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268100

Sigma-Aldrich

Tetrabutylammonium phosphate monobasic solution

1.0 M in H2O

Synonym(s):

Tetrabutylammonium dihydrogen phosphate

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About This Item

Linear Formula:
(CH3CH2CH2CH2)4N[OP(OH)2O]
CAS Number:
Molecular Weight:
339.45
Beilstein:
5196532
MDL number:
UNSPSC Code:
12352103
PubChem Substance ID:
NACRES:
NA.22

Quality Level

concentration

1.0 M in H2O

density

1.037 g/mL at 25 °C

SMILES string

OP(O)([O-])=O.CCCC[N+](CCCC)(CCCC)CCCC

InChI

1S/C16H36N.H3O4P/c1-5-9-13-17(14-10-6-2,15-11-7-3)16-12-8-4;1-5(2,3)4/h5-16H2,1-4H3;(H3,1,2,3,4)/q+1;/p-1

InChI key

ARRNBPCNZJXHRJ-UHFFFAOYSA-M

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General description

Tetrabutylammonium phosphate monobasic solution (TABP) is a quaternary ammonium salt commonly used in the preparation of buffers and ion-pairing reagents.

Application

Tetrabutylammonium phosphate monobasic solution can be used as a:
  • Catalyst for the selective N-alkylation of indoles with electron-poor alkenes.
  • Hydrogen-bond-acceptor (HBA) catalyst to synthesize ketoesters via αC-H bond activation.

Storage Class Code

12 - Non Combustible Liquids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Journal of Chromatographic Science, 31, 231-231 (1993)
Journal of Liquid Chromatography, 15, 2487-2487 (1992)
Photoredox-Catalyzed Isomerization of Highly Substituted Allylic Alcohols by C- H Bond Activation
Guo K, et al.
Angewandte Chemie (International Edition in English), 59, 11660-11668 (2020)
Weak Nucleophiles in the Aza-Michael Reaction
Rulev A
Advanced Synthesis & Catalysis, 365, 1908-1925 (2023)
Tetrahedron, 62, 10237-10237 (2006)

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