2,6-di-tert-butyl-4-methylpyridine

• ChemBase ID: 88811
• Molecular Formular: C14H23N
• Molecular Mass: 205.33912
• Monoisotopic Mass: 205.18304974
• SMILES: n1c(cc(cc1C(C)(C)C)C)C(C)(C)C
• Canonical SMILES: Cc1cc(nc(c1)C(C)(C)C)C(C)(C)C
• InChI: InChI=1S/C14H23N/c1-10-8-11(13(2,3)4)15-12(9-10)14(5,6)7/h8-9H,1-7H3
• InChIKey: HVHZEKKZMFRULH-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2,6-di-tert-butyl-4-methylpyridine
• IUPAC Traditional name: 2,6-di-tert-butyl-4-methylpyridine
• Synonyms: DTBMP; 2,6-Bis(tert-butyl)-4-methylpyridine; 2,6-Di-tert-butyl-4-methylpyridine; 2,6-Di-tert-butyl-4-methylpyridine; 2,6-Di-tert-butyl-4-methylpyridine; 2,6-二叔丁基-4-甲基吡啶; 2,6-二-叔-丁基-4-甲基吡啶

Database IDs

• CAS Number: 38222-83-2
• EC Number: 253-834-4
• MDL Number: MFCD00006305
• Beilstein Number: 130503
• PubChem SID: 24861524; 24855001; 162075716
• PubChem CID: 98898

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 4.327411
• LogD (pH = 7.4): 5.1005545
• Log P: 5.130808
• Molar Refractivity: 65.5301 cm^3
• Polarizability: 25.817757 Å^3
• Polar Surface Area: 12.89 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Apperance: brown
• Melting Point: 30-35°C; 33-36 °C(lit.); 33-36°C
• Boiling Point: 232-234°C; 233 °C(lit.); 233°C
• Flash Point: 183.2 °F; 83°C(181°F); 84 °C; 84°C
• Refractive Index: 1.4765; n20/D 1.4763(lit.)

Safety Information

• Storage Warning: Air & Light Sensitive; Harmful/Air Sensitive/Light Sensitive
• European Hazard Symbols: Irritant (Xi); Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22-36/37/38; 36/37/38
• Safety Statements: 26; 26-37
• TSCA Listed: 否
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H315-H319-H335; H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥97.0% (GC); 97%; 98%
• Grade: purum
• Empirical Formula (Hill Notation): C14H23N

DETAILS

Sigma Aldrich - 249505

Packaging
1, 5, 25 g in glass bottle
Application
A sterically hindered, non-nucleophilic base which distinguishes between Br?nsted (protonic) and Lewis acids. Enables the direct high-yield conversion of aldehydes1 and ketones1,2 to vinyl triflates.

Sigma Aldrich - 34775

Other Notes
Hindered base for glycosidations following a modified Koenigs-Knorr reaction 1,2,3; Base for the conversion of carbonyls in vinyl triflates with triflic anhydrides 4
Physical form
filled as molten mass

REFERENCES

• 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.