| Identification | More | [Name]
4-tert-Butylcyclohexanone | [CAS]
98-53-3 | [Synonyms]
4-TERT-BUTYLCYCLOHEXANONE
AKOS BBS-00000687
CYCLOHEXANONE, 4-(1,1-DIMETHYL ETHYL)
PARA TERTIARY BUTYL CYCLOHEXANONE
P-TERT-BUTYLCYCLOHEXANONE
TIMTEC-BB SBB007656
4-(1,1-dimethylethyl)-cyclohexanon
4-(1,1-dimethylethyl)-Cyclohexanone
4-butylcyclohexanone
4-t-Butylcyclohexanone
c 64
c64
Cyclohexanone, 4-tert-butyl-
Cyclohexanone, p-tert-butyl-
gamma-tert-Butylcyclohexanone
p-tert-butyl-cyclohexanon
4-Tert-Butylcyclohexanone,~92%
4-tert-Butylcyclohexanone,99%
4-tert-Butyl
4-tert-butyl-cyclohe | [EINECS(EC#)]
202-678-5 | [Molecular Formula]
C10H18O | [MDL Number]
MFCD00001642 | [Molecular Weight]
154.25 | [MOL File]
98-53-3.mol |
| Chemical Properties | Back Directory | [Appearance]
WHITE TO ALMOST WHITE CRYSTALLINE POWDER | [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) | [Fp ]
205 °F
| [storage temp. ]
Sealed in dry,Room Temperature | [solubility ]
Chloroform (Slightly), Methanol (Slightly) | [form ]
Crystalline Powder | [color ]
White to almost white | [Odor]
at 1.00 % in dipropylene glycol. woody mint patchouli musk leather | [Odor Type]
woody | [Water Solubility ]
Soluble in alcohol, ethanol (0.5g/10 mL). Insoluble in water. | [BRN ]
507309 | [InChIKey]
YKFKEYKJGVSEIX-UHFFFAOYSA-N | [LogP]
2.91 | [CAS DataBase Reference]
98-53-3(CAS DataBase Reference) | [NIST Chemistry Reference]
Cyclohexanone, 4-(1,1-dimethylethyl)-(98-53-3) | [EPA Substance Registry System]
98-53-3(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing . | [WGK Germany ]
2
| [RTECS ]
GW1140000
| [TSCA ]
Yes | [HS Code ]
29142990 | [Toxicity]
Both the acute oral LD50 value in rats and the acute dermal LD50 value in rabbits were reported to be 5 g/kg |
| Hazard Information | Back Directory | [Chemical Properties]
WHITE TO ALMOST WHITE CRYSTALLINE POWDER | [Occurrence]
Has apparently not been reported to occur in nature. | [Uses]
4-tert-Butylcyclohexanone is used as a perfuming agents and in cosmetic. | [Definition]
ChEBI: Cyclohexanone, 4-(1,1-dimethylethyl)- is a cyclic ketone. | [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°. | [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.] |
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