4-tert-Butylcyclohexanone Property

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

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

Cyclohexanone, 4-(1,1-dimethylethyl)- (98-53-3)

Safety

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

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 and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H412Harmful to aquatic life with long lasting effects

Precautionary statements

P273Avoid release to the environment.

4-tert-Butylcyclohexanone Chemical Properties,Usage,Production

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.]