2,8,9-Triisobutyl-2,5,8,9-tetraaza-1-phosphabicyclo(3.3.3)undecane (HCID 4571243)

Names & identifiers

Preferred name: 2,8,9-Triisobutyl-2,5,8,9-tetraaza-1-phosphabicyclo(3.3.3)undecane
IUPAC: 2,8,9-tris(2-methylpropyl)-2,5,8,9-tetraza-1-phosphabicyclo[3.3.3]undecane
English name: 2,8,9-Tri-i-butyl-2,5,8,9-tetraaza-1-phosphabicyclo[3.3.3]undecane
Molecular formula: C18H39N4P
Molecular weight: 342.5

Names & synonyms

2,8,9-Triisobutyl-2,5,8,9-tetraaza-1-phosphabicyclo[3.3.3]undecaneTriisobutylazaphosphatraneTriisobutylproazaphosphatraneX79X7GNS8K2,8,9-Tris(2-methylpropyl)-2,5,8,9-tetraaza-1-phosphabicyclo[3.3.3]undecaneTriisobutyl-verkade's superbase [MI]DTXSID904043762,8,9-Triisobutyl-2,5,8,9-tetraaza-1-phosphabicyclo(3.3.3)undecane2,8,9-Tris(2-methylpropyl)-2,5,8,9-tetraaza-1-phosphabicyclo(3.3.3)undecane2,5,8,9-Tetraaza-1-phosphabicyclo(3.3.3)undecane, 2,8,9-tris(2-methylpropyl)-4,6,11-Tris(2-methylpropyl)-1,4,6,11-tetraza-5-phosphabicyclo(3.3.3)undecaneRefChem:197476

Show more names

2,8,9-TRIISOBUTYL-2,5,8,9-TETRA AZA-1-P&Tri-i-butyl-tetraaza-1-phosphabicyclo-undecane2,8 9-TRI-I-BUTYL-2,5,8 9-TETRAAZA-1-PHOSPHABICYCLO[3.3.3]UNDECANE2,8,9-Triisobutyl-2,5,8,9-tetraaza-1-phosphabicyclo[3.3.3]undecane 97%2,8,9-Triisobutyl-2,5,8,9-tetraaza-1-phosphabicyclo[3.3.3]undecane,97%2,8,9-Tri-i-butyl-2,5,8,9-tetraaza-1-phosphabicyclo[3.3.3]undecane,97%

DTXCID10355230TRIISOBUTYL-VERKADE'S SUPERBASE812-117-1331465-71-5TriisobutylphosphatraneMFCD038403472,8,9-tris(2-methylpropyl)-2,5,8,9-tetraza-1-phosphabicyclo[3.3.3]undecane2,8,9-tri-i-butyl-2,5,8,9-tetraaza-1-phosphabicyclo[3.3.3]undecane

Database identifiers

CAS: 331465-71-5
PubChem CID: 4571243
DTXSID: DTXSID90404376
UNII: X79X7GNS8K
EC Number: 812-117-1
Nikkaji: J1.408.778H

Properties

Computed structural properties

XLogP: 4.2
Topological polar surface area: 13 Å²
Hydrogen bond donors: 0
Hydrogen bond acceptors: 4
Rotatable bonds: 6
Heavy atoms: 23
Formal charge: 0
Complexity: 296

Experimental & physicochemical properties

Ionization Efficiency · 6 items

Positive

5.04

2.7

Agilent XCT

Electrospray ionization

formic acid (5.3nM)

Physicochemical properties

Boiling point: 397.4 · 397.4±41.0 °C(Predicted)
Density: 0.964 g/mL · 0.964 g/mL at 25 °C(lit.)
refractive index: 20 · n20/D 1.5020(lit.)
Flash point: 155 °F · 155 °F
storage temp.: 2 · under inert gas (nitrogen or Argon) at 2-8°C
pka: 8.9 · 8.90±0.20(Predicted)
form: Liquid
color: Clear colorless to yellow
Sensitive: air sensitive, moisture sensitive
InChI: 1S/C18H39N4P/c1-16(2)13-20-10-7-19-8-11-21(14-17(3)4)23(20)22(12-9-19)15-18(5)6/h16-18H,7-15H2,1-6H3
InChIKey: WFHPXSHLCFHEIA-UHFFFAOYSA-N
SMILES: CC(C)CN1CCN2CCN(CC(C)C)P1N(CC2)CC(C)C
FDA UNII: 79 X7GNS8K · X79X7GNS8K
UNSPSC Code: 12352005 · 12352005
NACRES: 22 · NA.22
Symbol(GHS): 2 · GHS02,GHS07
Signal word: Danger
Hazard statements: 225 · H225-H302-H319-H336
Precautionary statements: 210 · P210-P261-P305+P351+P338
PPE: Eyeshields, Gloves, multi-purpose combination respirator cartridge (US)
Hazard Codes: F,Xn
Risk Statements: 36 · 36/37/38-67-66-22-19-11
Safety Statements: 26 · 26-36/37/39-16
RIDADR: 1155 · UN1155 - class 3 - PG 1 - Diethyl ether
WGK Germany: 3 · 3
HS Code: 29310099 · 29310099
Storage Class: 10 · 10 - Combustible liquids

Safety & regulation

GHS classification

GHS Classification · 4 items

Warning

H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]

P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.

Safety data

PPE: Eyeshields, Gloves, multi-purpose combination respirator cartridge (US)
wgk: 3
ridadr: UN1155 - class 3 - PG 1 - Diethyl ether
hs_code: 29310099
risk_code: 36/37/38-67-66-22-19-11
Signal word: Danger
Symbol(GHS): GHS02,GHS07
hazard_code: F,Xn
safety_code: 26-36/37/39-16
Storage Class: 10 - Combustible liquids
Hazard statements: H225-H302-H319-H336
Precautionary statements: P210-P261-P305+P351+P338

Chemistry & industry

Applications

UsesExceedingly strong, non-ionic Brønsted and Lewis base useful in a variety of organic transformations.

UsesTriisobutylazaphosphatrane is reported to be used as a catalyst for the preparation of biaryl and alkenylarenes via Stille cross-coupling reaction. It also acts a catalyst for the synthesis of α-aryl-substituted nitriles.