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4,4'-Bipyridine
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Name

4,4'-Bipyridine

 EINECS 209-036-3
CAS No. 553-26-4 Density 1.106 g/cm3
PSA 25.78000 LogP 2.14360
Solubility slightly soluble in water Melting Point 109-112 °C(lit.)
Formula C10H8N2 Boiling Point 304.8 °C at 760 mmHg
Molecular Weight 156.187 Flash Point 104.3 °C
Transport Information N/A Appearance off-white to tan powder
Safety 26-36/37/39-45 Risk Codes 25-36/37/38-20/21-23/24/25
Molecular Structure Molecular Structure of 553-26-4 (4,4'-Bipyridine) Hazard Symbols ToxicT,IrritantXi
Synonyms

4,4'-Bipyridyl;4,4'-Dipyridine;4,4'-Dipyridyl;4-(4-Pyridyl)pyridine;IK 12;NSC 404423;SERS420;g,g'-Bipyridyl;g,g'-Dipyridyl;

Article Data 128

4,4'-Bipyridine Synthetic route

(4,4′-bipyridine){Ti(N[tBu](3,5-Me2C6H3))3}2

7553-56-2

iodine

A

553-26-4

4,4'-bipyridine

B

ITi(N[tBu](3,5-Me2C6H3))3

Conditions
ConditionsYield
In tetrahydrofuran for 0.5h; Inert atmosphere; Schlenk technique; Glovebox;A n/a
B 100%
24573-15-7

4,4'-bipyridine N,N'-dioxide

553-26-4

4,4'-bipyridine

Conditions
ConditionsYield
With titanium tetrachloride; tin(ll) chloride In benzene for 0.5h; Ambient temperature;98%
With titanium In tetrahydrofuran for 0.25h; Ambient temperature;97%
With titanium tetrachloride; sodium iodide In acetonitrile at 20℃; for 0.0333333h;95%
With sodium hypophosphite; palladium on activated charcoal In acetic acid at 60℃; for 1h;92%
With sodium hydroxide; thiourea S,S-dioxide In ethanol at 80 - 85℃; for 1.5h;81%
39182-30-4

4,4'-bipyridine N-monoxide

553-26-4

4,4'-bipyridine

Conditions
ConditionsYield
With titanium tetrachloride; tin(ll) chloride In benzene for 0.5h; Ambient temperature;96%
With titanium In tetrahydrofuran for 0.25h; Ambient temperature;94%
7379-35-3

4-chlorpyridine hydrochloride

553-26-4

4,4'-bipyridine

Conditions
ConditionsYield
With potassium hydroxide In water; N,N-dimethyl-formamide at 35℃; for 12h; Ullmann Condensation; Inert atmosphere;95%
19524-06-2

4-bromopyridine hydrochloride

553-26-4

4,4'-bipyridine

Conditions
ConditionsYield
With bis(benzonitrile)palladium(II) dichloride; Tetrakis(dimethylamino)ethylen In N,N-dimethyl-formamide at 50℃; for 6h;92%
With Tetrakis(dimethylamino)ethylen; bis(benzonitrile)palladium(II) dichloride In N,N-dimethyl-formamide at 50℃; for 6h;52%
1120-87-2

4-bromopyridin

553-26-4

4,4'-bipyridine

Conditions
ConditionsYield
With tetraethylammonium tosylate; bis-triphenylphosphine-palladium(II) chloride In N,N-dimethyl-formamide Ambient temperature; electrolysis;91%
With indium; lithium chloride; palladium diacetate In N,N-dimethyl-formamide at 100℃; for 2.5h;90%
With manganese; zirconocene dichloride; (Me)2Dipyr(H)2*NiCl2; lithium chloride In 1,2-dimethoxyethane at 20℃; for 72h; Inert atmosphere;87%
1692-15-5

4-pyridylboronic acid

553-26-4

4,4'-bipyridine

Conditions
ConditionsYield
With potassium phosphate In 1,4-dioxane at 85℃; for 3h; Catalytic behavior; Suzuki Coupling; Green chemistry;88%
With Cu(OH)x has been encapsulated over montmorillonite-KSF; air In methanol at 20℃; for 0.666667h; Green chemistry;81%
With potassium acetate; silver(l) oxide In methanol at 40℃; for 36h;78%
116008-37-8

sodium pyridine-4-sulfinate

553-26-4

4,4'-bipyridine

Conditions
ConditionsYield
With di-tert-butyl peroxide; palladium diacetate In acetonitrile at 60℃; for 12h;88%
626-61-9

4-Chloropyridine

A

110-86-1

pyridine

B

553-26-4

4,4'-bipyridine

Conditions
ConditionsYield
With 1,2-dimethoxyethane; NaH-tBuONa-Ni(OAc)2-PPh3 at 45℃; for 2h;A 10 % Chromat.
B 86%
626-61-9

4-Chloropyridine

553-26-4

4,4'-bipyridine

Conditions
ConditionsYield
With nickel diacetate; triphenylphosphine; sodium t-butanolate In 1,2-dimethoxyethane at 45℃; for 2h;86%
With triphenylphosphine; nickel dichloride; zinc In N,N-dimethyl-formamide at 50℃; for 5h;82%
With triphenylphosphine; nickel dichloride; zinc In N,N-dimethyl-formamide at 50℃; for 5h;82%
With potassium phosphate tribasic heptahydrate; chloro(2-dicyclohexylphosphino-2’,4’,6’-triisopropyl-1,1‘-biphenyl)[2-(2’-amino-1,1‘-biphenyl’)]palladium(II); bis(pinacol)diborane; XPhos In ethanol at 20℃; for 8h;72%
With N-benzyl-N,N,N-triethylammonium chloride; sodium formate; palladium on charcoal In methanol; water

4,4'-Bipyridine Consensus Reports

Reported in EPA TSCA Inventory.

4,4'-Bipyridine Specification

1.Introduction of 4,4'-Bipyridine

The 4,4'-Bipyridine is an organic compound with the formula C10H8N2. The IUPAC name of this chemical is 4-pyridin-4-ylpyridine. With the CAS registry number 553-26-4, it is also named as 4-(4-pyridyl)pyridine. The product's categories are Pyridines; Pyridines Derivates; Pyridine; Viologens (Photochromic, Related Compounds); Functional Materials; Photochromic Compounds. Besides, it is an off-white to tan powder, which should be stored in a closed cool and dry palce. It is a pharmaceutical intermediate, which is used for organic synthesis.

2.Physical properties of 4,4'-Bipyridine

(1)ACD/LogP: 1.20; (2)ACD/LogD (pH 5.5): 1.2; (3)ACD/LogD (pH 7.4): 1.2; (4)ACD/BCF (pH 5.5): 4.82; (5)ACD/BCF (pH 7.4): 4.84; (6)ACD/KOC (pH 5.5): 107.06; (7)ACD/KOC (pH 7.4): 107.68; (8)#H bond acceptors: 2; (9)#Freely Rotating Bonds: 1; (10)Polar Surface Area: 25.78 Å2; (11)Index of Refraction: 1.58; (12)Molar Refractivity: 47.02 cm3; (13)Molar Volume: 141.1 cm3; (14)Polarizability: 18.64×10-24cm3; (15)Surface Tension: 46.6 dyne/cm; (16)Density: 1.106 g/cm3; (17)Flash Point: 104.3 °C; (18)Enthalpy of Vaporization: 52.34 kJ/mol; (19)Boiling Point: 304.8 °C at 760 mmHg; (20)Vapour Pressure: 0.00154 mmHg at 25°C.

3.Structure descriptors of 4,4'-Bipyridine

(1)Canonical SMILES: C1=CN=CC=C1C2=CC=NC=C2
(2)InChI: InChI=1S/C10H8N2/c1-5-11-6-2-9(1)10-3-7-12-8-4-10/h1-8H
(3)InChIKey: MWVTWFVJZLCBMC-UHFFFAOYSA-N
 

4. Preparation of 4,4'-Bipyridine

The 4,4'-Bipyridine can be prepared by 4-chloro-pyridine. This reaction will need reagent NiCl2, P(Ph)3, Zn and solvent dimethylformamide. The reaction time is 5 hours with reaction temperature of 82 °C. The yield is about 50%.



5. Uses of 4,4'-Bipyridine

4,4'-Bipyridine can be used to produce [4,4']bipyridyl-2,2'-diyldiamine at temperature of 200 °C. It will need reagent cumene and sodium amide.

6.Safety informatino of 4,4'-Bipyridine

It is harmful by inhalation and in contact with skin and toxic by inhalation, in contact with skin and if swallowed. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. Besides, this chemical is irritating to eyes, respiratory system and skin. When you are using it, wear suitable gloves and eye/face protection. In case of accident or if you feel unwell seek medical advice immediately (show the label where possible).

7.The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
rat LD50 oral 172mg/kg (172mg/kg) SENSE ORGANS AND SPECIAL SENSES: LACRIMATION: EYE

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

LUNGS, THORAX, OR RESPIRATION: DYSPNEA		 Journal of Toxicology and Environmental Health. Vol. 10, Pg. 363, 1982.

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