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549967

Sigma-Aldrich

2,4,6-Tri-tert-butylpyrimidine

97%

Synonym(s):

2,4,6-Tris(1,1-dimethylethyl)pyrimidine

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About This Item

Empirical Formula (Hill Notation):
C16H28N2
CAS Number:
67490-21-5
Molecular Weight:
248.41
MDL number:
MFCD03094045
UNSPSC Code:
12352100
PubChem Substance ID:
24874736
NACRES:
NA.22

Quality Level

100

assay

97%

mp

77-80 °C (lit.)

SMILES string

CC(C)(C)c1cc(nc(n1)C(C)(C)C)C(C)(C)C

InChI

1S/C16H28N2/c1-14(2,3)11-10-12(15(4,5)6)18-13(17-11)16(7,8)9/h10H,1-9H3

InChI key

VYWSYEDVFVGRGG-UHFFFAOYSA-N

Related Categories

General description

2,4,6-Tri-tert-butylpyrimidine (TTBP) is a non-hygroscopic sterically hindered base. It can be prepared by the reaction between tert-butyl methyl ketone and tert-butyronitrile.3 TTBP is a suitable alternative to 2,6-di-tert-butylated pyridines in glycosylation reactions.

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

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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1-Benzenesulfinyl piperidine/trifluoromethanesulfonic anhydride: a potent combination of shelf-stable reagents for the low-temperature conversion of thioglycosides to glycosyl triflates and for the formation of diverse glycosidic linkages.
Crich D and Smith M.
Journal of the American Chemical Society, 123(37), 9015-9020 (2001)
2, 4, 6-Tri-tert-butylpyrimidine (TTBP): A cost effective, readily available alternative to the hindered base 2, 6-di-tert-butylpyridine and its 4-substituted derivatives in glycosylation and other reactions.
Crich D, et al.
Synthesis, 2001(02), 0323-0326 (2001)
On the mechanism of the reaction between ketones and trifluoromethanesulfonic anhydride. An improved and convenient method for the preparation of pyrimidines and condensed pyrimidines.
Garcia Martinez A, et al.
The Journal of Organic Chemistry, 57(5), 1627-1630 (1992)

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