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Perillartine 30950-27-7 Perillartine
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4-tert-Butylcyclohexanone Basic information |
Product Name: | 4-tert-Butylcyclohexanone |
Synonyms: | 98-53-3;4-tert-Butylcyclohexanone, 99% 100GR;4-TERT-BUTYLCYCLOHEXANONE;P-TERT-BUTYLCYCLOHEXANONE;PARA TERTIARY BUTYL CYCLOHEXANONE;TIMTEC-BB SBB007656;4CO;AKOS BBS-00000687 |
CAS: | 98-53-3 |
MF: | C10H18O |
MW: | 154.25 |
EINECS: | 202-678-5 |
Product Categories: | Halogenated Heterocycles ,Pyrimidines;Carbonyl Compounds;Liquid Crystal intermediates;C10;Ketones |
Mol File: | 98-53-3.mol |
4-tert-Butylcyclohexanone Chemical Properties |
Melting point | 47-50 °C (lit.) |
Boiling point | 113-116 °C/20 mmHg (lit.) |
density | 0.893 |
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 |
Water Solubility | Soluble in alcohol, ethanol (0.5g/10 mL). Insoluble in water. |
BRN | 507309 |
InChIKey | YKFKEYKJGVSEIX-UHFFFAOYSA-N |
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 |
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 |
MSDS Information |
Provider | Language |
---|---|
SigmaAldrich | English |
ACROS | English |
ALFA | English |
4-tert-Butylcyclohexanone Usage And Synthesis |
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. |
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.] |
4-tert-Butylcyclohexanone Preparation Products And Raw materials |
Perillartine Basic information |
Product Name: | Perillartine |
Synonyms: | 1-PERILLALDEHYDE A-ANTIOXIME;1-Cyclohexene-1-carboxaldehyde, 4-(1-methylethenyl)-, oxime, (E)-;1-Cyclohexene-1-carboxaldehyde, 4-isopropenyl-, anti-oxime;1-Perillaldehyde alpha-antioxime;1-perillaldehydealpha-antioxime;4-(1-methylethenyl)-,oxime,(e)-1-cyclohexene-1-carboxaldehyd;4-(1-Methylethenyl)-1-cyclohexene-1-carbaldehyde (E)-oxime;4-Isopropenyl-1-cyclohexene-1-carbaldehyde (E)-oxime |
CAS: | 30950-27-7 |
MF: | C10H15NO |
MW: | 165.23 |
EINECS: | 250-402-7 |
Product Categories: | food additives |
Mol File: | 30950-27-7.mol |
Perillartine Chemical Properties |
Melting point | 102°C |
Boiling point | 293.09°C (rough estimate) |
density | 1.0203 (rough estimate) |
refractive index | 1.5200 (estimate) |
storage temp. | under inert gas (nitrogen or Argon) at 2–8 °C |
pka | 11.45±0.28(Predicted) |
color | Very sweet crystals |
NIST Chemistry Reference | Perillartine(30950-27-7) |
EPA Substance Registry System | 1-Cyclohexene-1-carboxaldehyde, 4-(1-methylethenyl)-, oxime, (E)- (30950-27-7) |
Safety Information |
Risk Statements | 36/37/38 |
Safety Statements | 26-36/37/39 |
Toxicity | LD50 orl-rat: 2500 mg/kg AFDOAQ 15,82,51 |
MSDS Information |
Perillartine Usage And Synthesis |
Safety Profile | Moderately toxic by ingestion. When heated to decomposition it emits toxic fumes of NOx. |
Perillartine Preparation Products And Raw materials |
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