58670-89-6

Basic information

• Product Name: 2-DECYL-1-TETRADECANOL
• Synonyms: 2-decyl-1-tetradecano;2-DECYL-1-TETRADECANOL;DECYLTETRADECANOL;1-Tetradecanol, 2-decyl-;Einecs 261-385-0;isoalcohols;2-decyltetradecyl alcohol;ISOFOL 24
• CAS NO: 58670-89-6
• Molecular Formula: C₂₄H₅₀O
• Molecular Weight: 354.65
• EINECS: 261-385-0
• Product Categories: Alcohols;C9 to C30;Oxygen Compounds
• Mol File: 58670-89-6.mol
• Article Data: 2

Chemical Properties

• Melting Point: 17-20 °C(lit.)
• Boiling Point: 271-275 °C/33 mmHg(lit.)
• Flash Point: 113 °C
• Appearance: /
• Density: 0.842 g/mL at 25 °C(lit.)
• Vapor Pressure: 2.62E-08mmHg at 25°C
• Refractive Index: n20/D 1.457(lit.)
• PKA: 15.03±0.10(Predicted)
• CAS DataBase Reference: 2-DECYL-1-TETRADECANOL(CAS DataBase Reference)
• NIST Chemistry Reference: 2-DECYL-1-TETRADECANOL(58670-89-6)
• EPA Substance Registry System: 2-DECYL-1-TETRADECANOL(58670-89-6)

Safety Data

• WGK Germany: nwg
• Hazardous Substances Data: 58670-89-6(Hazardous Substances Data)

Usage

Uses

2-Decyl-1-tetradecanol may be used in the preparation of 2-decyltetradecyl (4-nitrophenyl)[11-([(2,5-dioxotetrahydro-1H-1-pyrrolyl)oxy]carbonyloxy)undecyl]phosphonate.

General Description

2-Decyl-1-tetradecanol participates in the preparation of monosaccharide glycolipid.

InChI:InChI=1/C24H50O/c1-3-5-7-9-11-13-14-16-18-20-22-24(23-25)21-19-17-15-12-10-8-6-4-2/h24-25H,3-23H2,1-2H3

Synthetic route

1-dodecyl alcohol (112-53-8) → 2-decylteradecanol (58670-89-6)

Conditions	Yield
With dichloro(pentamethylcyclopentadienyl) iridium; potassium tert-butylate; 1,7-Octadiene In para-xylene at 120℃; for 4h; Guerbet reaction;	86%
With heptanal; potassium hydroxide at 250℃; under 300 Torr; for 4h; Guerbet Reaction; Dean-Stark;

Dodecanal (112-54-9) + benzyl alcohol (100-51-6) → 2-decylteradecanol (58670-89-6) + 2-benzyldodecan-1-ol (107613-30-9)

Conditions	Yield
With potassium hydroxide at 205℃;

Dodecanal (112-54-9) → 2-decylteradecanol (58670-89-6) + α-decyl-hydrocinnamyl alcohol

Conditions	Yield
With potassium hydroxide at 205℃;

Dodecanal (112-54-9) + benzyl alcoholic KOH → 2-decylteradecanol (58670-89-6) + benzoic acid (65-85-0) + α-decyl-hydrocinnamyl alcohol

2-decylteradecanol (58670-89-6) → 11-bromomethyl-tricosane (732276-63-0)

Conditions	Yield
Stage #1: 2-decylteradecanol With triphenylphosphine In dichloromethane at 0℃; for 0.0833333h; Inert atmosphere; Stage #2: With N-Bromosuccinimide In dichloromethane for 16h;	98%
With N-Bromosuccinimide; triphenylphosphine In dichloromethane at 0 - 20℃; for 24h;	97%
With N-Bromosuccinimide; triphenylphosphine In dichloromethane at 20℃; for 50h; Cooling with ice;	95%

d,l-2-ethylhexanal (123-05-7) + 2-decylteradecanol (58670-89-6) → (Z)-11-(((2-ethylhex-1-en-1-yl)oxy)methyl)tricosane ether

Conditions	Yield
With pyridine; toluene-4-sulfonic acid In toluene at 145 - 150℃; for 5h; Temperature; Reagent/catalyst; Solvent; Dean-Stark;	98%

2-decylteradecanol (58670-89-6) → 2-decyltetradecanal (13893-38-4)

Conditions	Yield
With Dess-Martin periodane In dichloromethane for 5h; Inert atmosphere;	97%
With pyridinium chlorochromate

2-decylteradecanol (58670-89-6) + p-toluenesulfonyl chloride (98-59-9) → toluene-4-sulfonic acid 2-decyl-1-tetradecyl ester (132004-78-5)

Conditions	Yield
Stage #1: 2-decylteradecanol With trimethylamine hydrochloride; triethylamine In dichloromethane for 0.333333h; Cooling with ice; Stage #2: p-toluenesulfonyl chloride In dichloromethane at 0℃; for 3h;	95%
Stage #1: 2-decylteradecanol; p-toluenesulfonyl chloride With pyridine In dichloromethane at 0 - 20℃; for 3h; Stage #2: With water In dichloromethane at 0℃;	88%
With pyridine In dichloromethane at 20℃; for 3h; Cooling with ice;	88%

1-(2,3-dihydroxy propyl)piperazine (7483-59-2) + 2-decylteradecanol (58670-89-6) → 3-(4-(2-decyltetradecyl)-1-piperazinyl)-1,2-propanediol

Conditions	Yield
Stage #1: 2-decylteradecanol With methanesulfonyl chloride; triethylamine In dichloromethane at -10 - 25℃; for 17.5h; Inert atmosphere; Stage #2: 1-(2,3-dihydroxy propyl)piperazine In ethanol at 150℃; for 13h; Reagent/catalyst; Solvent; Temperature; Inert atmosphere;	94%

2-decylteradecanol (58670-89-6) → 2-decyltetradecanoic acid (93778-52-0)

Conditions	Yield
With Jones reagent In acetone at 0℃; Jones Oxidation;	92.3%

n-pentyl methyl ketone (110-43-0) + 2-decylteradecanol (58670-89-6) → C31H64O

Conditions	Yield
With 5%-palladium/activated carbon; hydrogen at 120℃; under 7757.43 Torr; for 5h; Reagent/catalyst; Sealed tube;	91%

2-decylteradecanol (58670-89-6) + butyraldehyde (123-72-8) → C28H58O

Conditions	Yield
With 5%-palladium/activated carbon; hydrogen at 120℃; under 7757.43 Torr; for 5h; Sealed tube;	88%

2-decylteradecanol (58670-89-6) + cyclopentanone (120-92-3) → C29H58O

Conditions	Yield
With 5%-palladium/activated carbon; hydrogen at 120℃; under 7757.43 Torr; for 5h; Sealed tube;	87%

2-decylteradecanol (58670-89-6) + C43H47NO2 (1234195-79-9) → C67H95NO2 (1220707-47-0)

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 25℃; for 12h; Inert atmosphere;	86%

2-decylteradecanol (58670-89-6) + isobutyraldehyde (78-84-2) → C28H58O

Conditions	Yield
With 5%-palladium/activated carbon; hydrogen at 120℃; under 7757.43 Torr; for 5h; Sealed tube;	86%

1,2,3-Benzotriazole (95-14-7) + 2-decylteradecanol (58670-89-6) → 2-(2-decyltetradecyl)-2H-benzo[d][1,2,3]triazole

Conditions	Yield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 20℃; for 1h; Inert atmosphere;	85%

2-decylteradecanol (58670-89-6) + 4,4'-dihydroxybenzil (33288-79-8) → 4,4'-bis(2-decyltetradecyloxy)benzil

Conditions	Yield
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran; toluene at 0 - 20℃; for 2h; Mitsunobu reaction;	82%

2-decylteradecanol (58670-89-6) + 2,4,6-tribromophenol (118-79-6) → 1,3,5-tribromo-2-((2-decyltetradecyl)oxy)benzene (1609380-31-5)

Conditions	Yield
With di-isopropyl azodicarboxylate; triphenylphosphine In dichloromethane at 0 - 20℃; Inert atmosphere;	82%

2-decylteradecanol (58670-89-6) + 4-bromo-1-naphthoic acid chloride (87700-65-0) → 2-decyltetradecyl 4-bromo-1-naphthoate

Conditions	Yield
With pyridine In tetrahydrofuran at 70℃;	81%

2-decylteradecanol (58670-89-6) + C44H47NO4 (1234196-35-0) → C92H143NO4 (1220707-48-1)

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 25℃; for 12h; Inert atmosphere;	80%

2-ethylhexanal dimethyl acetal (14250-95-4) + 2-decylteradecanol (58670-89-6) → (Z)-11-(((2-ethylhex-1-en-1-yl)oxy)methyl)tricosane ether

Conditions	Yield
With pyridinium p-toluenesulfonate at 20 - 135℃; Dean-Stark; Inert atmosphere;	78%

2-decylteradecanol (58670-89-6) + perylene-3,4-dicarboximide-9,10-di-(decyloxycarbonyl) (1128107-68-5) → N-(2-decyltetradecyl)-perylene-3,4-dicarboximide-9,10-di-(decyloxycarbonyl) (1128107-71-0)

Conditions	Yield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 20℃; for 168h; Mitsunobu reaction;	76.2%

2-decylteradecanol (58670-89-6) → 1-iodine-2-decyltetradecane (1143585-16-3)

Conditions	Yield
With hydrogen iodide In water Heating / reflux;	73%
With hydrogen iodide In water Reflux;	73%

2-decylteradecanol (58670-89-6) + hydrogen iodide (10034-85-2) → 1-iodine-2-decyltetradecane (1143585-16-3)

Conditions	Yield
	73%

2-Methylbutyraldehyde (96-17-3, 57456-98-1) + 2-decylteradecanol (58670-89-6) → (Z)-11-(((2-methylbut-1-en-1-yl)oxy)methyl)tricosane ether

Conditions	Yield
With pyridinium p-toluenesulfonate In 5,5-dimethyl-1,3-cyclohexadiene at 130℃; for 5h; Dean-Stark;	71%

1 ,6-dibromohexane (629-03-8) + 2-decylteradecanol (58670-89-6) → 11-((6-bromohexyloxy)methyl)tricosane

Conditions	Yield
Stage #1: 2-decylteradecanol With sodium In tetrahydrofuran at 70℃; for 2h; Stage #2: 1 ,6-dibromohexane In tetrahydrofuran at 80℃; for 8h;	70.44%
Stage #1: 2-decylteradecanol With sodium In tetrahydrofuran at 70℃; for 2h; Stage #2: 1 ,6-dibromohexane With lithium chloride; copper(I) bromide In tetrahydrofuran at 80℃; for 8h;	70.44%

2-decylteradecanol (58670-89-6) + C46H44Cl4N4O12 (1361053-33-9) → C94H140Cl4N4O12 (1365657-63-1)

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In tetrahydrofuran at 20℃; for 24h;	70%

2,3-Dimethyl-2-butene (563-79-1) + 2-decylteradecanol (58670-89-6) → 11-(((2,3-dimethylbutan-2-yl)oxy)methyl)tricosane

Conditions	Yield
With Amberlyst 15 resin at 80℃; for 24h;	68%

(+/-)-2-methyl-1-butanol (137-32-6) + 2-decylteradecanol (58670-89-6) → C34H70O2

Conditions	Yield
With Amberlyst 15 Molecular sieve;	68%

2-chloromethyl-3-chloroprop-1-ene (1871-57-4) + 2-decylteradecanol (58670-89-6) → 11-((2-((2-decyltetradecyloxy)methyl)allyloxy)methyl)tricosane (1451040-26-8)

Conditions	Yield
Stage #1: 2-chloromethyl-3-chloroprop-1-ene With sodium hydride In tetrahydrofuran; mineral oil Inert atmosphere; Stage #2: 2-decylteradecanol for 96h; Inert atmosphere; Reflux;	66%

2-decylteradecanol (58670-89-6) + isovaleraldehyde (590-86-3) → C53H108O2

Conditions	Yield
With Amberlyst 15 resin Molecular sieve;	65%

2-decylteradecanol (58670-89-6) + C80H80N2O4 (1335223-99-8) → C126H172N2O4 (1335224-01-5)

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 25℃; for 12h; Inert atmosphere;	63%

2-decylteradecanol (58670-89-6) + C88H96N2O4 (1335224-00-4) → C134H188N2O4 (1335224-02-6)

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 25℃; for 12h; Inert atmosphere;	63%

Upstream product

• 112-54-9 Dodecanal 
• 100-51-6 benzyl alcohol 
• 112-53-8 1-dodecyl alcohol 

Downstream Products

• 1609380-31-5 1,3,5-tribromo-2-((2-decyltetradecyl)oxy)benzene 
• 1609380-33-7 ((2-((2-decyltetradecyl)oxy)benzene-1,3,5-triyl)-tris(ethyne-2,1-diyl))tris(trimethylsilane) 
• 126257-84-9 2-decyltetradecyl 9(Z)-octadecenoate 
• 93778-52-0 2-decyltetradecanoic acid 
• 112-41-4 1-dodecene 
• 4542-57-8 dilauryl ether 
• 51732-26-4 11-methylidenetricosane 

Relevant articles and documents

Synthetic base stock based on Guerbet alcohols

Guerbet (β branched) alcohols of varying chain length of even carbon numbers were synthesized by using single linear fatty alcohols ranging from 1-octanol to 1-dodecanol. All Guerbet alcohols having fewer than 28 carbon atoms and are liquid at 0 °C due to β branching. Synthetic base oils were prepared by reacting commonly available unsaturated fatty acids and dicarboxylic acids with Guerbet alcohols using p-toluenesulfonic acid as a catalyst. These base oils were characterized by physical and tribological properties like viscosity, viscosity index, pour point, flash point, wear scar, weld load, coefficient of friction etc. and compared with commercially available 150 and 500 N base oils.