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90660

Sigma-Aldrich

Tribenzylamine

≥99.0% (NT)

Synonym(s):

TBA

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About This Item

Linear Formula:
(C6H5CH2)3N
CAS Number:
620-40-6
Molecular Weight:
287.40
Beilstein:
2214682
EC Number:
210-638-3
MDL number:
MFCD00004773
UNSPSC Code:
12352100
PubChem Substance ID:
57653401
NACRES:
NA.22

Assay

≥99.0% (NT)

form

powder

mp

91-94 °C (lit.)

SMILES string

C(N(Cc1ccccc1)Cc2ccccc2)c3ccccc3

InChI

1S/C21H21N/c1-4-10-19(11-5-1)16-22(17-20-12-6-2-7-13-20)18-21-14-8-3-9-15-21/h1-15H,16-18H2

InChI key

MXHTZQSKTCCMFG-UHFFFAOYSA-N

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Application

Tribenzylamine (TBA) is a tertiary amine which can be used :
  • As a nitrogen group source for the reactions involving C−N bond formation.
  • For the synthesis of imine i.e. N−benzylidene benzylamine by aerobic oxidative condensation.
  • As an extractant for the separation and determination of Cr(VI) and Cr(III) from wastewater.

TBA can also undergo debenzylation in the presence of ceric ammonium nitrate (CAN) to form dibenzylamine.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H317

Hazard Classifications

Skin Sens. 1

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

399.2 °F - closed cup

Flash Point(C)

204 °C - closed cup

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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Céline Burnier et al.
Talanta, 192, 135-141 (2018-10-24)
Nowadays, Gas Chromatography Mass Spectrometry (GC-MS) is mainly used in forensic sciences but suffers from limitations when the analysed compounds are thermally instable as it is the case for THC-A (Tetrahydrocannabinolic Acid) which is converted into Δ9-THC (Δ9-Tetrahydrocannabinol) that subsequently
Chemoselective oxidative debenzylation of tertiary N-benzyl amines.
Bull SD, et al.
Chemical Communications (Cambridge, England), 165(5), 337-338 (2000)
Highly active and selective gold catalysts for the aerobic oxidative condensation of benzylamines to imines and one-pot, two-step synthesis of secondary benzylamines.
Grirrane A, et al.
J. Catal., 264(2), 138-144 (2009)
Copper-Catalyzed Oxidative Amination of Benzoxazoles via C- H and C- N Bond Activation: A New Strategy for Using Tertiary Amines as Nitrogen Group Sources.
Guo S, et al.
Organic Letters, 13(3), 522-525 (2010)
Najat S Khan et al.
The Journal of organic chemistry, 76(5), 1418-1424 (2011-01-29)
A gyroscope-inspired tribenzylamine hemicryptophane provides a vehicle for exploring the structure and properties of multiple p-phenylene rotators within one molecule. The hemicryptophane was synthesized in three steps in good overall yield using mild conditions. Three rotator-forming linkers were cyclized to
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