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27690

Sigma-Aldrich

2,4,6-Trimethylpyridine

puriss. p.a., 99% (GC)

Synonym(s):

2,4,6-Collidine, sym-Collidine

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About This Item

Empirical Formula (Hill Notation):
C8H11N
CAS Number:
108-75-8
Molecular Weight:
121.18
Beilstein:
107283
EC Number:
203-613-3
MDL number:
MFCD00006338
UNSPSC Code:
12352100
PubChem Substance ID:
57648267
NACRES:
NA.21

grade

puriss. p.a.

Quality Level

200

Assay

99% (GC)

form

liquid

impurities

≤0.1% water

evapn. residue

≤0.1%

refractive index

n20/D 1.498 (lit.)
n20/D 1.498

bp

171-172 °C (lit.)

mp

−43 °C (lit.)

density

0.917 g/mL at 25 °C (lit.)

cation traces

Al: ≤0.5 mg/kg
Ba: ≤0.1 mg/kg
Bi: ≤0.1 mg/kg
Ca: ≤0.5 mg/kg
Cd: ≤0.05 mg/kg
Co: ≤0.02 mg/kg
Cr: ≤0.02 mg/kg
Cu: ≤0.02 mg/kg
Fe: ≤0.1 mg/kg
K: ≤0.5 mg/kg
Li: ≤0.1 mg/kg
Mg: ≤0.1 mg/kg
Mn: ≤0.02 mg/kg
Mo: ≤0.1 mg/kg
Na: ≤0.5 mg/kg
Ni: ≤0.02 mg/kg
Pb: ≤0.1 mg/kg
Sr: ≤0.1 mg/kg
Zn: ≤0.1 mg/kg

storage temp.

2-8°C

SMILES string

Cc1cc(C)nc(C)c1

InChI

1S/C8H11N/c1-6-4-7(2)9-8(3)5-6/h4-5H,1-3H3

InChI key

BWZVCCNYKMEVEX-UHFFFAOYSA-N

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General description

2,4,6-Trimethylpyridine is a heterocyclic aromatic compound that is commonly used in dehydrohalogenation reactions. It is also used as a reaction solvent or chemical additive in organic reactions due to its basic properties.

Application

2,4,6-Trimethylpyridine can be used as a reagent:      
  • In solid-phase peptide synthesis.     
  • To synthesize trichloro(2,4,6-trimethylpyridine) Au(III) complex by reacting with HAuCl4.

Tissue fixative for electron microscopy.

Pictograms

FlameSkull and crossbones
GHS02,GHS06

Signal Word

Danger

Hazard Classifications

Acute Tox. 3 Dermal - Acute Tox. 4 Oral - Aquatic Chronic 3 - Eye Irrit. 2 - Flam. Liq. 3 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

131.0 °F - closed cup

Flash Point(C)

55 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCCK8709
BCCK3944
BCCK8240
BCCJ6244
BCCG3984

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Assessing the acid properties of desilicated ZSM-5 by FTIR using CO and 2, 4, 6-trimethylpyridine (collidine) as molecular probes.
Holm MS, et al.
Applied Catalysis A: General, 356(1), 23-30 (2009)
Janet E Del Bene et al.
The journal of physical chemistry. A, 110(3), 1128-1133 (2006-01-20)
Ab initio EOM-CCSD calculations have been performed on 3:1 FH:NH3 complexes at their own optimized MP2/6-31+G(d,p) geometries and at the optimized geometries in the hydrogen-bonding regions of corresponding 3:1 FH:collidine complexes. The isolated gas-phase equilibrium 3:1 FH:NH3 complex has an
J L Tomsig et al.
Histochemistry, 89(3), 301-306 (1988-01-01)
In previous work of our laboratory it was demonstrated that collidine (2,4,6-trimethylpyridine) abolishes the core osmiophilia and chromaffin reaction from rat pinal gland and vas deferens nerves. This abolition was apparent when tissues were briefly incubated in collidine or when
Masayoshi Tsubuki et al.
The Journal of organic chemistry, 74(3), 1422-1425 (2008-12-20)
We have found that ruthenium-catalyzed cyclocarbonylation of allenyl alcohols in 2,4,6-collidine under atmospheric pressure of carbon monoxide smoothly proceeds to afford alpha,beta-unsaturated five- and six-membered lactones in moderate to good yields. Furthermore, we have completed a highly stereoselective synthesis of
W G Dauben et al.
Carbohydrate research, 203(1), 47-56 (1990-08-01)
The yields of disaccharide glycosylation products in tetramethylammonium bromide or silver triflate-collidine activated reactions between hindered alcohols and glycosyl halides were not greatly ++affected when a pressure of 15 kbar was applied. The formation of orthoester products was greatly increased
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