2-Pentanol

2-Pentanol^[1]
Names
	Preferred IUPAC name Pentan-2-ol
	Other names 2-Pentanol; sec-amyl alcohol
Identifiers
CAS Number	6032-29-7 ; 31087-44-2 (R) ; 26184-62-3 (S) ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:77518 ;
ChEMBL	ChEMBL45065 ;
ChemSpider	21011 ;
PubChem CID	22386;
UNII	04G7050365 ;
	InChI InChI=1S/C5H12O/c1-3-4-5(2)6/h5-6H,3-4H2,1-2H3 Key: JYVLIDXNZAXMDK-UHFFFAOYSA-N ; InChI=1/C5H12O/c1-3-4-5(2)6/h5-6H,3-4H2,1-2H3 Key: JYVLIDXNZAXMDK-UHFFFAOYAY;
	SMILES OC(C)CCC;
Properties
Chemical formula	C5H12O
Molar mass	88.148 g/mol
Appearance	colorless liquid
Density	0.812 g/cm3
Melting point	−73 °C (−99 °F; 200 K)
Boiling point	119.3 °C (246.7 °F; 392.4 K)
Solubility in water	45 g/L
Solubility	soluble in ethanol, diethyl ether, carbon tetrachloride, chloroform
Vapor pressure	0.804 kPa
Magnetic susceptibility (χ)	-69.1·10−6 cm3/mol
Viscosity	3.470 mPa·s
Thermochemistry
Heat capacity (C)	2.716 J·g−1·K−1 (liquid)
Std enthalpy of; formation (ΔfH⦵298)	-365.2 kJ·mol−1 (liquid) ; -311.0 kJ·mol−1 (gas)
Hazards
Flash point	34 °C (93 °F; 307 K)
Autoignition; temperature	343 °C (649 °F; 616 K)
Explosive limits	1.2–9%
Related compounds
Related compounds	Amyl alcohol
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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	Infobox references

2-Pentanol (IUPAC name: pentan-2-ol; also called sec-amyl alcohol) is an organic chemical compound. It is used as a solvent and an intermediate in the manufacturing of other chemicals. 2-Pentanol is a component of many mixtures of amyl alcohols sold industrially. 2-Pentanol is chiral and thus can be obtained as either of two stereoisomers designated as (R)-(−)-2-pentanol and (S)-(+)-2-pentanol.

2-Pentanol has been detected in fresh bananas by gas chromatography–mass spectrometry, at an abundance of 14.26±2.63 ppm.^[2]

Reactions

2-Pentanol can be manufactured by hydration of pentene.^[3]

References

↑ Lide, David R. (1998), Handbook of Chemistry and Physics (87 ed.), Boca Raton, Florida: CRC Press, pp. 3-454, 5-42, 6-188, 8-102, 15-23, ISBN 0-8493-0594-2
↑ Jordán, María J.; Tandon, Kawaljit; Shaw, Philip E.; Goodner, Kevin L. (2001), "Aromatic Profile of Aqueous Banana Essence and Banana Fruit by Gas Chromatography−Mass Spectrometry (GC-MS) and Gas Chromatography−Olfactometry (GC-O)", Journal of Agricultural and Food Chemistry 49 (10): 4813–4817, doi:10.1021/jf010471k, PMID 11600027
↑ McKetta, John J.; Cunningham, William Aaron (1977), Encyclopedia of Chemical Processing and Design, 3, Boca Raton, Florida: CRC Press, pp. 280–281, ISBN 978-0-8247-2480-1, https://books.google.com/books?id=iwSU5G5VzO0C&pg=PA279, retrieved 2010-01-17

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Original source: https://en.wikipedia.org/wiki/2-Pentanol. Read more

[hand-1] Lide, David R. (1998), Handbook of Chemistry and Physics (87 ed.), Boca Raton, Florida: CRC Press, pp. 3-454, 5-42, 6-188, 8-102, 15-23, ISBN 0-8493-0594-2

[2] Jordán, María J.; Tandon, Kawaljit; Shaw, Philip E.; Goodner, Kevin L. (2001), "Aromatic Profile of Aqueous Banana Essence and Banana Fruit by Gas Chromatography−Mass Spectrometry (GC-MS) and Gas Chromatography−Olfactometry (GC-O)", Journal of Agricultural and Food Chemistry 49 (10): 4813–4817, doi:10.1021/jf010471k, PMID 11600027

[encyc-3] McKetta, John J.; Cunningham, William Aaron (1977), Encyclopedia of Chemical Processing and Design, 3, Boca Raton, Florida: CRC Press, pp. 280–281, ISBN 978-0-8247-2480-1, https://books.google.com/books?id=iwSU5G5VzO0C&pg=PA279, retrieved 2010-01-17

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v t e Alcohols
Straight-chain primary alcohols (1°)	Methanol (C₁) Ethanol (C₂) 1-Propanol (C₃) n-Butanol (C₄) 1-Pentanol (C₅) 1-Hexanol (C₆) 1-Heptanol (C₇) 1-Octanol (C₈) 1-Nonanol (C₉) 1-Decanol (C₁₀) Undecanol (C₁₁) Dodecanol (C₁₂) Tridecan-1-ol (C₁₃) 1-Tetradecanol (C₁₄) 1-Pentadecanol (C₁₅) Cetyl alcohol (C₁₆) Heptadecan-1-ol (C₁₇) Stearyl alcohol (C₁₈) Nonadecan-1-ol (C₁₉) Arachidyl alcohol (C₂₀) Heneicosan-1-ol (C₂₁) Docosanol (C₂₂) Tricosan-1-ol (C₂₃) 1-Tetracosanol (C₂₄) Pentacosan-1-ol (C₂₅) 1-Hexacosanol (C₂₆) 1-Heptacosanol (C₂₇) 1-Octacosanol (C₂₈) 1-Nonacosanol (C₂₉) Triacontanol (C₃₀) Hentriacontanol (C₃₁) Dotriacontanol (C₃₂) Tritriacontanol (C₃₃) Tetratriacontanol (C₃₄) Pentatriacontanol (C₃₅) Hexatriacontanol (C₃₆) 1-Heptatriacontanol (C₃₇) 1-Octatriacontanol (C₃₈) Nonatriacontan-1-ol (C₃₉) Tetracontanol (C₄₀)
Other primary alcohols	Isobutanol (C₄) Isoamyl alcohol (C₅) 2-Methyl-1-butanol (C₅) Phenethyl alcohol (C₈) Tryptophol (C₁₀)
Secondary alcohols (2°)	Isopropanol (C₃) Cyclopropanol (C₃) 2-Butanol (C₄) 2-Pentanol (C₅) 3-Pentanol (C₅) Cyclopentanol (C₅) 2-Hexanol (C₆) 3-Hexanol (C₆) Pinacolyl alcohol (C₆) Cyclohexanol (C₆) 2-Heptanol (C₇) 3-Heptanol (C₇) 2-Octanol (C₈)
Tertiary alcohols (3°)	tert-Butyl alcohol (C₄) tert-Amyl alcohol (C₅) 2-Methyl-2-pentanol (C₆) 2-Methylhexan-2-ol (C₇) 2-Methylheptan-2-ol (C₈) 3-Methyl-3-pentanol (C₆) 3-Methyloctan-3-ol (C₉)
Preparations	Substitution of haloalkane Carbonyl reduction Ether cleavage Hydrolysis of epoxide Hydration of alkene Ziegler process
Reactions	Deprotonation Protonation Alcohol oxidation Glycol cleavage Nucleophilic substitution Fischer–Speier esterification Williamson ether synthesis Elimination reaction Nucleophilic substitution of carbonyl group Friedel-Crafts alkylation Nucleophilic conjugate addition Transesterification
Category

2-Pentanol

Topic: Chemistry

Reactions

See also

References

Names

Preferred IUPAC name Pentan-2-ol
Other names 2-Pentanol sec-amyl alcohol
Identifiers
CAS Number	6032-29-7^Y 31087-44-2 (R)^Y 26184-62-3 (S)^Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:77518^N
ChEMBL	ChEMBL45065^Y
ChemSpider	21011^Y
PubChem CID	22386
UNII	04G7050365^Y
InChI InChI=1S/C5H12O/c1-3-4-5(2)6/h5-6H,3-4H2,1-2H3^Y Key: JYVLIDXNZAXMDK-UHFFFAOYSA-N^Y InChI=1/C5H12O/c1-3-4-5(2)6/h5-6H,3-4H2,1-2H3 Key: JYVLIDXNZAXMDK-UHFFFAOYAY
SMILES OC(C)CCC
Properties
Chemical formula	C₅H₁₂O
Molar mass	88.148 g/mol
Appearance	colorless liquid
Density	0.812 g/cm³
Melting point	−73 °C (−99 °F; 200 K)
Boiling point	119.3 °C (246.7 °F; 392.4 K)
Solubility in water	45 g/L
Solubility	soluble in ethanol, diethyl ether, carbon tetrachloride, chloroform
Vapor pressure	0.804 kPa
Magnetic susceptibility (χ)	-69.1·10⁻⁶ cm³/mol
Viscosity	3.470 mPa·s
Thermochemistry
Heat capacity (C)	2.716 J·g⁻¹·K⁻¹ (liquid)
Std enthalpy of formation (Δ_fH^⦵₂₉₈)	-365.2 kJ·mol⁻¹ (liquid) -311.0 kJ·mol⁻¹ (gas)
Hazards
Flash point	34 °C (93 °F; 307 K)
Autoignition temperature	343 °C (649 °F; 616 K)
Explosive limits	1.2–9%
Related compounds
Related compounds	Amyl alcohol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is ^YN ?)
Infobox references