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438294

Sigma-Aldrich

Tetrabutylphosphonium hydroxide solution

40 wt. % in H2O

Synonym(s):

TBPH

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About This Item

Linear Formula:
(CH3CH2CH2CH2)4P(OH)
CAS Number:
14518-69-5
Molecular Weight:
276.44
Beilstein:
4826225
MDL number:
MFCD00068456
UNSPSC Code:
12352000
PubChem Substance ID:
24867442
NACRES:
NA.22

form

liquid

concentration

40 wt. % in H2O

refractive index

n20/D 1.412

density

0.989 g/mL at 25 °C

SMILES string

[OH-].CCCC[P+](CCCC)(CCCC)CCCC

InChI

1S/C16H36P.H2O/c1-5-9-13-17(14-10-6-2,15-11-7-3)16-12-8-4;/h5-16H2,1-4H3;1H2/q+1;/p-1

InChI key

DFQPZDGUFQJANM-UHFFFAOYSA-M

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Application

Tetrabutylphosphonium hydroxide (TBPH) can be used:
  • To convert poorly water-soluble acidic APIs into TBP ionic liquids (IL).
  • As a cation source in the synthesis of Good′s buffer ionic liquids (GB-ILs) via an acid−base neutralization reaction with Good′s buffer anions.
  • To synthesize tetrabutylphosphonium acetate, which along with Cu2O-nanoparticles forms an excellent catalyst system for protodecarboxylation reactions.

Pictograms

Corrosion
GHS05

Signal Word

Danger

Hazard Statements

H314

Precautionary Statements

P280 - P305 + P351 + P338 - P310

Hazard Classifications

Skin Corr. 1B

Storage Class Code

8A - Combustible corrosive hazardous materials

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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Kazuma Ikeda et al.
Organic & biomolecular chemistry, 17(31), 7337-7341 (2019-07-25)
Factors contributing to the different distribution behaviour of cytochrome c were investigated in a biphasic tetrabutylphosphonium 2,4,6-trimethylbenzenesulfonate and potassium phosphate buffer system, which shows a lower critical solution temperature. To change charge balance and hydrophobicity of cytochrome c, surface modification
Ryan J H West et al.
Acta neuropathologica communications, 8(1), 158-158 (2020-09-08)
A large intronic hexanucleotide repeat expansion (GGGGCC) within the C9orf72 (C9orf72-SMCR8 Complex Subunit) locus is the most prevalent genetic cause of both Frontotemporal Dementia (FTD) and Motor Neuron Disease (MND). In patients this expansion is typically hundreds to thousands of
Leila Moura et al.
Chemphyschem : a European journal of chemical physics and physical chemistry, 18(23), 3384-3389 (2017-08-30)
The use of 5-phenyltetrazole, a bioisostere of benzoic acid, as an anion source to prepare an ionic liquid is described for the first time. Tetrabutylphosphonium 5-phenyltetrazolate undergoes phase separation from water with lower critical solution temperature phase behavior, in contrast
Recyclable nanoscale copper (I) catalysts in ionic liquid media for selective decarboxylative C-C bond cleavage
Kessler MT, et al.
Catalysis Science & Technology, 3(4), 992-1001 (2013)
Evaluating self-buffering ionic liquids for biotechnological applications
Lee SY, et al.
ACS sustainable chemistry & engineering, 3(12), 3420-3428 (2015)
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