135822-72-9

Basic information

• Product Name: 2,2'-BIPYRIDYL-5,5'-DIALDEHYDE
• Synonyms: 2,2'-BIPYRIDYL-5,5'-DIALDEHYDE;2,2'-BIPYRIDIL-5,5'-DIALDEHYDE;2,2'-Bipyridine-5,5'-dicarboxaldehyde;[2,2,-bipyridine]-5,5,-dicarbaldehyde;6-(5-formylpyridin-2-yl)pyridine-3-carbaldehyde
• CAS NO: 135822-72-9
• Molecular Formula: C₁₂H₈N₂O₂
• Molecular Weight: 212.2
• EINECS: 1592732-453-0
• Mol File: 135822-72-9.mol
• Article Data: 12

Chemical Properties

• Melting Point: 227-229 °C
• Boiling Point: 423.4±45.0 °C(Predicted)
• Appearance: /
• Density: 1.289±0.06 g/cm3(Predicted)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 2.16±0.32(Predicted)
• CAS DataBase Reference: 2,2'-BIPYRIDYL-5,5'-DIALDEHYDE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2'-BIPYRIDYL-5,5'-DIALDEHYDE(135822-72-9)
• EPA Substance Registry System: 2,2'-BIPYRIDYL-5,5'-DIALDEHYDE(135822-72-9)

Safety Data

• Hazardous Substances Data: 135822-72-9(Hazardous Substances Data)

Usage

General Description

2,2'-Bipyridyl-5,5'-dialdehyde is a chemical compound with the molecular formula C12H8N2O2. It is a derivative of bipyridine and is commonly used as a building block in the synthesis of various organic compounds and coordination complexes. 2,2'-BIPYRIDYL-5,5'-DIALDEHYDE is known for its ability to form chelating complexes with metal ions, making it useful in various fields such as coordination chemistry, catalysis, and material science. It has also been studied for its potential applications in sensors, fluorescent probes, and organic light-emitting diodes. Its unique properties and reactivity make it a versatile and important compound in the field of organic and inorganic chemistry.

Synthetic route

2-isopropyl-1,2-dihydro-[2,2']bipyridinyl-5,5'-dicarbaldehyde → 2-hydroperoxypropane (3031-75-2) + 2,2′-bipyridine-5,5′-dicarbaldehyde (135822-72-9)

Conditions	Yield
With air In dichloromethane at 20℃;	A n/a B 99%

(1E,1'E)-2,2'-([2,2'-bipyridine]-5,5'-diyl)bis(N,N-dimethylethen-1-amine) → 2,2′-bipyridine-5,5′-dicarbaldehyde (135822-72-9)

Conditions	Yield
With sodium periodate In tetrahydrofuran; dichloromethane; water at 20℃;	73%
With sodium periodate In tetrahydrofuran; dichloromethane; water at 20℃; for 20h;	72%
With sodium periodate In tetrahydrofuran; dichloromethane; water at 20℃; for 20h;	70%
With sodium periodate In tetrahydrofuran; dichloromethane; water at 20℃; for 20h;	70%

(2-(4′-(2-dimethylaminovinyl)-(2,2′)-bipyridinyl-4-yl)vinyl)dimethylamine → 2,2′-bipyridine-5,5′-dicarbaldehyde (135822-72-9)

Conditions	Yield
With sodium periodate In tetrahydrofuran; dichloromethane; water at 20℃; for 20h;	72%
With sodium periodate In tetrahydrofuran; dichloromethane; water at 20℃; for 22h; Inert atmosphere;	60%
With sodium periodate In tetrahydrofuran; water

4,4′-bis(hydroxymethyl)-2,2′-bipyridine (63361-65-9) → 2,2′-bipyridine-5,5′-dicarbaldehyde (135822-72-9)

Conditions	Yield
With Dess-Martin periodane In dichloromethane at 20℃; for 1h; Inert atmosphere;	63%
With pyridine; lead(IV) acetate at 90℃; for 2h;	15 % Chromat.

5,5'-bis(bromomethyl)-2,2'-bipyridine (92642-09-6) → 2,2′-bipyridine-5,5′-dicarbaldehyde (135822-72-9)

Conditions	Yield
With sodium hydrogencarbonate; dimethyl sulfoxide at 115℃; for 3.5h;	49%
With hexamethylenetetramine In ethanol; water for 60h;

5,5'-Bis(carboxyethyl)-2,2'-bipyridine (153305-75-0) → 2,2′-bipyridine-5,5′-dicarbaldehyde (135822-72-9)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: NaBH4 / ethanol / Heating 1.2: acetone / 1 h / Heating 1.3: aq. K2CO3 / 1 h / Heating 2.1: 15 percent Chromat. / pyridine; Pb(CH3CO2)4 / 2 h / 90 °C View Scheme

5,5'-dimethyl-2,2'-bipyridine (1762-34-1) → 2,2′-bipyridine-5,5′-dicarbaldehyde (135822-72-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: N,N-dimethyl-formamide 2: sodium periodate / tetrahydrofuran; water View Scheme
Multi-step reaction with 2 steps 1: N-Bromosuccinimide; dibenzoyl peroxide / tetrachloromethane / 14 h / Inert atmosphere; Reflux 2: hexamethylenetetramine / water; ethanol / 60 h View Scheme
Multi-step reaction with 2 steps 1: N,N-dimethyl-formamide / 72 h / 120 °C / Inert atmosphere 2: sodium periodate / dichloromethane; tetrahydrofuran; water / 22 h / 20 °C / Inert atmosphere View Scheme

2,2'-bipyridine-5,5'-dicarboxylic acid (1802-30-8) → 2,2′-bipyridine-5,5′-dicarbaldehyde (135822-72-9)

Conditions	Yield
Multi-step reaction with 3 steps 1: sulfuric acid / 16 h / Reflux; Inert atmosphere 2: sodium tetrahydroborate / ethanol / 4 h / Reflux; Inert atmosphere 3: Dess-Martin periodane / dichloromethane / 1 h / 20 °C / Inert atmosphere View Scheme

[2,2']bipyridinyl-5,5'-dicarboxylic acid diethyl ester (1762-46-5) → 2,2′-bipyridine-5,5′-dicarbaldehyde (135822-72-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium tetrahydroborate / ethanol / 4 h / Reflux; Inert atmosphere 2: Dess-Martin periodane / dichloromethane / 1 h / 20 °C / Inert atmosphere View Scheme

N,N'-dihydroxy-2,3-dimethylbutane-2,3-diamine (14384-45-3) + 2,2′-bipyridine-5,5′-dicarbaldehyde (135822-72-9) → 5,5'-bis(1,3-dihydroxy-4,4,5,5-tetramethylimidazolin-2-yl)-2,2'-bipyridine

Conditions	Yield
In toluene Inert atmosphere; Reflux;	88%
In methanol at 20℃; for 72h; Condensation;	85%

2,2′-bipyridine-5,5′-dicarbaldehyde (135822-72-9) + (1S,2S)-cyclohexane-1,2-diammonium 2,3-dihydroxysuccinate → C54H54N12

Conditions	Yield
With triethylamine In methanol; chloroform at 20℃; for 24h;	84%

2,2′-bipyridine-5,5′-dicarbaldehyde (135822-72-9) + (1R,2R)-1,2-diaminocyclohexane tartrate → C54H54N12

Conditions	Yield
With triethylamine In methanol; chloroform at 20℃; for 24h;	82%

2,2',2''-triaminotriethylamine (4097-89-6) + 2,2′-bipyridine-5,5′-dicarbaldehyde (135822-72-9) → N2((CH2)2NCH(C5NH3)2CHN(CH2)2)3 (135852-89-0)

Conditions	Yield
In acetonitrile Ambient temperature;	78%

4,4’,4’’,4’’’-(pyrene-1,3,6,8-tetrayl) tetra aniline (1610471-69-6) + 2,2′-bipyridine-5,5′-dicarbaldehyde (135822-72-9) → C208H136N24

Conditions	Yield
With acetic acid In 1,3-dioxane; water; 1,3,5-trimethyl-benzene at 120℃; for 168h;	76.8%

2,2′-bipyridine-5,5′-dicarbaldehyde (135822-72-9) + 1,2-diamino-benzene (95-54-5) → 5,5′-bis(1H-benzo[d]imidazol-2-yl)-2,2′-bipyridine

Conditions	Yield
In dimethyl sulfoxide at 120℃; for 6h;	75%

n-Dodecylamine (124-22-1) + 2,2′-bipyridine-5,5′-dicarbaldehyde (135822-72-9) → 4,4'-didodecyldiimino-2,2'-bipyridine

Conditions	Yield
In ethanol for 7h; Heating;	72%

2,2′-bipyridine-5,5′-dicarbaldehyde (135822-72-9) + 2-amino-phenol (95-55-6) → C24H18N4O2

Conditions	Yield
In ethanol at 70℃; for 3h;	70%

diisopropyl zinc (625-81-0) + 2,2′-bipyridine-5,5′-dicarbaldehyde (135822-72-9) → 2-isopropyl-1,2-dihydro-[2,2']bipyridinyl-5,5'-dicarbaldehyde

Conditions	Yield
In toluene at 0℃; for 1h;	69%

3,5-dimethyl-4H-1,2,4-triazol-4-amine (3530-15-2) + 2,2′-bipyridine-5,5′-dicarbaldehyde (135822-72-9) → C20H20N10

Conditions	Yield
In ethanol Solvent; Concentration; Reflux;	69%

1,3,5,7-tetrakis-(4-aminophenyl)adamantane + 2,2′-bipyridine-5,5′-dicarbaldehyde (135822-72-9) → C82H60N12O4

Conditions	Yield
With acetic acid In 1,4-dioxane; water at 140℃; for 120h; Temperature; Sonication; Sealed tube;	68%

N,N'-dihydroxy-2,3-dimethylbutane-2,3-diamine (14384-45-3) + 2,2′-bipyridine-5,5′-dicarbaldehyde (135822-72-9) → 5,5'-bis(3''-oxide-1''-oxyl-4'',4'', 5'',5''-tetramethylimidazolin-2''-yl)-2,2'-bipyridine (156137-23-4)

Conditions	Yield
With sodium periodate In dichloromethane; water at 0℃;	52%

2,2′-bipyridine-5,5′-dicarbaldehyde (135822-72-9) + 5,5'-Bis(carboxyethyl)-2,2'-bipyridine (153305-75-0) → Poly(5,5'-vinylene-2,2'-bipyridine)

Conditions	Yield
With sodium ethanolate In ethanol; dichloromethane at 20℃;	50%

isopropylmagnesium bromide (920-39-8) + 2,2′-bipyridine-5,5′-dicarbaldehyde (135822-72-9) → 5'-(1-hydroxy-2-methyl-propyl)-[2,2']bipyridinyl-5-carbaldehyde + 1-[5'-(1-hydroxy-2-methyl-propyl)-[2,2']bipyridinyl-5-yl]-2-methyl-propan-1-ol

Conditions	Yield
In tetrahydrofuran; diethyl ether at 0℃;	A 17% B 35%

2,2′-bipyridine-5,5′-dicarbaldehyde (135822-72-9) + ethylene glycol (107-21-1) → 5,5'-di(1,3-dioxolan-2-yl)-2,2'-bipyridine (1429408-43-4)

Conditions	Yield
With toluene-4-sulfonic acid at 110℃; Inert atmosphere;	35%

3,5-dimethyl-4H-1,2,4-triazol-4-amine (3530-15-2) + 2,2′-bipyridine-5,5′-dicarbaldehyde (135822-72-9) → C20H24N10O2

Conditions	Yield
In acetonitrile Reflux;	31%

di-n-butylzinc (1119-90-0) + 2,2′-bipyridine-5,5′-dicarbaldehyde (135822-72-9) → 2-butyl-1,2-dihydro-[2,2']bipyridinyl-5,5'-dicarbaldehyde + 5'-(1-hydroxy-pentyl)-[2,2']bipyridinyl-5-carbaldehyde + 1-[5'-(1-hydroxy-pentyl)-[2,2']bipyridinyl-5-yl]-pentan-1-ol

Conditions	Yield
In toluene at 0℃;	A 17% B 26% C 15%

diethylzinc (557-20-0) + 2,2′-bipyridine-5,5′-dicarbaldehyde (135822-72-9) → 2-ethyl-1,2-dihydro-[2,2']bipyridinyl-5,5'-dicarbaldehyde + 5'-(1-hydroxy-propyl)-[2,2']bipyridinyl-5-carbaldehyde + 1-[5'-(1-hydroxy-propyl)-[2,2']bipyridinyl-5-yl]-propan-1-ol

Conditions	Yield
In toluene at 0℃;	A 19% B 18% C 24%

isopropyllithium (1888-75-1) + 2,2′-bipyridine-5,5′-dicarbaldehyde (135822-72-9) → 5'-(1-hydroxy-2-methyl-propyl)-[2,2']bipyridinyl-5-carbaldehyde + 1-[5'-(1-hydroxy-2-methyl-propyl)-[2,2']bipyridinyl-5-yl]-2-methyl-propan-1-ol

Conditions	Yield
In toluene; pentane at 0℃;	A 3% B 9%

N,N'-dihydroxy-2,3-dimethylbutane-2,3-diamine (14384-45-3) + 2,2′-bipyridine-5,5′-dicarbaldehyde (135822-72-9) → C24H32N6O2

Conditions	Yield
With selenium(IV) oxide In methanol Ambient temperature;

tetrakis-5,10,15,20-(o-aminophenyl)porphyrin (52199-35-6) + 2,2′-bipyridine-5,5′-dicarbaldehyde (135822-72-9) → C136H84N24

Conditions	Yield
With trifluoroacetic acid In N,N-dimethyl acetamide; acetonitrile for 12h; Ambient temperature;

2,2′-bipyridine-5,5′-dicarbaldehyde (135822-72-9) → 5,5'-bis(3''-oxide-1''-oxyl-4'',4'', 5'',5''-tetramethylimidazolin-2''-yl)-2,2'-bipyridine (156137-23-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: 85 percent / methanol / 72 h / 20 °C 2: 52 percent / aq. sodium periodate / CH2Cl2 / 1 h View Scheme

2,2′-bipyridine-5,5′-dicarbaldehyde (135822-72-9) → 2,2'-(bipyridine-1,1'-diyl)bis(4,4,5,5-tetramethylimidazolidine-1-oxyl)

Conditions	Yield
Multi-step reaction with 2 steps 1: SeO2 / methanol / Ambient temperature 2: 65 percent / NaIO4 View Scheme
Multi-step reaction with 2 steps 1: toluene / Inert atmosphere; Reflux 2: manganese(IV) oxide / nitromethane / 0.58 h / 20 °C View Scheme

Upstream product

• 63361-65-9 5,5’-bis(hydroxymethyl)-2,2’-bipyridine 
• 153305-75-0 5,5'-Bis(carboxyethyl)-2,2'-bipyridine 
• 1802-30-8 2,2'-bipyridine-5,5'-dicarboxylic acid 
• 1762-46-5 [2,2']bipyridinyl-5,5'-dicarboxylic acid diethyl ester 
• 92642-09-6 5,5'-bis(bromomethyl)-2,2'-bipyridine 
• 1762-34-1 5,5'-dimethyl-2,2'-bipyridine 

Relevant articles and documents

Colorimetric detection of in situ metal acetates and fluorides by a bipyridyl-linked Schiff base

A new bipyridyl moiety linked Schiff base (bipy-1) was developed and showed selective recognition of dimethyl sulphoxide solution of tetrabutyl ammonium salt of F- ion with absorbance at 529 nm and interesting binding of aqueous Co, Ni, and Cu acetates/fluorides, as confirmed by distinct color changes from fluorescent green to pink or orange with absorbance at 480-510 nm. However, in situ formation of Co, Ni, and Cu acetates/fluorides also was found to be able to respond to similar color and absorption changes.

Unusual chemoselective addition of diisopropylzinc to 2,2′-bipyridine-5,5′-dicarbonyl compounds in the 2-position and autoxidative reconversion with carbon-carbon bond cleavage

The chemoselective addition of diisopropylzinc to 2,2′-bipyridine-5,5′-dicarbonyl compounds in the 2-position and autoxidative reconversion with carbon-carbon bond cleavage was presented. It was shown that i-Pr2Zn do not add to the aldehyde moiety but to the 2-position of the bipyridine to afford possessing a quaternary carbon atom in a yield of 69%. It was found that the i-Pr2Zn does not add to the aldehyde but to the 2-position of the bipyridine ring by destroying the aromaticity of the pyridine ring.

Photocurrent response of bipyridine containing poly(p-phenylene-vinylene) derivatives

The photoinduced charge separation and subsequent transport under an external electric field is studied in the family of poly[bipyridine/(p-phenylene-vinylene)n] derivatives having n = 0, 1, and 3, respectively, p-phenylene-vinylene subunits separating the bipyridylene vinylene skeleton. Steady-state photocurrent of the polymers is studied in sandwich and surface configurations and correlated with transient photocurrent measurements. The results reveal the facile electric-field-induced separation of the electron-hole pair for n = 1 samples relative to n = 3 samples. We also estimate the energy barriers involved in the process of carrier generation and transport in these systems.

Designed synthesis of porphyrin-based two-dimensional covalent organic frameworks with highly ordered structures

Porphyrins are representative functional π-systems; synthesizing their highly ordered structures is an established goal in chemistry. Here, we report the designed synthesis of a series of porphyrin-based covalent organic frameworks with highly ordered structures through polycondensation. The porphyrinbased frameworks exhibited high crystallinity, high porosity, and extended π-conjugation over the polyporphyrin sheets.

Phosphonate-Mediated Immobilization of Rhodium/Bipyridine Hydrogenation Catalysts

RhL2 complexes of phosphonate-derivatized 2,2′-bipyridine (bpy) ligands L were immobilized on titanium oxide particles generated in situ. Depending on the structure of the bipy ligand—number of tethers (1 or 2) to which the phosphonate end groups are attached and their location on the 2,2′-bipyridine backbone (4,4′-, 5,5′-, or 6,6′-positions)—the resulting supported catalysts showed comparable chemoselectivity but different kinetics for the hydrogenation of 6-methyl-5-hepten-2-one under hydrogen pressure. Characterization of the six supported catalysts suggested that the intrinsic geometry of each of the phosphonate-derivatized 2,2′-bipyridines leads to supported catalysts with different microstructures and different arrangements of the RhL2 species at the surface of the solid, which thereby affect their reactivity.