6920-22-5 Usage
Description
DL-1,2-Hexanediol is a synthetic organic compound with the chemical formula C6H12O2. It is a chiral molecule, meaning it has two enantiomeric forms (D and L) that are mirror images of each other. DL-1,2-Hexanediol is a colorless, odorless liquid with a sweet taste and is soluble in water, alcohol, and ether.
Uses
Used in Chemical Synthesis:
DL-1,2-Hexanediol is used as a solvent in various chemical reactions to dissolve other compounds in a formulation. Its ability to dissolve a wide range of substances makes it a versatile solvent in the synthesis of various organic compounds.
Used in Pharmaceutical Industry:
DL-1,2-Hexanediol is used in the ruthenium-catalyzed synthesis of oxazolidin-2-ones from urea. Oxazolidin-2-ones are a class of antibiotics with broad-spectrum activity against gram-positive bacteria, including methicillin-resistant Staphylococcus aureus (MRSA). The use of DL-1,2-Hexanediol in this synthesis process aids in the production of these important antibiotics.
Used in Organic Synthesis:
DL-1,2-Hexanediol can undergo ruthenium-hydride catalyzed dehydrative coupling with anilines to form substituted indole and quinoline products. Indole and quinoline derivatives are important building blocks in the synthesis of various pharmaceuticals, agrochemicals, and natural products. The use of DL-1,2-Hexanediol in this reaction allows for the efficient synthesis of these valuable compounds.
Preparation
1,2-Hexanediol was prepared in about 45% over-all yield by a-bromination of caproic acid, hydrolysis to a-hydroxycaproic acid, and reduction with lithium aluminum hydride.Using the oxidant of H2O2, the organic acid is oxidized to peroxyacid, and the peroxyacid then epoxidizes the olefin double bond, and finally hydrolyzes to obtain 1,2-hexanediol.
benefits
1,2 hexanediol is most commonly used as a solvent in skincare formulation. It pulls the moisture up from the deeper levels of the skin, as well as from the air, to help keep the top layers of your skin from drying out. This makes It very effective at keeping your skin hydrated and providing long-term moisture. It can also help to disperse pigments more evenly in makeup products and boost the antimicrobial activity of preservatives.
Flammability and Explosibility
Nonflammable
Safety
1,2 hexanediol has been proven to be a completely safe and non-irritating ingredient. In an in-use safety evaluation for skin irritation and sensitization potential, 28 participants (males and females) were instructed to use a body wash containing 0.15% 1,2- hexanediol for a minimum of 3 times per week over a 30-day period. There was no evidence of erythema, edema, or dryness of application sites in any of the participants, and it was concluded that the product did not demonstrate a potential for eliciting skin irritation or sensitization.?
Purification Methods
Fractionally distil it, preferably in a vacuum. Alternatively, dissolve it in Et2O, dry with K2CO3 then Na2SO4, filter, evaporate and distil it in a vacuum. The bis-4-nitrobenzoyl derivative has m 101.5-102.5o. [Rudloff Can J Chem 36 486 1958, Beilstein 1 I 251, 1 III 2200, 1 IV 2554.]
Check Digit Verification of cas no
The CAS Registry Mumber 6920-22-5 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 6,9,2 and 0 respectively; the second part has 2 digits, 2 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 6920-22:
(6*6)+(5*9)+(4*2)+(3*0)+(2*2)+(1*2)=95
95 % 10 = 5
So 6920-22-5 is a valid CAS Registry Number.
InChI:InChI=1/C6H14O2/c1-2-3-4-6(8)5-7/h6-8H,2-5H2,1H3/t6-/m1/s1
6920-22-5Relevant articles and documents
A METHOD FOR PREPARING 1,2-HEXANEDIOL
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Paragraph 0040; 0064-0071; 0076, (2021/10/27)
The present invention provides a colourless. A method for producing high purity 1,2 - hexanediol by reacting 1 - hexenes and hydrogen peroxide to produce 1,2 - hexanediol and reacting with a reducing agent and activated carbon to produce colorless, odorless high purity 1,2 - hexanediol. The method for preparing 1,2 - hexanediol according to the present invention greatly improves purity, yield and quality, is simple and economical and industrially useful, and can be mass-produced and can be applied to various industrial fields.
Diol-Ritter Reaction: Regio- And Stereoselective Synthesis of Protected Vicinal Aminoalcohols and Mechanistic Aspects of Diol Monoester Disproportionation
Abboud, Khalil A.,Cheng, Kevin,Klosin, Jerzy,Kruper, William J.,Kruper, William R.,Lysenko, Ivan,Ondari, Mark E.,Thomas, Pulikkottil J.
, (2021/10/20)
The well-known epoxide-Ritter reaction generally affords oxazolines with poor to average regioselectivity. Herein, a mechanism-based study of the less known diol-Ritter reaction has provided a highly regioselective procedure for the synthesis of 1-vic-amido-2-esters from either terminal epoxides or 1,2-diols via Lewis acid-catalyzed monoesterification. When treated with a stoichiometric Lewis acid catalyst (BF3), these diol monoesters form dioxonium cation intermediates that are ring-opened with nitrile nucleophiles to form nitrilium intermediates, which undergo rapid and irreversible hydration to give the desired amidoesters. Diester byproduct formation is irreversible and appears to occur through disproportionation of diol monoester. With chiral epoxide starting materials, the formation of amidoester occurs with retention of configuration and no apparent erosion of optical purity as determined by single-crystal X-ray analyses and chiral chromatography, respectively. The direct access to chiral vic-amidoesters is especially practical with regard to the synthesis of antibacterial oxazolidinone analogues of the Zyvox antimicrobial family.
An Amphiphilic (salen)Co Complex – Utilizing Hydrophobic Interactions to Enhance the Efficiency of a Cooperative Catalyst
Solís-Mu?ana, Pablo,Salam, Joanne,Ren, Chloe Z.-J.,Carr, Bronte,Whitten, Andrew E.,Warr, Gregory G.,Chen, Jack L.-Y.
supporting information, p. 3207 - 3213 (2021/06/01)
An amphiphilic (salen)Co(III) complex is presented that accelerates the hydrolytic kinetic resolution (HKR) of epoxides almost 10 times faster than catalysts from commercially available sources. This was achieved by introducing hydrophobic chains that increase the rate of reaction in one of two ways – by enhancing cooperativity under homogeneous conditions, and increasing the interfacial area under biphasic reaction conditions. While numerous strategies have been employed to increase the efficiency of cooperative catalysts, the utilization of hydrophobic interactions is scarce. With the recent upsurge in green chemistry methods that conduct reactions ‘on water’ and at the oil-water interface, the introduction of hydrophobic interactions has potential to become a general strategy for enhancing the catalytic efficiency of cooperative catalytic systems. (Figure presented.).
