28079-04-1

Basic information

• Product Name: (Z)-8-DODECEN-1-YL ACETATE
• Synonyms: (8Z)-8-Dodecenyl acetate;(Z)-8-Dodecen-1-ol acetate;8-Dodecen-1-ol, acetate, (Z)-;acetate,(z)-8-dodecen-1-o;z-8-dodecenyl;z-8-dodecenylacetate;(Z)-8-DODECEN-1-YL ACETATE;CIS-8-DODECEN-1-OL ACETATE
• CAS NO: 28079-04-1
• Molecular Formula: C₁₄H₂₆O₂
• Molecular Weight: 226.36
• EINECS: 248-823-6
• Product Categories: insect pheromone
• Mol File: 28079-04-1.mol
• Article Data: 24

Chemical Properties

• Boiling Point: 300.1 °C at 760 mmHg
• Flash Point: 96.5 °C
• Appearance: /
• Density: 0.881
• Vapor Pressure: 0.00114mmHg at 25°C
• Refractive Index: 1.448
• Storage Temp.: 2-8°C
• Solubility: DMSO (Slightly), Water (Slightly)
• Stability: Very Hygroscopic
• CAS DataBase Reference: (Z)-8-DODECEN-1-YL ACETATE(CAS DataBase Reference)
• NIST Chemistry Reference: (Z)-8-DODECEN-1-YL ACETATE(28079-04-1)
• EPA Substance Registry System: (Z)-8-DODECEN-1-YL ACETATE(28079-04-1)

Safety Data

• Hazardous Substances Data: 28079-04-1(Hazardous Substances Data)

Usage

Chemical Properties

White to Pale Yellow Solid

Uses

Different sources of media describe the Uses of 28079-04-1 differently. You can refer to the following data:
1. Inhibits protein synthesis by binding to L6 protein of 50S ribosomal subunit. Antibacterial. Antibiotic complex consists of three closely related components, gentamicins C1, C2, C1a, and also gentamic in A which differs from the other members of the complex but is similar to Kanamycin C. Gentamicin C1: R1=R2=CH3 Gentamicin C2: R1=CH3; R2=H Gentamicin C1A: R1=R2=H
2. (8Z)-Dodecenyl Acetate is derived from 1-Pentyne (P284800), which is used as a reagent in the synthesis of novel 1,2,3-triazole-1,4-benzoxazine hybrids which exhibit antiproliferative activity. 1-Pentyne is also used as a reagent in the synthesis of disubstituted isoxazoles which exhibit anti-aging activity.

Synthesis Reference(s)

Tetrahedron Letters, 14, p. 675, 1973 DOI: 10.1016/S0040-4039(00)72431-2

InChI:InChI=1/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-

Synthetic route

1-Acetoxydodec-8-yne (26906-26-3) → (Z)-8-dodecen-1-yl acetate (28079-04-1)

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

(Z)-8-dodecenol (40642-40-8) + acetyl chloride (75-36-5) → (Z)-8-dodecen-1-yl acetate (28079-04-1)

Conditions	Yield
In pyridine	95%
With pyridine In benzene

Δ8-dodecen-1-ol (153123-34-3) + acetic anhydride (108-24-7) → (Z)-8-dodecen-1-yl acetate (28079-04-1)

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

(Z)-8-dodecenol (40642-40-8) + acetic anhydride (108-24-7) → (Z)-8-dodecen-1-yl acetate (28079-04-1)

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%

(Z)-1-(2-tetrahydropyranyloxy)dodec-8-ene (98398-50-6) + acetyl chloride (75-36-5) → (Z)-8-dodecen-1-yl acetate (28079-04-1)

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

1-penten (109-67-1) + non-8-en-1-yl acetate (13038-22-7) → (Z)-8-dodecen-1-yl acetate (28079-04-1)

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

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

(E)-8-dodecenyl acetate (38363-29-0) → (Z)-8-dodecen-1-yl acetate (28079-04-1)

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

Δ8-dodecen-1-ol (153123-34-3) + acetic anhydride (108-24-7) → (Z)-8-dodecen-1-yl acetate (28079-04-1) + (E)-8-dodecenyl acetate (38363-29-0)

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

acetic anhydride (108-24-7) + (Z)-1-(2-tetrahydropyranyloxy)dodec-8-ene (98398-50-6) → (Z)-8-dodecen-1-yl acetate (28079-04-1)

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

n-butyl(triphenyl)phosphonium bromide (1779-51-7) → (Z)-8-dodecen-1-yl acetate (28079-04-1) + (E)-8-dodecenyl acetate (38363-29-0)

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.;

1-Pentyne (627-19-0) → (Z)-8-dodecen-1-yl acetate (28079-04-1)

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

(Z)-oct-4-enal (39924-26-0) → (Z)-8-dodecen-1-yl acetate (28079-04-1)

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

7-chloroheptanoic acid (821-57-8) → (Z)-8-dodecen-1-yl acetate (28079-04-1)

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

(Z)-4-octene-1-ol (54393-36-1) → (Z)-8-dodecen-1-yl acetate (28079-04-1)

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

8-Dodecyn-1-ol (41589-71-3) → (Z)-8-dodecen-1-yl acetate (28079-04-1)

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

8-Dodecinsaeure (18545-07-8) → (Z)-8-dodecen-1-yl acetate (28079-04-1)

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

1,1-dimethoxy-8-tosyloxy-(4Z)-octene (82861-01-6) → (Z)-8-dodecen-1-yl acetate (28079-04-1)

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

1,1-dimethoxy-4Z-octene (119265-28-0) → (Z)-8-dodecen-1-yl acetate (28079-04-1)

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

(Z)-1-bromo-4-octene (79837-81-3) → (Z)-8-dodecen-1-yl acetate (28079-04-1)

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

7-bromo-hept-1-ene (4117-09-3) → (Z)-8-dodecen-1-yl acetate (28079-04-1)

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

1-pentynyl lithium (18643-50-0) → (Z)-8-dodecen-1-yl acetate (28079-04-1)

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

Dodec-1-en-8-yne (197901-17-0) → (Z)-8-dodecen-1-yl acetate (28079-04-1)

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

6-acetoxy-1-hexanal (68750-25-4) → (Z)-8-dodecen-1-yl acetate (28079-04-1)

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

hex-2-enyl-tributylstannane (74940-39-9) → (Z)-8-dodecen-1-yl acetate (28079-04-1)

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

Acetic acid (Z)-6-hydroxy-dodec-8-enyl ester (156360-24-6) → (Z)-8-dodecen-1-yl acetate (28079-04-1)

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

2-[(6-bromohexyl)oxy]tetrahydro-2H-pyran (53963-10-3) → (Z)-8-dodecen-1-yl acetate (28079-04-1)

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

(Z)-9-iodo-1-(2-tetrahydropyranyloxy)non-8-ene (98369-16-5) → (Z)-8-dodecen-1-yl acetate (28079-04-1)

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

9-trimethylsilyl-1-(2-tetrahydropyranyloxy)-8-(E)-nonene (98369-07-4) → (Z)-8-dodecen-1-yl acetate (28079-04-1)

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

methanol (67-56-1) + (Z)-8-dodecen-1-yl acetate (28079-04-1) → Acetic acid 8-methoxy-dodecyl ester + Acetic acid 9-methoxy-dodecyl ester

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

Dimethyldisulphide (624-92-0) + (Z)-8-dodecen-1-yl acetate (28079-04-1) → Acetic acid 8,9-bis-methylsulfanyl-dodecyl ester (84801-35-4)

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

Upstream product

• 38363-29-0 (E)-8-dodecenyl acetate 
• 817210-79-0 Z/E-8-dodecenyl bromide 
• 127-09-3 sodium acetate 
• 50816-19-8 8-bromooctanol 
• 98369-07-4 9-trimethylsilyl-1-(2-tetrahydropyranyloxy)-8-(E)-nonene 
• 98369-16-5 (Z)-9-iodo-1-(2-tetrahydropyranyloxy)non-8-ene 
• 156360-24-6 Acetic acid (Z)-6-hydroxy-dodec-8-enyl ester 
• 74940-39-9 hex-2-enyl-tributylstannane 
• 68750-25-4 6-acetoxy-1-hexanal 
• 18643-50-0 1-pentynyl lithium 
• 4117-09-3 7-bromo-hept-1-ene 
• 119265-28-0 1,1-dimethoxy-4Z-octene 
• 82861-01-6 1,1-dimethoxy-8-tosyloxy-(4Z)-octene 
• 18545-07-8 8-Dodecinsaeure 

Relevant articles and documents

PHEROMONES OF INSECTS AND THEIR ANALOGS. XXI. SYNTHESIS OF ALK-8Z-EN-1-OLS AND THEIR ACETATES FROM A FUNCTIONALLY DIFFERENTIATED PRODUCT OF OZONOLYSIS OF CYCLOOCTENE

Dodec-8Z-en-1-ol (VIII) and tetradec-8Z-en-1-ol (IX) and the corresponding acetates (X and IX) - components of the sex pheromones of many species of Lepidoptera - have been synthesized from cyclooctene (I) in three stages.The ozonolysis of (I) ( -70 deg C, CH2Cl2-MeOH), NaHCO3; -20 deg C, Ac2O/Et3N) led to methyl 8-oxooctanoate (II).The DNPH of (II), (III), mp 59-61 deg C.The coupling of (II) with n-C3H17CH=PPh3 (IV) or with n-C5H11CH=PPh3 (V) (-70 deg C , 2h; 25 deg C, 15h, Ar) gave the methyl esters of dodec-8Z-enoic (VI) and tetradec-8Z-enoic (VII) acids, respectively.The reduction of (VI) and (VII) gave the corresponding alcohols (VIII) and (IX) by the acetylation (Ac2O-Py, 25 deg C, 24h) of which, (X) and (XI) , were obtained.The yields (percent): (II) 80, (VI) 45, (VII) 60, (VIII) 95, (IX) 90, (X) 75, (XI) 74.The IR and PMR spectra of compounds (II) and (VI-XI) are given.

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SYNTHESIS OF STRAIGHT-CHAIN LEPIDOPTERAN PHEROMONES THROUGH ONE- OR TWO- CARBON HOMOLOGATION OF FATTY ALKENES

Methods for the preparation of alkenes including insect pheromones are described. The methods include homologation reactions employing reagents such as 1,3-diesters, epoxides, cyanoacetates, and cyanide salts for elongation of starting materials and intermediates by one or two carbon atoms. The alkenes include insect pheromones useful in a number of agricultural applications.

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