Phosphine, cyclohexyl- supplier

Name
CYCLOHEXYLPHOSPHINE
EINECS
CAS No. 822-68-4
Article Data14
CAS DataBase
Density 0,875 g/cm3
Solubility
Melting Point
Formula C₆H₁₃P
Boiling Point 145 °C at 760 mmHg
Molecular Weight 116.143
Flash Point 41.5 °C
Transport Information UN 3185
Appearance colourless liquid with an offensive odour
Safety 9-16-26-36/37/39
Risk Codes 17-20/21/22-34
Molecular Structure
Hazard Symbols
Synonyms Cyclohexylphosphine;
PSA 13.59000
LogP 2.19420

Synthetic route

: 2310-71-6
dicyclohexylphosphonous acid

A: 1005-23-8
cyclohexylphosphonic acid

B: 822-68-4
cyclohexylphosphine

Conditions

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;

: 79564-48-0
Monoethoxicarbonylcyclohexylphosphan

A: 64-17-5
ethanol

B: 822-68-4
cyclohexylphosphine

C CO2: CO2

Conditions

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

...Expand

: 1005-22-7
cyclohexylphosphonic dichloride

: 822-68-4
cyclohexylphosphine

Conditions

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

: 110-83-8
cyclohexene

: 822-68-4
cyclohexylphosphine

Conditions

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

: 110-83-8
cyclohexene

phosphine: phosphine

: 822-68-4
cyclohexylphosphine

Conditions

Conditions	Yield
UV-Licht.Irradiation;

: 80984-31-2
Os3(CO)11P(C6H11)H2

: 822-68-4
cyclohexylphosphine

Conditions

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

: 2844-89-5
dichlorocyclohexylphosphine

: 822-68-4
cyclohexylphosphine

Conditions

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;

: 31080-62-3
diisopropylallylphosphonite

: 822-68-4
cyclohexylphosphine

: 850716-19-7
C6H11P(C3H6P(OCH(CH3)2)2)2

Conditions

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

: 822-68-4
cyclohexylphosphine

: dimethylallylphosphonite

: 850716-21-1
C6H11P(C3H6P(OCH3)2)2

Conditions

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

: 109-64-8
1,3-dibromo-propane

: 822-68-4
cyclohexylphosphine

: 97472-13-4
1,3-bis(cyclohexylphosphanyl)propane

Conditions

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%

: 822-68-4
cyclohexylphosphine

: C6H14BP

Conditions

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

: 109-04-6
2-bromo-pyridine

: 822-68-4
cyclohexylphosphine

: 380358-80-5
cyclohexylbis(2-pyridyl)phosphane

Conditions

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

: 50-00-0
formaldehyd

: 822-68-4
cyclohexylphosphine

: 5958-45-2
bis-(hydroxymethyl)cyclohexylphosphine

Conditions

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

: 822-68-4
cyclohexylphosphine

: 316803-49-3
Mn2(μ-H)(μ-P(cyclo-C6H11)2)(CO)7(ax-H2P(cyclo-C6H11))

Conditions

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

: 822-68-4
cyclohexylphosphine

: 191542-23-1
(cyclohexylphosphane)(methylcyclopentadienyl)molybdenium tetrachloride

Conditions

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%

: 630-19-3
pivalaldehyde

: 822-68-4
cyclohexylphosphine

: 1246895-40-8
C11H23OP

Conditions

Conditions	Yield
With trifluoroacetic acid at 80℃;	97%

: 7550-45-0
titanium tetrachloride

: 822-68-4
cyclohexylphosphine

: 469886-23-5, 165281-61-8
(TiCl4(C6H11PH2)2)

Conditions

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%

: 26260-02-6
2-iodobenzaldehyde

: 822-68-4
cyclohexylphosphine

: 1246895-38-4
C13H18IOP

Conditions

Conditions	Yield
With trifluoroacetic acid at 80℃;	96%

: mu-hydrido-mu-dicyclohexyl-phosphido-octacarbonyl-dirhenium

: 822-68-4
cyclohexylphosphine

: 316803-45-9
Re2(μ-H)(μ-P(cyclo-C6H11)2)(CO)7(ax-H2P(cyclo-C6H11))

Conditions

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%

: 80432-35-5
pentamethylcyclopentadienyl niobium(V) tetrachloride

: 822-68-4
cyclohexylphosphine

: 499219-56-6
C5(CH3)5NbCl4(PH2C6H11)

Conditions

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

: 822-68-4
cyclohexylphosphine

: 406943-00-8
C5(CH3)5TaCl4(PH2C6H11)

Conditions

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%

: 6630-33-7
ortho-bromobenzaldehyde

: 822-68-4
cyclohexylphosphine

: 1246895-39-5
C13H18BrOP

Conditions

Conditions	Yield
With trifluoroacetic acid at 80℃;	94%

: 1121-53-5
benzyl sodium

: 110-18-9
N,N,N,N,-tetramethylethylenediamine

: 7289-92-1
tris(dimethylamino)stibine

: 822-68-4
cyclohexylphosphine

: Sb7Na3((CH3)2NCH2CH2N(CH3)2)3(C4H8O)3

Conditions

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%

...Expand

: 850794-17-1
[CyP(CH2SiMe2NPh)2]TaMe3

: 822-68-4
cyclohexylphosphine

: 850794-23-9
[((CyP(CH2SiMe2NPh)2)Ta)2(μ-H)2(μ-PCy)]

Conditions

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%

: 1109-15-5
tris(pentafluorophenyl)borate

: 822-68-4
cyclohexylphosphine

: 1015484-38-4
(CyPH2)B(C6F5)3

Conditions

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;

: 165550-99-2
ReMn(μ-H)(μ-P(cyclo-C6H11)2)(CO)8

: 822-68-4
cyclohexylphosphine

: Re2(μ-H)(μ-P(cyclo-C6H11)2)(CO)7(ax/eq-H2P(cyclo-C6H11))

Conditions

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%

: 697299-24-4
[(PhB(CH2P(i-Pr2)3)Ir(H)(η3-C8H13)]

: 822-68-4
cyclohexylphosphine

: 697299-29-9
[(C6H5B(CH2P(CH(CH3)2)2)3)IrH2(PH2(C6H11))]

Conditions

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%

: 138695-27-9
(CO)3{P(CH3)3}2Re(OSO2CF3)

: 822-68-4
cyclohexylphosphine

: 144346-05-4
(CO)3{P(CH3)3}2Re{PH2(C6H11)}(1+)*OSO2CF3(1-)={(CO)3(P(CH3)3)2Re(PH2(C6H11))}(O3SCF3)

Conditions

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%

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%

: 106136-98-5
trineopentylindium

: 822-68-4
cyclohexylphosphine

: [((CH3)3CCH2)2In(P(H)C6H11)]3

Conditions

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

: 1291-32-3
zirconocene dichloride

: 822-68-4
cyclohexylphosphine

: {(C5H5)2Zr(PHC6H11)}2

Conditions

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

: 822-68-4
cyclohexylphosphine

: 869802-98-2
[Fe2(η5-C5H5)2(μ-CO)2(CO)(CyPH2)]

Conditions

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]

: 822-68-4
cyclohexylphosphine

: 850794-22-8
[((PhP(CH2SiMe2NPh)2)Ta)2(μ-H)2(μ-PCy)]

Conditions

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

: 822-68-4
cyclohexylphosphine

: 937801-08-6
(N(Me3SiNCH2CH2)3)ZrPHCy

Conditions

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%

: 487-68-3
mesytaldehyde

: 822-68-4
cyclohexylphosphine

: 1246895-42-0
cyclohexyl-(2,4,6-trimethylbenzyl)phosphine oxide

Conditions

Conditions	Yield
With trifluoroacetic acid at 80℃;	89%

: 10026-12-7
niobium pentachloride

: 822-68-4
cyclohexylphosphine

: bis(phenylphosphonium) hexachloroniobate(IV)

Conditions

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%

: 100-52-7
benzaldehyde

: 822-68-4
cyclohexylphosphine

: 1246895-37-3
benzylcyclohexylphosphine oxide

Conditions

Conditions	Yield
With trifluoroacetic acid at 80℃;	88%

: 10026-12-7
niobium pentachloride

: 822-68-4
cyclohexylphosphine

: octachlorotetrakis(cyclohexylphosphine)diniobium(IV)

B: bis(cyclohexylphosphonium) hexachloroniobate(IV)

Conditions

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%

...Expand

Phosphine, cyclohexyl- Specification

This chemical is called Phosphine, cyclohexyl-, and its CAS registry number is 822-68-4. With the molecular formula of C₆H₁₃P, its product category is Primary Phosphines. It's incompatible with organic material, air, oxidizing agents, halogens. Store it under an inert atmosphere.

Other characteristics of the Phosphine, cyclohexyl- can be summarised as followings: (1)#H bond acceptors: 0; (2)#H bond donors: 0; (3)#Freely Rotating Bonds: 1; (4)Polar Surface Area: 13.59 Å²; (5)Flash Point: 41.5 °C; (6)Enthalpy of Vaporization: 36.63 kJ/mol; (7)Boiling Point: 145 °C at 760 mmHg; (8)Vapour Pressure: 6.25 mmHg at 25°C.

Uses of this chemical: The Phosphine, cyclohexyl- could react with 3-chlorocarbonyloxy-propene, and obtain the Monoallyloxycarbonyl-cyclohexylphosphan. This reaction needs the reagent of K₂CO₃, and the solvent of benzene. The yield is 73.7 %. In addition, this reaction should be taken for 6 hours. The other condition is heating.

The Phosphine, cyclohexyl- could react with 3-chlorocarbonyloxy-propene, and obtain the Monoallyloxycarbonyl-cyclohexylphosphan

When you are using this chemical, please be cautious about it as the following: This chemical is spontaneously flammable in air. Keep it away from sources of ignition. It's harmful by inhalation, in contacting with skin and if swallowed. It causes burns. Wear suitable protective clothing, gloves and eye/face protection. In case of contacting with eyes, rinse immediately with plenty of water and seek medical advice. Keep the container in a well-ventilated place.

You can still convert the following datas into molecular structure:
1.SMILES: PC1CCCCC1
2.InChI: InChI=1/C6H13P/c7-6-4-2-1-3-5-6/h6H,1-5,7H2
3.InChIKey: ZBCKWHYWPLHBOK-UHFFFAOYAG

Product Name

CYCLOHEXYLPHOSPHINE

Synthetic route

Phosphine, cyclohexyl- Specification

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