• Name

  oleonitrile

• EINECS
• CAS No. 112-91-4
• Article Data28
• CAS DataBase
• Density 0.842g/cm³
• Solubility
• Melting Point -1°C
• Formula C18H33 N
• Boiling Point 385.6°Cat760mmHg
• Molecular Weight 263.467
• Flash Point 191.1°C
• Transport Information
• Appearance
• Safety Low toxicity by ingestion and intraperitoneal routes. When heated to decomposition it emits toxic vapors of NO_x.
• Risk Codes
• Molecular Structure
• Hazard Symbols
• Synonyms 9-Octadecenenitrile,(Z)-; Oleonitrile (6CI,7CI,8CI); Arneel O; Oleic acid nitrile; Oleic nitrile;Oleoylnitrile; Oleyl nitrile; Oleylonitrile
• PSA 23.79000
• LogP 6.54748

Synthetic route

301-02-0

cis-9-octadecenoamide

112-91-4

cis-9-octadecenenitrile

Conditions

Conditions	Yield
With phosphorus pentoxide at 150℃; for 8h;	95%
With thionyl chloride at 80℃; for 4h;	60%
With Ketene at 420℃; ueber Glasringe;

24225-08-9

methanesulfonyl cyanide

119520-40-0

(Z)-Octadec-9-enoic acid 2-thioxo-2H-pyridin-1-yl ester

112-91-4

cis-9-octadecenenitrile

Conditions

Conditions	Yield
In dichloromethane at 0℃; Irradiation;	95%
In dichloromethane at 0℃; Irradiation;	87%

19158-51-1

P-toluenesulfonyl cyanide

119520-40-0

(Z)-Octadec-9-enoic acid 2-thioxo-2H-pyridin-1-yl ester

112-91-4

cis-9-octadecenenitrile

Conditions

Conditions	Yield
In dichloromethane at 0℃; Irradiation;	95%
In dichloromethane at 0℃; Irradiation;	87 % Spectr.

112-80-1

cis-Octadecenoic acid

112-91-4

cis-9-octadecenenitrile

Conditions

Conditions	Yield
With sodium azide; triethylamine; triphenylphosphine; (bis-(2-methoxyethyl)amino)sulfur trufluoride In dichloromethane; dimethyl sulfoxide at 0 - 20℃; for 0.5h;	90%
With ammonia; cobalt(II) oleate at 270℃;
With aluminum oxide; ammonia at 290℃;

112-90-3

(Z)-9-octadecen-1-amine

112-91-4

cis-9-octadecenenitrile

Conditions

Conditions	Yield
With Ru(at)UiO-66(Ce-(1,4-benzendicarboxylate)) In water at 130℃; for 16h; Inert atmosphere;	86%
With [Ru(p-cymene)(pzH-NP)(Cl)]Cl; potassium tert-butylate In toluene at 70℃; for 24h; Schlenk technique; Inert atmosphere;	72%
With [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2 In 1,2-dichloro-benzene at 110℃; for 24h; Inert atmosphere; Schlenk technique;	67%
With C26H36ClN2RuS(1+)*F6P(1-) In 1,2-dichloro-benzene at 110℃; for 24h; Inert atmosphere; Schlenk technique;	60%
With [Ru(η6-cymene)([2,6-iPr2-(C6H3)NH]-PPh2)Cl2] In neat (no solvent) at 100℃; for 10h; Molecular sieve;

17364-07-7, 22147-34-8, 112-11-8

isopropyl oleate

112-91-4

cis-9-octadecenenitrile

Conditions

Conditions	Yield
Stage #1: isopropyl oleate With diisobutylaluminium hydride In hexane; dichloromethane at -78℃; for 3h; Inert atmosphere; Stage #2: With ammonia; iodine In tetrahydrofuran; hexane; dichloromethane; water at -78 - 20℃; Inert atmosphere;	76%

111-62-6

oleic acid ethyl ester

112-91-4

cis-9-octadecenenitrile

Conditions

Conditions	Yield
Stage #1: oleic acid ethyl ester With sodium diisobutyl-tert-butoxyaluminium hydride In tetrahydrofuran at 0℃; for 2h; Inert atmosphere; Stage #2: With 1,3-Diiodo-5,5-dimethyl-2,4-imidazolidinedione; ammonia In tetrahydrofuran; water at 0 - 20℃; for 3h;	75%
Stage #1: oleic acid ethyl ester With sodium diisobutyl-tert-butoxyaluminium hydride In tetrahydrofuran at 0℃; for 4h; Inert atmosphere; Stage #2: With ammonium hydroxide; 1,3-Diiodo-5,5-dimethyl-2,4-imidazolidinedione In tetrahydrofuran at 0℃; for 2h; Inert atmosphere;	385 mg

112-62-9

Methyl oleate

112-91-4

cis-9-octadecenenitrile

Conditions

Conditions	Yield
With ammonia; hydrogen; silica gel at 370℃;

112-80-1

cis-Octadecenoic acid

57-13-6

urea

112-91-4

cis-9-octadecenenitrile

Conditions

Conditions	Yield
at 285 - 300℃;

3999-01-7

linoleamide

112-91-4

cis-9-octadecenenitrile

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 95 percent / NH3(gas) / CH2Cl2 / 1 h / Ambient temperature 2: 95 percent / P2O5 / 8 h / 150 °C View Scheme

60-33-3

linoleic acid

112-91-4

cis-9-octadecenenitrile

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: (COCl)2, DMF / benzene / 3 h / Ambient temperature 2: 95 percent / NH3(gas) / CH2Cl2 / 1 h / Ambient temperature 3: 95 percent / NH3(gas) / CH2Cl2 / 1 h / Ambient temperature 4: 95 percent / P2O5 / 8 h / 150 °C View Scheme

7459-33-8

linoleyl chloride

112-91-4

cis-9-octadecenenitrile

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 95 percent / NH3(gas) / CH2Cl2 / 1 h / Ambient temperature 2: 95 percent / NH3(gas) / CH2Cl2 / 1 h / Ambient temperature 3: 95 percent / P2O5 / 8 h / 150 °C View Scheme

112-91-4

cis-9-octadecenenitrile

(8Z)-5-heptadec-8-enyl-1H-tetrazole

Conditions

Conditions	Yield
With sodium azide; triethylamine hydrochloride In toluene Heating;	94%

112-91-4

cis-9-octadecenenitrile

sulfur

sulfur

hydrogen

hydrogen

cobalt polysulfidene

cobalt polysulfidene

31494-22-1

cis-octadec-9-enethiol

Conditions

Conditions	Yield
at 150 - 175℃; unter Druck;

...Expand

112-91-4

cis-9-octadecenenitrile

aq.-ethanolic semicarbazide

aq.-ethanolic semicarbazide

Raney nickel

Raney nickel

octadec-9c-enal semicarbazone

Conditions

Conditions	Yield
Hydrogenation;

...Expand

112-91-4

cis-9-octadecenenitrile

Cr2O3-H2SO4

Cr2O3-H2SO4

A

112-05-0

nonanoic acid

B

azelaic acid mononitrile

azelaic acid mononitrile

...Expand

112-91-4

cis-9-octadecenenitrile

67-64-1

acetone

KMnO4

KMnO4

A

112-05-0

nonanoic acid

B

azelaic acid mononitrile

azelaic acid mononitrile

...Expand

112-91-4

cis-9-octadecenenitrile

(8Z)-2-(heptadec-8-enyl)-5-methyl-1,3,4-oxadiazole

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 94 percent / sodium azide; triethylamine hydrochloride / toluene / Heating 2: 73 percent / 7 h / Heating View Scheme

112-91-4

cis-9-octadecenenitrile

2566-91-8

epoxidized methyl oleate

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 10.0 g / 1) 24 h in freezer; 2) ether, 24 h in refrigerator 2: 6.54 g / diethyl ether / 24 h / Heating 3: H2O2, amide (20) / tetrahydrofuran / 24 h / Ambient temperature; competition experiment with amide (20); intermolecular oxidation View Scheme

112-91-4

cis-9-octadecenenitrile

74658-71-2

trimethyl orthooleate

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 10.0 g / 1) 24 h in freezer; 2) ether, 24 h in refrigerator 2: 6.54 g / diethyl ether / 24 h / Heating View Scheme

101-02-0

triphenyl phosphite

112-91-4

cis-9-octadecenenitrile

carbon monoxidehydrogen

carbon monoxidehydrogen

378784-00-0, 7440-16-6

rhodium

formyloctadecanonitrile

...Expand

9-OCTADECENENITRILE, (Z)- Chemical Properties

9-OCTADECENENITRILE, (Z)- Toxicity Data With Reference

9-OCTADECENENITRILE, (Z)- Consensus Reports

9-OCTADECENENITRILE, (Z)- Safety Profile

9-OCTADECENENITRILE, (Z)- Specification