2-Octanol

2-Octanol (octan-2-ol, 2-OH) is an organic compound with the chemical formula CH₃CH(OH)(CH₂)₅CH₃. It is a colorless oily liquid that is poorly soluble in water but soluble in most organic solvents. 2-Octanol is classified fatty alcohol. A secondary alcohol, it is chiral.

2-Octanol

Skeletal formula
Names
Preferred IUPAC name Octan-2-ol
Other names 2-Octanol 2-Octyl alcohol 1-Methyl-1-heptanol sec-Capryl alcohol Methylhexylcarbinol sec-Caprylic alcohol
Identifiers
CAS Number	123-96-6 Y
3D model (JSmol)	Interactive image
Beilstein Reference	1719322
ChEBI	CHEBI:37869
ChEMBL	ChEMBL510068
ChemSpider	18920
ECHA InfoCard	100.004.244
EC Number	204-667-0
Gmelin Reference	131016
PubChem CID	20083
RTECS number	RH0795000
UNII	66B0DD5E40 Y
CompTox Dashboard (EPA)	DTXSID0027014
InChI InChI=1S/C20H30N7O16P3/c21-9-2-1-3-26(4-9)19-15(30)13(28)10(40-19)5-38-45(34,35)43-46(36,37)39-6-11-14(29)16(42-44(31,32)33)20(41-11)27-8-25-12-17(22)23-7-24-18(12)27/h1,3-4,7-8,10-11,13-16,19-20,28-30H,2,5-6,21H2,(H,34,35)(H,36,37)(H2,22,23,24)(H2,31,32,33) Key: IMPUPYZMUDSKSF-UHFFFAOYSA-N InChI=1/C20H30N7O16P3/c21-9-2-1-3-26(4-9)19-15(30)13(28)10(40-19)5-38-45(34,35)43-46(36,37)39-6-11-14(29)16(42-44(31,32)33)20(41-11)27-8-25-12-17(22)23-7-24-18(12)27/h1,3-4,7-8,10-11,13-16,19-20,28-30H,2,5-6,21H2,(H,34,35)(H,36,37)(H2,22,23,24)(H2,31,32,33) Key: IMPUPYZMUDSKSF-UHFFFAOYAA
SMILES CC(O)CCCCCC
Properties
Chemical formula	C8H18O
Molar mass	130.231 g·mol−1
Appearance	Colourless liquid with characteristic odour[1]
Density	0.820 7 (g/cm3) (20°C)[2]
Melting point	−38 °C (−36 °F; 235 K)[3]
Boiling point	178.5 °C (353.3 °F; 451.6 K)[3]
Solubility in water	1.120 g/L[4]
log P	2.9[4]
Vapor pressure	0.031 mbar (20 °C) 0.11 mbar (30 °C) 0.9 mbar (50 °C)[4]
Henry's law constant (kH)	1.23·10−4 atm-m3/mol[4]
Refractive index (nD)	1.426 (20 °C)[5]
Viscosity	6.2 cP[6]
Thermochemistry
Heat capacity (C)	330.1 (J/mol*K) (298.5K)[1]
Hazards
Occupational safety and health (OHS/OSH):
Eye hazards	2[4]
Skin hazards	2[4]
GHS labelling:[4]
Pictograms
Signal word	Warning
Hazard statements	H226, H315, H319, H411, H412
Precautionary statements	P210, P233, P240, P241, P242, P243, P273, P280, P303+P361+P353, P305+P351+P338, P370+P378, P391, P403+P235, P501
NFPA 704 (fire diamond)	1 2 0
Flash point	71 °C (160 °F; 344 K)[4]
Autoignition temperature	265 °C (509 °F; 538 K)[4]
Explosive limits	0.8 % v/v (lower) 7.4 % v/v (upper)[4]
Lethal dose or concentration (LD, LC):
LD50 (median dose)	>3.2 g/kg (rat, oral) 4 g/kg (mouse, oral)[7]
Safety data sheet (SDS)	Flinn Scientific
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Production

2-Octanol is produced commercially by base-cleavage of ricinoleic acid.^[8] The coproduct is a mixture of sebacic acid ((C₈H₁₆CO₂H)₂). Castor oil, which consists mainly of triglycerides of ricinoleic acid, is the main feedstock.^[9][10]

Uses

2-Octanol is mainly used as:

• Flavor^{[7][11][12][13]}
• low-volatility solvent : Diverses Resins (Paints & Coatings, Adhesives, Inks, etc.), Agrochemicals, Mineral Extraction, etc....^{[14][15][16][17]}
• Defoaming agent : Pulp & Paper, Oil & Gas, Cement, Coatings, Coal, etc.
• a frother in mineral flotation^[18]
• wetting agent

It can also be used as a chemical intermediate for production of various other chemicals:

• Surfactants (ethoxylates, sulfates, ether sulfates, etc.),
• Cosmetic emollients esters (palmitate, adipate, maleate, stearate, myristate, etc.),^[19]
• Plasticizers (acrylates, maleates, etc.),
• Pesticides: Dinocap ^[20][21]
• Lubricants: Zinc dithiophosphate (ZDDP)
• Fragrances (salicylate)
• Used in the manufacturing of perfumes and disinfectant soaps^[22]
• Used to prevent foaming and as a solvent for fats and waxes^[22]
• Used to examine and control Essential Tremor and other types of involuntary neurological tremors^[22]

See also

• 1-Octanol