1-Nonanol
Skeletal formula
Space-filling model
Names
Preferred IUPAC name
Other names
1-Nonanol Pelargonic alcohol Nonyl alcoholn -Nonyl alcohol
Identifiers
CAS Number
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard
100.005.076
KEGG
UNII
InChI=1S/C9H20O/c1-2-3-4-5-6-7-8-9-10/h10H,2-9H2,1H3
Y Key: ZWRUINPWMLAQRD-UHFFFAOYSA-N
Y InChI=1/C9H20O/c1-2-3-4-5-6-7-8-9-10/h10H,2-9H2,1H3
Key: ZWRUINPWMLAQRD-UHFFFAOYAC
Properties
Chemical formula
C 9 H 20 O
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)
Flash point
96 °C (205 °F; 369 K)
Lethal dose or concentration (LD, LC):
LD50 (median dose)
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).
Infobox references
1-Nonanol is a straight chain fatty alcohol with nine carbon atoms and the molecular formula CH3 (CH2 )8 OH. It is a colorless oily liquid with a citrus odor similar to citronella oil.
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
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
The LD50 (oral, rats) is about 2.98 g/kg.[ 3]
References
^ a b c d Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health
^ 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 .
^ 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 .
Alcohols
By consumption
Alcohols found in alcoholic drinks Medical alcohol
Ethchlorvynol
Methylpentynol
Methanol poisoning
Toxic alcohols
Primary alcohols (1°)
Methanol
4-Methylcyclohexanemethanol
Aminomethanol
Cyclohexylmethanol
Methoxymethanol
Methylazoxymethanol
Trifluoromethanol
Ethanol
1-Aminoethanol
2,2,2-Trichloroethanol
2,2,2-Trifluoroethanol
2-(2-Ethoxyethoxy)ethanol
2-(2-Methoxyethoxy)ethanol
2-(2-Methoxyethoxy)ethanol
2-Butoxyethanol
2-Chloroethanol
2-Ethoxyethanol
2-Fluoroethanol
2-Mercaptoethanol
2-Methoxyethanol
Aminoethylethanolamine
Diethylethanolamine
Dimethylethanolamine
Ethanol
Ethanolamine
N ,N -Diisopropylaminoethanol
N -Methylethanolamine
Phenoxyethanol
Tribromoethanol
Butanol Straight-chain saturated C1 — C9 Straight-chain saturated C10 — C19 Straight-chain saturated C20 — C29
1-Icosanol (arachidyl)
1-Heneicosanol
1-Docosanol (behenyl)
1-Tricosanol
1-Tetracosanol (lignoceryl)
1-Pentacosanol
1-Hexacosanol (ceryl)
1-Heptacosanol
1-Octacosanol (cluytyl / montanyl)
1-Nonacosanol
Straight-chain saturated C30 — C39
1-Triacontanol (melissyl / myricyl)
1-Hentriacontanol
1-Dotriacontanol (lacceryl)
1-Tritriacontanol
1-Tetratriacontanol (geddyl)
1-Pentatriacontanol
1-Hexatriacontanol
1-Heptatriacontanol
1-Octatriacontanol
1-Nonatriacontanol
Straight-chain saturated C40 — C49
1-Tetracontanol
1-Hentetracontanol
1-Dotetracontanol
1-Tritetracontanol
1-Tetratetracontanol
1-Pentatetracontanol
1-Hexatetracontanol
1-Heptatetracontanol
1-Octatetracontanol
1-Nonatetracontanol
2-Ethylhexanol
Allyl alcohol
Anisyl alcohol
Benzyl alcohol
Cinnamyl alcohol
Crotyl alcohol
Furfuryl alcohol
Isoamyl alcohol
Neopentyl alcohol
Nicotinyl alcohol
Perillyl alcohol
Phenethyl alcohol
Prenol
Propargyl alcohol
Salicyl alcohol
Tryptophol
Vanillyl alcohol
Veratrole alcohol Secondary alcohols (2°) Tertiary alcohols (3°) Hydric alcohols
Monohydric alcohols Dihydric alcohols
Ethylene glycol
Propylene glycol
Trihydric alcohols Polyhydric alcohols (sugar alcohols)
Pentaerythritol
Ethylene glycol (C2 )
Glycerol , Propylene glycol (C3 )
Erythritol , Threitol (C4 )
Xylitol (C5 )
Mannitol, Sorbitol (C6 )
Volemitol (C7 )
Amyl alcohols Aromatic alcohols
Benzyl alcohol
2,4-Dichlorobenzyl alcohol
3-Nitrobenzyl alcohol
Saturated fatty alcohols Branched and unsaturated fatty alcohols Sugar alcohols
C1 — C7
Methylene glycol (C1 )
Ethylene glycol (C2 )
Glycerol (C3 )
Erythritol (C4 )
Threitol (C4 )
Arabitol (C5 )
Ribitol (C5 )
Xylitol (C5 )
Mannitol (C6 )
Sorbitol (C6 )
Galactitol (C6 )
Iditol (C6 )
Volemitol (C7 )
Deoxy sugar alcohols Cyclic sugar alcohols Glycylglycitols
Maltitol
Lactitol
Isomalt
Maltotriitol
Maltotetraitol
Polyglycitol
Terpene alcohols
Monoterpene alcohols
Borneol
Citronellol
Geraniol
Linalool
Menthol
Nerol
Rhodinol
Terpineol
Sesquiterpene alcohols Diterpene alcohols
Dialcohols
1,4-Butanediol
1,5-Pentanediol
2-Methyl-2-propyl-1,3-propanediol
Diethylpropanediol
Ethylene glycol
Trialcohols Sterols Fluoroalcohols
1,3-Difluoro-2-propanol
2,2,2-Trifluoroethanol
2-Fluoroethanol
Nonafluoro-tert -butyl alcohol
Trifluoromethanol
Preparations
Substitution of haloalkane
Carbonyl reduction
Ether cleavage
Hydrolysis of epoxide
Hydration of alkene
Ziegler process
Reactions
Deprotonation
Protonation
Alcohol oxidation
Nucleophilic substitution
Fischer–Speier esterification
Williamson ether synthesis
Elimination reaction
Nucleophilic substitution of carbonyl group
Friedel-Crafts alkylation
Nucleophilic conjugate addition
Transesterification
Category