Tris(2-cyanoethyl)phosphine supplier

Name
TRIS(2-CYANOETHYL)PHOSPHINE
EINECS 223-687-0
CAS No. 4023-53-4
Article Data12
CAS DataBase
Density
Solubility Soluble in DMSO and H₂O
Melting Point 97-98°C
Formula C₉H₁₂N₃P
Boiling Point 426.9 °C at 760 mmHg
Molecular Weight 193.188
Flash Point 212 °C
Transport Information UN 3464
Appearance white crystalline
Safety 36/37/39-45-36-26
Risk Codes 20/21/22-36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms Propionitrile,3,3',3'-phosphinidynetri- (7CI);Propionitrile, 3,3',3''-phosphinidynetri-(6CI,8CI);NSC 41940;Phosphine, tris(2-cyanoethyl)-;Tris(2-cyanoethyl)phosphine;Tris(b-cyanoethyl)phosphine;
PSA 84.96000
LogP 2.20934

Synthetic route

: 107-13-1
acrylonitrile

A: 4023-49-8
bis(2-cyanoethyl)phosphine

B: 4023-53-4
tris(2-cyanoethyl)phosphine

C: 1439-41-4
tris(2-cyanoethyl)phosphine oxide

Conditions

Conditions	Yield
With potassium hydroxide; phosphan In water; acetonitrile for 1h; Ambient temperature;	A 15 % Spectr. B 45% C 15 % Spectr.
With phosphorus; potassium hydroxide In water; acetonitrile at 20 - 70℃; for 0.166667h; Irradiation; sonication;	A 10 % Spectr. B 30 % Spectr. C 60 % Spectr.

...Expand

: 107-13-1
acrylonitrile

: 4023-53-4
tris(2-cyanoethyl)phosphine

Conditions

Conditions	Yield
With potassium hydroxide; phosphan; acetonitrile
With phosphan

: 107-13-1
acrylonitrile

A: 4023-49-8
bis(2-cyanoethyl)phosphine

B: 4023-53-4
tris(2-cyanoethyl)phosphine

C: 6783-71-7
3-phosphanyl-propionitrile

Conditions

Conditions	Yield
With {(tris(cyanomethyl)phosphine)3platinum}; phosphan In acetonitrile at 20℃; for 1h; Product distribution; Mechanism;
With aluminum oxide; potassium hydroxide; phosphan Product distribution; influence of varying degrees of dryness of solid support;
With phosphan; In acetonitrile

...Expand

: 4023-49-8
bis(2-cyanoethyl)phosphine

: 107-13-1
acrylonitrile

: 4023-53-4
tris(2-cyanoethyl)phosphine

Conditions

Conditions	Yield
In acetonitrile

: 107-13-1
acrylonitrile

: 75-05-8
acetonitrile

phosphine: phosphine

aqueous KOH-solution: aqueous KOH-solution

A: 4023-49-8
bis(2-cyanoethyl)phosphine

B: 4023-53-4
tris(2-cyanoethyl)phosphine

C: 6783-71-7
3-phosphanyl-propionitrile

...Expand

: 4023-53-4
tris(2-cyanoethyl)phosphine

: 188638-31-5
[Pt(C8H12)(C3H4NO)2]

: 188638-33-7
[Pt(C3H4NO)2(P(CH2CH2CN)3)2]

Conditions

Conditions	Yield
In dichloromethane pptn. with light petroleum, filtration, washing (light petroleum), drying (vac.); elem. anal.;	100%

: 4023-53-4
tris(2-cyanoethyl)phosphine

: 200112-75-0
3-(perfluorooctyl)propyl iodide

: tris-(2-cyano-ethyl)-(4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11-heptadecafluoro-undecyl)-phosphonium; iodide

Conditions

Conditions	Yield
at 130 - 160℃; for 11h;	99.8%

: [Fe2(CO)6(μ-PhC=CH2)(μ-PPh2)]

: 4023-53-4
tris(2-cyanoethyl)phosphine

: 337380-82-2
Fe2(CO)5(P(CH2CH2CN)3)(HCCHC6H5)P(C6H5)2

Conditions

Conditions	Yield
In toluene byproducts: CO; (N2); refluxing a soln. of iron complex and phosphine in toluene for 20 min, cooling to room temp.; chromy (deactivated Al2O3, Et2O/light petroleum 2:3); elem. anal.;	98%

: 15617-18-2, 39958-10-6, 14220-64-5
bis(benzonitrile)palladium(II) dichloride

: 4023-53-4
tris(2-cyanoethyl)phosphine

: 204461-54-1, 68494-75-7
trans-PdCl2(tris(cyanoethyl)phosphine)2

Conditions

Conditions	Yield
In dichloromethane N2-atmosphere; dropwise addn. of 2 equiv. of phosphine to Pd-complex soln., stirring for 10 min (pptn.); filtration, washing (CH2Cl2), drying (vac.); elem. anal.;	98%

: (1,5-cyclooctadiene)dimethylplatinum(II)

: 4023-53-4
tris(2-cyanoethyl)phosphine

: 204391-74-2
cis-PtMe2(tris(cyanoethyl)phosphine)2

Conditions

Conditions	Yield
In acetone N2-atmosphere; dropwise addn. of ligand soln. to 0.5 equiv. of Pt-complex soln., stirring for 10 min; concn., pptn. on Et2O addn., filtration, washing (Et2O), drying (vac.); elem. anal.;	97%

: 39929-21-0
(tetrahydrothiophene)gold(I) chloride

: 4023-53-4
tris(2-cyanoethyl)phosphine

: 148100-44-1
{tris(2-cyanoethyl)phosphine}gold(I) chloride

Conditions

Conditions	Yield
In dichloromethane; acetonitrile N2; equimolar amounts; stirring for 1 h at room temperature;; precipitation upon addn. of diethyl ether;;	95%

: 4023-53-4
tris(2-cyanoethyl)phosphine

: 156457-81-7
bis(4-formylphenyl) azidothiophosphonate

: C23H22N4O4P2S

Conditions

Conditions	Yield
In acetonitrile Ambient temperature;	94%

: 12080-32-9
dichloro(1,5-cyclooctadiene)platinum(ll)

: 4023-53-4
tris(2-cyanoethyl)phosphine

: 20699-88-1
trans-PtCl2(tris(cyanoethyl)phosphine)2

Conditions

Conditions	Yield
In dichloromethane N2-atmosphere; dropwise addn. of ligand soln. to 0.5 equiv. of Pt-complex soln. (pptn.); filtration, washing (CH2Cl2), drying (vac.);	93%

: 4023-53-4
tris(2-cyanoethyl)phosphine

: [PdCl(η(3)-allyl)]2

: PdCl(tris(cyanoethyl)phosphine)(η(3)-allyl)

Conditions

Conditions	Yield
In acetone N2-atmosphere; stirring stoich. amts. for 10 min; concn., pptn. on Et2O addn., filtration, washing (Et2O), drying (vac.); elem. anal.;	93%

: 12092-47-6
di-μ-chloro-bis(1,5-cyclooctadiene)dirhodium

: 4023-53-4
tris(2-cyanoethyl)phosphine

: 204391-82-2
RhCl(tris(cyanoethyl)phosphine)(COD)

Conditions

Conditions	Yield
In acetone N2-atmosphere; stirring Rh-complex with 2 equiv. of phosphine for 15 min; concn., pptn. on Et2O addn.; elem. anal.;	93%

: 4023-53-4
tris(2-cyanoethyl)phosphine

: 204461-54-1, 68494-75-7
trans-PdCl2(tris(cyanoethyl)phosphine)2

: 200437-22-5
Pd(tris(cyanoethyl)phosphine)3

Conditions

Conditions	Yield
With LiOMe In methanol; ethanol N2-atmosphere; addn. of 4 equiv. of 0.1 M LiOMe (in MeOH) to EtOH, then addn. of 1 equiv. of Pd-complex and 2 equiv. phosphine, refluxing for 2 h (pptn.); filtration, washing (Et2O), drying (vac.); elem. anal.;	92%

: 4023-53-4
tris(2-cyanoethyl)phosphine

: 7474-83-1
3-bromo-1,2-naphthoquinone

A: 1439-41-4
tris(2-cyanoethyl)phosphine oxide

B: 61978-07-2
3-bromo-1,2-dihydroxynaphthalene

Conditions

Conditions	Yield
With water In dichloromethane for 24h; Inert atmosphere;	A 92% B 80%

...Expand

: 75-77-4
chloro-trimethyl-silane

: 14221-06-8, 744215-74-5
tetrakis(acetato)dimolybdenum(II)

: 4023-53-4
tris(2-cyanoethyl)phosphine

: [Mo2Cl4(tris(β-cyanoethyl)phosphine)2]x

Conditions

Conditions	Yield
In toluene N2-atmosphere; dropwise addn. of excess Me3SiCl to stoich. mixt. of Mo-compd. and ligand, stirring at room temp. for >= 2 d (pptn.); collection (filtration), washing (PhMe, 40°C; hexanes at room temp.; Et2O), drying (vac., room temp., >=12 h); elem. anal.;	90%
In tetrahydrofuran N2-atmosphere; dropwise addn. of excess Me3SiCl to stoich. mixt. of Mo-compd. and ligand, stirring at room temp. for >= 2 d (pptn.); collection (filtration), washing (PhMe, 40°C; hexanes at room temp.; Et2O), drying (vac., room temp., >=12 h);	90%
In benzene N2-atmosphere; dropwise addn. of excess Me3SiCl to stoich. mixt. of Mo-compd. and ligand, stirring at room temp. for >= 2 d (pptn.); collection (filtration), washing (PhMe, 40°C; hexanes at room temp.; Et2O), drying (vac., room temp., >=12 h);	90%

...Expand

: nickel(II) chloride hexahydrate

: cobalt(II) chloride hexahydrate

: 4023-53-4
tris(2-cyanoethyl)phosphine

: [Ni0.5Co0.5Cl2(P(CH2CH2CN)3)2]x

: [Ni0.5Co0.5Cl2(P(CH2CH2CN)3)2]x

: [Ni0.5Co0.5Cl2(P(CH2CH2CN)3)2]x

Conditions

Conditions	Yield
In ethanol; acetone EtOH:acetone:triethyl orthoformate=6:5:1, equimolar amts. of metal salts, excess of ligand, ambient temp. (pptn., then dissoln. of Ni-complex, crystn. of mixt. of products on slow evapn.); mixt. of products not separated;	A 8% B 90% C 2%

...Expand

: 4023-53-4
tris(2-cyanoethyl)phosphine

: {Co(CNC(CH3)3)4H2O}(2+)*2(ClO4)(1-)={Co(CNC(CH3)3)4H2O}(ClO4)2

: 101190-22-1
{Co(CNC(CH3)3)3(P(C2H4CN)3)2}(1+)*(ClO4)(1-)={Co(CNC(CH3)3)3(P(C2H4CN)3)2}(ClO4)

Conditions

Conditions	Yield
In acetonitrile at 0°C;; recrystallization from methylene dichloride and ether, elem. anal.;	89%

: 4023-53-4
tris(2-cyanoethyl)phosphine

: 51805-45-9
tris-(2-carboxyethyl)-phosphine hydrochloride

Conditions

Conditions	Yield
With hydrogenchloride for 2h; Heating;	88%

: 4023-53-4
tris(2-cyanoethyl)phosphine

: tris(bicyclo[2.2.1]heptene)platinum(0)

: 132199-05-4
{(tris(cyanomethyl)phosphine)3platinum}

Conditions

Conditions	Yield
In acetone; toluene N2-atmosphere; dropwise addn. of 3 equiv. of phosphine (in Me2CO) to Pt-complex soln. (in PhMe, pptn.), stirring for 3 h; filtration, dissoln. in Me2CO, pptn. on PhMe addn.; elem. anal.;	86%

: 4023-53-4
tris(2-cyanoethyl)phosphine

: silver nitrate

: 172915-72-9
bis[tris(2-cyanoethyl)phosphine]silver(I) nitrate

Conditions

Conditions	Yield
In ethanol; acetonitrile addn. of AgNO3 (in hot MeCN) to 2 equiv. of ligand (in warm EtOH); crystn. on slow cooling (in dark); elem. anal.;	85%

: tetrakis(acetonitrile)copper(I)tetrafluoroborate

: 4023-53-4
tris(2-cyanoethyl)phosphine

: 80510-03-8
Tris(pyrazolyl)methane

: [Cu{tris(pyrazol-1-yl)methane}(tris(2-cyanoethyl)phosphine)][BF4]

Conditions

Conditions	Yield
Stage #1: tetrakis(acetonitrile)copper(I)tetrafluoroborate; tris(2-cyanoethyl)phosphine In acetonitrile for 0.0833333h; Schlenk technique; Inert atmosphere; Stage #2: Tris(pyrazolyl)methane In acetonitrile for 4h; Schlenk technique; Inert atmosphere;	85%

...Expand

: {Ni(η-CH3C5H4)((C6H5)2PCH2CH2P(C6H5)2)}NCS

: 4023-53-4
tris(2-cyanoethyl)phosphine

: {Ni(η-CH3C5H4)((C6H5)2PCH2CH2P(C6H5)2)(P(CH2CH2CN)3)}NCS

Conditions

Conditions	Yield
In acetone addn. of phosphine soln. to stirred Ni complex soln. under N2; stirring, 4h; concentratin; addn. of hexane; pptn.; filtration; washing (Et2O); elem. anal.;	84%

: tetrachloronitridotechnatate(VI) tetra-n-butylammonium

: 4023-53-4
tris(2-cyanoethyl)phosphine

: (Bu4N){TcNCl3(tri(2-cyanoethyl)phosphine)}

Conditions

Conditions	Yield
In acetone refluxing (1 h); pptn. on concn., addn. of MeOH and cooling; elem. anal.;	83%

: 7681-65-4
copper(l) iodide

: 4023-53-4
tris(2-cyanoethyl)phosphine

: [CuI(tris(2-cyanoethyl)phosphine)]n

Conditions

Conditions	Yield
In acetonitrile for 0.333333h; Reflux; Inert atmosphere;	83%

: 64443-05-6
tetrakis(actonitrile)copper(I) hexafluorophosphate

: 4023-53-4
tris(2-cyanoethyl)phosphine

: [Cu(tris(2-cyanoethyl)phosphine)2]n(PF6)n

Conditions

Conditions	Yield
In acetonitrile for 1h; Reflux; Inert atmosphere;	83%

: di(rhodium)tetracarbonyl dichloride

: 4023-53-4
tris(2-cyanoethyl)phosphine

: trans-RhCl(CO)(tris(cyanoethyl)phosphine)2 * 0.5 Me2CO

Conditions

Conditions	Yield
In acetone N2-atmosphere; stirring Rh-complex with 4 equiv. of phosphine for 40 min; evapn.; elem. anal.;	82%

: chloro(1,5-cyclooctadiene)iridium(I) dimer

: 4023-53-4
tris(2-cyanoethyl)phosphine

: 204391-83-3
IrCl(tris(cyanoethyl)phosphine)(COD)

Conditions

Conditions	Yield
In acetone N2-atmosphere; stirring Ir-complex with 2 equiv. of phosphine for 15 min; concn., pptn. on Et2O addn.; elem. anal.;	82%

: 12080-32-9
dichloro(1,5-cyclooctadiene)platinum(ll)

: 4023-53-4
tris(2-cyanoethyl)phosphine

: 111046-55-0
PtCl2(CO)P(CH2CH2CN)3

Conditions

Conditions	Yield
With carbon monoxide In chloroform CO was bubbled through a soln. of Pt-complex in CHCl3 for 1 h, a soln. of the phosphine in hot CHCl3 was added dropwise over 30 min with stirring; ppt. was washed with CHCl3, recrystd. from acetone-propan-2-ol; elem. anal.;	81%

: 55272-36-1
[RuCl(η(5)-C5H4Me)(PPh3)2]

: 4023-53-4
tris(2-cyanoethyl)phosphine

: (C5H4CH3)RuCl(P(CH2CH2CN)3)2

Conditions

Conditions	Yield
In acetone N2 atmosphere; refluxing (1 h); concn. of aoln., pptn. (addn. of chloroform); elem. anal.;	79%
In toluene N2 atmosphere; refluxing (1.5 h), pptn.; dissolution (acetone), repptn. (addn. of chloroform); elem. anal.;	79%

Tris(2-cyanoethyl)phosphine Specification

The CAS registry number of Propanenitrile,3,3',3''-phosphinidynetris- is 4023-53-4. It belongs to the product category of Tertiary Phosphines. This chemical is also named as 3,3',3''-Phosphinetriyltripropanenitrile. Its EINECS registry number is 223-687-0. In addition, its molecular formula is C₉H₁₂N₃P and molecular weight is 193.18. Its IUPAC name is called 3-[bis(2-cyanoethyl)phosphanyl]propanenitrile.

Physical properties about Propanenitrile,3,3',3''-phosphinidynetris- are: (1)ACD/LogP: -0.25; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -0.25; (4)ACD/LogD (pH 7.4): -0.25; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 17.43; (8)ACD/KOC (pH 7.4): 17.43; (9)#H bond acceptors: 3; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 6; (12)Flash Point: 212 °C; (13)Enthalpy of Vaporization: 68.17 kJ/mol; (14)Boiling Point: 426.9 °C at 760 mmHg.

Preparation: this chemical can be prepared by acrylonitrile. This reaction will need reagents PH₃, KOH and solvents acetonitrile, H₂O. The reaction time is 1 hour at ambient temperature. The yield is about 45 %.

Propanenitrile,3,3',3''-phosphinidynetris- can be prepared by acrylonitrile

Uses of Propanenitrile,3,3',3''-phosphinidynetris-: it can be used to produce 3,3',3''-phosphanetriyl-tri-propionic acid and hydrochloride by heating. It will need reagent conc. aq. HCl with reaction time of 2 hours. The yield is about 88 %.

Propanenitrile,3,3',3''-phosphinidynetris- can be used to produce 3,3',3''-phosphanetriyl-tri-propionic acid and hydrochloride

When you are using this chemical, please be cautious about it as the following:
This chemical may cause inflammation to the skin or other mucous membranes. It is harmful by inhalation, in contact with skin and if swallowed. It is irritating to eyes, respiratory system and skin. In case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice. Whenever you will contact it, please wear suitable protective clothing, gloves and eye/face protection. In case of accident or if you feel unwell seek medical advice immediately (show the label where possible).

You can still convert the following datas into molecular structure:
(1)SMILES: N#CCCP(CCC#N)CCC#N
(2)InChI: InChI=1/C9H12N3P/c10-4-1-7-13(8-2-5-11)9-3-6-12/h1-3,7-9H2
(3)InChIKey: CHZAMJVESILJGH-UHFFFAOYAA

Product Name

TRIS(2-CYANOETHYL)PHOSPHINE

Synthetic route

Tris(2-cyanoethyl)phosphine Specification

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