4,4'-DIMETHOXY-2,2'-BIPYRIDINE Chemical Properties

Melting point:

168-171 °C(lit.)

Boiling point:

347.6±37.0℃ (760 Torr)

Density 

1.143±0.06 g/cm3 (20 ºC 760 Torr)

refractive index 

1.6660 (estimate)

Flash point:

127.0±16.8℃

storage temp. 

Inert atmosphere,Room Temperature

form 

powder to crystal

pka

5.69±0.30(Predicted)

color 

White to Almost white

InChI

InChI=1S/C12H12N2O2/c1-15-9-3-5-13-11(7-9)12-8-10(16-2)4-6-14-12/h3-8H,1-2H3

InChIKey

IMEVSAIFJKKDAP-UHFFFAOYSA-N

SMILES

C1(C2=NC=CC(OC)=C2)=NC=CC(OC)=C1

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

HS Code 

29333990

MSDS

• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich

4,4'-DIMETHOXY-2,2'-BIPYRIDINE Usage And Synthesis

Chemical Properties

white to light yellow-beige crystalline powder

Uses

4-4′-Dimethoxy-2-2''-bipyridine may be used as a ligand in the preparation of transition metal complexes.

Ligand for greener oxidation of alcohols under aerobic conditions.

Copper(I)/ABNO-Catalyzed Aerobic Alcohol Oxidation: Alleviating Steric and Electronic Constraints of Cu/TEMPO Catalyst Systems

General Description

This product has been enhanced for catalysis.

Synthesis

General procedure for the synthesis of 4,4'-dimethoxy-2,2'-bipyridine nitride from 4,4'-dimethoxy-2,2'-bipyridine nitride: 4,4'-dimethoxy-2,2'-bipyridine 1,1'-dioxide (10) (2.50 g, 10.1 mmol), palladium carbon (5% Pd, 5.16 g, 2.42 mmol, 0.24 eq. ) and ethanol (290 mL) were refluxed for 5 min. An ethanol solution of hydrazine monohydrate (39.3 g, 0.785 mol) was added slowly and dropwise to the mixture (170 mL) over 1 hour. The reaction mixture was continued to reflux for 18 hours and then filtered through Celite. The residue on the diatomaceous earth was washed with hot ethanol. The filtrate and washings were combined, the solvent was removed by evaporation, and the residue was recrystallized from methanol to give the target product 7f (0.412 g, 19% yield). 7f was pale yellow crystals.1H NMR (300 MHz, CDCl3) δ 8.48 (d, J=5.4 Hz, 2H), 7.98 (d, J=2.4 Hz, 2H), 6.86 (dd, J=5.4 Hz, 2.4Hz, 2H), 3.96 (s, 6H).

References

[1] Journal of Organic Chemistry, 2006, vol. 71, # 1, p. 315 - 319
[2] Advanced Synthesis and Catalysis, 2003, vol. 345, # 4, p. 497 - 505
[3] Tetrahedron Letters, 2016, vol. 57, # 49, p. 5489 - 5492
[4] Journal of the American Chemical Society, 1958, vol. 80, p. 2745,2747

4,4'-DIMETHOXY-2,2'-BIPYRIDINE(17217-57-1)Related Product Information

• 6,6'-Dimethyl-2,2'-dipyridyl
• 2,2-bipyridine-6-carboxylic acid
• 4'-(9-Anthracenyl)-2,2':6',2''-terpyridine
• 2,6-BIS(2-PYRIDYL)-4(1H)-PYRIDONE
• 2,2':6',2''-TERPYRIDINE-4'-CARBALDEHYDE
• 4'-(4-BROMOPHENYL)-2,2':6',2''-TERPYRIDINE
• 2,2':6',2''-TERPYRIDINE
• 4,4'-BIS(DIHYDROXYPHOSPHORYL)-2,2'-BIPYRIDINE
• 2,2':6',2''-TERPYRIDINE-4'-CARBOXYLIC ACID
• 4,4'-DIBROMO-2,2'-BIPYRIDINE
• 4,4'-Bis(chloromethyl)-2,2'-bipyridyl
• 2,2'-Bipyridine
• 4,4'-DIMETHOXY-2,2'-BIPYRIDINE
• 4,4'-DIHYDROXY-2,2'-BIPYRIDINE
• 4-[4'-(4-AMINOMETHYLPHENOXY)-[2,2']BIPYRIDINYL-4-YLOXY]-BENZYLAMINE
• CHEMPACIFIC 38141
• 5,5'-Dimethoxy-2,2'-bipyridine
• (E)-3,4-Dimethoxy-[2,2'-bipyridine]-6-carbaldehyde oxime,(E)-3,4-Dimethoxy-2,2'-bipyridine-6-carbaldehyde oxime