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6920-22-5

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6920-22-5 Usage

Chemical Properties

clear colorless to light yellow liquid.

Uses

Different sources of media describe the Uses of 6920-22-5 differently. You can refer to the following data:
1. DL-1,2-Hexanediol is a solvent used to dissolve other compounds in a formulation.
2. 1,2-Hexanediol can be used in the ruthenium-catalyzed synthesis of oxazolidin-2-ones from urea. It can undergo ruthenium-hydride catalyzed dehydrative coupling with anilines to form substituted indole and quinoline products.

Definition

1,2-Hexanediol is a linear aliphatic diol with a carbon chain length containing six carbons. It is a synthetic preservative and moisture-binding agent belonging to a class of agents known as higher molecular glycols. It is considered non-sensitizing. It is ideal for use as an emollient, humectant, and wetting agent in cosmetic and skin care products.

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.

General Description

1,2-Hexanediol acts as cosurfactant, used for modifying the sodium dodecyl sulfate micelles. Solubility of 1,2-hexanediol in supercritical CO2 has been reported. It has a tendency of self-association to form micelle-like aggregates.

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

6920-22-5 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
  • Price
  • Detail
  • Alfa Aesar

  • (L06864)  1,2-Hexanediol, 97%   

  • 6920-22-5

  • 50g

  • 373.0CNY

  • Detail
  • Alfa Aesar

  • (L06864)  1,2-Hexanediol, 97%   

  • 6920-22-5

  • 250g

  • 1358.0CNY

  • Detail
  • Aldrich

  • (213691)  1,2-Hexanediol  98%

  • 6920-22-5

  • 213691-10G

  • 339.30CNY

  • Detail
  • Aldrich

  • (213691)  1,2-Hexanediol  98%

  • 6920-22-5

  • 213691-50G

  • 452.79CNY

  • Detail
  • Aldrich

  • (213691)  1,2-Hexanediol  98%

  • 6920-22-5

  • 213691-250G

  • 1,007.37CNY

  • Detail

6920-22-5SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name DL-1,2-Hexanediol

1.2 Other means of identification

Product number -
Other names HDO

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Solvents
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:6920-22-5 SDS

6920-22-5Synthetic route

1,2-Epoxyhexane
1436-34-6

1,2-Epoxyhexane

Hexane-1,2-diol
6920-22-5

Hexane-1,2-diol

Conditions
ConditionsYield
With water; erbium(III) triflate In acetonitrile at 25℃; for 1h;100%
With poly{[CuBa(pyridine-2,5-dicarboxylate)2(H2O)5]*H2O}; dihydrogen peroxide In water; acetonitrile at 40℃; for 2h; Catalytic behavior; Reagent/catalyst;100%
With water at 40℃; for 8h; Autoclave;99%
1-hexene
592-41-6

1-hexene

Hexane-1,2-diol
6920-22-5

Hexane-1,2-diol

Conditions
ConditionsYield
With poly{[CuBa(pyridine-2,5-dicarboxylate)2(H2O)5]*H2O}; dihydrogen peroxide In acetonitrile at 60℃; for 6h; Catalytic behavior; Reagent/catalyst;100%
With N-methyl-2-indolinone; fluorous OsO4 In water; acetone; tert-butyl alcohol at 20℃; for 36h;97%
With N-methyl-2-indolinone; polysulfone microencapsulated OsO4 In water; acetone; acetonitrile at 20℃; for 0.416667h;96%
2-hydroxyhexanoic acid ethyl ester
52089-55-1

2-hydroxyhexanoic acid ethyl ester

Hexane-1,2-diol
6920-22-5

Hexane-1,2-diol

Conditions
ConditionsYield
With trimethoxysilane; lithium methanolate In tetrahydrofuran for 9.5h; Heating;100%
With sodium tetrahydroborate at 65℃; for 10h;65%
2,3-epoxyhexanol
106498-75-3

2,3-epoxyhexanol

Hexane-1,2-diol
6920-22-5

Hexane-1,2-diol

Conditions
ConditionsYield
With Bu3Sn(HMPA)I; tri-n-butyl-tin hydride In tetrahydrofuran at 60℃; for 24h;100%
With titanium(IV) isopropylate; lithium borohydride In benzene for 2h; Ambient temperature;80%
4-butyl-1,3-dioxolan-2-one
66675-43-2

4-butyl-1,3-dioxolan-2-one

A

methanol
67-56-1

methanol

B

Hexane-1,2-diol
6920-22-5

Hexane-1,2-diol

Conditions
ConditionsYield
With [carbonylchlorohydrido{bis[2-(diphenylphosphinomethyl)ethyl]amino}ethylamino] ruthenium(II); potassium tert-butylate; hydrogen In tetrahydrofuran at 140℃; for 4h; Autoclave;A 99 %Chromat.
B 99%
With carbonylhydrido(tetrahydroborato)[bis(2-diphenylphosphinoethyl)-amino]ruthenium(II); potassium carbonate In isopropyl alcohol at 140℃; Glovebox;A > 99 %Chromat.
B 97%
With C23H21MnN2O3P(1+)*Br(1-); potassium tert-butylate; hydrogen In 1,4-dioxane at 140℃; under 37503.8 Torr; for 16h; Autoclave;A 88 %Chromat.
B 96%
4-butyl-2,2-dimethyl-[1,3]dioxolane
93339-59-4

4-butyl-2,2-dimethyl-[1,3]dioxolane

Hexane-1,2-diol
6920-22-5

Hexane-1,2-diol

Conditions
ConditionsYield
With polymer-supported dicyanoketene acetal; water at 20℃; for 2h;96%
With sulfuric acid
4-butyl-1,3-dioxolan-2-one
66675-43-2

4-butyl-1,3-dioxolan-2-one

Hexane-1,2-diol
6920-22-5

Hexane-1,2-diol

Conditions
ConditionsYield
With potassium tert-butylate; hydrogen; C16H18BrCoINO2 In dibutyl ether at 160℃; under 45004.5 Torr; for 20h; Sealed tube; Autoclave;91%
With water; N,N'-dimethylimidazolium-2-carboxylate at 140℃; under 3000.3 Torr; for 6h; Autoclave; Sealed tube;64 %Chromat.
S-methyl 2-hydroxyhexanethioate
61603-70-1

S-methyl 2-hydroxyhexanethioate

Hexane-1,2-diol
6920-22-5

Hexane-1,2-diol

Conditions
ConditionsYield
With lithium aluminium tetrahydride In diethyl ether for 3h; Heating;90%
1,2-Epoxyhexane
1436-34-6

1,2-Epoxyhexane

carbon dioxide
124-38-9

carbon dioxide

aniline
62-53-3

aniline

A

Hexane-1,2-diol
6920-22-5

Hexane-1,2-diol

B

5-butyl-3-phenyl-1,3-oxazolidin-2-one
1174337-23-5

5-butyl-3-phenyl-1,3-oxazolidin-2-one

Conditions
ConditionsYield
With C24H25N4O3(1+)*I(1-); 1,8-diazabicyclo[5.4.0]undec-7-ene at 110℃; under 3750.38 Torr; for 25h; Autoclave;A n/a
B 81%
1-hexene
592-41-6

1-hexene

A

1,2-Epoxyhexane
1436-34-6

1,2-Epoxyhexane

B

Hexane-1,2-diol
6920-22-5

Hexane-1,2-diol

Conditions
ConditionsYield
With poly{[CuMg(pyridine-2,5-dicarboxylate)2(H2O)4]*2H2O}; dihydrogen peroxide In acetonitrile at 60℃; for 24h; Catalytic behavior;A 22%
B 61%
With dihydrogen peroxide; large pore titanium silicate (MCM-41) In methanol at 55.9℃; for 5h; Product distribution; other hydrocarbon; var. oxidation compounds; var. time;
With urea-hydrogen peroxide; tegafur In methanol at 39.85℃; for 12h; Product distribution; Further Variations:; Reagents;
1-aminohexan-2-ol hydrochloride
92447-04-6

1-aminohexan-2-ol hydrochloride

A

Hexane-1,2-diol
6920-22-5

Hexane-1,2-diol

B

n-hexan-2-one
591-78-6

n-hexan-2-one

C

1-acetoxy-2-hexanol
85861-55-8

1-acetoxy-2-hexanol

D

2,5-dibutyl-2-methyl-N-nitroso-oxazolidine
92447-10-4

2,5-dibutyl-2-methyl-N-nitroso-oxazolidine

E

5-butyl-N-nitroso-2-pentyl-oxazolidine
92447-09-1

5-butyl-N-nitroso-2-pentyl-oxazolidine

Conditions
ConditionsYield
With acetic acid; sodium nitrite In water for 48h; Product distribution; pH=6.5; other reagents, other solvent, reagents'molar ratio, different reaction time, other pH value;A 61%
B 17%
C 8%
D n/a
E n/a
methanol
67-56-1

methanol

4-butyl-1,3-dioxolan-2-one
66675-43-2

4-butyl-1,3-dioxolan-2-one

A

Hexane-1,2-diol
6920-22-5

Hexane-1,2-diol

B

carbonic acid dimethyl ester
616-38-6

carbonic acid dimethyl ester

Conditions
ConditionsYield
With MCM-41-pr-TMEDA(+)Cl(-) at 120℃; for 4h;A n/a
B 55%
4-butyl-1,3-dioxolan-2-one
66675-43-2

4-butyl-1,3-dioxolan-2-one

aniline
62-53-3

aniline

A

Hexane-1,2-diol
6920-22-5

Hexane-1,2-diol

B

5-butyl-3-phenyl-1,3-oxazolidin-2-one
1174337-23-5

5-butyl-3-phenyl-1,3-oxazolidin-2-one

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene at 115℃; for 15h;A n/a
B 51%
1,2-Epoxyhexane
1436-34-6

1,2-Epoxyhexane

A

Hexane-1,2-diol
6920-22-5

Hexane-1,2-diol

Conditions
ConditionsYield
Stage #1: 1,2-Epoxyhexane With C57H54CoN3O8 In dichloromethane at 20℃; for 0.25h;
Stage #2: With water In dichloromethane at 20℃; for 12h; Cooling with ice; enantioselective reaction;
A n/a
B 48%
With water In neat (no solvent) at 0 - 20℃; for 6h; Resolution of racemate; enantioselective reaction;A n/a
B 42%
1,2-Epoxyhexane
1436-34-6

1,2-Epoxyhexane

A

Hexane-1,2-diol
6920-22-5

Hexane-1,2-diol

Conditions
ConditionsYield
With water In neat (no solvent) at 0 - 20℃; for 6h; Reagent/catalyst; Resolution of racemate; enantioselective reaction;A n/a
B 42%
cellulose

cellulose

A

propylene glycol
57-55-6

propylene glycol

B

Hexane-1,2-diol
6920-22-5

Hexane-1,2-diol

C

ethylene glycol
107-21-1

ethylene glycol

D

glycerol
56-81-5

glycerol

E

1,2-dihydroxybutane
584-03-2

1,2-dihydroxybutane

Conditions
ConditionsYield
With hydrogen In water at 240℃; for 2h; Autoclave;A 13.5%
B 28.5%
C 5.4%
D 8%
E 10.5%
2-oxohexyl acetate
92675-73-5

2-oxohexyl acetate

A

Hexane-1,2-diol
6920-22-5

Hexane-1,2-diol

B

Acetic acid (S)-1-hydroxymethyl-pentyl ester

Acetic acid (S)-1-hydroxymethyl-pentyl ester

C

(S)-1-acetoxy-2-hexanol

(S)-1-acetoxy-2-hexanol

Conditions
ConditionsYield
With baker's yeast In ethanol; water for 6h; Ambient temperature; Yields of byproduct given;A 28%
B n/a
C n/a
With baker's yeast; L-Cysteine In ethanol; water for 1h; Ambient temperature; Yield given. Yields of byproduct given;
rac-2-hydroxyhexanoic acid
636-36-2, 6064-63-7

rac-2-hydroxyhexanoic acid

Hexane-1,2-diol
6920-22-5

Hexane-1,2-diol

Conditions
ConditionsYield
With lithium aluminium tetrahydride; diethyl ether
1-hydroxyhexan-2-one
73397-68-9

1-hydroxyhexan-2-one

Hexane-1,2-diol
6920-22-5

Hexane-1,2-diol

Conditions
ConditionsYield
Reduktion mit gaerender Hefe;
diethyl ether
60-29-7

diethyl ether

ethyl-2,4-dioxohexanoate
13246-52-1

ethyl-2,4-dioxohexanoate

Hexane-1,2-diol
6920-22-5

Hexane-1,2-diol

Conditions
ConditionsYield
With lithium aluminium tetrahydride
1-acetoxy-2-chloro-hexane
55704-80-8

1-acetoxy-2-chloro-hexane

A

Hexane-1,2-diol
6920-22-5

Hexane-1,2-diol

B

1-amino-2-hydroxy-hexane
72799-62-3, 208850-64-0, 208850-72-0

1-amino-2-hydroxy-hexane

Conditions
ConditionsYield
With ammonium hydroxide
2,3-epoxyhexanol
106498-75-3

2,3-epoxyhexanol

A

Hexane-1,2-diol
6920-22-5

Hexane-1,2-diol

B

1,3-hexanediol
21531-91-9

1,3-hexanediol

Conditions
ConditionsYield
With lithium borohydride In tetrahydrofuran for 2h; Ambient temperature; Yield given. Yields of byproduct given;
(+/-)-1-(hydroxymethyl)pentyl benzoate
128733-29-9

(+/-)-1-(hydroxymethyl)pentyl benzoate

Hexane-1,2-diol
6920-22-5

Hexane-1,2-diol

Conditions
ConditionsYield
With barium dihydroxide In ethanol; water at 85℃; for 3h;
1-(hydroxymethyl)pentyl β-D-galactopyranoside
92447-11-5

1-(hydroxymethyl)pentyl β-D-galactopyranoside

A

D-Galactose
10257-28-0

D-Galactose

B

Hexane-1,2-diol
6920-22-5

Hexane-1,2-diol

Conditions
ConditionsYield
With water at 100℃; for 1h;A 91 % Chromat.
B n/a
1-hexene
592-41-6

1-hexene

A

1,2-Epoxyhexane
1436-34-6

1,2-Epoxyhexane

B

n-hexan-2-ol
626-93-7

n-hexan-2-ol

C

Hexane-1,2-diol
6920-22-5

Hexane-1,2-diol

D

1-hexene-3-ol
4798-44-1

1-hexene-3-ol

E

hexanal
66-25-1

hexanal

F

hexan-1-ol
111-27-3

hexan-1-ol

Conditions
ConditionsYield
With europioum(III) chloride; oxygen; propionic acid; zinc In 1,2-dichloro-ethane at 40℃; for 1h; Product distribution; various catalysts, various solvents, other alkenes;
2-(dimethylphenylsilyl)hexanol

2-(dimethylphenylsilyl)hexanol

Hexane-1,2-diol
6920-22-5

Hexane-1,2-diol

Conditions
ConditionsYield
With peracetic acid; mercury(II) diacetate In acetic anhydride; acetic acid for 3h; Ambient temperature;
2-(Butyl-di-tert-butyl-silanyloxy)-hexan-1-ol
205124-98-7

2-(Butyl-di-tert-butyl-silanyloxy)-hexan-1-ol

Hexane-1,2-diol
6920-22-5

Hexane-1,2-diol

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride In tetrahydrofuran Ambient temperature;
diethyl ether
60-29-7

diethyl ether

ethyl-2,4-dioxohexanoate
13246-52-1

ethyl-2,4-dioxohexanoate

lithium alanate

lithium alanate

Hexane-1,2-diol
6920-22-5

Hexane-1,2-diol

6920-22-5Relevant articles and documents

A METHOD FOR PREPARING 1,2-HEXANEDIOL

-

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.

Chromium-Catalyzed Production of Diols From Olefins

-

Paragraph 0111, (2021/03/19)

Processes for converting an olefin reactant into a diol compound are disclosed, and these processes include the steps of contacting the olefin reactant and a supported chromium catalyst comprising chromium in a hexavalent oxidation state to reduce at least a portion of the supported chromium catalyst to form a reduced chromium catalyst, and hydrolyzing the reduced chromium catalyst to form a reaction product comprising the diol compound. While being contacted, the olefin reactant and the supported chromium catalyst can be irradiated with a light beam at a wavelength in the UV-visible spectrum. Optionally, these processes can further comprise a step of calcining at least a portion of the reduced chromium catalyst to regenerate the supported chromium catalyst.

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