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827-52-1

Basic Information
CAS No.: 827-52-1
Name: Cyclohexylbenzene
Molecular Structure:
Molecular Structure of 827-52-1 (Cyclohexylbenzene)
Formula: C12H16
Molecular Weight: 160.26
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%
108-85-0

1-bromocyclohexane

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;97%
In benzene-d6 at 20℃; for 2h; Inert atmosphere; Glovebox;
With bis(triphenylphosphoranediyl)ammonium tetrachloroferrate(III) In tetrahydrofuran at 20℃; for 24h; Schlenk technique; Inert atmosphere;
56056-49-6

(n-dodecylthio)benzene

931-50-0

cyclohexylmagnesium bromide

827-52-1

1-phenyl-1-cyclohexane

Conditions
ConditionsYield
With Nickel (II) acetylacetonate; (Z)-3,3-dimethyl-1,2-bis(diphenylphosphino)-1-butene In cyclopentyl methyl ether for 5h; Inert atmosphere; Reflux;97%
80-30-8

N-cyclohexyl-p-toluenesulfonamide

71-43-2

benzene

827-52-1

1-phenyl-1-cyclohexane

Conditions
ConditionsYield
With sulfuric acid for 3.5h; Heating;96%
100-68-5

methyl-phenyl-thioether

931-50-0

cyclohexylmagnesium bromide

827-52-1

1-phenyl-1-cyclohexane

Conditions
ConditionsYield
With Nickel (II) acetylacetonate; (Z)-3,3-dimethyl-1,2-bis(diphenylphosphino)-1-butene In cyclopentyl methyl ether for 5h; Inert atmosphere; Reflux;95%
34883-41-5

3,5-dichlorobiphenyl

827-52-1

1-phenyl-1-cyclohexane

Conditions
ConditionsYield
With potassium hydroxide; Raney Ni-Al alloy In water at 90℃; for 3h;95%
2051-60-7

2-chloro-1,1'-biphenyl

827-52-1

1-phenyl-1-cyclohexane

Conditions
ConditionsYield
With potassium hydroxide In water at 90℃; for 2h;94%
With potassium hydroxide; Raney Ni-Al alloy In water at 90℃; for 4h;91%
626-62-0

1-iodocyclohexane

368-47-8

phenyltrifluorosilane

827-52-1

1-phenyl-1-cyclohexane

Conditions
ConditionsYield
With (1,2-dimethoxyethane)dichloronickel(II); (1S,2R)-(+)-norphedrine; lithium hexamethyldisilazane; water; cesium fluoride In N,N-dimethyl acetamide at 60℃; for 16h; Hiyama cross-coupling;94%
108-85-0

1-bromocyclohexane

phenylmagnesium bromide

A

92-52-4

biphenyl

B

827-52-1

1-phenyl-1-cyclohexane

Conditions
ConditionsYield
Stage #1: 1-bromocyclohexane; [Fe(C2H4)4][Li(tmeda)]2 In tetrahydrofuran at -20℃;
Stage #2: phenylmagnesium bromide In tetrahydrofuran; diethyl ether at -20℃; Further stages.;
A n/a
B 94%
2050-67-1

PCB 11

827-52-1

1-phenyl-1-cyclohexane

Conditions
ConditionsYield
With potassium hydroxide; Raney Ni-Al alloy In water at 90℃; for 3h;94%
2050-68-2

4,4'-dichlorobiphenyl

827-52-1

1-phenyl-1-cyclohexane

Conditions
ConditionsYield
With Raney Ni-Al alloy; potassium carbonate In water at 90℃; for 5h;93%
34883-39-1

2,5-dichlorobiphenyl

827-52-1

1-phenyl-1-cyclohexane

Conditions
ConditionsYield
With potassium hydroxide; Raney Ni-Al alloy In water at 90℃; for 3h;93%
16156-56-2

cyclohexyl mesylate

71-43-2

benzene

827-52-1

1-phenyl-1-cyclohexane

Conditions
ConditionsYield
With scandium tris(trifluoromethanesulfonate) at 80℃; for 4h;92%
scandium tris(trifluoromethanesulfonate) at 80℃; for 4h;92%
108-85-0

1-bromocyclohexane

591-51-5

phenyllithium

827-52-1

1-phenyl-1-cyclohexane

Conditions
ConditionsYield
[Li(tmeda)]2[Fe(C2H4)4] In tetrahydrofuran at -20℃;92%
With N,N,N,N,-tetramethylethylenediamine; iron(II) chloride In tetrahydrofuran; dibutyl ether at 20℃; for 1h;
827-52-1

1-phenyl-1-cyclohexane

Conditions
ConditionsYield
With Raney Ni-Al alloy; potassium carbonate In water at 90℃; for 3h;92%
2051-62-9

4'-biphenyl chloride

827-52-1

1-phenyl-1-cyclohexane

Conditions
ConditionsYield
With cesium hydroxide In water at 90℃; for 4h;91%
With cesium hydroxide; Raney Ni-Al alloy In water at 90℃; for 4h;91%
108-90-7

chlorobenzene

931-50-0

cyclohexylmagnesium bromide

827-52-1

1-phenyl-1-cyclohexane

Conditions
ConditionsYield
Stage #1: cyclohexylmagnesium bromide With 1,3-bis[(2,6-diisopropyl)phenyl]imidazolinium chloride In tetrahydrofuran at 20℃; for 0.166667h; Kumada Cross-Coupling; Flow reactor; Inert atmosphere;
Stage #2: chlorobenzene With iron(III)-acetylacetonate In tetrahydrofuran at 25℃; for 0.0833333h; Kumada Cross-Coupling; Inert atmosphere; Flow reactor; Irradiation;
91%
92-52-4

biphenyl

A

92-51-3

cyclohexylcyclohexane

B

827-52-1

1-phenyl-1-cyclohexane

Conditions
ConditionsYield
With MmNi3.5Co0.7Al0.8H4 at 160℃; under 3677.5 Torr; for 3h;A 4%
B 90%
With MmNi3.5Co0.7Al0.8H4 at 160℃; under 3677.5 Torr; for 3h; Product distribution; other biphenyls, var. temp., var. conc.;A 89%
B 7%
With hydrogen; [(norbornadiene)rhodium(I)chloride]2; phosphinated polydiacetylene In n-heptane at 30℃; under 60800 Torr; for 5.7h;A 78%
B 21%
2051-61-8

m-chlorobiphenyl

827-52-1

1-phenyl-1-cyclohexane

Conditions
ConditionsYield
With potassium hydroxide In water at 90℃; for 2h;90%
With Raney Ni-Al alloy; potassium carbonate In water at 90℃; for 5h;90%
2974-92-7

3,4-dichlorobiphenyl

827-52-1

1-phenyl-1-cyclohexane

Conditions
ConditionsYield
With potassium hydroxide; Raney Ni-Al alloy In water at 90℃; for 3h;90%
132-65-0

dibenzothiophene

A

92-52-4

biphenyl

B

827-52-1

1-phenyl-1-cyclohexane

Conditions
ConditionsYield
With hydrogen In n-heptane at 350℃; under 760.051 Torr; for 1h; Catalytic behavior; Reagent/catalyst; Temperature; Flow reactor;A 88.6%
B 4%
With hydrogen sulfide; hydrogen In Hexadecane at 300℃; under 54755.5 Torr; for 8h; Catalytic behavior; Reagent/catalyst; Inert atmosphere;A 80.6%
B 15.2%
With aluminum oxide; sodium hydroxide; hydrogen; dodecacarbonyl-triangulo-triruthenium In xylene at 300℃; under 38000 Torr; for 10h; Product distribution; on alumina-supported ruthenium acetylacetonate or ruthenium chloride catalyst systems;A 67%
B 4%
827-52-1

1-phenyl-1-cyclohexane

75-36-5

acetyl chloride

18594-05-3

4-cyclohexylacetophenone

Conditions
ConditionsYield
With aluminum (III) chloride In dichloromethane at 0℃; for 0.166667h;100%
With aluminium trichloride In dichloromethane for 24h; Ambient temperature;85%
With aluminium trichloride In dichloromethane at 0℃; for 0.5h;61%
827-52-1

1-phenyl-1-cyclohexane

92-51-3

cyclohexylcyclohexane

Conditions
ConditionsYield
With hydrogen; platinum(IV) oxide In acetic acid at 250℃; under 1875.2 Torr; for 8h;100%
With hydrogen; [(η6-C6H6)(η6-C6Me6)Ru3(μ2-H)(μ2-OH)(μ3-O)]+ In water at 110℃; under 45003.6 Torr; for 1h;100.0 % Chromat.
201230-82-2

carbon monoxide

827-52-1

1-phenyl-1-cyclohexane

27634-89-5

4-cyclohexylbenzaldehyde

Conditions
ConditionsYield
With hydrogen fluoride; boron trifluoride In n-heptane at -30℃; under 15001.5 Torr; for 1h; Autoclave;100%
With hydrogen fluoride; boron trifluoride In n-heptane at -30℃; under 15001.5 Torr; for 1h;
With hydrogen fluoride; boron trifluoride In n-heptane at -30℃; under 15001.5 Torr; for 1h; Autoclave;
With hydrogen fluoride; boron trifluoride In n-heptane at -30℃; under 15001.5 Torr; for 1h; Autoclave;
With hydrogen fluoride; boron trifluoride In n-heptane at -30℃; under 15001.5 Torr; for 1h; Autoclave;
827-52-1

1-phenyl-1-cyclohexane

106241-39-8

α-chloromethylthio-γ-butyrolactone

106241-50-3

3-(4-Cyclohexyl-benzylsulfanyl)-dihydro-furan-2-one

Conditions
ConditionsYield
With tin(IV) chloride In dichloromethane for 1h; Ambient temperature;94%
827-52-1

1-phenyl-1-cyclohexane

98-89-5

Cyclohexanecarboxylic acid

Conditions
ConditionsYield
With sodium periodate; ruthenium trichloride In tetrachloromethane; water; acetonitrile for 24h; Ambient temperature;94%
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    Product name Cyclohexylbenzene Synonyms CYCLOHEXYLBENZENE;CYCLOHEXYLBENZENE, 97+%;Benzene, cyclohexyl-;CYCLOHEXYBENZENE (CHB);Cyclohexylbenzol;Cyclohexylbenzoyl;2-Phenylcyclohexane;Cyclohexylbenzene,

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  • Cyclohexylbenzene CAS 827-52-1

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Consensus Reports

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.