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38222-83-2 - 2,6-Di-tert-butyl-4-methylpyridine, 97% - DTBMP - L14143 - Alfa Aesar

L14143 2,6-Di-tert-butyl-4-methylpyridine, 97%

CAS Number
38222-83-2
Synonyms
DTBMP

Size Price ($) Quantity Availability
1g 31.50
5g 112.00
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2,6-Di-tert-butyl-4-methylpyridine, 97%

MDL
MFCD00006305
EINECS
253-834-4

Chemical Properties

Formula
C14H23N
Formula Weight
205.35
Melting point
30-35°
Boiling Point
232-234°
Flash Point
83°(181°F)
Refractive Index
1.4765
Sensitivity
Air & Light Sensitive
Solubility
Sparingly soluble in water. Soluble in ethanol, acetic acid and diethyl ether.

Applications

2,6-Di-tert-butyl-4-methylpyridine is used for the generation of enol triflates from ketones using trifluoromethanesulfonic anhydride. It is also used in the synthesis of 1,2-dihydro-2-silanaphthalene derivatives, as base in PtCl4-catalyzed cyclization reactions of homopropargyl azide derivatives and in diastereoselective synthesis of β-thiomannopyranosides.

Notes

Store in cool place. Keep container tightly closed in a dry and well-ventilated place. Recommended storage temperature is 2 - 8°C. Store under inert gas. It is sensitive to air and light.

Literature References

D Crich.; H Li. Direct stereoselective synthesis of beta-thiomannosides. Journal of Organic Chemistry. 2000, 65 (3), 801-805.

Hidekazu Arii.; Takashi Kurihara.; Kunio Mochida.; Takayuki Kawashima.Silylium ion-promoted dehydrogenative cyclization: synthesis of silicon-containing compounds derived from alkynes. Chemical Communications. 2014, 50 (50), 6649-6652.

Sterically-hindered, non-nucleophilic base.

Recommended base for the generation of enol triflates from ketones using Trifluoromethanesulfonic anhydride, A11767: J. Org. Chem., 54, 2886 (1989). For examples, see: Org. Synth. Coll., 8, 97, 126 (1993). For comparison with other hindered bases in peptide coupling reactions, see: J. Org. Chem., 61, 2460 (1996). See also Appendix 6.

GHS Hazard and Precautionary Statements

Hazard Statements: H315-H319-H335

Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.

Precautionary Statements: P261-P280-P305+P351+P338-P304+P340-P362-P312-P321-P405-P403+P233-P501a

Avoid breathing dust/fume/gas/mist/vapours/spray. Wear protective gloves/protective clothing/eye protection/face protection. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Take off contaminated clothing and wash before reuse. Call a POISON CENTER or doctor/physician if you feel unwell. Specific treatment (see label). Store locked up. Store in a well-ventilated place. Keep container tightly closed. Dispose of contents/container in accordance with local/regional/national/international regulations.

Other References

Beilstein
130503
Harmonized Tariff Code
2933.39
TSCA
No

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