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1792-81-0

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1792-81-0 Usage

Synthesis

To a mixture of N-methylmorpholine-N-oxide.2H2O (18.2 g, 155 mmol), water ?(50 mL), acetone (20 mL), and osmium tetroxide (80 mg) in t-butanol (8 mL) was added distilled cyclohexene (10.1 mL, 100 mmol). The reaction was slightly exothermic initially and was maintained at room temperature with a water bath. The reaction was complete after stirring overnight at room temperature under nitrogen. A slurry of 1 g of sodium hydrosulfifite, 12 g of magnesium silicate (magnesol), and 80 ml of water was added, and the magnesol was fifiltered. The fifiltrate was neutralized to pH 7 with 1 N H2SO4, the acetone was evaporated under vacuum, and the pH was further adjusted to pH 2. The solution was saturated with NaCl and extracted with EtOAc. The aqueous phase was concentrated by azeotroping with n-butanol and further extracted with ethyl acetate. The combined ethyl acetate layers were dried and evaporated, yielding 11.2 g (96.6%) of crystalline solid. Recrystallization from ether provided 10.6 g (91%) of cis-1,2-cyclohexanediol, mp 95–97°C. Reference: Van Rheenen, V.; Kelly, R. C.; Cha, D. Y. Tetrahedron Lett. 1976, 17, 1973?1976.

Chemical Properties

White to light beige crystalline flakes or powder

Uses

cis-1,2-Cyclohexanediol is a reagent used in the synthesis of boronic esters of corannulene which are used to prepare icosahedral supramolecules.

Definition

ChEBI: A cyclohexane-1,2-diol with cis-configuration.

General Description

Core-shell-like silica nickel species nanoparticle catalyzed dehydrogenation of 1,2-cyclohexanediol to catechol is reported. Crystal structure of a Cr(V) complex with cis-1,2-cyclohexanediol is reported. Enzymatic oxidation of cis-1,2-cyclohexanediol by Gluconobacter oxydans (ATCC 621) is reported.

Check Digit Verification of cas no

The CAS Registry Mumber 1792-81-0 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 1,7,9 and 2 respectively; the second part has 2 digits, 8 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 1792-81:
(6*1)+(5*7)+(4*9)+(3*2)+(2*8)+(1*1)=100
100 % 10 = 0
So 1792-81-0 is a valid CAS Registry Number.
InChI:InChI=1/C6H12O2/c7-5-3-1-2-4-6(5)8/h5-8H,1-4H2/t5-,6+

1792-81-0 Well-known Company Product Price

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  • Aldrich

  • (361267)  cis-1,2-Cyclohexanediol  99%

  • 1792-81-0

  • 361267-1G

  • 370.89CNY

  • Detail

1792-81-0SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name cis-cyclohexane-1,2-diol

1.2 Other means of identification

Product number -
Other names Grandidentol

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:1792-81-0 SDS

1792-81-0Relevant articles and documents

A heterogeneous cis-dihydroxylation catalyst with stable, site-isolated osmium-diolate reaction centers

Severeyns, An,De Vos, Dirk E.,Fiermans, Lucien,Verpoort, Francis,Grobet, Piet J.,Jacobs, Pierre A.

, p. 586 - 589 (2001)

Involatile OsO4! A tetrasubstituted olefin is immobilized on SiO2 and reacts with OsO4 to form a stable osmate (IV) ester (see scheme), which is a leak-proof heterogeneous catalyst for the cis-dihydroxylation of olefins.

Ionic liquid-immobilized catalytic system for biomimetic dihydroxylation of olefins

Closson, Adam,Johansson, Mikael,Baeckvall, Jan-E.

, p. 1494 - 1495 (2004)

A biomimetic catalytic system for dihydroxylation of olefins consisting of OsO4, N-methylmorpholine, and a flavin has been immobilized in an ionic liquid. This immobilized catalytic system is highly efficient for dihydroxylation with 30% aqueous H2O2 and it can be reused (at least 5 times) without loss of activity.

Osmium(III) and osmium(V) complexes bearing a macrocyclic ligand: A simple and efficient catalytic system for cis-dihydroxylation of alkenes with hydrogen peroxide

Sugimoto, Hideki,Ashikari, Kenji,Itoh, Shinobu

, p. 2154 - 2160 (2013)

A simple protocol that uses [OsIII(OH)(H2O)(L-N 4Me2)](PF6)2 (1; L-N 4Me2=N,N′-dimethyl-2,11-diaza[3.3](2,6) pyridinophane) as a catalyst and H2O2 as a terminal oxidant for efficient cis-1,2-dihydroxylation of alkenes is presented. Unfunctionalized (or aliphatic) alkenes and alkenes/styrenes containing electron-withdrawing groups are selectively oxidized to the corresponding vicinal diols in good to excellent yields (46-99 %). In the catalytic reactions, the stoichiometry of alkene:H2O2 is 1:1, and thus the oxidant efficiency is very high. For the dihydroxylation of cyclohexene, the catalytic amount of 1 can be reduced to 0.01 mol % to achieve a very high turnover number of 5500. The active oxidant is identified as the Os V(O)(OH) species (2), which is formed via the hydroperoxide adduct, an OsIII(OOH) species. The active oxidant 2 is successfully isolated and crystallographically characterized. The wizard of Os: A simple protocol that uses [OsIII(OH)(H2O)(L-N4Me 2)](PF6)2 (1) and H2O2 for efficient cis-1,2-dihydroxylation of alkenes is presented. Unfunctionalized (or aliphatic) alkenes and alkenes/styrenes containing electron-withdrawing groups were converted into the corresponding vicinal diols in good to excellent yields. It has been confirmed that the OsV(O)(OH) species (2) is the active oxidant, which is formed via the hydroperoxide adduct A. Copyright

-

Gunstone,Morris

, p. 487,489 (1957)

-

Contribution of flavonoids and catechol to the reduction of ICAM-1 expression in endothelial cells by a standardised Willow bark extract

Freischmidt,Jürgenliemk,Kraus,Okpanyi,Müller,Kelber,Weiser,Heilmann

, p. 245 - 252 (2012)

Introduction: A quantified aqueous Willow bark extract (STW 33-I) was tested concerning its inhibitory activity on TNF-α induced ICAM-1 expression in human microvascular endothelial cells (HMEC-1) and further fractionated to isolate the active compounds.

A New Regio- and Stereo-selective Functionalization of Allylic and Homoallylic Alcohols

Cardillo, Giuliana,Orena, Mario,Porzi, Gianni,Sandri, Sergio

, p. 465 - 466 (1981)

A new, highly regio- and stereo-selective synthesis of cyclic iodocarbonates of allylic and homoallylic alcohols involving cyclofunctionalization of the corresponding alcohol carbonates is described.

A new coupled catalytic system for dihydroxylation of olefins by H2O2 [5]

Bergstad, Katarina,Jonsson, Sandra Y.,B?ckvall, Jan-E.

, p. 10424 - 10425 (1999)

-

Lambert et al.

, p. 3619,3622 (1970)

Electrochemical Borylation of Alkyl Halides: Fast, Scalable Access to Alkyl Boronic Esters

Cao, Yangmin,Hu, Ping,Huang, Cheng,Liu, Zhao,Lu, Qingquan,Ma, Wan,Peng, Pan,Qi, Xiaotian,Wang, Bingbing

supporting information, p. 12985 - 12991 (2021/09/03)

Herein, a fast, scalable, and transition-metal-free borylation of alkyl halides (X = I, Br, Cl) enabled by electroreduction is reported. This process provides an efficient and practical access to primary, secondary, and tertiary boronic esters at a high current. More than 70 examples, including the late-stage borylation of natural products and drug derivatives, are furnished at room temperature, thereby demonstrating the broad utility and functional-group tolerance of this protocol. Mechanistic studies disclosed that B2cat2 serves as both a reagent and a cathodic mediator, enabling electroreduction of difficult-to-reduce alkyl bromides or chlorides at a low potential.

Olefin reaction in the catalyst and the olefin production

-

Paragraph 0147-0149, (2020/10/31)

PROBLEM TO BE SOLVED: To provide a catalyst for obtaining an olefin in high selectivity with a vicinal diol as a raw material.SOLUTION: A catalyst for olefination reaction for use in a reaction to produce an olefin by a reaction of a polyol, having two adjacent carbon atoms each having a hydroxy group, with hydrogen comprises: a carrier; at least one oxide selected from the group consisting of oxides of the group 6 elements and oxides of the group 7 elements supported on the carrier; and at least one metal selected from the group consisting of silver, iridium, and gold supported on the carrier.SELECTED DRAWING: None

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