2726-73-0

Basic information

• Product Name: 1,12-OCTADECANEDIOL
• Synonyms: 1,12-DIHYDROXYOCTADECANE;1,12-OCTADECANEDIOL;12-HYDROXYSTEARYL ALCOHOL;octadecane-1,12-diol;12-HYDROXYSTEARYL ALCOHOL 85%;1,12-OCTADECANEDIOL 85%;1,12-Octadecandiol;Alfol A
• CAS NO: 2726-73-0
• Molecular Formula: C₁₈H₃₈O₂
• Molecular Weight: 286.49
• EINECS: 220-342-6
• Mol File: 2726-73-0.mol
• Article Data: 6

Chemical Properties

• Melting Point: 79.5-80℃
• Boiling Point: 387.5°Cat760mmHg
• Flash Point: 163.5°C
• Appearance: /
• Density: 0.892g/cm³
• Vapor Pressure: 1.33E-07mmHg at 25°C
• Refractive Index: 1.463
• PKA: 15.20±0.10(Predicted)
• Water Solubility: 35.01μg/L at 20℃
• CAS DataBase Reference: 1,12-OCTADECANEDIOL(CAS DataBase Reference)
• NIST Chemistry Reference: 1,12-OCTADECANEDIOL(2726-73-0)
• EPA Substance Registry System: 1,12-OCTADECANEDIOL(2726-73-0)

Safety Data

• Hazardous Substances Data: 2726-73-0(Hazardous Substances Data)

Usage

Flammability and Explosibility

Nonflammable

InChI:InChI=1/C18H38O2/c1-2-3-4-12-15-18(20)16-13-10-8-6-5-7-9-11-14-17-19/h18-20H,2-17H2,1H3

Synthetic route

1,12-diacetoxy-octadecane (20295-02-7) → 1,12-octadecanediol (2726-73-0) + acetic acid 1-hexyl-12-hydroxy-dodecyl ester

Conditions	Yield
With ytterbium(III) triflate In isopropyl alcohol for 30h; Deacetylation; Heating;	A 23% B 69%

12-Hydroxystearic acid (106-14-9) → 1,12-octadecanediol (2726-73-0)

Conditions	Yield
With lithium aluminium tetrahydride In diethyl ether at -10 - 20℃; for 20h; Inert atmosphere;	66%
With lithium aluminium tetrahydride Inert atmosphere;

12-hydroxyoctadecanal (109555-62-6) → 1,12-octadecanediol (2726-73-0)

Conditions	Yield
With barium copper chromite at 260℃; Hydrogenation.unter Druck;
With barium copper chromite at 260℃; Hydrogenation.unter Druck;

Ricinoleic acid (141-22-0) → 1,12-octadecanediol (2726-73-0)

Conditions	Yield
Hydrogenation;
With cobalt at 220 - 230℃; under 147102 - 220652 Torr; Hydrogenation;
With copper chromite at 250℃; under 147102 - 220652 Torr; Hydrogenation;

castor oil → 1,12-octadecanediol (2726-73-0)

Conditions	Yield
With copper chromite at 250℃; under 147102 - 220652 Torr; Hydrogenation;
With copper at 350℃; under 147102 - 220652 Torr; Hydrogenation;
With cobalt at 220 - 230℃; under 147102 - 220652 Torr; Hydrogenation;

ethyl ricinoleate (55066-53-0) + copper + kieselguhr → 1,12-octadecanediol (2726-73-0)

Conditions	Yield
at 350℃; under 73550.8 - 147102 Torr; Hydrogenation;

ethanol (64-17-5) + 1,12-octadecanediol (2726-73-0) → 18-hydroxy-octadecan-7-one (66978-66-3) + methyl 12-oxooctadecanoate (2380-27-0) + ethyl 12-oxo-octadecanoate (88472-61-1) + 12-oxo-octadecanal + 13-chloro-1-hydroxy-12-octadecanone + 1,1-dimethoxy-12-octadecanone

Conditions	Yield
With trichloroisocyanuric acid; sodium hydrogencarbonate; trichloroacetic acid In methanol; acetone at 10℃; for 0.25h; Product distribution;	A 93.3% B 2.4% C 0.4% D 0.4% E n/a F 0.3%

1,12-octadecanediol (2726-73-0) → 12-hydroxyoctadecanal (109555-62-6)

Conditions	Yield
With sodium hypochlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; tetrabutylammomium bromide; sodium hydrogencarbonate; potassium bromide In dichloromethane; water at 0℃; for 0.333333h; Reagent/catalyst; Inert atmosphere;	93%
With [bis(acetoxy)iodo]benzene; 1,5-dimethyl-9-azanoradamantane N-oxyl In dichloromethane at 20℃; for 2h; Catalytic behavior; Reagent/catalyst;	79%

1,12-octadecanediol (2726-73-0) → 12-hydroxyoctadecanal (109555-62-6) + 12-oxo-octadecanal

Conditions	Yield
With sodium hypochlorite; 1,5-dimethyl-9-azanoradamantane N-oxyl; tetrabutylammomium bromide; sodium hydrogencarbonate; potassium bromide In dichloromethane; water at 0℃; for 0.25h;	A 89% B 7%

1,12-octadecanediol (2726-73-0) → (7RS)-18-bromooctadecan-7-ol

Conditions	Yield
With carbon tetrabromide; triphenylphosphine In dichloromethane at 10℃; for 20h;	73%

1,12-octadecanediol (2726-73-0) + phenol (108-95-2) → 2-(12-hydroxyoctadecyl)phenol

Conditions	Yield
With palladium on activated carbon; lithium tert-butoxide In toluene at 160℃; for 24h; Sealed tube; Inert atmosphere; chemoselective reaction;	70%

1,12-octadecanediol (2726-73-0) + 2-diethylamino-4,4,7,7-tetramethyl-1,3,2-dioxaphosphepane (261920-18-7) → 1,12-octadecanediol 1-(4,4,7,7-tetramethylbutylene phosphate) + C34H68O8P2

Conditions	Yield
Stage #1: 1,12-octadecanediol; 2-diethylamino-4,4,7,7-tetramethyl-1,3,2-dioxaphosphepane With 1H-tetrazole In dichloromethane at 0℃; for 6.5h; Substitution; Stage #2: With 3-chloro-benzenecarboperoxoic acid at -78 - 20℃; for 0.5h; Oxidation;	A 69% B 10%

1,12-octadecanediol (2726-73-0) + cyclohexanone (108-94-1) → 2-(12-hydroxyoctadecyl)phenol

Conditions	Yield
With palladium 10% on activated carbon; lithium tert-butoxide In toluene at 160℃; for 24h; Microwave irradiation; Sealed tube;	66%

1,12-octadecanediol (2726-73-0) + epichlorohydrin (106-89-8) → 12-hydroxyoctadecyl glycidyl ether

Conditions	Yield
With sodium hydroxide; tetrabutyl-ammonium chloride In tetrahydrofuran; water; toluene	45%

phosgene (75-44-5) + 1,12-octadecanediol (2726-73-0) → 3-hexyl-2,15-dioxa-hexadecanedioic acid diamide

Conditions	Yield
With benzene und Behandeln der Reaktionsloesung mit Ammoniak;

n-dodecanoyl chloride (112-16-3) + 1,12-octadecanediol (2726-73-0) → 1,12-bis-lauroyloxy-octadecane

1,12-octadecanediol (2726-73-0) → heptadecan-7-one (6064-42-2)

Conditions	Yield
With nickel at 185 - 270℃; unter Wasserstoffdruck;
With palladium on activated charcoal at 185 - 270℃; unter Wasserstoffdruck;

1,12-octadecanediol (2726-73-0) → 18-hydroxy-octadecan-7-one (66978-66-3)

Conditions	Yield
With nickel kieselguhr at 200 - 240℃;

1,12-octadecanediol (2726-73-0) → hepatdecane (629-78-7)

Conditions	Yield
With hydrogen; nickel at 250℃; under 73550.8 - 147102 Torr;

1,12-octadecanediol (2726-73-0) → 7-heptadecanol (93658-33-4)

Conditions	Yield
With nickel kieselguhr at 250℃; anschliessenden Hydrieren des Reaktionsgemisches bei 150-175grad und 105 at;

1,12-octadecanediol (2726-73-0) → 18-chloro-octadecan-7-ol

Conditions	Yield
With pyridine; thionyl chloride

1,12-octadecanediol (2726-73-0) → 1,12-bis-sulfooxy-octadecane (30913-02-1)

Conditions	Yield
With chlorosulfonic acid at 30℃;
With tetrachloromethane; chlorosulfonic acid at 35℃;
With chlorosulfonic acid; acetic acid ester

1,12-octadecanediol (2726-73-0) + acetic anhydride (108-24-7) → 1,12-diacetoxy-octadecane (20295-02-7)

1,12-octadecanediol (2726-73-0) + acrylonitrile (107-13-1) → 5-hexyl-4,17-dioxa-eicosanedinitrile (5299-51-4)

Conditions	Yield
With 1,4-dioxane; water; N-benzyl-trimethylammonium hydroxide

1,12-octadecanediol (2726-73-0) + Stearoyl chloride (112-76-5) → 1,12-bis-stearoyloxy-octadecane (54684-77-4)

1,12-octadecanediol (2726-73-0) + acetylene (74-86-2) → 18-vinyloxy-octadecan-7-ol (110877-03-7)

Conditions	Yield
With potassium hydroxide at 180℃;

1,12-octadecanediol (2726-73-0) + acetylene (74-86-2) → 1,12-bis-vinyloxy-octadecane (10403-71-1)

Conditions	Yield
With potassium hydroxide at 160 - 180℃; unter Druck;

1,12-octadecanediol (2726-73-0) + nickel kieselguhr → heptadecan-7-one (6064-42-2)

Conditions	Yield
je nach den Bedingungen;

1,12-octadecanediol (2726-73-0) + nickel kieselguhr → 18-hydroxy-octadecan-7-one (66978-66-3)

Conditions	Yield
je nach den Bedingungen;

Upstream product

• 106-14-9 12-Hydroxystearic acid 
• 55066-53-0 ethyl ricinoleate 
• 20295-02-7 1,12-diacetoxy-octadecane 
• 141-22-0 Ricinoleic acid 
• 109555-62-6 12-hydroxyoctadecanal 
• 540-11-4 (9Z,12R)-octadec-9-ene-1,12-diol 

Downstream Products

• 102155-52-2 18-ethoxy-octadecan-7-ol 
• 85480-95-1 1,12-bis-docosanoyloxy-octadecane 
• 6064-42-2 heptadecan-7-one 
• 10403-71-1 1,12-octadecanediol divinyl ether 
• 629-78-7 hepatdecane 

Relevant articles and documents

Synthesis and aggregation behaviour of single-chain, 1,32-alkyl branched bis(phosphocholines): Effect of lateral chain length

Three novel single-chain bis(phosphocholines) bearing two lateral alkyl chains of variable length next to the headgroup have been synthesized as model lipids for naturally occurring archaeal membrane lipids. The synthesis was realized using the Cu-catalyzed Grignard bis-coupling reaction of a primary bromide as a side part and a 1,ω-dibromide as a centre part. We could show that the aggregation behaviour of the resulting bolalipids strongly depends on the length of the lateral alkyl chain: the C3-branched bolalipid self-assembles into lamellar sheets, whereas the C6- and C9-analogues form nanofibres. The lamella-forming bolalipids could be used in the future to prepare stable and tailored liposomes for oral drug delivery.

Visible-Light-Driven Dehydrogenative Coupling of Primary Alcohols with Phenols Forming Aryl Carboxylates

A preparative method for obtaining aryl esters from aliphatic primary alcohols and phenols was developed. The reaction proceeds under the irradiation of visible light at ambient temperature, dispensing with any oxidant or hydrogen acceptor. Primary alcohols having a variety of functional groups are successfully esterified with phenols. The produced esters can be utilized as the precursor of various carbonyl compounds.

Ytterbium triflate mediated selective deprotection of acetates

Ytterbium triflate mediated selective deprotection of acetates in isopropyl alcohol at reflux temperature is reported. Unlike hafnium triflate, under the present reaction conditions aryl acetates also undergo deacetylation instead of Fries migration.