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565881

Sigma-Aldrich

2,8,9-Triisobutyl-2,5,8,9-tetraaza-1-phosphabicyclo[3.3.3]undecane

97%

Synonym(s):

Triisobutylphosphatrane

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About This Item

Empirical Formula (Hill Notation):
C18H39N4P
CAS Number:
331465-71-5
Molecular Weight:
342.50
MDL number:
MFCD03840347
UNSPSC Code:
12352005
PubChem Substance ID:
24880262
NACRES:
NA.22

Quality Level

200

Assay

97%

refractive index

n20/D 1.5020 (lit.)

density

0.964 g/mL at 25 °C (lit.)

SMILES string

CC(C)CN1CCN2CCN(CC(C)C)P1N(CC2)CC(C)C

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

InChI key

WFHPXSHLCFHEIA-UHFFFAOYSA-N

Related Categories

Application

Ligand used in the α-arylation of nitriles with aryl bromides and chlorides, and in the Stille cross-coupling of aryl chlorides.
Together with Pd2(dba)3 (Catalog Number 328774) forms a highly efficient catalyst for one-pot syntheses of trans-4-N,N-diarylaminostilbenes and N,N-diarylaminostyrenes. Catalyst for methanolic cleavage of heteroaromatic carbamates.

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

154.9 °F - closed cup

Flash Point(C)

68.3 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
MKCG2726
MKBQ5232V
MKBL4487V
MKBG6944V
85096KJ

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Weiping Su et al.
Organic letters, 6(9), 1421-1424 (2004-04-23)
[reaction: see text] The Pd(2)(dba)(3)/P(i-BuNCH(2)CH(2))(3)N (1d) catalyst system is highly effective for the Stille cross-coupling of aryl chlorides with organotin compounds. This method represents only the second general method for the coupling of aryl chlorides. Other proazaphosphatranes possessing benzyl substituents
Tetrahedron Letters, 47, 5645-5645 (2006)
A general method for the direct alpha-arylation of nitriles with aryl chlorides.
Jingsong You et al.
Angewandte Chemie (International ed. in English), 42(41), 5051-5053 (2003-11-05)
Jingsong You et al.
The Journal of organic chemistry, 68(21), 8003-8007 (2003-10-11)
A new catalyst system for the synthesis of alpha-aryl-substituted nitriles is reported. The bicyclic triaminophosphine P(i-BuNCH(2)CH(2))(3)N (1b) serves as an efficient and versatile ligand for the palladium-catalyzed direct alpha-arylation of nitriles with aryl bromides. Using ligand 1b, ethyl cyanoacetate and
Tetrahedron, 61, 9775-9775 (2005)

Articles

Proazaphosphatranes: Verkade’s Superbases

An article on Proazaphosphatranes: Verkade’s Superbases.

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