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Name	Oleylamine	EINECS	204-015-5
CAS No.	112-90-3	Density	0.828 g/cm³
PSA	26.02000	LogP	6.68290
Solubility	Insoluble in water	Melting Point	18-26 °C(lit.)
Formula	C₁₈H₃₇N	Boiling Point	364.4 °C at 760 mmHg
Molecular Weight	267.498	Flash Point	154.4 °C
Transport Information	UN 2735 8/PG 2	Appearance	beige paste or powder
Safety	26-36/37/39-45-24/25	Risk Codes	34-22-50/53
Molecular Structure		Hazard Symbols	C, N
Synonyms	Armeen O;ArmeenOD;Armeen OLD-C;Arosurf AA 60;Corsamine POD-V;Genamin OL 100D;Kemamine P989;Kemamine P 989D;Noram O;Noram OD;Oleamine;Oleinamine;9-Octadecen-1-amine,(9Z)-;SK-FLOT;cis-9-Octadecenylamine;90015-00-2;9-Octadecen-1-amine,(Z)-;9-Octadecenylamine, (Z)- (8CI);((Z)-9-Octadecenyl)amine;9-(Z)-Octadecen-1-amine;Adogen 172D;Alamine 11;Amine OB;	Article Data	24

Oleylamine Synthetic route

: 301-02-0
cis-9-octadecenoamide

: 112-90-3
(Z)-9-octadecen-1-amine

Conditions

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran Reflux;	95%
With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; Reflux;	95%
With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; Reflux;	95%
Stage #1: cis-9-octadecenoamide With lithium aluminium tetrahydride In tetrahydrofuran at 50 - 60℃; for 3.5 - 6.75h; Stage #2: With sodium hydroxide; water In tetrahydrofuran at 40℃; for 1 - 2h; Product distribution / selectivity;

: 61041-55-2
oleonitrile

: 112-90-3
(Z)-9-octadecen-1-amine

Conditions

Conditions	Yield
With sodium; toluene; butan-1-ol

N-oleyl-phthalimide: N-oleyl-phthalimide

: 112-90-3
(Z)-9-octadecen-1-amine

Conditions

Conditions	Yield
With potassium hydroxide

oilacidic-nitrile: oilacidic-nitrile

: 112-90-3
(Z)-9-octadecen-1-amine

Conditions

Conditions	Yield
With sodium hydroxide; nickel at 60℃; Hydrogenation;

oleic acid nitrile: oleic acid nitrile

: 112-90-3
(Z)-9-octadecen-1-amine

Conditions

Conditions	Yield
With ammonia; cobalt at 80 - 100℃; under 73550.8 - 147102 Torr; Hydrogenation;
With ammonia; cobalt at 80 - 100℃; under 73550.8 - 147102 Torr; Hydrogenation;

: 143-28-2
oleoyl alcohol

A: 112-90-3
(Z)-9-octadecen-1-amine

B dioleylamine and trioleylamine: dioleylamine and trioleylamine

Conditions

Conditions	Yield
With silica-alumina; ammonia at 360℃;

: 41130-29-4
oleylamine hydrochloride

: 112-90-3
(Z)-9-octadecen-1-amine

Conditions

Conditions	Yield
With sodium hydroxide In tert-butyl methyl ether; water at 15 - 25℃; for 1.25 - 1.5h; Product distribution / selectivity;

: 112-91-4
cis-9-octadecenenitrile

: 112-90-3
(Z)-9-octadecen-1-amine

Conditions

Conditions	Yield
With ammonia; hydrogen; Ni-doped silica; para-methylbenzamide at 140℃; under 26252.6 Torr; for 3.5h; Product distribution / selectivity;
With ammonia; hydrogen; Ni-doped silica; benzamide at 140℃; under 26252.6 Torr; for 3.5h; Product distribution / selectivity;
With ammonia; hydrogen; Ni-doped silica; cis-9-octadecenoamide at 140℃; under 26252.6 Torr; for 3.5h; Product distribution / selectivity;
With ammonia; hydrogen; Ni-doped silica at 140℃; under 26252.6 Torr; for 3.5h; Product distribution / selectivity;

: 112-80-1
cis-Octadecenoic acid

: 112-90-3
(Z)-9-octadecen-1-amine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: oxalyl dichloride / dichloromethane / 4 h / 0 - 20 °C 2: ammonia / dichloromethane; water / 0.5 h / 0 °C 3: lithium aluminium tetrahydride / tetrahydrofuran / Reflux View Scheme
With D-glucose; pyridoxal 5'-phosphate; glucose dehydrogenase (CDX-901) from Codexis; NADP; isopropylamine; magnesium chloride In n-heptane; dimethyl sulfoxide at 30℃; for 20h; pH=8; Green chemistry; Enzymatic reaction;

: 112-77-6
(Z)-9-octadecenoyl chloride

: 112-90-3
(Z)-9-octadecen-1-amine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: ammonia / dichloromethane; water / 0.5 h / 0 °C 2: lithium aluminium tetrahydride / tetrahydrofuran / Reflux View Scheme
Multi-step reaction with 2 steps 1: ammonium hydroxide / tetrahydrofuran / 0 - 20 °C 2: lithium aluminium tetrahydride / tetrahydrofuran / 0 °C / Reflux View Scheme
Multi-step reaction with 2 steps 1: ammonium hydroxide / tetrahydrofuran / 3 h / 0 - 20 °C 2: lithium aluminium tetrahydride / tetrahydrofuran / 0 °C / Reflux View Scheme

Oleylamine Chemical Properties

IUPAC Name: (Z)-Octadec-9-en-1-amine
Following is the structure of Oleylamine (CAS NO.112-90-3):

Molecular Formula: C₁₈H₃₇N
Molecular Weight: 267.49
EINECS: 204-015-5
Index of Refraction: 1.463
Molar Refractivity: 89.03 cm³
Molar Volume: 322.9 cm³
Density: 0.828 g/cm³
Flash Point: 154.4 °C
Melting point: 18-26 °C(lit.)
Surface Tension: 31.4 dyne/cm
Enthalpy of Vaporization: 61.05 kJ/mol
Boiling Point: 364.4 °C at 760 mmHg
Vapour Pressure: 1.69E-05 mmHg at 25 °C
Water Solubility of Oleylamine (CAS NO.112-90-3): insoluble
Appearance of Oleylamine (CAS NO.112-90-3): beige paste or powder
Canonical SMILES: CCCCCCCCC=CCCCCCCCCN
Isomeric SMILES: CCCCCCCC/C=C\CCCCCCCCN
InChI: InChI=1S/C18H37N/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19/h9-10H,2-8,11-19H2,1H3/b10-9-
InChIKey: QGLWBTPVKHMVHM-KTKRTIGZSA-N

Oleylamine Uses

Oleylamine (CAS NO.112-90-3) is commonly used as organic intermediates and fabric assistant agent.

Oleylamine Toxicity Data With Reference

1.	orl-mus TDLo:800 mg/kg (9D preg):REP	DZZEA7 Deutsche Zahnaerztliche Zeitschrift. 32 (1977),861.
2.	ipr-mus TDLo:400 mg/kg (9D preg):TER	DZZEA7 Deutsche Zahnaerztliche Zeitschrift. 32 (1977),861.
3.	ipr-mus LD50:888 mg/kg	DZZEA7 Deutsche Zahnaerztliche Zeitschrift. 35 (1980),1070.

Oleylamine (CAS NO.112-90-3) hasn't been listed as a carcinogen by ACGIH, IARC, NTP, or CA Prop 65. And the toxicological properties have not been fully investigated. You can see actual entry in RTECS for complete information.

Oleylamine Consensus Reports

Reported in EPA TSCA Inventory.

Oleylamine Safety Profile

Moderately toxic by intraperitoneal route. An experimental teratogen. Experimental reproductive effects. When heated to decomposition it emits toxic fumes of NO_x.
Hazard Codes: Corrosive C, Dangerous N
Risk Statements: 34-22-50/53
R34:Causes burns.
R22:Harmful if swallowed.
R50/53:Very toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment.
Safety Statements: 26-36/37/39-45-24/25
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection.
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
S24/25:Avoid contact with skin and eyes.
RIDADR: UN 2735 8/PG 2
WGK Germany: 2
RTECS: RG4130000
HazardClass: 8
PackingGroup: III

Oleylamine Specification

Oleylamine , its cas register number 112-90-3. It also can be called 1-Amino-9-octadecene; cis-9-Octadecenylamine ; 9-octadecen-1-amine, (9Z)- ; (Z)-9-Octadecen-1-amine ; 9-Octadecen-1-amine, (Z)- ; 9-Octadecenylamine, (Z)- ; Alamine 11 ; Armeen O ; Kemamine P 989 ; and Noram O . Its classification code is Reproductive Effect.
Oleylamine (CAS NO.112-90-3) could be stable under normal temperatures and pressures. It should avoid the condition like incompatible materials. It is not compatible with strong oxidizing agents. And also prevent it to broken down into hazardous decomposition products: Nitrogen oxides, carbon monoxide, carbon dioxide, nitrogen. However, its hazardous polymerization has not been reported.

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