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3391-86-4 Usage

Description

1-octen-3-ol, octenol (also known as mushroom alcohol) is a kind of secondary alcohol. It can emit special smell that can attract the biting insects such as mosquitoes. It is contained in the breath and sweat of mammals, and seems to be appreciated by insects such as mosquitoes. It is mainly produced by some plants and fungi including mushrooms and lemon balm through oxidative breakdown of linoleic acid. It can be used in combination with carbon dioxide to attract the insects to kill them. In addition, it can also be used as a food additive and used in certain perfumes. However, in animal study, it could disrupt dopamine homeostasis, and might be potentially involved in Parkinsonism.

Occurrence

Originally reported found in the mushroom Armillaria matsutake, a parasite growing on the radical hairs of Pinus densiflora in the forests of Japan; it has been isolated also in the essential oils of Mentha pulegium L., lavender and Mentha timjia. Also reported found in over 160 foods and beverages including banana, kumquat peel oil, berries, currants, guava, grapes, raisin, melon, pineapple, asparagus, potato, tomato, Mentha oils, thyme, wheat bread, cheeses, buttermilk, boiled egg, fish, cooked meats, hop oil, beer, cognac, rum, grape wines, cocoa, coffee, tea, pecans, plum, oats, soybean, olive, cloudberry, plums, beans, mushroom, marjoram, starfruit, sesame seed, fig, kelp, rice, beans, litchi, calamus, dill, licorice, pumpkin, buckwheat, sweet corn, corn tortilla, malt, rice, wort, krill, rosemary, Bourbon vanilla, mountain papaya, endive, lemon balm, shrimp, oyster, crab, clam, scallop, truffle, winter savory, anise hyssop and maté.

References

http://www.chm.bris.ac.uk/motm/octenol/octenolh.htm https://en.wikipedia.org/wiki/1-Octen-3-ol

Taste threshold values

Taste characteristics at 10 ppm: mushroom, earthy, fungal, green, oily, vegetative, umami sensation and savory-brothy.

Trade name

Matsutakeol (Takasago).

Preparation

From magnesium amyl bromide and acrolein.

Chemical Properties

1-Octen-3-ol may occur in the optically active form. It is found, for example, in lavender oil and is a steam-volatile component of mushrooms. l-Octen-3-ol is a liquid with an intense mushroom, forest–earthy odor that can be prepared by a Grignard reaction from vinylmagnesium bromide and hexanal. It is used in lavender compositions and in mushroom aromas.

Safety Profile

Poison by ingestion and intravenous routes. Moderately toxic by skin contact. When heated to decomposition it emits acrid smoke and irritating fumes.

Aroma threshold values

Detection: 14 ppb; recognition: 25 ppb

Description

l-Octen-3-ol has a powerful, sweet, earthy odor with a strong, herbaceous note reminiscent of lavender-lavandin, rose, and hay. It has a sweet, herbaceous taste. May be prepared from magnesium amyl bromide and acrolein.

Chemical Properties

1-Octen-3-Ol is a colorless to yellow liquid with a mushroom, green, vegetable, and fatty odor. It is used in edible flavor blends such as mushroom, tomato, potato, milk, and nut.It is a secondary alcohol derived from 1-octene. It is an unsaturated alcohol that exists as two enantiomers, the (R)-(–)-form and the (S)-(+)-form. It is found most often as the racemic mixture. Common Applications cheese lavender potato savoury asparagus carrot cucumber mushroom Natural occurrence: Clover, cooked artichoke, fish, mushroom, peas, soybeans, wheat bread, tea, and beef.

Chemical Properties

1-Octen-3-ol has a powerful, sweet, earthy odor with a strong, herbaceous note reminiscent of lavender–lavandin, rose and hay. It has a sweet, herbaceous taste.

Uses

1-Octen-3-ol is a chemical that attracts biting insects such as mosquitoes. It occurs naturally in some plants, fungi, and molds; and it is a metabolite of linoleic acid. It is also found in human breath and sweat, which is unfortunate because it attracts mosquitoes and other biting insects and it was once believed that insect repellent DEET works by blocking the insects' octenol odorant receptors. Used as a flavoring agent in cheese and chocolate. Used as a perfuming agent in cosmetic industry. Since the discovery in the early 1980s that 1-octen-3-ol, isolated from oxen breath, attracts tsetse fly, there has been growing interest in exploring the use of this semiochemical as a possible generic lure for trapping host-seeking mosquitoes. Intriguingly, traps baited with 1-octen-3-ol captured significantly more females of the malaria mosquito, Anopheles gambiae, and the yellow fever mosquito, Aedes aegypti, than control traps, but failed to attract the southern house mosquito, Culex quinquefasciatus.

Definition

ChEBI: An alkenyl alcohol with a structure based on a C8 unbranched chain with the hydroxy group at C-2 and unsaturation at C-11C-2.
InChI:InChI=1/C8H16O/c1-3-5-6-7-8(9)4-2/h4,8-9H,2-3,5-7H2,1H3/t8-/m0/s1

3391-86-4 Well-known Company Product Price

Brand (Code)Product description CAS number Packaging Price Detail
Alfa Aesar (A12079)  1-Octen-3-ol, 98%    3391-86-4 10g 294.0CNY Detail
Alfa Aesar (A12079)  1-Octen-3-ol, 98%    3391-86-4 50g 984.0CNY Detail
Alfa Aesar (A12079)  1-Octen-3-ol, 98%    3391-86-4 250g 4183.0CNY Detail
Sigma-Aldrich (68225)  1-Octen-3-ol  analytical standard 3391-86-4 68225-5ML 521.82CNY Detail

3391-86-4SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name oct-1-en-3-ol

1.2 Other means of identification

Product number -
Other names Pentyl vinyl carbinol

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:3391-86-4 SDS

3391-86-4Synthetic route

E-2,3-epoxy-1-octanyl tosylate
160080-95-5

E-2,3-epoxy-1-octanyl tosylate

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

1-octen-3-ol

Conditions
ConditionsYield
With aluminum oxide; tellurium(2-) for 2.5h;100%
With sodium hydroxide; tellurium; rongalite In tetrahydrofuran; water at 50℃; for 2h;80%
With tellurium(2-) for 0.233333h; Product distribution; other reaction conditions, other reaction time, reagent, solvent;
Multi-step reaction with 2 steps
1: 97 percent / NaI / acetone / 3 h
2: 74 percent / Bu3SnAlEt2 / tetrahydrofuran / 1 h / 0 °C
View Scheme
3-(2-Methoxy-ethoxymethoxy)-oct-1-ene
88738-33-4

3-(2-Methoxy-ethoxymethoxy)-oct-1-ene

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

1-octen-3-ol

Conditions
ConditionsYield
With pyridinium p-toluenesulfonate In tert-butyl alcohol for 3h; Heating;99%
1-Octyn-3-ol
818-72-4

1-Octyn-3-ol

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

1-octen-3-ol

Conditions
ConditionsYield
With isocyanate de chlorosulfonyle; hydrogen; palladium diacetate; borohydride exchange resin In ethanol for 0.5h;97%
With C16H26CuO In 2-methyl-propan-1-ol; toluene at 25℃; for 1h;92%
With 2-methyl-propan-1-ol; [1,3-bis(2,6-di-iso-propylphenyl)imidazol-2-ylidene]copper(I) tert-butoxide In toluene at 25℃; for 1h; Inert atmosphere; Glovebox; chemoselective reaction;92%
(E)-3-<(2-tetrahydropyranyl)oxy>-1-iodo-1-octene
50999-80-9

(E)-3-<(2-tetrahydropyranyl)oxy>-1-iodo-1-octene

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

1-octen-3-ol

Conditions
ConditionsYield
With trichloroisocyanuric acid In methanol at 20℃; for 5h;95%
With water; lithium chloride In dimethyl sulfoxide at 90℃; for 6h; Hydrolysis;80%
With magnesium bromide In diethyl ether for 2h; Ambient temperature;72%
1-Octene, 3-(methoxymethoxy)-
88738-34-5

1-Octene, 3-(methoxymethoxy)-

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

1-octen-3-ol

Conditions
ConditionsYield
With pyridinium p-toluenesulfonate In tert-butyl alcohol for 3.5h; Heating;95%
oct-1-en-3-one
4312-99-6

oct-1-en-3-one

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

1-octen-3-ol

Conditions
ConditionsYield
With sodium tetrahydroborate In methanol at 20℃; for 4h;93%
With isoindoline; lithium aluminium tetrahydride In diethyl ether at -15℃; for 1.5h;
N,N-Diethyl-O-(1-vinyl-hexyl)-hydroxylamine
73827-90-4

N,N-Diethyl-O-(1-vinyl-hexyl)-hydroxylamine

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

1-octen-3-ol

Conditions
ConditionsYield
With zinc In acetic acid Ambient temperature;93%
vinyl magnesium bromide
1826-67-1

vinyl magnesium bromide

hexanal
66-25-1

hexanal

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

1-octen-3-ol

Conditions
ConditionsYield
In tetrahydrofuran at 0℃;92%
In tetrahydrofuran for 4h; Heating;75%
In tetrahydrofuran at -15 - 20℃;74%
1-Bromopentane
110-53-2

1-Bromopentane

acrolein
107-02-8

acrolein

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

1-octen-3-ol

Conditions
ConditionsYield
Stage #1: 1-Bromopentane With magnesium In tert-butyl methyl ether for 1h; Reflux;
Stage #2: acrolein In tert-butyl methyl ether at -5 - 2℃; for 1h;
92%
Stage #1: 1-Bromopentane With iodine; magnesium In diethyl ether at 0℃; Inert atmosphere;
Stage #2: acrolein In diethyl ether for 1.5h; Inert atmosphere;
85%
Stage #1: 1-Bromopentane With iodine; magnesium In diethyl ether Inert atmosphere;
Stage #2: acrolein In diethyl ether at 0℃;
85%
3-Nitrooxy-oct-1-ene
100009-47-0

3-Nitrooxy-oct-1-ene

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

1-octen-3-ol

Conditions
ConditionsYield
With acetic acid; zinc83%
2,3-epoxyoctanol
101758-85-4

2,3-epoxyoctanol

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

1-octen-3-ol

Conditions
ConditionsYield
With diethyltitanium dichloride; zinc(II) chloride; zinc In tetrahydrofuran82%
With diethyltitanium dichloride; zinc(II) chloride; zinc In tetrahydrofuran Product distribution; Mechanism; other 2,3-epoxy alcohols;82%
Multi-step reaction with 3 steps
1: 91 percent / powdered KOH / diethyl ether / -10 deg C, then 0 deg C, 30 min
2: 97 percent / NaI / acetone / 3 h
3: 74 percent / Bu3SnAlEt2 / tetrahydrofuran / 1 h / 0 °C
View Scheme
Conditions
ConditionsYield
With zinc In methanol for 3h; Heating;80%
With Bu3SnAlEt2 In tetrahydrofuran at 0℃; for 1h;74%
vinylmagnesium chloride
3536-96-7

vinylmagnesium chloride

hexanal
66-25-1

hexanal

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

1-octen-3-ol

Conditions
ConditionsYield
In tetrahydrofuran; diethyl ether at -15℃; for 1.5h; Inert atmosphere;79%
In tetrahydrofuran at 23℃; for 1h; Inert atmosphere; Cooling;
In tetrahydrofuran at 0 - 20℃;
Ethyl hexanoate
123-66-0

Ethyl hexanoate

vinyl magnesium bromide
1826-67-1

vinyl magnesium bromide

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

1-octen-3-ol

Conditions
ConditionsYield
Stage #1: Ethyl hexanoate With lithium diisobutyl-tert-butoxyaluminum hydride In tetrahydrofuran; hexane at 0℃;
Stage #2: vinyl magnesium bromide In tetrahydrofuran; diethyl ether; hexane at 20℃;
Stage #3: With hydrogenchloride; water In tetrahydrofuran; diethyl ether; hexane
78%
2-bromomethyl-3-pentyl-oxirane

2-bromomethyl-3-pentyl-oxirane

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

1-octen-3-ol

Conditions
ConditionsYield
With indium(III) chloride; sodium tetrahydroborate In acetonitrile at 20℃; for 7h;77%
epoxybutene
930-22-3

epoxybutene

n-butyllithium
109-72-8, 29786-93-4

n-butyllithium

A

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

1-octen-3-ol

B

2-butyl-but-3-en-1-ol
53045-66-2

2-butyl-but-3-en-1-ol

Conditions
ConditionsYield
With boron trifluoride diethyl etherate In diethyl ether at -105℃; for 0.5h; Ring cleavage;A 16%
B 75%
C21H28OSi

C21H28OSi

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

1-octen-3-ol

Conditions
ConditionsYield
With 18-crown-6 ether In ethanol; water at 45℃; for 22h; Reagent/catalyst; Solvent; Temperature; Green chemistry;75%
C14H30OSi

C14H30OSi

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

1-octen-3-ol

Conditions
ConditionsYield
With benzo[1,3,2]dioxaborole; Wilkinson's catalyst In tetrahydrofuran at 20℃; for 15h;65%
2-octenol
22104-78-5

2-octenol

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

1-octen-3-ol

Conditions
ConditionsYield
With silica-supported monomeric vanadium-oxo species In acetonitrile at 60℃; for 8h; Inert atmosphere;60%
1-methoxy-4-[(oct-1-en-3-yloxy)methyl]benzene

1-methoxy-4-[(oct-1-en-3-yloxy)methyl]benzene

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

1-octen-3-ol

Conditions
ConditionsYield
With water; sodium hydrogencarbonate; bis-[(trifluoroacetoxy)iodo]benzene; meso-2,5-bis(methoxycarbonyl)-2,5-dimethylpyrrolidine-1-oxyl In dichloromethane at 20℃; for 2h; chemoselective reaction;55%
oct-1-ene
111-66-0

oct-1-ene

A

octanol
111-87-5

octanol

B

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

1-octen-3-ol

D

2-octenol
22104-78-5

2-octenol

Conditions
ConditionsYield
With water; oxygen In ethanol at 75℃; for 24h; pH=3.7;A n/a
B 44%
C 31%
D n/a
With water; oxygen In ethanol at 75℃; for 24h; pH=6.1;A n/a
B 32.5%
C 14.9%
D n/a
1-phenylsulfinyl-octan-2-ol
76989-79-2

1-phenylsulfinyl-octan-2-ol

A

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

1-octen-3-ol

B

cyclohexanone
108-94-1

cyclohexanone

Conditions
ConditionsYield
With potassium tert-butylate; tert-butyl alcohol for 336h; Ambient temperature;A 40%
B 10%
ethanol
64-17-5

ethanol

oct-1-ene
111-66-0

oct-1-ene

A

octanol
111-87-5

octanol

B

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

1-octen-3-ol

D

n-octyl acetate
112-14-1

n-octyl acetate

E

2-octenol
22104-78-5

2-octenol

Conditions
ConditionsYield
With water; oxygen at 75℃; for 24h; pH=6.1;A n/a
B 31.7%
C 20.8%
D 6.8%
E n/a
oct-1-ene
111-66-0

oct-1-ene

acetonitrile
75-05-8

acetonitrile

A

heptanal
111-71-7

heptanal

B

octanol
111-87-5

octanol

C

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

1-octen-3-ol

E

n-octyl acetate
112-14-1

n-octyl acetate

F

1,2-Epoxyoctane
2984-50-1

1,2-Epoxyoctane

G

2-octenol
22104-78-5

2-octenol

Conditions
ConditionsYield
With water; oxygen at 75℃; for 24h;A 5.5%
B n/a
C 24.8%
D 31.4%
E 5.6%
F 7.4%
G n/a
oct-1-ene
111-66-0

oct-1-ene

A

heptanal
111-71-7

heptanal

B

octanol
111-87-5

octanol

C

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

1-octen-3-ol

E

1,2-Epoxyoctane
2984-50-1

1,2-Epoxyoctane

F

2-octenol
22104-78-5

2-octenol

Conditions
ConditionsYield
With water; oxygen In acetonitrile at 75℃; for 24h;A 5.1%
B n/a
C 29.2%
D 27.7%
E 9.1%
F n/a
oct-1-ene
111-66-0

oct-1-ene

A

octanol
111-87-5

octanol

B

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

1-octen-3-ol

D

1,2-Epoxyoctane
2984-50-1

1,2-Epoxyoctane

E

2-octenol
22104-78-5

2-octenol

Conditions
ConditionsYield
With water; oxygen In acetonitrile at 75℃; for 24h;A n/a
B 26.2%
C 26.2%
D 6.9%
E n/a
oct-1-ene
111-66-0

oct-1-ene

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

1-octen-3-ol

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); carbon dioxide; 2,5-di-tert-butyl-p-benzoquinone; water In 1,4-dioxane at 40℃; under 30003 Torr; for 72h; Inert atmosphere; Autoclave;18%
Multi-step reaction with 2 steps
1.1: (MesPDI)CoMe / neat (no solvent) / 1 h / 23 °C
2.1: 3-chloro-benzenecarboperoxoic acid; disodium hydrogenphosphate / dichloromethane / 1 h / Cooling with ice
2.2: 16 h / 20 °C
View Scheme
oct-1-ene
111-66-0

oct-1-ene

A

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

1-octen-3-ol

B

1,2-Epoxyoctane
2984-50-1

1,2-Epoxyoctane

Conditions
ConditionsYield
With meso-tetraphenylporphyrin iron(III) chloride; iodosylbenzene In dichloromethane for 0.5h; Ambient temperature; Yield given;A 1%
B n/a
With dihydrogen peroxide In acetonitrile for 0.583333h; Ultrasonic irradiation; Reflux;
With dihydrogen peroxide In acetonitrile at 60℃; for 0.666667h; Ultrasonic irradiation;
chloromethyl-(1-pentyl-allyl)-ether
99064-28-5

chloromethyl-(1-pentyl-allyl)-ether

A

formaldehyde-[bis-(1-pentyl-allyl)-acetal]
101592-01-2

formaldehyde-[bis-(1-pentyl-allyl)-acetal]

B

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

1-octen-3-ol

Conditions
ConditionsYield
With water
With sodium hydrogencarbonate
oct-1-ene
111-66-0

oct-1-ene

A

oct-1-en-3-one
4312-99-6

oct-1-en-3-one

B

(E)-2-Octenal
2548-87-0

(E)-2-Octenal

C

(E)-oct-2-en-1-ol
18409-17-1

(E)-oct-2-en-1-ol

D

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

1-octen-3-ol

E

1,2-Epoxyoctane
2984-50-1

1,2-Epoxyoctane

Conditions
ConditionsYield
With oxygen; bis(acetylacetonato)dioxidomolybdenum(VI); cobalt(III) acetylacetonate In 1,2-dichloro-benzene at 110℃; for 5.3h; Product distribution; other temperatures, catalysts, times, olefins;A n/a
B n/a
C n/a
D n/a
E 61 % Chromat.
1-octen-3-ol
3391-86-4

1-octen-3-ol

oct-1-en-3-one
4312-99-6

oct-1-en-3-one

Conditions
ConditionsYield
With cis-dichlorotetrakis(diemethylsulfoxide) ruthenium(II); sodium formate In water; toluene at 80℃; for 1h; Inert atmosphere;100%
With 2,2,6,6-tetramethyl-piperidine-N-oxyl; periodic acid In dichloromethane at 20℃; for 0.583333h;98%
With chromium (VI) oxide In toluene for 0.333333h; microwave irradiation;98%
1-octen-3-ol
3391-86-4

1-octen-3-ol

3-octanone
106-68-3

3-octanone

Conditions
ConditionsYield
With glass encapsulated Rh-onium ion catalyst In toluene for 1.83333h; Heating;100%
With potassium tert-butylate; trimethyl-4,6,9 hexaza-1,3,4,6,7,9 phospha-5 tricyclo<3.3.1.13,7>decane; dichloro(benzene)ruthenium(II) dimer In tetrahydrofuran at 75℃; for 0.25h; Kinetics; Product distribution; Further Variations:; Catalysts; Solvents;100%
With C34H49ClFePRhS; hydrogen; sodium methylate In tetrahydrofuran at 82℃; under 22502.3 Torr; for 16h; Autoclave; Inert atmosphere;100%
1-octen-3-ol
3391-86-4

1-octen-3-ol

1,2-epoxy-3-octanol
159954-53-7

1,2-epoxy-3-octanol

Conditions
ConditionsYield
With tert.-butylhydroperoxide In acetonitrile at 80℃; for 24h; Catalytic behavior; Reagent/catalyst;100%
With tert.-butylhydroperoxide In chloroform for 4h; Catalytic behavior; Reflux;99%
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 0 - 20℃; for 18h;95%
1,1-dimethoxyethylene
922-69-0

1,1-dimethoxyethylene

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

1-octen-3-ol

C12H24O3
1188286-39-6

C12H24O3

Conditions
ConditionsYield
at 20℃; Inert atmosphere; neat (no solvent);100%
1-octen-3-ol
3391-86-4

1-octen-3-ol

Triethyl orthoacetate
78-39-7

Triethyl orthoacetate

ethyl trans-4-decenoate
76649-16-6

ethyl trans-4-decenoate

Conditions
ConditionsYield
With propionic acid at 150℃; for 3h; Temperature; Claisen Rearrangement;99.9%
Trimethyl orthoacetate
1445-45-0

Trimethyl orthoacetate

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

1-octen-3-ol

methyl (4E)-dec-4-enoate
93979-14-7

methyl (4E)-dec-4-enoate

Conditions
ConditionsYield
With propionic acid at 125℃; for 2h; Temperature; Claisen Rearrangement;99.5%
With propionic acid at 105℃; for 4.5h;87%
With propionic acid at 100 - 105℃;
1-octen-3-ol
3391-86-4

1-octen-3-ol

acetic anhydride
108-24-7

acetic anhydride

oct-1-en-3-yl acetate
2442-10-6

oct-1-en-3-yl acetate

Conditions
ConditionsYield
With C12H8N2*2CH4O3S at 50℃; for 3h;99%
With dmap In dichloromethane at 20℃; for 1.5h;94%
aluminium dodecatungsten phosphate at 20℃; for 0.0833333h;93%
Isopropenyl acetate
108-22-5

Isopropenyl acetate

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

1-octen-3-ol

oct-1-en-3-yl acetate
2442-10-6

oct-1-en-3-yl acetate

Conditions
ConditionsYield
With Cp*2Sm(THF)2; cyclohexanone oxime acetate In toluene for 0.1h; Ambient temperature;99%
With iron(III) trifluoromethanesulfonate at 20℃; for 5h; Schlenk technique;92%
1-octen-3-ol
3391-86-4

1-octen-3-ol

tris-(trimethylsilyl)silane
1873-77-4

tris-(trimethylsilyl)silane

6-[tris(trimethylsilyl)]-3-octanol
1001067-37-3

6-[tris(trimethylsilyl)]-3-octanol

Conditions
ConditionsYield
With 1,1'-azobis(1-cyanocyclohexanenitrile) In water at 100℃; for 4h;99%
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%
1-octen-3-ol
3391-86-4

1-octen-3-ol

propionic acid
802294-64-0

propionic acid

Triethyl orthoacetate
78-39-7

Triethyl orthoacetate

ethyl trans-4-decenoate
76649-16-6

ethyl trans-4-decenoate

Conditions
ConditionsYield
120 deg C, then 160 deg C, 2 h;98%
1-octen-3-ol
3391-86-4

1-octen-3-ol

1,2-dibromomethane
74-95-3

1,2-dibromomethane

1-cyclopropyl-1-hexanol
65364-55-8

1-cyclopropyl-1-hexanol

Conditions
ConditionsYield
With n-butyllithium; tert-butylmagnesium chloride In diethyl ether; hexane98%
Stage #1: 1-octen-3-ol With n-butyllithium In tetrahydrofuran; hexane Inert atmosphere;
Stage #2: 1,2-dibromomethane With tert-butylmagnesium chloride In tetrahydrofuran; hexane Inert atmosphere;
98%
1-octen-3-ol
3391-86-4

1-octen-3-ol

phenylboronic acid
98-80-6

phenylboronic acid

1-phenyloctan-3-one
6047-99-0

1-phenyloctan-3-one

Conditions
ConditionsYield
With 2.9-dimethyl-1,10-phenanthroline; palladium diacetate; silver carbonate In acetonitrile at 60℃; for 24h; regioselective reaction;98%
With 2.9-dimethyl-1,10-phenanthroline; palladium diacetate; copper(l) chloride In dimethyl sulfoxide at 50℃; under 760.051 Torr; for 12h;98%
With oxygen; palladium diacetate; acetic acid; copper(l) chloride In dimethyl sulfoxide at 50℃; under 760.051 Torr; for 20h; regioselective reaction;94%
Thiomorpholin
123-90-0

Thiomorpholin

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

1-octen-3-ol

2-thiomorpholinooctan-3-one

2-thiomorpholinooctan-3-one

Conditions
ConditionsYield
Stage #1: 1-octen-3-ol With [Ir(III)(η5-pentamethylcyclopentadienyl)(H2O)3](SO4); iodine; oxygen; sodium nitrite In 2-methyltetrahydrofuran; water under 760.051 Torr; for 24h; Sealed tube;
Stage #2: Thiomorpholin In 2-methyltetrahydrofuran; water for 16h;
98%
1-octen-3-ol
3391-86-4

1-octen-3-ol

tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

tert-butyl-dimethyl-(1-vinyl-hexyloxy)-silane
107220-03-1

tert-butyl-dimethyl-(1-vinyl-hexyloxy)-silane

Conditions
ConditionsYield
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 68h;97%
1-octen-3-ol
3391-86-4

1-octen-3-ol

benzoyl chloride
98-88-4

benzoyl chloride

3-(1-octen)-yl benzoate
52513-06-1

3-(1-octen)-yl benzoate

Conditions
ConditionsYield
With pyridine In dichloromethane at 25℃; for 0.5h;95%
With zinc In benzene at 20℃; for 1h;53%
With pyridine In dichloromethane at 0 - 20℃;
1-octen-3-ol
3391-86-4

1-octen-3-ol

1-iodohept-2-ene
790713-58-5

1-iodohept-2-ene

Conditions
ConditionsYield
With zirconium(IV) chloride; sodium iodide In acetonitrile for 0.0833333h; Heating;95%
dichloroacethyl chloride
79-36-7

dichloroacethyl chloride

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

1-octen-3-ol

1-pentyl-2-propenyl dichloroacetate
937036-44-7

1-pentyl-2-propenyl dichloroacetate

Conditions
ConditionsYield
With dmap In dichloromethane at 20℃; for 2h;95%
1-octen-3-ol
3391-86-4

1-octen-3-ol

acetyl chloride
75-36-5

acetyl chloride

oct-1-en-3-yl acetate
2442-10-6

oct-1-en-3-yl acetate

Conditions
ConditionsYield
With dmap In dichloromethane95%
Stage #1: 1-octen-3-ol With pyridine In dichloromethane at 0℃; Inert atmosphere;
Stage #2: acetyl chloride In dichloromethane at 0 - 20℃; Inert atmosphere;
1-octen-3-ol
3391-86-4

1-octen-3-ol

ethyl chloromethyl ether
3188-13-4

ethyl chloromethyl ether

3-(ethoxymethoxy)oct-1-ene
1150097-94-1

3-(ethoxymethoxy)oct-1-ene

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In dichloromethane for 12h; Inert atmosphere; Reflux;95%
With N-ethyl-N,N-diisopropylamine In dichloromethane for 12h; Inert atmosphere; Reflux;95%
1-octen-3-ol
3391-86-4

1-octen-3-ol

4-iodophenylboronic acid
5122-99-6

4-iodophenylboronic acid

1-(4-iodophenyl)octan-3-one
1607844-59-6

1-(4-iodophenyl)octan-3-one

Conditions
ConditionsYield
With 2.9-dimethyl-1,10-phenanthroline; palladium diacetate; copper(l) chloride In dimethyl sulfoxide at 50℃; under 760.051 Torr; for 12h;95%
1-octen-3-ol
3391-86-4

1-octen-3-ol

aniline
62-53-3

aniline

N-(oct-1-en-3-yl)aniline

N-(oct-1-en-3-yl)aniline

Conditions
ConditionsYield
With [O,O’-((S)-1,1´-dinaphthyl-2,2´-diyl)-N,N´-di-(S,S)-1-(2-methoxyphenyl)ethylphosphoramidite]; (S)-1,1'-binaphthyl-2,2'-diyl hydrogen phosphate; bis(dibenzylideneacetone)-palladium(0) In tetrahydrofuran at 25℃; for 12h; Inert atmosphere; Schlenk technique; enantioselective reaction;95%
1-octen-3-ol
3391-86-4

1-octen-3-ol

(CH3)2NCOX

(CH3)2NCOX

Dimethyl-carbamic acid 1-vinyl-hexyl ester
90498-66-1

Dimethyl-carbamic acid 1-vinyl-hexyl ester

Conditions
ConditionsYield
94%
1-octen-3-ol
3391-86-4

1-octen-3-ol

5-hepten-1-al
62238-34-0

5-hepten-1-al

(E)-8-Hydroxy-7-methyl-tetradec-11-en-6-one

(E)-8-Hydroxy-7-methyl-tetradec-11-en-6-one

Conditions
ConditionsYield
With magnesium bromide; (dppe)NiHCl In tetrahydrofuran at -50 - 20℃; for 1h;94%
1-octen-3-ol
3391-86-4

1-octen-3-ol

phenylboronic acid
98-80-6

phenylboronic acid

1-phenyl-1-octen-3-one
5635-72-3

1-phenyl-1-octen-3-one

Conditions
ConditionsYield
Stage #1: 1-octen-3-ol With oxygen; palladium diacetate In N,N-dimethyl-formamide at 90℃; under 760.051 Torr; for 4h; Green chemistry;
Stage #2: phenylboronic acid With 2.9-dimethyl-1,10-phenanthroline In N,N-dimethyl-formamide at 90℃; for 18h; Heck Reaction; Green chemistry;
94%
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