2-Butanol

2-Butanol
Names
	Preferred IUPAC name Butan-2-ol
	Other names sec-Butanol; sec-Butyl alcohol; 2-Butanol; 2-Butyl alcohol
Identifiers
CAS Number	78-92-2 ; 14898-79-4 (R) ; 4221-99-2 (S) ;
3D model (JSmol)	Interactive image;
Beilstein Reference	773649; 1718764 (R); 1718763 (S)
ChEBI	CHEBI:35687 ;
ChEMBL	ChEMBL45462 ;
ChemSpider	6320 ; 76392 (R) ; 392543 (S) ;
DrugBank	DB02606 ;
ECHA InfoCard	100.001.053
EC Number	201-158-5;
Gmelin Reference	1686; 396584 (R); 25655 (S)
MeSH	2-butanol
PubChem CID	6568; 84682 (R); 444683 (S);
RTECS number	EO1750000;
UNII	0TUL3ENK62 ; DLH38K423J (R) ; 69KXU5NDTO (S) ;
UN number	1120
CompTox Dashboard (EPA)	DTXSID9021762 ;
	InChI InChI=1S/C4H10O/c1-3-4(2)5/h4-5H,3H2,1-2H3 Key: BTANRVKWQNVYAZ-UHFFFAOYSA-N ;
	SMILES CCC(C)O;
Properties
Chemical formula	C4H10O
Molar mass	74.123 g·mol−1
Density	0.808 g cm−3
Melting point	−115 °C; −175 °F; 158 K
Boiling point	98 to 100 °C; 208 to 212 °F; 371 to 373 K
Solubility in water	390 g/L
log P	0.683
Vapor pressure	1.67 kPa (at 20 °C)
Acidity (pKa)	17.6
Magnetic susceptibility (χ)	−5.7683×10−5 cm3 mol−1
Refractive index (nD)	1.3978 (at 20 °C)
Thermochemistry
Heat capacity (C)	197.1 J K−1 mol−1
Std molar; entropy (S⦵298)	213.1 J K−1 mol−1
Std enthalpy of; formation (ΔfH⦵298)	−343.3 to −342.1 kJ mol−1
Std enthalpy of; combustion (ΔcH⦵298)	−2.6611 to −2.6601 MJ mol−1
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H226, H319, H335, H336
Precautionary statements	P261, P305+P351+P338
NFPA 704 (fire diamond)	1 3 0
Flash point	22 to 27 °C (72 to 81 °F; 295 to 300 K)
Autoignition; temperature	405 °C (761 °F; 678 K)
Explosive limits	1.7–9.8%
	Lethal dose or concentration (LD, LC):
LCLo (lowest published)	16,000 ppm (rat, 4 hr); 10,670 ppm (mouse, 3.75 hr); 16,000 ppm (mouse, 2.67 hr)
	NIOSH (US health exposure limits):
PEL (Permissible)	TWA 150 ppm (450 mg/m3)
REL (Recommended)	TWA 100 ppm (305 mg/m3) ST 150 ppm (455 mg/m3)
IDLH (Immediate danger)	2000 ppm
Safety data sheet (SDS)	inchem.org
Related compounds
Related butanols	n-Butanol; Isobutanol; tert-Butanol
Related compounds	Butanone
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Butan-2-ol, or sec-butanol, is an organic compound with formula CH₃CH(OH)CH₂CH₃. Its structural isomers are 1-butanol, isobutanol, and tert-butanol. 2-Butanol is chiral and thus can be obtained as either of two stereoisomers designated as (R)-(−)-butan-2-ol and (S)-(+)-butan-2-ol. It is normally encountered as a 1:1 mixture of the two stereoisomers — a racemic mixture.

This secondary alcohol is a flammable, colorless liquid that is soluble in three parts water and completely miscible with organic solvents. It is produced on a large scale, primarily as a precursor to the industrial solvent methyl ethyl ketone.



(R)-(−)-2-butanol	(S)-(+)-2-butanol

^ "Alcohols Rule C-201.1". Nomenclature of Organic Chemistry (The IUPAC 'Blue Book'), Sections A, B, C, D, E, F, and H. Oxford: Pergamon Press. 1979. Designations such as isopropanol, sec-butanol, and tert-butanol are incorrect because there are no hydrocarbons isopropane, sec-butane, and tert-butane to which the suffix "-ol" can be added; such names should be abandoned. Isopropyl alcohol, sec-butyl alcohol, and tert-butyl alcohol are, however, permissible (see Rule C-201.3) because the radicals isopropyl, sec-butyl, and tert-butyl do exist
^ "2-butanol - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 26 March 2005. Identification and Related Records. Retrieved 12 October 2011.
^ Alger, Donald B. (November 1991). "The water solubility of butan-2-ol: A widespread error". Journal of Chemical Education. 68 (11): 939. Bibcode:1991JChEd..68..939A. doi:10.1021/ed068p939.1.
^ Serjeant, E.P., Dempsey B.; Ionisation Constants of Organic Acids in Aqueous Solution. International Union of Pure and Applied Chemistry (IUPAC). IUPAC Chemical Data Series No. 23, 1979. New York, New York: Pergamon Press, Inc., p. 989
^ ^a ^b ^c ^d NIOSH Pocket Guide to Chemical Hazards. "#0077". National Institute for Occupational Safety and Health (NIOSH).

[iupac1979-1] "Alcohols Rule C-201.1". Nomenclature of Organic Chemistry (The IUPAC 'Blue Book'), Sections A, B, C, D, E, F, and H. Oxford: Pergamon Press. 1979. Designations such as isopropanol, sec-butanol, and tert-butanol are incorrect because there are no hydrocarbons isopropane, sec-butane, and tert-butane to which the suffix "-ol" can be added; such names should be abandoned. Isopropyl alcohol, sec-butyl alcohol, and tert-butyl alcohol are, however, permissible (see Rule C-201.3) because the radicals isopropyl, sec-butyl, and tert-butyl do exist

[2] "2-butanol - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 26 March 2005. Identification and Related Records. Retrieved 12 October 2011.

[Journal_of_Chemical_Education-3] Alger, Donald B. (November 1991). "The water solubility of butan-2-ol: A widespread error". Journal of Chemical Education. 68 (11): 939. Bibcode:1991JChEd..68..939A. doi:10.1021/ed068p939.1.

[4] Serjeant, E.P., Dempsey B.; Ionisation Constants of Organic Acids in Aqueous Solution. International Union of Pure and Applied Chemistry (IUPAC). IUPAC Chemical Data Series No. 23, 1979. New York, New York: Pergamon Press, Inc., p. 989

[PGCH-5] NIOSH Pocket Guide to Chemical Hazards. "#0077". National Institute for Occupational Safety and Health (NIOSH).

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