(Z)-Dodec-8-enyl acetate supplier

Name
(Z)-8-DODECEN-1-YL ACETATE
EINECS 248-823-6
CAS No. 28079-04-1
Article Data30
CAS DataBase
Density 0.881 g/cm³
Solubility
Melting Point
Formula C₁₄H₂₆O₂
Boiling Point 300.1 °C at 760 mmHg
Molecular Weight 226.359
Flash Point 96.5 °C
Transport Information
Appearance
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms 8-Dodecen-1-ol,acetate, (8Z)- (9CI);8-Dodecen-1-ol, acetate, (Z)- (8CI);(8Z)-Dodec-8-en-1-olacetate;(Z)-8-Dodecen-1-ol acetate;(Z)-8-Dodecen-1-yl acetate;(Z)-8-Dodecenyl acetate;Denacil;Funemone;GM;Orfamone;cis-8-Dodecen-1-yl acetate;8-Dodecen-1-ol,1-acetate, (8Z)-;
PSA 26.30000
LogP 4.24640

Synthetic route

: 26906-26-3
1-Acetoxydodec-8-yne

: 28079-04-1
(Z)-8-dodecen-1-yl acetate

Conditions

Conditions	Yield
With quinoline; hydrogen; Pd-BaSO4 In methanol	97%
With hydrogen; Lindlar's catalyst In hexane at 15℃;	7 g

: 40642-40-8
(Z)-8-dodecenol

: 75-36-5
acetyl chloride

: 28079-04-1
(Z)-8-dodecen-1-yl acetate

Conditions

Conditions	Yield
In pyridine	95%
With pyridine In benzene

: 153123-34-3
Δ8-dodecen-1-ol

: 108-24-7
acetic anhydride

: 28079-04-1
(Z)-8-dodecen-1-yl acetate

Conditions

Conditions	Yield
With pyridine at 5 - 25℃; for 2h; Large scale;	95%

: 40642-40-8
(Z)-8-dodecenol

: 108-24-7
acetic anhydride

: 28079-04-1
(Z)-8-dodecen-1-yl acetate

Conditions

Conditions	Yield
With pyridine In dichloromethane at 20℃; for 12h; Inert atmosphere; chemoselective reaction;	90%
With pyridine	89%
In pyridine for 24h; Ambient temperature;	75%

: 98398-50-6
(Z)-1-(2-tetrahydropyranyloxy)dodec-8-ene

: 75-36-5
acetyl chloride

: 28079-04-1
(Z)-8-dodecen-1-yl acetate

Conditions

Conditions	Yield
With acetic acid at 60℃; for 6h;	77%

: 109-67-1
1-penten

: 13038-22-7
non-8-en-1-yl acetate

: 28079-04-1
(Z)-8-dodecen-1-yl acetate

Conditions

Conditions	Yield
With C32H41N3O4Ru In tetrahydrofuran at 20℃; for 4h; Inert atmosphere; Glovebox; chemoselective reaction;	65%
With C35H47N3O4Ru In tetrahydrofuran at 35℃; for 2h;	58%
With Z-selective metathesis catalyst
With Z-selective cross-metathesis catalyst Inert atmosphere;

: Acetic acid (Z)-6-(toluene-4-sulfonyloxy)-dodec-8-enyl ester

: 28079-04-1
(Z)-8-dodecen-1-yl acetate

Conditions

Conditions	Yield
With sodium tetrahydroborate In dimethyl sulfoxide at 80℃;	58%

: 38363-29-0
(E)-8-dodecenyl acetate

: 28079-04-1
(Z)-8-dodecen-1-yl acetate

Conditions

Conditions	Yield
(i) HCl, (ii) NBS, (iii) NaI, DMF; Multistep reaction;

: 153123-34-3
Δ8-dodecen-1-ol

: 108-24-7
acetic anhydride

A: 28079-04-1
(Z)-8-dodecen-1-yl acetate

B: 38363-29-0
(E)-8-dodecenyl acetate

Conditions

Conditions	Yield
With pyridine Yield given. Yields of byproduct given;
With pyridine at 5 - 25℃; for 2h; Overall yield = 93.3 %; Overall yield = 0.57 kg;	A n/a B n/a

...Expand

: 108-24-7
acetic anhydride

: 98398-50-6
(Z)-1-(2-tetrahydropyranyloxy)dodec-8-ene

: 28079-04-1
(Z)-8-dodecen-1-yl acetate

Conditions

Conditions	Yield
With pyridine; water; toluene-4-sulfonic acid 1) MeOH, room temp., 15 h; 2) room temp., 24 h.; Yield given. Multistep reaction;

: 1779-51-7
n-butyl(triphenyl)phosphonium bromide

A: 28079-04-1
(Z)-8-dodecen-1-yl acetate

B: 38363-29-0
(E)-8-dodecenyl acetate

Conditions

Conditions	Yield
n-butyl(triphenyl)phosphonium bromide With n-butyllithium In tetrahydrofuran; hexane at 18℃; for 2h; Further stages. Title compound not separated from byproducts.;

: 627-19-0
1-Pentyne

: 28079-04-1
(Z)-8-dodecen-1-yl acetate

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: NaH / dimethylsulfoxide 2: LiAlH4 / diethyl ether 3: H2 / Lindlar catalyst / methanol 4: Py / benzene View Scheme

: 39924-26-0
(Z)-oct-4-enal

: 28079-04-1
(Z)-8-dodecen-1-yl acetate

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 95 percent / diisobutylaluminum hydride / diethyl ether; toluene / 2 h / -10 °C 2: 90 percent / triphenylphosphine, bromine / CCl4 / 1) 15 deg C, 1 h; 2) room temp., 15 h. 3: 1) cuprous iodide, 2,2'-bipyridyl 2) Mg / 1) abs. THF, 20 deg C, 0.5 h; 2) abs. THF, 2 h at 2 deg C and 15 h at room temp. 4: 1) p-toluenesulfonic acid, water; 2) pyridine / 1) MeOH, room temp., 15 h; 2) room temp., 24 h. View Scheme

Yield

Multi-step reaction with 4 steps
1: 95 percent / diisobutylaluminum hydride / diethyl ether; toluene / 2 h / -10 °C
2: 90 percent / triphenylphosphine, bromine / CCl4 / 1) 15 deg C, 1 h; 2) room temp., 15 h.
3: 1) cuprous iodide, 2,2'-bipyridyl 2) Mg / 1) abs. THF, 20 deg C, 0.5 h; 2) abs. THF, 2 h at 2 deg C and 15 h at room temp.
4: 1) p-toluenesulfonic acid, water; 2) pyridine / 1) MeOH, room temp., 15 h; 2) room temp., 24 h.
View Scheme

: 821-57-8
7-chloroheptanoic acid

: 28079-04-1
(Z)-8-dodecen-1-yl acetate

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: NaH / dimethylsulfoxide 2: LiAlH4 / diethyl ether 3: H2 / Lindlar catalyst / methanol 4: Py / benzene View Scheme

: 54393-36-1
(Z)-4-octene-1-ol

: 28079-04-1
(Z)-8-dodecen-1-yl acetate

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 90 percent / triphenylphosphine, bromine / CCl4 / 1) 15 deg C, 1 h; 2) room temp., 15 h. 2: 1) cuprous iodide, 2,2'-bipyridyl 2) Mg / 1) abs. THF, 20 deg C, 0.5 h; 2) abs. THF, 2 h at 2 deg C and 15 h at room temp. 3: 1) p-toluenesulfonic acid, water; 2) pyridine / 1) MeOH, room temp., 15 h; 2) room temp., 24 h. View Scheme

: 41589-71-3
8-Dodecyn-1-ol

: 28079-04-1
(Z)-8-dodecen-1-yl acetate

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: H2 / Lindlar catalyst / methanol 2: Py / benzene View Scheme
Multi-step reaction with 2 steps 1: 85 percent / H2 / Ni-P2 2: 89 percent / pyridine View Scheme
Multi-step reaction with 2 steps 1: 1) 9-borabicyclo<3.3.1>nonane, 2) CH3CO2H / 1) THF, 0 deg C, 24 h, 2) reflux, 9 h 2: pyridine / 15 h / 20 °C View Scheme

: 18545-07-8
8-Dodecinsaeure

: 28079-04-1
(Z)-8-dodecen-1-yl acetate

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: LiAlH4 / diethyl ether 2: H2 / Lindlar catalyst / methanol 3: Py / benzene View Scheme

: 82861-01-6
1,1-dimethoxy-8-tosyloxy-(4Z)-octene

: 28079-04-1
(Z)-8-dodecen-1-yl acetate

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1: 85 percent / NaI, zinc dust / bis-(2-methoxy-ethyl) ether / 1.5 h / 65 - 70 °C 2: 95 percent / 5percent aq. HCl / acetone / 6 h / Ambient temperature 3: 95 percent / diisobutylaluminum hydride / diethyl ether; toluene / 2 h / -10 °C 4: 90 percent / triphenylphosphine, bromine / CCl4 / 1) 15 deg C, 1 h; 2) room temp., 15 h. 5: 1) cuprous iodide, 2,2'-bipyridyl 2) Mg / 1) abs. THF, 20 deg C, 0.5 h; 2) abs. THF, 2 h at 2 deg C and 15 h at room temp. 6: 1) p-toluenesulfonic acid, water; 2) pyridine / 1) MeOH, room temp., 15 h; 2) room temp., 24 h. View Scheme

Yield

Multi-step reaction with 6 steps
1: 85 percent / NaI, zinc dust / bis-(2-methoxy-ethyl) ether / 1.5 h / 65 - 70 °C
2: 95 percent / 5percent aq. HCl / acetone / 6 h / Ambient temperature
3: 95 percent / diisobutylaluminum hydride / diethyl ether; toluene / 2 h / -10 °C
4: 90 percent / triphenylphosphine, bromine / CCl4 / 1) 15 deg C, 1 h; 2) room temp., 15 h.
5: 1) cuprous iodide, 2,2'-bipyridyl 2) Mg / 1) abs. THF, 20 deg C, 0.5 h; 2) abs. THF, 2 h at 2 deg C and 15 h at room temp.
6: 1) p-toluenesulfonic acid, water; 2) pyridine / 1) MeOH, room temp., 15 h; 2) room temp., 24 h.
View Scheme

: 119265-28-0
1,1-dimethoxy-4Z-octene

: 28079-04-1
(Z)-8-dodecen-1-yl acetate

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: 95 percent / 5percent aq. HCl / acetone / 6 h / Ambient temperature 2: 95 percent / diisobutylaluminum hydride / diethyl ether; toluene / 2 h / -10 °C 3: 90 percent / triphenylphosphine, bromine / CCl4 / 1) 15 deg C, 1 h; 2) room temp., 15 h. 4: 1) cuprous iodide, 2,2'-bipyridyl 2) Mg / 1) abs. THF, 20 deg C, 0.5 h; 2) abs. THF, 2 h at 2 deg C and 15 h at room temp. 5: 1) p-toluenesulfonic acid, water; 2) pyridine / 1) MeOH, room temp., 15 h; 2) room temp., 24 h. View Scheme

Yield

Multi-step reaction with 5 steps
1: 95 percent / 5percent aq. HCl / acetone / 6 h / Ambient temperature
2: 95 percent / diisobutylaluminum hydride / diethyl ether; toluene / 2 h / -10 °C
3: 90 percent / triphenylphosphine, bromine / CCl4 / 1) 15 deg C, 1 h; 2) room temp., 15 h.
4: 1) cuprous iodide, 2,2'-bipyridyl 2) Mg / 1) abs. THF, 20 deg C, 0.5 h; 2) abs. THF, 2 h at 2 deg C and 15 h at room temp.
5: 1) p-toluenesulfonic acid, water; 2) pyridine / 1) MeOH, room temp., 15 h; 2) room temp., 24 h.
View Scheme

: 79837-81-3
(Z)-1-bromo-4-octene

: 28079-04-1
(Z)-8-dodecen-1-yl acetate

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 1) cuprous iodide, 2,2'-bipyridyl 2) Mg / 1) abs. THF, 20 deg C, 0.5 h; 2) abs. THF, 2 h at 2 deg C and 15 h at room temp. 2: 1) p-toluenesulfonic acid, water; 2) pyridine / 1) MeOH, room temp., 15 h; 2) room temp., 24 h. View Scheme

: 4117-09-3
7-bromo-hept-1-ene

: 28079-04-1
(Z)-8-dodecen-1-yl acetate

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 89 percent / NH2 / tetrahydrofuran; dimethylsulfoxide 2: 1) 9-BBN, 2) H2O2, AcONa 3: 85 percent / H2 / Ni-P2 4: 89 percent / pyridine View Scheme

: 18643-50-0
1-pentynyl lithium

: 28079-04-1
(Z)-8-dodecen-1-yl acetate

Conditions

Yield

Multi-step reaction with 4 steps
1: 89 percent / NH2 / tetrahydrofuran; dimethylsulfoxide
2: 1) 9-BBN, 2) H2O2, AcONa
3: 85 percent / H2 / Ni-P2
4: 89 percent / pyridine
View Scheme

Multi-step reaction with 6 steps
1: 69 percent / Fe acetylacetonate / diethyl ether; liquid ammonia / from -30 to 20 deg C, 15 h
2: 95 percent / pyridine / -5 - 0 °C
3: 90 percent / LiBr / acetone / 6 h / Heating
4: 78 percent / CuI, bi-2-pyridyl / tetrahydrofuran / 2 h / 2 °C
5: 1) 9-borabicyclo<3.3.1>nonane, 2) CH3CO2H / 1) THF, 0 deg C, 24 h, 2) reflux, 9 h
6: pyridine / 15 h / 20 °C
View Scheme

: 197901-17-0
Dodec-1-en-8-yne

: 28079-04-1
(Z)-8-dodecen-1-yl acetate

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 1) 9-BBN, 2) H2O2, AcONa 2: 85 percent / H2 / Ni-P2 3: 89 percent / pyridine View Scheme

: 68750-25-4
6-acetoxy-1-hexanal

: 28079-04-1
(Z)-8-dodecen-1-yl acetate

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 1.) BuSnCl3 / 1.) CHCl3, 0 deg C, 2 min, 2.) CHCl3, 0 deg C, 30 min 2: DMPA / CH2Cl2 3: 58 percent / NaBH4 / dimethylsulfoxide / 80 °C View Scheme

: 74940-39-9
hex-2-enyl-tributylstannane

: 28079-04-1
(Z)-8-dodecen-1-yl acetate

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 1.) BuSnCl3 / 1.) CHCl3, 0 deg C, 2 min, 2.) CHCl3, 0 deg C, 30 min 2: DMPA / CH2Cl2 3: 58 percent / NaBH4 / dimethylsulfoxide / 80 °C View Scheme

: 156360-24-6
Acetic acid (Z)-6-hydroxy-dodec-8-enyl ester

: 28079-04-1
(Z)-8-dodecen-1-yl acetate

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: DMPA / CH2Cl2 2: 58 percent / NaBH4 / dimethylsulfoxide / 80 °C View Scheme

: 53963-10-3
2-[(6-bromohexyl)oxy]tetrahydro-2H-pyran

: 28079-04-1
(Z)-8-dodecen-1-yl acetate

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: KO-tBu, n-BuLi / hexane; diethyl ether / -78 deg C up to RT for 17 h 2: 1.) ICl; 2.) aq. KF / 1.) CCl4, 15 min; 2.) DMSO, RT, 4 h 3: 88 percent / (Ph3P)4Pd / tetrahydrofuran / Ambient temperature 4: 77 percent / HOAc / 6 h / 60 °C View Scheme

: 98369-16-5
(Z)-9-iodo-1-(2-tetrahydropyranyloxy)non-8-ene

: 28079-04-1
(Z)-8-dodecen-1-yl acetate

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 88 percent / (Ph3P)4Pd / tetrahydrofuran / Ambient temperature 2: 77 percent / HOAc / 6 h / 60 °C View Scheme

: 98369-07-4
9-trimethylsilyl-1-(2-tetrahydropyranyloxy)-8-(E)-nonene

: 28079-04-1
(Z)-8-dodecen-1-yl acetate

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 1.) ICl; 2.) aq. KF / 1.) CCl4, 15 min; 2.) DMSO, RT, 4 h 2: 88 percent / (Ph3P)4Pd / tetrahydrofuran / Ambient temperature 3: 77 percent / HOAc / 6 h / 60 °C View Scheme

: 67-56-1
methanol

: 28079-04-1
(Z)-8-dodecen-1-yl acetate

A: Acetic acid 8-methoxy-dodecyl ester

B: Acetic acid 9-methoxy-dodecyl ester

Conditions

Conditions	Yield
With sodium tetrahydroborate; mercury(II) diacetate 1.) 48 h, RT; 2.) glacial acetic acid; Multistep reaction;

...Expand

: 624-92-0
Dimethyldisulphide

: 28079-04-1
(Z)-8-dodecen-1-yl acetate

: 84801-35-4
Acetic acid 8,9-bis-methylsulfanyl-dodecyl ester

Conditions

Conditions	Yield
With iodine In diethyl ether; hexane at 40℃;

(Z)-Dodec-8-enyl acetate Specification

The Orfralure, with the CAS registry number 28079-04-1, is also known as (Z)-8-Dodecen-1-ol acetate. Its EINECS number is 248-823-6. This chemical's molecular formula is C₁₄H₂₆O₂ and formula weight is 226.36. What's more, its IUPAC name is [(Z)-dodec-8-enyl] acetate.

Physical properties of Orfralure are: (1)ACD/LogP: 5.50; (2)# of Rule of 5 Violations: 1 ; (3)#H bond acceptors: 2; (4)#H bond donors: 0; (5)#Freely Rotating Bonds: 11; (6)Polar Surface Area: 26.3 Å²; (7)Index of Refraction: 1.448; (8)Molar Refractivity: 68.74 cm³; (9)Molar Volume: 256.7 cm³; (10)Surface Tension: 30 dyne/cm; (11)Density: 0.881 g/cm³; (12)Flash Point: 96.5 °C; (13)Enthalpy of Vaporization: 54.02 kJ/mol; (14)Boiling Point: 300.1 °C at 760 mmHg; (15)Vapour Pressure: 0.00114 mmHg at 25°C.

Preparation: this chemical can be prepared by 1-Acetoxydodec-8-yne. This reaction will need reagent H₂, quinoline and solvent methanol. This reaction will also need catalyst 5% Pd/BaSO₄. The yield is about 97%.

You can still convert the following datas into molecular structure:
(1)Canonical SMILES: CCCC=CCCCCCCCOC(=O)C
(2)Isomeric SMILES: CCC/C=C\CCCCCCCOC(=O)C
(3)InChI: InChI=1S/C14H26O2/c1-3-4-5-6-7-8-9-10-11-12-13-16-14(2)15/h5-6H,3-4,7-13H2,1-2H3/b6-5-
(4)InChIKey: SUCYDSJQVVGOIW-WAYWQWQTSA-N

Product Name

(Z)-8-DODECEN-1-YL ACETATE

Synthetic route

(Z)-Dodec-8-enyl acetate Specification

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