CAS No.366-18-7,2,2'-Bipyridine Suppliers,MSDS download

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Basic Information

Molecular Structure:
CAS No.:	366-18-7
Name:	2,2'-Bipyridine
Article Data:	335

Formula:	C₁₀H₈N₂
Molecular Weight:	157.195
Synonyms:	2,2'-Bipyridine;alpha,alpha'-Dipyridyl;2-(2-Pyridyl)pyridine;
EINECS:	206-674-4
Density:	1.106 g/cm³
Melting Point:	70-73 °C(lit.)
Boiling Point:	272.499 °C at 760 mmHg
Flash Point:	107.243 °C
Solubility:	5.5 g/L 22 ºC
Appearance:	White crystalline powder
Hazard Symbols:	T, Xi
Risk Codes:	25-36/37/38-20/21-23/24/25
Safety:	36/37-45-36/37/39-26
Transport Information:	UN 2811 6.1/PG 3
PSA:	25.78000
LogP:	2.14360

Synthetic route

: 109-04-6
2-bromo-pyridine

: 366-18-7
[2,2]bipyridinyl

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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%

Raw Materials

768-94-5

109-09-1

874-72-6

Downstream Products

531-67-9

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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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