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5-Hydroxynorbornane 2,6-Lactone, also known as 1,3,4,4a,5,6-hexahydro-6-hydroxy-1,4-methanonaphthalene-2(3H)-one, is a cyclic ester chemical compound derived from the structural rearrangement of norbornene. It is commonly used in the synthesis of pharmaceuticals and other organic compounds, serving as a versatile building block in organic chemistry. Known for its pleasant odor, it also finds application as a flavor and fragrance ingredient in various products. Due to its potential hazards if not handled properly, care must be taken during its use.

92343-46-9

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92343-46-9 Usage

Uses

Used in Pharmaceutical Synthesis:
5-Hydroxynorbornane 2,6-Lactone is used as a key intermediate in the synthesis of various pharmaceuticals due to its unique cyclic structure and reactivity, contributing to the development of new drugs and medicinal compounds.
Used in Organic Chemistry:
As a building block in organic chemistry, 5-Hydroxynorbornane 2,6-Lactone is utilized for the creation of complex organic molecules, facilitating advancements in chemical research and the production of specialty chemicals.
Used in Flavor and Fragrance Industry:
5-Hydroxynorbornane 2,6-Lactone is used as a flavor and fragrance ingredient in various consumer products, capitalizing on its pleasant odor to enhance the sensory experience of these goods.
Used in Chemical Research:
In the field of chemical research, 5-Hydroxynorbornane 2,6-Lactone serves as a valuable compound for studying reaction mechanisms, exploring new synthetic routes, and developing innovative applications in material science and related disciplines.

Check Digit Verification of cas no

The CAS Registry Mumber 92343-46-9 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 9,2,3,4 and 3 respectively; the second part has 2 digits, 4 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 92343-46:
(7*9)+(6*2)+(5*3)+(4*4)+(3*3)+(2*4)+(1*6)=129
129 % 10 = 9
So 92343-46-9 is a valid CAS Registry Number.
InChI:InChI=1/C8H10O3/c9-6-3-1-4-5(2-3)8(10)11-7(4)6/h3-7,9H,1-2H2

92343-46-9SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 16, 2017

Revision Date: Aug 16, 2017

1.Identification

1.1 GHS Product identifier

Product name N-hydroxy-5-norbornene-2,3-second imide

1.2 Other means of identification

Product number -
Other names Dihydroxy-2-endo.3-exo-carboxy-6-endo-bicyclo<2.2.1>hepten-γ-lacton

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:92343-46-9 SDS

92343-46-9Relevant articles and documents

A new solid-phase reaction system utilizing a temperature-responsive catalyst: Oxidative cyclization with hydrogen peroxide

Hamamoto, Hiromi,Suzuki, Yachiyo,Takahashi, Hideyo,Ikegami, Shiro

, p. 2685 - 2689 (2008/09/20)

A switchable catalyst based on temperature change provides a novel solid-phase reaction system in water. An increase in catalyst affinity for organic substrates at higher temperature led to efficient activity driving the solid inner-phase reaction, and loss of affinity at lower temperature allowed easy separation of organic products upon completion of the reaction. Application of this catalyst intelligence to design a novel catalytic system brought about an efficient oxidative cyclization with hydrogen peroxide, a useful method of accessing oxygen heterocycles.

Amides containing two norbornene fragments. Synthesis and chemical transformations

Kas'yan,Isaev,Kas'yan,Golodaeva,Karpenko,Tarabara

, p. 1415 - 1426 (2007/10/03)

Reactions of stereochemically pure bicyclo[2.2.1]hept-5-en-exo- and endo-2-ylmethylamines with bicyclo[2.2.1]hept-2-ene-5-carbonyl chlorides gave the corresponding carboxamides having two norbornene fragments. Their conformations and steric strains were studied by the MM2 molecular mechanics method, and electron density distribution in their molecules was determined by PM3 quantum-chemical calculations. The results of calculation of the energy of activation for epoxidation of the dienes in the gas phase and in solution (COSMO) showed that chemoselective oxidation of only one double bond therein is impossible. The corresponding diepoxy derivatives were synthesized by oxidation of the dienes with peroxyacetic acid; the oxidation of amides with endo orientation of the carbonyl group was accompanied by heterocyclization with formation of exo-2-hydroxy-4-oxatricyclo[4.2.1.03,7]nonan-5-one. Reduction of the amides and their epoxy derivatives with lithium tetrahydridoaluminate afforded the corresponding secondary amines possessing two cage-like fragments; the reduction products were functionalized at the nitrogen atom by treatment with p-nitrobenzenesulfonyl chloride and p-toluenesulfonyl isocyanate. The structure of the prepared compounds was confirmed by the IR and 1H and 13C NMR spectra.

Application of chemical P-450 model systems to studies on drug metabolism. Part X. Novel hydroxylactonization of γ,δ- and β,γ-unsaturated carboxylic acids with an iron porphyrin-iodosylbenzene system

Komuro, Masakatsu,Higuchi, Tsunehiko,Hirobe, Masaaki

, p. 2309 - 2313 (2007/10/03)

The oxidative hydroxylactonization of γ,δ- and β,γ-unsaturated carboxylic acids by a chemical cytochrome P-450 model and rat liver microsomal systems has been investigated. In the chemical system using meso-tetrakis(2,6-dichlorophenyl)porphyrin iron chloride [Fe(TDClPP)Cl] with iodosylbenzene (PhIO), γ,δ-unsaturated carboxylic acids have been converted into δ-hydroxy-γ-lactones in high yield and with high stereoselectivity. As an example of a β,γ-unsaturated carboxylic acid, indomethacin has been converted into the corresponding β-hydroxy γ-lactone. Several experiments directed toward mechanistic elucidation of the lactonization exclude a mechanism occurring via an epoxide intermediate. The products have been used as standards to identify the metabolites in the microsomal oxidation. In the case of indomethacin, the γ-lactone form is detected as a metabolite in the rat liver microsomal system, in a yield of 1.33%; the yield is significantly decreased in the presence of 2-diethylaminoethyl-2,2-diphenylvalerate hydrochloride (SKF-525A) and under a mixed CO-O2 (4:1) atmosphere. Thus, these metabolites are considered to be formed by a cytochrome P-450-dependent reaction.

A Further Synthetic Approach to the Adamantane Isomer 2,5-Trimethylenenorbornane (Tricyclo3,9>decane, 4-Homotwistbrendane)

Kaenel, Hans-Ruedi,Ganter, Camille

, p. 2453 - 2457 (2007/10/02)

A further synthetic approach to 2,5-trimethylenenorbornane (1; tricyclo3,9>decane, 4-homotwistbrendane), a member of the "adamantaneland", is described starting from methyl 5-oxo-2endo-norbornanecarboxylate (5).The required C2-chain was introduced by a Wittig-Horner reaction and the ring closure of the trimethylene bridge achieved by an acyloin condensation.

ACTION DU N-BROMOSUCCINIMIDE SUR LES DIOXOLANNES EN SERIE BICYCLOHEPTANIQUE. LIMITATION DES TRANSPOSITIONS DE WAGNER-MEERWEIN

Bazbouz, Akram,Christol, Henri,Coste, Jacques,Plenat, Francoise

, p. 2745 - 2755 (2007/10/02)

Vicinal benzoyloxy-trans-bicycloheptanic bromhydrins, otherwise difficult to obtain are formed from N-bromosuccinimide and norbornanes bearing a 2-aryl-1,3 dioxolane skeleton.The greater stability of the intermediate dioxolenium ion reduces the tendency towards both Wagner-Meerwein rearrangement and neighbouring group participation by chlorine, processes usually observed when a less stable intermediate is involved.Nevertheless, methoxycarbonyl neighbouring group participation and Wagner-Meerwein rearrangement occur in methoxycarbonylbicycloheptane and in a bornanic compound respectively.

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