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110-82-7

Basic Information
CAS No.: 110-82-7
Name: Cyclohexane
Article Data: 1087
Cas Database
Molecular Structure:
Molecular Structure of 110-82-7 (Cyclohexane)
Formula: C6H12
Molecular Weight: 84.1613
Synonyms: Cyclohexan [German];RCRA waste no. U056;Cyclohexaan [Dutch];Cicloesano [Italian];Cyclohexane [UN1145] [Flammable liquid];hexahydro-;hexahydrobenzene;RCRA waste number U056;Cyclohexaan;Benzene, hexahydro-;Cyclohexan;Cykloheksan;hexanaphthene;hexamethylene;Cyclohexane (DOT;Cyclohexane ring;EPA Pesticide Chemical Code 025901;Cicloesano;10-81-1;Benzenehexahydride;Cykloheksan [Polish];Cyclobexane;Cyclohexane, Reagent;Cyclohexane, Spectrophotometric Grade;
EINECS: 203-806-2
Density: 0.791 g/cm3
Melting Point: 4-7 °C(lit.)
Boiling Point: 80.719 °C at 760 mmHg
Flash Point: -18ºC
Solubility: PRACTICALLY INSOLUBLE
Appearance: colorless liquid
Hazard Symbols: FlammableF,HarmfulXn,DangerousN
Risk Codes: 11-38-50/53-65-67
Safety: 9-16-25-33-60-61-62
Transport Information: N/A
PSA: 0.00000
LogP: 2.34060
Synthetic route
1165952-91-9

cyclohexa-1,3-diene

110-82-7

cyclohexane

Conditions
ConditionsYield
With Pd/C; hydrogen In chloroform at 20℃; under 760.051 Torr; for 2h; Catalytic behavior;100%
With hydrogen; HRh(CO)3 at 79.9℃; under 3750.3 Torr; for 1.66667h;63%
With hydrogen In tetrahydrofuran at 20℃; under 760.051 Torr; for 10h;50%
110-83-8

cyclohexene

110-82-7

cyclohexane

Conditions
ConditionsYield
With hydrogen; mer-Os(PPh3)3HBr(CO) at 150℃; under 3800 Torr; for 1h; Product distribution;100%
With hydrogen; decacarbonyldirhenium(0) at 230℃; under 37503 Torr; for 0.25h;100%
With {(η6-C6H6)Ru(NCCH3)3}{BF4}2; water; hydrogen In benzene at 90℃; under 30400 Torr; for 4h;100%
71-43-2

benzene

110-82-7

cyclohexane

Conditions
ConditionsYield
With hydrogen; [(norbornadiene)rhodium(I)chloride]2; polydiacetylene In n-heptane at 30℃; under 60800 Torr; for 0.9h; Product distribution; various aromatic compounds and other catalyst also investigated;100%
With hydrogen; Ni-Tc on γ-Al2O3 at 175 - 250℃; under 760 Torr; Product distribution; dependence of catalytic activity on the reduction temperature; enhanced activity of bimetallic catalysts;100%
With hydrogen; decacarbonyldirhenium(0) at 230℃; under 75005.9 Torr; for 0.25h;100%
108-85-0

1-bromocyclohexane

110-82-7

cyclohexane

Conditions
ConditionsYield
With 9-borabicyclo[3.3.1]nonane dimer; triphenylstannane In toluene at 0℃;100%
With triethylsilane; aluminium trichloride In dichloromethane at 18 - 20℃; for 0.25h;95%
With water; sodium iodide; nickel dichloride; zinc; sonication In N,N,N,N,N,N-hexamethylphosphoric triamide at 60℃; for 1h; Product distribution;82%
108-90-7

chlorobenzene

110-82-7

cyclohexane

Conditions
ConditionsYield
With hydrogen; Leuna-Kontakt 6525 at 150℃; Product distribution; other halogen organic compounds, var. catalysts;100%
With hydrogen; platinum at 120℃; under 16501.7 Torr; for 1.66667h; Autoclave; Inert atmosphere;12.8%
With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; hydrogen; triethylamine In isopropyl alcohol at 75℃; under 31028.9 Torr; for 4h; other chloroaromatics; var. reaction time; catalytic hydrodechlorination;
1333-74-0

hydrogen

110-83-8

cyclohexene

110-82-7

cyclohexane

Conditions
ConditionsYield
With C53H82ClN3P2Ru In dichloromethane-d2 at 50℃; under 3040.2 Torr; for 3h; Reagent/catalyst; Time;100%
at 25℃; Catalytic behavior;
With ReH(NO)2(P(CH(CH3)2)3)2; Dimethylphenylsilane; tris(pentafluorophenyl)borate at 100℃; under 30003 Torr; for 1h; Catalytic behavior; Autoclave;
With [ReH(NO)2(P(C6H11)3)2]; Dimethylphenylsilane; tris(pentafluorophenyl)borate at 100℃; under 30003 Torr; for 1h; Catalytic behavior; Autoclave;
at 80℃; under 30003 Torr; for 24h;
101-84-8

diphenylether

A

110-82-7

cyclohexane

B

108-93-0

cyclohexanol

C

71-43-2

benzene

Conditions
ConditionsYield
With isopropyl alcohol at 150℃; under 7500.75 Torr; for 12h; Inert atmosphere; Autoclave;A 25.1%
B 100%
C 74.9%
With isopropyl alcohol at 160℃; for 15h; Autoclave; Inert atmosphere;
With isopropyl alcohol at 150℃; for 10h; Catalytic behavior; Reagent/catalyst; Temperature; Sealed tube;A 24.6 %Chromat.
B 47.8 %Chromat.
C 24.3 %Chromat.
With isopropyl alcohol at 150℃; for 6h; Temperature; Sealed tube;A 15.2 %Chromat.
B 17.7 %Chromat.
C 5.8 %Chromat.
120-80-9

benzene-1,2-diol

110-82-7

cyclohexane

Conditions
ConditionsYield
With hydrogen In dodecane at 200℃; under 15001.5 Torr; for 8h;99.9%
bei der katalytischen Hyrierung;
With phosphoric acid; 5% Pd(II)/C(eggshell); hydrogen In water at 249.84℃; under 37503.8 Torr; for 0.5h; Autoclave;87 %Chromat.
1965-09-9

4,4'-dihydroxydiphenyl ether

110-82-7

cyclohexane

Conditions
ConditionsYield
With hydrogen In dodecane at 200℃; under 15001.5 Torr; for 2h;99.9%
With rhodium contaminated with carbon; N-methyldiethanolamine trifluoromethanesulfonate; hydrogen at 120℃; under 30003 Torr; for 6h; Autoclave;91.5%
With carbon nanotubes-supported ruthenium; hydrogen In dodecane; water at 220℃; under 37503.8 Torr; for 3h; Autoclave;64 %Chromat.
With hydrogen at 130℃; under 15001.5 Torr; for 6h; Ionic liquid; Autoclave; Schlenk technique;99.4 %Chromat.
91-10-1

1,3-dimethoxy-2-hydroxy-benzene

110-82-7

cyclohexane

Conditions
ConditionsYield
With hydrogen In dodecane at 200℃; under 15001.5 Torr; for 12h;99.9%
Multi-step reaction with 2 steps
1: hydrogen / water / 8 h / 200 °C / 30003 Torr / Autoclave
2: hydrogen / water / 4 h / 200 °C / 30003 Torr
View Scheme
With palladium on activated charcoal; hydrogen In water at 150℃; under 30003 Torr; for 4h; Reagent/catalyst; Autoclave;
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History

Unlike compounds like benzene, Cyclohexane (CAS NO.110-82-7) cannot easily be obtained from natural resources such as coal. Towards the end of the nineteenth century early chemical investigators had to depend on organic synthesis. It took them 30 years to flesh out the details.
In 1867 Marcellin Berthelot reduced benzene with hydroiodic acid at elevated temperatures. He incorrectly identified the reaction product as n-hexane not only because of the convenient match in boiling point (69°C) but also because he did not believe benzene was a cyclic molecule but rather some sort of association of acetylene.
In 1870 one of his sceptics Adolf von Baeyer repeated the reaction and pronounced the same reaction product hexahydrobenzene and in 1890 Vladimir Markovnikov believed he was able to distill the same compound from Caucasus petroleum calling his concoction hexanaphtene.
In 1894 Baeyer synthesized Cyclohexane (CAS NO.110-82-7) starting with a Dieckmann condensation of pimelic acid, and in the same year E. Haworth and W.H. Perkin Jr. (1860 - 1929) did the same in a Wurtz reaction of 1,6-dibromohexane.
Surprisingly their cyclohexanes(110-82-7) boiled higher by 10°C than either hexahydrobenzene or hexanaphtene but this riddle was solved in 1895 by Markovnikov, N.M. Kishner and Nikolay Zelinsky when they re-diagnosed hexahydrobenzene and hexanaphtene as methylcyclopentane, the result of an unexpected rearrangement reaction.

Consensus Reports

Community Right-To-Know List.

Standards and Recommendations

OSHA PEL: TWA 300 ppm
ACGIH TLV: TWA 100 ppm
DFG MAK: 200 ppm (720 mg/m3)
DOT Classification:  3; Label: Flammable Liquid

Analytical Methods

For occupational chemical analysis use NIOSH: Hydrocarbons.

Specification

The Cyclohexane is an organic compound with the formula C6H12. The IUPAC name of this chemical is cyclohexane. With the CAS registry number 110-82-7, the product's categories are Analytical Chemistry; Solvents for HPLC & Spectrophotometry; Solvents for Spectrophotometry; HPLC Solvents; Aluminum Bottles; Solvent Bottles; Solvents; Alpha Sort; C; CAlphabetic; CO - CZ; Volatiles/Semivolatiles; CO - CZChemical Class; Chemical Class; Hydrocarbons; NeatsAnalytical Standards ;C-D, Puriss p.a. ACS; Analytical Reagents for General Use; Puriss p.a. ACS; Amber Glass Bottles; Spectrophotometric Grade Solvents; Spectrophotometric GradeSolvents; Anhydrous Grade SolventsSolvents; AnhydrousSolvents; Returnable Container Solvents; Carbon Steel Cans with NPT Threads; ReagentPlus(R) Solvent Grade Products; ReagentPlus(R)Semi-Bulk Solvents; ReagentPlus(R)Solvents; Pesticide Residue Analysis (PRA) Solvents Solvent Bottles; PRA; ACS Grade Solvents; ACS GradeSemi-Bulk Solvents; ACS GradeSolvents; Chromatography/CE Reagents; Pestanal/Residue Analysis; Solvents - GC/SH; LC-MS Plus and Gradient; Spectroscopy; UV/Vis Solvents; UV/Visible (UV/VIS) Spectroscopy. Besides, it is colorless liquid, which should be stored in in a cool and well-ventilated place.

Physical properties about Cyclohexane are: (1)ACD/LogP: 3.16; (2)ACD/LogD (pH 5.5): 3.163; (3)ACD/LogD (pH 7.4): 3.163; (4)ACD/BCF (pH 5.5): 149.118; (5)ACD/BCF (pH 7.4): 149.118; (6)ACD/KOC (pH 5.5): 1251.474; (7)ACD/KOC (pH 7.4): 1251.474; (8)Index of Refraction: 1.433; (9)Molar Refractivity: 27.67 cm3; (10)Molar Volume: 106.454 cm3; (11)Polarizability: 10.969×10-24cm3; (12)Surface Tension: 25.943 dyne/cm; (13)Density: 0.791 g/cm3; (14)Enthalpy of Vaporization: 29.97 kJ/mol; (15)Boiling Point: 80.719 °C at 760 mmHg; (16)Vapour Pressure: 93.669 mmHg at 25°C.

Preparation: this chemical can be quantitatively produced from benzene by hydrogenation over either a nickel or a platinum catalyst at 210 °C  and 350 to 500 psi hydrogen. Several reactors may be used in series and the yield is over 99 percent.
C6H6 + 3H2 → C6H12

Uses of Cyclohexane: commercially most of cyclohexane produced is converted into cyclohexanone-cyclohexanol mixture (or "KA oil") by catalytic oxidation. KA oil is then used as a raw material for adipic acid and caprolactam. Practically, if the cyclohexanol content of KA oil is higher than cyclohexanone, it is more likely(economical) to be converted into adipic acid, and the reverse case, caprolactam production is more likely. Such ratio in KA oil can be controlled by selecting suitable oxidation catalyst. Some of cyclohexane is used as an organic solvent. Cyclohexane is also used for calibration of Differential scanning calorimetry (DSC) instruments, because of a convenient crystal-crystal transition at -87.1 C.

When you are using this chemical, please be cautious about it as the following:
It is highly flammable and toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment. Please keep away from sources of ignition - No smoking and take precautionary measures against static discharges. Besides, this chemical is irritating to skin and may cause lung damage if swallowed. When you are using it, avoid contact with eyes and avoid release to the environment. Refer to special instructions/safety data sheet. This material and its container must be disposed of as hazardous waste.

You can still convert the following datas into molecular structure:
(1)SMILES: C1CCCCC1
(2)InChI: InChI=1/C6H12/c1-2-4-6-5-3-1/h1-6H2
(3)InChIKey: XDTMQSROBMDMFD-UHFFFAOYAZ
(4)Std. InChI: InChI=1S/C6H12/c1-2-4-6-5-3-1/h1-6H2
(5)Std. InChIKey: XDTMQSROBMDMFD-UHFFFAOYSA-N

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mammal (species unspecified) LC50 inhalation 70gm/m3 (70000mg/m3)   Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 32(10), Pg. 25, 1988.
mouse LCLo inhalation 70gm/m3/2H (70000mg/m3)   "Toxicometric Parameters of Industrial Toxic Chemicals Under Single Exposure," Izmerov, N.F., et al., Moscow, Centre of International Projects, GKNT, 1982Vol. -, Pg. 41, 1982.
mouse LD50 oral 813mg/kg (813mg/kg)   Raw Material Data Handbook, Vol.1: Organic Solvents, 1974. Vol. 1, Pg. 17, 1974.
rabbit LCLo inhalation 89600mg/m3/1H (89600mg/m3) BEHAVIORAL: GENERAL ANESTHETIC

BEHAVIORAL: TREMOR

BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY)
Journal of Industrial Hygiene and Toxicology. Vol. 25, Pg. 323, 1943.
rabbit LD skin > 180gm/kg (180000mg/kg)   Journal of Industrial Hygiene and Toxicology. Vol. 25, Pg. 199, 1943.
rabbit LDLo oral 5500mg/kg (5500mg/kg) GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA" Journal of Industrial Hygiene and Toxicology. Vol. 25, Pg. 199, 1943.
rat LD50 oral 12705mg/kg (12705mg/kg)   Toxicology and Applied Pharmacology. Vol. 19, Pg. 699, 1971.