3042-69-1

Basic information

• Product Name: 1-cyclohexylnaphthalene
• Synonyms: 1-cyclohexylnaphthalene;NSC 131573;Naphthalene, 1-cyclohexyl-;1-CYCLOHEXYLNAPHTALENE
• CAS NO: 3042-69-1
• Molecular Formula: C₁₆H₁₈
• Molecular Weight: 210.31412
• EINECS: 221-247-2
• Product Categories: Aromatics;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 3042-69-1.mol
• Article Data: 31

Chemical Properties

• Melting Point: 31 °C
• Boiling Point: 346.7 °C at 760 mmHg
• Flash Point: 174.2 °C
• Appearance: /
• Density: 1.027 g/cm³
• Vapor Pressure: 0.000113mmHg at 25°C
• Refractive Index: 1.599
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)
• CAS DataBase Reference: 1-cyclohexylnaphthalene(CAS DataBase Reference)
• NIST Chemistry Reference: 1-cyclohexylnaphthalene(3042-69-1)
• EPA Substance Registry System: 1-cyclohexylnaphthalene(3042-69-1)

Safety Data

• Hazardous Substances Data: 3042-69-1(Hazardous Substances Data)

Usage

Chemical Properties

Colourless Oil

Uses

An intermediate in the preparation of Vedaprofen

InChI:InChI=1/C16H18/c1-2-7-13(8-3-1)16-12-6-10-14-9-4-5-11-15(14)16/h4-6,9-13H,1-3,7-8H2

Synthetic route

1-Bromonaphthalene (90-11-9) + cyclohexylmagnesium bromide (931-50-0) → 1-cyclohexylnaphthalene (3042-69-1)

Conditions	Yield
Stage #1: cyclohexylmagnesium bromide With zinc(II) chloride In tetrahydrofuran at 20℃; for 1h; Stage #2: 1-Bromonaphthalene; dichloro bis(acetonitrile) palladium(II) In toluene at 60℃; for 3h; Negishi coupling; Further stages.;	85%
nickel

1-bromocyclohexane (108-85-0) + 1-Bromonaphthalene (90-11-9) → 1-cyclohexylnaphthalene (3042-69-1) + 1,1'-bisnaphthalene (604-53-5)

Conditions	Yield
With N,N,N′,N′-tetramethylcyclohexane-1,2-diamine; magnesium; cobalt(II) chloride In tetrahydrofuran at 0℃; Inert atmosphere;	A 85% B n/a

1-bromocyclohexane (108-85-0) + 1-naphthylmagnesiumbromide (703-55-9) → 1-cyclohexylnaphthalene (3042-69-1) + 1,1'-bisnaphthalene (604-53-5)

Conditions	Yield
With FeCl2(N(C2H5)2CH2CH2NC(CH3)CHC(CH3)O) In diethyl ether at 20℃; for 0.0833333h; Inert atmosphere;	A 85% B n/a

1-Bromonaphthalene (90-11-9) + cyclohexylmagnesiumchloride (931-51-1) → 1-cyclohexylnaphthalene (3042-69-1)

Conditions	Yield
With [polymer-incarcerated nickel nanocatalyst] PICB-NHC-Ni (0.25 mol % as Ni) In tetrahydrofuran at 20℃; for 12h;	84%

cyclohexylmagnesium bromide (931-50-0) + 1-Chloronaphthalene (90-13-1) → 1-cyclohexylnaphthalene (3042-69-1)

Conditions	Yield
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: 1-Chloronaphthalene With iron(III)-acetylacetonate In tetrahydrofuran at 25℃; for 0.0833333h; Kumada Cross-Coupling; Inert atmosphere; Flow reactor; Irradiation;	83%

1-naphthyl N,N-diethylcarbamate (85630-39-3) + cyclohexylmagnesiumchloride (931-51-1) → 1-cyclohexylnaphthalene (3042-69-1)

Conditions	Yield
With 1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazolium chloride; iron(II) chloride In tetrahydrofuran; dichloromethane at 65℃; for 3h; Inert atmosphere; Sealed tube;	82%

1-naphthyl tosylate (68211-49-4) + cyclohexylmagnesium bromide (931-50-0) → 1-cyclohexylnaphthalene (3042-69-1)

Conditions	Yield
With 1,2-bis(diphenylphosphino)ethane nickel(II) chloride In tetrahydrofuran at 23℃; Kumada Cross-Coupling; Inert atmosphere; Schlenk technique;	82%

naphthalen-1-yl N,N-dimethylsulfamate (1144-13-4) + cyclohexylmagnesiumchloride (931-51-1) → 1-cyclohexylnaphthalene (3042-69-1)

Conditions	Yield
With 1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazolium chloride; iron(II) chloride In tetrahydrofuran; dichloromethane at 65℃; for 3h; Inert atmosphere; Sealed tube;	80%

1-naphthyl tosylate (68211-49-4) + cyclohexylmagnesiumchloride (931-51-1) → 1-cyclohexylnaphthalene (3042-69-1)

Conditions	Yield
With iron(III)-acetylacetonate In tetrahydrofuran; 1-methyl-pyrrolidin-2-one at 0℃; for 1h;	77%
With cobalt (III) fluoride; N,N′-bis(2,6-diisopropylphenyl)imidazol-2-ylidene hydrochloride In tetrahydrofuran at 80℃; for 5h;	25%

dinaphthalen-1-ylzinc (7029-32-5) + Cyclohexanecarboxylic acid (98-89-5) → 1-cyclohexylnaphthalene (3042-69-1)

Conditions

Yield

Stage #1: Cyclohexanecarboxylic acid With triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In tetrahydrofuran at 20℃; for 2h; Sealed tube; Inert atmosphere; Stage #2: With iron(III)-acetylacetonate; o-phenylenebis(diphenylphosphine) In tetrahydrofuran at 20℃; for 0.0833333h; Negishi Coupling; Sealed tube; Inert atmosphere; Stage #3: dinaphthalen-1-ylzinc In tetrahydrofuran at 20℃; for 1h; Catalytic behavior; Reagent/catalyst; Temperature; Negishi Coupling; Sealed tube; Inert atmosphere;

76%

1-Iodonaphthalene (90-14-2) + 1-cyclohexyl-2,4,6-triphenylpyridin-1-ium tetrafluoroborate salt → 1-cyclohexylnaphthalene (3042-69-1)

Conditions	Yield
With manganese; (1,2-dimethoxyethane)dichloronickel(II) In N,N-dimethyl acetamide	71%

diethyl naphthalen-1-yl phosphate (33650-14-5) + cyclohexylmagnesiumchloride (931-51-1) → 1-cyclohexylnaphthalene (3042-69-1)

Conditions	Yield
With [1,3-bis(2,6-diisopropylphenyl)imidazolium][Fe(PCy3)Br3] In tetrahydrofuran at 0 - 85℃; for 8h; Reagent/catalyst; Inert atmosphere;	70%
With [1,3-bis(2,6-diisopropylphenyl)imidazolium][Fe(PCy3)Br3] In tetrahydrofuran at 0 - 85℃; for 8h; Schlenk technique; Inert atmosphere;	53%

1-bromocyclohexane (108-85-0) + 1-Bromonaphthalene (90-11-9) → 1-cyclohexylnaphthalene (3042-69-1)

Conditions	Yield
With iron(III) chloride; N,N,N,N,-tetramethylethylenediamine In tetrahydrofuran at 0℃; for 3h; Inert atmosphere;	67%

1-naphthyl tosylate (68211-49-4) + C18H19O4Si(1-)*H(1+) → 1-cyclohexylnaphthalene (3042-69-1)

Conditions	Yield
With tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate; (1,2-dimethoxyethane)dichloronickel(II); 4,4'-di-tert-butyl-2,2'-bipyridine In N,N-dimethyl-formamide at 27℃; for 24h; Inert atmosphere; Irradiation; Schlenk technique;	63%

1-bromocyclohexane (108-85-0) + 1-naphthyl diethylphosphate → 1-cyclohexylnaphthalene (3042-69-1)

Conditions	Yield
With 1,3-dibutyl-1H-benzo[d]imidazol-3-ium bromide; C33H27N2(1+)*Br4Fe(1-); magnesium In tetrahydrofuran at 0 - 35℃; for 14h; Inert atmosphere; Schlenk technique;	62%

dinaphthalen-1-ylzinc (7029-32-5) + 1,3-dioxoisoindolin-2-yl cyclohexanecarboxylate → 1-cyclohexylnaphthalene (3042-69-1)

Conditions	Yield
With iron(III)-acetylacetonate; o-phenylenebis(diphenylphosphine) In tetrahydrofuran at 0 - 25℃; for 1h; Negishi Coupling; Inert atmosphere;	60%
Stage #1: 1,3-dioxoisoindolin-2-yl cyclohexanecarboxylate With iron(III)-acetylacetonate; o-phenylenebis(diphenylphosphine) In tetrahydrofuran for 0.0833333h; Negishi Coupling; Sealed tube; Inert atmosphere; Stage #2: dinaphthalen-1-ylzinc In tetrahydrofuran at 20℃; for 1h; Negishi Coupling; Sealed tube; Inert atmosphere;	64 %Spectr.

1-naphthylmagnesiumbromide (703-55-9) + 1,3-dioxoisoindolin-2-yl cyclohexanecarboxylate → 1-cyclohexylnaphthalene (3042-69-1)

Conditions	Yield
Stage #1: 1,3-dioxoisoindolin-2-yl cyclohexanecarboxylate With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; iron(III)-acetylacetonate In tetrahydrofuran at 25℃; for 0.0833333h; Kumada Cross-Coupling; Inert atmosphere; Stage #2: 1-naphthylmagnesiumbromide With lithium chloride In tetrahydrofuran at 0 - 25℃; for 1h; Kumada Cross-Coupling;	57%

1-bromocyclohexane (108-85-0) + diethyl naphthalen-1-yl phosphate (33650-14-5) → 1-cyclohexylnaphthalene (3042-69-1)

Conditions	Yield
With [1,3-bis(2,6-diisopropylphenyl)imidazolium][Fe(PCy3)Br3]; magnesium; lithium chloride In tetrahydrofuran at 0 - 25℃; Schlenk technique; Inert atmosphere;	53%

naphthalene (91-20-3) + Cyclohexyl benzenesulphonate (782-84-3) → 1-cyclohexylnaphthalene (3042-69-1) + 2-cyclohexylnaphthalene (42044-07-5)

1-cyclohex-1-enyl-naphthalene (40358-51-8) → 1-cyclohexylnaphthalene (3042-69-1)

Conditions	Yield
With acetic acid; platinum Hydrogenation;
With ethanol; nickel

4-cyclohexyl-1,2-dihydronaphthalene (306993-45-3) → 1-cyclohexylnaphthalene (3042-69-1)

Conditions	Yield
With platinum at 300 - 320℃;
With selenium at 300 - 320℃;

naphthalene (91-20-3) + cyclohexanol (108-93-0) → 1-cyclohexylnaphthalene (3042-69-1)

Conditions	Yield
With boron trifluoride

1-bromocyclohexane (108-85-0) + naphthalene (91-20-3) → 1-cyclohexylnaphthalene (3042-69-1) + 2-cyclohexylnaphthalene (42044-07-5) + 2,6-Dicyclohexylnaphthalene (42044-10-0) + 2,7-Dicyclohexylnaphthalene (136288-21-6)

Conditions	Yield
zeolite HY2.5 at 82℃; for 6h; Product distribution; Mechanism; other catalysts, other temperature, other alkylating agent;
zeolite HY2.5 at 200℃; for 0.166667h; Yield given. Yields of byproduct given;
With NH4-USY760 In decane at 175℃; for 2h; Product distribution; Further Variations:; Reagents; Alkylation;

tetrahydro(8,9,10,11)benzo(b)naphto<1,2-d>thiophene (18428-06-3) → 1-cyclohex-1-enyl-naphthalene (40358-51-8) + 1-cyclohexylnaphthalene (3042-69-1) + cyclohexyl-5 tetraline (90501-15-8) + decahydro(1,2,3,4,7a,8,9,10,11,11a)benzo(b)naphto<1,2-d>thiophene (90501-18-1) + hexahydro(7a,8,9,10,11,11a)benzo(b)naphto<1,2-d>thiophene (90501-17-0)

Conditions	Yield
With hydrogen; aluminum oxide; nickel molybdenum In dodecane at 250℃; under 30400 Torr; Product distribution;

1-(naphthalen-1-yl)cyclohexanol (74685-85-1) → 1-cyclohexylnaphthalene (3042-69-1)

Conditions	Yield
With hydrogen; palladium on activated charcoal

naphthalene (91-20-3) + cyclohexene (110-83-8) → 1-cyclohexylnaphthalene (3042-69-1) + 2-cyclohexylnaphthalene (42044-07-5) + 2,6-Dicyclohexylnaphthalene (42044-10-0) + 2,7-Dicyclohexylnaphthalene (136288-21-6)

Conditions	Yield
zeolite HY2.5 at 200℃; for 0.416667h; Yield given. Yields of byproduct given;

α-<Δ3-cyclohexenyl>-naphthalin (133131-79-0) → 1-cyclohexylnaphthalene (3042-69-1)

Conditions	Yield
With selenium at 300 - 320℃;

naphthalene (91-20-3) + cyclohexyl mesylate (16156-56-2) → 1-cyclohexylnaphthalene (3042-69-1) + 2-cyclohexylnaphthalene (42044-07-5)

Conditions	Yield
With scandium tris(trifluoromethanesulfonate) In tetrachloromethane at 80℃; for 4h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
scandium tris(trifluoromethanesulfonate) In 1,2-dichloro-ethane at 80℃; for 4h; Product distribution; also in the presence of TfOH;
scandium tris(trifluoromethanesulfonate) In 1,2-dichloro-ethane at 80℃; for 4h; Yield given; Yields of byproduct given. Title compound not separated from byproducts;

(+-)-1-cyclohexyl-1,2,3,4-tetrahydro-naphthalene → 1-cyclohexylnaphthalene (3042-69-1)

Conditions	Yield
With palladium on activated charcoal at 250℃;

1-cyclohexylnaphthalene (3042-69-1) → 1-bromo-4-cyclohexyl-naphthalene (51670-90-7)

Conditions	Yield
With bromine In carbon disulfide

Upstream product

• 18428-06-3 tetrahydro(8,9,10,11)benzo(b)naphto<1,2-d>thiophene 
• 74685-85-1 1-(naphthalen-1-yl)cyclohexanol 
• 108-85-0 1-bromocyclohexane 
• 91-20-3 naphthalene 
• 90-11-9 1-Bromonaphthalene 
• 931-50-0 cyclohexylmagnesium bromide 
• 306993-45-3 4-cyclohexyl-1,2-dihydronaphthalene 
• 40358-51-8 1-cyclohex-1-enyl-naphthalene 
• 782-84-3 Cyclohexyl benzenesulphonate 
• 90-13-1 1-Chloronaphthalene 
• 90-14-2 1-Iodonaphthalene 
• 68211-49-4 1-naphthyl tosylate 
• 931-51-1 cyclohexylmagnesiumchloride 
• 7029-32-5 dinaphthalen-1-ylzinc 

Downstream Products

• 51670-90-7 1-bromo-4-cyclohexyl-naphthalene 
• 71109-04-1 1-chloromethyl-4-cyclohexylnaphthalene 
• 22236-62-0 1-cyclohexyldecaline 

Relevant articles and documents

Reactivity of 1,4-didehydronaphthalene toward organic hydrogen atom donors

1,4-Didehydronaphthalene, generated by thermolysis of 1,2- diethynylbenzene, reacts with organic hydrogen atom donors via hydrogen atom abstraction. The resulting naphthyl radical undergoes the expected abstraction of a hydrogen atom from a second hydrogen atom donor molecule. Surprisingly, significant amounts of radical-radical recombination between the hydrogen donor radical product and the naphthyl radical were also observed for several donors. Further, in some cases, the hydrogen donor radical products also rapidly add to the uncyclized 1,2-diethynylbenzene. (C) 2000 Elsevier Science Ltd.

Visible-Light-Promoted Iron-Catalyzed C(sp2)–C(sp3) Kumada Cross-Coupling in Flow

A continuous-flow, visible-light-promoted method has been developed to overcome the limitations of iron-catalyzed Kumada–Corriu cross-coupling reactions. A variety of strongly electron rich aryl chlorides, previously hardly reactive, could be efficiently coupled with aliphatic Grignard reagents at room temperature in high yields and within a few minutes’ residence time, considerably enhancing the applicability of this iron-catalyzed reaction. The robustness of this protocol was demonstrated on a multigram scale, thus providing the potential for future pharmaceutical application.

Nickel-Catalyzed C(sp2)?C(sp3) Kumada Cross-Coupling of Aryl Tosylates with Alkyl Grignard Reagents

Aryl tosylates are an attractive class of electrophiles for cross-coupling reactions due to ease of synthesis, low price, and the employment of C?O electrophiles, however, the reactivity of aryl tosylates is low. Herein, we report the Ni-catalyzed C(sp2)?C(sp3) Kumada cross-coupling of aryl tosylates with primary and secondary alkyl Grignard reagents. The method delivers valuable alkyl arenes by cross-coupling with challenging alkyl organometallics possessing β-hydrogens that are prone to β-hydride elimination and homo-coupling. The reaction is catalyzed by an air- and moisture stable-Ni(II) precatalyst. A broad range of electronically-varied aryl tosylates, including bis-tosylates, underwent this transformation, and many examples are suitable at mild room temperature conditions. The combination of Ar?X cross-coupling with the facile Ar?OH activation/cross-coupling strategy permits for orthogonal cross-coupling with challenging alkyl organometallics. Furthermore, we demonstrate that the method operates with TON reaching 2000, which is one of the highest turnovers observed to date in Ni-catalyzed cross-couplings. (Figure presented.).