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Home > Encyclopedia > 2,2′-Bipyridine

2,2′-Bipyridine

2,2′-Bipyridine structure

2,2′-Bipyridine 

structure
  • CAS No:

    366-18-7

  • Formula:

    C10H8N2

  • Chemical Name:

    2,2′-Bipyridine

  • Synonyms:

    2,2′-Bipyridine;α,α′-Bipyridyl;2,2′-Bipyridyl;α,α′-Dipyridyl;2,2′-Dipyridyl;α,α′-Bipyridine;2,2′-Dipyridine;α,α′-Dipyridine;2-(2-Pyridyl)pyridine;Dri-Rx 19LC-E;NSC 1550;NSC 615009;DryMax 2;2-Pyridin-2-ylpyridine;2-(Pyridin-2-yl)pyridine;XL-Dri

  • Categories:

    Biochemical Engineering  >  Biochemical Reagents

Description

White crystalline powder


DryPowder; PelletsLargeCrystals|WHITE CRYSTALS.


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.|A reagent used for the determination of iron.

2,2′-Bipyridine Basic Attributes

156.18

156.18

113089

206-674-4

551W113ZEP

0093

615009|1550

DTXSID9040635

White crystals|Crystals from dilute alcohol|PRISMS FROM PETROLEUM ETHER

29333999

Characteristics

25.8

1.7

White to almost white Crystalline Powder

1.1±0.1 g/cm3

72 °C

273.5 °C

121 °C

1.581

H2O: 5.5 g/L 22 ºC

Store at RT.

Oral-rat LD50: 100 mg/kg; Abdominal cavity-mouse LD50:200 mg/kg

Flammable; burning produces toxic nitrogen oxide fumes

pKa = 4.33 (conjugate acid)

Dust explosion possible if in powder or granular form, mixed with air.

Safety Information

III

6.1

UN 2811 6.1/PG 3

3

25-36/37/38-20/21-23/24/25-21

36/37-45-36/37/39-26

DW1750000

T,Xi

Treasury is ventilated, low temperature and dry; stored separately from food materials

Irritant

Stable. Incompatible with strong oxidizing agents, most common metals. May be light sensitive.

P280-P301 + P310-P312

H301 + H311

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

Combustible. Gives off irritating or toxic fumes (or gases) in a fire. Finely dispersed particles form explosive mixtures in air.

|Danger|H301+H311 (10.58%): Toxic if swallowed or in contact with skin [Danger Acute toxicity, oral; acute toxicity, dermal]|P264, P270, P273, P280, P301+P310, P301+P312, P302+P352, P305+P351+P338, P312, P321, P322, P330, P337+P313, P361, P363, P405, and P501|Aggregated GHS information provided by 511 companies from 22 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H301: Toxic if swallowed [Danger Acute toxicity, oral]|P260, P264, P270, P301+P310, P309+P311, P321, P330, P405, and P501|P260, P264, P270, P280, P301+P310, P302+P352, P305+P351+P338, P309+P311, P312, P314, P321, P322, P330, P337+P313, P361, P363, P405, and P501

Use water spray, alcohol-resistant foam, dry powder, carbon dioxide.

Depending on the extent of possible contact, workers should be provided with personal protective equipment. A charcoal gas mask canister respirator has been found to be effective against a 2% pyridine concentration at 30 l/min for 1 hr. Rubber and plastic gloves should not be relied upon to prevent skin contact because pyridine and many of its derivatives penetrate these materials ... . /Pyridine, homologs, and derivatives/

SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.

Pyridine and its derivatives cause local irritation on contact with the skin, mucous membranes and cornea. /Pyridine and its derivatives/

Personal protection: particulate filter respirator adapted to the airborne concentration of the substance. Sweep spilled substance into covered containers. If appropriate, moisten first to prevent dusting. Carefully collect remainder. Then store and dispose of according to local regulations.

Separated from strong oxidants.

A nuisance-causing concentration of airborne particles can be reached quickly when dispersed.

The substance is irritating to the eyes, skin and respiratory tract.

NO open flames. Closed system, dust explosion-proof electrical equipment and lighting. Prevent deposition of dust.

PREVENT DISPERSION OF DUST!

Use ventilation (not if powder).

Protective gloves.

Wear safety spectacles.

Toxicity

highly toxic

2,2'-BIPYRIDINE AT CONCENTRATIONS OF 1.0-5.0 MILLIMOLE GREATLY INCREASED THE COVALENT BINDING OF (14)C-LABELED CARBON TETRACHLORIDE TO RAT LIVER MICROSOMES.|BIOTRANSFORMATION OF M-FLUOROTYROSINE BY TYROSINE METABOLIC PATHWAY OF THE LIVER PLAYED AN IMPORTANT ROLE IN THE ELICITATION OF CONVULSIONS IN MICE BY M-FLUOROTYROSINE. SIMULTANEOUS ADMINISTRATION OF M-FLUOROTYROSINE & ALPHA,ALPHA-DIPYRIDYL PREVENTED THE APPEARANCE OF M-FLUOROTYROSINE INDUCED SEIZURES.

LD50 Rat oral 256 mg/kg|LD50 Rat sc 155 mg/kg|LD50 Rat oral 100 mg/kg|LD50 Rat ip 150 mg/kg|For more Non-Human Toxicity Values (Complete) data for 2,2'-BIPYRIDINE (6 total), please visit the HSDB record page.

2,2'-Bipyridine's use in the production of the herbicide, diquat(1), may result in its direct release to the environment or in its release to the environment through various waste streams(SRC).

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 160(SRC), determined from a log Kow of 1.5(2) and a regression-derived equation(3), indicates that 2,2'-bipyridine is expected to have moderate mobility in soil(SRC). Volatilization of 2,2'-bipyridine from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 5.4X10-10 atm-cu m/mole(4). 2,2'-Bipyridine is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 1.3X10-5 mm Hg(SRC), derived from a water solubility, 5.9X10+3 mg/l(5), and its estimated Henry's Law constant(4).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 160(SRC), determined from a log Kow of 1.5(2) and a regression-derived equation(3), indicates that 2,2'-bipyridine is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 5.4X10-10 atm-cu m/mole(4). According to a classification scheme(5), an estimated BCF of 3(SRC), from its log Kow(2) and a regression-derived equation(6), suggests the potential for bioconcentration in aquatic organisms is low(SRC). 2,2'-Bipyridine was shown to undergo slow oxidation with photochemically generated hydroxyl radicals in aqueous solution (half-life of about 129 days)(7).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 2,2'-bipyridine, which has an estimated vapor pressure of 1.3X10-5 mm Hg at 25 °C(SRC), derived from a water solubility, 5.9X10+3 mg/l(2), and an estimated Henry's Law constant, 5.3X10-10 atm-cu m/mole(3), will exist in both the vapor and particulate phases in the ambient atmosphere(SRC). Vapor-phase 2,2'-bipyridine is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 12.5 days(SRC), calculated from its rate constant of 1.3X10-12 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(4). Particulate-phase 2,2'-bipyridine may be removed from the air by wet and dry deposition(SRC).

The rate constant for the vapor-phase reaction of 2,2'-bipyridine with photochemically-produced hydroxyl radicals has been estimated as 1.3X10-12 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 12 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). The rate constant for the reaction of 2,2'-bipyridine with photochemically-produced hydroxyl radicals in water has been measured to be 6.2X10+9 M-1 sec-1 at 21 °C and a pH of 9.3(2), which corresponds to an aqueous half-life of about 129 days at a hydroxyl radical concn of 1X10-17 M(3). 2,2'-Bipyridine is not expected to undergo hydrolysis in the environment due to the lack of hydrolyzable functional groups(4). Data are not available to assess this compound's potential for direct photolysis.

According to a classification scheme(1), an estimated BCF of 3(SRC), from its water solubility(2) and a regression-derived equation(3), suggests the potential for bioconcentration in aquatic organisms is low(SRC).

39.81 L/kg|The Koc of 2,2'-bipyridine is estimated as 160(SRC), using a log Kow of 1.5(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that 2,2'-bipyridine is expected to have moderate mobility in soil(SRC).

The Henry's Law constant for 2,2'-bipyridine is estimated as 5.4X10-10 atm-cu m/mole(1). This Henry's Law constant indicates that 2,2'-bipyridine is expected to be essentially nonvolatile from water surfaces(2). 2,2'-Bipyridine is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 1.3X10-5 mm Hg(SRC), derived from its water solubility, 5.9X10+3 mg/l(3), and an estimated Henry's Law constant(1).

NIOSH (NOES Survey 1981-1983) has statistically estimated that 3,684 workers (886 of these are female) are potentially exposed to 2,2'-bipyridine in the US(1). Occupational exposure to 2,2'-bipyridine may occur by dermal contact with this compound at workplaces where 2,2'-bipyridine is produced or used(SRC).

Drug Information

Substances used for the detection, identification, analysis, etc. of chemical, biological, or pathologic processes or conditions. Indicators are substances that change in physical appearance, e.g., color, at or approaching the endpoint of a chemical titration, e.g., on the passage between acidity and alkalinity. Reagents are substances used for the detection or determination of another substance by chemical or microscopical means, especially analysis. Types of reagents are precipitants, solvents, oxidizers, reducers, fluxes, and colorimetric reagents. (From Grant and Hackh's Chemical Dictionary, 5th ed, p301, p499) (See all compounds classified as Indicators and Reagents.)|Chemicals that bind to and remove ions from solutions. Many chelating agents function through the formation of COORDINATION COMPLEXES with METALS. (See all compounds classified as Chelating Agents.)

PYRIDINE & ITS ALKYL DERIVATIVES ARE ABSORBED FROM GI TRACT, INTRAPERITONEAL CAVITY & LUNGS. PERITONEAL ABSORPTION IS APPARENTLY ONLY SLIGHTLY MORE RAPID & COMPLETE THAN GI ABSORPTION ... IN GENERAL THE BASES ARE RAPIDLY ABSORBED THROUGH INTACT SKIN. /ALKYL DERIVATIVES OF PYRIDINE/

2,2'-BIPYRIDINE INHIBITED AROMATIC HYDROXYLATION IN MICROSOMES DERIVED FROM 3-METHYLCHOLANTHRENE TREATED RATS & ENHANCED THIS PROCESS IN MICROSOMES FROM PHENOBARBITAL SODIUM TREATED RATS. 2,2'-BIPYRIDINE PRODUCED A TYPE I BINDING SPECTRUM WITH AEROBIC MICROSOMAL FRACTIONS FROM PHENOBARBITAL SODIUM TREATED RATS & A TYPE II BINDING SPECTRUM WITH MICROSOMES FROM 3-METHYLCHOLANTHRENE TREATED RATS.

2,2'-DIPYRIDYL, A CHELATOR OF IRON(+2) & INHIBITOR OF PLATELET AGGREGATION WAS STUDIED TO DETERMINE THE MECHANISM OF ITS EFFECTS ON PLATELETS. AT LOW CONCENTRATIONS REQUIRED TO INHIBIT ARACHIDONIC ACID-MEDIATED AGGREGATION, 2,2'-DIPYRIDYL & 4,4'DIPYRIDYL-2HCL INHIBITED THE PLATELET CYCLOOXYGENASE. THE MECHANISM OF INHIBITION OF ADP-INDUCED AGGREGATION WAS INDUCED AGGREGATION, 2,2'-DIPYRIDYL DID NOT ALTER CELL ULTRASTRUCTURE, SEROTONIN OR NUCLEOTIDE CONTENT, OR INTERFERE WITH RELEASE OF ARACHIDONIC ACID-(14)C OR CALCIUM MOVEMENTS. APPARENTLY, THE INHIBITION OF CYCLOOXYGENASE BY LOW CONCENTRATIONS OF THESE COMPOUNDS IS NOT DUE TO BIDENTATE IRON CHELATION, SINCE 4,4'-DIPYRIDYL WAS ALMOST AS EFFECTIVE AS 2,2'-DIPYRIDYL, BUT IS COMPATIBLE WITH BINDING OF THESE INHIBITORS TO THE FE IN THE HEME OF THE CYCLOOXYGENASE.

Fresh air, rest.


Rinse and then wash skin with water and soap.


First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

/SRP:/ Basic treatment: Establish a patent airway. Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if necessary. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with normal saline during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 ml/kg up to 200 ml of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool. Administer activated charcoal ... . /Aromatic hydrocarbons and related compounds/|/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious or in respiratory arrest. Positive pressure ventilation techniques with a bag valve mask device may be beneficial. Monitor cardiac rhythm and treat arrhythmias if necessary ... Start an IV with D5W /SRP: "To keep open", minimal flow rate/. Use lactated Ringer's if signs of hypovolemia are present. Watch for signs of fluid overload. Consider drug therapy for pulmonary edema ... . Treat seizures with diazepam (Valium) ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Aromatic hydrocarbons and related compounds/

2,2 Bipyridine

The substance can be absorbed into the body by inhalation and by ingestion.

Cough. Sore throat.


Redness. Pain.


Redness. Pain.

2,2′-Bipyridine Use and Manufacturing

Methods of Manufacturing

Derived from pyridine and ferric chloride. Mix 70g of anhydrous pyridine with 13g of anhydrous ferric chloride, heat at 300°C in a sealed tube for about 35h. After cooling, the reaction solidified into red-black crystals, opened the sealed tube, and washed out the red-black solution of the solid with a small amount of hot water. Extract with ether to remove oily impurities. After neutralization with sodium bicarbonate, excess pyridine was removed with steam heating. The mixture was then made strongly alkaline and 2, 2'-bipyridine was distilled off with steam. The distillate was acidified, evaporated and concentrated, then added sodium hydroxide, extracted with ether, and the ether was removed to obtain a crude product. The crude product is recrystallized with B and the activated carbon is decolorized to obtain the pure product. In addition, the product can also be prepared by the reaction of α-picoline [109-06-8] with potassium permanganate and purification treatment.

Uses

As a reagent for the determination of iron.


Adhesives and sealant chemicals


Adhesives and sealants

Production

25,000 - 100,000 lb

GRADE: REAGENT.

Paint and coating manufacturing|2,2'-Bipyridine: ACTIVE

VARIOUS THIN LAYER CHROMATOGRAPHIC METHODS FOR SEPARATION & IDENTIFICATION OF 2-, 3-, & 4-SUBSTITUTED PYRIDINES ARE DESCRIBED.|CONCN CAN BE DETERMINED IN AIR BY COLLECTION IN DISTILLED WATER & MEASUREMENT OF ... UV ABSORPTION SPECTRUM.

Computed Properties

Molecular Weight:156.18
XLogP3:1.7
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:1
Exact Mass:156.068748264
Monoisotopic Mass:156.068748264
Topological Polar Surface Area:25.8
Heavy Atom Count:12
Complexity:120
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Price Analysis

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