34010-21-4

Basic information

• Product Name: (Z)-11-HEXADECEN-1-YL ACETATE
• Synonyms: (Z)-11-HEXADECEN-1-YL ACETATE;(11Z)-11-Hexadecenyl acetate;(z)-11-hexadecenylacetate;(z)-13-octadecenyl;(z)-13-octadecenylacetate;11-Hexadecen-1-ol, acetate, (Z)-;acetate,(z)-11-hexadecen-1-o;cis-11-hexadecen-1-ylacetate
• CAS NO: 34010-21-4
• Molecular Formula: C₁₈H₃₄O₂
• Molecular Weight: 282.46
• EINECS: 251-791-6
• Product Categories: insect pheromone
• Mol File: 34010-21-4.mol
• Article Data: 28

Chemical Properties

• Boiling Point: 348.7±11.0℃ (760 Torr)
• Flash Point: 88.3±17.6℃
• Appearance: /
• Density: 0.875±0.06 g/cm3 (20 ºC 760 Torr)
• Vapor Pressure: 4.93E-05mmHg at 25°C
• Refractive Index: 1.4532 (20℃)
• Storage Temp.: -20°C
• Solubility: Chloroform (Slightly), DMSO (Slightly), Ethyl Acetate (Slightly)
• CAS DataBase Reference: (Z)-11-HEXADECEN-1-YL ACETATE(CAS DataBase Reference)
• NIST Chemistry Reference: (Z)-11-HEXADECEN-1-YL ACETATE(34010-21-4)
• EPA Substance Registry System: (Z)-11-HEXADECEN-1-YL ACETATE(34010-21-4)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 34010-21-4(Hazardous Substances Data)

Usage

Uses

(Z)-11-Hexadecen-1-ol Acetate can be used to synthesize sex attractant compounds for insects such as Plutella Xylostella.

InChI:InChI=1/C18H34O2/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-20-18(2)19/h6-7H,3-5,8-17H2,1-2H3/b7-6-

Synthetic route

(Z)-11-hexadecen-1-ol (56683-54-6) + acetyl chloride (75-36-5) → (Z)-11-hexadecen-1-yl acetate (34010-21-4)

Conditions	Yield
With pyridine In benzene for 4h; Heating;	98.5%

(Z)-11-hexadecen-1-ol (56683-54-6) + acetic anhydride (108-24-7) → (Z)-11-hexadecen-1-yl acetate (34010-21-4)

Conditions	Yield
With pyridine for 12h; Ambient temperature;	98%
With pyridine at 0℃; for 3h;	97%
With triethylamine In dichloromethane at 20℃; for 8h; Inert atmosphere; Schlenk technique; Cooling with ice;	94%

(Z)-11-hexadecenal (53939-28-9) + acetic anhydride (108-24-7) → (Z)-11-hexadecen-1-yl acetate (34010-21-4)

Conditions	Yield
With pyridine In dichloromethane at 20℃;	90%

(Z)-2-(hexadec-11-en-1-yloxy)tetrahydro-2H-pyran (99159-89-4) + acetyl chloride (75-36-5) → (Z)-11-hexadecen-1-yl acetate (34010-21-4)

Conditions	Yield
In acetic acid at 35 - 40℃;	68%
In hexane; acetic acid

1-acetoxy-7-bromoheptane (21727-91-3) + (Z)-4-nonenyl bromide (59499-29-5) → (Z)-11-hexadecen-1-yl acetate (34010-21-4)

Conditions	Yield
(i) Mg, (ii) /BRN= 1760288/; Multistep reaction;

(11Z)-hexadeca-1,11-diene (65734-21-6, 82294-54-0) → (Z)-11-hexadecen-1-yl acetate (34010-21-4)

Conditions	Yield
Yield given. Multistep reaction;
Multi-step reaction with 2 steps 1: 1. 9-BBN, 2. 3N NaOH, 26percent H2O2 / 1. THF, r.t., 5 h, 2. r.t., 17 h 2: 98 percent / pyridine / 12 h / Ambient temperature View Scheme
Multi-step reaction with 2 steps 1: 9-BBN / tetrahydrofuran 2: Py / 3 h / Heating View Scheme

Hexadec-11-ynyl acetate (53596-80-8) → (Z)-11-hexadecen-1-yl acetate (34010-21-4)

Conditions	Yield
With methanol; 9-borabicyclo[3.3.1]nonane dimer; acetic acid 1.) THF, 0 deg C, 48 h, 2.) 25 deg C, 1 h; Yield given. Multistep reaction;
With hydrogen; P-2 Ni Yield given;

n-butyl magnesium bromide (693-03-8) + acetic anhydride (108-24-7) + (Z)-2-(8-phenylthiododec-11-enyloxy)tetrahydro-2H-pyran (98752-56-8) → (Z)-11-hexadecen-1-yl acetate (34010-21-4) + (E)-11-hexadecen-1-yl acetate (56218-72-5)

Conditions	Yield
1,2-bis(diphenylphosphino)ethane nickel(II) chloride 1.) ether, 12 h, room temp., 2.) 80 deg C, 15 h; Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts;

11-hexadecene-1-ol (113789-13-2) + acetic anhydride (108-24-7) → (Z)-11-hexadecen-1-yl acetate (34010-21-4) + (E)-11-hexadecen-1-yl acetate (56218-72-5)

Conditions	Yield
With pyridine Yield given. Yields of byproduct given. Title compound not separated from byproducts;

11-hexadecyn-1-ol (65686-49-9) → (Z)-11-hexadecen-1-yl acetate (34010-21-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: H2 / Pd/BaSO4 2: pyridine View Scheme
Multi-step reaction with 2 steps 1: 92 percent / i-BuMgBr, Cp2TiCl2 2: 90 percent / pyridine View Scheme
Multi-step reaction with 2 steps 1: 1.) isobutylmagnesium bromide; 2.) C5H5TiCl2 / 1.) diethyl ether, 0 deg C, 15 min; 2.) room temp., 1-1,5 h 2: 90 percent / pyridine View Scheme

1-hexynyllithium (17689-03-1) → (Z)-11-hexadecen-1-yl acetate (34010-21-4)

Conditions	Yield
Multi-step reaction with 4 steps 1: HMPA / tetrahydrofuran 2: p-toluenesulfonic acid / methanol 3: H2 / Pd/BaSO4 4: pyridine View Scheme
Multi-step reaction with 4 steps 1: 85 percent 2: 1) O3, 2) NaBH4 / 1) cyclohexane, MeOH 3: 92 percent / i-BuMgBr, Cp2TiCl2 4: 90 percent / pyridine View Scheme

1-bromo-10-(tetrahydropyranyloxy)decane (51795-88-1) → (Z)-11-hexadecen-1-yl acetate (34010-21-4)

Conditions	Yield
Multi-step reaction with 4 steps 1: HMPA / tetrahydrofuran 2: p-toluenesulfonic acid / methanol 3: H2 / Pd/BaSO4 4: pyridine View Scheme
Multi-step reaction with 4 steps 1.1: n-butyllithium / hexane; tetrahydrofuran / 1 h / -78 - 20 °C / Inert atmosphere 1.2: 16 h / Inert atmosphere; Reflux 2.1: potassium hydroxide; N,N-dimethyl-formamide / 6 h / 145 °C / Inert atmosphere; Sealed tube 3.1: toluene-4-sulfonic acid / methanol / 16 h / 20 °C 4.1: pyridine / 26 h / 0 - 20 °C View Scheme

2-(hexadec-11-yn-1-yloxy)tetrahydro-2H-pyran (73784-65-3) → (Z)-11-hexadecen-1-yl acetate (34010-21-4)

Conditions	Yield
Multi-step reaction with 3 steps 1: p-toluenesulfonic acid / methanol 2: H2 / Pd/BaSO4 3: pyridine View Scheme
Multi-step reaction with 3 steps 1: potassium hydroxide; N,N-dimethyl-formamide / 6 h / 145 °C / Inert atmosphere; Sealed tube 2: toluene-4-sulfonic acid / methanol / 16 h / 20 °C 3: pyridine / 26 h / 0 - 20 °C View Scheme

1-undecen-11-ylbromide (7766-50-9) → (Z)-11-hexadecen-1-yl acetate (34010-21-4)

Conditions	Yield
Multi-step reaction with 4 steps 1: 85 percent 2: 1) O3, 2) NaBH4 / 1) cyclohexane, MeOH 3: 92 percent / i-BuMgBr, Cp2TiCl2 4: 90 percent / pyridine View Scheme

heptadec-1-en-12-yne (114971-83-4) → (Z)-11-hexadecen-1-yl acetate (34010-21-4)

Conditions	Yield
Multi-step reaction with 3 steps 1: 1) O3, 2) NaBH4 / 1) cyclohexane, MeOH 2: 92 percent / i-BuMgBr, Cp2TiCl2 3: 90 percent / pyridine View Scheme
Multi-step reaction with 3 steps 1: 1.) 2percent O3 in O2; 2.) sodium tetrahydroborate / 1.) cyclohexane, methanol; 2.) room temp., 15 h 2: 1.) isobutylmagnesium bromide; 2.) C5H5TiCl2 / 1.) diethyl ether, 0 deg C, 15 min; 2.) room temp., 1-1,5 h 3: 90 percent / pyridine View Scheme

1-Bromo-11-hydroxyundecane (1611-56-9) → (Z)-11-hexadecen-1-yl acetate (34010-21-4)

Conditions	Yield
Multi-step reaction with 3 steps 1: 90 percent / acetonitrile 2: 63 percent / DMSO, NaH / tetrahydrofuran / 0.5 h 3: pyridine View Scheme
Multi-step reaction with 3 steps 1.1: acetonitrile / 48 h / Inert atmosphere; Reflux 2.1: sodium hexamethyldisilazane / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere; Schlenk technique 2.2: 24 h / 20 °C 3.1: triethylamine / dichloromethane / 8 h / 20 °C / Inert atmosphere; Schlenk technique; Cooling with ice View Scheme

(11‑hydroxyundecyl)triphenylphosphonium bromide (19101-00-9) → (Z)-11-hexadecen-1-yl acetate (34010-21-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: 63 percent / DMSO, NaH / tetrahydrofuran / 0.5 h 2: pyridine View Scheme

hexadec-11-ynal (86426-73-5) → (Z)-11-hexadecen-1-yl acetate (34010-21-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: 1.) 9-borabicyclo<3.3.1>nonane, 2.) glacial acetic acid / 1.) THF, 0-5 deg C, 24 h, 2.) reflux, 9 h 2: 86 percent / pyridine / 15 h / 20 °C View Scheme

pentanal (110-62-3) + C6-dials → (Z)-11-hexadecen-1-yl acetate (34010-21-4)

Conditions	Yield
Multi-step reaction with 8 steps 1: 1.) Na2SO3, NaHCO3 / 1.) H2O, 10 h, 2.) 1 h 2: Et3N / CH2Cl2 / 1 h / Ambient temperature 3: 1.) Mg / 1.) Et2O, 2.) reflux, 1 h 4: (AcO)2Cu / acetic acid; H2O / 0.67 h / Heating 5: 85percent hydrazine hydrate / butan-1-ol / Heating 6: O2, CuCl / pyridine 7: acetic acid / 10 h / 50 °C 8: H2 / P-2 Ni View Scheme

2-hydroxyhexanenitrile (64350-07-8) → (Z)-11-hexadecen-1-yl acetate (34010-21-4)

Conditions	Yield
Multi-step reaction with 7 steps 1: Et3N / CH2Cl2 / 1 h / Ambient temperature 2: 1.) Mg / 1.) Et2O, 2.) reflux, 1 h 3: (AcO)2Cu / acetic acid; H2O / 0.67 h / Heating 4: 85percent hydrazine hydrate / butan-1-ol / Heating 5: O2, CuCl / pyridine 6: acetic acid / 10 h / 50 °C 7: H2 / P-2 Ni View Scheme

(Z)-4-nonen-1-ol (59499-28-4) → (Z)-11-hexadecen-1-yl acetate (34010-21-4)

Conditions	Yield
Multi-step reaction with 3 steps 1: 95 percent / 6.5 h / -5 - 0 °C View Scheme
Multi-step reaction with 2 steps 1: PBr3 / benzene 2: (i) Mg, (ii) /BRN= 1760288/ View Scheme
Multi-step reaction with 4 steps 1: pyridine 2: dilithium tetrachlorocuprate; magnesium / tetrahydrofuran 3: pyridinium p-toluenesulfonate / ethanol / 80 °C 4: pyridine / 3 h / 0 °C View Scheme

2-Trimethylsilyloxy-n-capronitril (106942-21-6) → (Z)-11-hexadecen-1-yl acetate (34010-21-4)

Conditions	Yield
Multi-step reaction with 6 steps 1: 1.) Mg / 1.) Et2O, 2.) reflux, 1 h 2: (AcO)2Cu / acetic acid; H2O / 0.67 h / Heating 3: 85percent hydrazine hydrate / butan-1-ol / Heating 4: O2, CuCl / pyridine 5: acetic acid / 10 h / 50 °C 6: H2 / P-2 Ni View Scheme

1-tert-Butoxy-hexadec-11-in (87292-04-4) → (Z)-11-hexadecen-1-yl acetate (34010-21-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: acetic acid / 10 h / 50 °C 2: H2 / P-2 Ni View Scheme

(Z)-4-Nonenyl acetate (Z)-3-Nonenyl acetate (Z)-3-Nonenyl acetate (Z)-3-Nonenyl acetate (Z)-3-nonenyl acetate (83165-97-3) → (Z)-11-hexadecen-1-yl acetate (34010-21-4)

Conditions	Yield
Multi-step reaction with 4 steps 1: 54 percent / KOH / H2O; methanol / 24 h / Ambient temperature 2: 95 percent / 6.5 h / -5 - 0 °C View Scheme

16-tert-Butoxy-hexadecane-5,6-dione (112983-51-4) → (Z)-11-hexadecen-1-yl acetate (34010-21-4)

Conditions	Yield
Multi-step reaction with 4 steps 1: 85percent hydrazine hydrate / butan-1-ol / Heating 2: O2, CuCl / pyridine 3: acetic acid / 10 h / 50 °C 4: H2 / P-2 Ni View Scheme

1-tert-Butoxy-12-hydroxyhexadecan-11-on (112983-46-7) → (Z)-11-hexadecen-1-yl acetate (34010-21-4)

Conditions	Yield
Multi-step reaction with 5 steps 1: (AcO)2Cu / acetic acid; H2O / 0.67 h / Heating 2: 85percent hydrazine hydrate / butan-1-ol / Heating 3: O2, CuCl / pyridine 4: acetic acid / 10 h / 50 °C 5: H2 / P-2 Ni View Scheme

C20H42N4O (112983-58-1) → (Z)-11-hexadecen-1-yl acetate (34010-21-4)

Conditions	Yield
Multi-step reaction with 3 steps 1: O2, CuCl / pyridine 2: acetic acid / 10 h / 50 °C 3: H2 / P-2 Ni View Scheme

1-tosyloxynon-4Z-ene (83165-98-4) → (Z)-11-hexadecen-1-yl acetate (34010-21-4)

9-Decen-1-ol (13019-22-2) → (Z)-11-hexadecen-1-yl acetate (34010-21-4)

Conditions	Yield
Multi-step reaction with 3 steps 1: pyridine / Ambient temperature 3: 1.) 9-borabicyclo<3.3.1>nonane (9-BBN), 2.) methanol, glacial acetic acid / 1.) THF, 0 deg C, 48 h, 2.) 25 deg C, 1 h View Scheme

(Z)-11-hexadecen-1-yl acetate (34010-21-4) → (Z)-11-hexadecen-1-ol (56683-54-6)

Conditions	Yield
With sodium hydroxide In ethanol for 1h; Heating;	97%
Hydrolysis;
With Tris-HCl buffer; antennal esterase from Sesamia nonagrioides In ethanol at 32℃; for 1h; pH=8.0; Enzyme kinetics;

methanol (67-56-1) + (Z)-11-hexadecen-1-yl acetate (34010-21-4) → Acetic acid 11-methoxy-hexadecyl ester + Acetic acid 12-methoxy-hexadecyl ester

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

Dimethyldisulphide (624-92-0) + (Z)-11-hexadecen-1-yl acetate (34010-21-4) → Acetic acid 11,12-bis-methylsulfanyl-hexadecyl ester (84801-59-2)

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

(Z)-11-hexadecen-1-yl acetate (34010-21-4) → 11-Oxoundecyl acetate (57584-82-4)

Conditions	Yield
With ozonolysis

(Z)-11-hexadecen-1-yl acetate (34010-21-4) → Acetic acid 10-(3-butyl-oxiranyl)-decyl ester

Conditions	Yield
With 3-chloro-benzenecarboperoxoic acid

(Z)-11-hexadecen-1-yl acetate (34010-21-4) → (Z)-11-hexadecenal (53939-28-9)

Conditions	Yield
With pyridine; chromium(VI) oxide In dichloromethane Oxidation;

(Z)-11-hexadecen-1-yl acetate (34010-21-4) → (Z)-11-Hexadecenyl bromide (80763-04-8)

Conditions	Yield
1: Hydrolysis / 2: Bromination;

(Z)-11-hexadecen-1-yl acetate (34010-21-4) → (5Z,27Z)-5,27-tritriacontadiene

Conditions	Yield
Multi-step reaction with 3 steps 3.1: Mg / tetrahydrofuran 3.2: Li2CuCl4 / tetrahydrofuran View Scheme

Upstream product

• 65734-21-6 (11Z)-hexadeca-1,11-diene 
• 693-03-8 n-butyl magnesium bromide 
• 108-24-7 acetic anhydride 
• 98752-56-8 (Z)-2-(8-phenylthiododec-11-enyloxy)tetrahydro-2H-pyran 
• 113789-13-2 11-hexadecene-1-ol 
• 65686-49-9 11-hexadecyn-1-ol 
• 17689-03-1 1-hexynyllithium 
• 51795-88-1 1-bromo-10-(tetrahydropyranyloxy)decane 
• 111-81-9 Methyl 10-undecenoate 
• 6287-90-7 11-bromo-undecanoic acid methyl ester 
• 24724-07-0 methyl 11-hydroxyundecanoate 
• 2416-20-8 (11Z)-hexadec-11-enoic acid 
• 3710-30-3 1,7-Octadiene 
• 56683-54-6 (Z)-11-hexadecen-1-ol 

Downstream Products

• 56683-54-6 (Z)-11-hexadecen-1-ol 
• 53939-28-9 (Z)-11-hexadecenal 
• 20711-10-8 (Z)-11-tetradecenyl acetate 
• 33189-72-9 (E)-tetradec-11-en-1-yl acetate 

Relevant articles and documents

Inhibition of pheromone action in Sesamia nonagrioides by haloacetate analogues

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INSECT PHEROMONES AND THEIR ANALOGUES XXVI. SYNTHESIS OF HEXADEC-11Z-EN-1-OL AND ITS ACETATE AND HEXADEC-11Z-EN-AL -COMPONENTS OF THE PHEROMONES OF INSECTS OF THE ORDER LEPIDOPTERA

Pheromone components of insects of the genera Heliothis and Mamestra have been synthesized with the use of functionally differentiated ozonolysis of cyclododecene.

Method for synthesizing grassland spodoptera litura sex pheromone active ingredients

The invention belongs to the technical field of green pesticide synthesis, and discloses a novel method for synthesizing grassland spodoptera litura sex pheromone active ingredients (Z)-9-dodecene-1-alcohol acetate, (Z)-9-tetradecene-1-alcohol acetate and (Z)-11-hexadecene-1-alcohol acetate. The method comprises the steps: using bromo-alcohol as a starting raw material; and firstly generating hydroxyl phosphonium salt with triphenylphosphine, then respectively carrying out Wittig coupling reaction with propionaldehyde and valeraldehyde to generate Z-type enol, and finally carrying out acetylation reaction with acetic anhydride to prepare (Z)-9-dodecene-1-alcohol acetate, (Z)-9-tetradecene-1-alcohol acetate and (Z)-11-hexadecene-1-alcohol acetate. According to the method, hydroxyl phosphonium salt is used for Wittig reaction, two steps of hydroxyl protection and deprotection are omitted, the synthetic route is simplified, and the method has the advantages of being environmentally friendly and the like.

A moth pheromone synthesis method of pickles (by machine translation)

The invention belongs to the technical field of chemical synthesis, in particular relates to a moth pheromone of the pickles synthetic method, comprises the following steps: 1) in the organic solvent, 11 - bromo - 1 - [...] with triphenylphosphine reaction to produce bromo Hendecane [...]; 2) under the protection of nitrogen, step 1) obtained in the bromo Hendecane [...] with valeraldehyde, sodium ethoxide in tetrahydrofuran solvent to react to generate cis - 11 - sixteen-carbon vinyl alcohol; 3) in the dichloromethane solution in, step 2) obtained in the cis - 11 - sixteen carbon alcohol with the occurrence chloro-chromic acid pyridine salt to the oxidizing reaction to produce cis - 11 - sixteen [...]; 4) in dichloromethane in, step 2) obtained in the cis - 11 - sixteen carbon alcohol with acetic anhydride, pyridine reaction to produce cis - 11 - sixteen-carbon vinyl alcohol acetate. The invention uses inexpensive and easily obtained 11 - bromo - 1 - [...] as the starting material, the synthesis step is reduced, simplifies the synthesis process, the product yield is high, the reaction conditions are mild and controllable, low requirements on equipment, can be used for industrial production. (by machine translation)