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1-Nonanol

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1-Nonanol/ˈnoʊnənɒl/ is a straight chain fatty alcohol with nine carbon atoms and the molecular formula CH3(CH2)8OH. It is a colorless oily liquid with a citrus odor similar to citronella oil.

1-Nonanol
Skeletal formula
Space-filling model
Names
Preferred IUPAC name
Nonan-1-ol
Other names
1-Nonanol
Pelargonic alcohol
Nonyl alcohol
n-Nonyl alcohol
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.005.076 Edit this at Wikidata
KEGG
UNII
  • InChI=1S/C9H20O/c1-2-3-4-5-6-7-8-9-10/h10H,2-9H2,1H3 checkY
    Key: ZWRUINPWMLAQRD-UHFFFAOYSA-N checkY
  • InChI=1/C9H20O/c1-2-3-4-5-6-7-8-9-10/h10H,2-9H2,1H3
    Key: ZWRUINPWMLAQRD-UHFFFAOYAC
  • OCCCCCCCCC
  • CCCCCCCCCO
Properties
C9H20O
Molar mass 144.258 g·mol−1
Appearance Colorless liquid
Density 0.83 g/cm3[1]
Melting point −6 °C (21 °F; 267 K)[1]
Boiling point 214 °C (417 °F; 487 K)[1]
0.13 g/L[1]
Hazards
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 96 °C (205 °F; 369 K)
Lethal dose or concentration (LD, LC):
3560 mg/kg (oral, rat)[2]
4680 mg/kg (dermal, rabbit)[2]
Related compounds
Related alcohols
 2-Nonanol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

Nonanol occurs naturally in orange oil. The primary use of nonanol is in the manufacture of artificial lemon oil. Various esters of nonanol, such as nonyl acetate, are used in perfumery and flavors.

Nonanols

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More common than 1-nonanol are its many isomers, including isononyl alcohol, which are typically produced by hydroformylation of octenes. Isomeric octenes are produced by dimerization of butenes. These alcohol mixtures are used as solvents in paints and as precursors to plasticizers.[3]

Toxicity

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The LD50 (oral, rats) is about 2.98 g/kg.[3]

References

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  1. ^ a b c d Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health
  2. ^ a b Opdyke, DL (1973). "Monographs on fragrance raw materials". Food and Cosmetics Toxicology. 11 (1): 95–115. doi:10.1016/0015-6264(73)90065-5. PMID 4716134.
  3. ^ a b Falbe, Jürgen; Bahrmann, Helmut; Lipps, Wolfgang; Mayer, Dieter; Frey, Guido D. (2013). "Alcohols, Aliphatic". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a01_279.pub2. ISBN 978-3-527-30385-4.
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