1-Nonanol
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Names
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Preferred IUPAC name
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Other names
1-Nonanol Pelargonic alcohol Nonyl alcohol n-Nonyl alcohol
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Identifiers
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CAS Number
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ChEBI
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ChEMBL
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ChemSpider
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DrugBank
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ECHA InfoCard
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100.005.076
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KEGG
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UNII
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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
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Properties
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Chemical formula
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C9H20O
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Molar mass
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144.258 g·mol−1
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Appearance
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Colorless liquid
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Density
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0.83 g/cm3[1]
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Melting point
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−6 °C (21 °F; 267 K)[1]
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Boiling point
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214 °C (417 °F; 487 K)[1]
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0.13 g/L[1]
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Hazards
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NFPA 704 (fire diamond)
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Flash point
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96 °C (205 °F; 369 K)
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Lethal dose or concentration (LD, LC):
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LD50 (median dose)
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3560 mg/kg (oral, rat)[2] 4680 mg/kg (dermal, rabbit)[2]
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Related compounds
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Related alcohols
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2-Nonanol
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
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1-Nonanol 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.
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 |
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By consumption | Alcohols found in alcoholic drinks | |
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Medical alcohol |
- Ethchlorvynol
- Methylpentynol
- Methanol poisoning
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Toxic alcohols | |
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Primary alcohols (1°) | Methanol |
- 4-Methylcyclohexanemethanol
- Aminomethanol
- Cyclohexylmethanol
- Methoxymethanol
- Methylazoxymethanol
- Trifluoromethanol
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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
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Butanol | |
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Straight-chain saturated C1 — C9 | |
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Straight-chain saturated C10 — C19 | |
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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
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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
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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
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- 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
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Secondary alcohols (2°) | |
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Tertiary alcohols (3°) | |
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Hydric alcohols | Monohydric alcohols | |
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Dihydric alcohols |
- Ethylene glycol
- Propylene glycol
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Trihydric alcohols | |
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Polyhydric alcohols (sugar alcohols) |
- Pentaerythritol
- Ethylene glycol (C2)
- Glycerol, Propylene glycol (C3)
- Erythritol, Threitol (C4)
- Xylitol (C5)
- Mannitol, Sorbitol (C6)
- Volemitol (C7)
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Amyl alcohols | |
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Aromatic alcohols |
- Benzyl alcohol
- 2,4-Dichlorobenzyl alcohol
- 3-Nitrobenzyl alcohol
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Saturated fatty alcohols | |
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Branched and unsaturated fatty alcohols | |
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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)
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Deoxy sugar alcohols | |
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Cyclic sugar alcohols | |
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Glycylglycitols |
- Maltitol
- Lactitol
- Isomalt
- Maltotriitol
- Maltotetraitol
- Polyglycitol
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Terpene alcohols | Monoterpene alcohols |
- Borneol
- Citronellol
- Geraniol
- Linalool
- Menthol
- Nerol
- Rhodinol
- Terpineol
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Sesquiterpene alcohols | |
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Diterpene alcohols | |
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Dialcohols |
- 1,4-Butanediol
- 1,5-Pentanediol
- 2-Methyl-2-propyl-1,3-propanediol
- Diethylpropanediol
- Ethylene glycol
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Trialcohols | |
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Sterols | |
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Fluoroalcohols |
- 1,3-Difluoro-2-propanol
- 2,2,2-Trifluoroethanol
- 2-Fluoroethanol
- Nonafluoro-tert-butyl alcohol
- Trifluoromethanol
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Preparations |
- Substitution of haloalkane
- Carbonyl reduction
- Ether cleavage
- Hydrolysis of epoxide
- Hydration of alkene
- Ziegler process
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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
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