5453-80-5

Basic information

• Product Name: 5-Norbornene-2-carboxaldehyde
• Synonyms: 2-Formyl-5-norbornene;5-Formylbicyclo-2-heptene;5-Formylbicyclohept-2-ene;5-Norbornane-2-carboxaldehyde;5-norbornene-2-carboxaldehyde,mixtureofendoandexo;Bicyclo[2.2.1]hept-5-en-2-aldehyde;TIMTEC-BB SBB005755;5-NORBORNENE-2-CARBALDEHYDE
• CAS NO: 5453-80-5
• Molecular Formula: C₈H₁₀O
• Molecular Weight: 122.16
• EINECS: 226-698-9
• Product Categories: Norbornene Derivatives
• Mol File: 5453-80-5.mol
• Article Data: 64

Chemical Properties

• Boiling Point: 67-70 °C12 mm Hg(lit.)
• Flash Point: 123 °F
• Appearance: White to yellow to beige/Powder
• Density: 1.03 g/mL at 20 °C(lit.)
• Vapor Pressure: 0.819mmHg at 25°C
• Refractive Index: n20/D 1.490(lit.)
• Storage Temp.: Flammables area
• Water Solubility: insoluble
• BRN: 1363813
• CAS DataBase Reference: 5-Norbornene-2-carboxaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Norbornene-2-carboxaldehyde(5453-80-5)
• EPA Substance Registry System: 5-Norbornene-2-carboxaldehyde(5453-80-5)

Safety Data

• Hazard Codes: Xi
• Statements: 10-36/37/38
• Safety Statements: 23-37/39-26-16
• RIDADR: UN 1989 3/PG 3
• WGK Germany: 3
• TSCA: Yes
• HazardClass: 3
• PackingGroup: III
• Hazardous Substances Data: 5453-80-5(Hazardous Substances Data)

Usage

Description

5-Norbornene-2-carboxaldehyde is a clear colorless to yellow liquid that is a key component in various chemical reactions and applications due to its unique chemical properties.

Uses

Used in Chemical Synthesis:
5-Norbornene-2-carboxaldehyde is used as a Diels-Alder adduct of acrolein and cyclopentadiene for the synthesis of norbornene-derived homopolymers having pendent t-Boc-protected quinizarin moieties. This application is particularly useful in creating patterned fluorescence images.
Used in Polymer Synthesis:
In the field of polymer chemistry, 5-Norbornene-2-carboxaldehyde is used as a protected form of acrolein. The double bond in this molecule can be liberated by cycloreversion, which is a valuable step in the synthesis of various polymers, such as 2-vinylimidazole.
Used in Transition Metal-Catalyzed Synthesis:
5-Norbornene-2-carboxaldehyde is also utilized in the transition metal-catalyzed synthesis of norbornene-derived homopolymers. This process is significant for the development of new materials with specific properties and applications in various industries.

InChI:InChI=1/C8H10O/c9-5-8-4-6-1-2-7(8)3-6/h1-2,5-8H,3-4H2

Upstream product

• 60-29-7 diethyl ether 
• 542-92-7 cyclopenta-1,3-diene 
• 107-02-8 acrolein 
• 120-74-1 5-carboxybicyclo<2.2.1>hept-2-ene 
• 769-85-7 methyl exo-5-norbornene-2-carboxylate 
• 934-30-5 exo-5-norbornene-2-carboxylic acid 
• 5453-80-5 bicyclo[2.2.1]hept-5-ene-2-carbaldehyde 
• 78-85-3 2-methylpropenal 
• 19926-90-0 (+/-)-endo-bicyclo[2.2.1]hept-5-ene-2-carbaldehyde 
• 201230-82-2 carbon monoxide 
• 121-46-0 bicyclo[2.2.1]hepta-2,5-diene 
• 292638-85-8 acrylic acid methyl ester 
• 90086-80-9 bicyclo<2.2.1>hept-5-ene-2-carboxaldehyde oxime 
• 2890-96-2 5-norbornene-2-carbonitrile 

Downstream Products

• 85392-35-4 3-norborn-5-en-2-yl-2-pentyl-acrylaldehyde 
• 69412-65-3 2-methyl-1-norborn-5-en-2-yl-pent-1-en-3-one 
• 38284-42-3 2-methyl-3-norborn-5-en-2-yl-acrylaldehyde 
• 38284-38-7 3-methyl-4-norborn-5-en-2-yl-but-3-en-2-one 
• 2259-96-3 cyclothiazide 
• 15222-64-7 β-hepten-(5)-yl-(2)>-acrylsaeure 
• 22637-47-4 2,5-Methylen-1,2,5,6-tetrahydro-benzal-p-chloracetophenon 
• 22637-48-5 2,5-Methylen-1,2,5,6-tetrahydro-benzal-p-bromacetophenon 
• 70353-45-6 1-norborn-5-en-2-yl-pentane-1,4-dione 
• 22637-49-6 2,5-Methylen-1,2,5,6-tetrahydro-benzalacetophenon 
• 22629-06-7 ethyl 3-(bicyclo[2.2.1]hept-5-en-2-yl)-2-cyanoacrylate 
• 73188-52-0 (1R,2S,4R)-2-Phenylsulfanyl-bicyclo[2.2.1]hept-5-ene-2-carbaldehyde 
• 16381-85-4 Cyclopropyl-(<2>norbornyl-methyl)-amin 
• 22629-10-3 2.5-Methylen-1.2.5.6-tetrahydro-benzal-malodinitril 

Relevant articles and documents

Method for preparing single-configuration C-2-position-monosubstituted norbornene derivative

The invention discloses a method for preparing a single-configuration C-2-position-monosubstituted norbornene derivative. The method comprises the following steps of: firstly, preparing exo-isomer enriched exo-isomer mixed 5-norbornene-2-carboxylic ester by taking commercial exo-isomer/endoisomer mixed 5-norbornene-2-carboxylic acid and large-steric-hindrance monohydric alcohol as raw materials; separating 5-norbornene-2-carboxylate with a single configuration through common column chromatography separation or fractionation; and finally, preparing the C-2-position-monosubstituted norbornene derivative with the single configuration from the separated 5-norbornene-2-carboxylate with the single configuration. The raw materials used in the invention are easy to obtain, the preparation process is simple, and the C-2-position-monosubstituted norbornene derivative with high purity (greater than 98%) and single configuration can be obtained.

NOVEL BENZOIMIDAZOLES AS SELECTIVE INHIBITORS OF INDOLEAMINE 2, 3-DIOXYGENASES

Disclosed herein are novel benzoimidazoles and pharmaceutical compositions comprising at least one such novel benzoimidazoles, processes for the preparation thereof, and the method for using the same in therapy. In particular, disclosed herein are certain novel benzoimidazoles that are useful for inhibiting indoleamine 2, 3-dioxygenase and for treating diseases or disorders mediated thereby.

Improving the efficiency of the Diels-Alder process by using flow chemistry and zeolite catalysis

The industrial application of the Diels-Alder reaction for the atom-efficient synthesis of (hetero)cyclic compounds constitutes an important challenge. Safety and purity concerns, related to the instability of the polymerization prone diene and/or dienophile, limit the scalability of the production capacity of Diels-Alder products in a batch mode. To tackle these problems, the use of a high-pressure continuous microreactor process was considered. In order to increase the yields and the selectivity towards the endo-isomer, commercially available zeolites were used as a heterogeneous catalyst in a microscale packed bed reactor. As a result, a high conversion (≥95%) and endo-selectivity (89:11) were reached for the reaction of cyclopentadiene and methyl acrylate, using a 1:1 stoichiometry. A throughput of 0.87 g h-1 during at least 7 h was reached, corresponding to a 3.5 times higher catalytic productivity and a 14 times higher production of Diels-Alder adducts in comparison to the heterogeneous lab-scale batch process. Catalyst deactivation was hardly observed within this time frame. Moreover, complete regeneration of the zeolite was demonstrated using a straightforward calcination procedure.