2016-42-4

Basic information

• Product Name: 1-Tetradecylamine
• Synonyms: RARECHEM AL BW 0396;TETRADECYLAMINE;N-TETRADECYLAMINE;MYRISTYLAMINE;1-TETRADECYLAMINE;1-AMINOTETRADECANE;1-Tetradecanamine;alamine5d
• CAS NO: 2016-42-4
• Molecular Formula: C₁₄H₃₁N
• Molecular Weight: 213.4
• EINECS: 217-950-9
• Product Categories: Alkylamines;Monofunctional & alpha,omega-Bifunctional Alkanes;Monofunctional Alkanes
• Mol File: 2016-42-4.mol
• Article Data: 16

Chemical Properties

• Melting Point: 38-40 °C(lit.)
• Boiling Point: 162 °C15 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: White to pink/Crystals or Crystalline Solid
• Density: 0.993
• Vapor Pressure: 0.00189mmHg at 25°C
• Refractive Index: 1.5045-1.5065
• PKA: 10.62(at 25℃)
• Water Solubility: insoluble
• BRN: 1633740
• CAS DataBase Reference: 1-Tetradecylamine(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Tetradecylamine(2016-42-4)
• EPA Substance Registry System: 1-Tetradecylamine(2016-42-4)

Safety Data

• Hazard Codes: Xi,C
• Statements: 36/37/38-34
• Safety Statements: 26-36/37-45-36/37/39
• RIDADR: 3259
• WGK Germany: 2
• RTECS: XB7970000
• F: 10-34
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 2016-42-4(Hazardous Substances Data)

Usage

Description

1-Tetradecylamine, also known as Tetradecanamine, is an organic compound with the chemical formula CH3(CH2)13NH2. It is a white to pink crystalline solid that belongs to the class of alkylamines. 1-Tetradecylamine is characterized by its long hydrocarbon chain with an amine group at one end, which gives it unique chemical and physical properties.

Uses

1. Used in the Chemical Industry:
1-Tetradecylamine is used as an intermediate for the manufacture of cationic surface-active agents. Its long hydrocarbon chain and amine group provide it with surfactant properties, making it an effective ingredient in the production of cationic surfactants. These surfactants are widely used in various applications, such as detergents, emulsifiers, and dispersants.
2. Used in the Pharmaceutical Industry:
1-Tetradecylamine is used as an inhibitor of N-acylethanolamine-hydrolyzing acid amidase. This enzyme plays a role in the metabolism of endocannabinoids, which are involved in various physiological processes, including pain, appetite, and memory. By inhibiting this enzyme, 1-Tetradecylamine can potentially modulate the endocannabinoid system, offering therapeutic benefits in the treatment of various conditions.
3. Used in the Biotechnology Industry:
1-Tetradecylamine is also used as a germicide, thanks to its antimicrobial properties. The amine group in its structure allows it to interact with the cell membranes of microorganisms, disrupting their function and leading to their inactivation. This makes it a valuable component in the development of disinfectants and sanitizers for use in various settings, such as healthcare, food processing, and personal care products.

Flammability and Explosibility

Nonflammable

InChI:InChI=1/C14H31N.C2H4O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15;1-2(3)4/h2-15H2,1H3;1H3,(H,3,4)

Synthetic route

myristonitrile (629-63-0) → tetradecylamine (2016-42-4)

Conditions	Yield
With samarium diiodide; water; triethylamine In tetrahydrofuran at 20℃; for 0.0833333h; Inert atmosphere;	94%
With sodium hydroxide; nickel at 70℃; Hydrogenation;
With kieselguhr; ammonia; nickel at 135℃; Hydrogenation;
With ethanol; sodium

1-(2-aminoethyl)-β-D-galactopyranoside (70337-78-9, 70337-79-0, 140428-88-2) + tetradecyl isocyanate (4877-14-9) → tetradecylamine (2016-42-4) + 1-Tetradecyl-3-[2-((2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-ethyl]-urea

Conditions	Yield
In methanol; isopropyl alcohol at 20℃; for 2h;	A n/a B 92%

tetradecanamide (638-58-4) → tetradecylamine (2016-42-4)

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran at 65℃; Concentration;	89.5%
With lithium aluminium tetrahydride In tetrahydrofuran at 65℃; Reflux;	89.5%
With lithium aluminium tetrahydride In tetrahydrofuran Reflux;	89.5%
With lithium aluminium tetrahydride In tetrahydrofuran at 20℃; Reflux;	89.5%
With lithium aluminium tetrahydride; diethyl ether

myristonitrile (629-63-0) → tetradecylamine (2016-42-4) + 1-Tetradecanol (112-72-1)

Conditions	Yield
With samarium diiodide; water; triethylamine; diisopropylamine In tetrahydrofuran at 20℃; for 2h; Inert atmosphere;	A 86% B 13%

myristoyl azide (77165-64-1) → tetradecylamine (2016-42-4)

Conditions	Yield
Stage #1: myristoyl azide With hydrogenchloride In water at 50℃; for 3h; Reflux; Stage #2: With tetrabutylammomium bromide; sodium hydroxide In water at 60℃; for 1h; pH=> 9; Temperature;	85.9%

N-cyclopropyl-N-tetradecyl-4-methylbenzenesulfonamide → p-toluene sulfinic acid (536-57-2) + tetradecylamine (2016-42-4)

Conditions	Yield
With N1,N1,N12,N12-tetramethyl-7,8-dihydro-6H-dipyrido[1,2-a:2,1'-c][1,4]diazepine-2,12-diamine In N,N-dimethyl-formamide for 72h; UV-irradiation;	A 78% B 85%

pyrrolidine (123-75-1) + myristonitrile (629-63-0) → 1-tetradecylpyrrolidine (74673-29-3) + tetradecylamine (2016-42-4) + 1-Tetradecanol (112-72-1)

Conditions	Yield
With samarium diiodide; water; triethylamine In tetrahydrofuran at 20℃; for 0.0833333h; Inert atmosphere;	A 24% B 71% C 4.4%

n-tetradecanoic acid (544-63-8) → tetradecylamine (2016-42-4) + ditetradecylamine (17361-44-3) + N-tetradecyltetradecanamide

Conditions	Yield
Stage #1: n-tetradecanoic acid With cyclopentyl methyl ether; ammonia at 200℃; under 4500.45 Torr; Sealed tube; Green chemistry; Stage #2: With cyclopentyl methyl ether; ammonia; hydrogen at 200℃; under 42004.2 Torr; for 6.5h; Cooling with ice; Green chemistry;	A 70% B 20% C 6%

myristonitrile (629-63-0) + N-butylamine (109-73-9) → tetradecylamine (2016-42-4) + Butyl-tetradecyl-amine (19141-94-7)

Conditions	Yield
With samarium diiodide; water; triethylamine In tetrahydrofuran at 20℃; for 0.0833333h; Inert atmosphere;	A 51% B 48%

N-tetradecyl-succinamic acid (3151-46-0) → tetradecylamine (2016-42-4)

Conditions	Yield
With hydrogenchloride

n-dodecylacetohydroxamic acid (17698-03-2) → tetradecylamine (2016-42-4)

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran Heating;

myristaldehyde oxime → tetradecylamine (2016-42-4)

Conditions	Yield
With sodium amalgam man haelt die Loesung durch zeitweiligen Zusatz von Essigsaeure stets sauer;

phthalimide (136918-14-4) + tetradecyl halide → tetradecylamine (2016-42-4)

Conditions	Yield
With potassium carbonate und Erwaermen des Reaktionsprodukts mit Hydrazin-hydrat und Aethanol;

n-tetradecanoic acid (544-63-8) → tetradecylamine (2016-42-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: ammonia / 290 - 300 °C 2: Raney nickel; NaOH-solution / 70 °C / Hydrogenation View Scheme
Multi-step reaction with 3 steps 1: oxalyl dichloride / toluene / 2 h / 70 °C 2: ammonia / 10 °C 3: lithium aluminium tetrahydride / tetrahydrofuran / 65 °C View Scheme
Multi-step reaction with 3 steps 1: oxalyl dichloride / toluene / 2 h / 70 °C 2: ammonium hydroxide / 10 °C 3: lithium aluminium tetrahydride / tetrahydrofuran / 65 °C / Reflux View Scheme

ammonium thiocyanate + 4-cyanobenzoyl chlorIde (6068-72-0) → 1-(4-cyanobenzoyl)-3-n-tetradecylthiourea (174802-52-9) + tetradecylamine (2016-42-4)

Conditions	Yield
In acetone

myristonitrile (629-63-0) + 3-phenylpropanoic acid methyl ester (103-25-3) → tetradecylamine (2016-42-4) + 3-Phenyl-1-propanol (122-97-4)

Conditions	Yield
With samarium diiodide; water; triethylamine In tetrahydrofuran at 20℃; Inert atmosphere;

myristonitrile (629-63-0) + ethyl dihydrocinnamate (2021-28-5) → tetradecylamine (2016-42-4) + 3-Phenyl-1-propanol (122-97-4)

Conditions	Yield
With samarium diiodide; water; triethylamine In tetrahydrofuran at 20℃; Inert atmosphere;

myristonitrile (629-63-0) + 1-methylethyl 3-phenylpropionoate (22767-95-9) → tetradecylamine (2016-42-4) + 3-Phenyl-1-propanol (122-97-4)

Conditions	Yield
With samarium diiodide; water; triethylamine In tetrahydrofuran at 20℃; Inert atmosphere;

myristonitrile (629-63-0) + tert-butyl 3-phenylpropanoate (16537-10-3) → tetradecylamine (2016-42-4) + 3-Phenyl-1-propanol (122-97-4)

Conditions	Yield
With samarium diiodide; water; triethylamine In tetrahydrofuran at 20℃; Inert atmosphere;

myristonitrile (629-63-0) + phenyl 3-phenylpropanoate (726-26-1) → tetradecylamine (2016-42-4) + 3-Phenyl-1-propanol (122-97-4)

Conditions	Yield
With samarium diiodide; water; triethylamine In tetrahydrofuran at 20℃; Inert atmosphere;

myristonitrile (629-63-0) + 3-Phenylpropionic acid (501-52-0) → tetradecylamine (2016-42-4) + 3-Phenyl-1-propanol (122-97-4)

Conditions	Yield
With samarium diiodide; water; triethylamine In tetrahydrofuran at 20℃; Inert atmosphere;

myristonitrile (629-63-0) + 3-phenylpropionamide (102-93-2) → tetradecylamine (2016-42-4) + 3-Phenyl-1-propanol (122-97-4)

Conditions	Yield
With samarium diiodide; water; triethylamine In tetrahydrofuran at 20℃; Inert atmosphere;

myristonitrile (629-63-0) + N,N-diethyl-3-phenylpropanamide (18859-19-3) → tetradecylamine (2016-42-4) + 3-Phenyl-1-propanol (122-97-4)

Conditions	Yield
With samarium diiodide; water; triethylamine In tetrahydrofuran at 20℃; Inert atmosphere;

tetradecanoyl chloride (112-64-1) → tetradecylamine (2016-42-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: ammonia / 10 °C 2: lithium aluminium tetrahydride / tetrahydrofuran / 65 °C View Scheme
Multi-step reaction with 2 steps 1: ammonium hydroxide / 10 °C 2: lithium aluminium tetrahydride / tetrahydrofuran / 65 °C / Reflux View Scheme
Multi-step reaction with 2 steps 1: ammonium hydroxide / neat (no solvent) / 10 °C 2: lithium aluminium tetrahydride / tetrahydrofuran / Reflux View Scheme

methyl myristoate (124-10-7) → tetradecylamine (2016-42-4)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: hydrazine hydrate / methanol / 5 h / Reflux 2.1: hydrogenchloride; sodium nitrite / chloroform; water / 0.67 h / 10 - 15 °C 3.1: hydrogenchloride / water / 3 h / 50 °C / Reflux 3.2: 1 h / 60 °C / pH > 9 View Scheme

tritetradecanoylglycerol (555-45-3) → tetradecylamine (2016-42-4) + ditetradecylamine (17361-44-3)

Conditions	Yield
With ammonium hydroxide; hydrogen at 220℃; under 41254.1 Torr; for 36h; Autoclave;	A 54 %Chromat. B 19 %Chromat.

tetradecylamine (2016-42-4) + tetradecanoyl chloride (112-64-1) → N-tetradecyltetradecanamide

Conditions	Yield
With triethylamine In benzene at 10 - 20℃;	100%
With triethylamine In benzene at 10 - 20℃;	100%
With triethylamine In tetrahydrofuran at 0 - 20℃; for 20h;	99%
With potassium carbonate In diethyl ether	82%

tetradecylamine (2016-42-4) + N-(benzyloxycarbonyl)-L-serine (1145-80-8) → N-benzyloxycarbonyl-L-serine myristylamide (171191-19-8)

Conditions	Yield
With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In N,N-dimethyl-formamide	100%

tetradecylamine (2016-42-4) + 5-(4'-carboxyphenyl)-10,15,20-tris[3,5-di(tert-butyl)phenyl]porphyrin → N-Tetradecyl-4-[(1Z,4Z,9Z,15Z)-10,15,20-tris-(3,5-di-tert-butyl-phenyl)-porphyrin-5-yl]-benzamide

Conditions	Yield
Stage #1: 5-(4'-carboxyphenyl)-10,15,20-tris[3,5-di(tert-butyl)phenyl]porphyrin With dmap; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In tetrahydrofuran at 0℃; for 1h; Stage #2: tetradecylamine In tetrahydrofuran at 0 - 20℃;	100%

C52H47NO12 (848827-42-9) + tetradecylamine (2016-42-4) → C66H76N2O11 (848827-43-0)

Conditions	Yield
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; 1-hydroxybenzotriazol-hydrate In 1,2-dichloro-ethane	100%

N,N-dimethylacetamide dimethyl acetal (18871-66-4) + tetradecylamine (2016-42-4) → N'-tetradecyl-N,N-dimethylacetimidamide (1268136-31-7)

Conditions	Yield
With dimethyl amine In tetrahydrofuran at 20℃; for 18.25h; Darkness; chemoselective reaction;	100%

tetradecylamine (2016-42-4) + n-tetradecanoic acid (544-63-8) → N-tetradecyltetradecanamide

Conditions	Yield
Stage #1: n-tetradecanoic acid With oxalyl dichloride; N,N-dimethyl-formamide In benzene at 20 - 60℃; for 2h; Stage #2: tetradecylamine With triethylamine In benzene at 10 - 20℃;	100%
Stage #1: n-tetradecanoic acid With oxalyl dichloride In N,N-dimethyl-formamide; benzene at 20 - 60℃; for 2h; Stage #2: tetradecylamine With triethylamine In benzene at 10 - 20℃;	100%

tetradecylamine (2016-42-4) + (7-(carboxymethyl)-1,3,6,8-tetraoxo-3,6,7,8-tetrahydro-1H-benzo[lmn][3,8]phenanthrolin-2-yl)-acetic acid (5880-06-8) → C18H10N2O8*2C14H31N

Conditions	Yield
In methanol at 20℃;	100%

tetradecylamine (2016-42-4) + (3S,4S)-1-(tert-butoxycarbonyl)pyrrolidine-3,4-dicarboxylic acid → tert-butyl (3S,4S)-3,4-bis(tetradecylcarbamoyl)pyrrolidine-1-carboxylate

Conditions	Yield
Stage #1: tetradecylamine; (3S,4S)-1-(tert-butoxycarbonyl)pyrrolidine-3,4-dicarboxylic acid With 2,6-dimethylpyridine; 1-hydroxy-7-aza-benzotriazole In dichloromethane; N,N-dimethyl-formamide for 0.0833333h; Stage #2: With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane; N,N-dimethyl-formamide at 20℃; for 3.5h;	100%
With 2,6-dimethylpyridine; 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane; N,N-dimethyl-formamide at 25℃; for 3.5h;	91%

tetradecylamine (2016-42-4) + acetic anhydride (108-24-7) → N-tetradecylacetamide (14303-94-7)

Conditions	Yield
With triethylamine In acetonitrile at 0℃; for 0.75h;	99%
With pyridine In benzene at 20℃;	64%
With acetic acid

tetradecylamine (2016-42-4) + S-dodecyl dodecanethioate (103212-64-2) → N-lauroyltetradecanylamine (858482-12-9)

Conditions	Yield
In water for 3h; Reflux;	99%

tetradecylamine (2016-42-4) + 1-cyano-cyclopropanecarboxylic acid (6914-79-0) → 1-cyano-N-tetradecylcyclopropanecarboxamide (1266666-36-7)

Conditions	Yield
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 4h; Inert atmosphere;	99%

tetradecylamine (2016-42-4) + 5,6-bis(4-bromophenyl)-3-pyridin-2-yl-[1,2,4]triazine (669707-12-4) → 5,6-bis(4-tetradecylaminophenyl)-3-pyridin-2-yl-[1,2,4]-triazine

Conditions	Yield
With potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0); (R)-1-[(SP)-2-(dicyclohexylphosphino)ferrocenyl]ethyldi-tert-butylphosphine In toluene at 100℃; for 20h; Inert atmosphere;	99%

tetradecylamine (2016-42-4) + Fmoc β2,2h-bis-Orn(Boc)2OH → Fmoc β2,2h-bis-Orn(Boc)2NH(CH2)13CH3

Conditions	Yield
With dmap; benzotriazol-1-ol; dicyclohexyl-carbodiimide In dichloromethane at 20℃; Inert atmosphere;	99%

tetradecylamine (2016-42-4) + (3-chloropropyl)triethoxysilane (5089-70-3) → C32H71NO6Si2*ClH

Conditions	Yield
With sodium iodide In dimethyl sulfoxide at 90℃; for 2h;	98.6%

formaldehyd (50-00-0) + tetradecylamine (2016-42-4) + Glyoxal (131543-46-9) + acetic acid (64-19-7) → 1,3-di(tetradecyl)imidazolium acetate

Conditions	Yield
In water	98.5%

tetradecylamine (2016-42-4) + acrylic acid methyl ester (292638-85-8) → N-tetradecyl-β-aminopropionic acid methyl ester

Conditions	Yield
at 70℃; for 7.7h; Michael Addition;	97.5%
In methanol at 35℃; for 8h; Reflux;

tetradecylamine (2016-42-4) + BOC-O-benzyl-L-serine (23680-31-1) → tert-butyl N-[(S)-2-benzyloxy-1-(tetradecylcarbamoyl)ethyl]carbamate (243473-96-3)

Conditions	Yield
With 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 20h;	97%

tetradecylamine (2016-42-4) + (2E,4E,6E)-2,4,6-octatrienal (16326-86-6) → (E)-N-((2E,4E,6E)-octatrien-1-ylidene)-tetradecan-1-amine

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

tetradecylamine (2016-42-4) + (R)-1-(tert-butoxycarbonyl)pyrrolidine-3-carboxylic acid (72925-16-7) → tert-butyl (R)-3-(tetradecylcarbamoyl)pyrrolidine-1-carboxylate

Conditions	Yield
Stage #1: tetradecylamine; (R)-1-(tert-butoxycarbonyl)pyrrolidine-3-carboxylic acid With 2,6-dimethylpyridine; 1-hydroxy-7-aza-benzotriazole In dichloromethane for 0.0833333h; Stage #2: With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 3.5h;	97%
With 2,6-dimethylpyridine; 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 3.5h;	97%

tetradecylamine (2016-42-4) + Boc-Asp-OH (13726-67-5) → N-Boc-N’,N’’-di(myristoyl)-L-aspartamide

Conditions	Yield
Stage #1: Boc-Asp-OH With triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide Stage #2: tetradecylamine In N,N-dimethyl-formamide	97%

tetradecylamine (2016-42-4) + acrylonitrile (107-13-1) → N-tetradecyl-bis(2-cyanoethyl)amine (87085-90-3)

Conditions	Yield
In methanol at 45℃; for 19h;	96%

tetradecylamine (2016-42-4) + 1,2-bis(5-(2-carboxyethyl)-3-methyl-2-thienyl)hexafluorocyclopentene (1609928-88-2) → 1,2-bis(5-(N-tetradecyl-2-carbamoylethyl)-3-methyl-2-thienyl)hexafluorocyclopentene

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In chloroform at 20℃; for 2h;	95%

tetradecylamine (2016-42-4) + Fmoc-Ser(tBu)-OH (71989-33-8) → N-(9-fluorenylmethyloxycarbonyl)-O-tert-butyl-L-serine tetradecylamide

Conditions	Yield
Stage #1: Fmoc-Ser(tBu)-OH With diisopropyl-carbodiimide In dichloromethane at 20℃; for 0.25h; Inert atmosphere; Stage #2: tetradecylamine In dichloromethane for 18h; Inert atmosphere;	95%

tetradecylamine (2016-42-4) + (S)-1-N-boc-β-proline (140148-70-5) → tert-butyl (S)-3-(tetradecylcarbamoyl)pyrrolidine-1-carboxylate

Conditions	Yield
Stage #1: tetradecylamine; (S)-1-N-boc-β-proline With 2,6-dimethylpyridine; 1-hydroxy-7-aza-benzotriazole In dichloromethane for 0.0833333h; Stage #2: With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 3.5h;	95%
With 2,6-dimethylpyridine; 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 3.5h;	95%

tetradecylamine (2016-42-4) + (E)-3-(3,4,5-trimethoxyphenyl)acryloyl chloride (10263-19-1, 89652-61-9) → (E)-N-tetradecyl-3-(3,4,5-trimethoxyphenyl)acrylamide

Conditions	Yield
With triethylamine In dichloromethane at 0℃; for 2h; Inert atmosphere;	95%

succinic acid anhydride (108-30-5) + tetradecylamine (2016-42-4) → N-tetradecylsuccinimide

Conditions	Yield
Stage #1: succinic acid anhydride; tetradecylamine With triethylamine In ethylene glycol; N,N-dimethyl-formamide at 80℃; for 0.416667h; Stage #2: In acetic anhydride; N,N-dimethyl-formamide at 80℃; for 0.666667h;	94%
With acetic anhydride 1.) from 100 deg C to 120 deg C, 2.) from 120 deg C to 130 deg C, 1.5 h; Yield given. Multistep reaction;

tetradecylamine (2016-42-4) + benzoyl chloride (98-88-4) → N-tetradecylbenzamide (102456-53-1)

Conditions	Yield
With potassium carbonate In diethyl ether	94%

tetradecylamine (2016-42-4) → N-tetradecyl-3-hydroxybutyramide

Conditions	Yield
In hexane	94%

tetradecylamine (2016-42-4) + copper(II) stearate (660-60-6, 7617-31-4, 20563-00-2) → [Cu(stearate)2(tetradecylamine)2]

Conditions	Yield
In n-heptane for 0.5h; Reflux;	94%

Upstream product

• 3151-46-0 N-tetradecyl-succinamic acid 
• 70337-78-9 1-(2-aminoethyl)-β-D-galactopyranoside 
• 4877-14-9 tetradecyl isocyanate 
• 544-63-8 n-tetradecanoic acid 
• 555-45-3 tritetradecanoylglycerol 
• 77165-64-1 myristoyl azide 
• 124-10-7 methyl myristoate 
• 112-64-1 tetradecanoyl chloride 
• 136918-14-4 phthalimide 
• 17698-03-2 n-dodecylacetohydroxamic acid 
• 638-58-4 tetradecanamide 
• 629-63-0 myristonitrile 
• 18859-19-3 N,N-diethyl-3-phenylpropanamide 
• 102-93-2 3-phenylpropionamide 

Downstream Products

• 59005-06-0 N-tetradecylpyrrolidone 
• 10054-22-5 5-oxo-1-tetradecyl-pyrrolidine-3-carboxylic acid 
• 3224-48-4 1-tetradecyl isothiocyanate 
• 17361-44-3 ditetradecylamine 
• 32322-48-8 N-tetradecylyl-2-chloroacetamide 
• 1243-66-9 N-tetradecyl-p-toluenesulfonamide 
• 18375-64-9 N-tetradecyl-D-gluconamide 
• 20172-48-9 C₂₁H₃₄ClN 
• 20172-72-9 Dimethyl-{4-[(E)-tetradecyliminomethyl]-phenyl}-amine 
• 20172-57-0 C₂₁H₃₃Cl₂N 
• 47150-19-6 1-tetradecyl-1H-pyrrole-2,5-dione 
• 91472-64-9 N-tetradecyl-2,4,6-trinitroaniline 
• 78961-21-4 Tetradecylamine; compound with chloro-acetic acid 
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Relevant articles and documents

Assembly of sugars on polystyrene plates: A new facile microarray fabrication technique

The work presented herein is a new noncovalent glycoarray assembly method for microplates created by simply mixing together an isocyanate-containing C14-hydrocarbon and an amine-containing carbohydrate. 2-Aminoethyl-β-D-galactopyranoside (1) was utilized in model studies and product formation was detected by both ESI-MS and lectin binding. The method has been further extended to array complex carbohydrates.

One-pot reductive amination of carboxylic acids: a sustainable method for primary amine synthesis

The reductive amination of carboxylic acids is a very green, efficient and sustainable method for the production of (bio-based) amines. However, with current technology, this reaction requires two to three reaction steps. Here, we report the first (heterogeneous) catalytic system for the one-pot reductive amination of carboxylic acids to amines, with solely H2 and NH3 as the reactants. This reaction can be performed with relatively cheap ruthenium-tungsten bimetallic catalysts in the green and benign solvent cyclopentyl methyl ether (CPME). Selectivities of up to 99% for the primary amine could be achieved at high conversions. Additionally, the catalyst is recyclable and tolerant for common impurities such as water and cations (e.g. sodium carboxylate).

Selective Transformations of Triglycerides into Fatty Amines, Amides, and Nitriles by using Heterogeneous Catalysis

The use of triglycerides as an important class of biomass is an effective strategy to realize a more sustainable society. Herein, three heterogeneous catalytic methods are reported for the selective one-pot transformation of triglycerides into value-added chemicals: i) the reductive amination of triglycerides into fatty amines with aqueous NH3 under H2 promoted by ZrO2-supported Pt clusters; ii) the amidation of triglycerides under gaseous NH3 catalyzed by high-silica H-beta (Hβ) zeolite at 180 °C; iii) the Hβ-promoted synthesis of nitriles from triglycerides and gaseous NH3 at 220 °C. These methods are widely applicable to the transformation of various triglycerides (C4–C18 skeletons) into the corresponding amines, amides, and nitriles.