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

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’-dipyridine;2-PYRIDIN-2-YLPYRIDINE;alpha,alpha’-dipyridine
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)
bulk density
500kg/m3
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
biological source
synthetic (organic)
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.]

Toxics Screening Level

The initial threshold screening level (ITSL) for 2,2'-bipyridyl is 0.8 μg/m3 based on an annual averaging time.

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 Zhuanglai Chemical Trading Co Ltd
Product
2,2'-Bipyridine 366-18-7
Price
US $10.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
20 ton
Release date
2024-11-29
Shanghai UCHEM Inc.
Product
2,2’-Bipyridine 366-18-7
Price
US $65.00-495.00/g
Min. Order
1g
Purity
0.98
Supply Ability
25kg
Release date
2023-10-19

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

2-Chloro-3-cyanopyridine Sulfasalazine Chromium picolinate DIPIPERIDINOMETHANE Pyridine 2,6-Lutidine 4,4'-DIMETHYL-2,2'-DIPYRIDYL,4,4'-Dimethyl-2,2'-dipyridyl ,98%,4,4'-DIMETHYL-2,2'-DIPYRIDYL, SUBLIMED & 2,2'-DIPYRIDYL-4,4'-DICARBOXYLIC ACID 4,4'-DIPHENYL-2,2'-DIPYRIDYL,4,4'-DIPHENYL-2,2'-DIPYRIDYL, TECH. Bicinchoninic Acid Disodium Salt 2,2'-BIQUINOLINE-4,4'-DICARBOXYLIC ACID DIPOTASSIUM SALT TRIHYDRATE 2,2':6',2''-TERPYRIDINE 4,5-DIAZAFLUOREN-9-ONE 1 10-PHENANTHROLINE-5 6-DIONE 97 2,2'-BIPYRIDINE HYDROCHLORIDE 2,2'-Biquinoline 4,4'-Bipyridine 4,4'-Dipyridyl hydrate Bipyridine

  • 2,6'-Bipyridine
  • bpy
  • 2,2-Bispyridine
  • 2,2'-Dipyridyl p.a.
  • 2,2'-BIPYRIDINE (2,2'-Bipyridyl)
  • 2'-Bipyridine
  • 2,2-Dipyridyl 99+%, White Crystalline Powder, Reagent Grade
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  • 2,2'-Bipyridine, ACS, 98.0% min.
  • 2,2-Bipyridyl (2,2-Bipyridine)
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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-BIPYRIDYL
  • 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
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  • 2,2'-DIPYRIDYL, REAGENTPLUS, >=99%
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  • 2,2bipyridine, Bipyridine, Alpha, alphabipyridine, Alpha, alphabipyridyl, 2,2bipyridyl, CI-588, Alpha, alphadipyridyl, 2,2dipyridyl
  • 2,2'-Bipyridine,99+%BIPY
  • -Hydroxyphenyl)-2-butanone-d5 Oxime
  • -Bipyridyl, 2,3&rsquo