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Name	(Z)-9-Hexadecenal	EINECS	N/A
CAS No.	56219-04-6	Density	0.84g/cm³
PSA	17.07000	LogP	5.44260
Solubility	N/A	Melting Point	N/A
Formula	C16H30 O	Boiling Point	330.9°Cat760mmHg
Molecular Weight	238.414	Flash Point	161.5°C
Transport Information	N/A	Appearance	N/A
Safety	Low toxicity by ingestion. When heated to decomposition it emits acrid smoke and irritating vapors.	Risk Codes	R36/37/38
Molecular Structure		Hazard Symbols	Low toxicity by ingestion.
Synonyms	9-Hexadecenal,(Z)-; Palmitolealdehyde (6CI); (Z)-9-Hexadecenal; cis-9-Hexadecenal	Article Data	13

(Z)-9-Hexadecenal Synthetic route

: 10378-01-5
palmitoleyl alcohol

: 56219-04-6
(Z)-9-hexadecenal

Conditions

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%

: 21676-07-3
(Z)-4-undecene-1-ol

: 56219-04-6
(Z)-9-hexadecenal

Conditions

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

: 68820-32-6
(Z)-4-undecenal

: 56219-04-6
(Z)-9-hexadecenal

Conditions

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

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

: 109523-23-1
(Z)-4-undecenyl bromide

: 56219-04-6
(Z)-9-hexadecenal

Conditions

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

: 82861-01-6
1,1-dimethoxy-8-tosyloxy-(4Z)-octene

: 56219-04-6
(Z)-9-hexadecenal

Conditions

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

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

: 104187-94-2
1,1-dimethoxy-(4Z)-undecene

: 56219-04-6
(Z)-9-hexadecenal

Conditions

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

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

: 56219-04-6
(Z)-9-hexadecenal

Conditions

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

: 56219-04-6
(Z)-9-hexadecenal

Conditions

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

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

: 1120-25-8
(Z)-9-hexadecenoic acid methyl ester

: 56219-04-6
(Z)-9-hexadecenal

Conditions

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;

: 1931-63-1
methyl ester of azelaic acid aldehyde

: 56219-04-6
(Z)-9-hexadecenal

Conditions

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

(Z)-9-Hexadecenal Chemical Properties

IUPAC Name: (Z)-Hexadec-9-enal
Synonyms: 9-Hexadecenal, (Z)- ; cis-9-Hexadecenal ; (Z)-9-Hexadecenal ; (Z)-Hexadec-9-enal ; 9-Hexadecenal, (9Z)-
CAS NO: 56219-04-6
Molecular Formula of (Z)-9-Hexadecenal (CAS NO.56219-04-6) :C₁₆H₃₀O
Molecular Weight of (Z)-9-Hexadecenal (CAS NO.56219-04-6) :238.4088
Molecular structure of (Z)-9-Hexadecenal (CAS NO.56219-04-6) :
EINECS: 260-064-2
Index of Refraction: 1.451
Surface Tension: 30.2 dyne/cm
Density: 0.84 g/cm³
Flash Point: 161.5 °C
Enthalpy of Vaporization: 57.36 kJ/mol
Boiling Point: 330.9 °C at 760 mmHg
Vapour Pressure: 0.000161 mmHg at 25°C
Storage temp. −20°C

(Z)-9-Hexadecenal Toxicity Data With Reference

orl-rat LD50:>5000 mg/kg

HBPTO* Handbook of pesticide toxicology. 1 (2001),142.

(Z)-9-Hexadecenal Safety Profile

Low toxicity by ingestion. When heated to decomposition it emits acrid smoke and irritating vapors.
Hazard Codes Irritant Xi
Risk Statements 36/37/38
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements 26-36
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36:Wear suitable protective clothing.
WGK Germany 3

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