Product Name

  • Name

    CIS-9-HEXADECENOL

  • EINECS 233-831-4
  • CAS No. 10378-01-5
  • Article Data21
  • CAS DataBase
  • Density 0.847 g/cm3
  • Solubility
  • Melting Point
  • Formula C16H32O
  • Boiling Point 340 °C at 760 mmHg
  • Molecular Weight 240.429
  • Flash Point 115.4 °C
  • Transport Information
  • Appearance
  • Safety
  • Risk Codes
  • Molecular Structure Molecular Structure of 10378-01-5 (CIS-9-HEXADECENOL)
  • Hazard Symbols
  • Synonyms 9-Hexadecen-1-ol,(Z)- (8CI);(Z)-9-Hexadecen-1-ol;9-cis-Hexadecenol;Palmitoleyl alcohol;cis-9-Hexadecen-1-ol;cis-9-Hexadecenol;cis-D9-Hexadecenol;
  • PSA 20.23000
  • LogP 5.23600

Synthetic route

cis-9-hexadecenoic acid
373-49-9

cis-9-hexadecenoic acid

palmitoleyl alcohol
10378-01-5

palmitoleyl alcohol

Conditions
ConditionsYield
With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; Reflux;98%
With lithium aluminium tetrahydride In diethyl ether at 20℃; for 24h;97%
Multi-step reaction with 2 steps
1: 0.19 g / conc. H2SO4 / 6 h / Heating
2: 0.14 g / LiAlH4 / tetrahydrofuran / 24 h / Ambient temperature
View Scheme
9-hexadecyn-1-ol
88109-73-3

9-hexadecyn-1-ol

palmitoleyl alcohol
10378-01-5

palmitoleyl alcohol

Conditions
ConditionsYield
With hydrogen; ethylendiamine poisoned P-2 Ni In ethanol97%
With hydrogen; Ni-P288%
With bis(cyclopentadienyl)titanium dichloride; di-iso-butylmagnesium; ammonium chloride 1.) Et2O, 20 deg C, 30 min, 2.) H2O; Yield given. Multistep reaction;
(Z)-9-hexadecenoic acid methyl ester
1120-25-8

(Z)-9-hexadecenoic acid methyl ester

palmitoleyl alcohol
10378-01-5

palmitoleyl alcohol

Conditions
ConditionsYield
With lithium aluminium tetrahydride In tetrahydrofuran at -10 - 20℃; for 5h;96%
With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; for 2h;92%
With lithium aluminium tetrahydride In tetrahydrofuran for 24h; Ambient temperature;0.14 g
With lithium aluminium tetrahydride In diethyl ether for 2h; Reflux;2.3 g
9-tetradecyn-1-ol
60037-69-6

9-tetradecyn-1-ol

palmitoleyl alcohol
10378-01-5

palmitoleyl alcohol

Conditions
ConditionsYield
With hydrogen; P2Ni86%
(Z)-hexadec-9-en-1-yl acetate
34010-20-3

(Z)-hexadec-9-en-1-yl acetate

palmitoleyl alcohol
10378-01-5

palmitoleyl alcohol

Conditions
ConditionsYield
With lithium aluminium tetrahydride In diethyl ether at 20℃; for 5h;82%
With sodium hydroxide In methanol
(Z)-tert-butyl(hexadec-9-en-1-yloxy)dimethylsilane

(Z)-tert-butyl(hexadec-9-en-1-yloxy)dimethylsilane

palmitoleyl alcohol
10378-01-5

palmitoleyl alcohol

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride In tetrahydrofuran at 0 - 20℃; for 3h;82%
heptanal
111-71-7

heptanal

(9-hydroxynonyl)(triphenyl)phosphonium bromide
73945-70-7

(9-hydroxynonyl)(triphenyl)phosphonium bromide

A

trans-hexadec-9-en-1-ol
64437-47-4

trans-hexadec-9-en-1-ol

B

palmitoleyl alcohol
10378-01-5

palmitoleyl alcohol

Conditions
ConditionsYield
With sodium hydride; dimethyl sulfoxide In tetrahydrofuran for 0.5h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
(Z)-16-(1-Ethoxy-ethoxy)-hexadec-7-ene

(Z)-16-(1-Ethoxy-ethoxy)-hexadec-7-ene

palmitoleyl alcohol
10378-01-5

palmitoleyl alcohol

Conditions
ConditionsYield
With toluene-4-sulfonic acid In methanol; water at 20℃; for 15h; Yield given;
2-[((Z)-Hexadec-9-enyl)oxy]-tetrahydro-pyran
99159-88-3

2-[((Z)-Hexadec-9-enyl)oxy]-tetrahydro-pyran

palmitoleyl alcohol
10378-01-5

palmitoleyl alcohol

Conditions
ConditionsYield
With toluene-4-sulfonic acid In methanol for 3h; Heating; Yield given;
With toluene-4-sulfonic acid In methanol at 20℃; for 16h;
(Z)-4-undecene-1-ol
21676-07-3

(Z)-4-undecene-1-ol

palmitoleyl alcohol
10378-01-5

palmitoleyl alcohol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 96 percent / triphenylphosphine, Br2 / CCl4 / 16 h / Ambient temperature
2: 1.) cuprous iodide, 2,2' bipyridyl / 1.) THF, 2 deg C, 10 min, 2.) THF, a) 2 deg C, 2 h, b) RT, 15 h
3: p-toluenesulfonic acid / methanol; H2O / 15 h / 20 °C
View Scheme
Multi-step reaction with 3 steps
1: 82 percent / PBr3, pyridine / diethyl ether / 1) rt, overnight, 2) reflux, 2 h
2: 1) Mg / 3) Li2CuCl4 / 1) THF, 2) THF, -10 deg C, 30 min, 3) a) 0 to -10 deg C, 6 h, b) rt, overnight
3: p-toluenesulphonic acid / methanol / 3 h / Heating
View Scheme
(Z)-4-undecenal
68820-32-6

(Z)-4-undecenal

palmitoleyl alcohol
10378-01-5

palmitoleyl alcohol

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 95 percent / diisobutylaluminum hydride / diethyl ether; toluene / 1.5 h / -10 °C
2: 96 percent / triphenylphosphine, Br2 / CCl4 / 16 h / Ambient temperature
3: 1.) cuprous iodide, 2,2' bipyridyl / 1.) THF, 2 deg C, 10 min, 2.) THF, a) 2 deg C, 2 h, b) RT, 15 h
4: p-toluenesulfonic acid / methanol; H2O / 15 h / 20 °C
View Scheme
(Z)-4-undecenyl bromide
109523-23-1

(Z)-4-undecenyl bromide

palmitoleyl alcohol
10378-01-5

palmitoleyl alcohol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1.) cuprous iodide, 2,2' bipyridyl / 1.) THF, 2 deg C, 10 min, 2.) THF, a) 2 deg C, 2 h, b) RT, 15 h
2: p-toluenesulfonic acid / methanol; H2O / 15 h / 20 °C
View Scheme
Multi-step reaction with 2 steps
1: 1) Mg / 3) Li2CuCl4 / 1) THF, 2) THF, -10 deg C, 30 min, 3) a) 0 to -10 deg C, 6 h, b) rt, overnight
2: p-toluenesulphonic acid / methanol / 3 h / Heating
View Scheme
1,1-dimethoxy-8-tosyloxy-(4Z)-octene
82861-01-6

1,1-dimethoxy-8-tosyloxy-(4Z)-octene

palmitoleyl alcohol
10378-01-5

palmitoleyl alcohol

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 63 percent / dilithium tetrachlorocuprate / tetrahydrofuran / 1.) -78 deg C, 2 h, 2.) RT, 15 h
2: 99 percent / 5percent HCl / acetone / 6 h / Ambient temperature
3: 95 percent / diisobutylaluminum hydride / diethyl ether; toluene / 1.5 h / -10 °C
4: 96 percent / triphenylphosphine, Br2 / CCl4 / 16 h / Ambient temperature
5: 1.) cuprous iodide, 2,2' bipyridyl / 1.) THF, 2 deg C, 10 min, 2.) THF, a) 2 deg C, 2 h, b) RT, 15 h
6: p-toluenesulfonic acid / methanol; H2O / 15 h / 20 °C
View Scheme
1,1-dimethoxy-(4Z)-undecene
104187-94-2

1,1-dimethoxy-(4Z)-undecene

palmitoleyl alcohol
10378-01-5

palmitoleyl alcohol

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 99 percent / 5percent HCl / acetone / 6 h / Ambient temperature
2: 95 percent / diisobutylaluminum hydride / diethyl ether; toluene / 1.5 h / -10 °C
3: 96 percent / triphenylphosphine, Br2 / CCl4 / 16 h / Ambient temperature
4: 1.) cuprous iodide, 2,2' bipyridyl / 1.) THF, 2 deg C, 10 min, 2.) THF, a) 2 deg C, 2 h, b) RT, 15 h
5: p-toluenesulfonic acid / methanol; H2O / 15 h / 20 °C
View Scheme
methyl aleuritate

methyl aleuritate

palmitoleyl alcohol
10378-01-5

palmitoleyl alcohol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: 60.91 percent / aq. NaIO4 / acetonitrile / 0.5 h / 5 °C
2.1: sodium amide / tetrahydrofuran; hexamethylphosphoric acid triamide / 1.5 h / 20 °C
2.2: 91.52 percent / tetrahydrofuran; hexamethylphosphoric acid triamide / -73 - 20 °C
3.1: 92 percent / lithium aluminum hydride / tetrahydrofuran / 2 h / 0 °C
View Scheme
methyl ester of azelaic acid aldehyde
1931-63-1

methyl ester of azelaic acid aldehyde

palmitoleyl alcohol
10378-01-5

palmitoleyl alcohol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: sodium amide / tetrahydrofuran; hexamethylphosphoric acid triamide / 1.5 h / 20 °C
1.2: 91.52 percent / tetrahydrofuran; hexamethylphosphoric acid triamide / -73 - 20 °C
2.1: 92 percent / lithium aluminum hydride / tetrahydrofuran / 2 h / 0 °C
View Scheme
Multi-step reaction with 2 steps
1: 1.) NaNH2 / 1.) THF, RT, 1 h, 2.) THF, from -10 deg C to RT
2: 96 percent / LAH / tetrahydrofuran / 5 h / -10 - 20 °C
View Scheme
Multi-step reaction with 2 steps
1: potassium carbonate / toluene / 4 h / Reflux
2: lithium aluminium tetrahydride / diethyl ether / 2 h / Reflux
View Scheme
triphenylheptylphosphonium bromide
13423-48-8

triphenylheptylphosphonium bromide

palmitoleyl alcohol
10378-01-5

palmitoleyl alcohol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: sodium amide / tetrahydrofuran; hexamethylphosphoric acid triamide / 1.5 h / 20 °C
1.2: 91.52 percent / tetrahydrofuran; hexamethylphosphoric acid triamide / -73 - 20 °C
2.1: 92 percent / lithium aluminum hydride / tetrahydrofuran / 2 h / 0 °C
View Scheme
Multi-step reaction with 2 steps
1: 1.) sodium bis(trimethylsilyl)amide / 1.) THF, from 50 to 55 deg C, 60 min, 2.) THF, a) -78 deg C, 30 min, b) 20 deg C, 12 h
2: 82 percent / LiAlH4 / diethyl ether / 5 h / 20 °C
View Scheme
(+)-threo-9,10,16-trihydroxyhexadecanoic acid

(+)-threo-9,10,16-trihydroxyhexadecanoic acid

palmitoleyl alcohol
10378-01-5

palmitoleyl alcohol

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: 97.95 percent / aq. H2SO4 / 0.11 h / microwave irradiation
2.1: 60.91 percent / aq. NaIO4 / acetonitrile / 0.5 h / 5 °C
3.1: sodium amide / tetrahydrofuran; hexamethylphosphoric acid triamide / 1.5 h / 20 °C
3.2: 91.52 percent / tetrahydrofuran; hexamethylphosphoric acid triamide / -73 - 20 °C
4.1: 92 percent / lithium aluminum hydride / tetrahydrofuran / 2 h / 0 °C
View Scheme
8-Bromo-1-octene
2695-48-9

8-Bromo-1-octene

palmitoleyl alcohol
10378-01-5

palmitoleyl alcohol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 87 percent / NH3
2: 1) 9-BBN, 2) H2O2, AcONa
3: 88 percent / H2 / Ni-P2
View Scheme
1-octynyllithium
21433-45-4

1-octynyllithium

palmitoleyl alcohol
10378-01-5

palmitoleyl alcohol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 87 percent / NH3
2: 1) 9-BBN, 2) H2O2, AcONa
3: 88 percent / H2 / Ni-P2
View Scheme
hexadec-1-en-9-yne
197901-27-2

hexadec-1-en-9-yne

palmitoleyl alcohol
10378-01-5

palmitoleyl alcohol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1) 9-BBN, 2) H2O2, AcONa
2: 88 percent / H2 / Ni-P2
View Scheme
10,11-dibromo-undecanoic acid
6308-96-9

10,11-dibromo-undecanoic acid

palmitoleyl alcohol
10378-01-5

palmitoleyl alcohol

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: KOH, PEG 400 / 0.5 h / 150 - 200 °C
2: p-TSA / 12 h / Ambient temperature
3: 96 percent / H2, quinoline / 5percent Pd/BaSO4 / hexane / Ambient temperature
4: 84 percent / O3 / CH2Cl2 / -78 °C
5: 1.) NaNH2 / 1.) THF, RT, 1 h, 2.) THF, from -10 deg C to RT
6: 96 percent / LAH / tetrahydrofuran / 5 h / -10 - 20 °C
View Scheme
10-undecenoic acid
112-38-9

10-undecenoic acid

aqueous KOH-solution

aqueous KOH-solution

palmitoleyl alcohol
10378-01-5

palmitoleyl alcohol

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: 97 percent / Br2 / CCl4 / 1.5 h
2: KOH, PEG 400 / 0.5 h / 150 - 200 °C
3: p-TSA / 12 h / Ambient temperature
4: 96 percent / H2, quinoline / 5percent Pd/BaSO4 / hexane / Ambient temperature
5: 84 percent / O3 / CH2Cl2 / -78 °C
6: 1.) NaNH2 / 1.) THF, RT, 1 h, 2.) THF, from -10 deg C to RT
7: 96 percent / LAH / tetrahydrofuran / 5 h / -10 - 20 °C
View Scheme
9-undecynoic acid
22202-65-9

9-undecynoic acid

hydrogen

hydrogen

palmitoleyl alcohol
10378-01-5

palmitoleyl alcohol

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: p-TSA / 12 h / Ambient temperature
2: 96 percent / H2, quinoline / 5percent Pd/BaSO4 / hexane / Ambient temperature
3: 84 percent / O3 / CH2Cl2 / -78 °C
4: 1.) NaNH2 / 1.) THF, RT, 1 h, 2.) THF, from -10 deg C to RT
5: 96 percent / LAH / tetrahydrofuran / 5 h / -10 - 20 °C
View Scheme
9-undecynoic acid methyl ester
18937-76-3

9-undecynoic acid methyl ester

palmitoleyl alcohol
10378-01-5

palmitoleyl alcohol

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 96 percent / H2, quinoline / 5percent Pd/BaSO4 / hexane / Ambient temperature
2: 84 percent / O3 / CH2Cl2 / -78 °C
3: 1.) NaNH2 / 1.) THF, RT, 1 h, 2.) THF, from -10 deg C to RT
4: 96 percent / LAH / tetrahydrofuran / 5 h / -10 - 20 °C
View Scheme
(Z)-0-undecenoic acid methyl ester
54299-07-9

(Z)-0-undecenoic acid methyl ester

palmitoleyl alcohol
10378-01-5

palmitoleyl alcohol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 84 percent / O3 / CH2Cl2 / -78 °C
2: 1.) NaNH2 / 1.) THF, RT, 1 h, 2.) THF, from -10 deg C to RT
3: 96 percent / LAH / tetrahydrofuran / 5 h / -10 - 20 °C
View Scheme
2-(8-bromooctyloxy)tetrahydropyran
50816-20-1

2-(8-bromooctyloxy)tetrahydropyran

palmitoleyl alcohol
10378-01-5

palmitoleyl alcohol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 1.) LiNH2, HMPTA / 1.) RT, 1 h, 2.) a) 10 deg C, 1 h, b) RT, 15 h, c) 55 deg C, 10 h
2: 85 percent / p-TsOH / methanol; H2O / 18 h / 20 °C
3: 1.) iso-BuMgBr, 2.) Cp2TiCl2 / 1.) diethyl ether, 0 deg C, 15 min, 2.) diethyl ether, RT, 3 h
View Scheme
Multi-step reaction with 3 steps
1.1: n-butyllithium / hexane; tetrahydrofuran / 1 h / -30 - 0 °C / Inert atmosphere
1.2: 16 h / Reflux
2.1: potassium hydroxide; palladium diacetate / N,N-dimethyl-formamide / 16 h / 145 °C / Sealed tube
3.1: toluene-4-sulfonic acid / methanol / 16 h / 20 °C
View Scheme
1,8-Octanediol
629-41-4

1,8-Octanediol

primary-secondary glycol C8H18O2

primary-secondary glycol C8H18O2

palmitoleyl alcohol
10378-01-5

palmitoleyl alcohol

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 75 percent / 48percent HBr / Heating
2: 99 percent / p-toluenesulfonic acid
3: 1.) LiNH2, HMPTA / 1.) RT, 1 h, 2.) a) 10 deg C, 1 h, b) RT, 15 h, c) 55 deg C, 10 h
4: 85 percent / p-TsOH / methanol; H2O / 18 h / 20 °C
5: 1.) iso-BuMgBr, 2.) Cp2TiCl2 / 1.) diethyl ether, 0 deg C, 15 min, 2.) diethyl ether, RT, 3 h
View Scheme
8-bromooctanol
50816-19-8

8-bromooctanol

palmitoleyl alcohol
10378-01-5

palmitoleyl alcohol

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 99 percent / p-toluenesulfonic acid
2: 1.) LiNH2, HMPTA / 1.) RT, 1 h, 2.) a) 10 deg C, 1 h, b) RT, 15 h, c) 55 deg C, 10 h
3: 85 percent / p-TsOH / methanol; H2O / 18 h / 20 °C
4: 1.) iso-BuMgBr, 2.) Cp2TiCl2 / 1.) diethyl ether, 0 deg C, 15 min, 2.) diethyl ether, RT, 3 h
View Scheme
Multi-step reaction with 4 steps
1.1: toluene-4-sulfonic acid / dichloromethane / 16.5 h / 0 - 20 °C
2.1: n-butyllithium / hexane; tetrahydrofuran / 1 h / -30 - 0 °C / Inert atmosphere
2.2: 16 h / Reflux
3.1: potassium hydroxide; palladium diacetate / N,N-dimethyl-formamide / 16 h / 145 °C / Sealed tube
4.1: toluene-4-sulfonic acid / methanol / 16 h / 20 °C
View Scheme
1-tetrahydropyranyloxy-n-9-hexadecyn
25258-24-6

1-tetrahydropyranyloxy-n-9-hexadecyn

palmitoleyl alcohol
10378-01-5

palmitoleyl alcohol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 85 percent / p-TsOH / methanol; H2O / 18 h / 20 °C
2: 1.) iso-BuMgBr, 2.) Cp2TiCl2 / 1.) diethyl ether, 0 deg C, 15 min, 2.) diethyl ether, RT, 3 h
View Scheme
Multi-step reaction with 2 steps
1: potassium hydroxide; palladium diacetate / N,N-dimethyl-formamide / 16 h / 145 °C / Sealed tube
2: toluene-4-sulfonic acid / methanol / 16 h / 20 °C
View Scheme
palmitoleyl alcohol
10378-01-5

palmitoleyl alcohol

(Z)-9-hexadecenal
56219-04-6

(Z)-9-hexadecenal

Conditions
ConditionsYield
With pyridinium chlorochromate In dichloromethane at 20℃; for 2h;98%
With pyridinium chlorochromate In dichloromethane for 1.5h; Ambient temperature;94%
With pyridinium chlorochromate94%
palmitoleyl alcohol
10378-01-5

palmitoleyl alcohol

(Z)-hexadec-9-enyl bromide
132538-05-7

(Z)-hexadec-9-enyl bromide

Conditions
ConditionsYield
With bromine; triphenylphosphine In benzene at 20℃; for 3h;97%
With carbon tetrabromide; triphenylphosphine In dichloromethane for 16h; Ambient temperature;94%
With carbon tetrabromide; triphenylphosphine In dichloromethane at 20℃; for 16h;94%
palmitoleyl alcohol
10378-01-5

palmitoleyl alcohol

(Z)-16-iodohexadec-7-ene

(Z)-16-iodohexadec-7-ene

Conditions
ConditionsYield
With 1H-imidazole; iodine; triphenylphosphine In toluene at 20℃; for 3h;89%
palmitoleyl alcohol
10378-01-5

palmitoleyl alcohol

acetic anhydride
108-24-7

acetic anhydride

(Z)-hexadec-9-en-1-yl acetate
34010-20-3

(Z)-hexadec-9-en-1-yl acetate

Conditions
ConditionsYield
With pyridine for 1h; Ambient temperature;85%
With pyridine for 24h; Ambient temperature;68%
With pyridine for 25h; Ambient temperature;0.1 g
In pyridine at 20℃; for 24h;1.4 g
cholesteryl p-toluenesulfonate
1182-65-6, 3381-56-4

cholesteryl p-toluenesulfonate

palmitoleyl alcohol
10378-01-5

palmitoleyl alcohol

cholesteryl cis-9'-hexadecenyl ether
74996-37-5

cholesteryl cis-9'-hexadecenyl ether

Conditions
ConditionsYield
at 110℃; for 2.5h;54.1%
palmitoleyl alcohol
10378-01-5

palmitoleyl alcohol

methanesulfonyl chloride
124-63-0

methanesulfonyl chloride

palmitoleyl methanesulfonate
93135-85-4

palmitoleyl methanesulfonate

Conditions
ConditionsYield
With pyridine
With pyridine at 0 - 20℃; for 24h;
methanol
67-56-1

methanol

palmitoleyl alcohol
10378-01-5

palmitoleyl alcohol

A

10-Methoxy-hexadecan-1-ol

10-Methoxy-hexadecan-1-ol

B

9-Methoxy-hexadecan-1-ol

9-Methoxy-hexadecan-1-ol

Conditions
ConditionsYield
With sodium tetrahydroborate; mercury(II) diacetate 1.) 48 h, RT; 2.) glacial acetic acid; Multistep reaction;
palmitoleyl alcohol
10378-01-5

palmitoleyl alcohol

tert-butyl [4-hydroxy-3-(10(Z)-heptadecenyl)]phenyl carbonate

tert-butyl [4-hydroxy-3-(10(Z)-heptadecenyl)]phenyl carbonate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: 97 percent / PPh3; Br2 / benzene / 3 h / 20 °C
2.1: Mg / tetrahydrofuran / 4 h / Heating
2.2: 12 mg / NaH / diethyl ether / 1.5 h / 0 - 20 °C
View Scheme
palmitoleyl alcohol
10378-01-5

palmitoleyl alcohol

tert-butyl [2-bromo-3-hydroxy-4-(10(Z)-heptadecenyl)]phenyl carbonate

tert-butyl [2-bromo-3-hydroxy-4-(10(Z)-heptadecenyl)]phenyl carbonate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: 97 percent / PPh3; Br2 / benzene / 3 h / 20 °C
2.1: Mg / tetrahydrofuran / 4 h / Heating
2.2: 0.920 g / NaH / diethyl ether / 1.5 h / 0 - 20 °C
View Scheme
palmitoleyl alcohol
10378-01-5

palmitoleyl alcohol

(3S,8aR)-5-Bromo-8a-((Z)-heptadec-10-enyl)-3-methyl-8aH-benzo[1,4]dioxine-2,6-dione
903522-41-8

(3S,8aR)-5-Bromo-8a-((Z)-heptadec-10-enyl)-3-methyl-8aH-benzo[1,4]dioxine-2,6-dione

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: 97 percent / PPh3; Br2 / benzene / 3 h / 20 °C
2.1: Mg / tetrahydrofuran / 4 h / Heating
2.2: 0.920 g / NaH / diethyl ether / 1.5 h / 0 - 20 °C
3.1: 92 percent / K2CO3 / dimethylformamide / 6 h / 20 °C
4.1: 93 percent / ZnBr; CH3NO2 / 20 °C
5.1: 55 percent / PhIOTMS(OTf); TMSOTf / CH2Cl2 / 0.25 h / 0 °C
View Scheme
palmitoleyl alcohol
10378-01-5

palmitoleyl alcohol

2-(2-bromo-6-heptadec-10-enyl-3-hydroxy-phenoxy)-N-methoxy-N-methyl-propionamide
903522-40-7

2-(2-bromo-6-heptadec-10-enyl-3-hydroxy-phenoxy)-N-methoxy-N-methyl-propionamide

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: 97 percent / PPh3; Br2 / benzene / 3 h / 20 °C
2.1: Mg / tetrahydrofuran / 4 h / Heating
2.2: 0.920 g / NaH / diethyl ether / 1.5 h / 0 - 20 °C
3.1: 92 percent / K2CO3 / dimethylformamide / 6 h / 20 °C
4.1: 93 percent / ZnBr; CH3NO2 / 20 °C
View Scheme
palmitoleyl alcohol
10378-01-5

palmitoleyl alcohol

2,2-Dimethyl-propionic acid 2-bromo-4-((Z)-heptadec-10-enyl)-3-[(S)-1-(methoxy-methyl-carbamoyl)-ethoxy]-phenyl ester

2,2-Dimethyl-propionic acid 2-bromo-4-((Z)-heptadec-10-enyl)-3-[(S)-1-(methoxy-methyl-carbamoyl)-ethoxy]-phenyl ester

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: 97 percent / PPh3; Br2 / benzene / 3 h / 20 °C
2.1: Mg / tetrahydrofuran / 4 h / Heating
2.2: 0.920 g / NaH / diethyl ether / 1.5 h / 0 - 20 °C
3.1: 92 percent / K2CO3 / dimethylformamide / 6 h / 20 °C
View Scheme
palmitoleyl alcohol
10378-01-5

palmitoleyl alcohol

2-(10(Z)-heptadecenyl)-1,4-hydroquinone

2-(10(Z)-heptadecenyl)-1,4-hydroquinone

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: 97 percent / PPh3; Br2 / benzene / 3 h / 20 °C
2.1: Mg / tetrahydrofuran / 4 h / Heating
2.2: 12 mg / NaH / diethyl ether / 1.5 h / 0 - 20 °C
3.1: 90 percent / HCl / dioxane / 1.25 h / 80 °C
View Scheme

9-Hexadecen-1-ol, (9Z)- Specification

The 9-Hexadecen-1-ol, (9Z)-, with the CAS registry number 10378-01-5, is also known as cis-9-Hexadecenol. Its EINECS registry number is 233-831-4. This chemical's molecular formula is C16H32O and molecular weight is 240.42. Its IUPAC name is called (Z)-hexadec-9-en-1-ol.

Physical properties of 9-Hexadecen-1-ol, (9Z)-: (1)ACD/LogP: 6.73; (2)# of Rule of 5 Violations: 1; (3)#H bond acceptors: 1; (4)#H bond donors: 1; (5)#Freely Rotating Bonds: 14; (6)Index of Refraction: 1.46; (7)Molar Refractivity: 77.76 cm3; (8)Molar Volume: 283.7 cm3; (9)Surface Tension: 31.5 dyne/cm; (10)Density: 0.847 g/cm3; (11)Flash Point: 115.4 °C; (12)Enthalpy of Vaporization: 67.6 kJ/mol; (13)Boiling Point: 340 °C at 760 mmHg; (14)Vapour Pressure: 5.88E-06 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)Canonical SMILES: CCCCCCC=CCCCCCCCCO
(2)Isomeric SMILES: CCCCCC/C=C\CCCCCCCCO
(3)InChI: InChI=1S/C16H32O/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17/h7-8,17H,2-6,9-16H2,1H3/b8-7-
(4)InChIKey: LBIYNOAMNIKVKF-FPLPWBNLSA-N

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