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2,2'-Dipyridyl
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Name

2,2'-Dipyridyl

 EINECS 206-674-4
CAS No. 366-18-7 Density 1.106 g/cm3
PSA 25.78000 LogP 2.14360
Solubility 5.5 g/L 22 ºC Melting Point 70-73 °C(lit.)
Formula C10H8N2 Boiling Point 272.499 °C at 760 mmHg
Molecular Weight 157.195 Flash Point 107.243 °C
Transport Information UN 2811 6.1/PG 3 Appearance White crystalline powder
Safety 36/37-45-36/37/39-26 Risk Codes 25-36/37/38-20/21-23/24/25
Molecular Structure Molecular Structure of 366-18-7 (2,2'-Bipyridine) Hazard Symbols ToxicT, IrritantXi
Synonyms

2,2'-Bipyridine;alpha,alpha'-Dipyridyl;2-(2-Pyridyl)pyridine;

Article Data 335

2,2'-Dipyridyl Synthetic route

109-04-6

2-bromo-pyridine

366-18-7

[2,2]bipyridinyl

Conditions
ConditionsYield
With palladium diacetate; potassium carbonate In water; N,N-dimethyl-formamide at 210℃; for 24h; Catalytic behavior; Solvent; Reagent/catalyst;100%
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; cesium fluoride In dimethyl sulfoxide at 120℃; for 8h;96%
With bis(triphenylphosphine)nickel(II) chloride; sodium hydride; triphenylphosphine; zinc In toluene at 70 - 90℃; Ullmann-type coupling;93%
115981-39-0

ethyl(1,1,1,3,3,3-hexafluoro-2-propoxo)(2,2'-bipyridine)nickel

A

366-18-7

[2,2]bipyridinyl

B

24499-62-5

1,1,1,3,3,3-hexafluoropropan-2-yl propionate

Conditions
ConditionsYield
With carbon monoxide In tetrahydrofuran Addn. of CO (ambient pressure) to metal complex (THF, room temp.), stirring (2.5 h).; Trap-to-trap distn., GLC anal.;A 100%
B 97%
115981-38-9

methyl(1,1,1,3,3,3-hexafluoro-2-propoxo)(2,2'-bipyridine)nickel

A

366-18-7

[2,2]bipyridinyl

B

6919-79-5

1,1,1,3,3,3-hexafluoropropan-2-yl acetate

Conditions
ConditionsYield
With carbon monoxide In tetrahydrofuran Addn. of CO (ambient pressure) to metal complex (THF, room temp.), stirring (2.5 h).; Trap-to-trap distn., GLC anal.;A 100%
B 98%
5029-67-4

2-iodopyridine

366-18-7

[2,2]bipyridinyl

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine; johnphos; bis(dibenzylideneacetone)-palladium(0) In 1-methyl-pyrrolidin-2-one at 20℃; for 12h;99%
With sodium hydroxide; triethylammonium formate; zinc In methanol for 2.5h; Heating;92%
With sodium hydroxide; ammonium formate; zinc In methanol for 2.5h; Heating;90%
109-09-1

2-chloropyridine

C10H13BNO3(1-)*C16H36N(1+)

366-18-7

[2,2]bipyridinyl

Conditions
ConditionsYield
With (2-hydroxyethyl)(methyl)amine; copper(l) iodide; dichloro(1,3-bis(dicyclohexylphosphino)propane)palladium In N,N-dimethyl-formamide at 100℃; for 16h; Suzuki-Miyaura Coupling; Inert atmosphere;99%
33421-43-1

2,2'-bipyridyl N-oxide

366-18-7

[2,2]bipyridinyl

Conditions
ConditionsYield
With (4,4′-di-tert-butyl-2,2′-bipyridine)bis[(2-pyridinyl)phenyl]iridium(III) hexafluorophosphate; di-tert-butyl 1,4-dihydro-2,6-dimethyl-3,5-pyridine-dicarboxylate In 2,2,2-trifluoroethanol; acetonitrile at 20℃; for 3h; Inert atmosphere; Irradiation; chemoselective reaction;98%
With (4,4'-di-tert-butyl-2,2'-dipyridyl)-bis-(2-phenylpyridine(-1H))-iridium(III) hexafluorophosphate; hydrazine hydrate In dimethyl sulfoxide at 20℃; for 27h; Inert atmosphere; Irradiation; chemoselective reaction;96%
With N-Bromosuccinimide In chlorobenzene at 150℃; for 17h;20 %Spectr.
100-70-9

2-Cyanopyridine

74-86-2

acetylene

366-18-7

[2,2]bipyridinyl

Conditions
ConditionsYield
In 5,5-dimethyl-1,3-cyclohexadiene at 170℃; for 16h;97.4%
With cyclooctadienyl cobalt at 140 - 190℃; for 2h; Temperature; Autoclave;250 g
29745-44-6

pyridine-2-carbonyl chloride

109-73-9

N-butylamine

366-18-7

[2,2]bipyridinyl

Conditions
ConditionsYield
With dmap; copper(II) ethylacetoacetate; C26H36NP; silver(I) acetate In 1,2-dichloro-ethane at 90℃; for 8h; Reagent/catalyst;96.7%
109-09-1

2-chloropyridine

366-18-7

[2,2]bipyridinyl

Conditions
ConditionsYield
With potassium hydroxide In water; N,N-dimethyl-formamide at 35℃; for 12h; Reagent/catalyst; Ullmann Condensation; Inert atmosphere;96%
With aluminum oxide; nickel(II) chloride hexahydrate; sodium hydroxide; zinc In methanol; water at 50℃; for 3h; Reagent/catalyst; Temperature;95%
With manganese; nickel(II) bromide trihydrate In N,N-dimethyl-formamide at 20 - 60℃; for 20h; Inert atmosphere;86%
7275-43-6

[2,2']bipyridinyl 1,1'-dioxide

366-18-7

[2,2]bipyridinyl

Conditions
ConditionsYield
With titanium tetrachloride; tin(ll) chloride In benzene for 0.5h; Ambient temperature;95%
With titanium In tetrahydrofuran for 0.25h; Ambient temperature;90%
With sodium hypophosphite; palladium on activated charcoal In acetic acid at 60℃; for 1h;90%

2,2'-Dipyridyl Specification

The 2,2'-Bipyridine, with the CAS registry number 366-18-7 and EINECS registry number 206-674-4, is also called 2-(2-pyridyl)pyridine. And the molecular formula of this chemical is C10H8N2. It is a kind of colorless solid, commonly abbreviated bipy or bpy, and is an important isomer of the bipyridine family. It is a bidentate chelating ligand, forming complexes with many transition metals. Ruthenium complex and platinum complexes of bipy exhibit intense luminescence, which may have practical applications.

The physical properties of 2,2'-Bipyridine are as following: (1)ACD/LogP: 1.69; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.661; (4)ACD/LogD (pH 7.4): 1.694; (5)ACD/BCF (pH 5.5): 10.576; (6)ACD/BCF (pH 7.4): 11.404; (7)ACD/KOC (pH 5.5): 184.252; (8)ACD/KOC (pH 7.4): 198.676; (9)#H bond acceptors: 2; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 1; (12)Polar Surface Area: 25.78 Å2; (13)Index of Refraction: 1.581; (14)Molar Refractivity: 47.027 cm3; (15)Molar Volume: 141.166 cm3; (16)Polarizability: 18.643×10-24cm3; (17)Surface Tension: 46.65 dyne/cm; (18)Density: 1.106 g/cm3; (19)Flash Point: 107.243 °C; (20)Enthalpy of Vaporization: 49.023 kJ/mol; (21)Boiling Point: 272.499 °C at 760 mmHg; (22)Vapour Pressure: 0.01 mmHg at 25°C.

Uses and preparation of 2,2'-Bipyridine: It is used as analytical reagent for the determination of iron, silver, cadmium, molybdenum. It is also used as redox indicator. What's more, it can be prepared by the dehydrogenation of pyridine using Raney nickel:

2,2'-Bipyridine can be prepared by the dehydrogenation of pyridine using Raney nickel

You should be cautious while dealing with this chemical. It is toxic if swallowed. Therefore, you had better take the following instructions: Wear suitable protective clothing and gloves, and in case of accident or if you feel unwell, seek medical advice immediately (show label where possible).

You can still convert the following datas into molecular structure:
(1)SMILES: c1ccnc(c1)c2ccccn2
(2)InChI: InChI=1/C10H8N2/c1-3-7-11-9(5-1)10-6-2-4-8-12-10/h1-8H
(3)InChIKey: ROFVEXUMMXZLPA-UHFFFAOYAP

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 200mg/kg (200mg/kg) KIDNEY, URETER, AND BLADDER: OTHER CHANGES IN URINE COMPOSITION

KIDNEY, URETER, AND BLADDER: OTHER CHANGES		 Journal of Pharmacology and Experimental Therapeutics. Vol. 196, Pg. 478, 1976.
mouse LD50 oral 330mg/kg (330mg/kg)   United States Patent Document. Vol. #3875163,
rat LD50 intraperitoneal 150mg/kg (150mg/kg)   Polish Journal of Pharmacology and Pharmacy. Vol. 27, Pg. 619, 1975.
rat LD50 oral 100mg/kg (100mg/kg) BEHAVIORAL: MUSCLE WEAKNESS

KIDNEY, URETER, AND BLADDER: OTHER CHANGES IN URINE COMPOSITION

BLOOD: HEMORRHAGE		 Journal of Toxicology and Environmental Health. Vol. 10, Pg. 363, 1982.
rat LD50 subcutaneous 131mg/kg (131mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 135, Pg. 317, 1962.

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