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241970

Sigma-Aldrich

Tetrapentylammonium bromide

≥99%

Synonym(s):

Tetra-n-pentylammonium bromide

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About This Item

Linear Formula:
[CH3(CH2)4]4N(Br)
CAS Number:
866-97-7
Molecular Weight:
378.47
Beilstein/REAXYS Number:
3658171
EC Number:
212-756-0
MDL number:
MFCD00011856
UNSPSC Code:
12352116
PubChem Substance ID:
24854524
NACRES:
NA.22

Quality Level

100

assay

≥99%

mp

100-101 °C (lit.)

SMILES string

[Br-].CCCCC[N+](CCCCC)(CCCCC)CCCCC

InChI

1S/C20H44N.BrH/c1-5-9-13-17-21(18-14-10-6-2,19-15-11-7-3)20-16-12-8-4;/h5-20H2,1-4H3;1H/q+1;/p-1

InChI key

SPALIFXDWQTXKS-UHFFFAOYSA-M

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General description

Tetrapentylammonium bromide is a quaternary ammonium salt with pentyl chains and a bromide counterion, which is generally used as a phase transfer catalyst.

Application

Tetrapentylammonium bromide can be used:
  • As a versatile structure-directing agent for the synthesis of Zeolite-like heterobimetallic cyanide frameworks.
  • As an alkylating agent for rhodium(I)-catalyzed alkylation reaction of benzylic amines and for N-alkylation of azaheterocycles.
  • As a precursor to prepare a Cobalt-complex, {[(Pentyl)4N]3CoBr3}Cl2, which is used as a catalyst in the synthesis of multiwalled carbon nanotubes (MWCNTs).


Electrochemical synthesis of stable graphite intercalation compounds (GICs) containing tetrapentylammonium cations has been reported.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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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Quaternary Ammonium Salts as Alkylating Reagents in C-H Activation Chemistry.
Spettel M, et al.
Organic Letters, 19(16), 4287-4290 (2017)
Chemical modification of polymers via phase transfer catalysis
Nishikubo T.
Handbook of Phase Transfer Catalysis, 480-509 (1997)
Novel catalyst based on Co-complex to prepare MWCNT.
Alonso-Nu?ez G, et al.
Materials Letters, 109, 163-166 (2013)
Quaternary ammonium salts as highly efficient and green alkylating agents for N-alkylation of azaheterocycles under microwave irradiation.
Khalafi-Nezhad A, et al.
Journal of the Iranian Chemical Society, 5(1), S40-S46 (2008)
The electrochemical synthesis of the graphite intercalation compounds containing tetra-n-alkylammonium cations.
Sirisaksoontorn W and Lerner MM.
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