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13954

Sigma-Aldrich

Benzyltributylammonium bromide

≥99.0%

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Synonym(s):
Benzyltri-n-butylammonium bromide, Tributylbenzylammonium bromide
Linear Formula:
C6H5CH2N(Br)(CH2CH2CH2CH3)3
CAS Number:
25316-59-0
Molecular Weight:
356.38
Beilstein:
3776294
EC Number:
246-819-9
MDL number:
MFCD00011848
UNSPSC Code:
12352116
PubChem Substance ID:
57647124
NACRES:
NA.22

Quality Level

200

Assay

≥99.0%

form

solid

mp

169-175 °C

SMILES string

[Br-].CCCC[N+](CCCC)(CCCC)Cc1ccccc1

InChI

1S/C19H34N.BrH/c1-4-7-15-20(16-8-5-2,17-9-6-3)18-19-13-11-10-12-14-19;/h10-14H,4-9,15-18H2,1-3H3;1H/q+1;/p-1

InChI key

UDYGXWPMSJPFDG-UHFFFAOYSA-M

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Application

Benzyltributylammonium bromide can be used:
  • As a phase transfer catalyst in the isomerization reactions of cis-4-formyl-2-azetidinones.
  • As a hydrogen-bond acceptor in the preparation of deep eutectic solvents, which are used in the isolation of lysozyme from the chicken egg white.
  • In the phase transfer glycosylation of novobiocin to yield glucosyl-novobiocin.

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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Regioselective glycosylation of novobiocin alters activity
Sun G, et al.
Carbohydrate Research, 452(11), 116-121 (2017)
Development of deep eutectic solvent-based aqueous biphasic system for the extraction of lysozyme
Xu P, et al.
Talanta, 202(11), 1-10 (2019)
Base-Promoted Isomerization of cis-4-Formyl-2-azetidinones: Chemoselective C 4-Epimerization vs Rearrangement to Cyclic Enaminones
Alcaide B, et al.
The Journal of Organic Chemistry, 65(11), 3453-3459 (2000)
Harish Babu Balaraman et al.
International journal of biological macromolecules, 146, 253-262 (2020-01-10)
The present research investigates on task-specific deep eutectic solvents (TDES) based aqueous two-phase extraction and purification of immunoglobulins by chromatography from quail egg. The synthesis of TDES was accomplished with quaternary ammonium salt as hydrogen bond acceptor (HBA) and glycerol
F G Riddell et al.
Journal of inorganic biochemistry, 55(4), 279-293 (1994-09-01)
One major problem in using NMR to study halide ions in biological and model biological systems has been to find a contrast reagent to differentiate between halide ions in different compartments. Mn2+ is shown to be a very efficient NMR

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