Product Name

  • Name

    Tripiperidinophosphine

  • EINECS
  • CAS No. 13954-38-6
  • Article Data17
  • CAS DataBase
  • Density
  • Solubility
  • Melting Point
  • Formula C15H30N3P
  • Boiling Point 370.2 °C at 760 mmHg
  • Molecular Weight 283.397
  • Flash Point 177.7 °C
  • Transport Information
  • Appearance Gray-white power
  • Safety
  • Risk Codes
  • Molecular Structure Molecular Structure of 13954-38-6 (Tripiperidinophosphine)
  • Hazard Symbols
  • Synonyms Piperidine,1,1',1''-phosphinidynetri- (6CI,7CI,8CI);1,1',1''-Phosphinidynetripiperidine;NSC 99043;Phosphine, tri-1-piperidinyl-;Phosphorous tripiperidide;Tripiperidinophosphine;Tripiperidylphosphine;Tris(1-piperidinyl)phosphine;Tris(piperidino)phosphine;
  • PSA 23.31000
  • LogP 3.48470

Synthetic route

piperidine
110-89-4

piperidine

tripiperidino-phosphine
13954-38-6

tripiperidino-phosphine

Conditions
ConditionsYield
With phosphorus trichloride In diethyl ether100%
With triethylamine; phosphorus trichloride In diethyl ether at 20℃; for 1h;76%
With phosphorus trichloride In diethyl ether at 0 - 20℃;76%
piperidine
110-89-4

piperidine

hexaethylphosphoric triamide
2283-11-6

hexaethylphosphoric triamide

tripiperidino-phosphine
13954-38-6

tripiperidino-phosphine

Conditions
ConditionsYield
at 70℃; for 10h;95%
C30H46N4O2P2
863650-25-3

C30H46N4O2P2

A

2,6-dipiperidino-1,3,5,7-tetraoxa-2,6-diphospha-4,8(1,3)-dinaphthalenacyclooctaphane
914468-02-3

2,6-dipiperidino-1,3,5,7-tetraoxa-2,6-diphospha-4,8(1,3)-dinaphthalenacyclooctaphane

B

tripiperidino-phosphine
13954-38-6

tripiperidino-phosphine

Conditions
ConditionsYield
A 41%
B n/a
C30H46N4O2P2

C30H46N4O2P2

A

cyclo[bis(1,6-naphthylenepiperidinophosphite)]

cyclo[bis(1,6-naphthylenepiperidinophosphite)]

B

tripiperidino-phosphine
13954-38-6

tripiperidino-phosphine

Conditions
ConditionsYield
A 39%
B n/a
C30H46N4O2P2

C30H46N4O2P2

A

cyclo[bis(2,6-naphthylenepiperidylamidophosphite)]

cyclo[bis(2,6-naphthylenepiperidylamidophosphite)]

B

tripiperidino-phosphine
13954-38-6

tripiperidino-phosphine

Conditions
ConditionsYield
A 28%
B n/a
piperidine
110-89-4

piperidine

bis(piperidinyl)chlorophosphine
61123-73-7

bis(piperidinyl)chlorophosphine

tripiperidino-phosphine
13954-38-6

tripiperidino-phosphine

Conditions
ConditionsYield
With triethylamine
piperidine
110-89-4

piperidine

diethyl ether
60-29-7

diethyl ether

phosphorus trichloride
7719-12-2, 52843-90-0

phosphorus trichloride

tripiperidino-phosphine
13954-38-6

tripiperidino-phosphine

C16H25N2OP
24979-62-2

C16H25N2OP

A

1-Diphenoxyphosphinyl-piperidin
38945-81-2

1-Diphenoxyphosphinyl-piperidin

B

tripiperidino-phosphine
13954-38-6

tripiperidino-phosphine

Conditions
ConditionsYield
In 1,4-dioxane at 20℃; for 936h; Title compound not separated from byproducts;
In 1,4-dioxane at 20℃; for 480h; Title compound not separated from byproducts.;
C16H24ClN2OP

C16H24ClN2OP

A

tripiperidino-phosphine
13954-38-6

tripiperidino-phosphine

B

C17H18Cl2NO2P

C17H18Cl2NO2P

Conditions
ConditionsYield
at 20℃; Title compound not separated from byproducts;
C20H27N2OP

C20H27N2OP

A

tripiperidino-phosphine
13954-38-6

tripiperidino-phosphine

B

C25H24NO2P

C25H24NO2P

Conditions
ConditionsYield
at 20℃; Title compound not separated from byproducts;
C26H44N4O2P2

C26H44N4O2P2

A

tripiperidino-phosphine
13954-38-6

tripiperidino-phosphine

B

C22H28N2O4P2
502922-91-0

C22H28N2O4P2

Conditions
ConditionsYield
In acetonitrile at 20℃; for 1464h; Title compound not separated from byproducts.;
C26H44N4O2P2

C26H44N4O2P2

A

C22H28N2O4P2
863650-16-2

C22H28N2O4P2

B

tripiperidino-phosphine
13954-38-6

tripiperidino-phosphine

Conditions
ConditionsYield
In acetonitrile at 20℃; for 2304h; Title compound not separated from byproducts.;
C32H48N4O2P2

C32H48N4O2P2

A

C34H36N2O4P2
863650-17-3

C34H36N2O4P2

B

tripiperidino-phosphine
13954-38-6

tripiperidino-phosphine

Conditions
ConditionsYield
In acetonitrile at 20℃; for 960h; Title compound not separated from byproducts.;
piperidine
110-89-4

piperidine

chromium hexacarbonyl

chromium hexacarbonyl

tripiperidino-phosphine
13954-38-6

tripiperidino-phosphine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 52 percent / hexane / 0 - 20 °C
2: dioxane / 936 h / 20 °C
View Scheme
Multi-step reaction with 2 steps
1: 81 percent / hexane / 0 - 20 °C
2: 20 °C
View Scheme
Multi-step reaction with 2 steps
1: 85 percent / hexane / 0 - 20 °C
2: 20 °C
View Scheme
dichloro(1,5-cyclooctadiene)palladium(II)
12107-56-1

dichloro(1,5-cyclooctadiene)palladium(II)

tripiperidino-phosphine
13954-38-6

tripiperidino-phosphine

dichloro{bis[1,1’,1’’-(phosphinetriyl)tripiperidine]}palladium(II)
68494-72-4, 955117-31-4

dichloro{bis[1,1’,1’’-(phosphinetriyl)tripiperidine]}palladium(II)

Conditions
ConditionsYield
In toluene at 20℃; for 0.166667h;100%
dichloro(1,5-cyclooctadiene)palladium(II)
12107-56-1

dichloro(1,5-cyclooctadiene)palladium(II)

tripiperidino-phosphine
13954-38-6

tripiperidino-phosphine

dicloro(bis(1,1',1''-(phosphinetriyl)tripiperidine))palladium
955117-31-4, 68494-72-4

dicloro(bis(1,1',1''-(phosphinetriyl)tripiperidine))palladium

Conditions
ConditionsYield
In toluene two equivalents of phosphine-compd. added to Pd-compd. in toluene under N2 at room temp.;99%
tripiperidino-phosphine
13954-38-6

tripiperidino-phosphine

t-butyl azide
13686-33-4

t-butyl azide

tris(1-piperidinyl)(tert-butyl)phosphazide

tris(1-piperidinyl)(tert-butyl)phosphazide

Conditions
ConditionsYield
at 0 - 20℃;91%
tripiperidino-phosphine
13954-38-6

tripiperidino-phosphine

tetraphenylethylresorcin[4]arene
118600-22-9

tetraphenylethylresorcin[4]arene

2,8,14,20-tetrakis(2-phenylethyl)-5,9,13,17-tetra(piperidin-1-yl)-2,20:3,19-dimetheno-1H,21H,23H,25H-bis[1,3,2]dioxaphosphocino[5,4-i:5'.4'-i']benzo[1.2-d:5.4-d']benzobis[1,3,2]dioxaphosphocine

2,8,14,20-tetrakis(2-phenylethyl)-5,9,13,17-tetra(piperidin-1-yl)-2,20:3,19-dimetheno-1H,21H,23H,25H-bis[1,3,2]dioxaphosphocino[5,4-i:5'.4'-i']benzo[1.2-d:5.4-d']benzobis[1,3,2]dioxaphosphocine

Conditions
ConditionsYield
In 1,4-dioxane at 20℃; for 168h;87%
dichloro(1,3-bis(2,4,6-trimethylphenyl)-2-imidazolidinylylidene)(benzylidene)bis(pyridine)ruthenium(II)

dichloro(1,3-bis(2,4,6-trimethylphenyl)-2-imidazolidinylylidene)(benzylidene)bis(pyridine)ruthenium(II)

tripiperidino-phosphine
13954-38-6

tripiperidino-phosphine

C43H62Cl2N5PRu

C43H62Cl2N5PRu

Conditions
ConditionsYield
In tetrahydrofuran at 20℃; for 0.333333h;78%
tripiperidino-phosphine
13954-38-6

tripiperidino-phosphine

1,8-diazidonaphthalene
22187-34-4

1,8-diazidonaphthalene

1,8-bis[tris(piperidino)phosphazidyl]naphthalene

1,8-bis[tris(piperidino)phosphazidyl]naphthalene

Conditions
ConditionsYield
In tetrahydrofuran at 20℃; for 2h; Staudinger Azide Reduction; Inert atmosphere; Schlenk technique;77%
tripiperidino-phosphine
13954-38-6

tripiperidino-phosphine

trimethylsilylazide
4648-54-8

trimethylsilylazide

N-trimethylsilyl[tris(piperidino)]phosphazene

N-trimethylsilyl[tris(piperidino)]phosphazene

Conditions
ConditionsYield
In toluene for 2h; Staudinger Azide Reduction; Reflux; Inert atmosphere; Schlenk technique;77%
tripiperidino-phosphine
13954-38-6

tripiperidino-phosphine

1,3-dihydroxynaphthalene
132-86-5

1,3-dihydroxynaphthalene

2,6-dipiperidino-1,3,5,7-tetraoxa-2,6-diphospha-4,8(1,3)-dinaphthalenacyclooctaphane
914468-02-3

2,6-dipiperidino-1,3,5,7-tetraoxa-2,6-diphospha-4,8(1,3)-dinaphthalenacyclooctaphane

Conditions
ConditionsYield
In acetonitrile; benzene at 20℃;70%
tripiperidino-phosphine
13954-38-6

tripiperidino-phosphine

tripiperidylphosphonium tetrafluoroborate

tripiperidylphosphonium tetrafluoroborate

Conditions
ConditionsYield
With tetrafluoroboric acid In diethyl ether68%
With tetrafluoroboric acid In diethyl ether
tripiperidino-phosphine
13954-38-6

tripiperidino-phosphine

Bromoacetaldehyde diethyl acetal
2032-35-1

Bromoacetaldehyde diethyl acetal

(2,2-diethoxyethyl)trispiperidinophosphonium bromide

(2,2-diethoxyethyl)trispiperidinophosphonium bromide

Conditions
ConditionsYield
at 80℃; for 4h; Inert atmosphere;63.5%
Heating;
tripiperidino-phosphine
13954-38-6

tripiperidino-phosphine

C-1-naphthylresorcin[4]arene
916134-80-0

C-1-naphthylresorcin[4]arene

C148H200N16O8P8

C148H200N16O8P8

Conditions
ConditionsYield
In 1,4-dioxane at 80 - 85℃; for 18h; Inert atmosphere; regioselective reaction;61%
tripiperidino-phosphine
13954-38-6

tripiperidino-phosphine

C64H64O8
1069117-64-1

C64H64O8

5,11,17,23-tetramethyl-2,8,14,20-tetrakis(2-phenylethyl)-5,9,13,17-tetra(piperidin-1-yl)-2,20:3,19-dimetheno-1H,21H,23H,25H-bis[1,3,2]dioxaphosphocino[5,4-i:5'.4'-i']benzo[1.2-d:5.4-d']benzobis[1,3,2]dioxaphosphocine

5,11,17,23-tetramethyl-2,8,14,20-tetrakis(2-phenylethyl)-5,9,13,17-tetra(piperidin-1-yl)-2,20:3,19-dimetheno-1H,21H,23H,25H-bis[1,3,2]dioxaphosphocino[5,4-i:5'.4'-i']benzo[1.2-d:5.4-d']benzobis[1,3,2]dioxaphosphocine

Conditions
ConditionsYield
In 1,4-dioxane at 20℃; for 168h;60%
tripiperidino-phosphine
13954-38-6

tripiperidino-phosphine

ethene
74-85-1

ethene

nickel(II) acetylacetonate
3264-82-2

nickel(II) acetylacetonate

C2H4Ni(P(NC5H10)3)2
12150-27-5

C2H4Ni(P(NC5H10)3)2

Conditions
ConditionsYield
With (C2H5)2AlOC2H5 In not given prepn. at room temp.;;60%
With (C2H5)2AlOC2H5 In not given prepn. at room temp.;;60%
tripiperidino-phosphine
13954-38-6

tripiperidino-phosphine

Ru(CO)(toluene)((9,9-dimethylxanthene-4,5-diyl)bis(dimethylsilyl))
226943-17-5

Ru(CO)(toluene)((9,9-dimethylxanthene-4,5-diyl)bis(dimethylsilyl))

Ru{κ3(Si,O,Si)-xantsil}(CO){P(NC5H10)3}

Ru{κ3(Si,O,Si)-xantsil}(CO){P(NC5H10)3}

Conditions
ConditionsYield
In tetrahydrofuran at 20℃; for 2h;60%
tripiperidino-phosphine
13954-38-6

tripiperidino-phosphine

C-methylcalix[4]resorcinarene
74708-10-4

C-methylcalix[4]resorcinarene

1,21,23,25-tetramethyl-5,9,13,17-tetrakis(piperidylamido)-2,20:3,19-dimetheno-1H,21H,23H,25H-bis[1,3,2-λ3]dioxaphosphocino[5,4-i:5',4'-i']benzo[1,2-d:4,5-d']bis[1,3,2-λ3]benzodioxaphosphocine

1,21,23,25-tetramethyl-5,9,13,17-tetrakis(piperidylamido)-2,20:3,19-dimetheno-1H,21H,23H,25H-bis[1,3,2-λ3]dioxaphosphocino[5,4-i:5',4'-i']benzo[1,2-d:4,5-d']bis[1,3,2-λ3]benzodioxaphosphocine

Conditions
ConditionsYield
In 1,4-dioxane at 20℃; for 168h;52%
tripiperidino-phosphine
13954-38-6

tripiperidino-phosphine

C60H120K4N16P4

C60H120K4N16P4

Conditions
ConditionsYield
Stage #1: tripiperidino-phosphine With trimethylsilylazide In toluene for 12h; Glovebox; Reflux; Schlenk technique; Inert atmosphere;
Stage #2: With sulfuric acid In methanol for 24h; Inert atmosphere;
Stage #3: With benzyl potassium In toluene for 3h; Inert atmosphere;
52%
Stage #1: tripiperidino-phosphine With trimethylsilylazide In toluene for 12h; Inert atmosphere; Reflux; Schlenk technique;
Stage #2: With sulfuric acid In methanol for 24h; Inert atmosphere; Schlenk technique;
Stage #3: With benzyl potassium In toluene for 3h; Glovebox; Inert atmosphere;
52%
tripiperidino-phosphine
13954-38-6

tripiperidino-phosphine

C72H56O8

C72H56O8

C112H132N8O8P4

C112H132N8O8P4

Conditions
ConditionsYield
In 1,4-dioxane at 80 - 85℃; for 1h; Inert atmosphere; regioselective reaction;51%
tripiperidino-phosphine
13954-38-6

tripiperidino-phosphine

1,3-dihydroxynaphthalene
132-86-5

1,3-dihydroxynaphthalene

cyclo[bis(1,3-naphthylenepiperidylamidophosphite)]

cyclo[bis(1,3-naphthylenepiperidylamidophosphite)]

Conditions
ConditionsYield
In acetonitrile at 20℃;41%
tripiperidino-phosphine
13954-38-6

tripiperidino-phosphine

1,6-dihydroxynaphthalene
575-44-0

1,6-dihydroxynaphthalene

cyclo[bis(1,6-naphthylenepiperidinophosphite)]

cyclo[bis(1,6-naphthylenepiperidinophosphite)]

Conditions
ConditionsYield
In acetonitrile at 20℃; for 24h;41%
tripiperidino-phosphine
13954-38-6

tripiperidino-phosphine

1,7-Dihydroxynaphthalene
575-38-2

1,7-Dihydroxynaphthalene

A

C30H32N2O4P2

C30H32N2O4P2

B

C30H32N2O4P2

C30H32N2O4P2

Conditions
ConditionsYield
Stage #1: tripiperidino-phosphine In acetonitrile at 20℃; for 4h;
Stage #2: 1,7-Dihydroxynaphthalene In acetonitrile at 20℃; for 4h;
A 39%
B n/a
In acetonitrile at 20℃; for 4h;A 39%
B n/a
tripiperidino-phosphine
13954-38-6

tripiperidino-phosphine

1,6-dihydroxynaphthalene
575-44-0

1,6-dihydroxynaphthalene

cyclo[bis(1,6-naphthylenepiperidylamidophosphite)]

cyclo[bis(1,6-naphthylenepiperidylamidophosphite)]

Conditions
ConditionsYield
In acetonitrile at 20℃;39%
tripiperidino-phosphine
13954-38-6

tripiperidino-phosphine

1,6-dihydroxynaphthalene
575-44-0

1,6-dihydroxynaphthalene

1,6-bis(dipiperidinothiophosphoryloxy)naphthalene
1609488-32-5

1,6-bis(dipiperidinothiophosphoryloxy)naphthalene

Conditions
ConditionsYield
Stage #1: tripiperidino-phosphine; 1,6-dihydroxynaphthalene In acetonitrile at 20℃; for 0.666667h;
Stage #2: With sulfur In acetonitrile for 4h;
39%
tripiperidino-phosphine
13954-38-6

tripiperidino-phosphine

1,7-Dihydroxynaphthalene
575-38-2

1,7-Dihydroxynaphthalene

A

C30H32N2O4P2S2

C30H32N2O4P2S2

B

C30H32N2O4P2S2

C30H32N2O4P2S2

Conditions
ConditionsYield
Stage #1: tripiperidino-phosphine; 1,7-Dihydroxynaphthalene In acetonitrile at 20℃; for 4h;
Stage #2: With sulfur In dichloromethane at 20℃; for 2.5h;
A 32%
B 28%
Stage #1: tripiperidino-phosphine In acetonitrile at 20℃; for 4h;
Stage #2: 1,7-Dihydroxynaphthalene In acetonitrile at 20℃; for 4h;
Stage #3: With sulfur In dichloromethane at 20℃; for 2.5h;
tripiperidino-phosphine
13954-38-6

tripiperidino-phosphine

p-xylylene glycol
589-29-7

p-xylylene glycol

1,4-bis(dipiperidin-1-ylthiophosphoryloxy)xylene

1,4-bis(dipiperidin-1-ylthiophosphoryloxy)xylene

Conditions
ConditionsYield
Stage #1: tripiperidino-phosphine; p-xylylene glycol In 1,4-dioxane at 20℃; for 48h;
Stage #2: With sulfur In 1,4-dioxane at 20℃; for 72h; Further stages.;
32%
2,6-Dihydroxynaphthalene
581-43-1

2,6-Dihydroxynaphthalene

tripiperidino-phosphine
13954-38-6

tripiperidino-phosphine

cyclo[bis(2,6-naphthylenepiperidylamidophosphite)]

cyclo[bis(2,6-naphthylenepiperidylamidophosphite)]

Conditions
ConditionsYield
In acetonitrile at 20℃;28%

Tripiperidinophosphine Specification

The CAS register number of Tripiperidinophosphine is 13954-38-6. It also can be called as Tri(piperidin-1-yl)phosphane and the systematic name about this chemical is 1,1',1''-phosphanetriyltripiperidine. The molecular formula about this chemical is C15H30N3P and molecular weight is 283.39.

Physical properties about Tripiperidinophosphine are: (1)ACD/LogP: 2.47; (2)ACD/LogD (pH 5.5): -0.63; (3)ACD/LogD (pH 7.4): -0.62; (4)ACD/BCF (pH 5.5): 1; (5)ACD/BCF (pH 7.4): 1; (6)ACD/KOC (pH 5.5): 1; (7)ACD/KOC (pH 7.4): 1; (8)#H bond acceptors: 3; (9)#Freely Rotating Bonds: 3; (10)Polar Surface Area: 23.31Å2; (11)Flash Point: 177.7 °C; (12)Enthalpy of Vaporization: 61.71 kJ/mol; (13)Boiling Point: 370.2 °C at 760 mmHg; (14)Vapour Pressure: 1.12E-05 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES: N3(P(N1CCCCC1)N2CCCCC2)CCCCC3
(2)InChI: InChI=1/C15H30N3P/c1-4-10-16(11-5-1)19(17-12-6-2-7-13-17)18-14-8-3-9-15-18/h1-15H2
(3)InChIKey: GEQBPMNDDHGGPJ-UHFFFAOYAX
(4)Std. InChI: InChI=1S/C15H30N3P/c1-4-10-16(11-5-1)19(17-12-6-2-7-13-17)18-14-8-3-9-15-18/h1-15H2
(5)Std. InChIKey: GEQBPMNDDHGGPJ-UHFFFAOYSA-N]

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intravenous 180mg/kg (180mg/kg)   U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. Vol. NX#02472,

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