112-90-3

Basic information

• Product Name: Oleylamine
• Synonyms: OLEYLAMINE;(z)-9-octadecen-1-amin;(Z)-9-Octadecen-1-amine;(z)-9-octadecenylamin;(z)-octadec-9-enylamine;9-octadecenylamine(oda);alamine11;armeeno
• CAS NO: 112-90-3
• Molecular Formula: C₁₈H₃₇N
• Molecular Weight: 267.49
• EINECS: 204-015-5
• Product Categories: Cosmetic raw materials
• Mol File: 112-90-3.mol
• Article Data: 17

Chemical Properties

• Melting Point: 18-26 °C(lit.)
• Boiling Point: 348-350 °C(lit.)
• Flash Point: 310 °F
• Appearance: colorless/liquid
• Density: 0.813 g/mL at 25 °C(lit.)
• Vapor Pressure: 8 mm Hg ( 135 °C)
• Refractive Index: n20/D 1.4596(lit.)
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: 10.67±0.10(Predicted)
• Water Solubility: insoluble
• Stability: Stable. Incompatible with acids, acid chlorides, acid anhydrides, oxidizing agents.
• BRN: 1723960
• CAS DataBase Reference: Oleylamine(CAS DataBase Reference)
• NIST Chemistry Reference: Oleylamine(112-90-3)
• EPA Substance Registry System: Oleylamine(112-90-3)

Safety Data

• Hazard Codes: C,N
• Statements: 34-22-50/53
• Safety Statements: 26-36/37/39-45-24/25
• RIDADR: UN 2735 8/PG 2
• WGK Germany: 2
• RTECS: RG4130000
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 112-90-3(Hazardous Substances Data)

Usage

Description

Oleylamine (OAm) is a long-chain primary alkylamine that acts as an electron donor at elevated temperatures. It exhibits affinity to metals through its NH2 functional groups and is known for its strong reducing and stabilizing properties in the synthesis of nanoparticles. Oleylamine is typically found as a beige paste or powder and has a boiling point of 364 °C.

Uses

Used in the Chemical Synthesis Industry:
Oleylamine is used as a reducing agent and stabilizer for the synthesis of metallic nanostructures, including Au, Ag, Pt, Pd, and their alloys. Its high boiling point allows for the synthesis of these nanostructures at high temperatures, providing a versatile and efficient method for producing various metallic nanoparticles.
Used in the Electronics Industry:
As an anti-static agent, oleylamine is used to prevent the accumulation of static electricity on surfaces, which is crucial in the manufacturing and handling of electronic components and devices.
Used in the Pharmaceutical Industry:
Oleylamine is used in the chemical synthesis and capping of nanoparticles such as Fe3O4, poly (2-hydroxyethyl methacrylate)-graft-poly (ε-caprolactone), titania, and mesoporous silica. These nanoparticles have potential applications in drug delivery, imaging, and diagnostics.

Safety Profile

Moderately toxic by intraperitoneal route. An experimental teratogen. Experimental reproductive effects. When heated to decomposition it emits toxic fumes of NOx. See also AMINES.

InChI:InChI=1/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-

Synthetic route

cis-9-octadecenoamide (301-02-0) → (Z)-9-octadecen-1-amine (112-90-3)

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;

oleonitrile (61041-55-2) → (Z)-9-octadecen-1-amine (112-90-3)

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

N-oleyl-phthalimide → (Z)-9-octadecen-1-amine (112-90-3)

Conditions	Yield
With potassium hydroxide

oilacidic-nitrile → (Z)-9-octadecen-1-amine (112-90-3)

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

oleic acid nitrile → (Z)-9-octadecen-1-amine (112-90-3)

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;

oleoyl alcohol (143-28-2) → (Z)-9-octadecen-1-amine (112-90-3) + dioleylamine and trioleylamine

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

oleylamine hydrochloride (41130-29-4) → (Z)-9-octadecen-1-amine (112-90-3)

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

cis-9-octadecenenitrile (112-91-4) → (Z)-9-octadecen-1-amine (112-90-3)

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;

cis-Octadecenoic acid (112-80-1) → (Z)-9-octadecen-1-amine (112-90-3)

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;

(Z)-9-octadecenoyl chloride (112-77-6) → (Z)-9-octadecen-1-amine (112-90-3)

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

oleyl methanesulfonate (35709-09-2) → (Z)-9-octadecen-1-amine (112-90-3)

Conditions	Yield
With ammonia In methanol at 130℃; for 3h; Microwave irradiation;

(Z)-9-octadecen-1-amine (112-90-3) + 2-chloro-3-methyl-1-oxa-3-aza-2-phosphacyclopentane 2-oxide (66046-61-5) → 3-methyl-2-oleylamino-1,3,2-oxazaphosphacyclopentane 2-oxide

Conditions	Yield
With triethylamine In dichloromethane for 17h; Ambient temperature;	100%
With triethylamine In dichloromethane

(Z)-9-octadecen-1-amine (112-90-3) + acryloyl chloride (814-68-6) → 2-acryloylamido-olean (23586-43-8)

Conditions	Yield
With triethylamine In dichloromethane at -10 - 0℃; for 4.33333h;	100%
With triethylamine In dichloromethane

(Z)-9-octadecen-1-amine (112-90-3) + 3-devinyl-31-methoxymethyl-132-demethoxycarbonylpheophorbide-a → C51H71N5O3

Conditions	Yield
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 1h; Inert atmosphere;	100%
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; Sealed tube;

(Z)-9-octadecen-1-amine (112-90-3) + pyropheophorbide a (24533-72-0) → C51H69N5O2

Conditions	Yield
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 1h; Inert atmosphere;	100%
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; Sealed tube;

(Z)-9-octadecen-1-amine (112-90-3) + 4-[4-(1-hydroxyethyl)-2-methoxy-5-nitrophenoxy]butanoic acid (175281-76-2) → C31H52N2O6 (1356856-98-8)

Conditions	Yield
With benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide In tetrahydrofuran at 20℃; for 48h;	99%

(Z)-9-octadecen-1-amine (112-90-3) + trifluoroacetic anhydride (407-25-0) → (Z)-2,2,2-trifluoro-N-(octadec-9-en-1-yl)acetamide (79779-29-6)

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃; for 12h; Inert atmosphere;	98%
With triethylamine In dichloromethane at 20℃; for 12h; Inert atmosphere; Cooling with ice;	66%

(Z)-9-octadecen-1-amine (112-90-3) + acrylic acid methyl ester (292638-85-8) → 3-[(2-methoxycarbonylethyl)oleylamino]propionic acid methyl ester

Conditions	Yield
In methanol at 20℃; for 24h; Inert atmosphere;	97%
In methanol at 20℃; for 72h;

(Z)-9-octadecen-1-amine (112-90-3) + 2,6-dimethylphenylisothiocyanate (19241-16-8) → 1-(2,6-Dimethyl-phenyl)-3-((Z)-octadec-9-enyl)-thiourea

Conditions	Yield
With triethylamine In ethyl acetate	96%

(Z)-9-octadecen-1-amine (112-90-3) + benzaldehyde (100-52-7) → N-(benzylidene)oleylimine (260396-55-2)

Conditions	Yield
With 3 A molecular sieve In dichloromethane at 40℃; for 6h; Condensation;	96%
In methanol for 4h; Reflux;	82%

(Z)-9-octadecen-1-amine (112-90-3) + phenyl isothiocyanate (103-72-0) → (Z)-1-(octadec-9-enyl)-3-phenylthiourea

Conditions	Yield
In toluene at 20℃; for 2h;	96%

(Z)-9-octadecen-1-amine (112-90-3) + 4-phenyl-4-vinyl-1,3-dioxolan -2-one (1459246-62-8) → 2-hydroxy-2-phenylbut-3-en-1-yl oleylcarbamate

Conditions	Yield
With 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine In neat (no solvent) at 20℃; for 6h; regioselective reaction;	92%

(Z)-9-octadecen-1-amine (112-90-3) + Phosphorous Acid Tris(3,5-dimethylpyrazolide) (54877-56-4) → 3,5-dimethyl-1H-pyrazole (67-51-6) + tris oleylaminophosphine

Conditions	Yield
at 80℃; for 0.5h; Temperature;	A 92% B n/a

(Z)-9-octadecen-1-amine (112-90-3) + 3-chloropropylmethyldimethoxysilane (18171-19-2) → C30H65NO4Si2*ClH

Conditions	Yield
With sodium 4-dodecylbenzenesulfonate In hexane at 60℃; for 4h;	91.7%

nickel(II) bromide dimethoxyethane (28923-39-9) + (Z)-9-octadecen-1-amine (112-90-3) → nickel(II) bis(oleylamide)

Conditions	Yield
Stage #1: (Z)-9-octadecen-1-amine With n-butyllithium In pentane at 20℃; for 3h; Schlenk technique; Inert atmosphere; Cooling with ice; Stage #2: nickel(II) bromide dimethoxyethane In toluene at 20℃; Schlenk technique; Inert atmosphere;	91%

(Z)-9-octadecen-1-amine (112-90-3) + (R)-Pantolacton (599-04-2) → (2R)-2,4-Dihydroxy-3,3-dimethyl-N-oleylbutanamid (117801-03-3)

Conditions	Yield
at 115℃; for 3h;	90%

(Z)-9-octadecen-1-amine (112-90-3) + 1-(2'-deoxy-5'-O-dimethoxytrityl-β-D-ribofuranosyl)-5-methyl-4-(1,2,4-triazol-1-yl)-2-pyrimidone (360048-15-3) → 2'-deoxy-5'-O-dimethoxytrityl-5-methyl-N4-oleylcytidine

Conditions	Yield
In 1,4-dioxane at 20℃; for 1h;	90%

(Z)-9-octadecen-1-amine (112-90-3) + ethyl 5-(4-chlorophenyl)-1-phenyl-1H-pyrazole-3-carboxylate (1082746-74-4) → N-(1-oleyl)-5-(4-chlorophenyl)-1-phenyl-1H-pyrazole-3-carboxamide (1082746-76-6)

Conditions	Yield
Stage #1: (Z)-9-octadecen-1-amine With trimethylaluminum In n-heptane; dichloromethane at 20℃; for 1.08333h; Stage #2: ethyl 5-(4-chlorophenyl)-1-phenyl-1H-pyrazole-3-carboxylate In n-heptane; dichloromethane for 24h;	90%

(Z)-9-octadecen-1-amine (112-90-3) + perylene-3,4,9,10-tetracarboxylic acid 3,4:9,10-dianhydride (128-69-8) → N,N'-di((Z)-9-octadecene)-3,4,9,10-perylene tetracarboxylic diimide (1017242-09-9)

Conditions	Yield
In ethylene glycol	90%

(Z)-9-octadecen-1-amine (112-90-3) + N-(1,6-dihydro-4-methyl-6-oxo-2-pyrimidinyl)-1H-imidazole-1-carboxamide (561316-60-7) → 1-(6-methyl-4-oxo-1,4-dihydropyrimidin-2-yl)-3-octadec-9-enylurea (1313595-52-6)

Conditions	Yield
In dichloromethane for 6h; Reflux;	90%

(Z)-9-octadecenoyl chloride (112-77-6) + (Z)-9-octadecen-1-amine (112-90-3) → (9Z)-N-[(9Z)-9-octadecen-1-yl]-9-octadecenamide

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃; for 21h;	90%

(Z)-9-octadecen-1-amine (112-90-3) + N-(4-isothiocyanatomethylphenyl)methanesulfonamide (401573-42-0) → N-{4-[(3-octadec-9-enyl-thioureido)-methyl]-phenyl}-methanesulfonamide

Conditions	Yield
In dichloromethane at 20℃;	88%

(Z)-9-octadecen-1-amine (112-90-3) + cis-Octadecenoic acid (112-80-1) → (9Z)-N-[(9Z)-9-octadecen-1-yl]-9-octadecenamide

Conditions	Yield
With ethanol at 160℃; for 6h; Temperature; Reagent/catalyst; Concentration; Time; Autoclave; Green chemistry;	88%
With 4-(dimethylamino)pyridinium tosylate; diisopropyl-carbodiimide In dichloromethane at 20℃; for 5h;	70%

(Z)-9-octadecen-1-amine (112-90-3) + ethyl 1,5-bis(4-chlorophenyl)-1H-pyrazole-3-carboxylate (1082746-75-5) → N-(1-oleyl)-1,5-bis(4-chlorophenyl)-1H-pyrazole-3-carboxamide (1082746-77-7)

Conditions	Yield
Stage #1: (Z)-9-octadecen-1-amine With trimethylaluminum In n-heptane; dichloromethane at 20℃; for 1.08333h; Stage #2: ethyl 1,5-bis(4-chlorophenyl)-1H-pyrazole-3-carboxylate In n-heptane; dichloromethane for 20h;	88%

(Z)-9-octadecen-1-amine (112-90-3) + salicylaldehyde (90-02-8) → C25H41NO

Conditions	Yield
In methanol for 4h; Reflux;	88%

(Z)-9-octadecen-1-amine (112-90-3) + Boc-Glu (2419-94-5) → C46H87N3O4

Conditions	Yield
With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 48h; Inert atmosphere; Cooling with ice;	88%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 24.5h; Inert atmosphere; Cooling with ice;

(Z)-9-octadecen-1-amine (112-90-3) + cadmium(II) acetate dihydrate (5743-04-4) + thiourea (17356-08-0) → [(CdSe)13(oleylamine)13]

Conditions	Yield
Stage #1: (Z)-9-octadecen-1-amine; cadmium(II) acetate dihydrate at 70℃; for 1h; Inert atmosphere; Schlenk technique; Stage #2: thiourea at 20℃; for 68h; Inert atmosphere; Schlenk technique;	86.6%

(Z)-9-octadecen-1-amine (112-90-3) → cis-9-octadecenenitrile (112-91-4)

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;

2-methyl-4-oxo-3,1-benzoxazine (525-76-8) + (Z)-9-octadecen-1-amine (112-90-3) → (Z)-2-methyl-3-(octadec-9-en-1-yl)quinazolin-4(3H)-one

Conditions	Yield
Stage #1: 2-methyl-4-oxo-3,1-benzoxazine In ethanol at 20℃; for 0.0833333h; Stage #2: (Z)-9-octadecen-1-amine In ethanol at 100℃; for 6h;	85.65%

(Z)-9-octadecen-1-amine (112-90-3) + steviolbioside (41093-60-1) → steviolbioside oleylamide

Conditions	Yield
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 12h;	85%

Upstream product

• 35709-09-2 oleyl methanesulfonate 
• 4303-70-2 (E)-9-octadecenoic acid amide 
• 19491-41-9 elaidonitrile 
• 112-77-6 elaidoyl chloride 
• 112-79-8 Elaidic acid 
• 921620-98-6 elaidylamine hydrochloride 
• 122-32-7 trioleoylglycerol 
• 112-77-6 (Z)-9-octadecenoyl chloride 
• 112-80-1 cis-Octadecenoic acid 
• 112-91-4 cis-9-octadecenenitrile 
• 41130-29-4 oleylamine hydrochloride 
• 301-02-0 cis-9-octadecenoamide 
• 143-28-2 oleoyl alcohol 
• 61041-55-2 oleonitrile 

Downstream Products

• 20073-91-0 N-(9-Octadecenyl)-2-pyrrolidon 
• 135627-22-4 (Z)-2-(9-Octadecenylamino)-N-(2,4,6-trimethoxyphenyl)acetamide 
• 135627-23-5 (Z)-N-(2,6-Dimethylphenyl)-2-(9-octadecenylamino)acetamide 
• 41130-29-4 oleylamine hydrochloride 
• 4617-33-8 15-hydroxylpentadecanoic acid 
• 1220909-15-8 N-oleyl-15-hydroxypentadecanoylamine 
• 506-13-8 16-hydroxyhexadecanoic acid 
• 1220909-16-9 N-oleyl-16-hydroxyhexadecanoylamine 
• 1450603-58-3 (Z)-1-(octadec-9-en-1-yl)-3-benzylurea 
• 1450603-59-4 (Z)-1-(octadec-9-en-1-yl)-3-(3-methoxybenzyl)urea 
• 112-90-3 trans-oleylamine 
• 1606178-86-2 (S,Z)-methyl 2-[3-(octadec-9-en-1-yl)ureido]-3-phenylpropanoate 
• 40165-68-2 di((Z)-octadec-9-enyl)amine 
• 72901-31-6 (9Z)-N-[(9Z)-9-octadecen-1-yl]-9-octadecenamide 

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Platinum in-situ catalytic Oleylamine (cas 112-90-3) combustion removal process for carbon supported platinum nanoparticles08/29/2019

Colloidal synthesis method such as oleylamine (OAm)-stabilized process is of great interest for obtaining uniform and highly dispersed platinum nanoparticle catalysts, yet the ligand may unavoidably inhibit their electro-catalytic performance. Thus, fully removing these ligands is critical to ac...detailed

Regular ArticleControl of morphology, photoluminescence, and stability of colloidal methylammonium lead bromide nanocrystals by Oleylamine (cas 112-90-3) capping molecules08/28/2019

Methylammonium lead bromide (CH3NH3PbBr3) thin films and nanocrystals are useful for solar cells and LED applications. In order to improve stability in ambient environment, CH3NH3PbBr3 nanocrystals have been synthesized using oleylamine as capping molecule. It was found that by increasing the ol...detailed

Effective reduction in the nanoparticle sizes of NiO obtained via the pyrolysis of nickel malonate precursor modified using Oleylamine (cas 112-90-3) surfactant08/25/2019

Nickel oxide nanoparticles were synthesized via thermal decomposition of two precursors, the first, a simple nickel malonate and the second, a nickel malonate modified by oleylamine, a surfactant, both having been synthesized by precipitation. While FTIR, TGA and ToF-SIMS were used to characteri...detailed

Research paperControl of Oleylamine (cas 112-90-3) to perovskite ratio in synthesis of MAPbBr3 nanoparticles08/20/2019

Methylammonium lead bromide (CH3NH3PbBr3) nanocrystals have great potentials for lighting and display applications. Previously we synthesized CH3NH3PbBr3 nanocrystals using oleylamine as capping molecule and found that by increasing the oleylamine to CH3NH3PbBr3 perovskite ratio (OPR), the photo...detailed

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