ChemicalBook >> CAS DataBase List >>2,2'-Bipyridine

2,2'-Bipyridine

CAS No.
366-18-7
Chemical Name:
2,2'-Bipyridine
Synonyms
bpy;BIPY;Bipyridine;2,2-BIPYRIDINE;2,2-BIPYRIDYL;2,2-Bispyridine;2-(2-Pyridyl)pyridine;2,2'-BIPYRIDYL;2,2’-dipyridine;2-PYRIDIN-2-YLPYRIDINE
CBNumber:
CB5195697
Molecular Formula:
C10H8N2
Molecular Weight:
156.18
MDL Number:
MFCD00006212
MOL File:
366-18-7.mol
MSDS File:
SDS
Last updated:2024-04-15 21:43:12

2,2'-Bipyridine Properties

Melting point 70-73 °C(lit.)
Boiling point 273 °C(lit.)
Density 1.1668 (rough estimate)
vapor pressure 0.584Pa at 25℃
refractive index 1.4820 (estimate)
Flash point 121 °C
storage temp. room temp
solubility 5.5g/l
form Crystalline Powder
pka pK1:-0.52(+2);pK2:4.352(+1) (20°C)
color White to almost white
Odor Characteristic odour
PH 7.5 (5g/l, H2O, 25℃)
Water Solubility 5.5 g/L 22 ºC
Merck 14,3347
BRN 113089
Stability Stable. Incompatible with strong oxidizing agents, most common metals. May be light sensitive.
InChIKey ROFVEXUMMXZLPA-UHFFFAOYSA-N
CAS DataBase Reference 366-18-7(CAS DataBase Reference)
EWG's Food Scores 1
FDA UNII 551W113ZEP
NIST Chemistry Reference 2,2'-Bipyridine(366-18-7)
EPA Substance Registry System 2,2'-Bipyridine (366-18-7)

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
GHS06
Signal word  Danger
Hazard statements  H301+H311
Precautionary statements  P264-P270-P280-P301+P310-P302+P352+P312-P361+P364
Hazard Codes  T,Xi
Risk Statements  25-36/37/38-20/21-23/24/25-21
Safety Statements  36/37-45-36/37/39-26
RIDADR  UN 2811 6.1/PG 3
WGK Germany  3
RTECS  DW1750000
8
Hazard Note  Irritant
TSCA  Yes
HazardClass  6.1
PackingGroup  III
HS Code  29333999
Toxicity LD50 i.p. in mice: 200 mg/kg (Grady)
NFPA 704
1
3 0

2,2'-Bipyridine price More Price(64)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich 798533 2,2′-Bipyridyl anhydrous, free-flowing, Redi-Dri , ReagentPlus , 99% 366-18-7 50g $142 2024-03-01 Buy
Sigma-Aldrich 798533 2,2′-Bipyridyl anhydrous, free-flowing, Redi-Dri , ReagentPlus , 99% 366-18-7 100g $158 2024-03-01 Buy
Sigma-Aldrich 1.03098 2,2′-Bipyridine GR for analysis (reagent for iron(II) and molybdenum) ACS 366-18-7 25g $216 2024-03-01 Buy
Sigma-Aldrich 1.03098 2,2′-Bipyridine GR for analysis (reagent for iron(II) and molybdenum) ACS 366-18-7 5G $55.1 2022-05-15 Buy
TCI Chemical B0468 2,2'-Bipyridyl >99.0%(T) 366-18-7 25g $49 2024-03-01 Buy
Product number Packaging Price Buy
798533 50g $142 Buy
798533 100g $158 Buy
1.03098 25g $216 Buy
1.03098 5G $55.1 Buy
B0468 25g $49 Buy

2,2'-Bipyridine Chemical Properties,Uses,Production

Chemical Properties

White to light red crystalline powder. Soluble in ethanol, ether, benzene, chloroform and petroleum ether, 1 part of this product is about 200 parts of water.

Uses

A high-affinity chelator of iron. A reagent used for the determination of iron.

Uses

2,2'-bipyridine acts as a bidentate chelating ligand which form complexes with transition metal ions and shows antifungal, antibacterial and antiviral activity. It is used for the colorimetric determination of iron as well as oxidation reduction indicators to confirm the presence of ferrous ion in soils. It forms complexes with ruthenium and platinum, exhibit intense luminescence, which may have practical applications. Copper(I) bipyridine complexes involved in the oxidation of alcohols under aerobic conditions.

Preparation

2,2'-bipyridine is synthesized by the reaction of pyridine with ferric chloride. Take 70g of anhydrous pyridine and mix with 13g of anhydrous ferric chloride, heat and react at 300℃ in a sealed tube for about 35h. After cooling, the reactant solidified into red-black crystals, the sealing tube was opened, and the red-black solution of the solid was washed out with a small amount of hot water. The oily impurities were removed by extraction with ether. After neutralization with sodium bicarbonate, excess pyridine was removed by heating with steam. The mixture was then made strongly basic, and the 2,2'-bipyridine was distilled off with steam.

Definition

ChEBI: 2,2'-bipyridine is a bipyridine in which the two pyridine moieties are linked by a bond between positions C-2 and C-2'. It has a role as a ferroptosis inhibitor and a chelator.

Reactions

A large number of complexes of 2,2'-bipyridine have been described.It binds metals as a chelating ligand, forming a 5-membered chelate ring.

Synthesis Reference(s)

Journal of the American Chemical Society, 100, p. 5567, 1978 DOI: 10.1021/ja00485a053
Synthesis, p. 564, 1986 DOI: 10.1055/s-1986-31705

General Description

2,2′-Bipyridyl, is a symmetrical bipyridine commonly used as a neutral ligand for complexation with metal ions. The molecule is planar with trans-conformation and crystallizes in the monoclinic crystal system.

Biochem/physiol Actions

Metalloprotease inhibitor, high-affinity chelator of iron; may inhibit Fe2+ containing enzymes at 10?8?M.

Safety Profile

Poison by ingestion,subcutaneous, and intraperitoneal routes. Experimentalteratogenic data. Questionable carcinogen withexperimental tumorigenic data. Mutation data reported.When heated to decomposition it emits toxic fumes ofNOx.

Source

2,2'-Bipyridine is a natural product found in Dichilus strictus, Dichilus gracilis, and other organisms with data available.

Purification Methods

2,2'-Bipyridyl crystallises from hexane, or EtOH, or (after charcoal treatment of a CHCl3 solution) from pet ether. Also, it precipitates from a concentrated solution in EtOH by addition of H2O. Dry it in a vacuum over P2O5. It can be further purified by chromatography on Al2O3 or by sublimation. UV (EtOH): at 280nm (log 4.13). max [Airoldi et al. J Chem Soc, Dalton Trans 1913 1986, Beilstein 23 H 199, 23/8 V 16.]

29745-44-6
109-73-9
366-18-7
Synthesis of 2,2'-Bipyridine from 2-PYRIDINECARBOXYLICACID CHLORIDE and Butylamine
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View Lastest Price from 2,2'-Bipyridine manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
2,2' Dipyridyl pictures 2024-05-24 2,2' Dipyridyl
366-18-7
US $20.00 / KG 1KG 99% 200 tons/ year Speranza Chemical Co., Ltd.
2,2'-Bipyridine pictures 2024-05-11 2,2'-Bipyridine
366-18-7
US $9.00-70.00 / g 10g 99% 10 tons Hebei Kangcang new material Technology Co., LTD
2,2'-Bipyridine pictures 2024-04-15 2,2'-Bipyridine
366-18-7
US $2.00-0.50 / KG 1KG 99% g-kg-tons, free sample is available Henan Fengda Chemical Co., Ltd
  • 2,2'-Bipyridine pictures
  • 2,2'-Bipyridine
    366-18-7
  • US $9.00-70.00 / g
  • 99%
  • Hebei Kangcang new material Technology Co., LTD
  • 2,2'-Bipyridine pictures
  • 2,2'-Bipyridine
    366-18-7
  • US $2.00-0.50 / KG
  • 99%
  • Henan Fengda Chemical Co., Ltd
2,2'-Bipyridine, ACS, 98.0% min. 2,2-Bipyridyl (2,2-Bipyridine) 2,2'-Bipyridyl ReagentPlus(R), >=99% 2,2'-Bipyridyl Vetec(TM) reagent grade, 98% 2,2'-Bipyridine GR for analysis (reagent for iron(II) and molybdenum) ACS 2,2'-Dipyridyl≥ 99.5% (GC) ,’-Dipyridyl 2,2’-bipyridin CI-588 'LGC' (1607) 2,2'-DIPYRIDYL 2,2'-BIPYRIDINE A,A'-DIPYRIDYL ALPHA, ALPHA'-BIPYRIDINE ALPHA, ALPHA'-BIPYRIDYL ALPHA,ALPHA'-DIPYRIDYL 2,2-Dipyridyl (2,2-bipyridine) 2,2-Dipyridyl 99.5+ % for analysis BipyridineBIPYwhiteoffwhitextl 2,2'Bipyridinyl 2,2'-BIPYRIDYL, REDOX INDICATOR 2,2'-DIPYRIDYL, REAGENTPLUS, >=99% 2,2'-BIPYRIDINE PESTANAL 2,2,-Dipyridyl99+% 2, 2- DIPYRIDYL GR 2-2-BIPYRIDYL GR (2,2-Dipyridyl) 2,2'-Bipyridyl,99% 2,2'-BIPYRIDINE, REAG. 2,2'-BIPYRIDINE REAGENT (ACS) 2,2bipyridine, Bipyridine, Alpha, alphabipyridine, Alpha, alphabipyridyl, 2,2bipyridyl, CI-588, Alpha, alphadipyridyl, 2,2dipyridyl 2,2'-Bipyridine,99+%BIPY 2,2''-BIPYRIDINE BIPY 2,2''-DIPYRIDINE / 2,2''-DIPYRIDYL 2.2-BIPHENYL 99% 2,2''-BIPYRIDYL, GR 99+% 2,2'-Bipyridine, 99+% 2,2'-BIPYRIDINE (2,2'-Bipyridyl) 2'-Bipyridine 2,2-Dipyridyl 99+%, White Crystalline Powder, Reagent Grade α,α'-Dipyridyl, 2,2'-Dipyridyl 2,2'-BIPYRIDINE GR FOR ANALYSIS (REAGENT 2,2'-Bipyridine, ACS, 98% AA-DP alpha,alpha’-dwupirydylu alpha,alpha'-Dipyridine 2,2-Bipyridine, Reagent BIPYRIDINE(2,2'-) 2,2'-Bipyridin 2,2'-Dipyridine 2, 2 - al pyridine 2,2′-Bipyridyl,anhydrous, free-flowing 2,6'-Bipyridine 2,2'-Dipyridyl p.a. -Hydroxyphenyl)-2-butanone-d5 Oxime -Bipyridyl, 2,3&rsquo Isonicoteine (2,3&rsquo Anabaseine (3,4,5,6-Tetrahydro-2,3&rsquo B**2 2'-BIPYRIDYL