822-68-4

Basic information

• Product Name: CYCLOHEXYLPHOSPHINE
• Synonyms: CYCLOHEXYLPHOSPHINE;Cyclohexylphosphinemincolorlessliq;Cyclohexylphospine;Cyclohexylphosphine,min.97%;Cyclohexylphosphine,min.97%(10wt%inhexane);Cyclohexylphosphine,min.97%(Sure/Sealbottle);CYCLOHEXYLPHOSPINE (10% WT. IN HEXANE);Cyclohexylphosphine, min. 97%
• CAS NO: 822-68-4
• Molecular Formula: C₆H₁₃P
• Molecular Weight: 116.14
• Product Categories: Primary Phosphines;organophosphorus ligand;organophosphine ligand
• Mol File: 822-68-4.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 67-69°C
• Flash Point: -21°C
• Appearance: colorless/liquid
• Density: 0,875 g/cm3
• Vapor Pressure: 6.25mmHg at 25°C
• Sensitive: air sensitive
• Stability: Stability Pyrophoric - spontaneously catches fire in air. Store under an inert atmosphere. Incompatible with organic material, a
• CAS DataBase Reference: CYCLOHEXYLPHOSPHINE(CAS DataBase Reference)
• NIST Chemistry Reference: CYCLOHEXYLPHOSPHINE(822-68-4)
• EPA Substance Registry System: CYCLOHEXYLPHOSPHINE(822-68-4)

Safety Data

• Statements: 17-20/21/22-34
• Safety Statements: 3/7-9-16-26-36/37/39
• RIDADR: 3185
• Hazardous Substances Data: 822-68-4(Hazardous Substances Data)

Usage

Chemical Properties

colourless liquid with an offensive odour

InChI:InChI=1/C6H13P/c7-6-4-2-1-3-5-6/h6H,1-5,7H2

Synthetic route

dicyclohexylphosphonous acid (2310-71-6) → cyclohexylphosphonic acid (1005-23-8) + cyclohexylphosphine (822-68-4)

Conditions	Yield
at 250℃; Yields of byproduct given;	A n/a B 46.13%
With water 1) 250 deg C, 2) reflux; Yield given. Multistep reaction. Yields of byproduct given;

Monoethoxicarbonylcyclohexylphosphan (79564-48-0) → ethanol (64-17-5) + cyclohexylphosphine (822-68-4) + CO2

Conditions	Yield
With hydrogenchloride for 4h; Product distribution; Heating; reaction with KOH;	A n/a B 33% C n/a

cyclohexylphosphonic dichloride (1005-22-7) → cyclohexylphosphine (822-68-4)

Conditions	Yield
With lithium aluminium tetrahydride; diethyl ether
With sodium; toluene

cyclohexene (110-83-8) → cyclohexylphosphine (822-68-4)

Conditions	Yield
With phosphan Irradiation;
With 2,2'-azobis(isobutyronitrile); phosphan at 78 - 80℃; for 3.5h;

cyclohexene (110-83-8) + phosphine → cyclohexylphosphine (822-68-4)

Conditions	Yield
UV-Licht.Irradiation;

Os3(CO)11P(C6H11)H2 (80984-31-2) → cyclohexylphosphine (822-68-4)

Conditions	Yield
In toluene 100°C, 24 h; vac. evapd., chromd. on silica gel with 5/1 pentane/toluene;	60-66

dichlorocyclohexylphosphine (2844-89-5) → cyclohexylphosphine (822-68-4)

Conditions	Yield
Stage #1: dichlorocyclohexylphosphine With sodium In 1,4-dioxane at 110℃; Inert atmosphere; Stage #2: With acetic acid In diethyl ether at -10 - 0℃; for 5h; Inert atmosphere;

diisopropylallylphosphonite (31080-62-3) + cyclohexylphosphine (822-68-4) → C6H11P(C3H6P(OCH(CH3)2)2)2 (850716-19-7)

Conditions	Yield
With 2,2'-azobis(isobutyronitrile) at 20℃; for 48h; Irradiation;	100%

cyclohexylphosphine (822-68-4) + dimethylallylphosphonite → C6H11P(C3H6P(OCH3)2)2 (850716-21-1)

Conditions	Yield
With 2,2'-azobis(isobutyronitrile) at 20℃; for 48h; Irradiation;	100%

1,3-dibromo-propane (109-64-8) + cyclohexylphosphine (822-68-4) → 1,3-bis(cyclohexylphosphanyl)propane (97472-13-4)

Conditions	Yield
Stage #1: cyclohexylphosphine With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.333333h; Inert atmosphere; Stage #2: 1,3-dibromo-propane In tetrahydrofuran; hexane at -78 - 20℃; Inert atmosphere;	100%

cyclohexylphosphine (822-68-4) → C6H14BP

Conditions	Yield
With sodium tetrahydroborate; acetic acid In tetrahydrofuran at 0 - 20℃;	99.5%

2-bromo-pyridine (109-04-6) + cyclohexylphosphine (822-68-4) → cyclohexylbis(2-pyridyl)phosphane (380358-80-5)

Conditions	Yield
With triethylamine; tetrakis(triphenylphosphine) palladium(0) In acetonitrile for 36h; Heating;	98%

formaldehyd (50-00-0) + cyclohexylphosphine (822-68-4) → bis-(hydroxymethyl)cyclohexylphosphine (5958-45-2)

Conditions	Yield
In ethanol; water at 25℃;	98%
In ethanol at 70℃; for 2h; Inert atmosphere;	98%
In hexane; water; acetonitrile at 20℃; for 0.5h; Inert atmosphere;

Mn2(μ-H)(μ-P(cyclo-C6H11)2)(CO)8 + cyclohexylphosphine (822-68-4) → Mn2(μ-H)(μ-P(cyclo-C6H11)2)(CO)7(ax-H2P(cyclo-C6H11)) (316803-49-3)

Conditions	Yield
With Me3NO In tetrahydrofuran metal-complex and H2PCy soln. in THF was cooled to 0 °C in ice-bath, 2 h; chromy. on silica 60, eluent CH2Cl2/hexane=1:1, solvent was removed in high-vac.;	98%

(acetonitrile)(methylcyclopentadienyl)molybdenum tetrachloride + cyclohexylphosphine (822-68-4) → (cyclohexylphosphane)(methylcyclopentadienyl)molybdenium tetrachloride (191542-23-1)

Conditions	Yield
In toluene (argon); stirring (room temp., 2 d); solvent removal (vac.), washing (hexane), filtration, drying (vac.), addn. of toluene, filtration, pptn. with hexane; elem. anal.;	98%

pivalaldehyde (630-19-3) + cyclohexylphosphine (822-68-4) → C11H23OP (1246895-40-8)

Conditions	Yield
With trifluoroacetic acid at 80℃;	97%

titanium tetrachloride (7550-45-0) + cyclohexylphosphine (822-68-4) → (TiCl4(C6H11PH2)2) (469886-23-5, 165281-61-8)

Conditions	Yield
In hexane; toluene under N2 CyPH2 was added to soln. TiCl4 in hexane-toluene; ppt. was filtered, washed with hexane and dried in vacuo; elem. anal.;	96%

2-iodobenzaldehyde (26260-02-6) + cyclohexylphosphine (822-68-4) → C13H18IOP (1246895-38-4)

Conditions	Yield
With trifluoroacetic acid at 80℃;	96%

mu-hydrido-mu-dicyclohexyl-phosphido-octacarbonyl-dirhenium + cyclohexylphosphine (822-68-4) → Re2(μ-H)(μ-P(cyclo-C6H11)2)(CO)7(ax-H2P(cyclo-C6H11)) (316803-45-9)

Conditions	Yield
With Me3NO In tetrahydrofuran metal-complex and H2PCy soln. in THF was cooled to 0 °C in ice-bath, 2 h; chromy. on silica 60, eluent CH2Cl2/hexane=1:1, solvent was removed in high-vac.;	95%

pentamethylcyclopentadienyl niobium(V) tetrachloride (80432-35-5) + cyclohexylphosphine (822-68-4) → C5(CH3)5NbCl4(PH2C6H11) (499219-56-6)

Conditions	Yield
In toluene in dry Ar atmosphere C5(CH3)5NbCl4 suspended in toluene, equimolar amt. of PH2C6H11 added, stirred at room temp. until clear soln. obtained; solvent removed to dryness, residue extd. with-pentane, cooled to 5 °C, crystn.; elem. anal.;	95%

pentamethylcyclopentadienyl tantalum(V) tetrachloride + cyclohexylphosphine (822-68-4) → C5(CH3)5TaCl4(PH2C6H11) (406943-00-8)

Conditions	Yield
In toluene in dry Ar atmosphere C5(CH3)5TaCl4 suspended in toluene, equimolar amt. of PH2C6H11 added, stirred at room temp. until clear soln. obtained; solvent removed to dryness, residue extd. with-pentane, cooled to 5 °C, crystn.; elem. anal.;	95%

ortho-bromobenzaldehyde (6630-33-7) + cyclohexylphosphine (822-68-4) → C13H18BrOP (1246895-39-5)

Conditions	Yield
With trifluoroacetic acid at 80℃;	94%

benzyl sodium (1121-53-5) + N,N,N,N,-tetramethylethylenediamine (110-18-9) + tris(dimethylamino)stibine (7289-92-1) + cyclohexylphosphine (822-68-4) → Sb7Na3((CH3)2NCH2CH2N(CH3)2)3(C4H8O)3

Conditions	Yield
In tetrahydrofuran; hexane; toluene under Ar; Sb(NMe2)3 in toluene added to chilled soln. of C6H11PH2 (1:1)in hexane; warmed to room temp.; stirred for 10 min; added to soln. prepared from PhCH2Na and CyPH2 in hexane-THF at -20°C; excess TMEDAadded; warmed to 25°C; reflux; filtered while warm; stored at -35°C;	93%

[CyP(CH2SiMe2NPh)2]TaMe3 (850794-17-1) + cyclohexylphosphine (822-68-4) → [((CyP(CH2SiMe2NPh)2)Ta)2(μ-H)2(μ-PCy)] (850794-23-9)

Conditions	Yield
In diethyl ether byproducts: H2; (Ar); Schlenk or glovebox technique; phosphine was added via microsyringe to soln. of Ta complex in Et2O; stirred for 30 min; solvent removed (vac.); dissolved in pentane; dried (vac.); elem. anal.;	93%

tris(pentafluorophenyl)borate (1109-15-5) + cyclohexylphosphine (822-68-4) → (CyPH2)B(C6F5)3 (1015484-38-4)

Conditions	Yield
In toluene (N2), Schlenk technique; addn. of (C6H11)PH2 to soln. of B(C6F5)3 in toluene, stirring for 1 h at 25°C; evapn. in vacuo;	93%
In toluene at 25℃; Inert atmosphere;
In toluene phosphine combined with B(C6F5)3 in toluene; stirred at 25°C for 1 h; solvent concd.; detd. by (1)H, (11)B, (13)C, (19)F and (31)P NMR spectra;

ReMn(μ-H)(μ-P(cyclo-C6H11)2)(CO)8 (165550-99-2) + cyclohexylphosphine (822-68-4) → Re2(μ-H)(μ-P(cyclo-C6H11)2)(CO)7(ax/eq-H2P(cyclo-C6H11))

Conditions	Yield
With Me3NO In tetrahydrofuran metal-complex and H2PCy soln. in THF was cooled to 0 °C in ice-bath, 2 h; chromy. on silica 60, eluent CH2Cl2/hexane=1:1, solvent was removed in high-vac.;	92%

[(PhB(CH2P(i-Pr2)3)Ir(H)(η3-C8H13)] (697299-24-4) + cyclohexylphosphine (822-68-4) → [(C6H5B(CH2P(CH(CH3)2)2)3)IrH2(PH2(C6H11))] (697299-29-9)

Conditions	Yield
In benzene byproducts: 1,3-cyclooctadiene; (N2); Schlenk technique; neat PH2(C6H11) (1 equiv.) was added to soln. of Ir complex in C6H6 at room temp.; soln. was heated at 65°C for 14 h; filtered through Celite; solvent removed (vac.); elem. anal.;	92%

(CO)3{P(CH3)3}2Re(OSO2CF3) (138695-27-9) + cyclohexylphosphine (822-68-4) → (CO)3{P(CH3)3}2Re{PH2(C6H11)}(1+)*OSO2CF3(1-)={(CO)3(P(CH3)3)2Re(PH2(C6H11))}(O3SCF3) (144346-05-4)

Conditions

Yield

In tetrahydrofuran addn. THF (syringe) to evacuated Schlenk tube contg. Re-complex (previously flushed with Ar 3 times), mixt. stirred under Ar until complex dissolved, addn. phosphine (syringe), heated under reflux condenser overnight at 45°C; removal volatile materials (vac.), white residue washed twice (pentane), residue dissolved in THF, concd., layered with Et2O, cooled (-40°C, 2d), crystn., supernatant liq. removed (cannula), washed (pentane), dried (high vac., 12h), elem. anal.;

91%

trineopentylindium (106136-98-5) + cyclohexylphosphine (822-68-4) → [((CH3)3CCH2)2In(P(H)C6H11)]3

Conditions	Yield
In benzene byproducts: neopentane; Ar-atmosphere; 50°C (40 h); evapn., extg. (C6H6); elem. anal.;	90.9%

zirconocene dichloride (1291-32-3) + cyclohexylphosphine (822-68-4) → {(C5H5)2Zr(PHC6H11)}2

Conditions	Yield
With Mg In tetrahydrofuran N2-atmosphere; stirring of Zr-complex and excess of Mg (0.5 h), filtration, addn. of CyPH2; crystn. (overnight);	90%
With n-BuLi In tetrahydrofuran N2-atmosphere; addn. of BuLi to Zr-complex (-78°C), warming to room temp. (during 1 h), cooling (-78°C), addn. of CyPH2; crystn. (overnight, 25°C); elem. anal.;	50%

(acetonitrile)tri(carbonyl)bis(η-cyclopentadienyl)diiron + cyclohexylphosphine (822-68-4) → [Fe2(η5-C5H5)2(μ-CO)2(CO)(CyPH2)] (869802-98-2)

Conditions	Yield
In dichloromethane (N2); std. Schlenk technique; mixt. of Fe complex and P ligand in CH2Cl2was stirred at room temp. for 5 min; filtered; evapd. (vac.); washed (petroleum ether); elem. anal.;	90%

[((PhP(CH2SiMe2NPh)2)Ta)2(μ-H)4] + cyclohexylphosphine (822-68-4) → [((PhP(CH2SiMe2NPh)2)Ta)2(μ-H)2(μ-PCy)] (850794-22-8)

Conditions	Yield
In diethyl ether byproducts: H2; (Ar); Schlenk or glovebox technique; phosphine was added via microsyringe to soln. of Ta complex in Et2O; stirred for 30 min; solvent removed (vac.); dissolved in pentane; dried (vac.);	89%

([κ5-N,N,N,N,C-(Me3SiNCH2CH2)2NCH2CH2NSiMe2CH2]Zr + cyclohexylphosphine (822-68-4) → (N(Me3SiNCH2CH2)3)ZrPHCy (937801-08-6)

Conditions	Yield
In benzene (N2); soln. of cyclohexylphosphine in benzene was added to soln. of zirconium complex in benzene, stirred for 10 min; soln. was frozen, lyophilized;	89%

mesytaldehyde (487-68-3) + cyclohexylphosphine (822-68-4) → cyclohexyl-(2,4,6-trimethylbenzyl)phosphine oxide (1246895-42-0)

Conditions	Yield
With trifluoroacetic acid at 80℃;	89%

niobium pentachloride (10026-12-7) + cyclohexylphosphine (822-68-4) → bis(phenylphosphonium) hexachloroniobate(IV)

Conditions	Yield
In dichloromethane Ar-atmosphere; addn. of phosphine to slight excess of NbCl5 at -78°C, stirring at -78°C for 1 h, then at room temp. for 13 h; filtration (Celite), removal of volatiles (reduced pressure); elem. anal.;	88%

benzaldehyde (100-52-7) + cyclohexylphosphine (822-68-4) → benzylcyclohexylphosphine oxide (1246895-37-3)

Conditions	Yield
With trifluoroacetic acid at 80℃;	88%

niobium pentachloride (10026-12-7) + cyclohexylphosphine (822-68-4) → octachlorotetrakis(cyclohexylphosphine)diniobium(IV) + bis(cyclohexylphosphonium) hexachloroniobate(IV)

Conditions	Yield
In dichloromethane Ar-atmosphere; slight excess of phosphine, stirring at room temp. for 18h; filtration off of phosphonium salt, crystn. on layering with Et2O (24 h), decantation, drying (vac.); elem. anal.;	A 85% B 68%
In dichloromethane-d2 Ar-atmosphere; 1.9 equiv. phosphine, stirring at room temp. for 18 h; filtration off of phosphonium salt, crystn. on cooling filtrate to -20°C for 24 h, solvent removal; IR and NMR spectroscopy;	A 28% B 40%

Upstream product

• 1005-22-7 cyclohexylphosphonic dichloride 
• 2310-71-6 dicyclohexylphosphonous acid 
• 110-83-8 cyclohexene 
• 79564-48-0 Monoethoxicarbonylcyclohexylphosphan 
• 2844-89-5 dichlorocyclohexylphosphine 
• 80984-31-2 Os₃(CO)11P(C₆H₁₁)H₂ 

Downstream Products

• 58359-89-0 cyclohexyl-trimethyl-phosphonium; iodide 
• 14717-29-4 dicyclohexylphosphine oxide 
• 1095-93-8 (α-Hydroxy-benzyl)-benzyl-cyclohexyl-phosphinoxid 
• 95562-31-5 1-cyclohexyl-2,6-diphenyl-4-phosphorinanone 
• 91242-55-6 1-cyclohexyl-phosphinane 
• 92793-76-5 1-cyclohexyl-2,2,6,6-tetramethyl-phosphorinan-4-one 
• 72019-35-3 (2-tert-Butoxy-ethyl)-cyclohexyl-phosphane 
• 72019-33-1 Bis-(2-tert-butoxy-ethyl)-cyclohexyl-phosphane 
• 2617-43-8 2-Cyclohexylphosphino-essigsaeure 
• 3040-71-9 tetracyclohexylcyclotetraphosphine 
• 58158-17-1 C₆H₁₃F₂P 
• 79564-48-0 Monoethoxicarbonylcyclohexylphosphan 
• 79564-55-9 Diethoxicarbonylcyclohexylphosphan 
• 977-69-5 Cyclohexyl-bis--phosphin 

Relevant articles and documents

NOVEL VINYL PHOSPHINES AND PHOTO-INITIATORS OBTAINABLE THEREFROM

The present invention relates to a highly efficient process to prepare alkyl and vinyl phosphines which are useful as starting materials for novel bisacylphosphine oxides, bisacylphosphinic acids, salts, and derivatives thereof each bearing a vinyl functionality bound to the phosphorous atom as well as a versatile process for the preparation of the latter.

Carbonic Ester Phosphides - Synthesis and Chemical Behaviour

Primary phosphanes, RPH2, react with carbonic ester chlorides, ClCOOR', in the presence of K2CO3 to yield the title compounds RPHCOOR' and RP(COOR')2.The NMR data of the novel compounds are presented and discussed.Other physical and some chemical properties are described. - Key words: Carbonic Ester Phosphides, Mass Spectra, IR Spectra, NMR Spectra

SYNTHESES AND CHARACTERISATION OF , 2-H)Os3(CO)10(μ2-PRH)> (R=C6H5, p-CH3OC6H4, C6H11) AND 2-H)2Os3(CO)9(μ2-PR)> (R=C6H5, C6H11). INTERCONVERSION OF CLUSTER-BOUND PHOSPHINE AND PHOSPHIDO LIGANDS. CRYSTAL AND MOLECULAR STRUCTURES OF2-H).....

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