56219-04-6

Basic information

• Product Name: CIS-9-HEXADECENAL, 95
• Synonyms: CIS-9-HEXADECENAL, 95;(9Z)-9-Hexadecenal;(z)-9-hexadecena;(Z)-hexadec-9-enal;(Z)-9-HDAL, Z-9-HDAL;9-Hexadecenal, (9Z)-;Einecs 260-064-2;PalMitolealdehyde
• CAS NO: 56219-04-6
• Molecular Formula: C₁₆H₃₀O
• Molecular Weight: 238.4088
• EINECS: 260-064-2
• Product Categories: Aliphatics
• Mol File: 56219-04-6.mol
• Article Data: 13

Chemical Properties

• Boiling Point: 330.9°Cat760mmHg
• Flash Point: 62 °C
• Appearance: /
• Density: 0.840±0.06 g/cm3 (20 ºC 760 Torr)
• Vapor Pressure: 0.000161mmHg at 25°C
• Refractive Index: 1.4600 (25℃)
• Storage Temp.: −20°C
• CAS DataBase Reference: CIS-9-HEXADECENAL, 95(CAS DataBase Reference)
• NIST Chemistry Reference: CIS-9-HEXADECENAL, 95(56219-04-6)
• EPA Substance Registry System: CIS-9-HEXADECENAL, 95(56219-04-6)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 56219-04-6(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 56219-04-6 differently. You can refer to the following data:
1. A component of the sex pheromone of the cotton bollworm Heliothis armigera.
2. (Z)-9-Hexadecenal is a component of the sex pheromone of the cotton bollworm Heliothis armigera.

Hazard

Low toxicity by ingestion.

InChI:InChI=1/C16H30O/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17/h7-8,16H,2-6,9-15H2,1H3/b8-7-

Synthetic route

palmitoleyl alcohol (10378-01-5) → (Z)-9-hexadecenal (56219-04-6)

Conditions	Yield
With pyridinium chlorochromate In dichloromethane at 20℃; for 2h;	98%
With pyridinium chlorochromate In dichloromethane for 1.5h; Ambient temperature;	94%
With pyridinium chlorochromate	94%

(Z)-4-undecene-1-ol (21676-07-3) → (Z)-9-hexadecenal (56219-04-6)

Conditions	Yield
Multi-step reaction with 4 steps 1: 96 percent / triphenylphosphine, Br2 / CCl4 / 16 h / Ambient temperature 2: 1.) cuprous iodide, 2,2' bipyridyl / 1.) THF, 2 deg C, 10 min, 2.) THF, a) 2 deg C, 2 h, b) RT, 15 h 3: p-toluenesulfonic acid / methanol; H2O / 15 h / 20 °C 4: 94 percent / pyridinium chlorochromate / CH2Cl2 / 1.5 h / Ambient temperature View Scheme

(Z)-4-undecenal (68820-32-6) → (Z)-9-hexadecenal (56219-04-6)

Conditions

Yield

Multi-step reaction with 5 steps 1: 95 percent / diisobutylaluminum hydride / diethyl ether; toluene / 1.5 h / -10 °C 2: 96 percent / triphenylphosphine, Br2 / CCl4 / 16 h / Ambient temperature 3: 1.) cuprous iodide, 2,2' bipyridyl / 1.) THF, 2 deg C, 10 min, 2.) THF, a) 2 deg C, 2 h, b) RT, 15 h 4: p-toluenesulfonic acid / methanol; H2O / 15 h / 20 °C 5: 94 percent / pyridinium chlorochromate / CH2Cl2 / 1.5 h / Ambient temperature View Scheme

(Z)-4-undecenyl bromide (109523-23-1) → (Z)-9-hexadecenal (56219-04-6)

Conditions	Yield
Multi-step reaction with 3 steps 1: 1.) cuprous iodide, 2,2' bipyridyl / 1.) THF, 2 deg C, 10 min, 2.) THF, a) 2 deg C, 2 h, b) RT, 15 h 2: p-toluenesulfonic acid / methanol; H2O / 15 h / 20 °C 3: 94 percent / pyridinium chlorochromate / CH2Cl2 / 1.5 h / Ambient temperature View Scheme

1,1-dimethoxy-8-tosyloxy-(4Z)-octene (82861-01-6) → (Z)-9-hexadecenal (56219-04-6)

Conditions

Yield

Multi-step reaction with 7 steps 1: 63 percent / dilithium tetrachlorocuprate / tetrahydrofuran / 1.) -78 deg C, 2 h, 2.) RT, 15 h 2: 99 percent / 5percent HCl / acetone / 6 h / Ambient temperature 3: 95 percent / diisobutylaluminum hydride / diethyl ether; toluene / 1.5 h / -10 °C 4: 96 percent / triphenylphosphine, Br2 / CCl4 / 16 h / Ambient temperature 5: 1.) cuprous iodide, 2,2' bipyridyl / 1.) THF, 2 deg C, 10 min, 2.) THF, a) 2 deg C, 2 h, b) RT, 15 h 6: p-toluenesulfonic acid / methanol; H2O / 15 h / 20 °C 7: 94 percent / pyridinium chlorochromate / CH2Cl2 / 1.5 h / Ambient temperature View Scheme

1,1-dimethoxy-(4Z)-undecene (104187-94-2) → (Z)-9-hexadecenal (56219-04-6)

Conditions

Yield

Multi-step reaction with 6 steps 1: 99 percent / 5percent HCl / acetone / 6 h / Ambient temperature 2: 95 percent / diisobutylaluminum hydride / diethyl ether; toluene / 1.5 h / -10 °C 3: 96 percent / triphenylphosphine, Br2 / CCl4 / 16 h / Ambient temperature 4: 1.) cuprous iodide, 2,2' bipyridyl / 1.) THF, 2 deg C, 10 min, 2.) THF, a) 2 deg C, 2 h, b) RT, 15 h 5: p-toluenesulfonic acid / methanol; H2O / 15 h / 20 °C 6: 94 percent / pyridinium chlorochromate / CH2Cl2 / 1.5 h / Ambient temperature View Scheme

(Z)-16-(1-Ethoxy-ethoxy)-hexadec-7-ene → (Z)-9-hexadecenal (56219-04-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: p-toluenesulfonic acid / methanol; H2O / 15 h / 20 °C 2: 94 percent / pyridinium chlorochromate / CH2Cl2 / 1.5 h / Ambient temperature View Scheme

methyl aleuritate → (Z)-9-hexadecenal (56219-04-6)

Conditions

Yield

Multi-step reaction with 4 steps 1.1: 60.91 percent / aq. NaIO4 / acetonitrile / 0.5 h / 5 °C 2.1: sodium amide / tetrahydrofuran; hexamethylphosphoric acid triamide / 1.5 h / 20 °C 2.2: 91.52 percent / tetrahydrofuran; hexamethylphosphoric acid triamide / -73 - 20 °C 3.1: 92 percent / lithium aluminum hydride / tetrahydrofuran / 2 h / 0 °C 4.1: 66.64 percent / pyridinium chlorochromate / CH2Cl2 / 3 h / 20 °C View Scheme

(Z)-9-hexadecenoic acid methyl ester (1120-25-8) → (Z)-9-hexadecenal (56219-04-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: 92 percent / lithium aluminum hydride / tetrahydrofuran / 2 h / 0 °C 2: 66.64 percent / pyridinium chlorochromate / CH2Cl2 / 3 h / 20 °C View Scheme
Multi-step reaction with 2 steps 1: 96 percent / LAH / tetrahydrofuran / 5 h / -10 - 20 °C 2: 84 percent / pyridinium chlorochromate / CH2Cl2 / 1 h / Ambient temperature View Scheme
With 1-methyl-piperazine; sodium bis(2-methoxyethoxy)aluminium dihydride In toluene at 20℃; for 2h; Sealed tube; Inert atmosphere; Cooling with ice;

methyl ester of azelaic acid aldehyde (1931-63-1) → (Z)-9-hexadecenal (56219-04-6)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: sodium amide / tetrahydrofuran; hexamethylphosphoric acid triamide / 1.5 h / 20 °C 1.2: 91.52 percent / tetrahydrofuran; hexamethylphosphoric acid triamide / -73 - 20 °C 2.1: 92 percent / lithium aluminum hydride / tetrahydrofuran / 2 h / 0 °C 3.1: 66.64 percent / pyridinium chlorochromate / CH2Cl2 / 3 h / 20 °C View Scheme
Multi-step reaction with 3 steps 1: 1.) NaNH2 / 1.) THF, RT, 1 h, 2.) THF, from -10 deg C to RT 2: 96 percent / LAH / tetrahydrofuran / 5 h / -10 - 20 °C 3: 84 percent / pyridinium chlorochromate / CH2Cl2 / 1 h / Ambient temperature View Scheme

triphenylheptylphosphonium bromide (13423-48-8) → (Z)-9-hexadecenal (56219-04-6)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: sodium amide / tetrahydrofuran; hexamethylphosphoric acid triamide / 1.5 h / 20 °C 1.2: 91.52 percent / tetrahydrofuran; hexamethylphosphoric acid triamide / -73 - 20 °C 2.1: 92 percent / lithium aluminum hydride / tetrahydrofuran / 2 h / 0 °C 3.1: 66.64 percent / pyridinium chlorochromate / CH2Cl2 / 3 h / 20 °C View Scheme
Multi-step reaction with 3 steps 1: 1.) sodium bis(trimethylsilyl)amide / 1.) THF, from 50 to 55 deg C, 60 min, 2.) THF, a) -78 deg C, 30 min, b) 20 deg C, 12 h 2: 82 percent / LiAlH4 / diethyl ether / 5 h / 20 °C 3: 67 percent / pyridinium chlorochromate / CH2Cl2 / 0.67 h / 20 °C View Scheme

(+)-threo-9,10,16-trihydroxyhexadecanoic acid → (Z)-9-hexadecenal (56219-04-6)

Conditions

Yield

Multi-step reaction with 5 steps 1.1: 97.95 percent / aq. H2SO4 / 0.11 h / microwave irradiation 2.1: 60.91 percent / aq. NaIO4 / acetonitrile / 0.5 h / 5 °C 3.1: sodium amide / tetrahydrofuran; hexamethylphosphoric acid triamide / 1.5 h / 20 °C 3.2: 91.52 percent / tetrahydrofuran; hexamethylphosphoric acid triamide / -73 - 20 °C 4.1: 92 percent / lithium aluminum hydride / tetrahydrofuran / 2 h / 0 °C 5.1: 66.64 percent / pyridinium chlorochromate / CH2Cl2 / 3 h / 20 °C View Scheme

8-Bromo-1-octene (2695-48-9) → (Z)-9-hexadecenal (56219-04-6)

Conditions	Yield
Multi-step reaction with 4 steps 1: 87 percent / NH3 2: 1) 9-BBN, 2) H2O2, AcONa 3: 88 percent / H2 / Ni-P2 4: 94 percent / PCC View Scheme

1-octynyllithium (21433-45-4) → (Z)-9-hexadecenal (56219-04-6)

Conditions	Yield
Multi-step reaction with 4 steps 1: 87 percent / NH3 2: 1) 9-BBN, 2) H2O2, AcONa 3: 88 percent / H2 / Ni-P2 4: 94 percent / PCC View Scheme

9-hexadecyn-1-ol (88109-73-3) → (Z)-9-hexadecenal (56219-04-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: 88 percent / H2 / Ni-P2 2: 94 percent / PCC View Scheme
Multi-step reaction with 2 steps 1: H2 / Cu/γ-Al2O3 / 3.33 h / 119.9 °C / 60004.8 Torr / other supported catalyst; other time; stereoselective hydrogenation of C16 acetylenic alcohols on supported copper catalyst View Scheme
Multi-step reaction with 2 steps 1: 1.) iso-BuMgBr, 2.) Cp2TiCl2 / 1.) diethyl ether, 0 deg C, 15 min, 2.) diethyl ether, RT, 3 h 2: 98 percent / pyridinium chlorochromate / CH2Cl2 / 2 h / 20 °C View Scheme

hexadec-1-en-9-yne (197901-27-2) → (Z)-9-hexadecenal (56219-04-6)

Conditions	Yield
Multi-step reaction with 3 steps 1: 1) 9-BBN, 2) H2O2, AcONa 2: 88 percent / H2 / Ni-P2 3: 94 percent / PCC View Scheme

10,11-dibromo-undecanoic acid (6308-96-9) → (Z)-9-hexadecenal (56219-04-6)

Conditions

Yield

Multi-step reaction with 7 steps 1: KOH, PEG 400 / 0.5 h / 150 - 200 °C 2: p-TSA / 12 h / Ambient temperature 3: 96 percent / H2, quinoline / 5percent Pd/BaSO4 / hexane / Ambient temperature 4: 84 percent / O3 / CH2Cl2 / -78 °C 5: 1.) NaNH2 / 1.) THF, RT, 1 h, 2.) THF, from -10 deg C to RT 6: 96 percent / LAH / tetrahydrofuran / 5 h / -10 - 20 °C 7: 84 percent / pyridinium chlorochromate / CH2Cl2 / 1 h / Ambient temperature View Scheme

10-undecenoic acid (112-38-9) + aqueous KOH-solution → (Z)-9-hexadecenal (56219-04-6)

Conditions

Yield

Multi-step reaction with 8 steps 1: 97 percent / Br2 / CCl4 / 1.5 h 2: KOH, PEG 400 / 0.5 h / 150 - 200 °C 3: p-TSA / 12 h / Ambient temperature 4: 96 percent / H2, quinoline / 5percent Pd/BaSO4 / hexane / Ambient temperature 5: 84 percent / O3 / CH2Cl2 / -78 °C 6: 1.) NaNH2 / 1.) THF, RT, 1 h, 2.) THF, from -10 deg C to RT 7: 96 percent / LAH / tetrahydrofuran / 5 h / -10 - 20 °C 8: 84 percent / pyridinium chlorochromate / CH2Cl2 / 1 h / Ambient temperature View Scheme

9-undecynoic acid (22202-65-9) + hydrogen → (Z)-9-hexadecenal (56219-04-6)

Conditions

Yield

Multi-step reaction with 6 steps 1: p-TSA / 12 h / Ambient temperature 2: 96 percent / H2, quinoline / 5percent Pd/BaSO4 / hexane / Ambient temperature 3: 84 percent / O3 / CH2Cl2 / -78 °C 4: 1.) NaNH2 / 1.) THF, RT, 1 h, 2.) THF, from -10 deg C to RT 5: 96 percent / LAH / tetrahydrofuran / 5 h / -10 - 20 °C 6: 84 percent / pyridinium chlorochromate / CH2Cl2 / 1 h / Ambient temperature View Scheme

9-undecynoic acid methyl ester (18937-76-3) → (Z)-9-hexadecenal (56219-04-6)

Conditions	Yield
Multi-step reaction with 5 steps 1: 96 percent / H2, quinoline / 5percent Pd/BaSO4 / hexane / Ambient temperature 2: 84 percent / O3 / CH2Cl2 / -78 °C 3: 1.) NaNH2 / 1.) THF, RT, 1 h, 2.) THF, from -10 deg C to RT 4: 96 percent / LAH / tetrahydrofuran / 5 h / -10 - 20 °C 5: 84 percent / pyridinium chlorochromate / CH2Cl2 / 1 h / Ambient temperature View Scheme

(Z)-0-undecenoic acid methyl ester (54299-07-9) → (Z)-9-hexadecenal (56219-04-6)

Conditions	Yield
Multi-step reaction with 4 steps 1: 84 percent / O3 / CH2Cl2 / -78 °C 2: 1.) NaNH2 / 1.) THF, RT, 1 h, 2.) THF, from -10 deg C to RT 3: 96 percent / LAH / tetrahydrofuran / 5 h / -10 - 20 °C 4: 84 percent / pyridinium chlorochromate / CH2Cl2 / 1 h / Ambient temperature View Scheme

2-(8-bromooctyloxy)tetrahydropyran (50816-20-1) → (Z)-9-hexadecenal (56219-04-6)

Conditions	Yield
Multi-step reaction with 4 steps 1: 1.) LiNH2, HMPTA / 1.) RT, 1 h, 2.) a) 10 deg C, 1 h, b) RT, 15 h, c) 55 deg C, 10 h 2: 85 percent / p-TsOH / methanol; H2O / 18 h / 20 °C 3: 1.) iso-BuMgBr, 2.) Cp2TiCl2 / 1.) diethyl ether, 0 deg C, 15 min, 2.) diethyl ether, RT, 3 h 4: 98 percent / pyridinium chlorochromate / CH2Cl2 / 2 h / 20 °C View Scheme
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

1,8-Octanediol (629-41-4) + primary-secondary glycol C8H18O2 → (Z)-9-hexadecenal (56219-04-6)

Conditions

Yield

Multi-step reaction with 6 steps 1: 75 percent / 48percent HBr / Heating 2: 99 percent / p-toluenesulfonic acid 3: 1.) LiNH2, HMPTA / 1.) RT, 1 h, 2.) a) 10 deg C, 1 h, b) RT, 15 h, c) 55 deg C, 10 h 4: 85 percent / p-TsOH / methanol; H2O / 18 h / 20 °C 5: 1.) iso-BuMgBr, 2.) Cp2TiCl2 / 1.) diethyl ether, 0 deg C, 15 min, 2.) diethyl ether, RT, 3 h 6: 98 percent / pyridinium chlorochromate / CH2Cl2 / 2 h / 20 °C View Scheme

8-bromooctanol (50816-19-8) → (Z)-9-hexadecenal (56219-04-6)

Conditions	Yield
Multi-step reaction with 5 steps 1: 99 percent / p-toluenesulfonic acid 2: 1.) LiNH2, HMPTA / 1.) RT, 1 h, 2.) a) 10 deg C, 1 h, b) RT, 15 h, c) 55 deg C, 10 h 3: 85 percent / p-TsOH / methanol; H2O / 18 h / 20 °C 4: 1.) iso-BuMgBr, 2.) Cp2TiCl2 / 1.) diethyl ether, 0 deg C, 15 min, 2.) diethyl ether, RT, 3 h 5: 98 percent / pyridinium chlorochromate / CH2Cl2 / 2 h / 20 °C View Scheme
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

1-tetrahydropyranyloxy-n-9-hexadecyn (25258-24-6) → (Z)-9-hexadecenal (56219-04-6)

Conditions	Yield
Multi-step reaction with 3 steps 1: 85 percent / p-TsOH / methanol; H2O / 18 h / 20 °C 2: 1.) iso-BuMgBr, 2.) Cp2TiCl2 / 1.) diethyl ether, 0 deg C, 15 min, 2.) diethyl ether, RT, 3 h 3: 98 percent / pyridinium chlorochromate / CH2Cl2 / 2 h / 20 °C View Scheme
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

9-acetoxynonal (29541-97-7) → (Z)-9-hexadecenal (56219-04-6)

Conditions	Yield
Multi-step reaction with 3 steps 1: 1.) sodium bis(trimethylsilyl)amide / 1.) THF, from 50 to 55 deg C, 60 min, 2.) THF, a) -78 deg C, 30 min, b) 20 deg C, 12 h 2: 82 percent / LiAlH4 / diethyl ether / 5 h / 20 °C 3: 67 percent / pyridinium chlorochromate / CH2Cl2 / 0.67 h / 20 °C View Scheme

(Z)-hexadec-9-en-1-yl acetate (34010-20-3) → (Z)-9-hexadecenal (56219-04-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: 82 percent / LiAlH4 / diethyl ether / 5 h / 20 °C 2: 67 percent / pyridinium chlorochromate / CH2Cl2 / 0.67 h / 20 °C View Scheme

2-dec-9-ynyloxy-tetrahydro-pyran (19754-58-6) → (Z)-9-hexadecenal (56219-04-6)

Conditions	Yield
Multi-step reaction with 4 steps 1: LiNH2 / liquid ammonia 2: p-TsOH / methanol 3: 86 percent / H2 / P2Ni 4: 70 percent / PCC View Scheme

9-tetradecyn-1-ol (60037-69-6) → (Z)-9-hexadecenal (56219-04-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: 86 percent / H2 / P2Ni 2: 70 percent / PCC View Scheme

9-decyn-1-ol (17643-36-6) → (Z)-9-hexadecenal (56219-04-6)

Conditions	Yield
Multi-step reaction with 5 steps 1: 85 percent / p-TsOH / CH2Cl2 / Ambient temperature 2: LiNH2 / liquid ammonia 3: p-TsOH / methanol 4: 86 percent / H2 / P2Ni 5: 70 percent / PCC View Scheme

(Z)-9-hexadecenal (56219-04-6) → cis-9-hexadecenoic acid (373-49-9)

Conditions	Yield
With sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene In tetrahydrofuran; water; tert-butyl alcohol at 20℃;	95%

(Z)-9-hexadecenal (56219-04-6) + methyl (triphenylphosphoranylidene)acetate (21204-67-1) → methyl (2E,11Z)-octadeca-2,11-dienoate

Conditions	Yield
In dichloromethane at 20℃;	90%

(Z)-9-hexadecenal (56219-04-6) → methyl (2E,11Z)-octadeca-2,11-dienoate

Conditions	Yield
With methyl (triphenylphosphoranylidene)acetate In dichloromethane at 20℃;	90%

(Z)-9-hexadecenal (56219-04-6) + methylmagnesium chloride (676-58-4) → C17H34O

Conditions	Yield
In diethyl ether at 0 - 10℃;

Upstream product

• 10378-01-5 palmitoleyl alcohol 
• 2695-48-9 8-Bromo-1-octene 
• 197901-27-2 hexadec-1-en-9-yne 
• 50816-20-1 2-(8-bromooctyloxy)tetrahydropyran 
• 50816-19-8 8-bromooctanol 
• 19754-58-6 2-dec-9-ynyloxy-tetrahydro-pyran 
• 111-66-0 oct-1-ene 
• 25601-41-6 methyl 9-decenoate 
• 99159-88-3 2-[((Z)-Hexadec-9-enyl)oxy]-tetrahydro-pyran 
• 629-41-4 1,8-Octanediol 
• 114157-22-1 9-(tert-butyl-dimethyl-silanyloxy)-1-nonanal 
• 157730-99-9 9-(tert-butyldimethylsilanyloxy)-1-nonanol 
• 3937-56-2 1,9-Nonanediol 
• 19754-59-7 tetrahydro-2-(9-tetradecynyloxy)pyran 

Downstream Products

• 373-49-9 cis-9-hexadecenoic acid 
• 40426-22-0 ( Z )-hexadec-9-enoyl chloride 

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