16523-54-9

Basic information

• Product Name: Dicyclohexylchlorophosphine
• Synonyms: Chlorodicyclohexylphosphine 97%;Chlorodicyclohexylphosphine Synonyms Dicyclohexylchlorophosphine;Dicyclohexylphosphine chloride;CHLORODICYCLOHEXYLPHOSPHINE;DICYCLOHEXYLPHOSPHINOUS CHLORIDE;DICYCLOHEXYLCHLOROPHOSPHINE;Dicyclohexylchlorophosphine,min.98%;Dicyclohexylchlorophosphine, 98+%
• CAS NO: 16523-54-9
• Molecular Formula: C₁₂H₂₂ClP
• Molecular Weight: 232.73
• Product Categories: Achiral Phosphine;Alkyl Phosphine;P-Cl;Chlorophosphines;Phosphines;Catalysis and Inorganic Chemistry;Phosphorus Compounds;Phosphorus Precursors;organophosphine halide
• Mol File: 16523-54-9.mol
• Article Data: 11

Chemical Properties

• Melting Point: 126-128 °C
• Boiling Point: 165 °C12 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: Colorless to pale yellow/Liquid
• Density: 1.054 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.00238mmHg at 25°C
• Refractive Index: n20/D 1.533(lit.)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Water Solubility: reacts violently
• Sensitive: Air & Moisture Sensitive
• CAS DataBase Reference: Dicyclohexylchlorophosphine(CAS DataBase Reference)
• NIST Chemistry Reference: Dicyclohexylchlorophosphine(16523-54-9)
• EPA Substance Registry System: Dicyclohexylchlorophosphine(16523-54-9)

Safety Data

• Hazard Codes: C
• Statements: 14-34
• Safety Statements: 26-27-36/37/39-45-8
• RIDADR: UN 3265 8/PG 2
• WGK Germany: 3
• TSCA: No
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 16523-54-9(Hazardous Substances Data)

Usage

Chemical Properties

clear colorless liquid

Uses

Different sources of media describe the Uses of 16523-54-9 differently. You can refer to the following data:
1. Dicyclohexylchlorophosphine is used as pharmaceutical intermediate. It is also used in the synthesis of various phosphines.
2. Chlorodicyclohexylphosphine can be used as a reactant in the synthesis of: 1,2-Bis(dicyclohexylphosphinoxy)ethane ligand by reacting with ethylene glycol in the presence of triethylamine via Michaelis?Arbuzov type rearrangements.1,1,2,2-tetracyclohexyldiphosphine monosulfide ligand by treating with LiS.It can be also used as a starting material for the preparation of some other ligands such as dicyclohexylphosphine oxide , phosphino substituted N-aryl pyrroles , di-tert-butyl((dicyclohexylphosphino)methyl)phosphine , dicyclohexylcyclopentylphosphine. These ligands are used in Pd-catalyzed cross-coupling reactions.

Application

Chlorodicyclohexylphosphine can be used as a reactant in the synthesis of:1,2-Bis(dicyclohexylphosphinoxy)ethane ligand by reacting with ethylene glycol in the presence of triethylamine via Michaelis?Arbuzov type rearrangements.1,1,2,2-tetracyclohexyldiphosphine monosulfide ligand by treating with LiS.It can be also used as a starting material for the preparation of some other ligands such as dicyclohexylphosphine oxide , phosphino substituted N-aryl pyrroles , di-tert-butyl((dicyclohexylphosphino)methyl)phosphine , dicyclohexylcyclopentylphosphine. These ligands are used in Pd-catalyzed cross-coupling reactions.

Precautions

Store in cool, dry conditions in well sealed containers. Protect from humidity and water. Store under dry inert gas. It is sensitive to air and moisture. Incompatible with strong oxidizing agents.

InChI:InChI=1/C12H22ClP/c13-14(11-7-3-1-4-8-11)12-9-5-2-6-10-12/h11-12H,1-10H2

Synthetic route

dicyclohexylphosphane (829-84-5) → chlorodicyclohexylphosphane (16523-54-9)

Conditions	Yield
With Ethyl trichloroacetate In chlorobenzene at 80℃; for 2.46667h; Product distribution / selectivity;	80.6%

cyclohexylmagnesiumchloride (931-51-1) → chlorodicyclohexylphosphane (16523-54-9)

Conditions	Yield
With phosphorus trichloride
With phosphorus trichloride In diethyl ether
With phosphorus trichloride In toluene at 0℃;

cyclohexylmagnesiumchloride (931-51-1) + dichlorocyclohexylphosphine (2844-89-5) → chlorodicyclohexylphosphane (16523-54-9)

cyclohexane (110-82-7) + dichlorocyclohexylphosphine (2844-89-5) → chlorodicyclohexylphosphane (16523-54-9)

Conditions	Yield
Irradiation;

(chloroacetyl)dicyclohexylphosphane → chlorodicyclohexylphosphane (16523-54-9)

Conditions	Yield
In chloroform at 20℃;

(dichloroacetyl)dicyclohexylphosphane → chlorodicyclohexylphosphane (16523-54-9)

Conditions	Yield
In chloroform at 20℃;

(trichloroacetyl)dicyclohexylphosphane → chlorodicyclohexylphosphane (16523-54-9)

Conditions	Yield
In chloroform at 20℃;

1-bromocyclohexane (108-85-0) → chlorodicyclohexylphosphane (16523-54-9)

Conditions	Yield
Stage #1: 1-bromocyclohexane With magnesium In tetrahydrofuran at 20℃; for 2h; Grignard reaction; Stage #2: With diethylphosphoramidous dichloride In tetrahydrofuran at 0 - 50℃; for 3h; phosphorylation; Stage #3: With hydrogenchloride In pentane at 0℃; for 1h; Hydrolysis;

cyclohexyl chloride (542-18-7) → chlorodicyclohexylphosphane (16523-54-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: Mg / diethyl ether / 2.5 h / Heating 2: PCl3 / diethyl ether View Scheme
Stage #1: cyclohexyl chloride With magnesium In diethyl ether Stage #2: With phosphorus trichloride In diethyl ether at -40 - 20℃; for 5.33333h;
Multi-step reaction with 2 steps 1: diethyl ether 2: phosphorus trichloride / diethyl ether / -40 - 20 °C View Scheme
Stage #1: cyclohexyl chloride With magnesium In diethyl ether Stage #2: With phosphorus trichloride In tetrahydrofuran; diethyl ether at -40 - 20℃; for 7h;
Multi-step reaction with 2 steps 1: magnesium / diethyl ether 2: phosphorus trichloride / tetrahydrofuran / 7 h / -40 - 20 °C View Scheme

trimethylsilyldicyclohexylphosphane (104202-80-4) → chlorodicyclohexylphosphane (16523-54-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: 100 percent / diethyl ether / -25 °C 2: CHCl3 / 20 °C View Scheme
Multi-step reaction with 2 steps 1: 100 percent / diethyl ether / -25 °C 2: CHCl3 / 20 °C View Scheme
Multi-step reaction with 2 steps 1: 100 percent / diethyl ether / -25 °C 2: CHCl3 / 20 °C View Scheme

Chlor-diethylamino-cyclohexyl-phosphan (70530-88-0) → chlorodicyclohexylphosphane (16523-54-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: HCl View Scheme

cyclohexane (110-82-7) + deuterium → chlorodicyclohexylphosphane (16523-54-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: PCl3 / Irradiation 2: Irradiation View Scheme

1-phenylpyrrole (635-90-5) + chlorodicyclohexylphosphane (16523-54-9) → N–phenyl–2–(dicyclohexylphosphino)pyrrole

Conditions	Yield
Stage #1: 1-phenylpyrrole With n-butyllithium; N,N,N,N,-tetramethylethylenediamine In hexane Inert atmosphere; Reflux; Stage #2: chlorodicyclohexylphosphane In hexane for 1h; Reflux;	99%
Stage #1: 1-phenylpyrrole With n-butyllithium; N,N,N,N,-tetramethylethylenediamine Stage #2: chlorodicyclohexylphosphane

2-chloro-N,N-diisopropylbenzamide (70657-63-5) + chlorodicyclohexylphosphane (16523-54-9) → N,N-diisopropyl 6-chloro-2-dicyclohexylphosphinobenzamide (1053223-43-0)

Conditions	Yield
Stage #1: N,N-diisopropyl 2-chlorobenzamide With n-butyllithium; N,N,N,N,-tetramethylethylenediamine In tetrahydrofuran; hexane at -78℃; for 0.583333h; Inert atmosphere; Stage #2: chlorodicyclohexylphosphane In tetrahydrofuran; hexane at -78 - 20℃; Inert atmosphere;	99%

(R)-(-)-N-benzyl-4-hydroxymethyl-3-azahexan-1-ol (352655-19-7) + chlorodicyclohexylphosphane (16523-54-9) → (2R)-2-[benzyl{(2-((dicyclohexylphosphanyl)oxy)ethyl)}amino]butyldicyclohexylphosphinite (1305343-45-6)

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃; Inert atmosphere;	99%

2,6-Diaminopyridine (141-86-6) + chlorodicyclohexylphosphane (16523-54-9) → N,N'-bis(dicyclohexyl)-2,6-diaminopyridine

Conditions	Yield
With triethylamine In toluene at 70℃; for 48h;	99%

1-(2,4-dimethoxyphenyl)naphthalene + chlorodicyclohexylphosphane (16523-54-9) → dicyclohexyl(2,6-dimethoxy-3-(naphthalen-1-yl)phenyl)phosphane

Conditions	Yield
Stage #1: 1-(2,4-dimethoxyphenyl)naphthalene With n-butyllithium In tetrahydrofuran; hexane for 1.25h; Cooling with ice; Stage #2: chlorodicyclohexylphosphane In tetrahydrofuran; hexane at 20℃; for 3.66667h; Cooling with ice;	99%

ethylene glycol (107-21-1) + chlorodicyclohexylphosphane (16523-54-9) → 1,2-bis(dicyclohexylphosphinite)ethane

Conditions	Yield
With triethylamine In tetrahydrofuran at 0 - 20℃; for 74h;	98.7%

1,2-bis(3-hydroxyprop-1-yn-1-yl)benzene (116510-02-2) + chlorodicyclohexylphosphane (16523-54-9) → 3,8-bis(dicyclohexylphosphinyl)-1,2-dihydrocyclobuta[b]naphthalene

Conditions	Yield
With triethylamine In tetrahydrofuran at -78 - 20℃; for 4h;	98%
With triethylamine In tetrahydrofuran at 20℃; for 2h;	98%

sodium tetrafluoroborate (13755-29-8) + C28H46P(1+)*I(1-) + chlorodicyclohexylphosphane (16523-54-9) → C40H67P2(1+)*BF4(1-)

Conditions	Yield
Stage #1: C28H46P(1+)*I(1-); chlorodicyclohexylphosphane With n-butyllithium In hexane; toluene at 20℃; for 72h; Inert atmosphere; Schlenk technique; Stage #2: sodium tetrafluoroborate In acetonitrile at 20℃; Inert atmosphere; Schlenk technique;	98%

2,2'-dihydroxybiphenyl (1806-29-7) + chlorodicyclohexylphosphane (16523-54-9) → (C6H4OP(cyclohexyl)2)2 (872217-45-3)

Conditions	Yield
With triethylamine In acetonitrile at 60℃;	97%

1-(2,6-diisopropylphenyl)-1H-imidazole (25364-47-0) + chlorodicyclohexylphosphane (16523-54-9) → 2-(dicyclohexylphosphino)-1-(2,6-diisopropylphenyl)-1H-imidazole (1138156-50-9)

Conditions	Yield
Stage #1: 1-(2,6-diisopropylphenyl)-1H-imidazole With n-butyllithium In tetrahydrofuran; hexane at -30℃; for 0.5h; Inert atmosphere; Stage #2: chlorodicyclohexylphosphane In tetrahydrofuran; hexane at -30 - 50℃; Inert atmosphere;	97%
Stage #1: 1-(2,6-diisopropylphenyl)-1H-imidazole With n-butyllithium In tetrahydrofuran; hexane at 30℃; for 0.5h; Glovebox; Inert atmosphere; Stage #2: chlorodicyclohexylphosphane In tetrahydrofuran; hexane at 50℃; for 1h; Glovebox; Inert atmosphere;	44%

C19H17N5 + chlorodicyclohexylphosphane (16523-54-9) → C31H38N5P

Conditions	Yield
Stage #1: C19H17N5 With n-butyllithium In tetrahydrofuran at -80 - 0℃; for 1h; Inert atmosphere; Stage #2: chlorodicyclohexylphosphane at -80 - 20℃; Inert atmosphere;	96.1%

C19H17N5 + chlorodicyclohexylphosphane (16523-54-9) → C31H38N5P

Conditions	Yield
Stage #1: C19H17N5 With n-butyllithium In tetrahydrofuran; ethanol at -80 - 0℃; for 1h; Inert atmosphere; Stage #2: chlorodicyclohexylphosphane In tetrahydrofuran; ethanol at -80 - 20℃; Inert atmosphere;	96.1%

(R)-[(α-(dimethylamino)ethyl)-η(6)-benzene]chromium tricarbonyl + chlorodicyclohexylphosphane (16523-54-9) → [η6-(R,R)-((NMe2)CHMe)C6H4PCy2]Cr(CO)3

Conditions

Yield

With t-BuLi In diethyl ether byproducts: LiCl; under N2; to a stirred soln. of Cr-contg. compd. (8.77 mmol) in dry Et2O, t-BuLi (10.53 mmol, in hexane) was added dropwise for 1 h at -80°C; the mixt. was stirred for 1 h; the lithiated complex was dissolved in THF; ClPCy2 (10.53 mmol) was added; after warming to room temp., LiCl was filtered off and the solvent was removed in vac.; column chromy. on alumina (eluent: pentane, Et2O); elem.anal.;

96%

1,3-Dimethoxybenzene (151-10-0) + chlorodicyclohexylphosphane (16523-54-9) → dicyclohexyl(2',6'-dimethoxy-[1,1'-biphenyl]-2-yl)phosphine (1070663-82-9)

Conditions	Yield
Stage #1: 1,3-Dimethoxybenzene With n-butyllithium In tetrahydrofuran at 20℃; for 5h; Stage #2: chlorodicyclohexylphosphane In tetrahydrofuran at 20℃; for 12h;	96%
Stage #1: 1,3-Dimethoxybenzene With n-butyllithium In tetrahydrofuran; hexanes at 0 - 20℃; for 5.17h; Inert atmosphere; Stage #2: chlorodicyclohexylphosphane In tetrahydrofuran at 0 - 20℃; for 12.17h; Inert atmosphere;	96%

4,5-dihydro-4,4-dimethyl-2-phenoxazole (19312-06-2) + chlorodicyclohexylphosphane (16523-54-9) → 2-[2-(dicyclohexylphosphino)phenyl]-4,5-dihydro-4,4-dimethyloxazole (226088-99-9)

Conditions	Yield
Stage #1: 4,5-dihydro-4,4-dimethyl-2-phenoxazole With N,N,N,N,-tetramethylethylenediamine; sec.-butyllithium In cyclohexane; pentane at -78 - 20℃; Inert atmosphere; Stage #2: chlorodicyclohexylphosphane In cyclohexane; pentane at -78 - 20℃; Inert atmosphere;	96%

2'-bromo-6-methoxy-N,N-dimethylbiphenyl-2-amine (1160556-60-4) + chlorodicyclohexylphosphane (16523-54-9) → 2'-(dicyclohexylphosphino)-6-methoxy-N,N-dimethylbiphenyl-2-amine (1160556-61-5)

Conditions	Yield
Stage #1: 2'-bromo-6-methoxy-N,N-dimethylbiphenyl-2-amine With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.75h; Inert atmosphere; Stage #2: chlorodicyclohexylphosphane In tetrahydrofuran; hexane at -78 - 20℃;	96%

ferrocene (102-54-5) + chlorodicyclohexylphosphane (16523-54-9) → 1-di(2-(5-methylfuryl)phosphanyl)ferrocene (525603-48-9)

Conditions	Yield
With aluminum (III) chloride In hexane at -10℃; for 3h; Temperature; Inert atmosphere;	96%

recorcinol (108-46-3) + chlorodicyclohexylphosphane (16523-54-9) → C30H48O2P2

Conditions	Yield
With triethylamine In tetrahydrofuran at 85℃; for 20h; Inert atmosphere;	96%

2-Aminomethylthiophene (27757-85-3) + chlorodicyclohexylphosphane (16523-54-9) → thiophene-2-(N-dicyclohexylphosphino)methylamine (1588499-13-1)

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃; for 1.25h; Inert atmosphere; Schlenk technique;	95.6%

1-chloro-3-(3-methylimidazolidin-1-yl)propan-2-ol chloride (1118072-24-4) + chlorodicyclohexylphosphane (16523-54-9) → 1-{3-chloro-2-[(dicyclohexylphosphanyl)oxy]propyl}-3-methylimidazolium chloride (1621393-73-4)

Conditions	Yield
Stage #1: 1-chloro-3-(3-methylimidazolidin-1-yl)propan-2-ol chloride With n-butyllithium In hexane; dichloromethane at -78 - 20℃; for 1.5h; Inert atmosphere; Schlenk technique; Stage #2: chlorodicyclohexylphosphane In hexane; dichloromethane at -78 - 20℃; for 4h; Inert atmosphere; Schlenk technique;	95.5%
Stage #1: 1-chloro-3-(3-methylimidazolidin-1-yl)propan-2-ol chloride With n-butyllithium In hexane; dichloromethane at -78 - 20℃; for 1.5h; Inert atmosphere; Stage #2: chlorodicyclohexylphosphane In hexane; dichloromethane at -78 - 20℃; for 2h; Inert atmosphere;	95.5%
Stage #1: 1-chloro-3-(3-methylimidazolidin-1-yl)propan-2-ol chloride With n-butyllithium In hexane; dichloromethane; acetone at -78 - 20℃; for 1.5h; Inert atmosphere; Stage #2: chlorodicyclohexylphosphane In hexane; dichloromethane; acetone at -78 - 20℃; for 2h; Inert atmosphere;	95.5%
Stage #1: 1-chloro-3-(3-methylimidazolidin-1-yl)propan-2-ol chloride With n-butyllithium In dichloromethane at -78 - 20℃; for 1.5h; Inert atmosphere; Schlenk technique; Stage #2: chlorodicyclohexylphosphane In dichloromethane at -78 - 20℃; for 2h; Inert atmosphere; Schlenk technique;	94.8%

(S)-1-Pyrrolidin-2-yl-methanol (23356-96-9) + chlorodicyclohexylphosphane (16523-54-9) → (CH2)3NP(C6H11)2CHCH2OP(C6H11)2 (112150-34-2)

Conditions	Yield
With triethylamine In benzene at 20℃;	95%

chlorodicyclohexylphosphane (16523-54-9) → dicyclohexylphosphine oxide (14717-29-4)

Conditions	Yield
With water In tetrahydrofuran at 20℃; for 2h; Inert atmosphere;	95%
With water In tetrahydrofuran at 20℃; for 5h;	86%
With water Ambient temperature;
Multi-step reaction with 2 steps 1: (i) nBuLi, benzene, hexane, (ii) /BRN= 956672/ 2: H2O / CHCl3 View Scheme
With hydrogenchloride In water at 0 - 20℃; for 24h;

(RC,SFc,SP)-1-[2-(1-dimethylaminoethyl)ferrocen-1-yl]phenylphosphino-1'-bromoferrocene + chlorodicyclohexylphosphane (16523-54-9) → (RC,SFc,SP)-1-[2-(1-N,N-dimethylaminoethyl)ferrocen-1-yl]phenylphosphino-1'-dicyclohexylphosphinoferrocene

Conditions	Yield
Stage #1: (RC,SFc,SP)-1-[2-(1-dimethylaminoethyl)ferrocen-1-yl]phenylphosphino-1'-bromoferrocene With sec.-butyllithium In tert-butyl methyl ether; cyclohexane at 0℃; for 1h; Stage #2: chlorodicyclohexylphosphane In tert-butyl methyl ether; cyclohexane at 0 - 20℃; for 2h;	95%
Stage #1: (RC,SFc,SP)-1-[2-(1-dimethylaminoethyl)ferrocen-1-yl]phenylphosphino-1'-bromoferrocene With n-butyllithium In hexane; tert-butyl methyl ether at -5 - 0℃; Stage #2: chlorodicyclohexylphosphane In hexane; tert-butyl methyl ether at 0 - 20℃;	95%

C30H31BrFe2NP + chlorodicyclohexylphosphane (16523-54-9) → (RC,SFC,SP)-1-[2-(1-dimethylaminoethyl)ferrocen-1-yl]phenylphosphino-1'-dicyclohexylphosphinoferrocene

Conditions	Yield
Stage #1: C30H31BrFe2NP With sec.-butyllithium In methyl tert-butyl ether (MTBE); cyclohexane at 0℃; for 1h; Stage #2: chlorodicyclohexylphosphane In tert-butyl methyl ether; cyclohexane at 0 - 20℃; for 2h;	95%

3-chloro-N,N-diisopropylbenzamide (35306-66-2) + chlorodicyclohexylphosphane (16523-54-9) → N,N-diisopropyl 3-chloro-2-dicyclohexylphosphinobenzamide (1053223-45-2)

Conditions	Yield
Stage #1: N,N-diisopropyl 3-chlorobenzamide With n-butyllithium; N,N,N,N,-tetramethylethylenediamine In tetrahydrofuran; hexane at -78℃; for 0.583333h; Inert atmosphere; Stage #2: chlorodicyclohexylphosphane In tetrahydrofuran; hexane at -78 - 20℃; Inert atmosphere;	95%

9-dicyclohexylphosphino-9H-fluorene + chlorodicyclohexylphosphane (16523-54-9) → C37H52P2

Conditions	Yield
Stage #1: 9-dicyclohexylphosphino-9H-fluorene With n-butyllithium In tetrahydrofuran at 0℃; for 0.5h; Inert atmosphere; Schlenk technique; Stage #2: chlorodicyclohexylphosphane In tetrahydrofuran at 0 - 20℃; for 18h; Inert atmosphere; Schlenk technique;	95%

(1R,2R)-N',N'-dimethyl-1,2-diphenylethane-1,2-diamine (320778-96-9) + chlorodicyclohexylphosphane (16523-54-9) → (1R,2R)-N1-(dicyclohexylphosphino)-N2,N2-dimethyl-1,2-diphenylethane-1,2-diamine

Conditions	Yield
Stage #1: (1R,2R)-N1,N1-dimethyl-1,2-diphenylethane-1,2-diamine With n-butyllithium In tetrahydrofuran; hexane at -78 - 0℃; for 1h; Inert atmosphere; Stage #2: chlorodicyclohexylphosphane In tetrahydrofuran; hexane at -78 - 0℃; for 1h; Inert atmosphere;	94.4%

8-quinolinol (148-24-3) + bis(benzonitrile)palladium(II) dichloride (15617-18-2, 39958-10-6, 14220-64-5) + chlorodicyclohexylphosphane (16523-54-9) → [Pd(C9H6N(O)P(C6H11)2)Cl2] (1219698-46-0)

Conditions	Yield
With potassium hydride In tetrahydrofuran; dichloromethane quinoline was dissolved in THF, KH was added slowly, mixt. was stirred for 10 min, filtered, (C3H7)2PCl in THF was added dropwise, mixt. was stirred for 1 h, soln. of Pd complex in CH2Cl2 was added to filtrate, mixt.was stirred overnight; mixt. was filtered through celite, volatiles were removed under vac.; elem. anal.;	94%

2-bromo-pyridine (109-04-6) + chlorodicyclohexylphosphane (16523-54-9) → 2-(dicyclohexylphosphino)pyridine (959264-38-1)

Conditions	Yield
Stage #1: 2-bromo-pyridine With n-butyllithium In diethyl ether; hexane at -100 - -90℃; for 2h; Stage #2: chlorodicyclohexylphosphane In diethyl ether; hexane at -90℃; for 2h;	94%

lithium cyclopentadienide + chlorodicyclohexylphosphane (16523-54-9) → lithium (dicyclohexylphosphino)cyclopentadienide

Conditions	Yield
Stage #1: lithium cyclopentadienide; chlorodicyclohexylphosphane In toluene at -80 - 20℃; Inert atmosphere; Stage #2: With n-butyllithium In hexane; n-heptane at -40 - 20℃; Inert atmosphere;	94%

Upstream product

• 931-51-1 cyclohexylmagnesiumchloride 
• 2844-89-5 dichlorocyclohexylphosphine 
• 110-82-7 cyclohexane 
• 70530-88-0 Chlor-diethylamino-cyclohexyl-phosphan 
• 829-84-5 dicyclohexylphosphane 
• 104202-80-4 trimethylsilyldicyclohexylphosphane 
• 108-85-0 1-bromocyclohexane 
• 542-18-7 cyclohexyl chloride 

Downstream Products

• 65796-69-2 Dicyclohexyl-isopropyloxy-phosphin 
• 70575-32-5 C₃₇H₄₃P₃ 
• 41839-40-1 1.1-Dibutoxy-2.2-dicyclohexyldiphosphin 
• 27298-56-2 [1-(Dicyclohexyl-phosphinoyl)-3-methyl-buta-1,2-dienyl]-benzene 
• 14185-94-5 keYPhos 
• 66193-25-7 C₂₄H₄₄OP₂ 
• 59891-99-5 1-(p-Dicyclohexyl-phosphinophenyl)-1-methoxyaethan 
• 46392-44-3 Ethyl-dicyclohexyl-phosphin 
• 3040-63-9 1,1,2,2-tetraethyldiphosphane 
• 3040-65-1 2.2-Diaethyl-1.1-dicyclohexyl-biphosphin 
• 2359-99-1 tetracyclohexyldiphosphine 
• 3040-61-7 1,1-dicyclohexyl-2,2-diphenyldiphosphane 
• 13411-70-6 Triphenylphosphin-α-dicyclohexylphosphino-aethyliden 
• 829-84-5 dicyclohexylphosphane 

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A new, readily available, and air-stable monophosphine ligand, i.e., Zheda-Phos, has been developed for the general and highly effective palladium-catalyzed monoarylation of acetone with aryl chlorides. The reaction rate is of first-order dependence with the aryl chloride. Copyright

2,6-diisopropoxyphenyl(dicyclohexyl)phosphine: A new ligand for palladium-catalyzed amination reactions of aryl chlorides with potassium hydroxide as the base

A new, readily available monophosphine tetrafluoroborate salt [L2·HBF4] was developed for the palladium-catalyzed amination reaction of aryl chlorides in moderate to high yields with the cheap and easily available potassium hydroxide as the base. The reaction enjoys a wide scope, lower reaction temperatures, shorter reaction times, high yields, and low catalyst loading when compared to some of same amination reactions reported in the literature. Based on a kinetic study, 31P NMR measurements, and DFT calculations, a mechanism involving a 1:1 Pd/L species is proposed.