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249505

Sigma-Aldrich

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

98%

Synonym(s):

2,6-Bis(1,1-dimethylethyl)-4-methylpyridine, 2,6-Bis(tert-butyl)-4-methylpyridine, 2,6-Ditert-butyl-4-methylpyridine, 4-Methyl-2,6-di-tert-butylpyridine

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About This Item

Empirical Formula (Hill Notation):
C14H23N
CAS Number:
38222-83-2
Molecular Weight:
205.34
Beilstein:
130503
EC Number:
253-834-4
MDL number:
MFCD00006305
UNSPSC Code:
12352100
PubChem Substance ID:
24855001
NACRES:
NA.22
Pricing and availability is not currently available.

Assay

98%

form

solid

refractive index

n20/D 1.4763 (lit.)

bp

233 °C (lit.)

mp

33-36 °C (lit.)

solubility

ethanol: soluble 5%, clear to slightly hazy, colorless to dark yellow

storage temp.

2-8°C

SMILES string

Cc1cc(nc(c1)C(C)(C)C)C(C)(C)C

InChI

1S/C14H23N/c1-10-8-11(13(2,3)4)15-12(9-10)14(5,6)7/h8-9H,1-7H3

InChI key

HVHZEKKZMFRULH-UHFFFAOYSA-N

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General description

2,6-Di-tert-butyl-4-methylpyridine is a sterically hindered, non-nucleophilic base which distinguishes between BrÖnsted (protonic) and Lewis acids. It also enables the direct high-yield conversion of aldehydes[1] and ketones[1][2] to vinyl triflates. It inhibits desilylation and hydration of the products during GaCl3-catalyzed ortho-ethynylation of phenol[3].

Application

2,6-Di-tert-butyl-4-methylpyridine has been used:
  • in the synthesis of 1,2-dihydro-2-silanaphthalene derivatives[4]
  • as base in PtCl4-catalyzed cyclization reactions of homopropargyl azide derivatives[5]
  • diastereoselective synthesis of β-thiomannopyranosides[6]

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302,H315,H319,H335

Hazard Classifications

Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

183.2 °F - closed cup

Flash Point(C)

84 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCCG6911
BCCG4356
BCCG2181
BCBN5979V
BCBN3608V

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D Crich et al.
The Journal of organic chemistry, 65(3), 801-805 (2000-05-18)
A highly diastereoselective synthesis of beta-thiomannopyranosides is described in which S-phenyl 2,3-di-O-benzyl-4, 6-O-benzylidene-1-deoxy-1-thia-alpha-D-mannopyranoside S-oxide is treated with triflic anhydride and 2, 6-di-tert-butyl-4-methylpyridine in CH(2)Cl(2) at -78 degrees C leading to the formation of an intermediate alpha-mannosyl triflate. Addition of primary
Katsumi Kobayashi et al.
Journal of the American Chemical Society, 124(29), 8528-8529 (2002-07-18)
Phenols are ethynylated at the ortho position with silylated chloroethyne in the presence of a catalytic amount of GaCl3 and lithium phenoxide. The lithium salt is essential for the catalysis, and addition of 2,6-di(tert-butyl)-4-methylpyridine inhibits desilylation and hydration of the
Synthesis, 283-283 (1980)
Organic Syntheses, 68, 138-138 (1990)
Hidekazu Arii et al.
Chemical communications (Cambridge, England), 50(50), 6649-6652 (2014-05-16)
Treatment of dialkylbenzylsilane (1) with trityl tetrakis(pentafluorophenyl)borate (TPFPB) in the presence of terminal or internal alkynes (3) and 2,6-di-tert-butyl-4-methylpyridine gave the corresponding 1,2-dihydro-2-silanaphthalene derivatives (4) in 34-82% yields.
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Questions

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  1. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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  2. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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