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
• Article Data: 23

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

(9Z,12E)-Tetradecadien-1-ol Acetate can be used in agricultural use and biological study for method and pesticidal mixtures for controlling Pentatomidae pests.

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

• 42521-46-0 Tetradeca-cis-9,trans-12-dien-1-ol 
• 108-24-7 acetic anhydride 
• 19754-58-6 2-dec-9-ynyloxy-tetrahydro-pyran 
• 31516-63-9 hex-trans-4-en-1-yne 
• 83862-22-0 2-[1-(tert-Butyl-dimethyl-silanyl)-ethyl]-1-methyl-1,2,3,6-tetrahydro-pyridine 
• 83862-20-8 2-[1-(tert-Butyl-dimethyl-silanyl)-ethyl]-pyridine 
• 50816-20-1 2-(8-bromooctyloxy)tetrahydropyran 
• 81651-56-1 2-[((9E,12E)-Tetradeca-9,12-dienyl)oxy]-tetrahydro-pyran 
• 66618-62-0 (E)-hept-5-en-2-yn-1-ol 
• 29541-97-7 9-acetoxynonal 
• 53143-96-7 <(E)-3-Pentenyl>triphenylphosphonium-bromid 
• 51937-00-9 (12E)-tetradeca-9,12-dien-1-ol 
• 98291-64-6 Triphenyl-((E)-1-trimethylsilanyl-pent-3-enyl)-phosphonium; bromide 
• 112464-06-9 1-<(tetrahydro-2H-pyran-2-yl)oxy> 9Z, 12E-tetradecadiene 

Downstream Products

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

Relevant articles and documents

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