66-71-7

Basic information

• Product Name: o-Phenanthroline
• Synonyms: O-PHENANTHROLINE;ORTHOPHENANTHROLINE;1,10-Fenanthrolin;1,10-o-Phenanthroline;4,5-Diazaphenanthrene;4,5-Phenanthroline;Activ-8 in hexylene glycol;beta-Phenanthroline
• CAS NO: 66-71-7
• Molecular Formula: C₁₂H₈N₂
• Molecular Weight: 180.21
• EINECS: 200-629-2
• Product Categories: Industrial/Fine Chemicals;Heterocyclic Building Blocks;N-Containing;Others;organic amine;Aromatics;Chelating Agents & Ligands;Heterocycles;Py-N;Achiral Nitrogen
• Mol File: 66-71-7.mol
• Article Data: 43

Chemical Properties

• Melting Point: 114-117 °C(lit.)
• Boiling Point: >330°C
• Flash Point: >330°C
• Appearance: White to light yellow or light pink/Powder
• Density: 1.1836 (rough estimate)
• Refractive Index: 1.5200 (estimate)
• Storage Temp.: Refrigerator
• Solubility: 2.69g/l
• PKA: 4.84(at 25℃)
• Water Solubility: slightly soluble
• Sensitive: Hygroscopic
• Stability: Stable. Hygroscopic. Store under nitrogen. Incompatible with strong acids, strong oxidizing agents.
• Merck: 14,7214
• BRN: 126461
• CAS DataBase Reference: o-Phenanthroline(CAS DataBase Reference)
• NIST Chemistry Reference: o-Phenanthroline(66-71-7)
• EPA Substance Registry System: o-Phenanthroline(66-71-7)

Safety Data

• Hazard Codes: T,N
• Statements: 25-50/53
• Safety Statements: 45-60-61
• RIDADR: UN 2811 6.1/PG 3
• WGK Germany: 3
• RTECS: SF8437000
• TSCA: Yes
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 66-71-7(Hazardous Substances Data)

Usage

Description

o-Phenanthroline is an organic intermediate, white crystalline powder. It is a redox indicator, a reagent for the determination of ferrous, palladium, vanadium, copper and iron.

Chemical Properties

off-white powder

Characteristics

o-Phenanthroline can form complexes with a variety of transition metals. Since the complexes formed are chelates, they are relatively stable. The complexes and their derivatives formed with copper can be used as non-oxidative nucleic acid cleaving enzymes because they have certain cleavage activity on DNA, and further have certain anticancer activities.

Uses

Different sources of media describe the Uses of 66-71-7 differently. You can refer to the following data:
1. A chelating agent, forming complexes with most metal ions.
2. A ligand employed in the spectrophotometric determination of metals and photocatalytic reduction of carbon dioxide.
3. As an analytical reagent for determination of metals in chemical and biological systems through complex formation. As an indicator ("Ferroin") in combination with ferrous ions for oxidation/reduction reactions. In organic syntheses as an activator.

Safety Profile

Poison by ingestion and intraperitoneal routes. An experimental teratogen. Mutation data reported. When heated to decomposition it emits toxic fumes of NOx.

in vitro

proteolysis of lamins, which are the intermediate filament proteins providing support to the nuclear structural proteins and are targets of mmp-2, o-phenanthroline abolished the proteolysis of lamin a [2].

Purification Methods

Purify it via the HgCl2 addition compound formed when phenanthridine (20g) in 1:1 HCl (100mL) is added to aqueous HgCl2 (60g in 3L), and the mixture is heated to boiling. The HgCl2 complex separates as yellow red crystals with m 195-198o [Arcus & Mesley J Chem Soc 1780 1953]. Conc HCl is then added until all of the solid has dissolved. The compound separates on cooling and is decomposed with aqueous NaOH (ca 5M). Phenanthridine is extracted into Et2O, evaporated, and the residue is crystallised from pet ether (b 80-100o) or EtOAc. [Cumper et al. J Chem Soc 45218 1962.] It is also purified by chromatography on activated alumina from *benzene solution, with diethyl ether as eluent. Evaporation of ether gives crystalline material which is freed from residual solvent under vacuum, then further purified by fractional crystallisation, under N2, from its melt. It was purified by zone melting and sublimes in a vacuum. The picrate has m 218.5-219.5o (from iso-PrOH) (also reported are m 244-245o and 247-248o, from EtOH or H2O). [Slough & Ubbelhode J Chem Soc 911 1957.] [Beilstein 20 H 466, 20 III/IV 4016, 20/8 V 223.]

InChI:InChI=1/C12H8N2/c1-3-9-5-6-10-4-2-8-14-12(10)11(9)13-7-1/h1-8H

Synthetic route

{(C12H8N2)((C6H5)3P)Cu(O2CC5H7N2)(H2O)} (122108-94-5) → 1,10-Phenanthroline (66-71-7) + {copper(I)-3,5-dimethylpyrazolate}(n)

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);

1,2,3,4-tetrahydro-1,10-phenanthroline (3188-84-9) → 1,10-Phenanthroline (66-71-7)

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.

[Ru(1,10-phenanthroline)2Cl2] + di (1,10-phenanthroline)silver(I) nitrate → 1,10-Phenanthroline (66-71-7) + {Ru(1,10-phenanthroline)3}(NO3)2*2H2O (14126-11-5)

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%

[Ru(1,10-phenanthroline)2Cl2] + {Ag(1,10-phenanthroline)2}ClO4 (58034-59-6) + sodium perchlorate → 1,10-Phenanthroline (66-71-7) + {Ru(phan)3}(ClO4)2*H2O

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 (942267-02-9) → 1,10-Phenanthroline (66-71-7)

Conditions	Yield
With copper In N,N-dimethyl-formamide for 5h; Ullmann coupling; Heating;	67%

5,6-epoxy-5,6-dihydro-[1,10]phenanthroline (65115-91-5) → 1,10-Phenanthroline (66-71-7)

Conditions	Yield
With 2,4,6-trimereaptotriazine, trisodium salt, nonahydrate In ethanol	65%

2,3-dinitrobenzene-1,4-dicarbaldehyde + acetaldehyde (75-07-0) → 1,10-Phenanthroline (66-71-7)

Conditions	Yield
With potassium hydroxide In ethanol for 8h; Sealed tube; Reflux;	64%

ruthenium(III) chloride trihydrate + di (1,10-phenanthroline)silver(I) nitrate → 1,10-Phenanthroline (66-71-7) + {Ru(1,10-phenanthroline)3}(NO3)2*2H2O (14126-11-5)

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%

ruthenium(III) chloride trihydrate + {Ag(1,10-phenanthroline)2}ClO4 (58034-59-6) + sodium perchlorate → 1,10-Phenanthroline (66-71-7) + {Ru(phan)3}(ClO4)2*H2O

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%

2,3-diaminobenzene-1,4-dicarbaldehyde + acetaldehyde (75-07-0) → 1,10-Phenanthroline (66-71-7)

Conditions	Yield
With potassium hydroxide In ethanol at 80℃; for 8h; Schlenk technique;	47%

3-acetylpentane-2,4-dione (815-68-9) + 8-amino-7-quinolinecarbaldehyde (158753-17-4) → 1,10-Phenanthroline (66-71-7) + 2-methyl-1,10-phenanthroline (3002-77-5)

Conditions	Yield
With potassium hydroxide In ethanol for 8h; Friedlaender reaction; Heating;	A 33% B 39%

8-amino quinoline (578-66-5) → 1,10-Phenanthroline (66-71-7)

1,2-diamino-benzene (95-54-5) + glycerol (56-81-5) → 1,10-Phenanthroline (66-71-7)

Conditions	Yield
With sulfuric acid; nitrobenzene
With sulfuric acid; orthoarsenic acid

1,2-diamino-benzene (95-54-5) → 1,10-Phenanthroline (66-71-7)

Conditions	Yield
With sulfuric acid; orthoarsenic acid; glycerol
With sulfuric acid; orthoarsenic acid; glycerol Reagens 4: HgCl2;

1-methyl-1,10-phenanthrolinium iodide (23647-26-9) → 1,10-Phenanthroline (66-71-7)

Conditions	Yield
With sulfolane; triphenylphosphine at 151℃; Rate constant;

n-Propyl-Radikal (2143-61-5) → 1,10-Phenanthroline (66-71-7) + propene (187737-37-7) + n-propylacetamide (5331-48-6) + 4-propyl-[1,10]phenanthroline (80186-77-2)

Conditions	Yield
With tris(1,10-phenanthroline)iron(III) tris(hexafluorophosphate) In acetonitrile at 25℃; Rate constant; competition with BrCCL3, other complexes;

n-propyltrimethyltin (3531-45-1) + acetonitrile (75-05-8) → 1,10-Phenanthroline (66-71-7) + propene (187737-37-7) + n-propylacetamide (5331-48-6) + 4-propyl-[1,10]phenanthroline (80186-77-2)

Conditions	Yield
With sodium hydroxide 1.) 22 deg C; Yield given. Multistep reaction. Yields of byproduct given;

Isopropyl-trimethyl-stannane (3531-46-2) + acetonitrile (75-05-8) → 1,10-Phenanthroline (66-71-7) + propene (187737-37-7) + N-isopropylacetamide (1118-69-0) + 4-isopropyl-1,10-phenanthroline (80186-78-3)

Conditions	Yield
With sodium hydroxide 1.) 22 deg C; Yield given. Multistep reaction. Yields of byproduct given;

perfluorobenzaldehyde (653-37-2) + C12H9N2 (66-71-7) → 1,10-Phenanthroline (66-71-7) + C7HF5O(1-)

Conditions	Yield
In water Rate constant; Equilibrium constant; Irradiation; HClO4, H2KPO4, Na2HPO4, Na2B2O7, NaOH, t-BuOH;

2',3',4',5',6'-pentafluoroacetophenone (652-29-9) + C12H9N2 (66-71-7) → 1,10-Phenanthroline (66-71-7) + 2,3,4,5,6-Pentafluoroacetophenone radical anion

Conditions	Yield
In water Rate constant; Equilibrium constant; Irradiation; HClO4, H2KPO4, Na2HPO4, Na2B2O7, NaOH, t-BuOH;

n-propyltrimethyltin (3531-45-1) + Fe(phenanthroline)3(PF6)3 → 1,10-Phenanthroline (66-71-7) + propene (187737-37-7) + n-propylacetamide (5331-48-6) + 4-propyl-[1,10]phenanthroline (80186-77-2)

Conditions	Yield
With sodium hydroxide 1.) acetonitrile, 22 deg C; Yield given. Multistep reaction. Yields of byproduct given;

n-propyltrimethyltin (3531-45-1) + Os(phenanthroline)3(PF6)3 → 1,10-Phenanthroline (66-71-7) + propene (187737-37-7) + n-propylacetamide (5331-48-6) + 4-propyl-[1,10]phenanthroline (80186-77-2)

Conditions	Yield
With sodium hydroxide 1.) acetonitrile, 25 deg C; Yield given. Multistep reaction. Yields of byproduct given;

n-propyltrimethyltin (3531-45-1) + Ru(phenanthroline)3(PF6)3 → 1,10-Phenanthroline (66-71-7) + propene (187737-37-7) + n-propylacetamide (5331-48-6) + 4-propyl-[1,10]phenanthroline (80186-77-2)

Conditions	Yield
With sodium hydroxide 1.) acetonitrile, 25 deg C; Yield given. Multistep reaction. Yields of byproduct given;

tetramethylstannane (594-27-4) + Fe(phenanthroline)3(PF6)3 → 1,10-Phenanthroline (66-71-7) + 4-methyl-1,10-phenanthroline (31301-28-7) + (CH3)3Sn(NH3)2PF6

Conditions	Yield
With sodium hydroxide 1.) acetonitrile, 70 deg C, 2 h; Yield given. Multistep reaction;

Ethyltrimethylstannan (3531-44-0) + Fe(phenanthroline)3(PF6)3 → 4-ethyl-[1,10]phenanthroline (80206-19-5) + 1,10-Phenanthroline (66-71-7) + 4-methyl-1,10-phenanthroline (31301-28-7) + N-ethylacetamide (625-50-3) + Me3Sn(NH3)2PF6

Conditions	Yield
With sodium hydroxide 1.) acetonitrile, 22 deg C; Yield given. Multistep reaction. Yields of byproduct given;

Ethyltrimethylstannan (3531-44-0) + acetonitrile (75-05-8) → 4-ethyl-[1,10]phenanthroline (80206-19-5) + 1,10-Phenanthroline (66-71-7) + 4-methyl-1,10-phenanthroline (31301-28-7) + N-ethylacetamide (625-50-3) + Me3Sn(NH3)2PF6

Conditions	Yield
With sodium hydroxide 1.) 22 deg C; Yield given. Multistep reaction. Yields of byproduct given;

Isopropyl-trimethyl-stannane (3531-46-2) + Fe(phenanthroline)3(PF6)3 → 1,10-Phenanthroline (66-71-7) + propene (187737-37-7) + N-isopropylacetamide (1118-69-0) + 4-isopropyl-1,10-phenanthroline (80186-78-3)

Conditions	Yield
With sodium hydroxide 1.) acetonitrile, 22 deg C; Yield given. Multistep reaction. Yields of byproduct given;

methyltrioxorhenium and 1,10-phenanthroline 1:1 complex + [2,2]bipyridinyl (366-18-7) → methyltrioxorhenium and 2,2'-bipyridine 1:1 complex + 1,10-Phenanthroline (66-71-7)

Conditions	Yield
at 21.85℃; Equilibrium constant;

2-Aminonicotinaldehyde (7521-41-7) + methanolic KOH → 1,10-Phenanthroline (66-71-7)

Conditions	Yield
In ethanol; dichloromethane

1,10-Phenanthroline (66-71-7) → 5-Nitro-1,10-phenanthroline (4199-88-6)

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 (66-71-7) → 1,10-phenanthroline-5,6-dione (27318-90-7)

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 (66-71-7) + 1,3-dibromo-propane (109-64-8) → 6,7-dihydro-5H-[1,4]diazepino[1,2,3,4-l,m,n][1,10]phenanthroline-4,8-diium dibromide (15302-99-5)

Conditions	Yield
In chlorobenzene at 70 - 120℃;	100%
In nitrobenzene at 120℃;	100%
for 12h; Reflux;	99%

1,10-Phenanthroline (66-71-7) + (bicyclo[2.2.1]hepta-2,5-diene)tetracarbonylmolybdenum(0) (12146-37-1, 124717-04-0) → (1,10-phenanthroline)molybdenum tetracarbonyl (15740-78-0) + bicyclo[2.2.1]hepta-2,5-diene (121-46-0)

Conditions	Yield
In tetrahydrofuran reaction in a calorimeter under argon;	A 100% B n/a

hydrogenchloride (7647-01-0) + 1,10-Phenanthroline (66-71-7) + potassium perrhenate (10466-65-6) → dipotassium oxopentachlororhenate(5+) + o-phenanthrolinium oxopentachlororhenate(V) (17428-51-2)

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 (66-71-7) + potassium perrhenate (10466-65-6) → o-phenanthrolinium oxopentachlororhenate(V) (17428-51-2)

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%

chloro-trimethyl-silane (75-77-4) + 1,10-Phenanthroline (66-71-7) + molybdenium(II) acetate dimer → Mo2Cl4(C12H8N2)2 (178552-10-8)

Conditions	Yield
In tetrahydrofuran (Ar); stirring (5 h); washing (hexane), drying (vac.); elem. anal.;	100%

1,10-Phenanthroline (66-71-7) + [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2 (52462-29-0) → chloro(p-cymene)(η2-1,10-phenanthroline-κ2N)ruthenium (861392-78-1)

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 (66-71-7) + 8Cu(1+)*8((CH3)2CH)3C6H2S(1-)=[CuS((CH3)2CH)3C6H2]8 → [CuS((CH3)2CH)3C6H2]2(C12H8N2)2

Conditions	Yield
In toluene Ar atm.; stirring; concn., addn. of hexane, crystn. (-30°C, overnight), filtn., drying (vac., 40°C);	100%

1,10-Phenanthroline (66-71-7) + tetrakis(actonitrile)copper(I) hexafluorophosphate (64443-05-6) + 2,9-bis(2,6-dimethoxyphenyl)-3-ethynyl-[1,10]-phenanthroline (124318-69-0) → Cu(C12H6N2(C6H3(OCH3)2)2)(C12H8N2)(1+)*PF6(1-)=CuC40H32N4O4PF6 (1196061-73-0)

Conditions	Yield
In [D3]acetonitrile	100%

1,10-Phenanthroline (66-71-7) + niobium pentafluoride (7783-68-8) + trimethylsilylazide (4648-54-8) → [Nb(N3)4(1,10-phen)2][Nb(N3)6] (1628265-33-7)

Conditions	Yield
In acetonitrile at -196 - 20℃; for 6h;	100%

1,10-Phenanthroline (66-71-7) + tantalum pentafluoride (7783-71-3) + trimethylsilylazide (4648-54-8) → [Ta(N3)4(1,10-phen)2][Ta(N3)6] (1628265-35-9)

Conditions	Yield
In acetonitrile at -196 - 20℃; for 6h;	100%

1,10-Phenanthroline (66-71-7) + tetrakis(actonitrile)copper(I) hexafluorophosphate (64443-05-6) + C186H146N14Zn*1.5CH2Cl2 → C210H162Cu2N18Zn(2+)*2F6P(1-)

Conditions	Yield
In dichloromethane-d2	100%

1,10-Phenanthroline (66-71-7) + 2-(6-(2,4,6-trimethylphenyl)pyridin-2-yl)-9-(2,4,6-trimethylphenyl)[1,10]phenanthroline (1613741-33-5) + zinc trifluoromethanesulfonate (54010-75-2) → Zn(2+)*2CF3O3S(1-)*C35H31N3*C12H8N2

Conditions	Yield
In dichloromethane-d2; [D3]acetonitrile	100%

1,10-Phenanthroline (66-71-7) + copper(II) perchlorate hexahydrate + 2-(6-(2,4,6-trimethylphenyl)pyridin-2-yl)-9-(2,4,6-trimethylphenyl)[1,10]phenanthroline (1613741-33-5) → C47H39CuN5(2+)*2ClO4(1-)

Conditions	Yield
In dichloromethane-d2; [D3]acetonitrile	100%

bromobenzene (108-86-1) + 1,10-Phenanthroline (66-71-7) → 6,7-dihydro-5H-[1,4]diazepino[1,2,3,4-lmn][1,10]phenanthroline-4,8-diium (15302-81-5)

Conditions	Yield
at 115℃; for 4h;	100%

1,10-Phenanthroline (66-71-7) + bromotris(pentafluoroethyl)stannane → bromotris(pentafluoroethyl)-1,10-phenanthrolinetin(IV)

Conditions	Yield
In dichloromethane at 20℃; for 30h; Inert atmosphere; Schlenk technique;	100%

1,10-Phenanthroline (66-71-7) + dibromobis(pentafluoroethyl)stannane → dibromobis(pentafluoroethyl)-1,10-phenanthrolinetin(IV)

Conditions	Yield
In dichloromethane for 30h; Inert atmosphere; Schlenk technique;	100%

1,10-Phenanthroline (66-71-7) + iodotris(pentafluoroethyl)stannane → C16H8F15IN2Sn

Conditions	Yield
In dichloromethane at 20℃; for 1h;	100%

1,10-Phenanthroline (66-71-7) + 1,1,1,3,3,3-hexafluoro-2-phenylisopropyl alcohol (718-64-9) + C30H37N3W (1197008-50-6) → (2-trifluoromethyl-2-phenyl-1,1,1-trifluoroethoxy)-2,6-dimethylphenylimide tungsten (VI) (2,5-dimethylpyrrolide)(neophylidene)(1,10-phenanthroline)

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 (66-71-7) + copper(ll) sulfate pentahydrate + bis(triethylammonium)-decahydro-closo-decaborate → [Cu(phen)2][B10H10]

Conditions	Yield
In water; N,N-dimethyl-formamide for 0.0833333h;	100%

1,10-Phenanthroline (66-71-7) + trimethylsilylazide (4648-54-8) + titanium(IV) fluoride (7783-63-3) → C12H8N14Ti

Conditions	Yield
In acetonitrile at -196 - 20℃; for 16h;	100%

1,10-Phenanthroline (66-71-7) + tris(p-trifluoromethylphenyl)phosphine gold bis(trifluoromethanesulfonyl)imidate (888020-56-2) → C33H20AuF9N2P(1+)*C2F6NO4S2(1-)

Conditions	Yield
In dichloromethane Inert atmosphere;	100%

1,10-Phenanthroline (66-71-7) + tris(4-methoxyphenyl)phosphine gold bis(trifluoromethanesulfonyl)imidate → C33H29AuN2O3P(1+)*C2F6NO4S2(1-)

Conditions	Yield
In dichloromethane Inert atmosphere;	100%

1,10-Phenanthroline (66-71-7) + [(C6F5)3PAuNTf2] (890410-20-5) → (Phen)(C6F5)3PAu(I)NTf2

Conditions	Yield
In dichloromethane Inert atmosphere;	100%

1,10-Phenanthroline (66-71-7) + [(Cy3P)Au]N(trifluoromethylsulfonyl)2 (1160111-28-3) → C30H41AuN2P(1+)*C2F6NO4S2(1-)

Conditions	Yield
In dichloromethane Inert atmosphere;	100%

1,10-Phenanthroline (66-71-7) + (p-tolyl)3PAuN(trifluoromethanesulfonyl)2 (1644306-41-1) → C33H29AuN2P(1+)*C2F6NO4S2(1-)

Conditions	Yield
In dichloromethane Inert atmosphere;	100%

1,10-Phenanthroline (66-71-7) + Au(PMe3)NTf2 (1160111-27-2) → C15H17AuN2P(1+)*C2F6NO4S2(1-)

Conditions	Yield
In dichloromethane Inert atmosphere;	100%

1,10-Phenanthroline (66-71-7) + [bis(trifluoromethanesulfonyl)imidate](triphenylphosphine)gold(I) (866395-16-6, 1246810-76-3) → (Phen)Ph3PAuINTf2

Conditions	Yield
In dichloromethane Inert atmosphere;	100%

1,10-Phenanthroline (66-71-7) + 12C17H16N6O2*4Fe(2+)*8CF3O3S(1-) → tris(1,10-phenanthroline)iron(II) triflate (85152-70-1) + 1-([2,2'-bipyridine]-5-ylmethyl)-3-(4-methyl-6-oxo-1,6-dihydropyrimidin-2-yl)urea

Conditions	Yield
In [D3]acetonitrile	A 100% B n/a

Upstream product

• 578-66-5 8-amino quinoline 
• 23647-26-9 1-methyl-1,10-phenanthrolinium iodide 
• 3531-45-1 n-propyltrimethyltin 
• 75-05-8 acetonitrile 
• 3531-46-2 Isopropyl-trimethyl-stannane 
• 3531-44-0 Ethyltrimethylstannan 
• 366-18-7 [2,2]bipyridinyl 
• 7521-41-7 2-Aminonicotinaldehyde 
• 77358-23-7 C₆H₂O₂(SO₃)2^(4-)*H⁽¹⁺⁾ = C₆H₂O₂H(SO₃)2^(3-) 
• 41587-82-0 tris(1,10-phenanthroline)chromium(III) 

Downstream Products

• 100125-12-0 3,8-dibromo-1,10-phenathroline 
• 784209-18-3 2-(4-Bromo-phenyl)-1,2-dihydro-[1,10]phenanthroline 
• 653-37-2 perfluorobenzaldehyde 
• 652-29-9 2',3',4',5',6'-pentafluoroacetophenone 
• 50890-67-0 4,5-Diazafluoren-9-one 
• 4199-88-6 5-Nitro-1,10-phenanthroline 
• 27318-90-7 1,10-phenanthroline-5,6-dione 
• 149054-39-7 2-(4'-bromophenyl)-1,10-phenanthroline 
• 780757-47-3 2,9-di-m-tolyl-[1,10]phenanthroline 
• 252053-94-4 2-[(1-hydroxycyclohexyl)]-1,10-phenanthroline 
• 66127-00-2 3,5,6,8-tetrabromo-1,10-phenanthroline 

Relevant articles and documents

Novel 1,3-diethyl-2-thiobarbiturates of 2,2′-bipyridine and 1,10-phenanthroline: Synthesis, crystal structure and thermal stability

Co-crystallization of 1,3-diethyl-2-thiobarbituric acid (HDetba) with 2,2′-bipyridine (Bipy) and 1,10-phenanthroline (Phen) results in preparing a salt co-crystal, BipyH(Detba)(HDetba) (1), and the salt, PhenH(Detba)·H2O (2). The compounds are characterized by single–crystal and powder X–ray diffraction and TG-DSC. The nitrogen atoms of BipyH+ adopt a cis conformation and the N–C–C–N torsion angle is ?17.3(1)o. There are six intermolecular hydrogen bonds O–H?O, N–H?O, C–H?O and C–H?S in (1) which form a 2D plane network. One Detba– ion and one HDetba molecule form a pair by means of O–H?O hydrogen bonds. Detba? anions in (2) do not form dimers, they are connected by N–H?O, C–H?S, and C–H?O hydrogen bonds only with PhenH+ cations and water molecules which form a 3D net. Different π?π interactions between the rings are found in (1)?(2).

Deep eutectic solvents used as catalysts for synthesis of 1,10-phenanthroline by improved Skraup reaction

Abstract: In this study, three different choline chloride-based deep eutectic solvents were synthesized. And it is the first time to synthesize 1,10-phenanthroline through an improved Skraup reaction using deep eutectic solvent as the new catalyst from acrolein and 8-aminoquinoline. The deep eutectic solvents were characterized by Fourier transform infrared (FT-IR), 1H nuclear magnetic resonance (1H NMR), pH/mV meter, and thermogravimetric analysis (TGA). The research results show that the deep eutectic solvent formed by sulfanilic acid and choline chloride has the strongest acidity and highest catalytic active among the three deep eutectic solvents. Besides, the impacts of reaction parameters and molar ratio of raw materials on the reaction were also investigated. Under the optimized reaction conditions, the maximum selectivity and yield of 1,10-phenanthroline were achieved as 84.6 and 75.6%, respectively. The synthesis method, meanwhile, also has simple preparation process and low cheaper catalyst raw. Graphical abstract: [InlineMediaObject not available: see fulltext.] Replacing traditional sulfuric acid and hydrochloric acid with deep eutectic solvents (DESs) as new catalysts provides a more efficient, greener and more economical strategy for the synthesis of 1,10-phenanthroline by a new improved Skraup reaction.

Palladium-(II) and -(IV) complexes as intermediates in catalytic C-C bond-forming reactions

Palladium-(II) and -(IV) species active as catalysts in C-C bond-forming reactions have been stabilized by adding phenanthroline as a ligand.The complexes formed have been characterized by chemical and spectroscopic methods and their formation and subsequent fate have been monitored by 1H NMR spectroscopy.

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INCLUSION COMPOUNDS OF ORGANIC AZOCHROMOPHORES IN THE CAVITIES OF METAL-ORGANIC FRAMEWORKS (Cr,?Al)– MIL-101: SYNTHESIS AND PHOTOCHEMICAL STUDIES

Abstract: Inclusion compounds of nitrogen-containing aromatic chromophores 4,4′-bispyridylethylene (bpe) and 4,4′-azopyridine (apy) in the cavities of mesoporous metal-organic frameworks Cr–MIL-101 and Al–MIL-101 are prepared and characterized by elemental analysis and nitrogen adsorption methods with a goal of finding approaches to the design of solid photochromic materials combining the benefits of photochromes in liquid solutions (high quantum yields) and in solid states (increased resistance to photodegradation). Photochemical properties of these compounds are qualitatively studied. Compound apy@Al–MIL-101 exhibits higher photoactivity than polycrystalline apy. Three other inclusion compounds are not photoactive. Possible reasons of the lack of photoactivity in these compounds are discussed. [Figure not available: see fulltext.]

Iron(II)-Catalyzed Aerobic Biomimetic Oxidation of N-Heterocycles

Herein, an iron(II)-catalyzed biomimetic oxidation of N-heterocycles under aerobic conditions is described. The dehydrogenation process, involving several electron-transfer steps, is inspired by oxidations occurring in the respiratory chain. An environmentally friendly and inexpensive iron catalyst together with a hydroquinone/cobalt Schiff base hybrid catalyst as electron-transfer mediator were used for the substrate-selective dehydrogenation reaction of various N-heterocycles. The method shows a broad substrate scope and delivers important heterocycles in good-to-excellent yields.