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2-Butanol

2-Butanol
Skeletal formula of 2-butanol
Names
IUPAC name
Butan-2-ol
Other names
sec-Butanol

sec-Butyl alcohol, 2-Butanol

2-Butyl alcohol
Identifiers
78-92-2 YesY
14898-79-4 (R) YesY
4221-99-2 (S) YesY
3D model (Jmol) Interactive image
773649

1718764 (R)
1718763 (S)
ChEBI CHEBI:35687 YesY
ChEMBL ChEMBL45462 YesY
ChemSpider 6320 YesY
76392 (R) YesY
392543 (S) YesY
DrugBank DB02606 YesY
ECHA InfoCard 100.001.053
EC Number 201-158-5
1686

396584 (R)
25655 (S)
MeSH 2-butanol
PubChem 6568
84682 (R)
444683 (S)
RTECS number EO1750000
UN number 1120
Properties
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
290 g/L
log P 0.683
Vapor pressure 1.67 kPa (at 20 °C)
-57.683·10−6 cm3/mol
1.3978 (at 20 °C)
Thermochemistry
197.1 J K−1 mol−1
213.1 J K−1 mol−1
−343.3–−342.1 kJ mol−1
−2.6611–−2.6601 MJ mol−1
Hazards
Safety data sheet inchem.org
GHS pictograms The flame pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS) The exclamation-mark pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS)
GHS signal word WARNING
H226, H319, H335, H336
P261, P305+351+338
Irritant Xi
R-phrases R10, R36/37, R67
S-phrases (S2), S7/9, S13, S24/25, S26, S46
NFPA 704
Flammability code 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g., gasoline) Health code 1: Exposure would cause irritation but only minor residual injury. E.g., turpentine Reactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogen Special hazards (white): no codeNFPA 704 four-colored diamond
Flash point 22 to 27 °C (72 to 81 °F; 295 to 300 K)
405 °C (761 °F; 678 K)
Explosive limits 1.7–9.8%
Lethal dose or concentration (LD, LC):
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).
YesY  (what is YesYN ?)
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.


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