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111-87-5 Usage

Safety Profile

Poison by intravenous route.Moderately toxic by ingestion. Mutation data reported. Askin irritant. Combustible liquid when exposed to heat orflame; can react with oxidizing materials. To fight fire, usewater foam, fog, alcohol foam, dry chemical, CO2

Check Digit Verification of cas no

The CAS Registry Mumber 111-87-5 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, 8 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 111-87:
(5*1)+(4*1)+(3*1)+(2*8)+(1*7)=35
35 % 10 = 5
So 111-87-5 is a valid CAS Registry Number.
InChI:InChI=1/C8H18O/c1-2-3-4-5-6-7-8-9/h9H,2-8H2,1H3

111-87-5 Well-known Company Product Price

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  • (Code)Product description
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  • Detail
  • Alfa Aesar

  • (A15977)  1-Octanol, 99%   

  • 111-87-5

  • 500ml

  • 261.0CNY

  • Detail
  • Alfa Aesar

  • (A15977)  1-Octanol, 99%   

  • 111-87-5

  • 2500ml

  • 860.0CNY

  • Detail
  • Alfa Aesar

  • (A15977)  1-Octanol, 99%   

  • 111-87-5

  • 10000ml

  • 1870.0CNY

  • Detail
  • Sigma-Aldrich

  • (297887)  1-Octanol  anhydrous, ≥99%

  • 111-87-5

  • 297887-100ML

  • 764.01CNY

  • Detail
  • Sigma-Aldrich

  • (297887)  1-Octanol  anhydrous, ≥99%

  • 111-87-5

  • 297887-1L

  • 1,377.09CNY

  • Detail
  • Sigma-Aldrich

  • (360562)  1-Octanol  ACS spectrophotometric grade, ≥99%

  • 111-87-5

  • 360562-1L

  • 1,407.51CNY

  • Detail
  • Vetec

  • (V900239)  1-Octanol  Vetec reagent grade, 98%

  • 111-87-5

  • V900239-500ML

  • 86.58CNY

  • Detail
  • Sigma-Aldrich

  • (472328)  1-Octanol  ACS reagent, ≥99%

  • 111-87-5

  • 472328-100ML

  • 527.67CNY

  • Detail
  • Sigma-Aldrich

  • (472328)  1-Octanol  ACS reagent, ≥99%

  • 111-87-5

  • 472328-1L

  • 1,107.99CNY

  • Detail
  • Sigma-Aldrich

  • (472328)  1-Octanol  ACS reagent, ≥99%

  • 111-87-5

  • 472328-2.5L

  • 1,873.17CNY

  • Detail
  • Sigma-Aldrich

  • (472328)  1-Octanol  ACS reagent, ≥99%

  • 111-87-5

  • 472328-4L

  • 2,579.85CNY

  • Detail
  • Sigma-Aldrich

  • (112615)  1-Octanol  ReagentPlus®, 99%

  • 111-87-5

  • 112615-2.5L

  • 1,003.86CNY

  • Detail

111-87-5SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name octan-1-ol

1.2 Other means of identification

Product number -
Other names Alfol 8

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Fragrances
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:111-87-5 SDS

111-87-5Synthetic route

N-Methylformamide
123-39-7

N-Methylformamide

A

octanol
111-87-5

octanol

B

di-n-octyl ether
629-82-3

di-n-octyl ether

C

octyl formate
112-32-3

octyl formate

D

N-methylmethanimidamide hydroiodide

N-methylmethanimidamide hydroiodide

Conditions
ConditionsYield
With 1-Iodooctane at 146℃;A n/a
B n/a
C n/a
D 100%
N-Methylformamide
123-39-7

N-Methylformamide

A

octanol
111-87-5

octanol

B

di-n-octyl ether
629-82-3

di-n-octyl ether

C

octyl formate
112-32-3

octyl formate

D

N-methylmethanimidamide hydrobromide

N-methylmethanimidamide hydrobromide

Conditions
ConditionsYield
With 1-bromo-octane at 146℃;A n/a
B n/a
C n/a
D 100%
2-(octyloxy)-tetrahydrofuran
52767-49-4

2-(octyloxy)-tetrahydrofuran

octanol
111-87-5

octanol

Conditions
ConditionsYield
With toluene-4-sulfonic acid In ethanol for 1h; Ambient temperature;100%
oct-1-ene
111-66-0

oct-1-ene

thexylchloroborane * dimethylsulfide
75067-06-0

thexylchloroborane * dimethylsulfide

A

octanol
111-87-5

octanol

B

rac-octan-2-ol
4128-31-8

rac-octan-2-ol

C

2,3-dimethylbutan-2-ol
594-60-5

2,3-dimethylbutan-2-ol

Conditions
ConditionsYield
With methanol; dihydrogen peroxide Product distribution; different solvents; other olefins;A 99.2%
B 0.8%
C 100%
trimethyl(oct-1-yloxy)silane
14246-16-3

trimethyl(oct-1-yloxy)silane

octanol
111-87-5

octanol

Conditions
ConditionsYield
With dinitrogen tetraoxide In dichloromethane at -10℃; deprotection;100%
With water; 1,1,1,3,3,3-hexamethyl-disilazane In dichloromethane at 20℃; for 0.483333h;100%
With polymer-supported ammonium fluoride: D296 In methanol at 20℃; for 2h;98%
Octanal
124-13-0

Octanal

octanol
111-87-5

octanol

Conditions
ConditionsYield
With hydrogen; Et4N In 1,2-dimethoxyethane at 100℃; under 38000 Torr; for 13h;100%
With zirconium(IV) tetraisopropoxide 2-propanol; 4 Angstroem MS; 1,1'-bi-2-naphthol In isopropyl alcohol; toluene at 20℃; for 18h;100%
With zirconium(IV) tetraisopropoxide 2-propanol; 1,1'-bi-2-naphthol In toluene at 20℃; for 1h;100%
1-Chloroethyl n-Octyl Crbonate
99478-15-6

1-Chloroethyl n-Octyl Crbonate

ammonium thiocyanate

ammonium thiocyanate

A

octanol
111-87-5

octanol

B

n-octyl 1-thiocyanoethylcarbonate
109548-51-8

n-octyl 1-thiocyanoethylcarbonate

Conditions
ConditionsYield
In methanol for 27h; Ambient temperature;A 22%
B 100%
2-methyl-4-(octyloxy)but-2-ene
253588-34-0

2-methyl-4-(octyloxy)but-2-ene

octanol
111-87-5

octanol

Conditions
ConditionsYield
With titanium tetrachloride; tetra-(n-butyl)ammonium iodide In dichloromethane at 0℃; for 2h; deprenylation;100%
With 1.3-propanedithiol; cerium(III) chloride; sodium iodide In nitromethane for 10h; Heating;17%
tert-Butyl-octyloxy-diphenyl-silane

tert-Butyl-octyloxy-diphenyl-silane

octanol
111-87-5

octanol

Conditions
ConditionsYield
With water at 100℃; for 24h; Kinetics; Reagent/catalyst; Inert atmosphere;100%
With acetyl chloride In methanol at 20℃; for 2h;97%
With zinc trifluoromethanesulfonate In methanol at 0 - 20℃; for 2h; chemoselective reaction;88%
tert-butyl octyl ether
51323-70-7

tert-butyl octyl ether

octanol
111-87-5

octanol

Conditions
ConditionsYield
With sodium iodide; cerium(III) chloride In acetonitrile at 70℃; for 3.5h; Kinetics; Further Variations:; Temperatures; effect of water;100%
With cerium(III) chloride; sodium iodide In acetonitrile at 70℃; for 8h;94%
With magnesium(II) perchlorate In dichloromethane at 40℃; for 5h;
With erbium(III) triflate In methanol at 100℃; for 0.75h; Microwave irradiation;
2-octyloxy-tetrahydro-pyran
70690-19-6

2-octyloxy-tetrahydro-pyran

octanol
111-87-5

octanol

Conditions
ConditionsYield
With methanol; zirconium(IV) chloride at 20℃; for 4h;99%
silica-supported prop-1-ylsulfonic acid In methanol99.7%
With methanol at 20℃; for 0.5h;99%
Octanoic acid
124-07-2

Octanoic acid

octanol
111-87-5

octanol

Conditions
ConditionsYield
With samarium diiodide; heptanal; samarium(III) trifluoromethanesulfonate In tetrahydrofuran; methanol; potassium hydroxide at 20℃; for 0.075h; Reduction;99%
With 1,1,3,3-Tetramethyldisiloxane; copper(II) bis(trifluoromethanesulfonate) In toluene at 80℃; for 16h; sealed tube;91%
With hydrogen In neat (no solvent) at 180℃; under 37503.8 Torr; for 12h;91%
methyl octanate
111-11-5

methyl octanate

octanol
111-87-5

octanol

Conditions
ConditionsYield
With C32H36ClNO2P2Ru; potassium tert-butylate; hydrogen In neat (no solvent) at 120℃; under 38002.6 Torr; for 20h; Autoclave; Green chemistry;99%
With [RuCl2((E)-N-(2-(diphenylphosphino)benzyl)-1-(6-((diphenylphosphino)methyl)pyridin-2-yl)methanimine)]; hydrogen; sodium ethanolate at 80℃; under 37503.8 Torr; for 12h; Autoclave;99%
With lithium borohydride In tetrahydrofuran at 65℃; for 2h;98%
octyl tetrahydrofuran-2-carboxylate

octyl tetrahydrofuran-2-carboxylate

octanol
111-87-5

octanol

Conditions
ConditionsYield
With ytterbium(III) triflate In methanol for 4h; Ambient temperature;99%
1-methoxy-4-octyloxymethyl benzene
54384-75-7

1-methoxy-4-octyloxymethyl benzene

octanol
111-87-5

octanol

Conditions
ConditionsYield
With silver hexafluoroantimonate; 1,2,3-trimethoxybenzene In dichloromethane at 40℃; for 7h;99%
With 4,4'-bipyridine; (phthalocyaninato)iron(II); oxygen; 2,3-dicyano-5,6-dichloro-p-benzoquinone In toluene at 80℃; under 3000.3 Torr; for 14h; Autoclave;90%
Stage #1: 1-methoxy-4-octyloxymethyl benzene With sodium hydrogencarbonate; bis-[(trifluoroacetoxy)iodo]benzene; meso-2,5-bis(methoxycarbonyl)-2,5-dimethylpyrrolidine-1-oxyl In dichloromethane at 20℃; for 2h;
Stage #2: With water In dichloromethane chemoselective reaction;
90%
Conditions
ConditionsYield
With acetylacetonatodicarbonylrhodium(l); trifluorormethanesulfonic acid; carbon monoxide; N-(5-diphenylphosphanylpyrrole-2-carbonyl)guanidine; hydrogen In dichloromethane at 40℃; under 15001.5 Torr; for 7h; Autoclave; chemoselective reaction;99%
oct-1-ene
111-66-0

oct-1-ene

A

octanol
111-87-5

octanol

B

rac-octan-2-ol
4128-31-8

rac-octan-2-ol

Conditions
ConditionsYield
With oxonium; oxygen; diisobutyl(2,6-di-tert-butyl-4- methylphenoxy)aluminum Product distribution; regioselectivity of hydroalumination;A 98%
B n/a
Stage #1: oct-1-ene With 1-bromo-butane; sodium tetrahydroborate; Aliquat 336 at 20℃; for 16h; Addition; Hydroboration;
Stage #2: With sodium hydroxide; dihydrogen peroxide at 40℃; for 1h; Oxidation;
A 88%
B 6%
With sodium tetrahydroborate; oxygen; (2,3,7,8,12,13,17,18-octaethylporphyrinato)rhodium(III) chloride In tetrahydrofuran Ambient temperature; 48-130 h; Yield given;
tert-Butyl-dimethyl-octyloxy-silane
92976-53-9

tert-Butyl-dimethyl-octyloxy-silane

octanol
111-87-5

octanol

Conditions
ConditionsYield
With acetyl chloride In methanol at 0 - 5℃; for 0.0833333h;98%
With maleic acid In water; acetonitrile at 20℃; for 2h;98%
With potassium hydrogensulfate In methanol at 20℃; for 1.5h;96%
methoxymethyl octyl ether
88738-43-6

methoxymethyl octyl ether

octanol
111-87-5

octanol

Conditions
ConditionsYield
With pyridinium p-toluenesulfonate In butanone for 7.25h; Heating;97%
phosphotungstic acid In ethanol for 3.5h; Heating;92%
With 1-methylimidazole hydrogen sulfate at 120℃; for 0.0333333h; Microwave irradiation; chemoselective reaction;91%
With bismuth(III) chloride; water In acetonitrile at 50℃; for 8h;84%
(2-Methoxyethoxy)methyl octyl ether
88738-42-5

(2-Methoxyethoxy)methyl octyl ether

octanol
111-87-5

octanol

Conditions
ConditionsYield
With pyridinium p-toluenesulfonate In butanone for 8.5h; Heating;97%
S-sec-butyl caprylthioate
89363-63-3

S-sec-butyl caprylthioate

octanol
111-87-5

octanol

Conditions
ConditionsYield
With Li(1+)*C12H28AlO3(1-) In tetrahydrofuran; hexane for 0.5h; Ambient temperature;97%
octanoic acid ethyl ester
106-32-1

octanoic acid ethyl ester

octanol
111-87-5

octanol

Conditions
ConditionsYield
With C30H34Cl2N2P2Ru; potassium methanolate; hydrogen In tetrahydrofuran at 100℃; under 38002.6 - 76005.1 Torr; for 15h; Reagent/catalyst; Temperature; Pressure; Glovebox; Autoclave;96%
Stage #1: octanoic acid ethyl ester With C33H58FeN3PSi2; phenylsilane In toluene at 20℃; for 4h; Inert atmosphere; Glovebox; Green chemistry;
Stage #2: With sodium hydroxide In toluene for 1h; Green chemistry;
80%
With methanol; sodium tetrahydroborate; sodium ethanolate at 40℃;80%
octylmagnesium bromide
17049-49-9

octylmagnesium bromide

octanol
111-87-5

octanol

Conditions
ConditionsYield
With titanium(IV) isopropylate; tert.-butylhydroperoxide In diethyl ether at -78℃; for 12h;96%
With 2-t-butylperoxy-1,3,2-dioxaborolane In tetrahydrofuran 1.) overnight, 2.) reflux, 3 h;80%
With diethyl ether; oxygen at 0℃;
n-octyl acetate
112-14-1

n-octyl acetate

octanol
111-87-5

octanol

Conditions
ConditionsYield
With ethanol at 90℃; under 10343.2 Torr; for 16h; Catalytic behavior; Reagent/catalyst; Inert atmosphere;96%
With ytterbium(III) triflate In methanol for 30h; Ambient temperature;80%
With [t-Bu2SnOH(Cl)]2 In methanol at 30℃; for 6h; Deacetylation;93 % Chromat.
n-butyllithium
109-72-8, 29786-93-4

n-butyllithium

(2R,3S)-linaloal oxide silyl ether

(2R,3S)-linaloal oxide silyl ether

A

octanol
111-87-5

octanol

B

(6R,7S)-7,11-Dimethyl-7-(methyl-diphenyl-silanyloxy)-dodec-10-en-6-ol

(6R,7S)-7,11-Dimethyl-7-(methyl-diphenyl-silanyloxy)-dodec-10-en-6-ol

Conditions
ConditionsYield
With boron trifluoride diethyl etherate In tetrahydrofuran; hexane at -78℃; for 0.05h;A n/a
B 95%
1-Iodooctane
629-27-6

1-Iodooctane

octanol
111-87-5

octanol

Conditions
ConditionsYield
With Amberlyst A 26; carbonate form In benzene for 4h; Heating;95%
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 20℃; for 0.0166667h;95%
In N,N,N,N,N,N-hexamethylphosphoric triamide; water at 100℃; for 2.5h;92%
With N,N,N,N,N,N-hexamethylphosphoric triamide; air; zinc In tetrahydrofuran65 % Spectr.
allyl octyl ether
3295-97-4

allyl octyl ether

octanol
111-87-5

octanol

Conditions
ConditionsYield
With chloro-trimethyl-silane; sodium iodide In acetonitrile for 0.05h;95%
With ethylmagnesium chloride; iron(II) chloride In tetrahydrofuran; m-xylene at 20℃; for 1h;79%
With boron trifluoride diethyl etherate; tetra-(n-butyl)ammonium iodide In chloroform at 65℃; for 5h;75%
With 1.3-propanedithiol; cerium(III) chloride; sodium iodide In nitromethane for 30h; Heating;83 % Chromat.
With samarium diiodide; water; isopropylamine In tetrahydrofuran at 20℃; for 0.05h;
1-bromo-octane
111-83-1

1-bromo-octane

octanol
111-87-5

octanol

Conditions
ConditionsYield
With potassium hydroxide; tetrafluoroboric acid; sodium hydrogencarbonate; mercury(II) oxide In 1,4-dioxane 1.) room temp., 3 h;95%
In N,N,N,N,N,N-hexamethylphosphoric triamide; water at 100℃; for 5.5h;92%
With Amberlyst A 26; carbonate form In benzene for 4h; Heating;90%
octyl formate
112-32-3

octyl formate

octanol
111-87-5

octanol

Conditions
ConditionsYield
Stage #1: octyl formate With phenylsilane; C74H74Mn2N6P4 at 25℃; for 0.5h; Glovebox; Inert atmosphere;
Stage #2: With sodium hydroxide In water at 25℃; for 2h; Glovebox; Inert atmosphere;
95%
With sodium hydroxide Ambient temperature; Yield given;
n-octanoic acid chloride
111-64-8

n-octanoic acid chloride

octanol
111-87-5

octanol

Conditions
ConditionsYield
With sodium tetrahydroborate; titanium tetrachloride In 1,2-dimethoxyethane for 14h; Ambient temperature;95%
With diisopropoxytitanium(III) tetrahydroborate In dichloromethane at -20℃; for 0.133333h;86%
Multi-step reaction with 2 steps
1: LiAlH(i-Bu)2(n-Bu) / 0.5 h / 78 °C
2: 1.)LiAlH(i-Bu)2(n-Bu) 2.) NaBH4 / 1.) 1h, -78 deg C 2.) 1h, r.t., EtOH
View Scheme
Multi-step reaction with 2 steps
1: LiAlH(i-Bu)2(n-Bu) / 0.5 h / 78 °C
2: LiAlH(i-Bu)2(n-Bu) / tetrahydrofuran; hexane / 6 h / -78 °C / reduction of other carbonyl compounds
View Scheme
triethylsilane
617-86-7

triethylsilane

octanol
111-87-5

octanol

1-octyl triethylsilyl ether
17957-36-7

1-octyl triethylsilyl ether

Conditions
ConditionsYield
cationic dirhodium(II) complex at 50℃; for 24h;100%
With Rh/AlO(OH) In toluene at 25℃; for 24h; Inert atmosphere;90%
dirhodium(II) tetrakis(perfluorobutyrate) In dichloromethane for 3h; Product distribution; Ambient temperature; var. alcohols; rel. reactivities for triethylsilane alcoholysis; var. catalysts;86%
octanol
111-87-5

octanol

1-Chlorooctane
111-85-3

1-Chlorooctane

Conditions
ConditionsYield
With diphenylselenium dichloride; triphenylphosphine In benzene for 0.333333h; Product distribution; other reagent, solvent;100%
With Me2SeCl2; triphenylphosphine In chloroform for 0.333333h;100%
With thionyl chloride; Triphenylphosphine oxide In neat (no solvent) at 100℃; for 5h; Mechanism; Reagent/catalyst;100%
octanol
111-87-5

octanol

octyl nitrate
629-39-0

octyl nitrate

Conditions
ConditionsYield
With nitric acid for 12h; Ambient temperature;100%
With nitric acid for 12h; Ambient temperature;100%
With nitric acid; urea; europium(III) trifluoromethanesulfonate In cyclohexane at 95℃; for 12h; Schlenk technique;96%
octanol
111-87-5

octanol

Octanoic acid
124-07-2

Octanoic acid

Conditions
ConditionsYield
With nitric acid for 0.333333h; Ambient temperature; sonication;100%
With nitric acid for 0.333333h; Ambient temperature; sonication;100%
With ruthenium trichloride; iodobenzene; potassium peroxomonosulfate In water; acetonitrile at 20℃; for 16h;100%
octanol
111-87-5

octanol

octyl octylate
2306-88-9

octyl octylate

Conditions
ConditionsYield
With carbonylhydrido[6-(di-tert-butylphosphinomethylene)-2-(N,N-diethylaminomethyl)-1,6-dihydropyridine]ruthenium(II); N-(4-chlorophenyl)formamide In 1,3,5-trimethyl-benzene at 125℃; for 48h; Reagent/catalyst;100%
With sodium bromate; hydrogen bromide In tetrachloromethane at 35 - 37℃; for 2h;99%
With disodium hydrogenphosphate; benzyltrimethylammonium tribromide In tetrachloromethane; water at 60℃; for 8.5h;99%
octanol
111-87-5

octanol

acetic anhydride
108-24-7

acetic anhydride

n-octyl acetate
112-14-1

n-octyl acetate

Conditions
ConditionsYield
With magnesium(II) perchlorate at 20℃; for 0.0166667h;100%
With cyclopenta-1,3-diene; dimethyl cis-but-2-ene-1,4-dioate; scandium tris(trifluoromethanesulfonate) In dichloromethane at 0℃; for 12h;100%
With erbium(III) chloride at 50℃; for 1h;100%
octanol
111-87-5

octanol

methanesulfonyl chloride
124-63-0

methanesulfonyl chloride

n-octyl methanesulfonate
16156-52-8

n-octyl methanesulfonate

Conditions
ConditionsYield
Stage #1: octanol With triethylamine In dichloromethane at 25℃;
Stage #2: methanesulfonyl chloride In dichloromethane at 0 - 20℃;
100%
With triethylamine In dichloromethane at -15℃; for 1h; Green chemistry;100%
With zinc oxide-nanoparticle at 50℃; for 4h; Neat (no solvent); chemoselective reaction;93%
octanol
111-87-5

octanol

1,1,1,3,3,3-hexamethyl-disilazane
999-97-3

1,1,1,3,3,3-hexamethyl-disilazane

trimethyl(oct-1-yloxy)silane
14246-16-3

trimethyl(oct-1-yloxy)silane

Conditions
ConditionsYield
With asymmetric salen type di-Schiff base-based zinc complex supported on Fe3O4 nanoparticles at 20℃; for 0.383333h;100%
With ammonium thiocyanate In dichloromethane at 0℃; for 0.166667h;99%
phosphotungstic acid at 55 - 60℃; for 0.116667h;96%
octanol
111-87-5

octanol

benzoic acid
65-85-0

benzoic acid

n-octyl benzoate
94-50-8

n-octyl benzoate

Conditions
ConditionsYield
With bis(5-norbornenyl-2-methyl) azodicarboxylate; polystyrene-supported PPh3 In tetrahydrofuran Esterification; Mitsunobu reaction;100%
With toluene-4-sulfonic acid for 0.05h; Irradiation;97%
With 1-(tert-butyl)-2-(chlorobenzyl) azodicarboxylate; triphenylphosphine In dichloromethane at 0 - 20℃; for 4h; Reagent/catalyst; Mitsunobu Displacement;97.9%
octanol
111-87-5

octanol

trifluoroacetic anhydride
407-25-0

trifluoroacetic anhydride

n-octyl trifluoroacetate
2561-21-9

n-octyl trifluoroacetate

Conditions
ConditionsYield
erbium(III) triflate In acetonitrile at 20℃; for 2.5h;100%
With erbium(III) chloride for 1.5h; Heating;99%
With triethylamine In benzene at 25 - 30℃; for 1h;
carbon disulfide
75-15-0

carbon disulfide

octanol
111-87-5

octanol

methyl iodide
74-88-4

methyl iodide

O-octyl-S-methyl dithiocarbonate
35812-29-4

O-octyl-S-methyl dithiocarbonate

Conditions
ConditionsYield
Stage #1: carbon disulfide; octanol With 1H-imidazole; sodium hydride In tetrahydrofuran at 20℃; for 0.5h; Addition;
Stage #2: methyl iodide In tetrahydrofuran at 20℃; for 0.5h; Methylation; Further stages.;
100%
With sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate In water for 1.5h; Ambient temperature;95%
Stage #1: carbon disulfide; octanol In dimethyl sulfoxide at 20℃; for 0.333333h;
Stage #2: With N-benzyl-trimethylammonium hydroxide In dimethyl sulfoxide at 20℃; for 1h;
Stage #3: methyl iodide In dimethyl sulfoxide at 20℃; for 2h;
93%
octanol
111-87-5

octanol

phenylglyoxal hydrate
1074-12-0

phenylglyoxal hydrate

2,2-bis(octyloxy)-1-phenylethan-1-one
161065-36-7

2,2-bis(octyloxy)-1-phenylethan-1-one

Conditions
ConditionsYield
With pyridinium p-toluenesulfonate In toluene for 2h; Heating;100%
In toluene for 2h; Heating / reflux;100%
With sulfuric acid In benzene Heating;87%
octanol
111-87-5

octanol

acetic acid
64-19-7

acetic acid

n-octyl acetate
112-14-1

n-octyl acetate

Conditions
ConditionsYield
With Keggin-type 12-tungstophosphoric acid supported on MCM-41 at 80℃; for 1h;100%
LaY zeolite at 116℃; for 6h; Acetylation;98%
With bismuth(lll) trifluoromethanesulfonate at 20℃; for 0.5h;98%
phthalimide
136918-14-4

phthalimide

octanol
111-87-5

octanol

N-octylphthalimide
59333-62-9

N-octylphthalimide

Conditions
ConditionsYield
With bis(5-norbornenyl-2-methyl) azodicarboxylate; polystyrene-supported PPh3 In tetrahydrofuran Substitution; Mitsunobu reaction;100%
With 1-(tert-butyl)-2-(chlorobenzyl) azodicarboxylate; triphenylphosphine In dichloromethane at 0 - 20℃; for 5h; Reagent/catalyst; Mitsunobu Displacement;89.6%
With tagged 3-(diphenylphosphino)propionic acid t-butyl ester; tagged di-t-butylazodicarboxylate Yield given;
octanol
111-87-5

octanol

ethyl dihydrocinnamate
2021-28-5

ethyl dihydrocinnamate

1-octyl 3-phenylpropanoate
37826-57-6

1-octyl 3-phenylpropanoate

Conditions
ConditionsYield
[Cl(C6F13C2H4)2SnOSn(C2H4C6F13)2Cl]2 In various solvent(s) at 150℃; for 16h;100%
With sulfonated polypyrene In n-heptane at 110℃; for 6h;97%
With chloro-trimethyl-silane; diphenylammonium trifluoromethanesulfonate In toluene at 80 - 110℃; for 24h; Esterification;94%
With high p-toluenesulfonate content diphenylamine and terephthalaldehyde resin In neat (no solvent) at 110℃; for 24h;94%
octanol
111-87-5

octanol

3-Phenylpropionic acid
501-52-0

3-Phenylpropionic acid

1-octyl 3-phenylpropanoate
37826-57-6

1-octyl 3-phenylpropanoate

Conditions
ConditionsYield
With [Cl(C6F13C2H4)2SnOSn(C2H4C6F13)2Cl]2 In various solvent(s) at 150℃; for 10h;100%
With sulfonated polypyrene In n-heptane at 110℃; for 2h;98%
With trifluorormethanesulfonic acid at 80℃; for 18h; Reagent/catalyst; Temperature; Sealed tube;98%
octanol
111-87-5

octanol

benzoic acid anhydride
93-97-0

benzoic acid anhydride

n-octyl benzoate
94-50-8

n-octyl benzoate

Conditions
ConditionsYield
erbium(III) triflate In acetonitrile at 50℃; for 0.5h;100%
With bismuth(lll) trifluoromethanesulfonate In acetonitrile for 0.416667h; Heating;97%
Sulfate; tin(IV) oxide In acetonitrile at 20℃; for 3h;90%
octanol
111-87-5

octanol

ethyl dihydrocinnamate
2021-28-5

ethyl dihydrocinnamate

A

ethanol
64-17-5

ethanol

B

1-octyl 3-phenylpropanoate
37826-57-6

1-octyl 3-phenylpropanoate

Conditions
ConditionsYield
2[{Cl(C6F13CH2CH2)2SnOSn(CH2CH2C6F13)2Cl}2] In various solvent(s) at 150℃; for 16h;A n/a
B 100%
octanol
111-87-5

octanol

2,2-dimethylpropanoic anhydride
1538-75-6

2,2-dimethylpropanoic anhydride

1-octyl 2,2-dimethylpropanoate
27751-88-8

1-octyl 2,2-dimethylpropanoate

Conditions
ConditionsYield
erbium(III) triflate In acetonitrile at 20℃; for 0.416667h;100%
With magnesium(II) perchlorate at 40℃; for 5h;99%
With erbium(III) chloride at 50℃; for 2h;99%
With bismuth(lll) trifluoromethanesulfonate In dichloromethane; water at 25℃; for 4h;98%
octanol
111-87-5

octanol

propionic acid anhydride
123-62-6

propionic acid anhydride

octyl propionate
142-60-9

octyl propionate

Conditions
ConditionsYield
erbium(III) triflate In acetonitrile at 20℃; for 0.25h;100%
With erbium(III) chloride at 50℃; for 1.5h;99%
With magnesium(II) perchlorate at 20℃; for 0.5h;98%
octanol
111-87-5

octanol

4-(4-Carboxy-butoxy)-benzoic acid
35005-21-1

4-(4-Carboxy-butoxy)-benzoic acid

4-(4-octyloxycarbonyl-butoxy)-benzoic acid

4-(4-octyloxycarbonyl-butoxy)-benzoic acid

Conditions
ConditionsYield
With [Cl(C6F13C2H4)2SnOSn(C2H4C6F13)2Cl]2 In various solvent(s) at 150℃; for 16h;100%
octanol
111-87-5

octanol

benzylamine
100-46-9

benzylamine

N-benzyl-N-octylamine
1667-16-9

N-benzyl-N-octylamine

Conditions
ConditionsYield
Stage #1: octanol With 2,2,6,6-tetramethyl-piperidine-N-oxyl; [bis(acetoxy)iodo]benzene In dichloromethane for 16h;
Stage #2: benzylamine With sodium tetrahydroborate In dichloromethane chemoselective reaction;
100%
With potassium carbonate; bis[dichloro(pentamethylcyclopentadienyl)iridium(III)] In toluene at 90℃; for 17h;88%
With sodium hydrogencarbonate; bis[dichloro(pentamethylcyclopentadienyl)iridium(III)] In toluene at 90℃; for 17h;86%

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111-87-5Relevant articles and documents

Nametkin,Tanewa

, (1943)

Regioselective addition of stannylcyanocuprates to acetylenic ethers: A chemical and spectroscopic study

Cabezas,Oehlschlager

, p. 432 - 442 (1994)

The reactions of acetylenic ether 1 with higher order cuprates 2a, 2b and 2c were studied chemically and spectroscopically. Conditions were developed to efficiently and regioselectively prepare α- and β-stannylvinyl ethers. 1H and 13C NMR studies of these reactions suggest that in the presence of HMPA, higher order stannylcyanocuprate, (Bu3Sn)2Cu(CN)Li2, 2a, exists in equilibrium with Gilman cuprate, (Bu3Sn)2CuLi.

Highly selective and stable ZnO-supported bimetallic RuSn catalyst for the hydrogenation of octanoic acid to octanol

Hidajat, Marcel Jonathan,Hwang, Dong-Won,Yun, Gwang-Nam

, (2021)

The chemoselective hydrogenation of biomass-derived carboxylic acids is promising for the development of biorefineries. Herein, the selective conversion of octanoic acid to octanol over bimetallic RuSn/ZnO in a fixed-bed continuous reactor system, is reported. Almost complete conversion (99.4 %) of octanoic acid was achieved, with a remarkably high selectivity to octanol (93.0 %), when using specific reaction conditions (300°C, a weight hourly space velocity (WHSV) of 2 h?1, and 30 atm H2). Characterizations of the catalysts by BET, CO pulse chemisorption, ICP-AES, XRD, XPS and STEM-EDS revealed that the addition of Sn to Ru/ZnO resulted in the formation of a Ru3Sn7 alloy phase as well as SnOx. Comparison with Ru/ZnO catalyst gives an insight that the presence of Ru3Sn7 alloy was most likely the active site and it significantly improved the hydrogenation activity and selectivity to octanol. The SnOx and ZnO favored the formation of octyl octanoate by esterification of the formed octanol and octanoic acid, although it was successfully suppressed by optimizing the reaction conditions. Long-term stability tests revealed that RuSn/ZnO retained its activity for 1000 h with no coke formation. This study reveals the potential of RuSn/ZnO for the valorization of medium-chain fatty acids into value-added chemicals.

A facile zirconium(IV) chloride catalysed selective deprotection of t-butyldimethylsilyl (TBDMS) ethers

Sharma,Srinivas,Radha Krishna, Palakodety

, p. 4689 - 4691 (2003)

A simple and efficient protocol for the selective deprotection of t-butyldimethylsilyl (TBDMS) ethers using 20 mol% ZrCl4 in 20-45 min and in high yields, is reported, wherein it is demonstrated that acid and base sensitive groups and allylic and benzylic groups are unaffected.

Intrinsic isotope effects suggest that the reaction coordinate symmetry for the cytochrome P-450 catalyzed hydroxylation of octane is isozyme independent

Jones,Rettie,Trager

, p. 1242 - 1246 (1990)

The mechanism of the ω-hydroxylation of octane by three catalytically distinct, purified forms of cytochrome P-450, namely, P-450(b), P-450(c), and P-450(LM2), was investigated by using deuterium isotope effects. The deuterium isotope effects associated with the ω-hydroxylation of octane-1,1,1-2H3, octane-1,8-2H2, and octane-1,1,8,8-2H4 by all three isozymes were determined. From these data the intrinsic isotope effects were calculated and separated into their primary and secondary components. The primary intrinsic isotope effect for the reaction ranged from 7.69 to 9.18 while the secondary intrinsic isotope effect ranged from 1.13 to 1.25. Neither the primary nor secondary isotope effect values were statistically different for any of the isozymes investigated. These data are consistent with a symmetrical transition state for a mechanism involving initial hydrogen atom abstraction followed by hydroxyl radical recombination which is essentially independent of the specific isozyme catalyzing the reaction. It is concluded that (1) in general the porphyrin-[FeO]3+ complex behaves as a source of a triplet-like oxygen atom, (2) the regioselectivity for the site of oxidation is dictated by the apoprotein of the specific isozyme of cytochrome P-450 catalyzing the reaction, and (3) the maximum primary intrinsic isotope effect for any cytochrome P-450 catalyzed oxidation of a carbon center is about 9, assuming no tunneling effects.

-

Gingras,Waters

, p. 3508,3511 (1954)

-

2-pyridylsilyl group as a multifunctional 'phase tag' for solution phase synthesis

Yoshida, Jun-ichi,Itami, Kenichiro,Mitsudo, Koichi,Suga, Seiji

, p. 3403 - 3406 (1999)

2-Pyridyldimethylsilyl (2-PyMe2Si) group was found to serve as effective 'phase tag' for acid-base extraction for solution phase synthesis. Acid-base extraction of octyl(2-pyridyl)dimethylsilane gave rise to 98% recovery. The introduction of 2-PyMe2Si group to organic molecules was easily accomplished by Rh catalyzed hydrosilylation of alkenes with 2- PyMe2SiH. The removal of 2-PyMe2Si group was achieved by the oxidation with H2O2/KF (Tamao oxidation). In order to demonstrate the utility of 2- PyMe2Si group as a 'phase tag', a sequential multi-step transformation was conducted. The products of each steps were easily isolated by acid-base extraction, and were sufficiently pure for the direct use in the next step of the sequence.

Novel Cu and Cu2In/aluminosilicate type catalysts for the reduction of biomass-derived volatile fatty acids to alcohols

Harnos, Szabolcs,Onyestyak, Gyoergy,Barthos, Robert,Valyon, Jozsef,Stolcova, Magdalena,Kaszonyi, Alexander

, p. 1954 - 1962,9 (2012)

This work relates to the consecutive reduction of short chain carboxylic acids (volatile fatty acids, VFAs) to alcohols as main products. Acetic acid (AA) was used as a reactant to model the VFAs that can be produced by either thermochemical or biological biomass degradation. The amorphised zeolite supported copper catalysts (Cu/SiAl), especially the In-modified CuIn/SiAl catalysts, showed high hydroconversion activity and selectivity for alcohol, ester and aldehyde. Catalysts containing dispersed copper particles in amorphous aluminosilicate were obtained by dehydrating and H2-reducing Cu-forms of low-silica synthetic zeolites (A, X, P). The activity of the highly destructed Cu-aluminosilicates was found to depend on the structure of the zeolite precursor. The formation of ethyl acetate could be suppressed by adding water to the AA feed and by modifying the catalyst, e.g. by In2O 3 additive. In the catalysts modified by In2O3 additive formation of copper-indium alloy phase (Cu2In intermetallic compound) was detected resulting in a different selectivity than the one recorded for the Cu/SiAl.

Modulation of photodeprotection by the sunscreen protocol

Eivgi, Or,Levin, Efrat,Lemcoff, N. Gabriel

, p. 740 - 743 (2015)

A protocol for the selective photoremoval of alcohol protecting groups modulated by the presence of auxiliary light absorbing molecules is presented. Thus, by this method, a single light source was used to selectively remove a specific protecting group in the presence of another chromophore with a lower molar absorption coefficient. The use of a molecular sunscreen, either internal or external, was found to be crucial to achieve high selectivities.

Smith

, p. 25,39 (1974)

Pentaco-ordinate Silicon Compounds in Synthesis: Chemo- and Stereo-selective Reduction of Carbonyl Compounds using Trialkoxy-substituted Silanes and Alkali Metal Alkoxides

Hosomi, Akira,Hayashida, Hisashi,Kohra, Shinya,Tominaga, Yoshinori

, p. 1411 - 1412 (1986)

Carbonyl compounds are reduced with trialkoxy-substituted silane to the corresponding alcohols chemo- and stereo-selectively in the presence of alkali metal alkoxide under mild conditions; reduction occurs very smoothly by using an alkoxide derived from pinacol as a bidentate ligand.

Bacterial CYP153A monooxygenases for the synthesis of omega-hydroxylated fatty acids

Honda Malca, Sumire,Scheps, Daniel,Kuehnel, Lisa,Venegas-Venegas, Elena,Seifert, Alexander,Nestl, Bettina M.,Hauer, Bernhard

, p. 5115 - 5117 (2012)

CYP153A from Marinobacter aquaeolei has been identified as a fatty acid ω-hydroxylase with a broad substrate range. Two hotspots predicted to influence substrate specificity and selectivity were exchanged. Mutant G307A is 2- to 20-fold more active towards fatty acids than the wild-type. Residue L354 is determinant for the enzyme ω-regioselectivity.

Nickel catalyzed hydroboration with catecholborane

Kabalka,Narayana,Reddy

, p. 1019 - 1023 (1994)

Hydroborations of alkenes and alkyne with catecholborane were found to be catalyzed by activated nickel powder.

Deprotection of Acetals and Silyl Ethers Using Some ?-Acceptors

Tanemura, Kiyoshi,Suzuki, Tsuneo,Horaguchi, Takaaki

, p. 290 - 292 (1994)

Hydrolysis of dodecanol dimethyl acetal and dodecyl silyl ethers in MeCN-H2O was examined using a catalytic silyl amount of ?-acceptors such as 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ), tetracyanoethylene (TCNE), 7,7,8,8-tetracyanoquinodimethane (TCNQ), 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane (TCNQF4), and chloranil (CA).Cleavage of dodecyl triethylsilyl ether with TCNQ and CA was caused by room light.By application of DDQ-catalyzed deprotection of acetals to hydrolysis of tetrahydropyranyl ethers, the corresponding alcohols were obtained in quantitative yields.

Effects of Organic Modifiers on a Palladium Catalyst in the Competitive Hydrogenation of 1-Octene Versus Octanal: An Evaluation of Solid Catalysts with an Ionic Liquid Layer

Miller, Stuart F.,Friedrich, Holger B.,Holzapfel, Cedric W.,Dasireddy, Venkata D. B. C.

, p. 2628 - 2636 (2015)

The competitive hydrogenation between 1-octene and octanal has been investigated with a ≈5% palladium on alumina catalyst prepared in situ with the following organic modifiers: pyridine, 1-methylimidazole, 1,3-dimethylimidazole methylsulfate, 1,3-dimethylimidazole bis(trifluoromethylsulfonyl)imide and methyltri-sec-butylphosphonium methylsulfate. The results of these investigations indicate that the ionic liquid modifiers have significant and specific effects on catalytic performance, for example, certain systems can completely suppress octanal conversion. In addition, analytical techniques reveal that the matrix and quantity of organic species on the used catalysts are different if different ionic liquids are used as modifiers. Surface studies also reveal that the modifiers have a noticeable effect on the crystallite size and chemisorption properties of the catalysts.

Highly active and selective platinum(0)-carbene complexes. Efficient, catalytic hydrosilylation of functionalised olefins

Marko, Istvan E.,Sterin, Sebastien,Buisine, Olivier,Berthon, Guillaume,Michaud, Guillaume,Tinant, Bernard,Declercq, Jean-Paul

, p. 1429 - 1434 (2004)

Readily available N-heterocyclic platinum-carbene complexes 1 are highly efficient catalysts for the regioselective hydrosilylation of alkenes. These novel organometallics tolerate a wide range of functional and protecting groups, can be stored for prolonged periods of time and are particularly active (TON > 106).

Improving the catalytic behavior of Ni/Al2O3 by indium in reduction of carboxylic acid to alcohol

Onyestyák, Gy?rgy,Harnos, Szabolcs,Kalló, Dénes

, p. 184 - 188 (2011)

Octanoic acid (OA) was used as reactant with medium chain length to model the aliphatic carboxylic acids which can be produced by catalytic, thermochemical or biological degradation of biomass. A flow through reactor was applied at 21 bar total pressure (in general 20 bar hydrogen and 1 bar octanoic acid partial pressures) and 240-360°C. Fatty acid conversion activity of alumina supported Ni catalysts and the yield of selectively produced alcohol can be increased drastically by In2O3 doping. Appearance of metallic indium can effectively direct the step by step catalytic reduction to alcohol formation over partly reduced Ni catalysts instead of chain shortening hydrodecarbonylation. On comparing a commercial, conventionally used Adkins catalyst (consisting of 72 wt.% CuCr2O4 and 28 wt.% CuO) and novel bimetallic alumina supported composite (InNi/Al2O 3) producing alcohol with high selectivity, the chromium-free, environmental benign hydrogenation catalyst seems to be much more active.

Alkyne [2 + 2 + 2] Cyclotrimerization Catalyzed by a Low-Valent Titanium Reagent Derived from CpTiX3 (X = Cl, O- i-Pr), Me3SiCl, and Mg or Zn

Okamoto, Sentaro,Yamada, Takeshi,Tanabe, Yu-Ki,Sakai, Masaki

, p. 4431 - 4438 (2018)

Inter-, partially intra-, and intramolecular [2 + 2 + 2] cycloadditions of alkynes were catalyzed by a low-valent titanium species generated in situ from the reduction of CpTi(O-i-Pr)3, CpTiCl3, or Cp?TiCl3 with Mg or Zn powder in the presence of Me3SiCl. The role of Me3SiCl as an additive in the reaction mechanism is discussed.

Amides as Nucleophiles: Reaction of Alkyl Halides with Amides or with Amides and Water. A New Look at an Old Reaction

Brace, Neal O.

, p. 1804 - 1811 (1993)

Heating of formamide with an alkyl halide (with or without water) affords a mild, nonhydrolytic, high-yield synthesis of alcohols and formate esters.Yet the way in which substitution on the alkyl halide actually occurs remains obscure.To explore this question, thermal reaction of 1-bromooctane (1a) with formamides (HC(O)NHR, R=H, Me; 2a, 2b) was studied quantitatively.Major products are 1-octanol (3) and n-octyl formate (5); minor products are 1-octene (4), di-n-octyl ether (6), and N-octylformamide (7, from 2a, only).Solid coproduct is HC(=NR)NHR + Br(1-) (e.g., 8a, R=H, methanimidamide hydrobromide).Analogously, 1a and N-methylformamide (2b) give alkylated products 3,5, and 6 along with 8b (R=Me). 1-Iodooctane (1b) reacts similarly.Probe samples show that 1-octanol (3) is first formed, followed by 5 and 6.Occurence of 8a-c is key to a mechanistic interpretation of the reaction.An imidate ("salt I"), e.g., from 1a and 2b, is first formed and reacts with amide 2b to give and 3.Now alcohol 3 is converted to ester 5 and 8b by reaction with this same formylamidine.Water, if present, adds to the imidate and gives a new tetrahedral intermediate that cleaves to ester 5 and amide salt, RNH3X.Analogous reaction steps are proposed to generate side products 4, 6, and 7.Alkylation of formamide by C6F13CH2CH2I (1c) is considerably slower and less efficient than alkylation by 1-bromooctane.This result stands in sharp contrast to fast, efficient reaction of 1c with N-methylformamide or with DMF and water.

Thexylchloroborane. A Versatile Reagent for the Preparation of Mixed Thexyldiorganoboranes

Zweifel, George,Pearson, Norman R.

, p. 5919 - 5920 (1980)

-

Unveiling the dual role of the cholinium hexanoate ionic liquid as solvent and catalyst in suberin depolymerisation

Ferreira, Rui,Garcia, Helga,Sousa, Andreia F.,Guerreiro, Marina,Duarte, Filipe J. S.,Freire, Carmen S. R.,Calhorda, Maria Jose,Silvestre, Armando J. D.,Kunz, Werner,Rebelo, Luis Paulo N.,Silva Pereira, Cristina

, p. 2993 - 3002 (2014)

Disruption of the three-dimensional network of suberin in cork by cholinium hexanoate leads to its efficient and selective isolation. The reaction mechanism, which likely involves selective cleavage of some inter-monomeric bonds in suberin, was still unanswered. To address this question, the role of the ionic liquid during suberin depolymerisation and during cleavage of standard compounds carrying key chemical functionalities was herein investigated. A clear demonstration that the ionic liquid catalyses the hydrolysis of acylglycerol ester bonds was attained herein, both experimentally and computationally (DFT calculations). This behaviour is related to cholinium hexanoate capacity to activate the nucleophilic attack of water. The data showed also that the most favourable reaction is the hydrolysis of acylglycerol ester bonds, with the C2 position reporting the faster kinetics, whilst most of the linear aliphatic esters remained intact. The study emphasises that the ionic liquid plays the dual role of solvent and catalyst and leads to suberin efficient extraction through a mild depolymerisation. It is also one of the few reports of ionic liquids as efficient catalysts in the hydrolysis of esters.

MOF-derived Cu@C catalyst for the liquid-phase hydrogenation of esters

Zhao, Yujun,Wu, Xiaoqian,Zhou, Jiahua,Wang, Yue,Wang, Shengping,Ma, Xinbin

, p. 883 - 886 (2018)

MOF derived core-shell Cu@C was prepared by the pyrolysis of Cu-BTC and applied in the liquid-phase hydrogenation of ester. The severe aggregation of copper species was inhibited by the carbon shell. Compared with traditional Cu/AC-H2 catalyst, Cu@C-N2 displayed higher activity in the hydrogenation of butyl butyrate due to its higher Cu dispersion. Further reduction of Cu@C-N2 catalyst in H2 greatly improved the activity, as a result of the appropriate ratio of Cu+/Cu0, which can activate both ester and H2 molecules.

Electrocatalytic hydrogenation of octyl aldehyde over Pd catalysts

Cirtiu, Ciprian M.,Menard, Hugues

, p. 475 - 478 (2007)

The electrocatalytic hydrogenation (ECH) of octyl aldehyde (octanal) to octyl alcohol (octan-1-ol) was investigated using commercial Pd/alumina catalysts in aqueous ethanol. The influence of different parameters, such as catalyst support, current intensity, polarity of solvent, supporting electrolyte, and octanal concentration, on the electrocatalytic hydrogenation of octanal was studied.

A Remarkably Simple Class of Imidazolium-Based Lipids and Their Biological Properties

Wang, Da,Richter, Christian,Rühling, Andreas,Drücker, Patrick,Siegmund, Daniel,Metzler-Nolte, Nils,Glorius, Frank,Galla, Hans-Joachim

, p. 15123 - 15126 (2015)

A series of imidazolium salts bearing two alkyl chains in the backbone of the imidazolium core were synthesized, resembling the structure of lipids. Their antibacterial activity and cytotoxicity were evaluated using Gram-positive and Gram-negative bacteria and eukaryotic cell lines including tumor cells. It is shown that the length of alkyl chains in the backbone is vital for the antibiofilm activities of these lipid-mimicking components. In addition to their biological activity, their surface activity and their membrane interactions are shown by film balance and quartz crystal microbalance (QCM) measurements. The structure-activity relationship indicates that the distinctive chemical structure contributes considerably to the biological activities of this novel class of lipids. Lipids! A series of imidazolium salts bearing two alkyl chains in the backbone were synthesized, resembling the structure of lipids. The biological activity resulting from their surface activity and membrane interaction are shown (see figure), which were determined by the alkyl chain length.

Novel hydroborating agents from Silylamine-boranes

Soderquist, John A.,Medina, Jesus R.,Huertas, Ramon

, p. 6119 - 6122 (1998)

Exhibiting a broad spectrum of hydroboration reactivities, seven (7) new silylamine-borane complexes (1) were efficiently prepared from diborane and the corresponding silylated amines (2). Most are crystalline solids which are air-stable, concentrated borane sources. All provide convenient alternatives to other hydroborating agents, 2 undergoing complete hydrolysis to volatile and/or water soluble by-products upon aqueous work-up, thereby greatly facilitating the isolation of the borane-derived reaction products.

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.

KB3H8: An environment-friendly reagent for the selective reduction of aldehydes and ketones to alcohols

Li, Xinying,Mi, Tongge,Guo, Wenjing,Ruan, Zhongrui,Guo, Yu,Ma, Yan-Na,Chen, Xuenian

supporting information, p. 12776 - 12779 (2021/12/10)

Selective reduction of aldehydes and ketones to their corresponding alcohols with KB3H8, an air- and moisture-stable, nontoxic, and easy-to-handle reagent, in water and THF has been explored under an air atmosphere for the first time. Control experiments illustrated the good selectivity of KB3H8 over NaBH4 for the reduction of 4-acetylbenzaldehyde and aromatic keto esters. This journal is

PROCESS FOR PRODUCING A CATALYST, CATALYST AND USE THEREOF

-

Page/Page column 13-15; 17, (2021/06/26)

A process for producing a supported catalyst comprising metal nanoparticles, said process comprises the following steps: (a) preparing a supported catalyst comprising metal nanoparticles; (b) peducing the catalyst of step (a); (c) treating the reduced catalyst of step (b) with at least one alcohol, and (d) calcining the treated catalyst of step (c) to remove carbon species, to produce said supported catalyst. A catalyst obtainable from this process can be used in amination, hydrogenation, dehydrogenation, hydrogenolysis and aerobic oxidation reactions.

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