cyclohexa-1,3-diene
cyclohexene
Conditions | Yield |
---|---|
With samarium diiodide; N,N,N',N'',N''-pentamethylethylene triamine; water In tetrahydrofuran at 20℃; for 0.0833333h; | 100% |
With hydrogen In dichloromethane at 40℃; under 3000.3 Torr; for 0.75h; | 95% |
With 1‑cyanopropyl-3-methylimidazolium tetrafluoroborate; hydrogen; palladium dichloride at 100℃; under 34202.3 Torr; for 4h; Reactivity (does not react); | 90% |
cyclohexene sulfide
cis-2-methyl-3-phenyloxaziridine
A
(Z)-azomethane
B
N,N'-bis(methyl)sulphur di-imide
C
benzaldehyde
D
cyclohexene
Conditions | Yield |
---|---|
In chloroform Mechanism; Ambient temperature; via thionitrosomethane, CH3NS (also used: other oxaziridines and episulfides); | A n/a B 83% C 100% D 100% |
Conditions | Yield |
---|---|
With hydrogen sulfide; triphenylphosphine; methyltrioxorhenium(VII) In [D3]acetonitrile for 0.0833333h; Ambient temperature; | 100% |
With sodium In toluene at 110℃; for 7h; | 99% |
With biphenyl; lithium In 1,2-dimethoxyethane for 8h; Heating; | 73% |
Conditions | Yield |
---|---|
With 1,2-bis(diphenylphosphino)ethane nickel(II) chloride; ethylmagnesium bromide In tetrahydrofuran at 0℃; | 100% |
With 1,2-bis(diphenylphosphino)ethane nickel(II) chloride; tri-n-butyl-tin hydride In tetrahydrofuran for 0.25h; Ambient temperature; | 100% |
With sodium sulfide; cetyltributylphosphonium bromide In toluene at 25℃; for 12h; | 90% |
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide at 20℃; Product distribution; electrolysis, oth. solvent, var. cathodes; | 100% |
Conditions | Yield |
---|---|
With sodium amalgam; chiral Co(II) In tetrahydrofuran-d8 at 20℃; for 6h; deoxygenation; | 100% |
With lithium In tetrahydrofuran for 24h; Heating; | 96% |
With chloro-trimethyl-silane; sodium iodide In acetonitrile for 0.5h; Ambient temperature; | 94% |
(1R,2R)-1-Chloro-2-iodo-cyclohexane
cyclohexene
Conditions | Yield |
---|---|
With 1,2-bis(diphenylphosphino)ethane nickel(II) chloride; lithium triethylborohydride In tetrahydrofuran for 0.5h; Ambient temperature; | 100% |
Conditions | Yield |
---|---|
With thiophenol In acetonitrile at 1℃; for 100h; Product distribution; Elimination; | A 105 % B 100% |
Conditions | Yield |
---|---|
With diazomethyl-trimethyl-silane; ruthenium Schiff-base In toluene at 70℃; for 1h; ring-closing metathesis; | 100% |
With diazomethyl-trimethyl-silane; ruthenium In toluene at 85℃; for 17h; Product distribution; Further Variations:; Catalysts; | 100% |
[2-((2,6-iPr2-Ph-imino)methyl)phenol][p-cymene][=CHPh]Ru2Cl3 In various solvent(s) at 70℃; for 4h; Product distribution; Further Variations:; Catalysts; Temperatures; | 100% |
A
bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]
B
cyclohexene
Conditions | Yield |
---|---|
With HCl In pentane (N2); HCl gas bubbled through complex soln.; | A 93% B 100% |
Conditions | Yield |
---|---|
With sulfuric acid at 250℃; for 0.5h; | 99% |
for 2h; Temperature; Heating; | 98% |
With Nafion/SiO2 at 200℃; under 15001.5 Torr; for 6h; | 90.3% |
bis(triphenylphosphoranylidene)ammonium bromide
B
cyclohexene
Conditions | Yield |
---|---|
In dichloromethane-d2 N2, in an NMR-tube, frozen in liquid N2, CD2Cl2 and PPNBr added, kept at-40°C for 12 h; not isolated, NMR; | A 99% B 57% |
Conditions | Yield |
---|---|
With C24H72Ba2N4Si8 In (2)H8-toluene at 120℃; for 16h; Inert atmosphere; Schlenk technique; Sealed tube; | A 99% B n/a |
cyclohexa-1,4-diene
1-Phenylcyclohexene
A
1-phenyl-1-cyclohexane
B
cyclohexene
Conditions | Yield |
---|---|
With C24H72Ba2N4Si8 In (2)H8-toluene at 120℃; for 3h; Inert atmosphere; Schlenk technique; Sealed tube; | A 99% B n/a |
norborn-2-ene
cyclohexa-1,4-diene
A
norbornene
B
cyclohexene
Conditions | Yield |
---|---|
With C24H72Ba2N4Si8 In (2)H8-toluene at 120℃; for 5h; Inert atmosphere; Schlenk technique; Sealed tube; | A 99% B n/a |
aniline
A
cyclohexane
B
cyclohexylamine
C
N-cyclohexyl-cyclohexanamine
D
cyclohexene
Conditions | Yield |
---|---|
With ammonia; hydrogen at 180 - 200℃; | A n/a B 98.4% C 0.08% D n/a |
With hydrogen at 160 - 200℃; under 150015 Torr; | A n/a B 95.9% C 0.45% D n/a |
Conditions | Yield |
---|---|
With sodium hydroxide; 2,2,2-trifluoroethanol; tetrabutylammomium bromide In 1,2-dichloro-benzene at 73 - 75℃; for 0.5h; phase transfer conditions; | 98% |
With sodium hydroxide; 2,2,2-trifluoroethanol; tetrabutylammomium bromide In 1,2-dichloro-benzene at 73 - 75℃; for 0.5h; phase transfer conditions; | 98% |
With Amberlyst A 26; carbonate form In benzene for 5h; Heating; | 88% |
cis-2-(trimethylsilyl)cyclohexyl trifluoroacetate
A
cyclohexene
B
cyclohexanol
Conditions | Yield |
---|---|
In ethanol at 65℃; Kinetics; ΔH, ΔG, ΔS (excit.); | A 98% B n/a |
In water at 60℃; Kinetics; | A 9.2% B n/a |
Conditions | Yield |
---|---|
With HCl In pentane (N2); HCl gas bubbled through complex soln.; | A 90% B 98% |
Conditions | Yield |
---|---|
With hydrogen at 199.84℃; for 6h; Catalytic behavior; | 95.8% |
With phenylsilane; C28H16F24O8S2Si In 1,2-dichloro-benzene at 100℃; for 72h; Inert atmosphere; | 61% |
With fired clay fragments at 250 - 300℃; | |
Multi-step reaction with 3 steps 1: diethyl ether; sodium; alcohol / Reagens 4: Kaliumcarbonat 2: fuming hydrochloric acid / 100 °C 3: quinoline View Scheme | |
Multi-step reaction with 2 steps 1: PCl5 2: sodium; methanol View Scheme |
Conditions | Yield |
---|---|
With hydrogen; palladium dichloride In N,N-dimethyl-formamide under 18751.5 Torr; for 0.333333h; Product distribution; Ambient temperature; various time; | A 0.05% B 95.6% |
With ammonium acetate In methanol Electrochemical reaction; | A 88% B 12% |
With hydrogen; (η3-C3H5)Co[P(OMe)3]3 for 24h; Ambient temperature; | A 7.6% B 48.3% |
Conditions | Yield |
---|---|
With hydrogen; ytterbium at 393℃; under 22501.8 Torr; for 3h; | 95% |
With hydrogenchloride; <η6-C6Me6Ru η4-C6H8> | 92% |
With hydrogen; 2,2'-iminobis[ethanol]; zinc(II) sulfate; zirconium(IV) oxide In water at 150℃; under 37503.8 Torr; Autoclave; | 63.6% |
B
P(C6H5)3C6H11(1+)*BF4(1-) = P(C6H5)3C6H11BF4
C
fluorocyclohexane
D
cyclohexene
Conditions | Yield |
---|---|
With triphenylphosphine In dichloromethane-d2 N2, frozen in liquid N2, CD2CL2 and solid PPh3 added, slowly warmed to 0°C; not isolated, NMR, GLC; | A 95% B 24% C 24% D 30% |
ethanol
sodium thiophenolate
1,2-bis(5-thianthreniumyl)cyclohexane diperchlorate
A
2-ethoxycyclohex-1-ene
B
diphenyldisulfane
C
Thianthrene
D
cyclohexene
Conditions | Yield |
---|---|
In ethanol for 360h; Ambient temperature; | A 2% B 81% C 94% D 59% |
sodium thiophenolate
1,2-bis(5-thianthreniumyl)cyclohexane diperchlorate
A
diphenyldisulfane
B
Thianthrene
C
cyclohexene
Conditions | Yield |
---|---|
In dimethyl sulfoxide for 20h; Ambient temperature; | A 84% B 94% C 61% |
Conditions | Yield |
---|---|
With sodium hydride In N,N,N,N,N,N-hexamethylphosphoric triamide at 20℃; for 14h; | 94% |
With N,N,N,N,N,N-hexamethylphosphoric triamide; sodium hydride at 0 - 20℃; Inert atmosphere; | 94% |
With potassium fluoride In N,N,N,N,N,N-hexamethylphosphoric triamide at 65℃; for 5h; | 90% |
B
cyclohexene
Conditions | Yield |
---|---|
In benzene (N2); Ir complex soln. treated with BF3*2H2O, stirred for 12 h at 20°C; C6H6 and ether added to H2O layer; | A 94% B 63% |
7,7-dimorpholino-cis-bicyclo<4.1.0>heptane
A
5-morpholino-2,3,6,7-tetrahydro-1,4-oxazepine
B
cyclohexene
Conditions | Yield |
---|---|
at 700℃; under 1E-05 Torr; | A 70% B 93% |
acetic acid
cyclohexene
rac-3-acetoxycyclohexene
Conditions | Yield |
---|---|
With palladium diacetate; N,N'-bis(salicylidene)-1,2-phenylene diaminocobalt(II); lithium acetate; oxygen; hydroquinone at 60℃; under 760 Torr; Product distribution; var. metal macrocyclic complexes, var. metal complexes concentration; | 100% |
With palladium diacetate; N,N'-bis(salicylidene)-1,2-phenylene diaminocobalt(II); lithium acetate; oxygen; hydroquinone at 60℃; under 760 Torr; for 20.2h; | 100% |
With manganese(IV) oxide; palladium diacetate; p-benzoquinone at 60℃; for 17h; | 97% |
Conditions | Yield |
---|---|
In decane; toluene at 30℃; | 100% |
With [Cu(4-methyl-1,3-bis(2-pyridylimino)isoindole)(OAc)] In water | 86% |
With pyrazolate-based cobalt(II)-containing MFU-1 metal-organic framework at 70℃; for 2h; | 11.9% |
Conditions | Yield |
---|---|
With sodium hydroxide; Sucrose-ethyleneoxide adducts In chloroform at 20℃; for 2h; Product distribution; further catalysts: PEG, DB18K6; further objects of study: phase-transfer catalysis;; | 100% |
With sodium hydroxide; Sucrose-ethyleneoxide adducts In chloroform at 20℃; for 2h; Product distribution; further catalysts: PEG, DB18K6; | 100% |
With potassium hydroxide; 18-crown-6 ether In dichloromethane at 40℃; for 6h; | 98% |
cyclohexene
diethylazodicarboxylate
Diethyl 1-(2-cyclohexen-1-yl)-1,2-hydrazinedicarboxylate
Conditions | Yield |
---|---|
With tin(IV) chloride In dichloromethane at -78℃; | 100% |
With tin(IV) chloride In dichloromethane at -60℃; for 0.0833333h; | 77% |
Conditions | Yield |
---|---|
trans-2 In acetonitrile for 4h; Ambient temperature; | 100% |
With tert.-butylhydroperoxide; C29H26CuN6O2 In acetonitrile for 4h; Inert atmosphere; Reflux; | 100% |
With tert.-butylhydroperoxide; oxygen In acetonitrile at 85℃; for 12h; Catalytic behavior; Reagent/catalyst; Solvent; Time; | 99% |
Conditions | Yield |
---|---|
With water; 4-methylmorpholine N-oxide; osmium; Cu-Al-hydrotalcite In toluene at 60℃; for 4.5h; | 100% |
With N-methyl-2-indolinone; fluorous OsO4 In water; acetone; tert-butyl alcohol at 20℃; for 36h; | 100% |
With 4-methylmorpholine N-oxide; In water; acetone Ambient temperature; | 95% |
Conditions | Yield |
---|---|
With sodium periodate; C31H29Br2N3Ru*CH2Cl2 In water; ethyl acetate; acetonitrile at 25℃; for 0.5h; Inert atmosphere; Schlenk technique; | 100% |
With 1H-imidazole; sodium periodate; MnCl-TPP-(PEO750)4 In water; acetonitrile at 20℃; for 24h; | 97% |
With 1-(3-sulfopropyl)-3-methylimidazolium periodate In water at 35℃; for 36h; Reagent/catalyst; Temperature; | 93% |
Conditions | Yield |
---|---|
With methyl cyanoformate; sodium decatungstate In acetonitrile at 8℃; for 90h; Irradiation; | 100% |
at 10℃; for 25h; Product distribution; Irradiation; | |
With phosphorus pentoxide; benzene |
Conditions | Yield |
---|---|
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% |
cyclohexene
trans-Di(2-chlorocyclohexyl) sulfide
Conditions | Yield |
---|---|
With sulfur dichloride In dichloromethane at 0℃; for 2h; | 100% |
With thiobismorpholine; trichlorophosphate In dichloromethane at -40 - 20℃; | 61% |
With tetrachloromethane; sulfur dichloride at 70 - 80℃; | |
With sulfur tetrachloride | |
With sulfur dichloride |
cyclohexene
2-bromocyclocyclohexanol
Conditions | Yield |
---|---|
With N-Bromosuccinimide In water at 0 - 25℃; | 100% |
With N-Bromosuccinimide; water In 1,2-dimethoxyethane 1.) 0 deg C, 30 min, 2.) 20 deg C, 60 min; | 99% |
With tribromo-isocyanuric acid In acetone at 20℃; for 0.0833333h; | 91% |
Conditions | Yield |
---|---|
With bromine; thallium(I) acetate In tetrachloromethane for 0.583333h; Ambient temperature; | 100% |
With bromine In Hexadecane for 0.5h; Cooling; | 100% |
With tetra-N-butylammonium tribromide In chloroform Ambient temperature; ultrasonic irradiation; | 99% |
Conditions | Yield |
---|---|
With dihydrogen peroxide; trioctylmethylammonium hydrogen tungstate; phenylphosphonate In 1,4-dioxane at 70℃; for 0.8h; | 100% |
With tert.-butylhydroperoxide; molybdenum(VI) oxide at 80℃; for 1h; | 100% |
With tert.-butylhydroperoxide; C15H12ClMoN3O7 In methanol; dichloromethane for 1h; Reagent/catalyst; | 100% |
Conditions | Yield |
---|---|
With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In tetrachloromethane at 80℃; for 1.5h; Wohl-Ziegler allylic bromination; | 100% |
With N-Bromosuccinimide; 1,3-di-n-butyl-imidazolium tetrafluoroborate at 28 - 35℃; for 0.0833333h; | 85% |
With N-Bromosuccinimide Wohl-Ziegler Bromination; Reflux; | 84% |
Conditions | Yield |
---|---|
With dibenzoyl peroxide at 90℃; for 10h; | 100% |
at 27℃; for 22h; (γ-irradiation); | |
Irradiation; |
Conditions | Yield |
---|---|
With N-Bromosuccinimide | 100% |
With sodium bromide at 60℃; electrolysis in undivided cell, Pt-anode, Cu-Zn-cathode; | 80% |
With tert-butyl hypobromite | |
With tBuBrO |
(diethoxyphosphinothioyl)sulfenyl chloride
cyclohexene
1-chloro-2-(S-diethoxythiophosphoro)cyclohexane
Conditions | Yield |
---|---|
100% |
cyclohexene
(1R,2R)-1-Chloro-2-iodo-cyclohexane
Conditions | Yield |
---|---|
With K(1+)*Cl2I(1-) In tetrachloromethane for 0.333333h; | 100% |
With hydrogenchloride; potassium iodate; iodine In water at 5℃; for 0.5h; iodochlorination; | 98% |
With iodine; copper dichloride In pentane for 4h; Ambient temperature; | 95% |
5-Phenyl-1H-tetrazole
cyclohexene
2-cyclohexyl-5-phenyl-2H-tetrazole
Conditions | Yield |
---|---|
With sulfuric acid | 100% |
4-Phenyl-1,2,4-triazolidine-3,5-dione
cyclohexene
1-(cyclohex-2-enyl)-4-phenyl-1,2,4-triazolidine-3,5-dione
Conditions | Yield |
---|---|
In dichloromethane | 100% |
In dichloromethane Ambient temperature; | 89% |
In benzene at 25℃; Rate constant; other solvent; | |
In benzene at 25℃; Rate constant; other solvent: CH2Cl2; | |
In toluene at 25℃; under 1490400 Torr; Kinetics; Temperature; Pressure; Concentration; |
Conditions | Yield |
---|---|
With ammonium cerium(IV) nitrate; iodine In acetonitrile for 5h; Heating; | 100% |
Conditions | Yield |
---|---|
With N-Bromosuccinimide at 0℃; for 1h; | 100% |
With N-Bromosuccinimide In dichloromethane 1.) -20 deg C, 2 h, 2.) 15 deg C; | 83% |
With N-Bromosuccinimide In dichloromethane at -20 - 23℃; for 17.5h; Inert atmosphere; | 63% |
Conditions | Yield |
---|---|
With ammonium cerium(IV) nitrate; iodine for 5h; Heating; | 100% |
With ammonium cerium(IV) nitrate; iodine for 10h; Mechanism; Heating; other substrate; | 80% |
With ammonium cerium(IV) nitrate; iodine for 10h; Heating; | 80% |
Conditions | Yield |
---|---|
In benzene for 1.5h; Irradiation; | 100% |
Reported in EPA TSCA Inventory.
Hazard Codes: F, Xn
Risk Statements: 11-21/22-65
R11:Highly flammable.
R21/22:Harmful in contact with skin and if swallowed.
R65:Harmful: may cause lung damage if swallowed.
Safety Statements: 16-29-33-36/37
S16:Keep away from sources of ignition.
S29:Do not empty into drains.
S33:Take precautionary measures against static discharges.
S36/37:Wear suitable protective clothing and gloves.
RIDADR: UN 2256 3/PG 2
WGK Germany: 1
RTECS: GW2500000
HazardClass: 3
PackingGroup: II
Moderately toxic by inhalation and ingestion. A very dangerous fire hazard when exposed to flame; can react with oxidizers. Dangerous; keep away from heat and open flame. To fight fire, use foam, CO2, dry chemical.
OSHA PEL: 300 ppm
ACGIH TLV: 300 ppm
DFG MAK: 300 ppm (1000 mg/m3)
DOT Classification: 3; Label: Flammable Liquid
For occupational chemical analysis use NIOSH: Hydrocarbons.
The Cyclohexene ,with the CAS registry number 110-83-8,is also named as 1,2,3,4-Tetrahydrobenzene ; Hexanaphthylene ; NSC 24835 ; Tetrahydrobenzene .It is a colourless liquid. It is insoluble in water. Inhalation of high concentrations may have a narcotic effect. Cyclohexene is highly flammable. And it may react vigorously with strong oxidizing agents. May react exothermically with reducing agents to release hydrogen gas. In the presence of various catalysts (such as acids) or initiators, may undergo exothermic addition polymerization reactions. Oxidizes readily in air to form unstable peroxides that may explode spontaneously. May cause toxic effects if inhaled or absorbed through skin. Inhalation or contact with material may irritate or burn skin and eyes. Fire will produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or suffocation. Runoff from fire control or dilution water may cause pollution. Will be easily ignited by heat, sparks or flames. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapor of Cyclohexene explosion hazard indoors, outdoors or in sewers. Runoff to sewer may create fire or explosion hazard. It may explode when heated.It can be used as solvents, and also used in organic synthesis.
Physical properties about Cyclohexene are:
(1)ACD/LogP: 2.918; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2.92; (4)ACD/LogD (pH 7.4): 2.92; (5)ACD/BCF (pH 5.5): 97.23; (6)ACD/BCF (pH 7.4): 97.23; (7)ACD/KOC (pH 5.5): 921.49; (8)ACD/KOC (pH 7.4): 921.49; (9)#H bond acceptors: 0; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 0; (12)Index of Refraction: 1.459; (13)Molar Refractivity: 27.274 cm3; (14)Molar Volume: 99.748 cm3; (15)Surface Tension: 29.0799999237061 dyne/cm; (16)Density: 0.823 g/cm3; (17)Flash Point: -12.222 °C; (18)Enthalpy of Vaporization: 30.46 kJ/mol; (19)Boiling Point: 85.636 °C at 760 mmHg; (20)Vapour Pressure: 77.0210037231445 mmHg at 25°C.
You can still convert the following datas into molecular structure:
(1)SMILES:C1CCC=CC1;
(2)Std. InChI:InChI=1S/C6H10/c1-2-4-6-5-3-1/h1-2H,3-6H2;
(3)Std. InChIKey:HGCIXCUEYOPUTN-UHFFFAOYSA-N.
Preparation of Cyclohexene:
A common experiment for beginning organic chemistry students is the acid catalyzed dehydration of cyclohexanol with distillative removal of the resulting cyclohexene from the reaction mixture:
Safety Information of Cyclohexenen:
The Cyclohexene is highly flammable. So it should be Keep away from sources of ignition.And it is harmful in contact with skin and if swallowed. When you use it ,wear suitable protective clothing and gloves. Take precautionary measures against static discharges. It is dangers to the environment,so do not empty into drains.
The toxicity data of Cyclohexene as follows:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
guinea pig | LD50 | skin | > 20mL/kg (20mL/kg) | National Technical Information Service. Vol. OTS0556686, | |
mouse | LD50 | oral | > 3200uL/kg (3.2mL/kg) | BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: ATAXIA | National Technical Information Service. Vol. OTS0546026, |
rat | LC | inhalation | > 6370ppm/4H (6370ppm) | BEHAVIORAL: TREMOR BEHAVIORAL: ATAXIA LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES | National Technical Information Service. Vol. OTS0555329, |
rat | LD50 | oral | 2400uL/kg (2.4mL/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: TREMOR BEHAVIORAL: ATAXIA | National Technical Information Service. Vol. OTS0546026, |
rat | LD50 | unreported | 2gm/kg (2000mg/kg) | Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 29(12), Pg. 53, 1985. |
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