Sec-butanol

2-Butanol

Names
IUPAC name Butan-2-ol
Other names sec-Butanol sec-Butyl alcohol, 2-Butanol 2-Butyl alcohol
Identifiers
CAS Number	78-92-2 Y 14898-79-4 (R) Y 4221-99-2 (S) Y
3D model (JSmol)	Interactive image
Beilstein Reference	773649 1718764 (R) 1718763 (S)
ChEBI	CHEBI:35687 Y
ChemSpider	6320 Y 76392 (R) Y 392543 (S) Y
DrugBank	DB02606 Y
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
UN number	1120
InChI InChI=1S/C4H10O/c1-3-4(2)5/h4-5H,3H2,1-2H3 Y Key: BTANRVKWQNVYAZ-UHFFFAOYSA-N Y
SMILES CCC(C)O
Properties
Chemical formula	C4H10O
Molar mass	74.12 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	290 g/kg
log P	0.683
Vapor pressure	1.67 kPa (at 20 °C)
Magnetic susceptibility (χ)	-57.683·10−6 cm3/mol
Refractive index (nD)	1.3978 (at 20 °C)
Thermochemistry
Specific heat capacity (C)	197.1 J K−1 mol−1
Std molar entropy (So298)	213.1 J K−1 mol−1
Std enthalpy of formation (ΔfHo298)	−343.3–−342.1 kJ mol−1
Std enthalpy of combustion (ΔcHo298)	−2.6611–−2.6601 MJ mol−1
Hazards
Safety data sheet	inchem.org
GHS pictograms
GHS signal word	WARNING
GHS hazard statements	H226, H319, H335, H336
GHS precautionary statements	P261, P305+351+338
NFPA 704	3 1 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)
US health exposure limits (NIOSH):
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
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).
Y  (what is YN ?)
Infobox references

sec-Butyl alcohol, 2-Butanol

1718764 (R)
1718763 (S)

396584 (R)
25655 (S)

2-Butanol, or sec-butanol, is an organic compound with formula CH₃CH(OH)CH₂CH₃. This secondary alcohol is a flammable, colorless liquid that is soluble in 3 parts water and completely miscible with polar organic solvents such as ethers and other alcohols. It is produced on a large scale, primarily as a precursor to the industrial solvent methyl ethyl ketone. 2-Butanol is chiral and thus can be obtained as either of two stereoisomers designated as (R)-(−)-2-butanol and (S)-(+)-2-butanol. It is normally found as an equal mixture of the two stereoisomers — a racemic mixture.

2-Butanol is manufactured industrially by the hydration of 1-butene or 2-butene:

Sulfuric acid is used as a catalyst for this conversion.

In the lab it can be prepared via Grignard reaction by reacting ethylmagnesium bromide with acetaldehyde in dried diethyl ether or tetrahydrofuran.

Although some 2-butanol is used as a solvent, it is mainly converted to butanone ("MEK"), which is an important industrial solvent and found in many domestic cleaning agents and paint removers. Volatile esters of 2-butanol have pleasant aromas and are used in small amounts as perfumes or in artificial flavors.