{(C12H8N2)((C6H5)3P)Cu(O2CC5H7N2)(H2O)}
A
1,10-Phenanthroline
Conditions | Yield |
---|---|
In acetone byproducts: CO2, H2O, PPh3; N2 bubbled through an acetone suspn. of the Cu-complex (0°C), low ratio Cu complex : acetone; | A n/a B 91% |
In solid byproducts: CO2, H2O, PPh3; maintained at 120°C under vac. (1E-2 Torr); |
Conditions | Yield |
---|---|
With copper(I) oxide; dmap; N-hydroxyphthalimide; oxygen In acetonitrile at 120℃; for 12h; Sealed tube; | 80% |
With potassium tert-butylate In o-xylene at 140℃; for 36h; Inert atmosphere; | 15% |
With platinum; oxygen In methanol at 40℃; under 750.075 Torr; Schlenk technique; Sealed tube; | 100 %Chromat. |
With tert.-butylhydroperoxide In water at 20℃; for 18h; Sealed tube; | 78 %Spectr. |
A
1,10-Phenanthroline
B
{Ru(1,10-phenanthroline)3}(NO3)2*2H2O
Conditions | Yield |
---|---|
With NaNO3 In methanol byproducts: AgCl; heated to reflux for 15 min; cooled, filtered, concd., addn. of an aq. soln. of NaNO3, pptn. filtered off, washed with diethyl ether, recrystn. (water or water-methanol 9:1); elem. anal.; | A n/a B 75% |
{Ag(1,10-phenanthroline)2}ClO4
A
1,10-Phenanthroline
Conditions | Yield |
---|---|
In methanol byproducts: AgCl; heated to reflux for 15 min; cooled, filtered, concd., addn. of an aq. soln. of NaClO4, pptn. filtered off, washed with diethyl ether, recrystn. (water or water-methanol 9:1); elem. anal.; | A n/a B 75% |
(Z)-1,2-di(2-bromopyridin-3-yl)ethene
1,10-Phenanthroline
Conditions | Yield |
---|---|
With copper In N,N-dimethyl-formamide for 5h; Ullmann coupling; Heating; | 67% |
5,6-epoxy-5,6-dihydro-[1,10]phenanthroline
1,10-Phenanthroline
Conditions | Yield |
---|---|
With 2,4,6-trimereaptotriazine, trisodium salt, nonahydrate In ethanol | 65% |
Conditions | Yield |
---|---|
With potassium hydroxide In ethanol for 8h; Sealed tube; Reflux; | 64% |
A
1,10-Phenanthroline
B
{Ru(1,10-phenanthroline)3}(NO3)2*2H2O
Conditions | Yield |
---|---|
With NaNO3 In methanol byproducts: AgCl; heated to reflux for 30 min; cooled, filtered, concd., addn. of an aq. soln. of NaNO3, pptn. filtered off, washed with diethyl ether, recrystn. (water or water-methanol 9:1); elem. anal.; | A n/a B 55% |
{Ag(1,10-phenanthroline)2}ClO4
A
1,10-Phenanthroline
Conditions | Yield |
---|---|
In methanol byproducts: AgCl; heated to reflux for 30 min; cooled, filtered, concd., addn. of an aq. soln. of NaClO4, pptn. filtered off, washed with diethyl ether, recrystn. (water or water-methanol 9:1); elem. anal.; | A n/a B 55% |
Conditions | Yield |
---|---|
With potassium hydroxide In ethanol at 80℃; for 8h; Schlenk technique; | 47% |
3-acetylpentane-2,4-dione
8-amino-7-quinolinecarbaldehyde
A
1,10-Phenanthroline
B
2-methyl-1,10-phenanthroline
Conditions | Yield |
---|---|
With potassium hydroxide In ethanol for 8h; Friedlaender reaction; Heating; | A 33% B 39% |
Conditions | Yield |
---|---|
With sulfuric acid; nitrobenzene | |
With sulfuric acid; orthoarsenic acid |
Conditions | Yield |
---|---|
With sulfuric acid; orthoarsenic acid; glycerol | |
With sulfuric acid; orthoarsenic acid; glycerol Reagens 4: HgCl2; |
1-methyl-1,10-phenanthrolinium iodide
1,10-Phenanthroline
Conditions | Yield |
---|---|
With sulfolane; triphenylphosphine at 151℃; Rate constant; |
n-Propyl-Radikal
A
1,10-Phenanthroline
B
propene
C
n-propylacetamide
D
4-propyl-[1,10]phenanthroline
Conditions | Yield |
---|---|
With tris(1,10-phenanthroline)iron(III) tris(hexafluorophosphate) In acetonitrile at 25℃; Rate constant; competition with BrCCL3, other complexes; |
n-propyltrimethyltin
acetonitrile
A
1,10-Phenanthroline
B
propene
C
n-propylacetamide
D
4-propyl-[1,10]phenanthroline
Conditions | Yield |
---|---|
With sodium hydroxide 1.) 22 deg C; Yield given. Multistep reaction. Yields of byproduct given; |
Isopropyl-trimethyl-stannane
acetonitrile
A
1,10-Phenanthroline
B
propene
C
N-isopropylacetamide
D
4-isopropyl-1,10-phenanthroline
Conditions | Yield |
---|---|
With sodium hydroxide 1.) 22 deg C; Yield given. Multistep reaction. Yields of byproduct given; |
Conditions | Yield |
---|---|
In water Rate constant; Equilibrium constant; Irradiation; HClO4, H2KPO4, Na2HPO4, Na2B2O7, NaOH, t-BuOH; |
Conditions | Yield |
---|---|
In water Rate constant; Equilibrium constant; Irradiation; HClO4, H2KPO4, Na2HPO4, Na2B2O7, NaOH, t-BuOH; |
n-propyltrimethyltin
A
1,10-Phenanthroline
B
propene
C
n-propylacetamide
D
4-propyl-[1,10]phenanthroline
Conditions | Yield |
---|---|
With sodium hydroxide 1.) acetonitrile, 22 deg C; Yield given. Multistep reaction. Yields of byproduct given; |
n-propyltrimethyltin
A
1,10-Phenanthroline
B
propene
C
n-propylacetamide
D
4-propyl-[1,10]phenanthroline
Conditions | Yield |
---|---|
With sodium hydroxide 1.) acetonitrile, 25 deg C; Yield given. Multistep reaction. Yields of byproduct given; |
n-propyltrimethyltin
A
1,10-Phenanthroline
B
propene
C
n-propylacetamide
D
4-propyl-[1,10]phenanthroline
Conditions | Yield |
---|---|
With sodium hydroxide 1.) acetonitrile, 25 deg C; Yield given. Multistep reaction. Yields of byproduct given; |
tetramethylstannane
A
1,10-Phenanthroline
B
4-methyl-1,10-phenanthroline
Conditions | Yield |
---|---|
With sodium hydroxide 1.) acetonitrile, 70 deg C, 2 h; Yield given. Multistep reaction; |
Ethyltrimethylstannan
A
4-ethyl-[1,10]phenanthroline
B
1,10-Phenanthroline
C
4-methyl-1,10-phenanthroline
D
N-ethylacetamide
Conditions | Yield |
---|---|
With sodium hydroxide 1.) acetonitrile, 22 deg C; Yield given. Multistep reaction. Yields of byproduct given; |
Ethyltrimethylstannan
acetonitrile
A
4-ethyl-[1,10]phenanthroline
B
1,10-Phenanthroline
C
4-methyl-1,10-phenanthroline
D
N-ethylacetamide
Conditions | Yield |
---|---|
With sodium hydroxide 1.) 22 deg C; Yield given. Multistep reaction. Yields of byproduct given; |
Isopropyl-trimethyl-stannane
A
1,10-Phenanthroline
B
propene
C
N-isopropylacetamide
D
4-isopropyl-1,10-phenanthroline
Conditions | Yield |
---|---|
With sodium hydroxide 1.) acetonitrile, 22 deg C; Yield given. Multistep reaction. Yields of byproduct given; |
Conditions | Yield |
---|---|
at 21.85℃; Equilibrium constant; |
Conditions | Yield |
---|---|
In ethanol; dichloromethane |
Conditions | Yield |
---|---|
With sulfuric acid; nitric acid at 160℃; for 3h; | 100% |
With sulfuric acid; nitric acid at 160℃; | 99% |
With sulfuric acid; nitric acid at 160℃; for 3h; | 99% |
1,10-Phenanthroline
1,10-phenanthroline-5,6-dione
Conditions | Yield |
---|---|
With sulfuric acid; nitric acid; sodium bromide at 90℃; for 2h; | 100% |
With sulfuric acid; nitric acid; potassium bromide at 130℃; for 3h; | 98.1% |
With sulfuric acid; nitric acid; potassium bromide at 95℃; for 3h; Cooling with ice; Sealed tube; Schlenk technique; | 97% |
1,10-Phenanthroline
1,3-dibromo-propane
6,7-dihydro-5H-[1,4]diazepino[1,2,3,4-l,m,n][1,10]phenanthroline-4,8-diium dibromide
Conditions | Yield |
---|---|
In chlorobenzene at 70 - 120℃; | 100% |
In nitrobenzene at 120℃; | 100% |
for 12h; Reflux; | 99% |
1,10-Phenanthroline
(bicyclo[2.2.1]hepta-2,5-diene)tetracarbonylmolybdenum(0)
A
(1,10-phenanthroline)molybdenum tetracarbonyl
B
bicyclo[2.2.1]hepta-2,5-diene
Conditions | Yield |
---|---|
In tetrahydrofuran reaction in a calorimeter under argon; | A 100% B n/a |
hydrogenchloride
1,10-Phenanthroline
potassium perrhenate
B
o-phenanthrolinium oxopentachlororhenate(V)
Conditions | Yield |
---|---|
With hydroquinone In acetic anhydride; acetic acid under N2 at room temp.; passing HCl gas through soln. of KReO4 in acetic acid and (Ac)2O till clear soln. (rhenate), mixed with hydroquinone inacetic acid, pptn. of KReOCl5, to mother liquor addn. of phenanthrolinen AcOH contg. (Ac)2O, pptn.; filtered, washed (acetic acid), kept in vacuo for 5 h; elem. anal.; | A 100% B 100% |
1,10-Phenanthroline
potassium perrhenate
o-phenanthrolinium oxopentachlororhenate(V)
Conditions | Yield |
---|---|
With hydroquinone In hydrogenchloride under N2 at room temp.; KReO4 suspended in concd. HCl, shaken, addn. ofhydroquinone in concd. HCl, yellow soln. obtained, addn. of phenanthroline, pptn.; filtered, washed (acetic acid), kept in vacuo for 5 h; | 100% |
Conditions | Yield |
---|---|
In tetrahydrofuran (Ar); stirring (5 h); washing (hexane), drying (vac.); elem. anal.; | 100% |
1,10-Phenanthroline
[ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2
chloro(p-cymene)(η2-1,10-phenanthroline-κ2N)ruthenium
Conditions | Yield |
---|---|
In dichloromethane at 20℃; for 3h; Inert atmosphere; Schlenk technique; | 100% |
In dichloromethane inert atm.; 2 equiv of phenanthroline was added to a suspn. of complex in CH2Cl2, the mixt. was stirred for 3 h at room temp.; evapd. to dryness, dissolved in water, filtered, evapd. to dryness; elem. anal.; | 99% |
In dichloromethane at 20℃; for 0.5h; | 51% |
1,10-Phenanthroline
Conditions | Yield |
---|---|
In toluene Ar atm.; stirring; concn., addn. of hexane, crystn. (-30°C, overnight), filtn., drying (vac., 40°C); | 100% |
1,10-Phenanthroline
tetrakis(actonitrile)copper(I) hexafluorophosphate
2,9-bis(2,6-dimethoxyphenyl)-3-ethynyl-[1,10]-phenanthroline
Cu(C12H6N2(C6H3(OCH3)2)2)(C12H8N2)(1+)*PF6(1-)=CuC40H32N4O4PF6
Conditions | Yield |
---|---|
In [D3]acetonitrile | 100% |
1,10-Phenanthroline
niobium pentafluoride
trimethylsilylazide
[Nb(N3)4(1,10-phen)2][Nb(N3)6]
Conditions | Yield |
---|---|
In acetonitrile at -196 - 20℃; for 6h; | 100% |
1,10-Phenanthroline
tantalum pentafluoride
trimethylsilylazide
[Ta(N3)4(1,10-phen)2][Ta(N3)6]
Conditions | Yield |
---|---|
In acetonitrile at -196 - 20℃; for 6h; | 100% |
1,10-Phenanthroline
tetrakis(actonitrile)copper(I) hexafluorophosphate
Conditions | Yield |
---|---|
In dichloromethane-d2 | 100% |
1,10-Phenanthroline
2-(6-(2,4,6-trimethylphenyl)pyridin-2-yl)-9-(2,4,6-trimethylphenyl)[1,10]phenanthroline
zinc trifluoromethanesulfonate
Conditions | Yield |
---|---|
In dichloromethane-d2; [D3]acetonitrile | 100% |
1,10-Phenanthroline
2-(6-(2,4,6-trimethylphenyl)pyridin-2-yl)-9-(2,4,6-trimethylphenyl)[1,10]phenanthroline
Conditions | Yield |
---|---|
In dichloromethane-d2; [D3]acetonitrile | 100% |
bromobenzene
1,10-Phenanthroline
6,7-dihydro-5H-[1,4]diazepino[1,2,3,4-lmn][1,10]phenanthroline-4,8-diium
Conditions | Yield |
---|---|
at 115℃; for 4h; | 100% |
1,10-Phenanthroline
Conditions | Yield |
---|---|
In dichloromethane at 20℃; for 30h; Inert atmosphere; Schlenk technique; | 100% |
1,10-Phenanthroline
Conditions | Yield |
---|---|
In dichloromethane for 30h; Inert atmosphere; Schlenk technique; | 100% |
Conditions | Yield |
---|---|
In dichloromethane at 20℃; for 1h; | 100% |
1,10-Phenanthroline
1,1,1,3,3,3-hexafluoro-2-phenylisopropyl alcohol
C30H37N3W
Conditions | Yield |
---|---|
Stage #1: 1,1,1,3,3,3-hexafluoro-2-phenylisopropyl alcohol; C30H37N3W In benzene at 20℃; for 0.5h; Stage #2: 1,10-Phenanthroline In benzene at 20℃; for 1h; | 100% |
1,10-Phenanthroline
Conditions | Yield |
---|---|
In water; N,N-dimethyl-formamide for 0.0833333h; | 100% |
Conditions | Yield |
---|---|
In acetonitrile at -196 - 20℃; for 16h; | 100% |
1,10-Phenanthroline
tris(p-trifluoromethylphenyl)phosphine gold bis(trifluoromethanesulfonyl)imidate
Conditions | Yield |
---|---|
In dichloromethane Inert atmosphere; | 100% |
1,10-Phenanthroline
Conditions | Yield |
---|---|
In dichloromethane Inert atmosphere; | 100% |
Conditions | Yield |
---|---|
In dichloromethane Inert atmosphere; | 100% |
1,10-Phenanthroline
[(Cy3P)Au]N(trifluoromethylsulfonyl)2
Conditions | Yield |
---|---|
In dichloromethane Inert atmosphere; | 100% |
1,10-Phenanthroline
(p-tolyl)3PAuN(trifluoromethanesulfonyl)2
Conditions | Yield |
---|---|
In dichloromethane Inert atmosphere; | 100% |
Conditions | Yield |
---|---|
In dichloromethane Inert atmosphere; | 100% |
1,10-Phenanthroline
[bis(trifluoromethanesulfonyl)imidate](triphenylphosphine)gold(I)
Conditions | Yield |
---|---|
In dichloromethane Inert atmosphere; | 100% |
1,10-Phenanthroline
A
tris(1,10-phenanthroline)iron(II) triflate
Conditions | Yield |
---|---|
In [D3]acetonitrile | A 100% B n/a |
The 1,10-Phenanthroline, with the CAS registry number 66-71-7 and EINECS registry number 200-629-2, has the systematic name of 1,10-o-Phenanthroline. And the molecular formula of this chemical is C12H8N2. It is a kind of off-white powder, and belongs to the following product categories: Industrial/Fine Chemicals; Heterocyclic Building Blocks; N-Containing.
The physical properties of 1,10-Phenanthroline are as following: (1)ACD/LogP: 2.25; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2.085; (4)ACD/LogD (pH 7.4): 2.244; (5)ACD/BCF (pH 5.5): 20.669; (6)ACD/BCF (pH 7.4): 29.861; (7)ACD/KOC (pH 5.5): 273.539; (8)ACD/KOC (pH 7.4): 395.176; (9)#H bond acceptors: 2; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 0; (12)Polar Surface Area: 25.78 Å2; (13)Index of Refraction: 1.74; (14)Molar Refractivity: 58.12 cm3; (15)Molar Volume: 144.113 cm3; (16)Polarizability: 23.041×10-24cm3; (17)Surface Tension: 61.295 dyne/cm; (18)Density: 1.25 g/cm3; (19)Flash Point: 164.756 °C; (20)Enthalpy of Vaporization: 58.73 kJ/mol; (21)Boiling Point: 365.089 °C at 760 mmHg; (22)Vapour Pressure: 0 mmHg at 25°C.
Preparation and uses of 1,10-Phenanthroline: It can be prepared by heating the o-phenylenediamine and glycerol, nitrobenzene and sulfuric acid. And it is often used as electroplating additives and analytical reagent. It is also used as redox indicator. What's more, it is used as reagent for the determination of iron, palladium, vanadium, copper and iron.
Chemical reaction: It is used in the synthesis of other chemicals. For example, it can react with butyllithium to produce 2,9-di-n-butyl-1,10-phenanthroline. This reaction will need reagent H2O, and the solvents MnO2 and toluene. The reaction time is 16 hours with temperature of 20°C, and the yield is about 62%.
You should be cautious while dealing with this chemical. It is toxic if swallowed. It is also very toxic to aquatic organisms, and may cause long-term adverse effects in the aquatic environment . Therefore, you had better take the following instructions: This material and/or its container must be disposed of as hazardous waste; Avoid release to the environment. Refer to special instructions safety data sheet; In case of accident or if you feel unwell, seek medical advice immediately (show label where possible).
You can still convert the following datas into molecular structure:
(1)SMILES: c1cc2ccc3cccnc3c2nc1
(2)InChI: InChI=1/C12H8N2/c1-3-9-5-6-10-4-2-8-14-12(10)11(9)13-7-1/h1-8H
(3)InChIKey: DGEZNRSVGBDHLK-UHFFFAOYAW
The toxicity data is as follows:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
mouse | LD50 | intraperitoneal | 75mg/kg (75mg/kg) | KIDNEY, URETER, AND BLADDER: OTHER CHANGES IN URINE COMPOSITION KIDNEY, URETER, AND BLADDER: OTHER CHANGES | Journal of Pharmacology and Experimental Therapeutics. Vol. 196, Pg. 478, 1976. |
mouse | LD50 | intravenous | 18mg/kg (18mg/kg) | Journal of Pharmacology and Experimental Therapeutics. Vol. 137, Pg. 1, 1962. |
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