124-26-5

Basic information

• Product Name: Octadecanamide
• Synonyms: AMIDE C18;AKAWAX S-MICROBEADS;OCTADECANAMIDE;Octadecannamide;OCTADECANOAMIDE;N-OCTADECANAMIDE;STEAROYLAMIDE;STEARAMIDE
• CAS NO: 124-26-5
• Molecular Formula: C₁₈H₃₇NO
• Molecular Weight: 283.49
• EINECS: 204-693-2
• Product Categories: Color Former & Related Compounds;Functional Materials;Sensitizer;Amides;Building Blocks;C8 to C20+;Carbonyl Compounds;Chemical Synthesis;Organic Building Blocks
• Mol File: 124-26-5.mol
• Article Data: 22

Chemical Properties

• Melting Point: 98-102 °C(lit.)
• Boiling Point: 250-251 °C12 mm Hg(lit.)
• Flash Point: 207.5 °C
• Appearance: light yellow granules
• Density: 0.9271 (rough estimate)
• Vapor Pressure: 7.11E-07mmHg at 25°C
• Refractive Index: 1.432-1.434
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Slightly, Sonicated), Methanol (Slightly)
• PKA: 16.61±0.40(Predicted)
• Water Solubility: 102μg/L at 20℃
• BRN: 909006
• CAS DataBase Reference: Octadecanamide(CAS DataBase Reference)
• NIST Chemistry Reference: Octadecanamide(124-26-5)
• EPA Substance Registry System: Octadecanamide(124-26-5)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 1
• RTECS: RG0182000
• Hazardous Substances Data: 124-26-5(Hazardous Substances Data)

Usage

Chemical Properties

Octadecanamide is a white or light yellow granules. After recrystallization in ethanol, it is colorless leafy crystal. Soluble in hot ethanol, chloroform, ether, insoluble in cold ethanol, insoluble in water. Lubricity is lower than grease right, and the continuity is shorter. Thermal stability is poor, with initial coloring. With a small amount of advanced alcohol (C16 ~ 18) can overcome the above shortcomings.

Uses

Corrosion inhibitor in oil wells.

Definition

ChEBI: Octadecanamide is a fatty amide of stearic acid. It has a role as a metabolite. It derives from an octadecanoic acid.

Flammability and Explosibility

Nonflammable

Safety Profile

Questionable carcinogen withexperimental tumorigenic data. When heated todecomposition it emits toxic fumes of NOx.

InChI:InChI=1/C18H37NO/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h2-17H2,1H3,(H2,19,20)

Synthetic route

stearic acid (57-11-4) → stearamide (124-26-5)

Conditions	Yield
With titanium(IV) isopropylate; ammonia at 165℃; for 7h; Reagent/catalyst; Temperature; Large scale;	98.4%
With ammonium bicarbonate; formamide for 0.15h; Irradiation;	82%
Stage #1: stearic acid With 1,1'-carbonyldiimidazole In dichloromethane at 20℃; for 0.5h; Stage #2: With ammonia In dichloromethane for 12h;	23%

Octadecanoyl-carbamic acid tert-butyl ester (120158-01-2) → stearamide (124-26-5)

Conditions	Yield
With trifluoroacetic acid In dichloromethane for 1h; Ambient temperature;	97%

octadecanoyl azide (77165-65-2) → stearamide (124-26-5)

Conditions	Yield
With zinc(II) tetrahydroborate In 1,2-dimethoxyethane for 0.5h; Ambient temperature;	95%

stearonitrile (638-65-3) → stearamide (124-26-5)

Conditions	Yield
With N-ethyl-N-hydroxy-ethanamine; water at 100℃; for 5h;	90%
With sodium hydroxide; poly(ethylene glycol)-400 for 0.0166667h; microwave irradiation;	78%
(i) HCl, SnCl2, Et2O, (ii) H2O; Multistep reaction;

1-aminooctadecane (124-30-1) → stearamide (124-26-5)

Conditions	Yield
With fluorenone imine; oxygen In toluene for 60h; Reflux;	51%

stearic acid ethyl ester (111-61-5) → stearamide (124-26-5)

Conditions	Yield
With ammonia; water at 180℃;

2-hexadecyl-malonamic acid → stearamide (124-26-5)

Conditions	Yield
at 130 - 150℃;

2-hexadecyl-malonamic acid → methylammonium carbonate (15719-64-9, 15719-76-3, 97762-63-5) + stearamide (124-26-5)

Conditions	Yield
at 130 - 150℃;

(stearoylamino-methylsulfanyl)-acetic acid (102899-77-4) → stearamide (124-26-5)

formamide (77287-34-4, 77287-35-5, 60100-09-6) + stearic acid (57-11-4) → stearamide (124-26-5)

Conditions	Yield
at 180 - 190℃;

phenyl carbamate (64-10-8) + stearic acid (57-11-4) → N-phenylstearamide (637-54-7) + stearamide (124-26-5)

Conditions	Yield
at 160℃;

stearic acid (57-11-4) + urea (57-13-6) → stearamide (124-26-5)

Conditions	Yield
at 160℃;
With diammonium phosphate at 195℃;
at 160℃;
at 205 - 210℃;

Stearoyl chloride (112-76-5) → stearamide (124-26-5)

Conditions	Yield
With diethyl ether; ammonia
With ammonia
With ammonia

N-(1-Cyanethyl)-stearoylamid (40652-01-5) → stearamide (124-26-5)

Conditions	Yield
(thermolysis);

ammonia (7664-41-7) + stearic acid (57-11-4) → stearamide (124-26-5)

Conditions	Yield
at 135 - 200℃; Kinetics;

stearacidic ammonium → stearamide (124-26-5)

Conditions	Yield
at 230℃;

(stearoylamino-methylsulfanyl)-acetic acid (102899-77-4) + diluted acid → stearamide (124-26-5)

stearic acid (57-11-4) + zinc stearate → stearamide (124-26-5) + trichloromethyl-chloro formate

Conditions	Yield
Multi-step reaction with 2 steps 1: SOCl2 2: NH3 View Scheme

N-Boc-octadecylamine (38428-49-8) → stearamide (124-26-5) + phenylmercury hydroxide

Conditions	Yield
Multi-step reaction with 2 steps 1: 98 percent / ruthenium dioxide hydrate, 10percent aqueous NaIO4 / ethyl acetate / 3 h / Ambient temperature 2: 97 percent / trifluoroacetic acid / CH2Cl2 / 1 h / Ambient temperature View Scheme

1-aminooctadecane (124-30-1) → stearamide (124-26-5) + phenylmercury hydroxide

Conditions	Yield
Multi-step reaction with 3 steps 1: 95 percent / triethylamine / H2O; dioxane / 6 h / Ambient temperature 2: 98 percent / ruthenium dioxide hydrate, 10percent aqueous NaIO4 / ethyl acetate / 3 h / Ambient temperature 3: 97 percent / trifluoroacetic acid / CH2Cl2 / 1 h / Ambient temperature View Scheme

acetonin (53422-22-3) + sodium hydrogencarbonate (144-55-8) + Stearoyl chloride (112-76-5) → stearamide (124-26-5)

dimethyl amine (124-40-3) + methyl (9Z,12S,13R)-12,13-epoxy-9-octadecenoate (2733-91-7) → cis-9-octadecenoamide (301-02-0) + N,N-dimethyl-(12S,13R)-epoxy-cis-9-octadecenyl amide (1323108-64-0) + Palmitamide (629-54-9) + stearamide (124-26-5)

Conditions	Yield
Stage #1: dimethyl amine; methyl (9Z,12S,13R)-12,13-epoxy-9-octadecenoate With sodium methylate In methanol for 2h; Reflux; Stage #2: In methanol at 0℃; for 24.25h;

octadecanoyl azide (77165-65-2) → octadecyl isocyanate (112-96-9) + stearamide (124-26-5)

Conditions	Yield
With anthracene at 20℃; Kinetics; Reagent/catalyst; Photolysis;

1-{(2S)-2-[(diisopropoxyphosphoryl)methoxy-3-(triphenylmethoxy)]propyl}-5-azacytosine (933460-58-3) + docosanoyl chloride (21132-76-3) → (S,E)-(8-amino-3-(hydroxymethyl)-6,10-dioxo-2-oxa-5,7,9-triazahentriacont-7-en-1-yl)phosphonic acid (1608459-53-5) + stearamide (124-26-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: pyridine / 48 h / 20 °C 2: acetonitrile / 24 h / 20 °C View Scheme

trimethylsilyl bromide (2857-97-8) + 1-(2S)-2-[(diisopropoxyphosphoryl)methoxy-3-(triphenylmethoxy)propyl-N4-docosanoyl-5-azacytosine] (1608457-43-7) → (S,E)-(8-amino-3-(hydroxymethyl)-6,10-dioxo-2-oxa-5,7,9-triazahentriacont-7-en-1-yl)phosphonic acid (1608459-53-5) + stearamide (124-26-5)

Conditions	Yield
In acetonitrile at 20℃; for 24h;

N-methylol stearamide (3370-35-2) → stearamide (124-26-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: acetic acid methyl ester; sulfuric acid View Scheme

glycerol tristearate (555-43-1) → stearamide (124-26-5)

Conditions	Yield
With ammonia at 180℃; for 6h; Autoclave;	91 %Chromat.

stearamide (124-26-5) → stearonitrile (638-65-3)

Conditions	Yield
With triethylamine; trifluoroacetyl chloride In dichloromethane	95%
at 295℃; for 1h; Temperature;	86%
With trichloromethyl chloroformate; benzene

stearamide (124-26-5) → octadecylamine hydrochloride (1838-08-0)

Conditions	Yield
Stage #1: stearamide With titanium(IV) isopropylate In toluene at 20 - 100℃; Stage #2: With hydrogenchloride In diethyl ether; toluene	90%
Yield given. Multistep reaction;

[hydroxy(tosyloxy)iodo]benzene (27126-76-7) + stearamide (124-26-5) → heptadecylammonium p-toluenesulfonate (67038-06-6)

Conditions	Yield
In acetonitrile at 65 - 70℃; for 0.0333333h;	89.5%

stearamide (124-26-5) + polystyrene, linear, with -I(OH)OSO2C6H4-CH3-p groups → heptadecylammonium p-toluenesulfonate (67038-06-6)

Conditions	Yield
In acetonitrile for 2h; Heating;	89%

benzyl alcohol (100-51-6) + stearamide (124-26-5) → benzyl stearate (5531-65-7)

Conditions	Yield
With cerium(IV) oxide In 1,3,5-trimethyl-benzene at 165℃; for 22h; Inert atmosphere;	86%

stearamide (124-26-5) → stearic acid (57-11-4)

Conditions	Yield
With niobium(V) oxide; water In neat (no solvent) for 20h; Reflux; Inert atmosphere;	86%

stearamide (124-26-5) → n-Octadecanal (638-66-4)

Conditions	Yield
With lithium-tris(diethylamino)hydridoaluminate In tetrahydrofuran for 12h; Ambient temperature;	83%
Multi-step reaction with 2 steps 1: thionyl chloride 2: tin (II)-chloride; hydrogen chloride; diethyl ether / und beim Verseifen des Reaktionsprodukts mit warmem Wasser View Scheme

4-nitrobenzaldehdye (555-16-8) + stearamide (124-26-5) → N-(4-nitrobenzoyl)stearamide (1109247-32-6)

Conditions	Yield
Stage #1: 4-nitrobenzaldehdye; stearamide With copper(I) bromide In tetrachloromethane; acetonitrile at 20℃; for 0.25h; Inert atmosphere; Stage #2: With N-Bromosuccinimide In tetrachloromethane; acetonitrile at 90℃; for 15h; Inert atmosphere;	80%

Dimethyl-p-toluidine (99-97-8) + stearamide (124-26-5) → C27H48N2O

Conditions	Yield
With tert.-butylhydroperoxide; copper(I) bromide In decane at 80℃; for 6h;	78%

leelamine (1446-61-3) + stearamide (124-26-5) → (+)-N-(stearoyl)-dehydroabietylamine

Conditions	Yield
Stage #1: stearamide With borane tetrahydrofuran In toluene at 0 - 20℃; for 1h; Stage #2: leelamine In toluene Reflux;	77.68%

cis,trans-2,5-dimethoxytetrahydrofuran (696-59-3) + stearamide (124-26-5) → 1-Pyrrol-1-yl-octadecan-1-one (86734-18-1) + stearonitrile (638-65-3)

Conditions	Yield
With phosphorus pentoxide In toluene at 60 - 110℃; for 1.25h;	A 75% B 25%

ethanolamine (141-43-5) + stearamide (124-26-5) → N-stearoylethanolamine (111-57-9)

Conditions	Yield
Stage #1: stearamide With triethylamine; methyl chloroformate In dichloromethane at 0 - 20℃; for 2h; Stage #2: ethanolamine In dichloromethane at 0 - 20℃; for 20h;	74%

1,4-dichloro-1,4-dimethoxybutane (86428-38-8) + stearamide (124-26-5) → 1-Pyrrol-1-yl-octadecan-1-one (86734-18-1)

Conditions	Yield
With Amberlyst A-21 resin In acetonitrile at 55℃; for 16h;	72%

phenyl-λ3-iodanediyl bis(3-phenylpropanoate) + stearamide (124-26-5) → N-heptadecyl-3-phenylpropanamide

Conditions	Yield
In 1,2-dichloro-ethane at 100℃; for 24h;	71%

trimethyl phosphite (512-56-1) + stearamide (124-26-5) → N-methylstearylamide (20198-92-9)

Conditions	Yield
With n-butyllithium; cyclopentyl methyl ether In hexane at 115℃; for 24h; Reagent/catalyst; Inert atmosphere;	65%

Diphenylmethane (101-81-5) + stearamide (124-26-5) → N-benzhydrylstearamide

Conditions	Yield
With N-Bromosuccinimide; copper(I) bromide In ethyl acetate at 50℃; for 12h;	42%

4-bromo-N,N-dimethylaniline (586-77-6) + stearamide (124-26-5) → C26H45BrN2O (1042709-60-3)

Conditions	Yield
With N-chloro-succinimide; copper(I) bromide In ethyl acetate at 25℃; for 6h;	42%

2-Oxobutyric acid (600-18-0) + stearamide (124-26-5) → (Z)-2-Octadecanoylamino-but-2-enoic acid

Conditions	Yield
In toluene Heating;	25%

pyrrolidinylmethanol (20789-05-3) + stearamide (124-26-5) → N-pyrrolidinomethyl-stearamide

Conditions	Yield
at 150℃;

pyridine (110-86-1) + phosgene (75-44-5) + toluene (108-88-3) + stearamide (124-26-5) → stearoyl-carbamoyl chloride

Conditions	Yield
at 150℃;

9-hydroxyxanthene (90-46-0) + stearamide (124-26-5) → N-xanthen-9-yl-stearamide (6325-90-2)

Conditions	Yield
With acetic acid
With acetic acid

Upstream product

• 111-61-5 stearic acid ethyl ester 
• 102899-77-4 (stearoylamino-methylsulfanyl)-acetic acid 
• 64-10-8 phenyl carbamate 
• 57-11-4 stearic acid 
• 57-13-6 urea 
• 112-76-5 Stearoyl chloride 
• 638-65-3 stearonitrile 
• 7664-41-7 ammonia 
• 124-30-1 1-aminooctadecane 
• 53422-22-3 acetonin 
• 144-55-8 sodium hydrogencarbonate 
• 3370-35-2 N-methylol stearamide 
• 555-43-1 glycerol tristearate 
• 2857-97-8 trimethylsilyl bromide 

Downstream Products

• 106438-63-5 N-(4-methoxy-benzyl)-stearamide 
• 32582-85-7 N-{2-[2-(2-amino-ethylamino)-ethylamino]-ethyl}-stearamide 
• 13276-08-9 N-(octadecanoyl)octadecylamide 
• 112-92-5 1-octadecanol 
• 7664-41-7 ammonia 
• 57-11-4 stearic acid 
• 638-65-3 stearonitrile 
• 4200-95-7 1-heptadecanamine 
• 112-69-6 N,N-dimethylhexadecylamine 
• 124-28-7 N,N-dimethyl-n-octadecylamine 
• 1323108-61-7 N,N-dimethyl-(12S,13R)-epoxy-cis-9-octadecenyl amine 
• 14727-68-5 N,N-dimethyl-N-oleylamine 
• 111-57-9 N-stearoylethanolamine 
• 20198-92-9 N-methylstearylamide 

Relevant articles and documents

A Convenient Protocol for the Synthesis of Fatty Acid Amides

Several classes of biologically occurring fatty acid amides have been reported from mammalian and plant sources. Many amides conjugated with fatty acids of mammalian origin exhibit specific activation of individual receptors. Their potential as pharmacological tools or as lead compounds towards the development of novel therapeutics is of great interest. Hence, access to such amides by a practical, high-yielding and scalable protocol without affecting the geometry or position of sensitive functionalities is needed. A protocol that meets all these requirements involves activation of the corresponding acid with carbonyl diimidazole (CDI) followed by reaction with the desired amine or its hydrochloride. More than fifty compounds have been prepared in generally high yields.

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