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13019-22-2

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13019-22-2 Usage

Chemical Properties

Different sources of media describe the Chemical Properties of 13019-22-2 differently. You can refer to the following data:
1. colourless liquid
2. 9-Decen-1 (cipher)-ol has been identified as a trace constituent of cognac. It is a colorless liquid with a fresh, dewy, rose note that can be prepared by partial dehydration of 1,10-decanediol. It is used in rosy, floral soap perfumes.

Occurrence

Apparently has not been reported to occur in nature.

Uses

Different sources of media describe the Uses of 13019-22-2 differently. You can refer to the following data:
1. It finds it uses in a wide range of fragrances, especially in fine fragrances and soaps, in floral, rose petal or herbal fragrances. 9-Decen-1-ol is used in the preparation of semifluorinated acids required for the synthesis of poly(styrene-b-semi fluorinated isoprene) block copolymers with -CF2H-terminated side groups.
2. 9-Decen-1-ol was used in the preparation of semifluorinated acids required for the synthesis of poly(styrene-b-semifluorinated isoprene) block copolymers with -CF2H-terminated side groups.

Preparation

From 1,10-decamethylene glycol (Arctander, 1969).

General Description

9-Decen-1-ol undergoes oxidation to give 9-decenoic in aqueous media (dioxane–water mixtures) in the presence of supported palladium or platinum catalysts.

Trade name

Rosalva (IFF), Trepanol? (Takasago).

Check Digit Verification of cas no

The CAS Registry Mumber 13019-22-2 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,3,0,1 and 9 respectively; the second part has 2 digits, 2 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 13019-22:
(7*1)+(6*3)+(5*0)+(4*1)+(3*9)+(2*2)+(1*2)=62
62 % 10 = 2
So 13019-22-2 is a valid CAS Registry Number.
InChI:InChI=1/C10H20O/c1-2-3-4-5-6-7-8-9-10-11/h2,11H,1,3-10H2

13019-22-2 Well-known Company Product Price

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  • Alfa Aesar

  • (A19490)  9-Decen-1-ol, 90+%   

  • 13019-22-2

  • 5g

  • 210.0CNY

  • Detail
  • Alfa Aesar

  • (A19490)  9-Decen-1-ol, 90+%   

  • 13019-22-2

  • 25g

  • 571.0CNY

  • Detail
  • Alfa Aesar

  • (A19490)  9-Decen-1-ol, 90+%   

  • 13019-22-2

  • 100g

  • 1781.0CNY

  • Detail

13019-22-2SDS

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 dec-9-en-1-ol

1.2 Other means of identification

Product number -
Other names Decylenic alcohol

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:13019-22-2 SDS

13019-22-2Synthetic route

methyl 9-decenoate
25601-41-6

methyl 9-decenoate

9-Decen-1-ol
13019-22-2

9-Decen-1-ol

Conditions
ConditionsYield
Stage #1: methyl 9-decenoate With lithium aluminium tetrahydride In tetrahydrofuran at 20℃; for 5.5h; Cooling;
Stage #2: With sodium hydroxide In tetrahydrofuran; water at 20℃; Reagent/catalyst; Concentration; Solvent; Temperature; Time;
98.3%
With lithium aluminium tetrahydride In tetrahydrofuran at 15 - 20℃; for 5.5h; Inert atmosphere;98.3%
With sodium bis(2-methoxyethoxy)aluminium dihydride In toluene at 15 - 20℃; for 2h; Sealed tube; Cooling with ice; Inert atmosphere;97.14%
1-(tetrahydro-2-pyranyloxy)-9-decene
67136-13-4

1-(tetrahydro-2-pyranyloxy)-9-decene

9-Decen-1-ol
13019-22-2

9-Decen-1-ol

Conditions
ConditionsYield
With copper dichloride In methanol at 20℃; Hydrolysis;95%
With CuCl2*2H2O In methanol at 20℃; for 1.25h;95%
decane-1,2,10-triol
91717-85-0

decane-1,2,10-triol

9-Decen-1-ol
13019-22-2

9-Decen-1-ol

Conditions
ConditionsYield
With rhenium(VII) oxide; triphenylphosphine at 165℃; for 1h;90%
1,10-Decanediol
112-47-0

1,10-Decanediol

9-Decen-1-ol
13019-22-2

9-Decen-1-ol

Conditions
ConditionsYield
With 1-hexadecylcarboxylic acid at 340℃; for 5h; Temperature; Reagent/catalyst; Molecular sieve;88%
With 1-hexadecylcarboxylic acid; stearic acid at 330 - 350℃; under 700 Torr; for 150h;80%
1,10-Decanediol
112-47-0

1,10-Decanediol

A

1,10-decadiene
1647-16-1

1,10-decadiene

B

9-Decen-1-ol
13019-22-2

9-Decen-1-ol

Conditions
ConditionsYield
With 1-hexadecylcarboxylic acid at 340℃; for 6h; Molecular sieve;A n/a
B 88%
9-decenal
39770-05-3

9-decenal

9-Decen-1-ol
13019-22-2

9-Decen-1-ol

Conditions
ConditionsYield
With manganese; water; 2,4,6-collidine hydrochloride In tetrahydrofuran at 20℃; chemoselective reaction;84%
trans-9-decenoic acid ethyl ester
67233-91-4

trans-9-decenoic acid ethyl ester

9-Decen-1-ol
13019-22-2

9-Decen-1-ol

Conditions
ConditionsYield
With styrene; [RuCl2(N,N'-(ethane-1,2-diyl)bis(1-(2-(diphenylphosphaneyl)phenyl)methanimine))]; potassium methanolate; hydrogen at 80℃; under 37503.8 Torr; for 5h; Time; Inert atmosphere; Autoclave; chemoselective reaction;84%
With styrene; [RuCl2(N,N'-(ethane-1,2-diyl)bis(1-(2-(diphenylphosphaneyl)phenyl)methanimine))]; potassium methanolate; hydrogen at 80℃; under 37503.8 Torr; for 5h; Inert atmosphere; Autoclave;84%
dec-9-enoic acid
14436-32-9

dec-9-enoic acid

9-Decen-1-ol
13019-22-2

9-Decen-1-ol

Conditions
ConditionsYield
With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; for 1h; Inert atmosphere;80%
With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃;64%
With nonan-1-al; samarium diiodide; samarium(III) trifluoromethanesulfonate In tetrahydrofuran; methanol; potassium hydroxide at 20℃; for 0.0833333h; Reduction;96 % Chromat.
1-((dec-9-en-1-yloxy)methyl)-4-methoxybenzene

1-((dec-9-en-1-yloxy)methyl)-4-methoxybenzene

9-Decen-1-ol
13019-22-2

9-Decen-1-ol

Conditions
ConditionsYield
With ammonium peroxydisulfate; 9-(2-mesityl)-10-methylacridinium perchlorate In dichloromethane; water at 20 - 30℃; for 2h; Irradiation; Green chemistry;80%
Stage #1: 1-((dec-9-en-1-yloxy)methyl)-4-methoxybenzene 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;
79%
((dec-9-en-1-yloxy)methyl)benzene
100189-71-7

((dec-9-en-1-yloxy)methyl)benzene

A

9-Decen-1-ol
13019-22-2

9-Decen-1-ol

B

9-bromo-decane-1-ol
1275582-65-4

9-bromo-decane-1-ol

Conditions
ConditionsYield
With triphenylphosphine hydrobromide In acetonitrile for 12h; Reflux;A 63%
B 8%
((dec-9-en-1-yloxy)methyl)benzene
100189-71-7

((dec-9-en-1-yloxy)methyl)benzene

9-Decen-1-ol
13019-22-2

9-Decen-1-ol

Conditions
ConditionsYield
With barium carbonate; 2,3-dicyano-5,6-dichloro-p-benzoquinone In acetonitrile at 20℃; for 16h; Irradiation;52%
11-hydroxyundecanoic acid
3669-80-5

11-hydroxyundecanoic acid

A

1-Decanol
112-30-1

1-Decanol

B

9-Decen-1-ol
13019-22-2

9-Decen-1-ol

C

1,20-eicosanediol
7735-43-5

1,20-eicosanediol

Conditions
ConditionsYield
With potassium methanolate In methanol at 40℃; electrolysis: anode: platinum foil; current source: galvanostat; current density 200 mA cm-2; current consumption: 3.03 F mol-1; cell voltage 50-60 V; Yield given;A n/a
B n/a
C 42%
With potassium methanolate In methanol at 40℃; electrolysis: anode: platinum foil; current source: galvanostat; current density 200 mA cm-2; current consumption: 3.03 F mol-1; cell voltage 50-60 V; Yields of byproduct given;A n/a
B n/a
C 42%
1-bromo-10-decanol
53463-68-6

1-bromo-10-decanol

9-Decen-1-ol
13019-22-2

9-Decen-1-ol

Conditions
ConditionsYield
With potassium tert-butylate In tetrahydrofuran; toluene at 0℃; for 0.5h;20%
2,13-dioxa-tetradecanedioic acid diethyl ester
96536-94-6

2,13-dioxa-tetradecanedioic acid diethyl ester

A

1,10-decadiene
1647-16-1

1,10-decadiene

B

1,10-Decanediol
112-47-0

1,10-Decanediol

C

9-Decen-1-ol
13019-22-2

9-Decen-1-ol

D

carbonic acid ethyl ester-(10-hydroxy-decyl ester)
100528-96-9

carbonic acid ethyl ester-(10-hydroxy-decyl ester)

Conditions
ConditionsYield
at 500℃; Produkt 5-7:Aethanol,Kohlensaeure-aethylester-dec-9-enylester,Aethylen.Pyrolysis;
2,13-dioxa-tetradecanedioic acid diethyl ester
96536-94-6

2,13-dioxa-tetradecanedioic acid diethyl ester

9-Decen-1-ol
13019-22-2

9-Decen-1-ol

Conditions
ConditionsYield
at 500℃;
10-hydroxy-2-decanone
35295-48-8

10-hydroxy-2-decanone

9-Decen-1-ol
13019-22-2

9-Decen-1-ol

Conditions
ConditionsYield
aluminum oxide Heating;
9-decen-1-yl acetate
50816-18-7

9-decen-1-yl acetate

9-Decen-1-ol
13019-22-2

9-Decen-1-ol

Conditions
ConditionsYield
With sodium hydroxide In methanol
C12H25LiO2

C12H25LiO2

acetylene
74-86-2

acetylene

9-Decen-1-ol
13019-22-2

9-Decen-1-ol

Conditions
ConditionsYield
With copper(I) bromide dimethylsulfide complex; lithium bromide 1.) Et2O; 2.) -50 deg C, then 30 min, -30 deg C; Yield given. Multistep reaction;
dec-9-en-1-yl benzoate

dec-9-en-1-yl benzoate

A

9-Decen-1-ol
13019-22-2

9-Decen-1-ol

B

n-decyl benzoate
36685-97-9

n-decyl benzoate

Conditions
ConditionsYield
With hydrogenchloride; Schwartz's reagent Yield given; Multistep reaction. Yields of byproduct given;
polymer(ic) decamethylene carbonate

polymer(ic) decamethylene carbonate

9-Decen-1-ol
13019-22-2

9-Decen-1-ol

Conditions
ConditionsYield
at 290℃;
10-chlorodecanol
51309-10-5

10-chlorodecanol

A

9-Decen-1-ol
13019-22-2

9-Decen-1-ol

B

decamethylene oxide

decamethylene oxide

Conditions
ConditionsYield
With sodium hydroxide
10-chlorodecanol
51309-10-5

10-chlorodecanol

sodium hydroxide

sodium hydroxide

A

9-Decen-1-ol
13019-22-2

9-Decen-1-ol

B

decamethylene oxide

decamethylene oxide

Conditions
ConditionsYield
bei Destillation;
1,10-decadiene
1647-16-1

1,10-decadiene

A

1,10-Decanediol
112-47-0

1,10-Decanediol

B

1-Decanol
112-30-1

1-Decanol

C

9-Decen-1-ol
13019-22-2

9-Decen-1-ol

D

8-decene-1-ol
76501-46-7

8-decene-1-ol

Conditions
ConditionsYield
Stage #1: 1,10-decadiene With triisobutylaluminum; bis-triphenylphosphine-palladium(II) chloride In dichloromethane at 25℃; for 12h;
Stage #2: With sodium hydroxide; oxygen In dichloromethane
A 16 % Spectr.
B 27 % Spectr.
C 11 % Spectr.
D 24 % Spectr.
Methyl 10-undecenoate
111-81-9

Methyl 10-undecenoate

9-Decen-1-ol
13019-22-2

9-Decen-1-ol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: hydroboration-oxidation
2: 1M potassium methoxide / methanol / 40 °C / electrolysis: anode: platinum foil; current source: galvanostat; current density 200 mA cm-2; current consumption: 3.03 F mol-1; cell voltage 50-60 V
View Scheme
12-methoxy-12-oxododecanoic acid
3903-40-0

12-methoxy-12-oxododecanoic acid

9-Decen-1-ol
13019-22-2

9-Decen-1-ol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 1M potassium methoxide / methanol / 40 - 45 °C / electrolysis: anode: platinum foil; current source: galvanostat; current density 220 mA cm-2; current consumption: 1.25 F mol-1; cell voltage 40-70 V
2: hydroboration-oxidation
3: 1M potassium methoxide / methanol / 40 °C / electrolysis: anode: platinum foil; current source: galvanostat; current density 200 mA cm-2; current consumption: 3.03 F mol-1; cell voltage 50-60 V
View Scheme
dodecanedioic acid dimethyl ester
1731-79-9

dodecanedioic acid dimethyl ester

9-Decen-1-ol
13019-22-2

9-Decen-1-ol

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: barium hydroxide octahydrate / methanol / 4 d, -10 deg C; 10 h, RT
2: 1M potassium methoxide / methanol / 40 - 45 °C / electrolysis: anode: platinum foil; current source: galvanostat; current density 220 mA cm-2; current consumption: 1.25 F mol-1; cell voltage 40-70 V
3: hydroboration-oxidation
4: 1M potassium methoxide / methanol / 40 °C / electrolysis: anode: platinum foil; current source: galvanostat; current density 200 mA cm-2; current consumption: 3.03 F mol-1; cell voltage 50-60 V
View Scheme
oleyl acetate
693-80-1

oleyl acetate

9-Decen-1-ol
13019-22-2

9-Decen-1-ol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: (i) O3, CH2Cl2, (ii) Ph3P
2: (i) K, HMPT, (ii) /BRN= 1769551/
3: aq. NaOH / methanol
View Scheme
oleoyl alcohol
143-28-2

oleoyl alcohol

potassium permanganate

potassium permanganate

9-Decen-1-ol
13019-22-2

9-Decen-1-ol

Conditions
ConditionsYield
Multi-step reaction with 4 steps
2: (i) O3, CH2Cl2, (ii) Ph3P
3: (i) K, HMPT, (ii) /BRN= 1769551/
4: aq. NaOH / methanol
View Scheme
9-acetoxynonal
29541-97-7

9-acetoxynonal

9-Decen-1-ol
13019-22-2

9-Decen-1-ol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: (i) K, HMPT, (ii) /BRN= 1769551/
2: aq. NaOH / methanol
View Scheme
9-Decen-1-ol
13019-22-2

9-Decen-1-ol

9-decenal
39770-05-3

9-decenal

Conditions
ConditionsYield
With oxalyl dichloride; dimethyl sulfoxide; triethylamine In dichloromethane at -60 - 20℃; for 0.333333h;100%
With Bu4N In 1,2-dichloro-ethane at 50℃; for 9h;99%
With aluminum oxide; pyridinium chlorochromate In dichloromethane at 20℃; for 3h;97%
9-Decen-1-ol
13019-22-2

9-Decen-1-ol

10-bromodec-1-ene
62871-09-4

10-bromodec-1-ene

Conditions
ConditionsYield
With carbon tetrabromide; triphenylphosphine at 20℃; for 22h; Bromination;100%
With carbon tetrabromide; triphenylphosphine In dichloromethane at 0 - 20℃;100%
With carbon tetrabromide; triphenylphosphine In dichloromethane at 0 - 20℃; for 15h;100%
9-Decen-1-ol
13019-22-2

9-Decen-1-ol

9,10-dibromodecan-1-ol
114838-32-3

9,10-dibromodecan-1-ol

Conditions
ConditionsYield
With bromine In dichloromethane at -45 - 20℃;100%
With bromine In tetrachloromethane at -5℃; for 1h;95%
With bromine In dichloromethane
9-Decen-1-ol
13019-22-2

9-Decen-1-ol

methanesulfonyl chloride
124-63-0

methanesulfonyl chloride

dec-9-en-1-yl methanesulfonate
114640-35-6

dec-9-en-1-yl methanesulfonate

Conditions
ConditionsYield
With triethylamine In dichloromethane; water; sodium sulfate100%
With triethylamine In dichloromethane; water; sodium sulfate100%
With triethylamine In dichloromethane at 0℃; Inert atmosphere;100%
9-Decen-1-ol
13019-22-2

9-Decen-1-ol

p-toluenesulfonyl chloride
98-59-9

p-toluenesulfonyl chloride

9-decenyl p-toluenesulfonate
66605-77-4

9-decenyl p-toluenesulfonate

Conditions
ConditionsYield
With dmap; triethylamine In dichloromethane at 20℃;100%
With dmap; triethylamine In dichloromethane at 20℃; Inert atmosphere;100%
With pyridine at 0 - 5℃; for 3.5h; Inert atmosphere;97%
9-Decen-1-ol
13019-22-2

9-Decen-1-ol

tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

tert-butyl(dec-9-en-1-yloxy)dimethylsilane
185999-05-7

tert-butyl(dec-9-en-1-yloxy)dimethylsilane

Conditions
ConditionsYield
With 1H-imidazole In N,N-dimethyl-formamide at 20℃;100%
With 1H-imidazole; dmap In dichloromethane at 0 - 20℃; Inert atmosphere;99%
With 1H-imidazole; dmap98%
9-Decen-1-ol
13019-22-2

9-Decen-1-ol

10-iodo-1-decene
131034-47-4

10-iodo-1-decene

Conditions
ConditionsYield
With 1H-imidazole; iodine; triphenylphosphine In diethyl ether; acetonitrile at 20℃; for 4h;100%
With 1H-imidazole; iodine; triphenylphosphine In dichloromethane for 2h; Darkness; Inert atmosphere;91%
With 1H-imidazole; iodine88%
triethylsilane
617-86-7

triethylsilane

9-Decen-1-ol
13019-22-2

9-Decen-1-ol

1-(triethylsilyl)oxy-9-decene
566189-62-6

1-(triethylsilyl)oxy-9-decene

Conditions
ConditionsYield
AuCl(xanthphos) In acetone at 50℃; for 8h;100%
With copper (I) tert-butoxide; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In toluene at 25℃; for 2h;95%
9-Decen-1-ol
13019-22-2

9-Decen-1-ol

dec-9-en-1-yl methanesulfonate
114640-35-6

dec-9-en-1-yl methanesulfonate

Conditions
ConditionsYield
With triethylamine In dichloromethane100%
9-Decen-1-ol
13019-22-2

9-Decen-1-ol

benzoyl chloride
98-88-4

benzoyl chloride

dec-9-en-1-yl benzoate

dec-9-en-1-yl benzoate

Conditions
ConditionsYield
With pyridine In dichloromethane at 0 - 20℃; for 2h;100%
Stage #1: 9-Decen-1-ol With triethylamine In dichloromethane at 0℃; for 0.166667h; Inert atmosphere;
Stage #2: benzoyl chloride In dichloromethane at 0℃; for 0.5h; Inert atmosphere;
94%
With pyridine In dichloromethane
but-3-enoic acid
625-38-7

but-3-enoic acid

9-Decen-1-ol
13019-22-2

9-Decen-1-ol

C14H24O2
1259475-59-6

C14H24O2

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; Steglich Esterification;100%
9-Decen-1-ol
13019-22-2

9-Decen-1-ol

levulinic acid
123-76-2

levulinic acid

C15H26O3

C15H26O3

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; Inert atmosphere;100%
9-Decen-1-ol
13019-22-2

9-Decen-1-ol

acetic anhydride
108-24-7

acetic anhydride

9-decen-1-yl acetate
50816-18-7

9-decen-1-yl acetate

Conditions
ConditionsYield
With pyridine at 60℃; for 3h;99%
zeolite HSZ-360 In neat (no solvent) at 60℃; for 1h;97%
With sodium acetate at 68℃; for 4h; Schlenk technique; Inert atmosphere;95.6%
9-Decen-1-ol
13019-22-2

9-Decen-1-ol

10-chloro-1-decene
1002-70-6

10-chloro-1-decene

Conditions
ConditionsYield
With 2-chloro-1,3-dimethylimidazolinium chloride; triethylamine In dichloromethane at 20℃; for 21h; Chlorination;99%
With thionyl chloride In dichloromethane; N,N-dimethyl-formamide at 55℃; for 16h;93%
With N-chloro-succinimide; triphenylphosphine In tetrahydrofuran for 9h; Inert atmosphere;80%
9-Decen-1-ol
13019-22-2

9-Decen-1-ol

triisopropylsilyl trifluoromethanesulfonate
80522-42-5

triisopropylsilyl trifluoromethanesulfonate

(dec-9-en-1-yloxy)triisopropylsilane
214685-45-7

(dec-9-en-1-yloxy)triisopropylsilane

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0 - 20℃; Substitution;99%
9-Decen-1-ol
13019-22-2

9-Decen-1-ol

2,2,4,4-tetramethyl-1,3-oxazolidine-3-carbonyl chloride
146176-60-5

2,2,4,4-tetramethyl-1,3-oxazolidine-3-carbonyl chloride

dec-9-enyl 2,2,4,4-tetramethyl-1,3-oxazolidine-3-carboxylate
1048703-38-3

dec-9-enyl 2,2,4,4-tetramethyl-1,3-oxazolidine-3-carboxylate

Conditions
ConditionsYield
Stage #1: 9-Decen-1-ol With sodium hydride In tetrahydrofuran; mineral oil at 20℃; for 0.5h;
Stage #2: 2,2,4,4-tetramethyl-1,3-oxazolidine-3-carbonyl chloride In tetrahydrofuran; mineral oil at 80℃;
99%
9-Decen-1-ol
13019-22-2

9-Decen-1-ol

dec-9-enenitrile

dec-9-enenitrile

Conditions
ConditionsYield
Stage #1: 9-Decen-1-ol With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; iodine In dichloromethane at 0 - 20℃; for 1h; Inert atmosphere;
Stage #2: With ammonia; iodine In dichloromethane; water at 20℃; for 2h; Inert atmosphere;
99%
9-Decen-1-ol
13019-22-2

9-Decen-1-ol

[P(C2F5)3F2(dmap)]
1369421-74-8

[P(C2F5)3F2(dmap)]

[HDMAP][P(C2F5)3F2ODec]
1369421-86-2

[HDMAP][P(C2F5)3F2ODec]

Conditions
ConditionsYield
In diethyl ether at 20℃; for 1.5h;99%
9-Decen-1-ol
13019-22-2

9-Decen-1-ol

2-Bromoacetyl bromide
598-21-0

2-Bromoacetyl bromide

C12H21BrO3

C12H21BrO3

Conditions
ConditionsYield
With 1H-imidazole In dichloromethane at 0 - 20℃;99%
9-Decen-1-ol
13019-22-2

9-Decen-1-ol

tert-butylchlorodiphenylsilane
58479-61-1

tert-butylchlorodiphenylsilane

tert-butyl(dec-9-enyloxy)diphenylsilane

tert-butyl(dec-9-enyloxy)diphenylsilane

Conditions
ConditionsYield
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 48h; Inert atmosphere;99%
Stage #1: 9-Decen-1-ol With 1H-imidazole; dmap In dichloromethane at 0℃; for 0.0833333h; Inert atmosphere;
Stage #2: tert-butylchlorodiphenylsilane In dichloromethane at 0 - 20℃; for 3h; Inert atmosphere;
81%
9-Decen-1-ol
13019-22-2

9-Decen-1-ol

2-naphthaloyl chloride
2243-83-6

2-naphthaloyl chloride

dec-9-en-1-yl 2-naphthoate

dec-9-en-1-yl 2-naphthoate

Conditions
ConditionsYield
With dmap In dichloromethane at 0 - 20℃; Inert atmosphere;99%
9-Decen-1-ol
13019-22-2

9-Decen-1-ol

1-Decanol
112-30-1

1-Decanol

Conditions
ConditionsYield
With hydrogen; TMSB; palladium In ethanol at 20℃; under 760 Torr; for 17h;98%
Hydrogenation;
With amine functionalized polymer; carboxylic acid-derived silica colloids; hydrogen; carbocyclic acid-derived Pd-MMPC
9-Decen-1-ol
13019-22-2

9-Decen-1-ol

benzyl bromide
100-39-0

benzyl bromide

((dec-9-en-1-yloxy)methyl)benzene
100189-71-7

((dec-9-en-1-yloxy)methyl)benzene

Conditions
ConditionsYield
With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; for 2.25h;98%
With sodium hydride In tetrahydrofuran at 0 - 20℃; for 4h;95%
Stage #1: 9-Decen-1-ol With sodium hydride In nujol; N,N-dimethyl-formamide at 0 - 20℃; Inert atmosphere;
Stage #2: benzyl bromide In nujol; N,N-dimethyl-formamide at 20℃; Inert atmosphere;
93%
9-Decen-1-ol
13019-22-2

9-Decen-1-ol

ethyl acetate
141-78-6

ethyl acetate

9-decen-1-yl acetate
50816-18-7

9-decen-1-yl acetate

Conditions
ConditionsYield
With iodine for 2.5h; Reflux; chemoselective reaction;98%
titanium(IV) tetraethanolate for 24h;94%
9-Decen-1-ol
13019-22-2

9-Decen-1-ol

ethyl vinyl ether
109-92-2

ethyl vinyl ether

1-(α-ethoxyethoxy)dec-9-ene
302969-69-3

1-(α-ethoxyethoxy)dec-9-ene

Conditions
ConditionsYield
With pyridinium p-toluenesulfonate In dichloromethane at 20℃; for 0.25h; Inert atmosphere;98%
With pyridinium p-toluenesulfonate In dichloromethane at 20℃; for 16h;98%
With pyridinium p-toluenesulfonate In dichloromethane at 20℃; for 1.5h; Alkylation;92%
9-Decen-1-ol
13019-22-2

9-Decen-1-ol

hydrocinnamic acid chloride
645-45-4

hydrocinnamic acid chloride

9-decen-1-yl 3-phenylpropanoate

9-decen-1-yl 3-phenylpropanoate

Conditions
ConditionsYield
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;98%
With 1-methyl-1H-imidazole; N,N,N,N,-tetramethylethylenediamine; potassium carbonate In acetonitrile at 0 - 5℃; for 1h;98%
9-Decen-1-ol
13019-22-2

9-Decen-1-ol

2-(benzothiazol-2-ylsulfonyl)acetic acid

2-(benzothiazol-2-ylsulfonyl)acetic acid

C19H25NO4S2
1226981-24-3

C19H25NO4S2

Conditions
ConditionsYield
With dicyclohexyl-carbodiimide In tetrahydrofuran at 0 - 20℃; Inert atmosphere;98%
9-Decen-1-ol
13019-22-2

9-Decen-1-ol

3-phenylpropanoic acid methyl ester
103-25-3

3-phenylpropanoic acid methyl ester

9-decen-1-yl 3-phenylpropanoate

9-decen-1-yl 3-phenylpropanoate

Conditions
ConditionsYield
With chloro-trimethyl-silane; diphenylammonium trifluoromethanesulfonate In toluene at 80 - 110℃; for 24h; Esterification;97%
With sulfonated polypyrene In n-heptane at 80℃; for 16h;91%
With high p-toluenesulfonate content diphenylamine and terephthalaldehyde resin In neat (no solvent) at 110℃; for 6h;83%
2,6-Dibromopyridine
626-05-1

2,6-Dibromopyridine

9-Decen-1-ol
13019-22-2

9-Decen-1-ol

2,6-bis(9-decenyloxy)pyridine
533926-64-6

2,6-bis(9-decenyloxy)pyridine

Conditions
ConditionsYield
Stage #1: 9-Decen-1-ol With sodium In tetrahydrofuran Heating;
Stage #2: 2,6-Dibromopyridine In N,N-dimethyl-formamide at 95℃;
97%
Stage #1: 9-Decen-1-ol With sodium In tetrahydrofuran Heating;
Stage #2: 2,6-Dibromopyridine In N,N-dimethyl-formamide at 95℃; for 16h;
97%

13019-22-2Relevant articles and documents

A Selective Monodehydration of C4-14-α,ω-Alkanediols with Stearic and/or Palmitic Acids

Yamanaka, Tohr,Imai, Takashi

, p. 1585 - 1586 (1981)

The formation of monoesters of the C4-14-α,ω-alkanediol (1) with stearic and/or palmitic acids and the consecutive pyrolysis of the monoesters to an ω-alken-1-ol (2) were effected at 320-350 deg C under 260-760 mmHg in a backmix flow reactor of a constant volume equipped with a fractionating column, through which the unchanged 1 was partially recycled.The selectivity in the preparations of 2(C6, C10, C14) was greater than 79percent.

Subramaniam et al.

, p. 495 (1978)

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.

Ligand-free (: Z)-selective transfer semihydrogenation of alkynes catalyzed by in situ generated oxidizable copper nanoparticles

Grela, Karol,Kusy, Rafa?

supporting information, p. 5494 - 5502 (2021/08/16)

Herein, we present (Z)-selective transfer semihydrogenation of alkynes based on in situ generated CuNPs in the presence of hydrogen donors, such as ammonia-borane and a green protic solvent. This environmentally friendly method is characterized by operational simplicity combined with high stereo- and chemoselectivity and functional group compatibility. Auto-oxidation of CuNPs after the completion of a semihydrogenation reaction results in the formation of a water-soluble ammonia complex, so that the catalyst may be reused several times by simple phase-separation with no need for any special regeneration processes. Formed NH4B(OR)4 can be easily transformed back into ammonia-borane or into boric acid. In addition, a one-pot tandem sequence involving a Suzuki reaction followed by semihydrogenation was presented, which allows minimization of chemical waste production.

CYCLOALKYL-CONTAINING CARBOXYLIC ACIDS AND USES THEREOF

-

Page/Page column 47; 69; 80, (2021/06/26)

The present application discloses a compound of formula (I) or a salt thereof: (I) and compositions comprising such compound or salt thereof. The use of such compound, salt thereof or composition comprising same for treating anemia or leukopenia, fibrosis, cancer, hypertension and/or a metabolic condition in a subject is also disclosed.

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