3-Heptanone

3-Heptanone

Names
IUPAC name Heptan-3-one
Other names Ethyl-butyl Ketone; 3-oxoheptane; Butyl ethyl ketone
Identifiers
CAS Number	106-35-4 Y
3D model (Jmol)	Interactive image
Beilstein Reference	506161
ChEBI	CHEBI:50139
ChemSpider	7514 Y
ECHA InfoCard	100.003.081
EC Number	203-388-1
MeSH	3-Heptanone
PubChem	24901132
RTECS number	MJ5250000
UN number	1224
SMILES CCC(=O)CCCC
Properties
Chemical formula	C7H14O
Molar mass	114.19 g·mol−1
Appearance	Colorless liquid
Odor	powerful, fruity[1]
Density	0.812 g cm−3
Melting point	−39 °C (−38 °F; 234 K)
Boiling point	146 to 149 °C (295 to 300 °F; 419 to 422 K)
Solubility in water	1% (20 °C)[1]
Vapor pressure	4 mmHg (20 °C)[1]
Hazards
Safety data sheet	[2]
R-phrases	R10, R22
S-phrases	S23
Flash point	41 °C (106 °F; 314 K)
Lethal dose or concentration (LD, LC):
LD50 (median dose)	2760 mg/kg (rat, oral)[3]
US health exposure limits (NIOSH):
PEL (Permissible)	TWA 50 ppm (230 mg/m3)[1]
REL (Recommended)	TWA 50 ppm (230 mg/m3)[1]
IDLH (Immediate danger)	1000 ppm[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

3-Heptanone (butyl ethyl ketone), is a seven carbon ketone. It is a colorless liquid with a "green odor," also described to have a fruity scent. It is often used as a perfume/fragrance, as a solvent for cellulose, nitrocellulose, or vinyl resins, and as a synthetic building block in the preparation of other organic molecules.^[4]

Preparation

3-Heptanone is produced industrially through reductive condensation of propanal with 2-butanone. This reaction does not immediately yield 3-Heptanone. Rather it results in the production of a ketone with an alkene group. This alkene can be removed with hydrogenation.

CH3CH2CHO + CH3C(O)CH2CH3 --> CH3CH2C(O)CH=CHCH2CH3 + H2 --> CH3CH2C(O)CH2CH2CH2CH3

References