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827-52-1

Basic Information
CAS No.: 827-52-1
Name: Cyclohexylbenzene
Article Data: 514
Cas Database
Molecular Structure:
Molecular Structure of 827-52-1 (Cyclohexylbenzene)
Formula: C12H16
Molecular Weight: 160.259
Synonyms: 1,1'-Biphenyl, 1,2,3,4,5,6-hexahydro-;4-Cyclohexylbenzene;AI3-05776;BRN 1906803;Cyclohexane, phenyl-;Cyclohexylbenzene;NSC 40473;NSC 69101;
EINECS: 212-572-0
Density: 0.939 g/mL at 25 °C(lit.)
Melting Point: 5 °C
Boiling Point: 242.6 °C at 760 mmHg
Flash Point: 93.2 °C
Solubility: Insoluble in water
Appearance: Colourless liquid
Hazard Symbols: HarmfulXn,DangerousN
Risk Codes: 22-36/38-50/53
Safety: 26-60-61
Transport Information: UN 3082 9/PG 3
PSA: 0.00000
LogP: 3.73430
Synthetic route
771-98-2

1-Phenylcyclohexene

827-52-1

1-phenyl-1-cyclohexane

Conditions
ConditionsYield
With hydrogen; Pd-immobilized assembled capillaries In tetrahydrofuran at 20℃; for 0.283333h;100%
With hydrogen; micro-encapsulated PI palladium catalyst In tetrahydrofuran at 20℃; for 0.0833333h; Product distribution / selectivity;99%
Stage #1: 1-Phenylcyclohexene With lithium triethylborohydride; cobalt(II) bromide In tetrahydrofuran Inert atmosphere; Glovebox;
Stage #2: With hydrogen In tetrahydrofuran at 20℃; under 1500.15 Torr; for 3h;
99%
110-83-8

cyclohexene

71-43-2

benzene

827-52-1

1-phenyl-1-cyclohexane

Conditions
ConditionsYield
With Y type molecular seives containing SiO2/Al2O3 at 150℃; under 22502.3 Torr; Temperature;99%
With Y-type molecular sieve at 150℃; under 22502.3 Torr; Flow reactor;99.1%
With scandium tris(trifluoromethanesulfonate) In 1,2-dichloro-ethane at 20℃; for 24h; Friedel-Crafts alkylation;98%
108-85-0

1-bromocyclohexane

phenylmagnesium bromide

827-52-1

1-phenyl-1-cyclohexane

Conditions
ConditionsYield
With N,N,N,N,-tetramethylethylenediamine; iron(III) chloride In tetrahydrofuran at 0℃; for 0.5h;99%
Stage #1: phenylmagnesium bromide With dichloro(N,N,N’,N‘-tetramethylethylenediamine)zinc In tetrahydrofuran at 20℃; for 1h;
Stage #2: 1-bromocyclohexane With iron(III) chloride In tetrahydrofuran at 50℃; for 0.5h;
97%
With (1R,2R)-bis(dimethylamino)cyclohexane In tetrahydrofuran at 25℃; for 0.25h;95%
474317-61-8

4-cyclohexylphenyl trifluoromethanesulfonate

827-52-1

1-phenyl-1-cyclohexane

Conditions
ConditionsYield
With methanol; magnesium; palladium on activated charcoal at 20℃; for 24h;99%
With ammonium acetate; magnesium; palladium on activated charcoal In methanol at 20℃; for 1h;94%
108-85-0

1-bromocyclohexane

100-58-3

phenylmagnesium bromide

827-52-1

1-phenyl-1-cyclohexane

Conditions
ConditionsYield
With N,N,N,N,-tetramethylethylenediamine; iron(III) chloride In tetrahydrofuran at 0℃; Product distribution / selectivity;99%
With Fe4(μ-Ph)6(THF)4∘2THF In tetrahydrofuran at 20℃; for 0.166667h;95%
With bis(triphenylphosphoranediyl)ammonium tetrachloroferrate(III) at 20℃; for 1h; Reagent/catalyst; Schlenk technique; Inert atmosphere;94%
1165952-92-0

cyclohexa-1,4-diene

771-98-2

1-Phenylcyclohexene

A

827-52-1

1-phenyl-1-cyclohexane

B

110-83-8

cyclohexene

Conditions
ConditionsYield
With C24H72Ba2N4Si8 In (2)H8-toluene at 120℃; for 3h; Inert atmosphere; Schlenk technique; Sealed tube;A 99%
B n/a
626-62-0

1-iodocyclohexane

phenylmagnesium bromide

827-52-1

1-phenyl-1-cyclohexane

Conditions
ConditionsYield
Stage #1: phenylmagnesium bromide With dichloro(N,N,N’,N‘-tetramethylethylenediamine)zinc In tetrahydrofuran at 20℃; for 1h;
Stage #2: Cyclohexyl iodide With iron(III) chloride In tetrahydrofuran at 50℃; for 0.5h;
98%
With (1R,2R)-bis(dimethylamino)cyclohexane In tetrahydrofuran at 25℃; for 0.25h;95%
With N,N,N,N,-tetramethylethylenediamine; iron(III) chloride In tetrahydrofuran at 0℃; for 0.5h;99 % Chromat.
626-62-0

1-iodocyclohexane

1078-58-6

diphenylzinc

827-52-1

1-phenyl-1-cyclohexane

Conditions
ConditionsYield
With N,N,N,N,-tetramethylethylenediamine; iron(III) chloride In tetrahydrofuran at 50℃; for 0.5h; Product distribution / selectivity;98%
4894-75-1

1-phenyl-4-cyclohexanone

827-52-1

1-phenyl-1-cyclohexane

Conditions
ConditionsYield
With sodium cyanoborohydride at 20℃; for 0.05h;98%
With ethoxyethoxyethanol; hydrazine hydrate; potassium hydroxide at 220℃; under 10343.2 Torr; Wolff-Kishner Reduction; Sonication;83%
With polymethylhydrosiloxane; iron(III) chloride hexahydrate In 1,2-dichloro-ethane at 120℃; for 1h; Microwave irradiation;64%
92-52-4

biphenyl

827-52-1

1-phenyl-1-cyclohexane

Conditions
ConditionsYield
With Raney nickel; isopropyl alcohol at 82℃; for 6h; Temperature; Inert atmosphere;97%
With nickel(II) oxide; monoaluminum phosphate; iron(II) phthalocyanine; hydrogen at 180℃; under 18751.9 Torr; Large scale;96%
With Raney Ni-Al In potassium hydroxide; water at 90℃; for 3h; Reduction;95%
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Reported in EPA TSCA Inventory.

Specification

The Cyclohexylbenzene with CAS registry number of 827-52-1 is also known as Benzene,cyclohexyl-. The IUPAC name is Cyclohexylbenzene. It belongs to product categories of Biphenyl & Diphenyl Ether. Its EINECS registry number is 212-572-0. In addition, the formula is C12H16 and the molecular weight is 160.26. What's more, it is a colourless liquid and should be sealed in cool, dry place.

Physical properties about Cyclohexylbenzene are: (1)ACD/LogP: 4.74; (2)ACD/LogD (pH 5.5): 4.74; (3)ACD/LogD (pH 7.4): 4.74; (4)ACD/BCF (pH 5.5): 2348.77; (5)ACD/BCF (pH 7.4): 2348.77; (6)ACD/KOC (pH 5.5): 9004.16; (7)ACD/KOC (pH 7.4): 9004.16; (8)#Freely Rotating Bonds: 1; (9)Index of Refraction: 1.522; (10)Molar Refractivity: 52.11 cm3; (11)Molar Volume: 170.6 cm3; (12)Surface Tension: 34.5 dyne/cm; (13)Density: 0.939 g/cm3; (14)Flash Point: 93.2 °C; (15)Enthalpy of Vaporization: 46.01 kJ/mol; (16)Boiling Point: 242.6 °C at 760 mmHg; (17)Vapour Pressure: 0.0524 mmHg at 25 °C.

Preparation of Cyclohexylbenzene: Firstly, cyclohexene is added to benzene and sulfuric acid mixture under stirring at the temperature of 10-20 °C for 0.5-1 hour. Then the mixture is heated for another 1 hour. Secondly, reservoir is washed by water and lye, and then it is fractionated. At last, product is obtained by collecting distillate at 230-260 °C and distillate at the boiling point.

Uses of Cyclohexylbenzene: it is used to produce 1-cyclohexyl-4-nitro-benzene. The reaction occurs with reagents HNO3, HOAc at the temperature of -10 °C for 30 minutes. The yield is about 57%.

Cyclohexylbenzene is used to produce 1-cyclohexyl-4-nitro-benzene.

When you are using this chemical, please be cautious about it. As a chemical, it is irritating to eyes, skin and it is harmful if swallowed. What's more, it is very toxic to aquatic organisms that may cause long-term adverse effects in the aquatic environment. This material and its container must be disposed of as hazardous waste. During using it, avoid release to the environment. If contact with eyes accidently, rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
1. Canonical SMILES: C1CCC(CC1)C2=CC=CC=C2
2. InChI: InChI=1S/C12H16/c1-3-7-11(8-4-1)12-9-5-2-6-10-12/h1,3-4,7-8,12H,2,5-6,9-10H2
3. InChIKey: IGARGHRYKHJQSM-UHFFFAOYSA-N

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 248mg/kg (248mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

LUNGS, THORAX, OR RESPIRATION: DYSPNEA

SKIN AND APPENDAGES (SKIN): HAIR: OTHER
Life Sciences. Vol. 31, Pg. 803, 1982.
mouse LD50 intravenous 67mg/kg (67mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

SKIN AND APPENDAGES (SKIN): HAIR: OTHER

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Life Sciences. Vol. 31, Pg. 803, 1982.
rabbit LD50 skin > 7940mg/kg (7940mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: FOOD INTAKE (ANIMAL)
National Technical Information Service. Vol. OTS0545758,
rat LDLo oral 5gm/kg (5000mg/kg)   "Toxicology and Biochemistry of Aromatic Hydrocarbons," Gerarde, H., New York, Elsevier, 1960Vol. -, Pg. 55, 1960.