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Bicyclo[2.2.2]octa-2,5,7-triene, also known as bicycloocta-2,5,7-triene or simply BOC, is a bicyclic, unsaturated hydrocarbon with the molecular formula C8H10. It features a unique eight-membered ring structure with two double bonds, making it an interesting compound in organic chemistry. BOC is a colorless liquid with a pungent odor and is insoluble in water but soluble in organic solvents. It is primarily used as a building block in the synthesis of various organic compounds, particularly in the pharmaceutical and chemical industries. Due to its reactive nature, BOC is also used as a protecting group in peptide synthesis, where it can be selectively removed under mild conditions.

500-24-3

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500-24-3 Usage

Check Digit Verification of cas no

The CAS Registry Mumber 500-24-3 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,0 and 0 respectively; the second part has 2 digits, 2 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 500-24:
(5*5)+(4*0)+(3*0)+(2*2)+(1*4)=33
33 % 10 = 3
So 500-24-3 is a valid CAS Registry Number.
InChI:InChI=1/C8H8/c1-2-8-5-3-7(1)4-6-8/h1-8H

500-24-3Relevant academic research and scientific papers

Epoxidation of Barrelene: Preparation and Properties of Oxahomobarrelenes

Weitemeyer, Christian,Preuss, Thomas,Meijere, Armin de

, p. 3993 - 4005 (2007/10/02)

A four-step synthesis makes barrelene (1) readily accessible on a 1-2 g scale.Upon epoxidation with KHCO3-buffered m-chloroperbenzoic acid 1 yields the mono- (2b), both the endo,exo- and exo,exo-isomeric bis- (3b and 4b) as well as the trisepoxide 5b.In the presence of traces of acid 2b very rapidly rearranges to cycloheptatriene-7-carbaldehyde (15), 5b undergoes a facile acid-catalyzed rearrangement to 4,7,11-trioxatrishomocubane (16).Under basic and neutral conditions 5b is stable towards virtually any nucleophile, its three epoxide rings can only be opened underreductive conditions with solvated electrons.On the other hand, endo,exo-dioxadihydrobishomobarrelene 20 and oxatrishomobarrelene 23 are readily attacked at the oxirane rings by lithium iodide/disodium hydrogen phosphate.

SYNTHESIS OF TETRACYCLO2,4.03,6>OCT-7-ENE AND SOME OF ITS DERIVATIVES

Stapersma, J.,Rood, I. D. C.,Klumpp, G. W.

, p. 191 - 199 (2007/10/02)

A full account is given of the synthesis of the title compound, its 7,8-dihydro-analogue and of some of its derivatives.

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