58594-45-9

Basic information

• Product Name: Z-13-OCTADECEN-1-AL
• Synonyms: Z-13-OCTADECEN-1-AL;cis-13-octadecenal;(Z)-13-octadecenal;13-Octadecenal, (13Z)-;13-Octadecenal, (Z)-;Einecs 261-349-4;(13Z)-;13Z-18CHO
• CAS NO: 58594-45-9
• Molecular Formula: C₁₈H₃₄O
• Molecular Weight: 266.46
• EINECS: 261-349-4
• Product Categories: Aliphatics
• Mol File: 58594-45-9.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 356 °C at 760 mmHg
• Flash Point: 179.2 °C
• Appearance: colorless to yellow liquid
• Density: 0.841±0.06 g/cm3 (20 ºC 760 Torr)
• Vapor Pressure: 3E-05mmHg at 25°C
• Refractive Index: 1.453
• Storage Temp.: Refrigerator, under inert atmosphere
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• CAS DataBase Reference: Z-13-OCTADECEN-1-AL(CAS DataBase Reference)
• NIST Chemistry Reference: Z-13-OCTADECEN-1-AL(58594-45-9)
• EPA Substance Registry System: Z-13-OCTADECEN-1-AL(58594-45-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• RIDADR: 1993
• HazardClass: 3.2
• PackingGroup: III
• Hazardous Substances Data: 58594-45-9(Hazardous Substances Data)

Usage

Uses

(Z)-13-Octadecenal is a sex pheromone component of the rice stem borer Chilo suppressalis (Lepidoptera).

InChI:InChI=1/C18H34O/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19/h5-6,18H,2-4,7-17H2,1H3/b6-5-

Synthetic route

C19H36O → (Z)-13-octadecenal (58594-45-9)

Conditions	Yield
With acetic acid In tetrahydrofuran; water at 55℃; for 10h;	95%

(Z)-octadec-13-en-1-ol (69820-27-5) → (Z)-13-octadecenal (58594-45-9)

Conditions	Yield
With pyridinium chlorochromate In dichloromethane at 20℃; for 3h;	75%
With dipyridinium dichromate In dichloromethane for 24h;	60%
With Py*HClCrO3
With pyridinium chlorochromate In dichloromethane at 20℃; for 16h;

4-(Z)-nonenemagnesium bromide (82260-32-0, 142524-63-8) → (Z)-13-octadecenal (58594-45-9)

Conditions	Yield
Multi-step reaction with 3 steps 1: 54 percent / Li2CuCl4 / tetrahydrofuran / 3 h / -10 °C 2: 53 percent / pyridinium p-toluenesulfonate / methanol / 6 h / 55 °C 3: 60 percent / pyridinium dichromate / CH2Cl2 / 24 h View Scheme

1-tetrahydropyranyloxy-13-(Z)-octadecene (130253-49-5) → (Z)-13-octadecenal (58594-45-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: 53 percent / pyridinium p-toluenesulfonate / methanol / 6 h / 55 °C 2: 60 percent / pyridinium dichromate / CH2Cl2 / 24 h View Scheme
Multi-step reaction with 2 steps 1: pyridinium p-toluenesulfonate / ethanol / 80 °C 2: pyridinium chlorochromate / dichloromethane / 3 h / 20 °C View Scheme
Multi-step reaction with 2 steps 1: toluene-4-sulfonic acid / methanol / 16 h / 20 °C 2: pyridinium chlorochromate / dichloromethane / 16 h / 20 °C View Scheme

methyl cis-13-docosenoate (1120-34-9) → (Z)-13-octadecenal (58594-45-9)

Conditions	Yield
Multi-step reaction with 4 steps 1: (i) O3, (ii) Ph3P 3: LiAlH4 / diethyl ether / Heating 4: Py*HClCrO3 View Scheme

methyl 12-formyldodecanoate (1608-77-1) → (Z)-13-octadecenal (58594-45-9)

Conditions	Yield
Multi-step reaction with 3 steps 2: LiAlH4 / diethyl ether / Heating 3: Py*HClCrO3 View Scheme

cis-13-octadecenoic acid, methyl ester (13058-55-4) → (Z)-13-octadecenal (58594-45-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: LiAlH4 / diethyl ether / Heating 2: Py*HClCrO3 View Scheme

(Z)-1-(tetrahydropyran-2-yloxy)-4-nonene (146176-63-8) → (Z)-13-octadecenal (58594-45-9)

Conditions	Yield
Multi-step reaction with 5 steps 1: pyridinium p-toluenesulfonate / methanol / 80 °C 2: pyridine 3: dilithium tetrachlorocuprate; magnesium / tetrahydrofuran 4: pyridinium p-toluenesulfonate / ethanol / 80 °C 5: pyridinium chlorochromate / dichloromethane / 3 h / 20 °C View Scheme

(Z)-4-nonen-1-ol (59499-28-4) → (Z)-13-octadecenal (58594-45-9)

Conditions	Yield
Multi-step reaction with 4 steps 1: pyridine 2: dilithium tetrachlorocuprate; magnesium / tetrahydrofuran 3: pyridinium p-toluenesulfonate / ethanol / 80 °C 4: pyridinium chlorochromate / dichloromethane / 3 h / 20 °C View Scheme

1-tosyloxynon-4Z-ene (83165-98-4) → (Z)-13-octadecenal (58594-45-9)

Conditions	Yield
Multi-step reaction with 3 steps 1: dilithium tetrachlorocuprate; magnesium / tetrahydrofuran 2: pyridinium p-toluenesulfonate / ethanol / 80 °C 3: pyridinium chlorochromate / dichloromethane / 3 h / 20 °C View Scheme

2-(9-bromononyloxy)tetrahydropyran (55695-90-4) → (Z)-13-octadecenal (58594-45-9)

Conditions	Yield
Multi-step reaction with 3 steps 1: dilithium tetrachlorocuprate; magnesium / tetrahydrofuran 2: pyridinium p-toluenesulfonate / ethanol / 80 °C 3: pyridinium chlorochromate / dichloromethane / 3 h / 20 °C View Scheme

1,5-cis,cis-cyclooctadiene (1552-12-1, 111-78-4) → (Z)-13-octadecenal (58594-45-9)

Conditions

Yield

Multi-step reaction with 9 steps 1: peracetic acid / dichloromethane 2: pyridinium p-toluenesulfonate / tetrahydrofuran 3: pyridine / 4 h / 20 °C 4: dilithium tetrachlorocuprate / tetrahydrofuran / 3 h / -40 °C 5: pyridinium p-toluenesulfonate / methanol / 80 °C 6: pyridine 7: dilithium tetrachlorocuprate; magnesium / tetrahydrofuran 8: pyridinium p-toluenesulfonate / ethanol / 80 °C 9: pyridinium chlorochromate / dichloromethane / 3 h / 20 °C View Scheme

1,9-Nonanediol (3937-56-2) → (Z)-13-octadecenal (58594-45-9)

Conditions	Yield
Multi-step reaction with 5 steps 1: hydrogen bromide / benzene 2: pyridinium p-toluenesulfonate / dichloromethane 3: dilithium tetrachlorocuprate; magnesium / tetrahydrofuran 4: pyridinium p-toluenesulfonate / ethanol / 80 °C 5: pyridinium chlorochromate / dichloromethane / 3 h / 20 °C View Scheme

9-bromononan-1-ol (55362-80-6) → (Z)-13-octadecenal (58594-45-9)

Conditions	Yield
Multi-step reaction with 4 steps 1: pyridinium p-toluenesulfonate / dichloromethane 2: dilithium tetrachlorocuprate; magnesium / tetrahydrofuran 3: pyridinium p-toluenesulfonate / ethanol / 80 °C 4: pyridinium chlorochromate / dichloromethane / 3 h / 20 °C View Scheme

(Z)-oct-4-ene-1,8-diol (56506-08-2, 62422-45-1) → (Z)-13-octadecenal (58594-45-9)

Conditions

Yield

Multi-step reaction with 8 steps 1: pyridinium p-toluenesulfonate / tetrahydrofuran 2: pyridine / 4 h / 20 °C 3: dilithium tetrachlorocuprate / tetrahydrofuran / 3 h / -40 °C 4: pyridinium p-toluenesulfonate / methanol / 80 °C 5: pyridine 6: dilithium tetrachlorocuprate; magnesium / tetrahydrofuran 7: pyridinium p-toluenesulfonate / ethanol / 80 °C 8: pyridinium chlorochromate / dichloromethane / 3 h / 20 °C View Scheme

(Z)-8-<(tetrahydropyran-2-yl)oxy>oct-4-enol (62422-46-2) → (Z)-13-octadecenal (58594-45-9)

Conditions	Yield
Multi-step reaction with 7 steps 1: pyridine / 4 h / 20 °C 2: dilithium tetrachlorocuprate / tetrahydrofuran / 3 h / -40 °C 3: pyridinium p-toluenesulfonate / methanol / 80 °C 4: pyridine 5: dilithium tetrachlorocuprate; magnesium / tetrahydrofuran 6: pyridinium p-toluenesulfonate / ethanol / 80 °C 7: pyridinium chlorochromate / dichloromethane / 3 h / 20 °C View Scheme

(Z)-8-(tetrahydro-2H-pyran-2-yloxy)oct-4-enyl 4-methylbenzensulfonate (108536-01-2) → (Z)-13-octadecenal (58594-45-9)

Conditions	Yield
Multi-step reaction with 6 steps 1: dilithium tetrachlorocuprate / tetrahydrofuran / 3 h / -40 °C 2: pyridinium p-toluenesulfonate / methanol / 80 °C 3: pyridine 4: dilithium tetrachlorocuprate; magnesium / tetrahydrofuran 5: pyridinium p-toluenesulfonate / ethanol / 80 °C 6: pyridinium chlorochromate / dichloromethane / 3 h / 20 °C View Scheme

1,12-dodecandiol (5675-51-4) → (Z)-13-octadecenal (58594-45-9)

Conditions

Yield

Multi-step reaction with 6 steps 1.1: hydrogen bromide / toluene / 16 h / 120 °C 2.1: toluene-4-sulfonic acid / dichloromethane / 16.5 h / 0 - 20 °C 3.1: n-butyllithium / hexane; tetrahydrofuran / 1 h / -30 - 0 °C / Inert atmosphere 3.2: 16 h / Reflux 4.1: potassium hydroxide; palladium diacetate / N,N-dimethyl-formamide / 16 h / 145 °C / Sealed tube 5.1: toluene-4-sulfonic acid / methanol / 16 h / 20 °C 6.1: pyridinium chlorochromate / dichloromethane / 16 h / 20 °C View Scheme

12-bromododecanol (3344-77-2) → (Z)-13-octadecenal (58594-45-9)

Conditions

Yield

Multi-step reaction with 5 steps 1.1: toluene-4-sulfonic acid / dichloromethane / 16.5 h / 0 - 20 °C 2.1: n-butyllithium / hexane; tetrahydrofuran / 1 h / -30 - 0 °C / Inert atmosphere 2.2: 16 h / Reflux 3.1: potassium hydroxide; palladium diacetate / N,N-dimethyl-formamide / 16 h / 145 °C / Sealed tube 4.1: toluene-4-sulfonic acid / methanol / 16 h / 20 °C 5.1: pyridinium chlorochromate / dichloromethane / 16 h / 20 °C View Scheme

C23H42O2 → (Z)-13-octadecenal (58594-45-9)

Conditions	Yield
Multi-step reaction with 3 steps 1: potassium hydroxide; palladium diacetate / N,N-dimethyl-formamide / 16 h / 145 °C / Sealed tube 2: toluene-4-sulfonic acid / methanol / 16 h / 20 °C 3: pyridinium chlorochromate / dichloromethane / 16 h / 20 °C View Scheme

2-[(12-bromododecyl)oxy]tetrahydro-2H-pyran (112999-97-0, 88517-92-4) → (Z)-13-octadecenal (58594-45-9)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: n-butyllithium / hexane; tetrahydrofuran / 1 h / -30 - 0 °C / Inert atmosphere 1.2: 16 h / Reflux 2.1: potassium hydroxide; palladium diacetate / N,N-dimethyl-formamide / 16 h / 145 °C / Sealed tube 3.1: toluene-4-sulfonic acid / methanol / 16 h / 20 °C 4.1: pyridinium chlorochromate / dichloromethane / 16 h / 20 °C View Scheme

(Z)-13-octadecenal (58594-45-9) → (Z)-octadec-13-en-1-ol (69820-27-5)

Conditions	Yield
With sodium tetrahydroborate; water; sodium hydroxide In methanol for 4h; Cooling with ice;	88%

(Z)-13-octadecenal (58594-45-9) + 1,2-bis(tert-butyldimethylsilyl)hydrazine (10000-20-1) → Z-13-octadecenal N-tert-butyldimethylsilylhydrazone + Z-13-octadecenal N-tert-butyldimethylsilylhydrazone

Conditions	Yield
With scandium tris(trifluoromethanesulfonate) at 0 - 23℃; Title compound not separated from byproducts;

(Z)-13-octadecenal (58594-45-9) + 1,2-bis(tert-butyldimethylsilyl)hydrazine (10000-20-1) → 13-octadecenal N-tert-butyldimethylsilylhydrazone

Conditions	Yield
With scandium tris(trifluoromethanesulfonate) In acetonitrile at 0 - 23℃; for 0.5h;

(Z)-13-octadecenal (58594-45-9) → 2,2-dimethylpropionic acid Z-13-octadecenyl ester ster

Conditions	Yield
Multi-step reaction with 2 steps 1: Sc(OTf)3 / acetonitrile / 0.5 h / 0 - 23 °C 2: 0.125 g / iodosylbenzene; aq. hydrofluoric acid; 2-chloropyridine / CH2Cl2 / 13.5 h / -78 - 23 °C View Scheme

Upstream product

• 69820-27-5 (Z)-octadec-13-en-1-ol 
• 55362-80-6 9-bromononan-1-ol 
• 3937-56-2 1,9-Nonanediol 
• 1552-12-1 1,5-cis,cis-cyclooctadiene 
• 55695-90-4 2-(9-bromononyloxy)tetrahydropyran 
• 83165-98-4 1-tosyloxynon-4Z-ene 
• 59499-28-4 (Z)-4-nonen-1-ol 
• 146176-63-8 (Z)-1-(tetrahydropyran-2-yloxy)-4-nonene 
• 13058-55-4 cis-13-octadecenoic acid, methyl ester 
• 1608-77-1 methyl 12-formyldodecanoate 
• 1120-34-9 methyl cis-13-docosenoate 
• 130253-49-5 1-tetrahydropyranyloxy-13-(Z)-octadecene 
• 82260-32-0 4-(Z)-nonenemagnesium bromide 
• 112999-97-0 2-[(12-bromododecyl)oxy]tetrahydro-2H-pyran 

Downstream Products

• 69820-27-5 (Z)-octadec-13-en-1-ol 

Relevant articles and documents

Practical Synthesis and Field Application of the Synthetic Sex Pheromone of Rice Stem Borer, Chilo suppressalis (Lepidoptera: Pyralidae)

Rice stem borer, Chilo suppressalis, is a common and major serious pest of rice, maize, and wheat crops across Asia, Europe, and Oceania countries. Its sex pheromone consists of three analogously compounds, i.e., (Z)-hexadec-11-enal (1), (Z)-octadec-13-enal (2), and (Z)-hexadec-9-enal (3), as long-chain aliphatic internal cis-alkenyl aldehydes. In order to perform an economic and widespread pest control management of rice stem borer, a versatile and efficient synthetic strategy is required. A versatile and efficient synthesis using a common synthetic route for cis-alkenals with high overall yields is described. Commercially available inexpensive aliphatic diols were chosen as starting materials. Two key steps were employed to synthesize the long-chain aliphatic internal cis-alkenes in excellent yields, including the alkylation of terminal alkynes without the utilization of a highly polar aprotic cosolvent and the versatile cis-selective semihydrogenation for the reduction of internal alkynes with excellent stereoselectivity. The results of field tests showed that the synthetic sex pheromone blend was highly effective for the capture of rice stem borer.

The stereospecific synthesis of the rice leaffolder moth sex pheromone components from 1,5-cyclooctadiene

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Pheromones, XXVII. Stereoselective synthesis of (Z)-13-octadecenal, a pheromone component of the rice stem borer Chilo suppressalis (Lepidoptera)

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