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| CAS No.: | 119-91-5 |
|---|---|
| Name: | 2,2'-Biquinoline |
| Molecular Structure: | |
|
|
|
| Formula: | C18H12N2 |
| Molecular Weight: | 256.307 |
| Synonyms: | 2,2'-Bichinoline;2,2'-Biquinolyl;2,2'-Diquinoline;2,2'-Diquinolyl;Cuproin;Cuproine; |
| EINECS: | 204-357-5 |
| Density: | 1.223 g/cm3 |
| Melting Point: | 192-195 °C(lit.) |
| Boiling Point: | 456.1 °C at 760 mmHg |
| Flash Point: | 203.6 °C |
| Solubility: | Sparingly soluble in water (0.001g/L). |
| Appearance: | slightly yellow to light beige shiny flakes |
| Hazard Symbols: |
 Xi
|
| Risk Codes: | 36/37/38 |
| Safety: | 26-37/39 |
| PSA: | 25.78000 |
| LogP: | 4.45000 |
2-(methylsulfinyl)quinoline
2,2'-biquinoline
| Conditions | Yield |
|---|---|
| With methylmagnesium bromide In tetrahydrofuran for 0.5h; Ambient temperature; var. Grignard reag.; | 98% |
| Conditions | Yield |
|---|---|
| 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% |
| Conditions | Yield |
|---|---|
| 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% |
| Conditions | Yield |
|---|---|
| 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% |
| Conditions | Yield |
|---|---|
| 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; |
| Conditions | Yield |
|---|---|
| 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 |
1,1',2,2',3,3',4,4'-octahydro-2,2'-biquinoline
2,2'-biquinoline
| Conditions | Yield |
|---|---|
| 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% |
| Conditions | Yield |
|---|---|
| With lithium tetrafluoroborate In water; acetonitrile at 20℃; for 4h; Electrochemical reaction; Inert atmosphere; | 75% |
2-Chloroquinoline
butylboronic acid
A
2-n-butylquinoline
B
2,2'-biquinoline
| Conditions | Yield |
|---|---|
| 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 |
| Conditions | Yield |
|---|---|
| With 1,2-dimethoxyethane; NaH-tBuONa-Ni(OAc)2-PPh3 at 45℃; for 3h; | A 22% B 68% |
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Molecular Structure of 2,2'-Biquinoline (CAS NO.135-48-8):
.png)
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
Hazard Codes: 
Xi
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 , with CAS number of 135-48-8, can be called 2,2'-Diquinolyl ; Cuproine ; Cuproin .
