4-tert-Butylcyclohexanone
- CAS NO.:98-53-3
- Empirical Formula: C10H18O
- Molecular Weight: 154.25
- MDL number: MFCD00001642
- EINECS: 202-678-5
- SAFETY DATA SHEET (SDS)
- Update Date: 2024-08-22 14:21:17
What is 4-tert-Butylcyclohexanone?
Chemical properties
WHITE TO ALMOST WHITE CRYSTALLINE POWDER
Occurrence
Has apparently not been reported to occur in nature.
The Uses of 4-tert-Butylcyclohexanone
4-tert-Butylcyclohexanone is used as a perfuming agents and in cosmetic.
Preparation
By hydrogenation of p-ferr-butylphenol. Care must be taken that no free p-tert-butylphenol remains, because it is a sensitizer and depigmenting agent(Opdyke, 1974).
Preparation
N-Chlorosuccinimide (NCS) (8.0 g, 0.060 mol) and toluene (200 mL) were cooled to 0 C° in a 1-L, threenecked, round-bottomed flask equipped with a mechanical stirrer, a thermometer, a dropping funnel, and an argon inlet tube. Dimethyl sulfoxide (6.0 mL, 0.10 mol) was added and the mixture was cooled to -25 C° using a tetrachloromethane/dryice bath. A solution of 4-tert-butylcyclohexanol (6.24 g, 0.04 mol; mixture of E and Z isomers) in toluene (40 mL) was added dropwise over 5 min, stirring was continued for 2 h at -25 C°, and then a solution of triethylamine (6.0 g, 0.06 mol) in toluene (10 mL) was added dropwise over 3 min. The cooling bath was removed, and, after 5 min, diethyl ether (400 mL) was added. The organic phase was washed with 1% aq. hydrochloric acid (100 mL) and then with water (2 × 100 mL), and dried over anhydrous magnesium sulfate. The solvents were evaporated under reduced pressure, and the residue was transferred to a 50-mL, round-bottomed flask and bulb-to-bulb distilled at 120 C° (25 mmHg) to yield 5.72 g (93%) of 4-tertbutylcyclohexanone 1794; mp 41–45 C°. Recrystallization from petroleum ether at -20 C° gave an 88% recovery of 1794 with mp 45–46 C°.
Definition
ChEBI: Cyclohexanone, 4-(1,1-dimethylethyl)- is a cyclic ketone.
Synthesis Reference(s)
Chemistry Letters, 24, p. 507, 1995
Journal of the American Chemical Society, 94, p. 7586, 1972 DOI: 10.1021/ja00776a056
Tetrahedron Letters, 16, p. 3775, 1975
Purification Methods
Purify it via the semicarbazone (crystallised from EtOH with m 203-205o), hydrolyse this with dilute HCl and steam distil it. The distillate is extracted into Et2O, dried, evaporated and the residue is recrystallised from pentane, aqueous EtOH or EtOH [Houlihan J Org Chem 27 3860 1962]. The oxime recrystallises from 1,2-dichloropropane and has m 137.5-138.5o. [Harvill et al. J Org Chem 15 58 1950, Beilstein 7 IV 82.]
Properties of 4-tert-Butylcyclohexanone
Melting point: | 47-50 °C (lit.) |
Boiling point: | 113-116 °C/20 mmHg (lit.) |
Density | 0.893 |
vapor pressure | 7.91-14.2Pa at 20-25℃ |
refractive index | 1.4570 (estimate) |
Flash point: | 205 °F |
storage temp. | Sealed in dry,Room Temperature |
solubility | Chloroform (Slightly), Methanol (Slightly) |
form | Crystalline Powder |
color | White to almost white |
Odor | Powerful, dry-camphoraceous, slightly minty odor with woody Cedar-Patchouli-like undertones. |
Water Solubility | Soluble in alcohol, ethanol (0.5g/10 mL). Insoluble in water. |
BRN | 507309 |
CAS DataBase Reference | 98-53-3(CAS DataBase Reference) |
NIST Chemistry Reference | Cyclohexanone, 4-(1,1-dimethylethyl)-(98-53-3) |
EPA Substance Registry System | Cyclohexanone, 4-(1,1-dimethylethyl)- (98-53-3) |
Safety information for 4-tert-Butylcyclohexanone
Signal word | Warning |
Pictogram(s) |
Exclamation Mark Irritant GHS07 |
GHS Hazard Statements |
H302:Acute toxicity,oral H412:Hazardous to the aquatic environment, long-term hazard |
Precautionary Statement Codes |
P273:Avoid release to the environment. |
Computed Descriptors for 4-tert-Butylcyclohexanone
InChIKey | YKFKEYKJGVSEIX-UHFFFAOYSA-N |
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