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111-27-3

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111-27-3 Usage

General Description

1-Hexanol, also known as hexyl alcohol, is a six-carbon alcohol with the chemical formula C6H13OH. It is a clear, colorless liquid with a slightly fruity odor and is commonly used as a solvent, and in the production of flavors and perfumes. It is also used as a raw material for the synthesis of various other chemicals, including esters, which are used as flavor and fragrance additives. 1-Hexanol is slightly soluble in water and is flammable, making it important to handle with care. It is also used in the production of plasticizers, and as a precursor to other chemicals like 1-hexyl chloride.

Check Digit Verification of cas no

The CAS Registry Mumber 111-27-3 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,1 and 1 respectively; the second part has 2 digits, 2 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 111-27:
(5*1)+(4*1)+(3*1)+(2*2)+(1*7)=23
23 % 10 = 3
So 111-27-3 is a valid CAS Registry Number.
InChI:InChI=1/C6H14O/c1-2-3-4-5-6-7/h7H,2-6H2,1H3

111-27-3 Well-known Company Product Price

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

  • (A18232)  1-Hexanol, 99%   

  • 111-27-3

  • 500ml

  • 234.0CNY

  • Detail
  • Alfa Aesar

  • (A18232)  1-Hexanol, 99%   

  • 111-27-3

  • 2500ml

  • 546.0CNY

  • Detail
  • Alfa Aesar

  • (31638)  1-Hexanol, 99+%   

  • 111-27-3

  • 4L

  • 2758.0CNY

  • Detail
  • Sigma-Aldrich

  • (471402)  1-Hexanol  anhydrous, ≥99%

  • 111-27-3

  • 471402-100ML

  • 806.13CNY

  • Detail
  • Sigma-Aldrich

  • (471402)  1-Hexanol  anhydrous, ≥99%

  • 111-27-3

  • 471402-1L

  • 1,755.00CNY

  • Detail
  • Sigma-Aldrich

  • (471402)  1-Hexanol  anhydrous, ≥99%

  • 111-27-3

  • 471402-2L

  • 2,523.69CNY

  • Detail
  • Sigma-Aldrich

  • (H13303)  1-Hexanol  reagent grade, 98%

  • 111-27-3

  • H13303-100ML

  • 265.59CNY

  • Detail
  • Sigma-Aldrich

  • (H13303)  1-Hexanol  reagent grade, 98%

  • 111-27-3

  • H13303-1L

  • 515.97CNY

  • Detail
  • Sigma-Aldrich

  • (H13303)  1-Hexanol  reagent grade, 98%

  • 111-27-3

  • H13303-2.5L

  • 936.00CNY

  • Detail
  • Vetec

  • (V900242)  1-Hexanol  Vetec reagent grade, 98%

  • 111-27-3

  • V900242-500ML

  • 184.86CNY

  • Detail
  • Sigma-Aldrich

  • (52828)  1-Hexanol  ReagentPlus®, ≥99.5% (GC)

  • 111-27-3

  • 52828-5ML

  • 1,104.48CNY

  • Detail
  • Sigma-Aldrich

  • (52828)  1-Hexanol  ReagentPlus®, ≥99.5% (GC)

  • 111-27-3

  • 52828-25ML

  • 4,079.79CNY

  • Detail

111-27-3SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name hexan-1-ol

1.2 Other means of identification

Product number -
Other names n-C6H13OH

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Food additives -> Flavoring Agents
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:111-27-3 SDS

111-27-3Synthetic route

Ethyl hexanoate
123-66-0

Ethyl hexanoate

hexan-1-ol
111-27-3

hexan-1-ol

Conditions
ConditionsYield
With sodium aluminum tetrahydride In tetrahydrofuran at 0℃; for 0.5h;100%
With C30H34Cl2N2P2Ru; potassium methanolate; hydrogen In tetrahydrofuran at 100℃; under 38002.6 - 76005.1 Torr; for 15h; Glovebox; Autoclave;93%
With ethanol; ruthenium(bis[2‐(ethylsulfanyl)ethyl]amine)(dichloro)(triphenylphosphine); potassium tert-butylate In toluene at 80℃; for 16h; Catalytic behavior; Reagent/catalyst;89%
hexanal
66-25-1

hexanal

hexan-1-ol
111-27-3

hexan-1-ol

Conditions
ConditionsYield
With Na-phosphate buffer; horse liver NADH; NAD; sodium formate; <(C5Me5)Rh(bpy-5-OAc)(H2O)>Cl2 at 25℃; for 30h; Product distribution; Mechanism; other ketones, other times, other temperatures, other enzymes;100%
With sodium aluminum tetrahydride In tetrahydrofuran at 0℃; for 0.0833333h; Product distribution; other aldehydes, ketones, carboxylic acids (also sodium salts), acid chlorides, esters, lactones, epoxides, amides, nitriles, nitrogen and sulfur compounds; var. temp., time and ratio of reagents;100%
With sodium aluminum tetrahydride In tetrahydrofuran at 0℃; for 0.0833333h;100%
methyl hexanoate
106-70-7

methyl hexanoate

hexan-1-ol
111-27-3

hexan-1-ol

Conditions
ConditionsYield
With C39H39N6ORu(1+)*Br(1-); potassium methanolate; hydrogen In tetrahydrofuran at 70℃; under 37503.8 Torr; for 4h; Reagent/catalyst;100%
With C56H70Cl3N10Ru2(1+)*F6P(1-); potassium tert-butylate; hydrogen In tetrahydrofuran; dodecane at 70℃; under 37503.8 Torr; for 16h; Inert atmosphere; Glovebox; Autoclave;100%
With C30H26Cl2N3PRu; hydrogen; sodium ethanolate In toluene at 80℃; under 38002.6 Torr; for 16h; Catalytic behavior; Autoclave; Inert atmosphere; Schlenk technique;95%
2,4,6-triisopropyl-benzenesulfonic acid n-hexylester
82965-03-5

2,4,6-triisopropyl-benzenesulfonic acid n-hexylester

A

1,3,5-triisopropyl benzene
717-74-8

1,3,5-triisopropyl benzene

B

hexan-1-ol
111-27-3

hexan-1-ol

Conditions
ConditionsYield
With lithium amalgam In N,N-dimethyl-formamide; toluene Product distribution; Mechanism; further solvents;A 100%
B 100%
n-hexyl caproate
6378-65-0

n-hexyl caproate

hexan-1-ol
111-27-3

hexan-1-ol

Conditions
ConditionsYield
With C56H70Cl3N10Ru2(1+)*F6P(1-); potassium tert-butylate; hydrogen In tetrahydrofuran; dodecane at 70℃; under 37503.8 Torr; for 16h; Inert atmosphere; Glovebox; Autoclave;100%
With C66H102N4OP2Ru; hydrogen In toluene at 105℃; under 22502.3 Torr; for 20h; Inert atmosphere; Glovebox;99%
With C31H26ClN2OPRu; hydrogen; sodium methylate In tetrahydrofuran at 80℃; for 2h;98%
propyl hexanoate
626-77-7

propyl hexanoate

hexan-1-ol
111-27-3

hexan-1-ol

Conditions
ConditionsYield
With C56H70Cl3N10Ru2(1+)*F6P(1-); potassium tert-butylate; hydrogen In tetrahydrofuran; dodecane at 70℃; under 37503.8 Torr; for 16h; Inert atmosphere; Glovebox; Autoclave;100%
2-hexyloxy-tetrahydro-pyran
1927-63-5

2-hexyloxy-tetrahydro-pyran

hexan-1-ol
111-27-3

hexan-1-ol

Conditions
ConditionsYield
silica-supported prop-1-ylsulfonic acid In methanol99.6%
With silica gel; iron(III) chloride for 45h; Ambient temperature;98.5%
ammonium cerium(IV) nitrate In alkaline aq. solution; acetonitrile at 70℃; for 2h; pH=8; Decomposition;94%
1-hexene
592-41-6

1-hexene

hexan-1-ol
111-27-3

hexan-1-ol

Conditions
ConditionsYield
Stage #1: 1-hexene With 9-bora-bicyclo[3.3.1]nonane
Stage #2: With sodium peroxoborate tetrahydrate
99%
Stage #1: 1-hexene With borane-THF In tetrahydrofuran at 25℃; for 0.0138889h; Flow reactor;
Stage #2: With dihydrogen peroxide; sodium hydroxide In tetrahydrofuran; ethanol; water at 20℃; for 0.00555556h; Flow reactor;
88%
With di-n-pentylbromoborane; alkaline H2O2; sodium hydride 1.) diglyme, room temperature, 7 h; further dialkylbromoboranes; Yield given. Multistep reaction;
hexyl 2,4,6-trimethylbenzenesulfonate
82965-02-4

hexyl 2,4,6-trimethylbenzenesulfonate

A

1,3,5-trimethyl-benzene
108-67-8

1,3,5-trimethyl-benzene

B

hexan-1-ol
111-27-3

hexan-1-ol

Conditions
ConditionsYield
With lithium amalgam In N,N-dimethyl-formamide; toluene Product distribution; Mechanism; further solvents;A 85%
B 99%
3-hexyn-1-ol
1002-28-4

3-hexyn-1-ol

A

(Z)-3-Hexen-1-ol
928-96-1

(Z)-3-Hexen-1-ol

B

hexan-1-ol
111-27-3

hexan-1-ol

Conditions
ConditionsYield
With hydrogen; copper-palladium; silica gel In ethanol at 25℃; under 760 Torr; Kinetics;A 99%
B n/a
With hydrogen In methanol at 30℃; under 760.051 Torr; for 3h;A 99%
B 1%
With hydrogen In methanol at 20℃; under 150.015 - 900.09 Torr; for 0.0116667h; Inert atmosphere; Schlenk technique; Green chemistry;A n/a
B n/a
hexanoic acid
142-62-1

hexanoic acid

hexan-1-ol
111-27-3

hexan-1-ol

Conditions
ConditionsYield
With water In aq. phosphate buffer at 20℃; pH=7.4; Electrolysis; Inert atmosphere; Enzymatic reaction;98.3%
With hydrogen; Rh/Al2O3; molybdenum hexacarbonyl In 1,2-dimethoxyethane at 150℃; under 76000 Torr; for 16h;95%
With 1,1,3,3-Tetramethyldisiloxane; copper(II) bis(trifluoromethanesulfonate) In toluene at 80℃; for 16h; sealed tube;94%
Caproamide
628-02-4

Caproamide

hexan-1-ol
111-27-3

hexan-1-ol

Conditions
ConditionsYield
With C24H20ClN2OPRu; potassium tert-butylate; hydrogen In tetrahydrofuran at 110℃; under 10640.7 Torr; for 36h; Inert atmosphere; Schlenk technique;98%
With ethanol; sodium
With sodium aluminum tetrahydride In tetrahydrofuran for 12h; Ambient temperature;
benzenesulfonic acid n-hexylester
781-07-7

benzenesulfonic acid n-hexylester

A

Benzenesulfinic acid
618-41-7

Benzenesulfinic acid

B

hexan-1-ol
111-27-3

hexan-1-ol

Conditions
ConditionsYield
With lithium amalgam In 1,4-dioxane; isopropyl alcohol at 23℃; for 2h;A 98%
B 98%
2-hexenal
505-57-7

2-hexenal

hexan-1-ol
111-27-3

hexan-1-ol

Conditions
ConditionsYield
With sodium tetrahydroborate; palladium diacetate In methanol at 20℃; for 0.5h;98%
hex-2-yn-1-ol
764-60-3

hex-2-yn-1-ol

A

(Z)-2-hexen-1-ol
928-94-9

(Z)-2-hexen-1-ol

B

hexan-1-ol
111-27-3

hexan-1-ol

Conditions
ConditionsYield
With hydrogen In tetrahydrofuran at 30℃; under 760.051 Torr; for 6h;A 98%
B 2%
2-Ethylhexanoic acid
149-57-5

2-Ethylhexanoic acid

1-Chlorohexane
544-10-5

1-Chlorohexane

hexan-1-ol
111-27-3

hexan-1-ol

Conditions
ConditionsYield
In sodium hydroxide; water97%
1-(2-Thioxo-thiazolidin-3-yl)-hexan-1-one
74058-62-1

1-(2-Thioxo-thiazolidin-3-yl)-hexan-1-one

hexan-1-ol
111-27-3

hexan-1-ol

Conditions
ConditionsYield
With sodium tetrahydroborate; water In tetrahydrofuran Ambient temperature;96%
benzenesulfonic acid n-hexylester
781-07-7

benzenesulfonic acid n-hexylester

A

lithium benzenesulfinate
16883-74-2

lithium benzenesulfinate

B

hexan-1-ol
111-27-3

hexan-1-ol

Conditions
ConditionsYield
With lithium amalgam In N,N-dimethyl-formamide; toluene at 23℃; for 2h; Product distribution; Mechanism; further solvents (effect of pKa);A 95%
B 95%
4-methylbenzenesulfonic acid n-hexylester
3839-35-8

4-methylbenzenesulfonic acid n-hexylester

A

p-toluene sulfinic acid
536-57-2

p-toluene sulfinic acid

B

hexan-1-ol
111-27-3

hexan-1-ol

Conditions
ConditionsYield
With lithium amalgam In 1,4-dioxane; isopropyl alcohol at 23℃; for 2h;A 95%
B 95%
4-chlorobenzenesulfonic acid n-hexylester
69564-60-9

4-chlorobenzenesulfonic acid n-hexylester

A

4-chlorobenzenesulfinic acid
100-03-8

4-chlorobenzenesulfinic acid

B

hexan-1-ol
111-27-3

hexan-1-ol

Conditions
ConditionsYield
With lithium amalgam In 1,4-dioxane; isopropyl alcohol at 23℃; for 2h;A 91%
B 95%
hexyl 2-propenyl ether
3295-94-1

hexyl 2-propenyl ether

hexan-1-ol
111-27-3

hexan-1-ol

Conditions
ConditionsYield
With aniline; (ϖ-allyl)palladium triflate based catalyst at 50℃; for 2h;94%
With lithium aluminium tetrahydride; bis(cyclopentadienyl)titanium dichloride In tetrahydrofuran for 8h; Ambient temperature;84%
tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; polydimethylsiloxane In methanol; water at 50℃; for 24h;77%
2-hexen-1-ol
2305-21-7

2-hexen-1-ol

hexan-1-ol
111-27-3

hexan-1-ol

Conditions
ConditionsYield
Stage #1: 2-hexen-1-ol With lithium triethylborohydride; cobalt(II) bromide In tetrahydrofuran Inert atmosphere; Glovebox;
Stage #2: With hydrogen In tetrahydrofuran at 60℃; under 7500.75 Torr; for 3h;
94%
1-hexene
592-41-6

1-hexene

A

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

n-hexan-2-ol

B

hexan-1-ol
111-27-3

hexan-1-ol

Conditions
ConditionsYield
Stage #1: 1-hexene With Thexylboran
Stage #2: With sodium peroxoborate tetrahydrate
A n/a
B 93%
With borane-THF; dihydrogen peroxide; sodium carbonate 1.) THF, 0 deg C; 2.) H2O/THF, 50 deg C, 1 h; Yield given. Multistep reaction. Yields of byproduct given;
With dimesitylboron hydride In tetrahydrofuran at 25℃; for 8h; Yields of byproduct given. Title compound not separated from byproducts;A n/a
B 96 % Chromat.
4-methoxybenzenesulfonic acid n-hexylester
69564-56-3

4-methoxybenzenesulfonic acid n-hexylester

A

4-methoxybenzenesulfinic acid
1709-60-0

4-methoxybenzenesulfinic acid

B

hexan-1-ol
111-27-3

hexan-1-ol

Conditions
ConditionsYield
With lithium amalgam In N,N-dimethyl-formamide at 23℃; for 2h;A 93%
B 90%
1-(tert-butyldimethylsilyl)oxyhexane
80033-60-9

1-(tert-butyldimethylsilyl)oxyhexane

hexan-1-ol
111-27-3

hexan-1-ol

Conditions
ConditionsYield
With diisobutylaluminium hydride In dichloromethane; toluene at 23℃; for 2h;93%
hexan-1-amine
111-26-2

hexan-1-amine

hexan-1-ol
111-27-3

hexan-1-ol

Conditions
ConditionsYield
With carbonylchloro[4,5-bis(diisopropylphosphinomethyl)acridine]hydridoruthenium(II); water; hydrogen In 1,4-dioxane at 135℃; under 3750.38 Torr; for 48h; Pressure; Schlenk technique; Inert atmosphere;93%
2,4-hexadiene-1-ol
111-28-4

2,4-hexadiene-1-ol

A

(Z)-3-Hexen-1-ol
928-96-1

(Z)-3-Hexen-1-ol

B

(E)-3-hexen-1-ol
928-97-2

(E)-3-hexen-1-ol

D

hexan-1-ol
111-27-3

hexan-1-ol

Conditions
ConditionsYield
With hydrogen; (methyl benzoate)Cr(CO)6 In methanol at 190 - 200℃; under 36775.4 Torr; for 2h;A 92.5%
B 4.6%
C 2.3%
D 0.6%
With hydrogen; (1,2,4,5-tetramethylbenzene)tricarbonylchromium(0) In methanol at 190 - 200℃; under 36775.4 Torr; for 4h; Product distribution; other arene ligands, other solvents; also in absence of arene ligands;
hexahydro-2H-oxepin-2-one
502-44-3

hexahydro-2H-oxepin-2-one

A

1,6-hexanediol
629-11-8

1,6-hexanediol

B

hexan-1-ol
111-27-3

hexan-1-ol

Conditions
ConditionsYield
With hydrogen In 1,2-dimethoxyethane at 80℃; under 60006 Torr; for 2h; Reagent/catalyst; Pressure; Solvent; Temperature;A 92.3%
B 8%
With hydrogen; (acetylacetonato)dicarbonylrhodium (l); molybdenum hexacarbonyl In 1,4-dioxane at 150℃; under 75007.5 Torr; for 3h;A 79%
B 7%
5-Hexen-1-ol
821-41-0

5-Hexen-1-ol

hexan-1-ol
111-27-3

hexan-1-ol

Conditions
ConditionsYield
With Na12(Ga4(1,5-bis(2,3-dihydroxybenzamido)naphthalene))6; [(DMPE)Rh(COD)][BF4]; hydrogen In water-d2 at 20℃; for 12h; Reagent/catalyst;92%
phthalic anhydride
85-44-9

phthalic anhydride

hexan-1-ol
111-27-3

hexan-1-ol

mono-n-hexyl phthalate
24539-57-9

mono-n-hexyl phthalate

Conditions
ConditionsYield
at 20 - 50℃; for 1h; Temperature;100%
at 100 - 110℃;
at 20 - 135℃;
methanesulfonyl chloride
124-63-0

methanesulfonyl chloride

hexan-1-ol
111-27-3

hexan-1-ol

n-hexyl methanesulfonate
16156-50-6

n-hexyl methanesulfonate

Conditions
ConditionsYield
With triethylamine In dichloromethane at -15℃; for 1h; Green chemistry;100%
With triethylamine99%
With triethylamine In dichloromethane at 0 - 20℃;99%
aniline
62-53-3

aniline

hexan-1-ol
111-27-3

hexan-1-ol

N-hexylaniline
4746-32-1

N-hexylaniline

Conditions
ConditionsYield
With C19H35Cl2CoN2P; sodium triethylborohydride In toluene at 150℃; for 24h;100%
With chloro(η5-pentamethylcyclopentadienyl)(L-prolinato)iridium(III) In toluene at 95℃; for 24h; Inert atmosphere; Sealed tube;98%
With chloro(η5-pentamethylcyclopentadienyl)(L-prolinato)iridium(III) In toluene at 95℃; for 24h;98%
vinyl acetate
108-05-4

vinyl acetate

hexan-1-ol
111-27-3

hexan-1-ol

1-hexyl acetate
142-92-7

1-hexyl acetate

Conditions
ConditionsYield
With dilithium tetra(tert-butyl)zincate In toluene at 0℃; for 1h; Inert atmosphere;100%
With pseudomonas fuorescens lipase immobilized on multiwall carbon nano-tubes at 50℃; for 5h; Green chemistry;99%
With sulfuric acid beim Erhitzen;
With aluminium trichloride at 105℃;
In diethyl ether at 35℃; Candida cylindracea lipase;
hexan-1-ol
111-27-3

hexan-1-ol

n-hexyl caproate
6378-65-0

n-hexyl caproate

Conditions
ConditionsYield
With C23H42N2OP2Ru for 12h; Reflux; Inert atmosphere; Darkness;100%
Ru complex at 157℃; for 24h; Inert atmosphere;99%
With calcium hypochlorite In water; acetic acid; acetonitrile at 0℃; for 1h;98%
hexan-1-ol
111-27-3

hexan-1-ol

hexanal
66-25-1

hexanal

Conditions
ConditionsYield
With 4 A molecular sieve; tetrabutylammonium periodite; sodium ruthenate(VI) In dichloromethane at 20℃; for 24h; Oxidation;100%
With 4 A molecular sieve; tetrabutylammonium perchlorate; Ru-Cu-Al-hydrotalcite In toluene at 60℃; for 24h;100%
With iodosylbenzene; Cl-CH2-PS supported 5-amino-1,10-phenanthroline-Ru In acetonitrile at 60℃; for 2h;100%
hexan-1-ol
111-27-3

hexan-1-ol

hexanoic acid
142-62-1

hexanoic acid

Conditions
ConditionsYield
With air; potassium carbonate In water at 66.84℃; for 24h;100%
With oxygen In water at 80℃; under 760.051 Torr; for 24h;99.3%
Stage #1: hexan-1-ol With gold on titanium oxide In water at 90℃; for 0.166667h; Inert atmosphere;
Stage #2: With dihydrogen peroxide In water at 90℃; for 1.08333h; Inert atmosphere; chemoselective reaction;
99%
3-tert-butoxycarbonyl-2-chloro-1,3,2-oxazaphospholidine
148160-26-3

3-tert-butoxycarbonyl-2-chloro-1,3,2-oxazaphospholidine

hexan-1-ol
111-27-3

hexan-1-ol

3-tert-butoxycarbonyl-2-hexyloxy-1,3,2-oxazaphospholidine
148160-27-4

3-tert-butoxycarbonyl-2-hexyloxy-1,3,2-oxazaphospholidine

Conditions
ConditionsYield
With triethylamine In dichloromethane -60 deg C to r.t., 1 h;100%
Propiolic acid
471-25-0

Propiolic acid

hexan-1-ol
111-27-3

hexan-1-ol

acetylene carboxylic acid n-hexyl ester
68279-21-0

acetylene carboxylic acid n-hexyl ester

Conditions
ConditionsYield
With toluene-4-sulfonic acid In benzene100%
toluene-4-sulfonic acid In toluene for 18h; Heating / reflux;96%
With toluene-4-sulfonic acid84%
With toluene-4-sulfonic acid In benzene for 16h; Heating;84%
Glp-Glu-Pro-NH2

Glp-Glu-Pro-NH2

hexan-1-ol
111-27-3

hexan-1-ol

(S)-5-((S)-2-Carbamoyl-pyrrolidin-1-yl)-5-oxo-4-[((S)-5-oxo-pyrrolidine-2-carbonyl)-amino]-pentanoic acid hexyl ester

(S)-5-((S)-2-Carbamoyl-pyrrolidin-1-yl)-5-oxo-4-[((S)-5-oxo-pyrrolidine-2-carbonyl)-amino]-pentanoic acid hexyl ester

Conditions
ConditionsYield
With polyvinylpyridine polymer-supported dimethylaminopyridine; polystyrene-bound N-cyclohexylcarbodiimide In dichloromethane at 20℃;100%
1-Phenyl-1H-tetrazole-5-thiol
86-93-1

1-Phenyl-1H-tetrazole-5-thiol

hexan-1-ol
111-27-3

hexan-1-ol

5-hexylthio-1-phenyl-1H-tetrazole

5-hexylthio-1-phenyl-1H-tetrazole

Conditions
ConditionsYield
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran; toluene at 0 - 20℃; for 0.5h; Inert atmosphere;100%
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 20℃; for 1h;95%
ortho-nitrofluorobenzene
1493-27-2

ortho-nitrofluorobenzene

hexan-1-ol
111-27-3

hexan-1-ol

1-(hexyloxy)-2-nitrobenzene
67285-54-5

1-(hexyloxy)-2-nitrobenzene

Conditions
ConditionsYield
With triethylsilane; t-Bu-P4 In hexane; dimethyl sulfoxide at 100℃; for 2h;100%
3-(triethoxypropyl) isocyanate
24801-88-5

3-(triethoxypropyl) isocyanate

hexan-1-ol
111-27-3

hexan-1-ol

C16H35NO5Si

C16H35NO5Si

Conditions
ConditionsYield
at 85℃; for 24h;100%
4-[(6,7-dimethoxy-4-quinolyl)oxy]-2,5-dimethylaniline
286371-46-8

4-[(6,7-dimethoxy-4-quinolyl)oxy]-2,5-dimethylaniline

bis(trichloromethyl) carbonate
32315-10-9

bis(trichloromethyl) carbonate

sodium hydrogencarbonate
144-55-8

sodium hydrogencarbonate

hexan-1-ol
111-27-3

hexan-1-ol

hexyl N-{4-[(6,7-dimethoxy-4-quinolyl)oxy]-2,5-dimethylphenyl}carbamate

hexyl N-{4-[(6,7-dimethoxy-4-quinolyl)oxy]-2,5-dimethylphenyl}carbamate

Conditions
ConditionsYield
With triethylamine In methanol; dichloromethane; chloroform; toluene100%
diisopropyl-carbodiimide
693-13-0

diisopropyl-carbodiimide

hexan-1-ol
111-27-3

hexan-1-ol

C13H28N2O
123196-37-2

C13H28N2O

Conditions
ConditionsYield
With copper(II) bis(trifluoromethanesulfonate) at 100℃; for 0.0833333h; Microwave irradiation;100%
hexan-1-ol
111-27-3

hexan-1-ol

heptanal
111-71-7

heptanal

Conditions
ConditionsYield
With oxidase In water at 40℃; for 1.5h; Reformatsky Reaction;100%
With oxygen In neat (no solvent) at 45℃; for 7h; Solvent; Temperature;50 %Chromat.
β-naphthol
135-19-3

β-naphthol

hexan-1-ol
111-27-3

hexan-1-ol

2-(n-hexyloxy)naphthalene
31059-20-8

2-(n-hexyloxy)naphthalene

Conditions
ConditionsYield
With bismuth(lll) trifluoromethanesulfonate In 1,2-dichloro-ethane at 80℃; for 24h; Reagent/catalyst; Inert atmosphere; Schlenk technique; chemoselective reaction;100%
With toluene-4-sulfonic acid In neat (no solvent) at 120℃; for 24h; Inert atmosphere; Sealed tube;98%
With p-toluene sulfonic acid - choline chloride covalently immobilized on polymeric microspheres coated iron oxide magnetic nanoparticles In neat (no solvent) at 120℃; for 12h; Reagent/catalyst; Solvent; chemoselective reaction;90%
6-ethyl-2-naphthol
1999-64-0

6-ethyl-2-naphthol

hexan-1-ol
111-27-3

hexan-1-ol

6-ethyl-2-hexyloxynaphthalene

6-ethyl-2-hexyloxynaphthalene

Conditions
ConditionsYield
With bismuth(lll) trifluoromethanesulfonate In 1,2-dichloro-ethane at 80℃; for 24h; Inert atmosphere; Schlenk technique; chemoselective reaction;100%
4,4'-((pentane-1,5-diylbis(oxy))bis(4,1-phenylene))bis(dihydro-2H-pyran-2,6(3H)-dione)

4,4'-((pentane-1,5-diylbis(oxy))bis(4,1-phenylene))bis(dihydro-2H-pyran-2,6(3H)-dione)

hexan-1-ol
111-27-3

hexan-1-ol

3,3'-((pentane-1,5-diylbis(oxy))bis(4,1-phenylene))bis(5-(hexyloxy)-5-oxopentanoic acid)

3,3'-((pentane-1,5-diylbis(oxy))bis(4,1-phenylene))bis(5-(hexyloxy)-5-oxopentanoic acid)

Conditions
ConditionsYield
With C28H27F6N3O3S In tetrahydrofuran at 25℃; for 72h; Inert atmosphere;100%
4-cyanophenol
767-00-0

4-cyanophenol

hexan-1-ol
111-27-3

hexan-1-ol

1-(4-cyanophenyl)oxyhexane
66052-06-0

1-(4-cyanophenyl)oxyhexane

Conditions
ConditionsYield
With nickel(II) sulfate hexahydrate; 4,4'-Dimethoxy-2,2'-bipyridin; C41H40O16; N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 24h; Schlenk technique; Irradiation; Inert atmosphere;100%
3,4-dihydro-2H-pyran
110-87-2

3,4-dihydro-2H-pyran

hexan-1-ol
111-27-3

hexan-1-ol

2-hexyloxy-tetrahydro-pyran
1927-63-5

2-hexyloxy-tetrahydro-pyran

Conditions
ConditionsYield
silica-supported prop-1-ylsulfonic acid In acetonitrile for 0.166667h;99.8%
With sulfated zirconia In dichloromethane for 1h; Ambient temperature;96%
With aminosulfonic acid at 15℃; for 4.5h;96%
acetic anhydride
108-24-7

acetic anhydride

hexan-1-ol
111-27-3

hexan-1-ol

1-hexyl acetate
142-92-7

1-hexyl acetate

Conditions
ConditionsYield
With sodium hydroxide for 0.0194444h; microwave irradiation;99%
With H3[P(Mo3O10)4]*nH2O at 20℃; for 0.1h;97%
With zirconium phosphate In neat (no solvent) at 60℃; for 0.5h; Green chemistry;96%
1,2-diamino-benzene
95-54-5

1,2-diamino-benzene

hexan-1-ol
111-27-3

hexan-1-ol

2-pentyl-1H-benzoimidazole
5851-46-7

2-pentyl-1H-benzoimidazole

Conditions
ConditionsYield
With C19H35Cl2CoN2P; sodium triethylborohydride In toluene at 150℃; for 24h; Catalytic behavior; Reagent/catalyst; Solvent; Temperature; Molecular sieve; Schlenk technique;99%
With C15H15ClN7Ru(1+)*Cl(1-); sodium tetraphenyl borate; 1,2-bis-(diphenylphosphino)ethane at 165℃; for 12h; Reagent/catalyst; Schlenk technique; Inert atmosphere;98%
With [Py(NP(iPr)2)(NHP(iPr)2)Ir(cod)]; potassium tert-butylate In diethylene glycol dimethyl ether at 110℃; for 24h; Inert atmosphere;95%

111-27-3Related news

Kinetics of 1-Hexanol (cas 111-27-3) etherification on Amberlyst 7008/26/2019

The kinetics of the liquid-phase etherification of 1-hexanol to di-n-ethyl ether and water on the ion-exchange resin Amberlyst 70 in the temperature range 423–463 K is studied. The strong inhibition effect of water is considered following two approaches. First, a model stemming from a Langmuir–...detailed

Pressure dependence of the solubility of light fullerenes in 1-Hexanol (cas 111-27-3) from 298.15 K to 363.15 K08/25/2019

The solubility of light fullerenes (C60 and C70) in 1-hexanol was investigated in the range of pressures of 0.1–100 MPa and in the range of temperatures of 298.15–363.15 K. In all of the studied temperatures, solubility increases monotonously with increasing pressure. At ambient pressure, we h...detailed

Association of 1-Hexanol (cas 111-27-3) in mixtures with n-hexane: Dielectric, near-infrared and DFT studies08/21/2019

Association of 1-hexanol in n-hexane has been studied by measurements of nonlinear dielectric effect (NDE) and near-infrared (NIR) spectroscopy. Besides, the dipole moments of selected open and cyclic associates were determined by DFT (density functional theory) calculations. All measurements we...detailed

1-Hexanol (cas 111-27-3) conformers in a nitrogen matrix: FTIR study and high-level ab initio calculations08/20/2019

FTIR spectra of 1-hexanol trapped in a nitrogen matrix were registered in the temperature range from 10 to 40 K. The experiment has shown that only non‑hydrogen-bonded alcohol molecules were present in the sample at 10 K. Conformational analysis using high-level ROCBS-QB3 ab-initio calculations ...detailed

111-27-3Relevant articles and documents

Brown,H.C.,Kulkarni,S.U.

, p. 4169 - 4170 (1977)

Highly Efficient Photocatalytic Degradation of Dyes by a Copper–Triazolate Metal–Organic Framework

Liu, Chen-Xia,Zhang, Wen-Hua,Wang, Nan,Guo, Penghu,Muhler, Martin,Wang, Yuemin,Lin, Shiru,Chen, Zhongfang,Yang, Guang

, p. 16804 - 16813 (2018)

A copper(I) 3,5-diphenyltriazolate metal–organic framework (CuTz-1) was synthesized and extensively characterized by using a multi-technique approach. The combined results provided solid evidence that CuTz-1 features an unprecedented Cu5tz6 cluster as the secondary building unit (SBU) with channels approximately 8.3 ? in diameter. This metal–organic framework (MOF) material, which is both thermally and chemically (basic and acidic) stable, exhibited semiconductivity and high photocatalytic activity towards the degradation of dyes in the presence of H2O2. Its catalytic performance was superior to that of reported MOFs and comparable to some composites, which has been attributed to its high efficiency in generating .OH, the most active species for the degradation of dyes. It is suggested that the photogenerated holes are trapped by CuI, which yields CuII, the latter of which behaves as a catalyst for a Fenton-like reaction to produce an excess amount of .OH in addition to that formed through the scavenging of photogenerated electrons by H2O2. Furthermore, it was shown that a dye mixture (methyl orange, methyl blue, methylene blue, and rhodamine B) could be totally decolorized by using CuTz-1 as a photocatalyst in the presence of H2O2 under the irradiation of a Xe lamp or natural sunlight.

New selectivities from old catalysts. Occlusion of Grubbs' catalysts in PDMS to change their reactions

Brett Runge,Mwangi, Martin T.,Bowden, Ned B.

, p. 5278 - 5288 (2006)

This article describes new selectivities for Grubbs' first and second generation catalysts when occluded in a hydrophobic matrix of polydimethylsiloxane (PDMS). Occlusion of catalysts in mm-sized slabs of PDMS is accomplished by swelling with methylene chloride then removing the solvent under vacuum. The catalysts are homogenously dissolved in PDMS yet remain catalytically active. Many substrates that react by olefin metathesis with Grubbs' catalysts freely dissolved in methylene chloride also react by olefin isomerization with occluded catalysts. Eleven examples of substrates that exhibit dual reactivity by undergoing olefin isomerization with occluded catalysts and olefin metathesis with catalysts dissolved in methylene chloride are reported. Most of these substrates have olefins with allylic phosphine oxides, carbonyls, or ethers. Control experiments demonstrate that isomerization is occurring in the solvent by decomposition of the catalyst from a ruthenium carbene to a proposed ruthenium hydride. This work was extended by heating occluded Grubbs' first generation catalyst to 100 °C in 90% MeOH in H2O in the presence of various alkenes to transform the Grubbs' catalyst into an isomerization catalyst for unfunctionalized olefins. This work demonstrates that occlusion of organometallic catalysts in PDMS has important implications for their reactions and can be used as a method to control which reactions they catalyze.

Mechanistic study of the selective hydrogenation of carboxylic acid derivatives over supported rhenium catalysts

Toyao, Takashi,Ting, Kah Wei,Siddiki, S. M. A. Hakim,Touchy, Abeda S.,Onodera, Wataru,Maeno, Zen,Ariga-Miwa, Hiroko,Kanda, Yasuharu,Asakura, Kiyotaka,Shimizu, Ken-ichi

, p. 5413 - 5424 (2019)

The structure and performance of TiO2-supported Re (Re/TiO2) catalysts for selective hydrogenation of carboxylic acid derivatives have been investigated. Re/TiO2 promotes selective hydrogenation reactions of carboxylic acids and esters that form the corresponding alcohols, and of amides that generate the corresponding amines. These processes are not accompanied by reduction of aromatic moieties. A Re loading amount of 5 wt% and a catalyst pretreatment with H2 at 500 °C were identified as being optimal to obtain the highest catalytic activity for the hydrogenation processes. The results of studies using various characterization methods, including X-ray diffraction (XRD), X-ray absorption fine structure (XAFS), X-ray photoelectron spectroscopy (XPS), and scanning transmission electron microscopy (STEM), indicate that the Re species responsible for the catalytic hydrogenation processes have sub-nanometer to a few nanometer sizes and average oxidation states higher than 0 and below +4. The presence of either a carboxylic acid and/or its corresponding alcohol is critical for preventing the Re/TiO2 catalyst from promoting production of dearomatized byproducts. Although Re/TiO2 is intrinsically capable of hydrogenating aromatic rings, carboxylic acids, alcohols, amides, and amines strongly adsorb on the Re species, which leads to suppression of this process. Moreover, the developed catalytic system was applied to selective hydrogenation of triglycerides that form the corresponding alcohols.

LiBH4-promoted Hydroboration of Alkenes with 1,3,2-Benzodioxaborole

Arase, Akira,Nunokawa, Yutaka,Masuda, Yuzuru,Hoshi, Masayuki

, p. 205 - 206 (1991)

In the presence of a small amount of LiBH4 mono-, di-, tri- and tetr-substituted ethenes were hydroborated almost quantitatively with 1,3,2-benzodioxaborole (catecholborane) under very mild conditions.

Catalytic conversion of ethanol into an advanced biofuel: Unprecedented selectivity for n-butanol

Dowson, George R. M.,Haddow, Mairi F.,Lee, Jason,Wingad, Richard L.,Wass, Duncan F.

, p. 9005 - 9008 (2013)

Taming the beast: Unprecedented selectivity of over 94 % at good (20 %+) conversion was observed for the upgrade of ethanol to the advanced biofuel 1-butanol with a ruthenium diphosphine catalyst (see picture; P orange, Ru blue). Preliminary mechanistic studies indicate that control over the notoriously uncontrolled acetaldehyde aldol condensation is critical for the high selectivity, and evidence was found for an on-metal condensation step. Copyright

Revised Mechanisms of the Catalytic Alcohol Dehydrogenation and Ester Reduction with the Milstein PNN Complex of Ruthenium

Gusev, Dmitry G.

, (2020)

The combined experimental/DFT computational study of RuH2(CO)[Et2NCH2PyCH2Pt-Bu2] (2) suggests that this dihydride is the catalyst of the acceptorless alcohol dehydrogenation and ester hydrogenation reactions developed in the group of Milstein, whereas the corresponding alkoxide RuH(OR)(CO)[Et2NCH2PyCH2Pt-Bu2] (4) is an important reaction intermediate. A relatively fast equilibrium of dihydride 2 and ethanol with ethoxide 4 and H2 was demonstrated by NMR experiments, as well as the proton exchanges occurring between the OH of ethanol, RuH, and the CH2 groups of the PNN ligand backbone of 2 and 4. A detailed critical discussion of the previously proposed mechanisms with the Milstein catalyst is presented. This paper also reports the preparation of the osmium dihydride OsH2(CO)[Et2NCH2PyCH2Pt-Bu2] (2-Os) and a comparative study of 2, 2-Os, and the Noyori-type osmium catalyst OsH2(CO)[PyCH2NHCH2CH2NHPt-Bu2].

A new route of the reaction of EtAlCl2 with α-olefins catalyzed by Ti complexes

Ibragimov,Khafizova,Zagrebel'naya,Parfenova,Sultanov,Khalilov,Dzkemilev

, p. 292 - 296 (2001)

A new method for the synthesis of dialkyl(ethyl)alanes by the reaction of EtAlCl2 with α-olefins in the presence of Mg and a catalytic amount of Cp2TiCl2 (Ti(OPri)4, Ti(OBun)4) in THF was developed.

-

Hurd,McNamee

, (1937)

-

Enzymes inhibitory constituents from Buddleja crispa

Ahmad, Ijaz,Malik, Abdul,Afza, Nighat,Anis, Itrat,Fatima, Itrat,Nawaz, Sarfraz Ahmad,Tareen, Rasool Bukhsh,Iqbal Choudhary

, p. 341 - 346 (2005)

Steroidal galactoside 1 and aryl esters 2 and 3 have been isolated from Buddleja crispa, along with ginipin 4, gardiol 5, 1-heptacosanol 6, and methyl benzoate 7, isolated for the first time from this species. The structures of all of the compounds were determined by spectroscopic techniques and chemical studies. The steroidal galactoside 1 is an inhibitor of lipoxygenase. Compounds 1-3 displayed inhibitory activity against butyrylcholinesterse, while compounds 2 and 3 further showed inhibition against acetylcholinesterase.

Harris et al.

, p. C27 (1974)

In-Situ generation of surface-active HCo(CO)y like intermediate from gold supported on ion-promoted Co3O4 for induced hydroformylation-hydrogenation of alkenes to alcohols

Akinnawo, Christianah A.,Meijboom, Reinout,Mogudi, Batsile M.,Oseghale, Charles O.

, (2020)

In this study, a greener and stable surface-active cobalt-carbonyl like specie [HCo(CO)y] was generated via H2 and CO spillover by gold on ion-promoted cobalt oxide. The supports and catalysts syntheses were based on inverse micelle and deposition-precipitation methods, respectively. The temperature-programmed reduction was used for optimization to obtain the best supports. The catalysts with activity (Co3O4 3O4 3O4 and Au loadings 10 percent 3O4 catalyst more active than the others and displayed excellent alcohol chemoselectivity with varying regioselectivity under milder reaction conditions. The reaction was assumed to take place via the formation of [HCo(CO)y] specie, as the active catalytic site of the catalyst. The enhanced catalytic performance was also ascribed to the low-temperature reducibility and surface basicity of the nanomaterials. The stability of the catalyst was evaluated by recycling, with its mesostructure retained after four cycles.

Lithium Triethylborohydride-promoted Hydroboration of Alkenes with Dialkoxyboranes

Arase, Akira,Nunokawa, Yutaka,Masuda, Yuzuru,Hoshi, Masayuki

, p. 51 - 52 (1992)

In the presence of a catalytic ammount of lithium triethylborohydride (LiBEt3H) the hydroboration of alkenes with dialkoxyboranes is promoted markedly to provide the hydroboration products almost quantitatively under mild reaction conditions.

Hydroboration. 54. New General Synthesis of Alkyldihaloboranes via Hydroboration of Alkenes with Dihaloborane-Dimethyl Sulfide Complexes. Unusual Trends in the Reactivities and Directive Effects

Brown, Herbert C.,Ravindran, N.,Kulkarni, Surendra U.

, p. 384 - 389 (1980)

The reactions of alkenes with the dimethyl sulfide complexes of the dihaloboranes (HBX2*SMe2; X = Cl, Br, I) have been studied in detail.Dichloroborane-dimethyl sulfide (HBCl2*SMe2) hydroborates representative olefins relatively slowly and requires the presence of a strong Lewis acid, such as boron trichloride, to complete the hydroboration reaction rapidly.Unexpectedly, dibromoborane-dimethyl sulfide (HBBr2*SMe2) and diiodoborane-dimethyl sulfide (HBI2*SMe2) react readily with olefins, even in the absence of such Lewis acids.This is contrary to the trend expected on the basis of the strenghts of these methyl sulfide adducts and a hydroboration mechanism involving a prior dissociation of the addition compound.The hydroboration of olefins with these reagents, followed by distillation under reduced pressure, affords alkyldihaloborane-dimethyl sulfide complexes in good yields.These are readily converted by hydrolysis into the boronic acids or by methanolysis to the corresponding esters.Oxidation with alkaline hydrogen peroxide utilizing sufficient sodium hydroxide to neutralize the hydrogen halide readily provides the corresponding alcohols.HBBr2*SMe2 and HBI2*SMe2 exhibit an unusual directive effect in the hydroboration of trisubstituted olefins, giving unexpected enhanced amounts of the Markovnikov (tertiary) derivatives.

Alkene-pinacolborane hydroborations catalyzed by lanthanum tris[bis(trimethylsilyl)amide]

Horino, Yoshikazu,Livinghouse, Tom,Stan, Magdalena

, p. 2639 - 2641 (2004)

Tris[bis(trimethylsilyl)amide] has been shown to be an effective catalyst for the hydroboration of representative alkenes and styrenes by pinacolborane.

-

Bigley,Payling

, p. 3974 (1965)

-

Upgrading ethanol to 1-butanol with a homogeneous air-stable ruthenium catalyst

Tseng, Kuei-Nin T.,Lin, Steve,Kampf, Jeff W.,Szymczak, Nathaniel K.

, p. 2901 - 2904 (2016)

An amide-derived N,N,N-Ru(ii) complex catalyzes the conversion of EtOH to 1-BuOH with high activity. Conversion to alcohol upgraded products exceeds 250 turnovers per hour (>50% conversion) with 0.1 mol% catalyst loading. In addition to high activity for ethanol upgrading, catalytic reactions can be set up under ambient conditions with no loss in activity.

-

Cottle,Hollyday

, p. 510,513,514 (1947)

-

The key role of the latent N-H group in Milstein's catalyst for ester hydrogenation

Chianese, Anthony R.,He, Tianyi,Jarczyk, Cole E.,Keith, Jason M.,Kelly, Sophie. E.,Kim, Thao,Pham, John,Reynolds, Eamon F.

, p. 8477 - 8492 (2021)

We previously demonstrated that Milstein's seminal diethylamino-substituted PNN-pincer-ruthenium catalyst for ester hydrogenation is activated by dehydroalkylation of the pincer ligand, releasing ethane and eventually forming an NHEt-substituted derivative that we proposed is the active catalyst. In this paper, we present a computational and experimental mechanistic study supporting this hypothesis. Our DFT analysis shows that the minimum-energy pathways for hydrogen activation, ester hydrogenolysis, and aldehyde hydrogenation rely on the key involvement of the nascent N-H group. We have isolated and crystallographically characterized two catalytic intermediates, a ruthenium dihydride and a ruthenium hydridoalkoxide, the latter of which is the catalyst resting state. A detailed kinetic study shows that catalytic ester hydrogenation is first-order in ruthenium and hydrogen, shows saturation behavior in ester, and is inhibited by the product alcohol. A global fit of the kinetic data to a simplified model incorporating the hydridoalkoxide and dihydride intermediates and three kinetically relevant transition states showed excellent agreement with the results from DFT.

HYDROMAGNESATION OF UNSATURATED COMPOUNDS USING DIETHYLAMINOMAGNESIUM HYDRIDE, CATALYZED BY TRANSITION METAL COMPLEXES

Vostrikova, O. S.,Sultanov, R. M.,Dzhemilev, U. M.

, p. 1724 - 1726 (1983)

-

Chemoselective hydrogenolysis of tetrahydrofurfuryl alcohol to 1,5-pentanediol

Koso, Shuichi,Furikado, Ippei,Shimao, Akira,Miyazawa, Tomohisa,Kunimori, Kimio,Tomishige, Keiichi

, p. 2035 - 2037 (2009)

Direct conversion of tetrahydrofurfuryl alcohol, which is one of the biomass-derived chemicals, to 1,5-pentanediol was realized by chemoselective hydrogenolysis catalyzed by Rh/SiO2 modified with ReOx species, and this reaction route gave higher yield than the conventional multi-step method.

N-methylpyrrolidine-zinc borohydride: As a new stable and efficient reducing agent in organic synthesis

Tajbakhsh,Lakouraj,Mohanazadeh,Ahmadi-Nejhad

, p. 229 - 236 (2003)

N-Methylpyrrolidine-zinc borohydride is readily prepared and used for reduction of a variety of organic compounds such as aldehydes, ketones, acid chlorides, and esters. Reactions are performed in THF at room temperature or under reflux condition and the yields are good to excellent. Complete regio-selectivity are observed in reduction of α,β-unsaturated carbonyl compounds.

Selective hydrogenation of 3-Hexyn-1-ol with Pd nanoparticles synthesized via microemulsions

Montsch, Thomas,Heuchel, Moritz,Traa, Yvonne,Klemm, Elias,Stubenrauch, Cosima

, p. 19 - 28 (2017)

In the study at hand we present a design strategy for novel catalysts which can be used for the selective hydrogenation of alkynes to alkenes. The design of the novel catalysts is based on two main ideas, namely (1) the synthesis of Pd nanoparticles via microemulsions and (2) the use of highly-ordered mesoporous silica with a 3-D pore network (FDU-12) serving as support. The nanoparticles are deposited on FDU-12 in two different ways. Firstly, we simply impregnated the support with a dispersion of the nanoparticles. The resulting catalyst was not selective at all; on the contrary, it fully hydrogenated our model alkyne, namely 3-hexyn-1-ol. Secondly, we synthesized the FDU-12 in the presence of the nanoparticles (in-situ synthesis). In this case, we obtained one catalyst which performed as well as the Lindlar catalyst although the metal content was slightly lower and our catalyst contained no Pb. Another catalyst of the same series, prepared in the presence of another stabilizer, performed as well as the NanoSelect catalyst but at a 7 times higher metal content. For the sake of comparison we also impregnated FDU-12 via classical incipient wetness impregnation and again obtained a completely nonselective catalyst. Our results demonstrate that the in-situ synthesis has great potential as regards the development of novel catalysts.

Hach

, p. 340 (1974)

Hydrogenation of adipic acid to 1,6-hexanediol by supported bimetallic Ir-Re catalyst

Li, Xiaoyue,Liang, Changhai,Luo, Jingjie

, (2020)

A series of supported Ir-Re catalysts have been synthesized and used for the hydrogenation of adipic acid to 1,6-hexanediol. The influences of supporting materials and the Ir/Re atomic ratio on the catalytic performances have been studied. Results suggested that Ir-Re supported on carbon materials and alumina had appropriate acid sites and better activity for the hydrogenation of adipic acid. Compared to the monometallic catalysts, synergistic interaction was generated and electrons were delivered from Ir to Re. The uniform distribution of metal particles in the Ir-Re catalysts and the well restrained H2-spillover effect facilitated the transformation of adipic acid and the selective production of 1,6-hexanediol. The selectivity of 1,6-hexanediol was 59% with complete conversion of adipic acid at 180 °C in 10 MPa H2 after reaction for 16 h. After four times of reaction, the selectivity of 1,6-hexanediol only decreased about 4%.

Regiodivergent Reductive Opening of Epoxides by Catalytic Hydrogenation Promoted by a (Cyclopentadienone)iron Complex

De Vries, Johannes G.,Gandini, Tommaso,Gennari, Cesare,Jiao, Haijun,Pignataro, Luca,Stadler, Bernhard M.,Tadiello, Laura,Tin, Sergey

, p. 235 - 246 (2022/01/03)

The reductive opening of epoxides represents an attractive method for the synthesis of alcohols, but its potential application is limited by the use of stoichiometric amounts of metal hydride reducing agents (e.g., LiAlH4). For this reason, the corresponding homogeneous catalytic version with H2 is receiving increasing attention. However, investigation of this alternative has just begun, and several issues are still present, such as the use of noble metals/expensive ligands, high catalytic loading, and poor regioselectivity. Herein, we describe the use of a cheap and easy-To-handle (cyclopentadienone)iron complex (1a), previously developed by some of us, as a precatalyst for the reductive opening of epoxides with H2. While aryl epoxides smoothly reacted to afford linear alcohols, aliphatic epoxides turned out to be particularly challenging, requiring the presence of a Lewis acid cocatalyst. Remarkably, we found that it is possible to steer the regioselectivity with a careful choice of Lewis acid. A series of deuterium labeling and computational studies were run to investigate the reaction mechanism, which seems to involve more than a single pathway.

One-Pot Bioelectrocatalytic Conversion of Chemically Inert Hydrocarbons to Imines

Chen, Hui,Tang, Tianhua,Malapit, Christian A.,Lee, Yoo Seok,Prater, Matthew B.,Weliwatte, N. Samali,Minteer, Shelley D.

supporting information, p. 4047 - 4056 (2022/02/10)

Petroleum hydrocarbons are our major energy source and an important feedstock for the chemical industry. With the exception of combustion, the deep conversion of chemically inert hydrocarbons to more valuable chemicals is of considerable interest. However, two challenges hinder this conversion. One is the regioselective activation of inert carbon-hydrogen (C-H) bonds. The other is designing a pathway to realize this complicated conversion. In response to the two challenges, a multistep bioelectrocatalytic system was developed to realize the one-pot deep conversion from heptane to N-heptylhepan-1-imine under mild conditions. First, in this enzymatic cascade, a bioelectrocatalytic C-H bond oxyfunctionalization step based on alkane hydroxylase (alkB) was applied to regioselectively convert heptane to 1-heptanol. By integrating subsequent alcohol oxidation and bioelectrocatalytic reductive amination steps based on an engineered choline oxidase (AcCO6) and a reductive aminase (NfRedAm), the generated 1-heptanol was successfully converted to N-heptylhepan-1-imine. The electrochemical architecture provided sufficient electrons to drive the bioelectrocatalytic C-H bond oxyfunctionalization and reductive amination steps with neutral red (NR) as electron mediator. The highest concentration of N-heptylhepan-1-imine achieved was 0.67 mM with a Faradaic efficiency of 45% for C-H bond oxyfunctionalization and 70% for reductive amination. Hexane, octane, and ethylbenzene were also successfully converted to the corresponding imines. Via regioselective C-H bond oxyfunctionalization, intermediate oxidation, and reductive amination, the bioelectrocatalytic hydrocarbon deep conversion system successfully realized the challenging conversion from inert hydrocarbons to imines that would have been impossible by using organic synthesis methods and provided a new methodology for the comprehensive conversion and utilization of inert hydrocarbons.

Chromium-Catalyzed Production of Diols From Olefins

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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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