30507-70-1

Basic information

• Product Name: (Z,E)-9,12-TETRADECADIENYLACETATE
• Synonyms: CIS-9, TRANS-12-TETRADECENIAL-1-OL ACETATE;(2E,5Z)-14-Acetoxy-2,5-tetradecadiene;(9Z,12E)-9,12-Tetradecadien-1-ol acetate;Acetic acid (9Z,12E)-9,12-tetradecadienyl ester;Acetic acid [(9Z,12E)-9,12-tetradecadienyl] ester;Litlure B;trans,cis-9,12-Tetradecadienyl acetate;9,12-Tetradecadien-1-ol, 1-acetate, (9Z,12E)-
• CAS NO: 30507-70-1
• Molecular Formula: C₁₆H₂₈O₂
• Molecular Weight: 252.44
• Mol File: 30507-70-1.mol

Chemical Properties

• Boiling Point: 334.8±21.0℃ (760 Torr)
• Flash Point: 102.3±20.4℃
• Appearance: /
• Density: 0.890±0.06 g/cm3 (20 ºC 760 Torr)
• Refractive Index: 1.4565 (25℃)
• CAS DataBase Reference: (Z,E)-9,12-TETRADECADIENYLACETATE(CAS DataBase Reference)
• NIST Chemistry Reference: (Z,E)-9,12-TETRADECADIENYLACETATE(30507-70-1)
• EPA Substance Registry System: (Z,E)-9,12-TETRADECADIENYLACETATE(30507-70-1)

Safety Data

• Safety Statements: Moderately toxic by ingestion. When heated to decomposition it emits acrid smoke and irritating vapors.:
• Hazardous Substances Data: 30507-70-1(Hazardous Substances Data)

Usage

Uses

Used in Agricultural Applications:
(Z,E)-9,12-TETRADECADIENYLACETATE is used as a method and pesticidal mixture for controlling Pentatomidae pests. It is employed in the agricultural industry to manage and control these pests, which can cause significant damage to crops and reduce agricultural productivity. (Z,E)-9,12-TETRADECADIENYLACETATE's unique properties make it an effective tool in pest management strategies.
Used in Biological Studies:
In addition to its agricultural applications, (Z,E)-9,12-TETRADECADIENYLACETATE is also used in biological studies. Researchers utilize (Z,E)-9,12-TETRADECADIENYLACETATE to investigate various biological processes and interactions, particularly those related to pest control and management. (Z,E)-9,12-TETRADECADIENYLACETATE's unique characteristics make it a valuable tool for understanding the mechanisms of action and potential applications in biological research.

Synthesis Reference(s)

Tetrahedron Letters, 26, p. 2769, 1985 DOI: 10.1016/S0040-4039(00)94907-4

Synthetic route

Tetradeca-cis-9,trans-12-dien-1-ol (42521-46-0) + acetyl chloride (75-36-5) → Tetradec-9Z,12E-dien-1-yl Acetate (30507-70-1)

Conditions	Yield
With pyridine In tetrahydrofuran	93%

Tetradeca-cis-9,trans-12-dien-1-ol (42521-46-0) + acetic anhydride (108-24-7) → Tetradec-9Z,12E-dien-1-yl Acetate (30507-70-1) + (Z)-undec-9-en-1-ol (58257-52-6)

Conditions	Yield
With pyridine In dichloromethane at 20℃; for 18h; Inert atmosphere; chemoselective reaction;	A 89% B n/a

(E)-12-tetradec-9-yn-12-en-1-yl acetate (71394-01-9) → Tetradec-9Z,12E-dien-1-yl Acetate (30507-70-1)

Conditions	Yield
With hydrogen; sodium tetrahydroborate; nickel diacetate; ethylenediamine In ethanol Ambient temperature;	85%
With quinoline; hydrogen; Lindlar's catalyst In hexane at -10℃;	55.5%
With hydrogen; P-2Ni
With quinoline; hydrogen; Lindlar's catalyst In hexane at -10℃; Yield given;

(Z,E)-9,12-tetradecadien-1-ol (70654-44-3) + acetic anhydride (108-24-7) → Tetradec-9Z,12E-dien-1-yl Acetate (30507-70-1) + (9E,12E)-tetradeca-9,12-dien-1-yl acetate (70654-47-6) + (Z,Z)-9,12-tetradecadienyl acetate (51354-22-4) + (9E,12Z)-9,12-tetradecadienyl acetate (31654-77-0)

Conditions	Yield
In pyridine	A n/a B 83% C n/a D n/a

1-<(tetrahydro-2H-pyran-2-yl)oxy> 9Z, 12E-tetradecadiene (112464-06-9) + acetyl chloride (75-36-5) → Tetradec-9Z,12E-dien-1-yl Acetate (30507-70-1)

Conditions	Yield
With pyridine In acetic acid for 12h; Ambient temperature;	79.3%
With pyridine; acetic acid	72%

1-<(tetrahydro-2H-pyran-2-yl)oxy> 9Z, 12E-tetradecadiene (112464-06-9) → Tetradec-9Z,12E-dien-1-yl Acetate (30507-70-1)

Conditions	Yield
acetylation;	79%
Multi-step reaction with 2 steps 1: TsOH / methanol / Heating 2: pyridine View Scheme
Multi-step reaction with 2 steps 1: cc HCl / methanol / 5 h / Ambient temperature 2: 97 percent Chromat. / 4-dimethylaminopyridine / triethylamine View Scheme

1-<(tetrahydro-2H-pyran-2-yl)oxy> 9Z, 12E-tetradecadiene (112464-06-9) + acetic anhydride (108-24-7) → Tetradec-9Z,12E-dien-1-yl Acetate (30507-70-1)

Conditions	Yield
With titanium tetrachloride In dichloromethane at 0 - 25℃; for 6h; Acetylation;	78%

9-acetoxynonal (29541-97-7) + ((E)-Pent-3-enylidene)-triphenyl-λ5-phosphane (120593-09-1) → Tetradec-9Z,12E-dien-1-yl Acetate (30507-70-1)

Conditions	Yield
at -78℃;	62%

9-acetoxynonal (29541-97-7) + <(E)-3-Pentenyl>triphenylphosphonium-bromid (53143-96-7) → Tetradec-9Z,12E-dien-1-yl Acetate (30507-70-1)

Conditions	Yield
Stage #1: <(E)-3-Pentenyl>triphenylphosphonium-bromid With sodium hexamethyldisilazane In tetrahydrofuran at -78℃; for 1h; Inert atmosphere; Stage #2: 9-acetoxynonal In tetrahydrofuran at -78 - 20℃; for 24h; Inert atmosphere;	56%
Stage #1: <(E)-3-Pentenyl>triphenylphosphonium-bromid With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -20℃; for 1h; Stage #2: 9-acetoxynonal In tetrahydrofuran; hexane at -60 - 20℃; Wittig reaction; Further stages.;	54%

Tetradeca-cis-9,trans-12-dien-1-ol (42521-46-0) + acetic anhydride (108-24-7) → Tetradec-9Z,12E-dien-1-yl Acetate (30507-70-1)

Conditions	Yield
With pyridine Yield given;
With sodium acetate In neat (no solvent)

Tetradeca-cis-9,trans-12-dien-1-ol (42521-46-0) + acetic anhydride (108-24-7) → Tetradec-9Z,12E-dien-1-yl Acetate (30507-70-1) + (Z,Z)-9,12-tetradecadienyl acetate (51354-22-4)

Conditions	Yield
With dmap In triethylamine	A 97 % Chromat. B 3 % Chromat.

acetic anhydride (108-24-7) + (2E,5Z)-14-tert-Butoxy-tetradeca-2,5-diene (119649-90-0) → Tetradec-9Z,12E-dien-1-yl Acetate (30507-70-1)

Conditions	Yield
With iron(III) chloride In diethyl ether Ambient temperature; Yield given;

2-dec-9-ynyloxy-tetrahydro-pyran (19754-58-6) → Tetradec-9Z,12E-dien-1-yl Acetate (30507-70-1)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: BuLi / tetrahydrofuran; hexane / 0.5 h / 0 °C 1.2: 68 percent / tetrahydrofuran; hexane / 4 h / 20 °C 2.1: 85 percent / H2 / P-2 Ni / ethanol / 25 °C 3.1: 93 percent / pyridine / tetrahydrofuran View Scheme
Multi-step reaction with 3 steps 1.1: BuLi / tetrahydrofuran; hexane / 0.5 h / 0 °C 1.2: 75 percent / tetrahydrofuran; hexane / 4 h / 20 °C 2.1: 85 percent / H2 / P-2 Ni / ethanol / 25 °C 3.1: 93 percent / pyridine / tetrahydrofuran View Scheme
Multi-step reaction with 3 steps 1.1: BuLi / tetrahydrofuran; hexane / 0.5 h / 0 °C 1.2: 71 percent / tetrahydrofuran; hexane / 4 h / 20 °C 2.1: 85 percent / H2 / P-2 Ni / ethanol / 25 °C 3.1: 93 percent / pyridine / tetrahydrofuran View Scheme
Multi-step reaction with 3 steps 1: 1.) EtMgBr, 2.) CuBr / 1.) THF, heating, 1 h, 2.) reflux, 1 h, then at r. t., 36 h 2: acetic acid / 12 h / 80 °C 3: H2, quinoline / Lindlar catalyst / hexane / -10 °C View Scheme

9-decyn-1-ol (17643-36-6) → Tetradec-9Z,12E-dien-1-yl Acetate (30507-70-1)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: 95 percent / aq. HCl 2.1: BuLi / tetrahydrofuran; hexane / 0.5 h / 0 °C 2.2: 68 percent / tetrahydrofuran; hexane / 4 h / 20 °C 3.1: 85 percent / H2 / P-2 Ni / ethanol / 25 °C 4.1: 93 percent / pyridine / tetrahydrofuran View Scheme
Multi-step reaction with 4 steps 1.1: 95 percent / aq. HCl 2.1: BuLi / tetrahydrofuran; hexane / 0.5 h / 0 °C 2.2: 75 percent / tetrahydrofuran; hexane / 4 h / 20 °C 3.1: 85 percent / H2 / P-2 Ni / ethanol / 25 °C 4.1: 93 percent / pyridine / tetrahydrofuran View Scheme
Multi-step reaction with 4 steps 1.1: 95 percent / aq. HCl 2.1: BuLi / tetrahydrofuran; hexane / 0.5 h / 0 °C 2.2: 71 percent / tetrahydrofuran; hexane / 4 h / 20 °C 3.1: 85 percent / H2 / P-2 Ni / ethanol / 25 °C 4.1: 93 percent / pyridine / tetrahydrofuran View Scheme

(E)-Tetradec-12-en-9-yn-1-ol (42521-44-8) → Tetradec-9Z,12E-dien-1-yl Acetate (30507-70-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: 85 percent / H2 / P-2 Ni / ethanol / 25 °C 2: 93 percent / pyridine / tetrahydrofuran View Scheme

Tetrahydrofurfuryl chloride (3003-84-7) → Tetradec-9Z,12E-dien-1-yl Acetate (30507-70-1)

Conditions	Yield
Multi-step reaction with 5 steps 1: 60 percent / LiNH2 / Fe(3+) / tetrahydrofuran / 3 h 2: 79.6 percent / hydrogen / Lindlar's catalyst / pyridine 3: 69.7 percent / PBr3, pyridine / diethyl ether / 1.) overnight; 2.) 2 h, reflux 4: 2.) Li2CuCl4 / 1.) THF, -10 deg C, 30 min; 2.) THF, -10 deg C, 3 h 5: 79.3 percent / pyridine / acetic acid / 12 h / Ambient temperature View Scheme

(E)-Non-7-en-4-yn-1-ol (79532-18-6) → Tetradec-9Z,12E-dien-1-yl Acetate (30507-70-1)

Conditions	Yield
Multi-step reaction with 4 steps 1: 79.6 percent / hydrogen / Lindlar's catalyst / pyridine 2: 69.7 percent / PBr3, pyridine / diethyl ether / 1.) overnight; 2.) 2 h, reflux 3: 2.) Li2CuCl4 / 1.) THF, -10 deg C, 30 min; 2.) THF, -10 deg C, 3 h 4: 79.3 percent / pyridine / acetic acid / 12 h / Ambient temperature View Scheme

(4E,7E)-4,7-nonadien-1-ol (79532-19-7) → Tetradec-9Z,12E-dien-1-yl Acetate (30507-70-1)

Conditions	Yield
Multi-step reaction with 3 steps 1: 69.7 percent / PBr3, pyridine / diethyl ether / 1.) overnight; 2.) 2 h, reflux 2: 2.) Li2CuCl4 / 1.) THF, -10 deg C, 30 min; 2.) THF, -10 deg C, 3 h 3: 79.3 percent / pyridine / acetic acid / 12 h / Ambient temperature View Scheme

(4Z,7E)-4,7-nonadien-1-yl bromide (128342-65-4) → Tetradec-9Z,12E-dien-1-yl Acetate (30507-70-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: 2.) Li2CuCl4 / 1.) THF, -10 deg C, 30 min; 2.) THF, -10 deg C, 3 h 2: 79.3 percent / pyridine / acetic acid / 12 h / Ambient temperature View Scheme

1-(Tetrahydropyran-2-yloxy)tetradec-12E-en-9-yne (68516-29-0) → Tetradec-9Z,12E-dien-1-yl Acetate (30507-70-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: acetic acid / 12 h / 80 °C 2: H2, quinoline / Lindlar catalyst / hexane / -10 °C View Scheme

hex-trans-4-en-1-yne (31516-63-9) → Tetradec-9Z,12E-dien-1-yl Acetate (30507-70-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: 1.) lithium amide, 3.) pyridine 2: H2 / P-2Ni View Scheme

2-Ethylpyridine (100-71-0) + (+-)-3-bromo-butan-2-one → Tetradec-9Z,12E-dien-1-yl Acetate (30507-70-1)

Conditions	Yield
Multi-step reaction with 9 steps 1: 1.) n-BuLi / 1.) THF, -70 deg C, 2.) -70 deg C -> 0 deg C 2: methanol 3: 76 percent / NaBH4 / methanol 5: 77 percent / CsF / acetone / 4 h / Heating 7: Li2CuCl4 / tetrahydrofuran / 4 h / -30 °C 8: TsOH / methanol / Heating 9: pyridine View Scheme

7-tetrahydropyranyloxy-heptyl-magnesium chloride (81744-94-7) → Tetradec-9Z,12E-dien-1-yl Acetate (30507-70-1)

Conditions	Yield
Multi-step reaction with 3 steps 1: Li2CuCl4 / tetrahydrofuran / 4 h / -30 °C 2: TsOH / methanol / Heating 3: pyridine View Scheme

(2Z,5E)-1-(dimethylamino)heptadiene (83862-26-4) → Tetradec-9Z,12E-dien-1-yl Acetate (30507-70-1)

Conditions	Yield
Multi-step reaction with 4 steps 2: Li2CuCl4 / tetrahydrofuran / 4 h / -30 °C 3: TsOH / methanol / Heating 4: pyridine View Scheme

2-[1-(tert-Butyl-dimethyl-silanyl)-ethyl]-1-methyl-1,2,3,6-tetrahydro-pyridine (83862-22-0) → Tetradec-9Z,12E-dien-1-yl Acetate (30507-70-1)

Conditions	Yield
Multi-step reaction with 6 steps 2: 77 percent / CsF / acetone / 4 h / Heating 4: Li2CuCl4 / tetrahydrofuran / 4 h / -30 °C 5: TsOH / methanol / Heating 6: pyridine View Scheme

2-[1-(tert-Butyl-dimethyl-silanyl)-ethyl]-pyridine (83862-20-8) → Tetradec-9Z,12E-dien-1-yl Acetate (30507-70-1)

Conditions	Yield
Multi-step reaction with 8 steps 1: methanol 2: 76 percent / NaBH4 / methanol 4: 77 percent / CsF / acetone / 4 h / Heating 6: Li2CuCl4 / tetrahydrofuran / 4 h / -30 °C 7: TsOH / methanol / Heating 8: pyridine View Scheme

((2Z,5E)-Hepta-2,5-dienyl)-trimethyl-ammonium; iodide (83862-27-5) → Tetradec-9Z,12E-dien-1-yl Acetate (30507-70-1)

Conditions	Yield
Multi-step reaction with 3 steps 1: Li2CuCl4 / tetrahydrofuran / 4 h / -30 °C 2: TsOH / methanol / Heating 3: pyridine View Scheme

2-[1-(tert-Butyl-dimethyl-silanyl)-ethyl]-1,1-dimethyl-1,2,3,6-tetrahydro-pyridinium; iodide (83862-25-3) → Tetradec-9Z,12E-dien-1-yl Acetate (30507-70-1)

Conditions	Yield
Multi-step reaction with 5 steps 1: 77 percent / CsF / acetone / 4 h / Heating 3: Li2CuCl4 / tetrahydrofuran / 4 h / -30 °C 4: TsOH / methanol / Heating 5: pyridine View Scheme

2-[1-(tert-Butyl-dimethyl-silanyl)-ethyl]-1-methyl-pyridinium; iodide (83862-21-9) → Tetradec-9Z,12E-dien-1-yl Acetate (30507-70-1)

Conditions	Yield
Multi-step reaction with 7 steps 1: 76 percent / NaBH4 / methanol 3: 77 percent / CsF / acetone / 4 h / Heating 5: Li2CuCl4 / tetrahydrofuran / 4 h / -30 °C 6: TsOH / methanol / Heating 7: pyridine View Scheme

Tetradec-9Z,12E-dien-1-yl Acetate (30507-70-1) → Tetradeca-cis-9,trans-12-dien-1-ol (42521-46-0)

Conditions	Yield
With sodium hydroxide In methanol	71%
With sodium hydroxide In methanol at 20℃; for 3h;

Tetradec-9Z,12E-dien-1-yl Acetate (30507-70-1) → Acetic acid (9Z,11E)-13-hydroxy-tetradeca-9,11-dienyl ester

Conditions	Yield
(i) O2, (UV-irradiation), (ii) NaBH4; Multistep reaction;

Tetradec-9Z,12E-dien-1-yl Acetate (30507-70-1) → Acetic acid (10E,12E)-9-hydroxy-tetradeca-10,12-dienyl ester

Conditions	Yield
(i) O2, (UV-irradiation), (ii) NaBH4; Multistep reaction;

Upstream product

• 29541-97-7 9-acetoxynonal 
• 120593-09-1 ((E)-Pent-3-enylidene)-triphenyl-λ⁵-phosphane 
• 31516-63-9 hex-trans-4-en-1-yne 
• 100-71-0 2-Ethylpyridine 
• 66618-62-0 (E)-hept-5-en-2-yn-1-ol 
• 41368-47-2 (2Z,5E)-2,5-Heptadien-1-ol 
• 98291-64-6 Triphenyl-((E)-1-trimethylsilanyl-pent-3-enyl)-phosphonium; bromide 
• 55362-80-6 9-bromononan-1-ol 
• 764-37-4 (E)-3-penten-1-ol 
• 1617-32-9 (E)-3-pentenoic acid 
• 51937-00-9 (12E)-tetradeca-9,12-dien-1-ol 
• 108-24-7 acetic anhydride 
• 53143-96-7 <(E)-3-Pentenyl>triphenylphosphonium-bromid 
• 265315-63-7 acetoxynonanal 

Downstream Products

• 42521-46-0 Tetradeca-cis-9,trans-12-dien-1-ol 

Relevant articles and documents

Method for synthesizing (9Z, 12E)-9,12-tetradecadien-1-ol acetate

The invention belongs to the technical field of green pesticide synthesis, and discloses a novel method for synthesizing (9Z, 12E)-9,12-tetradecadien-1-ol acetate. According to the method, malonic acid and 9-bromo-1-nonyl alcohol are used as two starting raw materials. The method comprises the following steps: carrying out a Knoevenagel condensation reaction on malonic acid and propionaldehyde inthe presence of piperidine acetate to generate (E)-3-pentenoic acid, then carrying out lithium aluminum hydride reduction to obtain (E)-3-penten-1-ol, carrying out bromination reaction, and refluxingwith triphenylphosphine in acetonitrile to obtain (E)-3-pentenyltriphenylphosphine bromide; carrying out a PCC oxidation reaction on 9-bromo-1-nonanol to obtain 9-bromononanal, and then reacting the 9-bromononanal with potassium acetate to obtain 9-acetoxynonanal; and finally, carrying out a Wittig reaction on (E)-3-pentenyltriphenylphosphine bromide and 9-acetoxynonanal so as to obtain (9Z, 12E)-9,12-tetradecadien-1-ol acetate. An E-type double bond is constructed by utilizing the Knoevenagel condensation reaction of malonic acid and propionaldehyde, and the method has the advantages of mildreaction conditions, environmental friendliness, simple synthetic route and the like.

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PHEROMONES OF INSECTS AND THEIR ANALOGS. XXVIII. PRACTICAL SYNTHESIS OF TETRADECA-9Z,12E-DIEN-1-YL ACETATE - A COMPONENT OF THE SEX PHEROMONES OF INSECTS OF THE ORDER LEPIDOPTERA

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