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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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

FSL

Group 4: Flammable liquids
Type 2 petroleums
Hazardous rank III
Water insoluble liquid

JAN Code

565881-1G:
565881-BULK:
565881-VAR:
565881-5G:

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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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