2-Ethylhexanol

2-Ethylhexanol
Skeletal formula of 2-ethylhexanol
2-Ethylhexanol molecule
Names
Preferred IUPAC name
2-Ethylhexan-1-ol[1]
Other names
isooctyl alcohol, 2-ethylhexanol
Identifiers
3D model (JSmol)
1719280
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.002.941 Edit this at Wikidata
EC Number
  • 203-234-3
KEGG
MeSH 2-ethylhexanol
UNII
  • InChI=1S/C8H18O/c1-3-5-6-8(4-2)7-9/h8-9H,3-7H2,1-2H3 checkY
    Key: YIWUKEYIRIRTPP-UHFFFAOYSA-N checkY
  • CCCCC(CC)CO
Properties
CH3CH2CH2CH2CH(CH2CH3)CH2OH
Molar mass 130.231 g·mol−1
Appearance Colourless liquid
Density 833 mg/mL
Melting point −76 °C (−105 °F; 197 K)
Boiling point 180 to 186 °C; 356 to 367 °F; 453 to 459 K
log P 2.721
Vapor pressure 30 Pa (at 20 °C)
1.431
Thermochemistry
317.5 J/(K·mol)
347.0 J/(K·mol)
−433.67–−432.09 kJ/mol
−5.28857–−5.28699 MJ/mol
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
Mildly toxic
GHS labelling:
GHS07: Exclamation mark
Danger
H302, H312, H315, H318, H335
P261, P280, P305+P351+P338
Flash point 81 °C (178 °F; 354 K)
290 °C (554 °F; 563 K)
Explosive limits 0.88–9.7%
Lethal dose or concentration (LD, LC):
  • 1.97 g/kg (dermal, rabbit)
  • 3.73 g/kg (oral, rat)
NIOSH (US health exposure limits):
PEL (Permissible)
none[2]
REL (Recommended)
TWA 50 ppm (270 mg/m3) (skin)[2]
IDLH (Immediate danger)
N.D.[2]
Related compounds
Related alkanol
Propylheptyl alcohol
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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2-Ethylhexanol (abbreviated 2-EH) is an organic compound with the chemical formula CH3CH2CH2CH2CH(CH2CH3)CH2OH. It is a branched, eight-carbon chiral alcohol. It is a colorless liquid that is poorly soluble in water but soluble in most organic solvents. It is produced on a large scale (>2,000,000,000 kg/y) for use in numerous applications such as solvents, flavors, and fragrances and especially as a precursor for production of other chemicals such as emollients and plasticizers.[3] It is encountered in plants, fruits, and wines.[4][5] The odor has been reported as "heavy, earthy, and slightly floral" for the R enantiomer and "a light, sweet floral fragrance" for the S enantiomer.[6][7]

  1. ^ "2-ethylhexanol - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 16 September 2005. Identification and Related Records. Retrieved 29 January 2012.
  2. ^ a b c NIOSH Pocket Guide to Chemical Hazards. "#0354". National Institute for Occupational Safety and Health (NIOSH).
  3. ^ Cite error: The named reference ROH was invoked but never defined (see the help page).
  4. ^ Fan, Wenlai; Qian, Michael C. (2006). "Characterization of Aroma Compounds of Chinese "Wuliangye" and "Jiannanchun" Liquors by Aroma Extract Dilution Analysis". Journal of Agricultural and Food Chemistry. 54 (7): 2695–2704. doi:10.1021/jf052635t. PMID 16569063.
  5. ^ Mayuoni-Kirshinbaum, Lina; Tietel, Zipora; Porat, Ron; Ulrich, Detlef (2012). "Identification of aroma-active compounds in 'wonderful' pomegranate fruit using solvent-assisted flavour evaporation and headspace solid-phase micro-extraction methods". European Food Research and Technology. 235 (2): 277–283. doi:10.1007/s00217-012-1757-0. S2CID 97102092.
  6. ^ Klaus Rettinger; Christian Burschka; Peter Scheeben; Heike Fuchs; Armin Mosandl (1991). "Chiral 2-alkylbranched acids, esters and alcohols. Preparation and stereospecific flavour evaluation" (PDF). Tetrahedron: Asymmetry. 2 (10): 965–968. doi:10.1016/S0957-4166(00)86137-6.
  7. ^ McGinty, D.; Scognamiglio, J.; Letizia, C.S.; Api, A.M. (2010). "Fragrance material review on 2-ethyl-1-hexanol". Food and Chemical Toxicology. 48: S115–S129. doi:10.1016/j.fct.2010.05.042. PMID 20659633.