2,2'-Bipyridine

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

Product Name: 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
Formula Weight: 156.18
MOL File: 366-18-7.mol

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2,2'-Bipyridine Property

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
pka: pK1:-0.52(+2);pK2:4.352(+1) (20°C)
form: Crystalline Powder
color: White to almost white
PH: 7.5 (5g/l, H2O, 25℃)
Odor: Characteristic odour
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)
NIST Chemistry Reference: 2,2'-Bipyridine(366-18-7)
EPA Substance Registry System: 2,2'-Bipyridine (366-18-7)

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Safety

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
F: 8
Hazard Note: Irritant
TSCA: Yes
HazardClass: 6.1
PackingGroup: III
HS Code: 29333999
Hazardous Substances Data: 366-18-7(Hazardous Substances Data)
Toxicity: LD50 i.p. in mice: 200 mg/kg (Grady)

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P310IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: 798533
Product name: 2,2′-Bipyridyl
Purity: anhydrous, free-flowing, Redi-Dri , ReagentPlus , 99%
Packaging: 50g
Price: $142
Updated: 2024/03/01

Sigma-Aldrich

Product number: 798533
Product name: 2,2′-Bipyridyl
Purity: anhydrous, free-flowing, Redi-Dri , ReagentPlus , 99%
Packaging: 100g
Price: $158
Updated: 2024/03/01

Sigma-Aldrich

Product number: 1.03098
Product name: 2,2′-Bipyridine
Purity: GR for analysis (reagent for iron(II) and molybdenum) ACS
Packaging: 25g
Price: $216
Updated: 2024/03/01

Sigma-Aldrich

Product number: 1.03098
Product name: 2,2′-Bipyridine
Purity: GR for analysis (reagent for iron(II) and molybdenum) ACS
Packaging: 5G
Price: $55.1
Updated: 2022/05/15

TCI Chemical

Product number: B0468
Product name: 2,2'-Bipyridyl
Purity: >99.0%(T)
Packaging: 25g
Price: $49
Updated: 2024/03/01

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2,2'-Bipyridine Chemical Properties,Usage,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.

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.

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.

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.]

2,2'-Bipyridine Preparation Products And Raw materials

Raw materials

2-Picoline Ferric chloride Anhydrous pyridine

Preparation Products

1,1'-Bis (di-t-butylphosphino)ferrocene palladium dichloride, 1,1'-Bis(di-tert-butylphosphino)ferrocene Tetrahydro-4H-pyran-4-one TRIS(2,2'-BIPYRIDYL)RUTHENIUM(II) CHLORIDE HEXAHYDRATE 3-(DIMETHYLCARBAMOYL)PHENYLBORONIC ACID 4-(Dimethylamino)phenylboronic acid

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View Lastest Price from 2,2'-Bipyridine manufacturers

Speranza Chemical Co., Ltd.

Product: 2,2' Dipyridyl 366-18-7
Price: US $20.00/KG
Min. Order: 1KG
Purity: 99%
Supply Ability: 200 tons/ year
Release date: 2020-03-11

Hebei Kangcang new material Technology Co., LTD

Product: 2,2'-Bipyridine 366-18-7
Price: US $9.00-70.00/g
Min. Order: 10g
Purity: 99%
Supply Ability: 10 tons
Release date: 2024-03-27

Henan Fengda Chemical Co., Ltd

Product: 2,2'-Bipyridine 366-18-7
Price: US $2.00-0.50/KG
Min. Order: 1KG
Purity: 99%
Supply Ability: g-kg-tons, free sample is available
Release date: 2024-04-15

366-18-7, 2,2'-BipyridineRelated Search:

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bpy

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α,α'-Dipyridyl, 2,2'-Dipyridyl

2,2'-BIPYRIDINE GR FOR ANALYSIS (REAGENT

2,2'-Bipyridine, ACS, 98%

AA-DP

alpha,alpha’-dipyridine

alpha,alpha’-dwupirydylu

alpha,alpha'-Dipyridine

Bipyridine

2,2-Bipyridine, Reagent

2,2’-dipyridine

BIPY

BIPYRIDINE(2,2'-)

2,2'-Bipyridin

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2,2'-Bipyridine, ACS, 98.0% min.

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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-Pyridyl)pyridine

2,2’-bipyridin

CI-588

'LGC' (1607)

2,2'-DIPYRIDYL

2,2'-BIPYRIDYL

2,2-BIPYRIDYL

2,2'-BIPYRIDINE

2,2-BIPYRIDINE

2-PYRIDIN-2-YLPYRIDINE

A,A'-DIPYRIDYL

ALPHA, ALPHA'-BIPYRIDINE

ALPHA, ALPHA'-BIPYRIDYL

ALPHA,ALPHA'-DIPYRIDYL

α,α’-Bipyridyl

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)