2,2':6',2''-TERPYRIDINE Chemical Properties

Melting point:

90-93 °C

Boiling point:

370 °C

Density 

1.1901 (rough estimate)

refractive index 

1.5610 (estimate)

storage temp. 

Sealed in dry,Room Temperature

solubility 

dioxane: 0.1 g/mL, clear

form 

Crystalline powder

pka

4.60±0.10(Predicted)

color 

Cream to yellow to brown

Water Solubility 

1.472g/L(24.99 ºC)

BRN 

11199

InChIKey

DRGAZIDRYFYHIJ-UHFFFAOYSA-N

CAS DataBase Reference

1148-79-4(CAS DataBase Reference)

EPA Substance Registry System

2,2':6',2''-Terpyridine (1148-79-4)

Safety Information

Hazard Codes 

T+,T

Risk Statements 

27/28-37/38-41

Safety Statements 

26-28-36/37/39-45

RIDADR 

UN 2811 6.1/PG 1

WGK Germany 

3

TSCA 

Yes

HazardClass 

6.1

PackingGroup 

I

HS Code 

29333990

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

2,2':6',2''-TERPYRIDINE Usage And Synthesis

Application in coordination chemistry

As an NNN-tridentate ligand, the 2,2′:6′,2″-terpyridine plays an important role in coordination chemistry. With three coordination sites and low LUMO, terpyridine and its derivatives are one of the typical Pincer ligand and/or non-innocent ligands in transition metal catalysis. Interesting catalytic reactivities have been obtained with these tpy-metal complexes targeting some challenging transformations, such as C–C bond formation and hydrofunctionalization. The 2,2':6':2''-terpyridine ligand has literally shaped the coordination chemistry of transition metal complexes in a plethora of fields.

Description

A case of occupational dermatitis was reported in a chemical technician, with no cross reactivity to pyridine derivatives.

Chemical Properties

Off-white crystal

Uses

2,2';6',2"-terpyridine is widely utilized in the field of supramolecular chemistry, which is used to manufacture the racks, ladders and grids, helicates, catenanes and dendrimers. It plays an important role as a ligand in coordination chemistry. Its complexes are employed in the oxidation of alcohols, the carbonylation of aromatic compounds and as oxygen-binding molecules. Functionalized terpyridine ligands were used in semiconductors and solar panels. It forms chealate complexes with europium(III) and terbium(III), which is used in protein labelling.

Definition

ChEBI: A tridentate heterocyclic ligand that binds metals at three meridional sites giving two adjacent 5-membered MN2C2 chelate rings.

Synthesis Reference(s)

Journal of the American Chemical Society, 103, p. 3585, 1981 DOI: 10.1021/ja00402a062
Organic Syntheses, Coll. Vol. 7, p. 476, 1990

General Description

2,2′:6′,2′′;-Terpyridine is a tridentate ligand that can be prepared in two steps starting from 2-acetylpyridine.

Contact allergens

This molecule is a terpyridine with a 4-methyl substitution. A case of occupational dermatitis was reported in a chemical technician with no cross-reactivity to pyridine derivatives.

Purification Methods

Crystallise it from diethyl ether, toluene or from pet ether, then aqueous MeOH, followed by sublimation in a vacuum at 90o. It is used for estimating Ag and Ru. [Kamra et al. Anal Chim Acta 81 177 1976, Beilstein 26 III/IV 258.]

2,2':6',2''-TERPYRIDINE(1148-79-4)Related Product Information

• [2,2':6',2''-TERPYRIDINE]-3',4'-DICARBOXYLIC ACID
• 2,2':6',2''-TERPYRIDINE
• 4'-CHLORO-2,2':6',2''-TERPYRIDINE,4'-CHLORO-2,2'6'2''-TERPYRIDINE
• 4,4',4''-TRI-TERT-BUTYL-2,2':6',2''-TERPYRIDINE
• 1,6-DIHYDRO-[3,2':4',3'']-TERPYRIDINE
• 6''-CHLORO-[3,2':5',3'']-TERPYRIDINE
• DICHLORO(2 2':6' 2''-TERPYRIDINE)-
• 2,2':6',2''-TERPYRIDINE-4'-CARBOXYLIC ACID
• 4',4''''-(1,4-PHENYLENE)BIS(2,2':6',2''-TERPYRIDINE)
• 6,6''-DIBROMO-2,2':6',2''-TERPYRIDINE,6,6-DIBROMO-2,2:6,2-TERPYRIDINE
• 6,6''-DIMETHYL-[2,2':6',2''-TERPYRIDINE]-4'-CARBOXYLIC ACID ETHYL ESTER
• 5,5''-DIMETHYL-[2,2':6',2''-TERPYRIDINE]-4'-CARBOXYLIC ACID
• 4'-(4-NITROPHENYL)-2,2':6',2''-TERPYRIDINE
• 4'-PHENYL-2,2':6',2''-TERPYRIDINE
• 5,5''-DIMETHYL-[2,2':6',2''-TERPYRIDINE]-4'-CARBOXYLIC ACID ETHYL ESTER
• ETHYL 2,2':6',2''-TERPYRIDINE-4'-CARBOXYLATE
• [2,2':6',2''-TERPYRIDINE]-4'-CARBOXYLIC ACID BUTYL ESTER
• 5-METHYL-4'-NITRO-2,2':6',2''-TERPYRIDINE