nonafluoro-tert-butanesulfenyl chloride
cyclohexane
A
nonafluoro-tert-butanethiol
B
cyclohexyl chloride
Conditions | Yield |
---|---|
A 100% B 100% | |
A 100% B 100% |
Conditions | Yield |
---|---|
With bismuth(III) chloride In tetrachloromethane for 0.0833333h; Heating; | 99% |
With 1,2,3-Benzotriazole; thionyl chloride In dichloromethane at 20℃; Substitution; | 92% |
With triphenylphosphine; zinc(II) chloride; diethylazodicarboxylate In tetrahydrofuran for 2h; Ambient temperature; | 90% |
Conditions | Yield |
---|---|
With bismuth(III) chloride In 1,2-dichloro-ethane for 0.25h; Heating; | 98% |
Conditions | Yield |
---|---|
With hydrogenchloride; tetrabutyl-ammonium chloride; sodium chloride In water at 20℃; for 5h; Reagent/catalyst; | 97% |
With hydrogenchloride; potassium chloride; tetrabutyl-ammonium chloride In water at 20℃; Irradiation; Green chemistry; | 95% |
With sodium hypochlorite In water; acetone at 20℃; for 2h; Reagent/catalyst; Solvent; Time; Inert atmosphere; | 93% |
cyclohexane
dichlorofluoromethanesulphenyl chloride
A
cyclohexyl chloride
B
bis(dichlorofluoromethyl)disulfane
C
Dichlorfluormethyl-cyclohexylsulfid
Conditions | Yield |
---|---|
A 63.6% B 97% C 3% | |
A 63.6% B 97% C 3% |
Conditions | Yield |
---|---|
With ethanol; trichlorovinylsilane; tin(IV) chloride for 1h; Ambient temperature; | 90% |
With dichloromethane; RhCl(PPh3)3 | 72% |
With chloro-trimethyl-silane; water for 15h; Ambient temperature; | 70% |
Conditions | Yield |
---|---|
With hydrogenchloride at 105℃; for 3h; | 90% |
With boron trichloride In hexane at 0℃; for 0.0833333h; | 78% |
With diethylaluminium chloride In hexane at -78℃; for 0.166667h; | 74 % Chromat. |
Conditions | Yield |
---|---|
With CPT | A n/a B 90% |
chlorodifluoromethansulfenylchloride
cyclohexane
A
cyclohexyl chloride
B
bis(chlorodifluoromethyl)disulfane
C
(Chloro-difluoro-methylsulfanyl)-cyclohexane
D
benzyl chloro-difluoromethyl sulfide
Conditions | Yield |
---|---|
A 39.4% B 88.4% C 11.6% D 65% | |
A 39.4% B 88.4% C 11.6% D 65% |
cyclohexyl chloride
Conditions | Yield |
---|---|
With 1,4-diaza-bicyclo[2.2.2]octane; tetrachloromethane In water; tert-butyl alcohol for 4h; Irradiation; | 86% |
heptafluoro-propane-1-sulphenic acid chloride
cyclohexane
A
bis(perfluoro-n-propyl)disulfane
B
cyclohexyl chloride
C
heptafluoro-n-propyl cyclohexyl sulfide
Conditions | Yield |
---|---|
A 85.7% B 43.2% C 14.3% | |
A 85.7% B 43.2% C 14.3% | |
for 0.1h; Mechanism; Irradiation; effect of bis(trifluoromethyl) disulfide; |
2-methoxycyclohexane
A
cyclohexyl chloride
B
benzeneacetic acid methyl ester
Conditions | Yield |
---|---|
With phenylacetyl chloride; zinc In Petroleum ether at 28℃; for 4h; Yields of byproduct given; | A 84% B n/a |
2-methoxycyclohexane
phenylacetyl chloride
A
cyclohexyl chloride
B
benzeneacetic acid methyl ester
Conditions | Yield |
---|---|
With zinc In Petroleum ether at 28℃; for 4h; Yields of byproduct given; | A n/a B 84% |
Conditions | Yield |
---|---|
With 1-chloro-1-(dimethylamino)-2-methyl-1-propene In dichloromethane 1.) 0 deg C; 2.) rt., 3h; | A 18 % Spectr. B 82% |
With hydrogenchloride | |
With aluminium trichloride Erwaermen auf dem Dampfbad; |
A
2-methyl-1,2-benzisothiazole-3(2H)-one
B
cyclohexyl chloride
D
cyclohexene
Conditions | Yield |
---|---|
With thionyl chloride In dichloromethane for 1h; Mechanism; Product distribution; Heating; also pyrolysis in toluene, 110 deg C, 20 h, without SOCl2; further o-(N-methylcarbamoyl)phenyl sulphoxides; | A 81% B 11% C 16% D 67% |
With thionyl chloride In dichloromethane for 1h; Heating; | A 81% B 11% C 16% D 67% |
(1R,2R)-1-Chloro-2-iodo-cyclohexane
cyclohexyl chloride
Conditions | Yield |
---|---|
With 1,2-bis(diphenylphosphino)ethane nickel(II) chloride; tri-n-butyl-tin hydride In tetrahydrofuran for 0.25h; Ambient temperature; | 80% |
cyclohexane
benzyloxychlorocarbene
A
cyclohexyl chloride
B
benzyl chloride
C
cyclohexanol
Conditions | Yield |
---|---|
at 25℃; Photolysis; | A 9% B 80% C 11% |
Conditions | Yield |
---|---|
In benzene at 30℃; Kinetics; Solvent; Temperature; Inert atmosphere; Schlenk technique; | A n/a B 70% |
cyclohexane
1-Phenylethanol
A
cyclohexyl chloride
B
tert-butylamine hydrochloride
C
acetophenone
Conditions | Yield |
---|---|
With N,N-dichloro-t-butylamine at 20℃; for 1h; Irradiation; | A 68% B n/a C n/a |
Conditions | Yield |
---|---|
With dichloromethylsilane; iron(III) chloride In 1,2-dimethoxyethane for 6h; Heating; | 66% |
Multi-step reaction with 2 steps 1: diethyl ether; sodium; alcohol / Reagens 4: Kaliumcarbonat 2: fuming hydrochloric acid / 100 °C View Scheme | |
Stage #1: cyclohexanone With iron(III) chloride In ethyl acetate at 20℃; for 0.0166667h; Stage #2: With dimethylmonochlorosilane In ethyl acetate at 20℃; |
cyclohexane
heptafluoropropane-2-sulphenic acid chloride
A
cyclohexyl chloride
B
bis(perfluoroisopropyl) disulfide
C
heptafluoropropane-2-thiol
D
Heptafluorisopropylcyclohexylsulfid
Conditions | Yield |
---|---|
A 37.7% B 65% C n/a D 0.5% | |
A 37.7% B 65% C n/a D 0.5% |
Benzotrichlorid
cyclohexanol
A
benzylidene dichloride
B
cyclohexyl chloride
Conditions | Yield |
---|---|
With TOP; phenylsilane In neat (no solvent) at 100℃; for 24h; Appel Halogenation; Inert atmosphere; | A n/a B 57% |
Conditions | Yield |
---|---|
With tert.-butylhydroperoxide; (FeCl2(C6H6N2CO)(CH3)2(C5H4N)2(C(O)OCH3)2); tetrabutyl-ammonium chloride In acetonitrile at 25℃; for 0.583333h; Inert atmosphere; chemoselective reaction; | A 5.1% B 55.4% |
With [FeIV(1,1-di(pyridin-2-yl)-N,N-bis(quinolin-2-ylmethyl)methanamine)(O)]2+; [FeII(1,1-di(pyridin-2-yl)-N,N-bis(quinolin-2-ylmethyl)methanamine)(Cl)]Cl In acetonitrile at 25℃; for 0.5h; Inert atmosphere; Glovebox; | A 52% B n/a |
With 5,10,15,20-tetraphenyl-21 H,23-H-porphine manganese(III)chloride; iodosylbenzene In dichloromethane; water for 12h; | A 18% B 30% |
Trifluoromethylsulfenyl chloride
cyclohexane
A
Bis(trifluoromethyl)disulfid
B
cyclohexyl(trifluoromethyl)sulfane
C
cyclohexyl chloride
Conditions | Yield |
---|---|
byproducts: HCl; Irradiation (UV/VIS); | A 35% B 45% C 28% |
byproducts: HCl; Irradiation (UV/VIS); | A 35% B 45% C 28% |
for 0.2h; Mechanism; Irradiation; effect of bis(heptafluoro-n-propyl) disulfide; |
tetraethylammonium chloride
3-chloro-benzenecarboperoxoic acid
A
cyclohexyl chloride
B
3-chloro-benzoic acid ethyl ester
Conditions | Yield |
---|---|
With cyclohexane In acetonitrile at 20℃; for 3h; Yields of byproduct given; | A n/a B 38% |
cyclohexane
A
cyclohexyl chloride
B
cyclohexanone
C
cyclohexanol
Conditions | Yield |
---|---|
With chloroform; pyrimido<5,4-g>pteridine N-oxide for 3h; Product distribution; Mechanism; Irradiation; | A 11% B 12% C 37% |
With [oxoiron(IV)(tris-(quinolyl-2-methyl)amine)(chloride)](1+) In [D3]acetonitrile at -40℃; Reagent/catalyst; | A 35% B 3% C 7% |
With barium hexaferrite; acetic acid; magnesium chloride In dichloromethane at 23℃; for 2h; Product distribution; Further Variations:; Reagents; | A 31% B 13% C 10% |
Conditions | Yield |
---|---|
With potassium permanganate; aluminium trichloride In acetonitrile for 0.5h; | A 35% B 15% |
With [oxoiron(IV)(tris(pyridyl-2-methyl)amine)(chloride)](triflate) In [D3]acetonitrile at 25℃; Inert atmosphere; | A 11% B 2% |
With cis-VI(6,6'-Cl2bpy)2O2> In tetrachloromethane; acetonitrile at 20℃; for 0.5h; Oxidation; | A 0.5 % Chromat. B 50 % Chromat. |
With peracetic acid; triethylamine hydrochloride; acetic acid In acetonitrile at 22℃; Inert atmosphere; sealed system; |
tetrachloromethane
cyclohexene
A
cyclohexyl chloride
trans-1-trichloromethyl-2-chlorocyclohexane
Conditions | Yield |
---|---|
With tris(triphenylphosphine)ruthenium(II) chloride; water at 150℃; for 6h; Autoclave; | A n/a B 25% C 25% |
cyclohexane
A
cyclohexyl chloride
B
tert-butyl cyclohexyl peroxide
C
cyclohexanone
D
cyclohexanol
Conditions | Yield |
---|---|
With Co(III)(BPI)(OAc)(OO-tBu) at 60℃; for 2h; Product distribution; stoichiometric oxidation by various cobalt(III)alkylperoxy complexes, solvents; | A n/a B 18% C 24% D 18% |
tert.-butylhydroperoxide
cyclohexane
acrylonitrile
A
cyclohexyl chloride
B
2-Chlor-3-cyclohexylpropiononitril
C
2-tert-Butylperoxy-3-cyclohexyl-propionitrile
Conditions | Yield |
---|---|
With acetic acid; ferric nitrate; copper dichloride In pyridine at 60℃; Product distribution; Mechanism; further with LiCl; | A 15.8% B 8.7% C 3.1% |
Conditions | Yield |
---|---|
With hydrogen bromide; ferric(III) bromide In dichloromethane at 25℃; for 0.3h; | 99% |
With hydrogen bromide at 105℃; for 4h; | 90% |
With ferric(III) bromide; hydrogen bromide In dichloromethane at 25℃; for 2h; | |
With hydrogen bromide; cetyltributylphosphonium bromide at 105℃; for 7h; | 80 % Chromat. |
With ferric(III) bromide; hydrogen bromide In dichloromethane at 25℃; for 0.3h; Product distribution; Mechanism; other alkyl chlorides; other hydrogen halide; also without HBr; var. reaction conditions; | 99 % Chromat. |
cyclohexyl chloride
N-<(S)-1-phenylethyl>-2-pyridinecarboxamide
Conditions | Yield |
---|---|
With N,N,N,N,-tetramethylethylenediamine; ethylmagnesium bromide; manganese(ll) chloride In tetrahydrofuran at 60℃; for 14h; Catalytic behavior; Reagent/catalyst; Schlenk technique; Inert atmosphere; chemoselective reaction; | 99% |
cyclohexyl chloride
4-methoxyphenyl magnesium bromide
4-cyclohexylanisole
Conditions | Yield |
---|---|
With iron(III) chloride; N,N′-bis(2,6-diisopropylphenyl)imidazol-2-ylidene hydrochloride In tetrahydrofuran at 0 - 40℃; for 1.66667h; | 98% |
Stage #1: cyclohexyl chloride With [1,3-bis(3,5-di-tert-butyl-2-hydroxybenzyl)benzimidazolium][FeCl4] In diethyl ether at 0℃; for 0.0333333h; Schlenk technique; Inert atmosphere; Stage #2: 4-methoxyphenyl magnesium bromide In diethyl ether at 0 - 30℃; for 2h; Temperature; Schlenk technique; Inert atmosphere; | 86% |
With iron(III) chloride; triethylamine In diethyl ether for 0.5h; Grignard cross-coupling reaction; Heating; |
Conditions | Yield |
---|---|
With tetra-(n-butyl)ammonium iodide In acetonitrile at 20℃; for 4h; Reagent/catalyst; Inert atmosphere; UV-irradiation; | 98% |
Conditions | Yield |
---|---|
With aluminum (III) chloride at 0 - 20℃; for 4h; Friedel-Crafts Alkylation; | 95% |
With aluminum (III) chloride at 3 - 20℃; |
cyclohexyl chloride
4-flourophenylmagnesium bromide
1-cyclohexyl-4-fluorobenzene
Conditions | Yield |
---|---|
With iron(III) chloride; N,N′-bis(2,6-diisopropylphenyl)imidazol-2-ylidene hydrochloride In tetrahydrofuran at 0 - 40℃; for 1.66667h; | 95% |
Stage #1: cyclohexyl chloride With [1,3-bis(3,5-di-tert-butyl-2-hydroxybenzyl)benzimidazolium][FeCl4] In diethyl ether at 0℃; for 0.0333333h; Schlenk technique; Inert atmosphere; Stage #2: 4-flourophenylmagnesium bromide In diethyl ether at 0 - 30℃; for 2h; Temperature; Schlenk technique; Inert atmosphere; | 78% |
cyclohexyl chloride
1-(4-butoxyphenyl)-1-cyclohexyl-3-[4-(2,5-dimethylphenyl)piperazin-1-yl]-2-phenylpropan-1-one
Conditions | Yield |
---|---|
Stage #1: cyclohexyl chloride With magnesium In diethyl ether Stage #2: With 1-(4-butoxyphenyl)-3-[4-(2,5-dimethylphenyl)piperazin-1-yl]-2-phenylpropan-1-one In diethyl ether for 6h; Heating; | 95% |
Conditions | Yield |
---|---|
With zinc perchlorate In neat (no solvent) at 80℃; for 3h; Ritter Amidation; | 94% |
With iron(II) chloride tetrahydrate In neat (no solvent) at 80℃; for 4h; Ritter Amidation; | 94% |
N-(2-phenylethyl)pyridine-2-carboxamide
cyclohexyl chloride
Conditions | Yield |
---|---|
With N,N,N,N,-tetramethylethylenediamine; ethylmagnesium bromide; manganese(ll) chloride In tetrahydrofuran at 60℃; for 14h; Schlenk technique; Inert atmosphere; chemoselective reaction; | 94% |
Conditions | Yield |
---|---|
With copper(l) iodide; C21H23ClNiP2S; caesium carbonate; sodium iodide In dimethyl sulfoxide at 50℃; for 12h; Sonogashira Cross-Coupling; Schlenk technique; Inert atmosphere; | 94% |
2-cyclohex-1-enyl-pyridine
cyclohexyl chloride
Conditions | Yield |
---|---|
With N,N,N,N,-tetramethylethylenediamine; neopentylmagnesium bromide; cobalt(II) bromide; 1,3-diisopropyl-1H-benzo[d]imidazol-3-ium bromide In tetrahydrofuran at 0 - 20℃; for 6h; Catalytic behavior; Reagent/catalyst; Temperature; Schlenk technique; | 92% |
cyclohexyl chloride
N-butyl-pyridine-2-carboxylic acid amide
Conditions | Yield |
---|---|
With N,N,N,N,-tetramethylethylenediamine; ethylmagnesium bromide; manganese(ll) chloride In tetrahydrofuran at 60℃; for 14h; Schlenk technique; Inert atmosphere; chemoselective reaction; | 92% |
cyclohexyl chloride
1-phenyl-3-piperidino-propan-1-one; hydrochloride
trihexylphenidyl hydrochloride
Conditions | Yield |
---|---|
Stage #1: cyclohexyl chloride With iodine; magnesium In 1,2-dimethoxyethane; tert-butyl methyl ether at 45 - 55℃; for 2h; Sealed tube; Inert atmosphere; Large scale; Stage #2: 1-phenyl-3-piperidino-propan-1-one; hydrochloride In 1,2-dimethoxyethane; tert-butyl methyl ether at 5 - 10℃; for 2h; Solvent; Sealed tube; Inert atmosphere; Large scale; | 90.5% |
Stage #1: cyclohexyl chloride With magnesium In tetrahydrofuran; ethyl bromide at 45 - 65℃; for 3h; Stage #2: 1-phenyl-3-piperidino-propan-1-one; hydrochloride In tetrahydrofuran; ethyl bromide at 65℃; for 4h; Stage #3: With hydrogenchloride In tetrahydrofuran; ethyl bromide; water at 65℃; for 0.8h; Temperature; | 70.3% |
Conditions | Yield |
---|---|
With hydrogen iodide; cetyltributylphosphonium bromide at 105℃; for 7h; | 90% |
With hydrogen iodide at 105℃; for 2.5h; | 85% |
With hydrogen iodide |
cyclohexyl chloride
(-)-(2S)-trifluoromethanesulfonyloxy-propionic acid tert-butyl ester
(+)-(2S)-cyclohexyl-propionic acid tert-butyl ester
Conditions | Yield |
---|---|
Stage #1: cyclohexyl chloride With magnesium In tetrahydrofuran Inert atmosphere; Stage #2: (-)-(2S)-trifluoromethanesulfonyloxy-propionic acid tert-butyl ester With zinc(II) chloride In tetrahydrofuran at 0℃; for 3h; Inert atmosphere; optical yield given as %ee; enantiospecific reaction; | 90% |
Conditions | Yield |
---|---|
With aluminum (III) chloride at 0 - 20℃; for 4h; Friedel-Crafts Alkylation; | 90% |
With aluminum (III) chloride at 0 - 20℃; for 5h; | 90% |
cyclohexyl chloride
para-methylphenylmagnesium bromide
1-cyclohexyl-4-methylbenzene
Conditions | Yield |
---|---|
Stage #1: cyclohexyl chloride With [1,3-bis(3,5-di-tert-butyl-2-hydroxybenzyl)benzimidazolium][FeCl4] In diethyl ether at 0℃; for 0.0333333h; Schlenk technique; Inert atmosphere; Stage #2: para-methylphenylmagnesium bromide In diethyl ether at 0 - 30℃; for 2h; Temperature; Reagent/catalyst; Schlenk technique; Inert atmosphere; | 89% |
With C33H49N2O2(1+)*Cl4Fe(1-) In diethyl ether Reagent/catalyst; Grignard Reaction; | 77% |
With butylmethylimidazolium tetrachloroferrate In diethyl ether at 0 - 20℃; | 75% |
Conditions | Yield |
---|---|
With potassium fluoride on basic alumina In 2-methyltetrahydrofuran at 90℃; for 12h; Inert atmosphere; chemoselective reaction; | 89% |
carbon dioxide
cyclohexyl chloride
aniline
O-cyclohexyl N-phenylcarbamate
Conditions | Yield |
---|---|
With choline chloride * 2ZnCl2 at 20℃; under 760.051 Torr; for 2h; Green chemistry; | 89% |
Conditions | Yield |
---|---|
With oxygen; kieselguhr; copper(l) chloride In hexane for 3h; Oxidation; Heating; | 88% |
Stage #1: cyclohexyl chloride With sodium hydroxide In water at 45 - 50℃; for 2.5h; Stage #2: With quinolinium chlorochromate(VI) In water for 18h; | 37% |
With pumice stone; vanadia at 350℃; beim Leiten im Gemisch mit Luft und Wasserdampf; |
cyclohexyl chloride
Conditions | Yield |
---|---|
Stage #1: cyclohexyl chloride With naphthalene; lithium In tetrahydrofuran at -78℃; for 3h; Stage #2: (2SP,4R,5S)-(-)-3,4-dimethyl-2,5-diphenyl-1,3,2-oxazaphospholidine borane In tetrahydrofuran at -78℃; Further stages.; | 88% |
Stage #1: cyclohexyl chloride With lithium In Petroleum ether for 5h; Heating; Stage #2: (2SP,4R,5S)-(-)-3,4-dimethyl-2,5-diphenyl-1,3,2-oxazaphospholidine borane In tetrahydrofuran; Petroleum ether at -78 - 0℃; | 87% |
Molecule structure of Chlorocyclohexane (CAS NO.542-18-7):
IUPAC Name: Chlorocyclohexane
Molecular Formula: C6H11Cl
Molecular Weight: 118.62 g/mol
Density: 1 g/mL at 25 °C(lit.)
Melting Point: -44 °C
Boiling Point: 142 °C at 760 mmHg
Flash Point: 28.9 °C
Storage Temp.: Flammables area
Water Solubility: 0.02 g/L (20 °C)
Index of Refraction: 1.451
Molar Refractivity: 32.58 cm3
Molar Volume: 120.9 cm3
Surface Tension: 27.7 dyne/cm
XLogP3: 3
Exact Mass: 118.054928
MonoIsotopic Mass: 118.054928
Canonical SMILES: C1CCC(CC1)Cl
InChI: InChI=1S/C6H11Cl/c7-6-4-2-1-3-5-6/h6H,1-5H2
InChIKey: UNFUYWDGSFDHCW-UHFFFAOYSA-N
EINECS: 208-806-6
Product Categories: CHLORO ALKANE COMPOUNDS
Chlorocyclohexane (CAS NO.542-18-7) is used as pharmaceutical intermediates. It is also used in organic synthesis.
1. | ihl-rat LCLo:31 g/m3 | GTPZAB Gigiena Truda i Professionalnye Zabolevaniia. Labor Hygiene and Occupational Diseases. 10 (1)(1966),49. | ||
2. | ihl-mus LC50:31 g/m3/2H | 85GMAT Toxicometric Parameters of Industrial Toxic Chemicals Under Single Exposure Izmerov, N.F., et al.,Moscow, USSR.: Centre of International Projects, GKNT,1982,36. |
Reported in EPA TSCA Inventory.
Hazard Codes: Xi, Xn
Risk Statements: 10-36/37/38-20
R10:Flammable.
R36/37/38:Irritating to eyes, respiratory system and skin.
R20:Harmful by inhalation.
Safety Statements: 26-36-37/39-16
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36:Wear suitable protective clothing.
S37/39:Wear suitable gloves and eye/face protection.
S16:Keep away from sources of ignition.
RIDADR: UN 1993 3/PG 3
WGK Germany: 1
RTECS: GU8685000
HazardClass: 3
PackingGroup: III
HS Code: 29035990
Slightly toxic by inhalation. When heated to decomposition it emits toxic vapors of Cl−.
Chlorocyclohexane (CAS NO.542-18-7) is also named as 4-05-00-00048 (Beilstein Handbook Reference) ; AI3-23841 ; BRN 1900796 ; Cyclohexyl chloride ; HSDB 2801 ; Monochlorocyclohexane ; NSC 8434 ; Cyclohexane, chloro- . Chlorocyclohexane (CAS NO.542-18-7) is clear liquid.
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