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Merck

268100

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:
5574-97-0
Molecular Weight:
339.45
UNSPSC Code:
12352103
NACRES:
NA.22
PubChem Substance ID:
24856262
MDL number:
MFCD00064526
Beilstein/REAXYS Number:
5196532

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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

SMILES string

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

InChI key

ARRNBPCNZJXHRJ-UHFFFAOYSA-M

Quality Level

200

form

liquid

concentration

1.0 M in H2O

density

1.037 g/mL at 25 °C

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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

12 - Non Combustible Liquids

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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Certificates of Analysis (COA)

Lot/Batch Number
BCCN7404
BCCN6407
BCCN6221
BCCN3129
BCCN3128

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Journal of Chromatographic Science, 31, 231-231 (1993)
Journal of Liquid Chromatography, 15, 2487-2487 (1992)
Tetrahedron, 62, 10237-10237 (2006)
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)
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