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589-98-0

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589-98-0 Usage

Description

3-Octanol has a sweet, nutty, warm, herbaceous odor. Can be prepared in the racemic form by reduction of ethyl-n-amyl ketone with sodium in ether solution.

Chemical Properties

Different sources of media describe the Chemical Properties of 589-98-0 differently. You can refer to the following data:
1. 3-Octanol has a sweet, oily, nutty, warm, herbaceous odor.
2. Clear colorless liquid
3. 3-Octanol may occur in its optically active form. It is a colorless liquid that has a mushroomy–earthy odor and occurs in mushrooms. 3-Octanol can be obtained by hydrogenation of 3-octanone; it is used in lavender compositions and for impartingmushroom-like odors.

Occurrence

It has been identified (free and esterified) in a variety of mint; also reported in lavender and the essential oils of Mentha arvenis var. piperascens and Mentha spicata. Also reported found in apple, banana, cranberry, grapes, papaya, strawberry, sourcherry, lemon, blackberry, Swiss cheese, pork, peas, potato, ginger, Mentha oils, thyme, fish, fried beef, cognac, rum, grape wines, coffee, tea, oats, soybean, mushroom, sweet marjoram, kelp, buckwheat, lemon balm, dried bonito, truffle, passionfruit and pepino fruit (Solanum muricatum).

Uses

Different sources of media describe the Uses of 589-98-0 differently. You can refer to the following data:
1. 3-Octanol is a liquid produced by hydrogenation of ethyl namyl ketone. It is used in fragrances and as an artificial flavoring in foods.
2. 3-Octanol was used as reference compound in detection of volatile metabolites from five fungal species cultivated on two media.
3. 3-Octanol may be used as a reference standard in the determination of the analyte in herb plants using gas chromatography coupled with mass spectrometry (GC-MS).

Preparation

Can be prepared in the racemic form by reduction of ethyl-n-amyl ketone with sodium in ether solution.

Aroma threshold values

Detection: 18 to 250 ppb. Aroma characteristics at 5.0%: earthy, mushroom, diry, musty, creamy, waxy with a slight fermented green minty nuance.

Taste threshold values

Taste characteristics at 5 ppm: musty, mushroom, earthy, creamy dairy, dirty with an herbal, minty nuance.

General Description

Influence of environment of the TiO2 photocatalyst on the rate of photocatalytic oxidation of liquid 3-octanol has been investigated.

Flammability and Explosibility

Notclassified

Biochem/physiol Actions

Taste at 10 ppm

Safety Profile

A moderate skin and eye irritant. When heated to decomposition it emits acrid smoke and irritating fumes.

Check Digit Verification of cas no

The CAS Registry Mumber 589-98-0 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,8 and 9 respectively; the second part has 2 digits, 9 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 589-98:
(5*5)+(4*8)+(3*9)+(2*9)+(1*8)=110
110 % 10 = 0
So 589-98-0 is a valid CAS Registry Number.
InChI:InChI=1/C8H18O/c1-3-5-6-7-8(9)4-2/h8-9H,3-7H2,1-2H3/t8-/m0/s1

589-98-0 Well-known Company Product Price

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  • Alfa Aesar

  • (A14488)  3-Octanol, 97%   

  • 589-98-0

  • 50g

  • 435.0CNY

  • Detail
  • Alfa Aesar

  • (A14488)  3-Octanol, 97%   

  • 589-98-0

  • 250g

  • 2122.0CNY

  • Detail

589-98-0SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name 3-octanol

1.2 Other means of identification

Product number -
Other names OCTANOL,3

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:589-98-0 SDS

589-98-0Synthetic route

1-octen-3-ol
3391-86-4

1-octen-3-ol

rac-3-octanol
589-98-0

rac-3-octanol

Conditions
ConditionsYield
With sodium tetrahydroborate; C11H18Cl2CoN2S; hydrogen In isopropyl alcohol at 100℃; under 37503.8 Torr; for 16h; Reagent/catalyst; Solvent; Glovebox; Autoclave;98%
With hydrogen In ethanol at 20℃; under 760.051 Torr; for 1h; chemoselective reaction;94%
Stage #1: 1-octen-3-ol With lithium triethylborohydride; cobalt(II) bromide In tetrahydrofuran Inert atmosphere; Glovebox;
Stage #2: With hydrogen In tetrahydrofuran at 20℃; under 1500.15 Torr; for 3h;
93%
2-(1-ethyl-hexyloxy)-tetrahydro-pyran

2-(1-ethyl-hexyloxy)-tetrahydro-pyran

rac-3-octanol
589-98-0

rac-3-octanol

Conditions
ConditionsYield
With dimethylbromosulphonium bromide In methanol; dichloromethane at 20℃; for 0.416667h;92%
With zinc tetrafluoroborate In methanol; dichloromethane; water at 20℃; for 0.416667h;92%
3-(t-butyldimethylsiloxy)octane
141090-46-2

3-(t-butyldimethylsiloxy)octane

rac-3-octanol
589-98-0

rac-3-octanol

Conditions
ConditionsYield
With acetonyltriphenylphosphonium bromide In methanol; dichloromethane at 20℃; for 0.366667h;91%
With titanium tetrachloride; ethyl acetate In chlorobenzene at -18℃; for 0.5h;
3-octanone
106-68-3

3-octanone

rac-3-octanol
589-98-0

rac-3-octanol

Conditions
ConditionsYield
With isopropyl alcohol at 80℃; for 24h; Inert atmosphere;85%
With C29H34BNOP2Ru In ethanol; dichloromethane Schlenk technique; Inert atmosphere; Reflux;80%
With ammonium hydroxide; sodium tetrahydroborate In ethanol; water for 3h; Ambient temperature;79.02%
Conditions
ConditionsYield
With (η(5)-C5Me5)RuCl(1,3-bis(cyclohexyl)imidazol-2-ylidene); sodium t-butanolate In toluene at 20℃;84%
With C32H42N2ORu In toluene at 50℃;82%
1-octen-3-ol
3391-86-4

1-octen-3-ol

A

3-octanone
106-68-3

3-octanone

B

rac-3-octanol
589-98-0

rac-3-octanol

Conditions
ConditionsYield
With sodium carbonate decahydrate; dichlororuthenium(II) (p-cymene)(1,3,5-triaza-7-phosphaadamantane); hydrogen In water at 75℃; under 750.075 Torr; pH=7; Catalytic behavior; Schlenk technique;A 81%
B 17%
With Fe(bis[(diisopropylphosphino)ethyl]amine)(CO)(H)(BH4); potassium tert-butylate; isopropyl alcohol at 80℃; for 1h; Catalytic behavior; Reagent/catalyst; Inert atmosphere;A 28%
B 60%
With isopropyl alcohol under 760.051 Torr; for 2h; Inert atmosphere; Heating;A 6 %Chromat.
B 94 %Chromat.
ethylmagnesium bromide
925-90-6

ethylmagnesium bromide

hexanal
66-25-1

hexanal

rac-3-octanol
589-98-0

rac-3-octanol

Conditions
ConditionsYield
In diethyl ether at 0 - 20℃;53%
1-ethylhexyl acetate
4864-61-3

1-ethylhexyl acetate

rac-3-octanol
589-98-0

rac-3-octanol

Conditions
ConditionsYield
With ethanol at 90℃; under 10343.2 Torr; for 16h; Catalytic behavior; Inert atmosphere;44%
With carbon-supported single-site molybdenum dioxo In ethanol at 90℃; under 10343.2 Torr; for 16h; Time; Inert atmosphere;44 %Spectr.
octane
111-65-9

octane

A

3-octanone
106-68-3

3-octanone

B

octan-4-one
589-63-9

octan-4-one

C

octan-4-ol
589-62-8

octan-4-ol

D

rac-3-octanol
589-98-0

rac-3-octanol

E

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

rac-octan-2-ol

F

hexyl-methyl-ketone
111-13-7

hexyl-methyl-ketone

Conditions
ConditionsYield
With [PPh4]2[MnV(N)(CN)4]; tetrabutylammonium periodite; acetic acid In 2,2,2-trifluoroethanol at 23℃; Inert atmosphere;A 14%
B 14%
C 18%
D 18%
E 20%
F 16%
With [PPh4]2[MnV(N)(CN)4]; dihydrogen peroxide; acetic acid In 2,2,2-trifluoroethanol at 23℃; for 5h; Inert atmosphere;A 14%
B 14%
C 18%
D 19%
E 17%
F 15%
With Co(III)(BPI)(OAc)(OO-tBu) at 60℃; for 2h; Product distribution; stoichiometric oxidation by various cobalt(III)alkylperoxy complexes; further products;A 7.8%
B 8.3%
C 4.6%
D 5%
E 7%
F 12%
pentylmagnesium chloride
6393-56-2

pentylmagnesium chloride

propionaldehyde
123-38-6

propionaldehyde

rac-3-octanol
589-98-0

rac-3-octanol

Conditions
ConditionsYield
With diethyl ether
n-pentylmagnesium bromide
693-25-4

n-pentylmagnesium bromide

propionaldehyde
123-38-6

propionaldehyde

rac-3-octanol
589-98-0

rac-3-octanol

Conditions
ConditionsYield
With diethyl ether
ethylmagnesium iodide
10467-10-4

ethylmagnesium iodide

hexanal
66-25-1

hexanal

rac-3-octanol
589-98-0

rac-3-octanol

buta-1,3-diene
106-99-0

buta-1,3-diene

rac-3-octanol
589-98-0

rac-3-octanol

Conditions
ConditionsYield
ueber (+-)-3-Acetoxy-octan;
2,3-epoxyoctane
3234-26-2

2,3-epoxyoctane

A

rac-3-octanol
589-98-0

rac-3-octanol

B

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

rac-octan-2-ol

Conditions
ConditionsYield
With chloro-trimethyl-silane; zinc In dichloromethane for 0.0833333h; Ambient temperature; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
octane
111-65-9

octane

A

octanol
111-87-5

octanol

B

octan-4-ol
589-62-8

octan-4-ol

C

rac-3-octanol
589-98-0

rac-3-octanol

D

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

rac-octan-2-ol

Conditions
ConditionsYield
With iodosylbenzene; MnTTPPP(OAc) In benzene at 25℃; for 7h; Mechanism; other catalysts and regioselectivity investigated;
With potassium hydroxide; dihydrogen peroxide 1.) ethyl acetate, 5 h, irradiation; 2.) methanol, 4 h, reflux; Yield given. Multistep reaction. Yields of byproduct given;
With dihydrogen peroxide; chromic acid In acetonitrile at 60℃; under 750.06 Torr; for 1h; Product distribution;
octane
111-65-9

octane

A

octanol
111-87-5

octanol

B

rac-3-octanol
589-98-0

rac-3-octanol

C

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

rac-octan-2-ol

Conditions
ConditionsYield
With isozyme P-450b for 0.166667h; Product distribution; Mechanism; P-450 reductase, NADPH, phosphatidylcholine (pH 8.2); var. isozymes of cytochrome P-450;
With cytochrome P450 BM3 from Bacillus megaterium 77-9H mutation; oxygen; NADPH In phosphate buffer; ethanol at 25℃; under 1050.08 Torr; for 12h; pH=8.0; Title compound not separated from byproducts;
With cytochrome P450 BM-3 enzyme mutant 12-10C; nicotinamide adenine dinucleotide phosphate In aq. phosphate buffer; ethanol pH=8.0; Catalytic behavior; Kinetics; Reagent/catalyst; Enzymatic reaction;
With cytochrome P450 BM-3 enzyme mutant 29-3E; nicotinamide adenine dinucleotide phosphate In aq. phosphate buffer; ethanol pH=8.0; Catalytic behavior; Kinetics; Reagent/catalyst; Enzymatic reaction; regiospecific reaction;
octane
111-65-9

octane

A

3-octanone
106-68-3

3-octanone

B

octan-4-one
589-63-9

octan-4-one

C

octan-4-ol
589-62-8

octan-4-ol

D

rac-3-octanol
589-98-0

rac-3-octanol

Conditions
ConditionsYield
With (pyridine-2-carboxylate)VO(O2)(H2O)2 In acetonitrile at 20℃; for 5h; Further byproducts given;A 2.9 % Chromat.
B 2.8 % Chromat.
C 0.5 % Chromat.
D 0.5 % Chromat.
octane
111-65-9

octane

A

3-octanone
106-68-3

3-octanone

B

octan-4-one
589-63-9

octan-4-one

C

rac-3-octanol
589-98-0

rac-3-octanol

D

hexyl-methyl-ketone
111-13-7

hexyl-methyl-ketone

Conditions
ConditionsYield
With (pyridine-2-carboxylate)VO(O2)(H2O)2 In acetonitrile at 20℃; for 5h; Further byproducts given;A 2.9 % Chromat.
B 2.8 % Chromat.
C 0.5 % Chromat.
D 2.4 % Chromat.
octane
111-65-9

octane

A

3-octanone
106-68-3

3-octanone

B

octan-4-ol
589-62-8

octan-4-ol

C

rac-3-octanol
589-98-0

rac-3-octanol

D

hexyl-methyl-ketone
111-13-7

hexyl-methyl-ketone

Conditions
ConditionsYield
With (pyridine-2-carboxylate)VO(O2)(H2O)2 In acetonitrile at 20℃; for 5h; Further byproducts given;A 2.9 % Chromat.
B 0.5 % Chromat.
C 0.5 % Chromat.
D 2.4 % Chromat.
With Titanium substituted ZSM-5; dihydrogen peroxide In butanone at 80℃; for 4h; Yield given. Further byproducts given. Yields of byproduct given. Title compound not separated from byproducts;
octane
111-65-9

octane

A

octan-4-one
589-63-9

octan-4-one

B

octan-4-ol
589-62-8

octan-4-ol

C

rac-3-octanol
589-98-0

rac-3-octanol

D

hexyl-methyl-ketone
111-13-7

hexyl-methyl-ketone

Conditions
ConditionsYield
With (pyridine-2-carboxylate)VO(O2)(H2O)2 In acetonitrile at 20℃; for 5h; Further byproducts given;A 2.8 % Chromat.
B 0.5 % Chromat.
C 0.5 % Chromat.
D 2.4 % Chromat.
octane
111-65-9

octane

A

octan-4-ol
589-62-8

octan-4-ol

B

rac-3-octanol
589-98-0

rac-3-octanol

C

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

rac-octan-2-ol

D

hexyl-methyl-ketone
111-13-7

hexyl-methyl-ketone

Conditions
ConditionsYield
With (pyridine-2-carboxylate)VO(O2)(H2O)2 In acetonitrile at 20℃; for 5h; Further byproducts given;A 0.5 % Chromat.
B 0.5 % Chromat.
C 1.5 % Chromat.
D 2.4 % Chromat.
With Titanium substituted ZSM-5; dihydrogen peroxide In butanone at 80℃; for 4h; Yield given. Further byproducts given. Yields of byproduct given. Title compound not separated from byproducts;
With bis(acetylacetonate)oxovanadium; dihydrogen peroxide In acetic acid at 30℃; Product distribution;
With oxygen; NADPH; CYP monooxygenase CYP102A1 mutant A74G In phosphate buffer; dimethyl sulfoxide at 20℃; for 100h; pH=6; Further byproducts given. Title compound not separated from byproducts;
2-octene
111-67-1

2-octene

A

rac-3-octanol
589-98-0

rac-3-octanol

B

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

rac-octan-2-ol

Conditions
ConditionsYield
With sodium persulfate; silver nitrate In water; acetonitrile Heating;
trans-2-Octene
13389-42-9

trans-2-Octene

A

rac-3-octanol
589-98-0

rac-3-octanol

B

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

rac-octan-2-ol

Conditions
ConditionsYield
With sodium hydrogensulfide; lithium nitrate 1.) MeCN/Et2O/H2O, 10 deg C, anodic oxidation condition; 2.) EtOH; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
Stage #1: trans-2-Octene With 2-(perfluorooctyl)ethyl methyl sulfide*BH3 In dichloromethane at 0℃; for 1h;
Stage #2: With sodium hydroxide; dihydrogen peroxide In dichloromethane; water Further stages.;
With C11H7F17S(1+)B(1-)H3; 3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecyl methyl sulfide In FC-72; dichloromethane
amyl iodide
628-17-1

amyl iodide

propyldimesitylborane
74178-57-7

propyldimesitylborane

A

rac-3-octanol
589-98-0

rac-3-octanol

B

Mesitol
527-60-6

Mesitol

Conditions
ConditionsYield
Yield given. Multistep reaction;
amyl iodide
628-17-1

amyl iodide

C21H28BLi

C21H28BLi

rac-3-octanol
589-98-0

rac-3-octanol

Conditions
ConditionsYield
With sodium hydroxide; dihydrogen peroxide 1.) THF, hexane, 0 deg C, 0.5 h, 2.) THF, hexane, methanol, 68 deg C, 72 h; Yield given. Multistep reaction;
Butane-1,4-diol
110-63-4

Butane-1,4-diol

butan-1-ol
71-36-3

butan-1-ol

A

3-hydroxymethyl-1,7-heptanediol
41796-89-8

3-hydroxymethyl-1,7-heptanediol

B

rac-3-octanol
589-98-0

rac-3-octanol

C

2-(n-butyl)-1,4-butanediol
80676-17-1

2-(n-butyl)-1,4-butanediol

D

2-(1-hydroxymethylpropyl)tetrahydrofuran
80676-15-9

2-(1-hydroxymethylpropyl)tetrahydrofuran

Conditions
ConditionsYield
With chromium(III) oxide; sodium; nickel 2) reflux, 20 h, separation of water; Yield given. Multistep reaction. Further byproducts given;
Butane-1,4-diol
110-63-4

Butane-1,4-diol

butan-1-ol
71-36-3

butan-1-ol

A

rac-3-octanol
589-98-0

rac-3-octanol

B

2-(n-butyl)-1,4-butanediol
80676-17-1

2-(n-butyl)-1,4-butanediol

C

2-(1-hydroxymethylpropyl)tetrahydrofuran
80676-15-9

2-(1-hydroxymethylpropyl)tetrahydrofuran

D

2-(1-hydroxymethyl-3-hydroxypropyl)tetrahydrofuran
73373-12-3

2-(1-hydroxymethyl-3-hydroxypropyl)tetrahydrofuran

Conditions
ConditionsYield
With chromium(III) oxide; sodium; nickel 2) reflux, 20 h, separation of water; Yield given. Multistep reaction. Further byproducts given;
octane
111-65-9

octane

A

3-octanone
106-68-3

3-octanone

B

octan-4-one
589-63-9

octan-4-one

C

rac-3-octanol
589-98-0

rac-3-octanol

D

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

rac-octan-2-ol

Conditions
ConditionsYield
With Titanium substituted ZSM-5; dihydrogen peroxide In butanone at 80℃; for 4h; Yield given. Further byproducts given. Yields of byproduct given. Title compound not separated from byproducts;
octane
111-65-9

octane

A

octan-4-one
589-63-9

octan-4-one

B

octan-4-ol
589-62-8

octan-4-ol

C

rac-3-octanol
589-98-0

rac-3-octanol

D

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

rac-octan-2-ol

Conditions
ConditionsYield
With Titanium substituted ZSM-5; dihydrogen peroxide In butanone at 80℃; for 4h; Yield given. Further byproducts given. Yields of byproduct given. Title compound not separated from byproducts;
With purified cytochrome P450 BM-3 (Bacillus megaterium); tris hydrochloride; NADPH In water; dimethyl sulfoxide at 20℃; for 2h; Enzyme kinetics; Product distribution; Further Variations:; Reagents; Enzymatic reaction;
octane
111-65-9

octane

A

octan-4-ol
589-62-8

octan-4-ol

B

rac-3-octanol
589-98-0

rac-3-octanol

C

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

rac-octan-2-ol

Conditions
ConditionsYield
With tert.-butylhydroperoxide; lithium aluminium tetrahydride; 4 A molecular sieve; manganese(IV) oxide 1) benzene, 60 deg C, 48 h, 2) Et2O, r.t.; Yield given. Multistep reaction. Yields of byproduct given;
With L188Q mutant; sol-gel immobilised P450 BM-3 A74G; NADPH In phosphate buffer; dimethyl sulfoxide for 2h; pH=7.5; Enzymatic reaction;
With NADPH In dimethyl sulfoxide at 30℃; pH=7.4; Product distribution; Further Variations:; Reagents;A 42 % Chromat.
B 43 % Chromat.
C 15 % Chromat.
rac-3-octanol
589-98-0

rac-3-octanol

citric acid
77-92-9

citric acid

tris(2-ethylhexyl)propane-1,2,3-tricarboxylate
7147-34-4

tris(2-ethylhexyl)propane-1,2,3-tricarboxylate

Conditions
ConditionsYield
With tetrabutoxytitanium at 170 - 220℃; for 4.5h; Inert atmosphere; Large scale;99%
rac-3-octanol
589-98-0

rac-3-octanol

methanesulfonyl chloride
124-63-0

methanesulfonyl chloride

3-octyl methanesulfonate

3-octyl methanesulfonate

Conditions
ConditionsYield
With 1-methyl-1H-imidazole; triethylamine In toluene at 20 - 25℃; for 1h; Inert atmosphere;98%
With trimethylamine hydrochloride; triethylamine In toluene at 0 - 5℃; for 1h;94%
With N,N,N',N'-tetramethylhexamethylenediamine In toluene at 0 - 5℃; for 1h; mesylation;94%
With triethylamine In dichloromethane at 20℃; Sealed tube;
undec-10-enoyl chloride
38460-95-6

undec-10-enoyl chloride

rac-3-octanol
589-98-0

rac-3-octanol

3-octyl 10-undecenoate

3-octyl 10-undecenoate

Conditions
ConditionsYield
With 1-methyl-1H-imidazole; N,N,N,N,-tetramethylethylenediamine In acetonitrile at 0 - 25℃; for 2h;98%
rac-3-octanol
589-98-0

rac-3-octanol

di(ethyl hexyl) amine

di(ethyl hexyl) amine

Conditions
ConditionsYield
With urea In 1,3,5-trimethyl-benzene at 141℃; under 760.051 Torr; for 20h; Inert atmosphere;98%
rac-3-octanol
589-98-0

rac-3-octanol

3-octanone
106-68-3

3-octanone

Conditions
ConditionsYield
With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium hypochlorite pentahydrate; tetra(n-butyl)ammonium hydrogensulfate In dichloromethane at 5℃; for 1h; Temperature;97%
With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium hypochlorite pentahydrate; tetra(n-butyl)ammonium hydrogensulfate In dichloromethane at 5℃; for 0.5h;96%
With 2,2,6,6-tetramethyl-piperidine-N-oxyl; periodic acid In dichloromethane at 20℃; for 0.75h;95%
rac-3-octanol
589-98-0

rac-3-octanol

2-chloropropionyl chloride
7623-09-8

2-chloropropionyl chloride

3-octyl 2-chloropropanoate

3-octyl 2-chloropropanoate

Conditions
ConditionsYield
With 1-methyl-1H-imidazole; N,N,N,N,-tetramethylethylenediamine In acetonitrile at 0 - 25℃; for 2h;97%
rac-3-octanol
589-98-0

rac-3-octanol

p-toluenesulfonyl chloride
98-59-9

p-toluenesulfonyl chloride

octan-3-yl 4-methylbenzenesulfonate
4883-87-8

octan-3-yl 4-methylbenzenesulfonate

Conditions
ConditionsYield
With N,N,N',N'-tetramethylhexamethylenediamine; triethylamine In acetonitrile at 0 - 20℃; for 4h; Tosylation;95%
With 1-methyl-1H-imidazole; triethylamine In toluene at 20 - 25℃; for 1h; Inert atmosphere;94%
With trimethylamine hydrochloride; triethylamine In dichloromethane at 0 - 5℃; for 1h;93%
rac-3-octanol
589-98-0

rac-3-octanol

aniline
62-53-3

aniline

C14H23N
343947-80-8

C14H23N

Conditions
ConditionsYield
In 5,5-dimethyl-1,3-cyclohexadiene at 130℃; for 12h; Inert atmosphere;94.7%
With [RuCl(p-cymene)(1,3-dibenzylbenzimidazolin-2-ylidene)(PPh3)]PF6 In neat (no solvent) at 130℃; for 18h; Reagent/catalyst;49%
rac-3-octanol
589-98-0

rac-3-octanol

A

3-octanone
106-68-3

3-octanone

B

1-ethylhexyl acetate
4864-61-3

1-ethylhexyl acetate

Conditions
ConditionsYield
With dihydrogen peroxide; methyltrioxorhenium(VII); sodium bromide In acetic acid for 10h; Ambient temperature;A 94%
B 6%
rac-3-octanol
589-98-0

rac-3-octanol

cyclohexanylcarbonyl chloride
2719-27-9

cyclohexanylcarbonyl chloride

3-octyl cyclohexanecarboxylate

3-octyl cyclohexanecarboxylate

Conditions
ConditionsYield
With 1-methyl-1H-imidazole; N,N,N,N,-tetramethylethylenediamine; potassium carbonate In potassium hydroxide at 20 - 25℃; for 2h; pH=11.5; Schotten-Baumann-type reaction;94%
With 1-methyl-1H-imidazole; N,N,N,N,-tetramethylethylenediamine In acetonitrile at 0 - 25℃; for 2h;94%
rac-3-octanol
589-98-0

rac-3-octanol

(S)-(-)-3,3,3-Trifluormilchsaeure
125995-00-8

(S)-(-)-3,3,3-Trifluormilchsaeure

3-octyl 3,3,3-trifluoro-2-hydroxypropionate

3-octyl 3,3,3-trifluoro-2-hydroxypropionate

Conditions
ConditionsYield
In benzene Esterification; Heating;92%
3,4-dihydro-2H-pyran
110-87-2

3,4-dihydro-2H-pyran

rac-3-octanol
589-98-0

rac-3-octanol

2-(1-ethyl-hexyloxy)-tetrahydro-pyran

2-(1-ethyl-hexyloxy)-tetrahydro-pyran

Conditions
ConditionsYield
bismuth(III) nitrate In dichloromethane at 20℃; for 0.3h;90%
With dimethylbromosulphonium bromide at 20℃; for 0.0833333h;87%
With zinc tetrafluoroborate In dichloromethane; water at 20℃; for 0.166667h;87%
maleic anhydride
108-31-6

maleic anhydride

rac-3-octanol
589-98-0

rac-3-octanol

bis(2-ethylhexyl) maleate
142-16-5

bis(2-ethylhexyl) maleate

Conditions
ConditionsYield
With sulfuric acid; 2,6-di-tert-butyl-4-hydroxytoluene In benzene at 90℃; for 2.5h; Heating / reflux;90%
rac-3-octanol
589-98-0

rac-3-octanol

3,3-dimethylbutanoic acid chloride
7065-46-5

3,3-dimethylbutanoic acid chloride

3-octyl 3,3-dimethylbutanoate

3-octyl 3,3-dimethylbutanoate

Conditions
ConditionsYield
With 1-methyl-1H-imidazole; N,N,N,N,-tetramethylethylenediamine; potassium carbonate In potassium hydroxide at 20 - 25℃; for 2h; pH=11.5; Schotten-Baumann-type reaction;89%
rac-3-octanol
589-98-0

rac-3-octanol

benzoyl chloride
98-88-4

benzoyl chloride

octan-3-yl benzoate
102245-28-3

octan-3-yl benzoate

Conditions
ConditionsYield
With 1-methyl-1H-imidazole; N,N,N,N,-tetramethylethylenediamine In acetonitrile at 0 - 25℃; for 2h;89%
With 1-methyl-1H-imidazole; N,N,N,N,-tetramethylethylenediamine; potassium carbonate In potassium hydroxide at 20 - 25℃; for 1.5h; pH=11.5; Schotten-Baumann-type reaction;72%
rac-3-octanol
589-98-0

rac-3-octanol

Natrium-n-Octylsulfat-(3)

Natrium-n-Octylsulfat-(3)

Conditions
ConditionsYield
Stage #1: rac-3-octanol With sodium hydride In 1,4-dioxane at 20℃; for 1h;
Stage #2: With triethylamine sulfurtrioxide In 1,4-dioxane at 20℃;
87%
rac-3-octanol
589-98-0

rac-3-octanol

2,2,6-trimethyl-4H-1,3-dioxin-4-one
5394-63-8

2,2,6-trimethyl-4H-1,3-dioxin-4-one

Methyl-2-n-Heptyl Acetoacetate
96453-22-4

Methyl-2-n-Heptyl Acetoacetate

Conditions
ConditionsYield
In xylene at 150℃; for 0.5h;86%
rac-3-octanol
589-98-0

rac-3-octanol

hydrocinnamic acid chloride
645-45-4

hydrocinnamic acid chloride

3-octyl 3-phenylpropanoate

3-octyl 3-phenylpropanoate

Conditions
ConditionsYield
With 1-methyl-1H-imidazole; N,N,N,N,-tetramethylethylenediamine In acetonitrile at 0 - 5℃; for 1h;86%
With 1-methyl-1H-imidazole; N,N,N,N,-tetramethylethylenediamine; potassium carbonate In potassium hydroxide at 20 - 25℃; for 1.5h; pH=11.5; Schotten-Baumann-type reaction;85%
rac-3-octanol
589-98-0

rac-3-octanol

tetradecane-1,2-diol
21129-09-9

tetradecane-1,2-diol

A

3-octanone
106-68-3

3-octanone

B

1-tetradecene
1120-36-1

1-tetradecene

Conditions
ConditionsYield
With methyltrioxorhenium(VII) In dodecane at 80 - 175℃; Catalytic behavior; Kinetics; Temperature;A n/a
B 85%
rac-3-octanol
589-98-0

rac-3-octanol

diethyl 2-[(4-methoxyphenoxy)methyl]pyrimidine-4,6-dicarboxylate

diethyl 2-[(4-methoxyphenoxy)methyl]pyrimidine-4,6-dicarboxylate

di(octan-3-yl) 2-[(4-methoxyphenoxy)methyl]pyrimidine-4,6-dicarboxylate

di(octan-3-yl) 2-[(4-methoxyphenoxy)methyl]pyrimidine-4,6-dicarboxylate

Conditions
ConditionsYield
With sulfuric acid at 100℃; for 3h; Inert atmosphere;84%
rac-3-octanol
589-98-0

rac-3-octanol

rac-3-octyl sulfate
74403-67-1

rac-3-octyl sulfate

Conditions
ConditionsYield
With triethylamine sulfur trioxide83%
With triethylamine sulfur trioxide
rac-3-octanol
589-98-0

rac-3-octanol

2-Phenylphenol
90-43-7

2-Phenylphenol

2-biphenyl 3-octyl ether

2-biphenyl 3-octyl ether

Conditions
ConditionsYield
Mitsunobu Displacement; Sonication;83%
rac-3-octanol
589-98-0

rac-3-octanol

4-methoxy-aniline
104-94-9

4-methoxy-aniline

4-methoxy-N-(octan-3-yl)aniline

4-methoxy-N-(octan-3-yl)aniline

Conditions
ConditionsYield
With Knoelker’s complex; silver fluoride In toluene at 110℃; for 48h; Inert atmosphere; Sealed tube;82%
rac-3-octanol
589-98-0

rac-3-octanol

acryloyl chloride
814-68-6

acryloyl chloride

octane-3-yl acrylate

octane-3-yl acrylate

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0℃;81%

589-98-0Relevant articles and documents

Biocatalytic synthesis of non-vicinal aliphatic diols

Ebrecht, Ana C.,Aschenbrenner, Jasmin C.,Smit, Martha S.,Opperman, Diederik J.

supporting information, p. 439 - 445 (2021/01/29)

Biocatalysts are receiving increased attention in the field of selective oxyfunctionalization of C-H bonds, with cytochrome P450 monooxygenases (CYP450s), and the related peroxygenases, leading the field. Here we report on the substrate promiscuity of CYP505A30, previously characterized as a fatty acid hydroxylase. In addition to its regioselective oxyfunctionalization of saturated fatty acids (ω-1-ω-3 hydroxylation), primary fatty alcohols are also accepted with similar regioselectivities. Moreover, alkanes such as n-octane and n-decane are also readily accepted, allowing for the production of non-vicinal diols through sequential oxygenation. This journal is

Facile Stereoselective Reduction of Prochiral Ketones by using an F420-dependent Alcohol Dehydrogenase

Martin, Caterina,Tjallinks, Gwen,Trajkovic, Milos,Fraaije, Marco W.

, p. 156 - 159 (2020/10/26)

Effective procedures for the synthesis of optically pure alcohols are highly valuable. A commonly employed method involves the biocatalytic reduction of prochiral ketones. This is typically achieved by using nicotinamide cofactor-dependent reductases. In this work, we demonstrate that a rather unexplored class of enzymes can also be used for this. We used an F420-dependent alcohol dehydrogenase (ADF) from Methanoculleus thermophilicus that was found to reduce various ketones to enantiopure alcohols. The respective (S) alcohols were obtained in excellent enantiopurity (>99 % ee). Furthermore, we discovered that the deazaflavoenzyme can be used as a self-sufficient system by merely using a sacrificial cosubstrate (isopropanol) and a catalytic amount of cofactor F420 or the unnatural cofactor FOP to achieve full conversion. This study reveals that deazaflavoenzymes complement the biocatalytic toolbox for enantioselective ketone reductions.

Application of new Ru (II) pyridine-based complexes in the partial oxidation of n-octane

Chanerika, Revana,Friedrich, Holger B.,Shozi, Mzamo L.

, (2019/12/24)

Tridentate and bidentate Ru (II) complexes were prepared through reaction of four pyridine-based ligands: pyCH2N(R)CH2py {R = propyl, tert-butyl, cyclohexyl and phenyl; py = pyridine} with the [(η6-C6H6)Ru(μ-Cl)Cl]2 dimer. Crystal structures of the new terdentate Ru (II) complexes [Ru{pyCH2N(R)CH2py}C6H6](PF6)2 (R = C3H7 (1), C (CH3)3 (2), C6H11 (3) and the bidentate Ru (II) complex [Ru{pyCH2N(R)}C6H6]PF6 (R = C6H5 (4)) are reported. It was found that complexes 1, 2, 3 and 4 crystallised as mono-metallic species, with a piano stool geometry around each Ru centre. All complexes were active in the selective oxidation of n-octane using t-BuOOH and H2O2 as oxidants. Complexes 2 and 4 reached a product yield of 12% with t-BuOOH as oxidant, however, superior yields (23–32%) were achieved using H2O2 over all systems. The selectivity was predominantly towards alcohols (particularly 2-octanol) over all complexes using t-BuOOH and H2O2 after reduction of the formed alkylhydroperoxides in solution by PPh3. High TONs of up to 2400 were achieved over the Ru/H2O2 systems.

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