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2,2'-Biquinoline
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Name

2,2'-Biquinoline

 EINECS 204-357-5
CAS No. 119-91-5 Density 1.223 g/cm3
PSA 25.78000 LogP 4.45000
Solubility Sparingly soluble in water (0.001g/L). Melting Point 192-195 °C(lit.)
Formula C18H12N2 Boiling Point 456.1 °C at 760 mmHg
Molecular Weight 256.307 Flash Point 203.6 °C
Transport Information N/A Appearance slightly yellow to light beige shiny flakes
Safety 26-37/39 Risk Codes 36/37/38
Molecular Structure Molecular Structure of 119-91-5 (2,2'-Biquinoline) Hazard Symbols IrritantXi
Synonyms

2,2'-Bichinoline;2,2'-Biquinolyl;2,2'-Diquinoline;2,2'-Diquinolyl;Cuproin;Cuproine;

Article Data 86

2,2'-Biquinoline Synthetic route

21948-80-1

2-(methylsulfinyl)quinoline

119-91-5

2,2'-biquinoline

Conditions
ConditionsYield
With methylmagnesium bromide In tetrahydrofuran for 0.5h; Ambient temperature; var. Grignard reag.;98%
612-62-4

2-Chloroquinoline

119-91-5

2,2'-biquinoline

Conditions
ConditionsYield
With potassium hydroxide In water; N,N-dimethyl-formamide at 35℃; for 24h; Ullmann Condensation; Inert atmosphere;97%
With bis(bipyridine)nickel(II) bromide; ethylene dibromide; sodium iodide In N,N-dimethyl-formamide at 20℃; for 2h; Electrochemical reaction; Inert atmosphere;91%
dibromobis(triphenylphosphine)nickel(II); tetraethylammonium iodide; zinc In tetrahydrofuran at 50℃; for 20h;84%
1613-37-2

Quinoline N-oxide

119-91-5

2,2'-biquinoline

Conditions
ConditionsYield
With potassium tert-butylate In N,N-dimethyl-formamide at 65℃; for 3.16667h; Solvent; Reagent/catalyst; Inert atmosphere; Schlenk technique;94%
With N,N-Dimethyltrimethylsilylamine; tetramethylammonium fluoride In N,N-dimethyl-formamide at 120℃; for 48h;70%
With potassium tert-butylate In tetrahydrofuran at 25℃; for 24h; Inert atmosphere;39%
91-22-5

quinoline

119-91-5

2,2'-biquinoline

Conditions
ConditionsYield
With 2,2,6,6-tetramethylpiperidinylmagnesium chloride; N,N,N,N,-tetramethylethylenediamine In toluene at 60℃; for 20h; Reagent/catalyst; Solvent; Temperature; Inert atmosphere;91%
With 2,2,6,6-tetramethyl-piperidine; N,N,N,N,-tetramethylethylenediamine; butyl magnesium bromide In tetrahydrofuran at 0 - 60℃; for 20h; Inert atmosphere;91%
Stage #1: quinoline With 3-chloro-benzenecarboperoxoic acid In 2-methyltetrahydrofuran at 40℃; for 6h; Inert atmosphere; Schlenk technique;
Stage #2: With 2,2'-azobis(isobutyronitrile); potassium tert-butylate In 2-methyltetrahydrofuran at 40 - 65℃; for 0.333333h; Inert atmosphere; Schlenk technique;		81%
6907-48-8

2,2’-biquinoline N-oxide

119-91-5

2,2'-biquinoline

Conditions
ConditionsYield
With lithium tetrafluoroborate In water; acetonitrile at 20℃; for 4h; Electrochemical reaction; Inert atmosphere;87%
With N,N-Dimethyltrimethylsilylamine In N,N-dimethyl-formamide at 120℃; for 48h;71%
With phosphorus trichloride for 3h; Inert atmosphere; Reflux;45%
With phosphorus trichloride In chloroform at 70℃; for 8h;

ammonium hexafluorophosphate

{Ru(II)(bpy)(biq)2}{PF6}2

75-05-8

acetonitrile

cis-{Ru(II)(bpy)(biq)(MeCN)2}{PF6}2

B

119-91-5

2,2'-biquinoline

Conditions
ConditionsYield
In water; acetone Irradiation (UV/VIS); (Ru(bpy)(biq)2)(PF6)2 dissolved in MeCN, violet soln. irradiated (Ar, stirred, 2 h), orange-brown soln., solvent removed, solid dissolved in acetone, 2,2'-biquinoline pptd. by addn. of H2O, filtered off, addn. of concd. aq. soln. of NH4PF6, pptn.; filtered, washed (H2O), dried (overnight, 80 ° C), elem. anal.;A 85%
B n/a
63469-73-8

1,1',2,2',3,3',4,4'-octahydro-2,2'-biquinoline

119-91-5

2,2'-biquinoline

Conditions
ConditionsYield
With C21H21ClIrNO2 In tetrahydrofuran; 2,2,2-trifluoroethanol for 20h; Inert atmosphere;81%
With tris(bipyridine)ruthenium(II) dichloride hexahydrate; chloropyridinecobaloxime(III); water at 30℃; for 48h; Schlenk technique; Inert atmosphere; Irradiation;79%
With iron oxide surrounded by nitrogen doped graphene shell immobilized on carbon support In n-heptane at 100℃; under 11251.1 Torr; for 12h; Autoclave;51%
6495-83-6

biquinoline N,N’-dioxide

119-91-5

2,2'-biquinoline

Conditions
ConditionsYield
With lithium tetrafluoroborate In water; acetonitrile at 20℃; for 4h; Electrochemical reaction; Inert atmosphere;75%
612-62-4

2-Chloroquinoline

4426-47-5

butylboronic acid

A

7661-39-4

2-n-butylquinoline

B

119-91-5

2,2'-biquinoline

Conditions
ConditionsYield
With potassium carbonate; bis(η3-allyl-μ-chloropalladium(II)); (1RS,2RS,3SR,4SR)-1,2,3,4-tetrakis((diphenylphosphanyl)methyl)cyclopentane In xylene at 130℃; for 20h; Suzuki cross-coupling;A 72%
B n/a
612-62-4

2-Chloroquinoline

A

91-22-5

quinoline

B

119-91-5

2,2'-biquinoline

Conditions
ConditionsYield
With 1,2-dimethoxyethane; NaH-tBuONa-Ni(OAc)2-PPh3 at 45℃; for 3h;A 22%
B 68%

2,2'-Biquinoline Chemical Properties

Molecular Structure of 2,2'-Biquinoline (CAS NO.135-48-8):

IUPAC Name: 2-quinolin-2-ylquinoline 
Empirical Formula: C18H12N2
Molecular Weight: 256.3013
H bond acceptors: 2
H bond donors: 0
Freely Rotating Bonds: 1
Polar Surface Area: 25.78 Å2
Index of Refraction: 1.72
Molar Refractivity: 82.71 cm3
Molar Volume: 209.3 cm3
Surface Tension: 57.4 dyne/cm
Density: 1.223 g/cm3
Flash Point: 203.6 °C
Enthalpy of Vaporization: 68.85 kJ/mol
Boiling Point: 456.1 °C at 760 mmHg
Vapour Pressure: 4.52E-08 mmHg at 25°C
Melting point: 192-195 °C(lit.)
BRN: 187259
EINECS: 204-357-5
Product Categories: Quinolinecarboxylic Acids, etc.; Quinolines
InChI
InChI=1/C18H12N2/c1-3-7-15-13(5-1)9-11-17(19-15)18-12-10-14-6-2-4-8-16(14)20-18/h1-12H
Smiles
c1(c2nc3c(cccc3)cc2)nc2c(cccc2)cc1

2,2'-Biquinoline Safety Profile

Hazard Codes: IrritantXi
Risk Statements: 36/37/38
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 26-36-37/39
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S36:Wear suitable protective clothing. 
S37/39:Wear suitable gloves and eye/face protection.
WGK Germany: 3
F: 8
HS Code: 29334990

2,2'-Biquinoline Specification

  2,2'-Biquinoline , with CAS number of 135-48-8, can be called 2,2'-Diquinolyl ; Cuproine ; Cuproin .

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