulven-6-one

6-Carbonylcyclohexa-2,4-dienone (1) has been generated by flash vacuum thermolysis (FVT) with Ar-matrix isolation of methyl salicylate (7), 2-phenylbenzo-1,3-dioxan-4-one (8), phthalic peranhydride (9), and benzofuran-2,3-dione (11) and also by matrix photolysis of 9, 11, and 2-diazocyclohepta-4,6-dien-1,3-dione (12). In each case, FVT above 600 °C results in decarbonylation of 1 and Wolff rearrangement to fulven-6-one (13) either concertedly or via open-shell singlet 6-oxocyclohexa-2,4-dienylidene (18). Ketenes 1 and 13 were characterized by IR spectroscopy. Photolysis of matrix-isolated 1 at 254 nm also results in the slow formation of 13. The sequential formation of ketenes 1 and 13 from 7 has also been monitored by FVT-mass spectrometry, and 13 has been trapped with MeOH to afford methyl 1,3-cyclopentadiene-1- and -2-carboxylates 15 and 16. FVT of methyl salicylate-1-13C 7a revealed a deep-seated rearrangement of the 13C-labeled 1a to hepta-1,2,4,6-tetraen-1,7-dione (17a) by means of electrocyclic ring opening followed by a facile 1,5-H shift and recyclization prior to CO-elimination and ring contraction to 13C-labeled 13. The rearrangement mechanism is supported by M06-2X/6-311++G(d,p) calculations, which predict feasible barriers for the FVT rearrangements and confirm the observed labeling pattern in the isolated methyl salicylate 7a/7b and methyl cyclopentadienecarboxylates 20 and 21 resulting from trapping of 13 with MeOH.

Synthesis of some 1,2-Dihalogenonorbornanes

The synthesis of 1,2exo-dibromo-norbornane as well as the preparation of the configurational isomers of 2-bromo-1-iodo- and 2-chloro-1-iodo-norbornane are described.