6203-08-3

Basic information

• Product Name: METHYL BICYCLO[2.2.1]HEPT-5-ENE-2-CARBOXYLATE
• Synonyms: METHYL 8,9,10-TRINORBORNA-5-ENE-2-CARBOXYLATE;METHYL BICYCLO[2.2.1]HEPT-5-ENE-2-CARBOXYLATE;METHYL 5-NORBORNENE-2-CARBOXYLATE;BICYCLO[2.2.1]HEPT-5-ENE-2-CARBOXYLIC ACID METHYL ESTER;8,9,10-TRINORBORNA-5-ENE-2-CARBOXYLIC ACID METHYL ESTER;5-NORBORNENE-2-CARBOXYLIC ACID METHYL ESTER;5-NORBORNENE-2-CARBOXYLIC METHYL ESTER;Methyl 5-Norbornene-2-carboxylate (endo- and exo- mixture)
• CAS NO: 6203-08-3
• Molecular Formula: C₉H₁₂O₂
• Molecular Weight: 152.19
• Product Categories: Norbornene Derivatives
• Mol File: 6203-08-3.mol

Chemical Properties

• Boiling Point: 195.8 °C at 760 mmHg
• Flash Point: 62.5 °C
• Appearance: /
• Density: 1.06
• Vapor Pressure: 0.412mmHg at 25°C
• Refractive Index: 1.4720 to 1.4770
• CAS DataBase Reference: METHYL BICYCLO[2.2.1]HEPT-5-ENE-2-CARBOXYLATE(CAS DataBase Reference)
• NIST Chemistry Reference: METHYL BICYCLO[2.2.1]HEPT-5-ENE-2-CARBOXYLATE(6203-08-3)
• EPA Substance Registry System: METHYL BICYCLO[2.2.1]HEPT-5-ENE-2-CARBOXYLATE(6203-08-3)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• RIDADR: NA 1993 / PGIII
• WGK Germany: 3
• Hazardous Substances Data: 6203-08-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
METHYL BICYCLO[2.2.1]HEPT-5-ENE-2-CARBOXYLATE is used as an intermediate in the synthesis of pharmaceutical compounds for [application reason]. Its unique bicyclic structure and functional groups contribute to the development of new drugs with specific therapeutic properties.
Used in Agrochemical Industry:
In the agrochemical industry, METHYL BICYCLO[2.2.1]HEPT-5-ENE-2-CARBOXYLATE is used as a precursor in the production of agrochemicals for [application reason]. Its chemical properties allow for the creation of effective pesticides, herbicides, or other agricultural chemicals that can enhance crop protection and yield.
Used in Organic Synthesis:
METHYL BICYCLO[2.2.1]HEPT-5-ENE-2-CARBOXYLATE is used as a key building block in organic synthesis for [application reason]. Its reactivity and structural features enable the formation of a wide range of organic molecules with diverse applications in various industries, including materials science, fragrances, and specialty chemicals.

InChI:InChI=1/C9H12O2/c1-11-9(10)8-5-6-2-3-7(8)4-6/h2-3,6-8H,4-5H2,1H3

Upstream product

• 67-56-1 methanol 
• 186581-53-3 diazomethane 
• 120-74-1 (1S,2S,4S)-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid 
• 934-30-5 5-norbornene-endo-2-carboxylic acid 
• 136520-59-7 methyl (5R,6R)-5-exo-formylbicyclo<2.2.1>hept-2-eno-6-endo-carboxylate 
• 136520-58-6 methyl (5R,6R)-6-endo-formylbicyclo<2.2.1>hept-2-eno-5-exo-carboxylate 
• 120-74-1 (-)-(1S,4S,5R)-bicyclo<2.2.1>hept-2-ene-5-carboxylic acid 
• 120-74-1 (1R,2R)-5-norbornene-2-carboxylic acid 
• 120-74-1 (1R,2S)-5-norbornene-2-carboxylic acid 

Downstream Products

• 120-74-1 (-)-(1S,4S,5R)-bicyclo<2.2.1>hept-2-ene-5-carboxylic acid 
• 95-12-5 5-hydroxymethyl-2-norbornene 
• 13360-81-1 5-norbornene-2-methanol 
• 15507-06-9 5-norbornene-2-methanol 
• 934-30-5 5-norbornene-endo-2-carboxylic acid 
• 120-74-1 endo-norbornenecarboxylic acid 
• 934-30-5 exo-5-norbornene-2-carboxylic acid 
• 109704-61-2 endo-5-(diphenylhydroxymethyl)-norbornene 
• 22664-23-9 carbomethoxy-2 exo hydroxy-6 exo bicyclo <2.2.1> heptane 
• 6712-12-5 (1S,3R,6S,7S)-4-Oxa-tricyclo[4.2.1.0^3,7]nonan-5-one 
• 7167-28-4 methyl 2-endo-methylbicyclo[2.2.1]hept-5-ene-2-exo-carboxylate 
• 7167-29-5 methyl 2-exo-methylbicyclo[2.2.1]hept-5-ene-2-endo-carboxylate 
• 100976-00-9 Benzoic acid bicyclo[2.2.1]hept-5-en-2-ylmethyl ester 
• 344585-18-8 (1R,2R,4S)-2-Isocyanato-bicyclo[2.2.1]heptane 

Relevant articles and documents

Use of functionalized onium salts as a soluble support for organic synthesis

The invention relates to the use of a onium salt functionalized by at least one organic function, as a soluble support, in the presence of at least one organic solvent, for organic synthesis of a molecule, in a homogenous phase, by at least one transformation of said organic function. The onium salt enables the synthesized molecule to be released. The onium salt is present in liquid or solid form at room temperature and corresponds to formula A1+, X1?, wherein A1+ represents a cation and X1? represents an anion.

Novel Potassium-Channel Openers: Preparation and Pharmacological Evaluation of Racemic and Optically Active N-(6-Amino-3-pyridyl)-N'-bicycloalkyl-N"-cyanoguanidine Derivatives

The previous paper reported on the synthesis and pharmacological evaluation of N-(6-amino-3-pyridyl)-N'-bicycloalkyl-N"-cyanoguanidine derivatives, from among which three compounds were selected as potent potassium-channel openers. In the present study, selected compounds were tested for antagonism of potassium-induced contraction of rat aorta, hypotensive activity in normotensive rats, and diuretic activity in spontaneously hypertensive rats. This led to further evaluation of compound (+/-)-10 and selection of (+)-N-(6-amino-3-pyridyl)-N'-hept-2-yl>-N"-cyanoguanidine ((+)-10) (AL0670) for development as an antihypertensive agent. Although AL0670 is regarded as a pinacidil-type K+-channel opener, it showed different pharmacological and conformational profiles from pinacidil.

Stereoselection in Thermal Asymmetric Diels-Alder Reactions. Electronic vs Steric Effects

Experimental evidence was found for an electronic contribution favoring the cisoid conformation of α,β-unsaturated carbonyl compounds in thermal Diels-Alder transition states.

Transformations of unsaturated acyclic sugars into enantiomerically pure norbornene derivatives

The C7 acyclic unsaturated-sugar ester 1, derived from L-arabinose, and its enantiomer serve as convenient dieneophiles for chirality transfer for synthesis of optically pure carbocyclic derivatives through cycloaddition reactions.Reaction of 1 with cyclopentadiene may be controlled to give preparative access to the 5,6-disubstituted norbornene adducts 4a, 5a and 7a, according to the conditions used.The distribution of the four possible isomeric products from this cycloaddition was quantitated, and the effect of substitutional variation on the precursor dienophile 1 was also examined.Adducts 4a and 5a were transformed into such substituted carbocycles of known absolute configuration as the methyl esters (11 and 12) of norbornene (bicyclohept-2-ene)-6-carboxylic acid and nortricyclane (tricyclo2,6>heptane)-3-carboxylic acid in optically pure form, specifically through decarbonylation reactions using RhCl(PPh3)3 (Wilkinson's complex) and Cl.The optical purity of 12 was established by the use of a chiral lanthanide shift-reagent.

INFLUENCE OF POLAR GROUPS IN THERMAL AND LEWIS ACID PROMOTED ASYMMETRIC DIELS-ALDER ADDITIONS: LACTIC ACID DERIVATIVES AS PRACTICAL HIGHLY SELECTIVE AND CONFIGURATIONALLY DICHOTOMIC REAGENTS

Diels-Alder reactions of the acrylate of (S)-ethyl lactate with cyclopentadiene proceed with diastereoface-selectivity of up to 85:15 (non catalyzed) and 93:7 (TiCl4-promoted).Depending on the Lewis acid, products of inverse configuration are obtained.In conjunction with facile product analysis by LC, effective means for suppression of the polymerization of diene, and virtually epimerization-free ester hydrolysis these findings constitute a method for large scale practical applications of the asymmetric Diels-Alder reaction.