2-Octanol

Chemical compound From Wikipedia, the free encyclopedia

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.

Quick facts Names, Identifiers ...
2-Octanol
Skeletal formula
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
3D model (JSmol)
1719322
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.004.244 Edit this at Wikidata
EC Number
  • 204-667-0
131016
RTECS number
  • RH0795000
UNII
  • 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
  • CC(O)CCCCCC
Properties
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]
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]
1.23·10−4 atm-m3/mol[4]
1.426 (20 °C)[5]
Viscosity 6.2 cP[6]
Thermochemistry
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]
GHS02: Flammable GHS07: Exclamation mark GHS09: Environmental hazard
Warning
H226, H315, H319, H411, H412
P210, P233, P240, P241, P242, P243, P273, P280, P303+P361+P353, P305+P351+P338, P370+P378, P391, P403+P235, P501
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineFlammability 2: Must be moderately heated or exposed to relatively high ambient temperature before ignition can occur. Flash point between 38 and 93 °C (100 and 200 °F). E.g. diesel fuelInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
1
2
0
Flash point 71 °C (160 °F; 344 K)[4]
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):
>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).
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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

It is a precursor to 2-octyl cyanoacrylate, a version of superglue used as a wound closure adhesive.[11] It is closely related to octyl cyanoacrylate. The use of 2-octyl cyanoacrylate was approved in 1998; offered as an alternative to stitches, sutures, and or adhesive strips.[12]

2-Octanol is also used as:

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

See also

Notes

References

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