o-Phenanthroline | 1,10-Phenanthroline | MMP

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o-Phenanthroline (1,10-Phenanthroline), a metal chelator, prevents the induction of chromosomal aberrations in streptozotocin-treated cells. o-Phenanthroline (1,10-Phenanthroline) forms a red chelate with Fe2+ that absorbs maximally at 510 nm.

Synonyms: 1,10-Phenanthroline

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Quality Control of o-Phenanthroline Purity: 98% SDS Specification

COA

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Product Details of o-Phenanthroline

CAS No. :	66-71-7
Formula :	C₁₂H₈N₂
M.W :	180.21
SMILES Code :	C1=CC3=C(C2=NC=CC=C12)N=CC=C3
Synonyms :	1,10-Phenanthroline
MDL No. :	MFCD00011678
InChI Key :	DGEZNRSVGBDHLK-UHFFFAOYSA-N
Pubchem ID :	1318

Safety of o-Phenanthroline

GHS Pictogram:
Signal Word:	Danger
Hazard Statements:	H301-H410
Precautionary Statements:	P264-P270-P273-P301+P310+P330-P391-P405-P501
Class:	6.1
UN#:	2811
Packing Group:	Ⅲ

Application In Synthesis of o-Phenanthroline

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 66-71-7 ]
Downstream synthetic route of [ 66-71-7 ]

[ 66-71-7 ] Synthesis Path-Upstream 1~1

1
[ 66-71-7 ]
[ 5743-04-4 ]
[ 1245-13-2 ]

References: [1] Zeitschrift fur Anorganische und Allgemeine Chemie, 2013, vol. 639, # 3-4, p. 558 - 562.

[ 66-71-7 ] Synthesis Path-Downstream 1~35

1
[ 3531-46-2 ]
[ 75-05-8 ]
[ 66-71-7 ]
[ 187737-37-7 ]
[ 1118-69-0 ]
[ 80186-78-3 ]

References: [1]Journal of the American Chemical Society,1982,vol. 104,p. 1319 - 1330.

2
[ 3531-46-2 ]
Fe(phenanthroline)3(PF₆)3 [ No CAS ]
[ 66-71-7 ]
[ 187737-37-7 ]
[ 1118-69-0 ]
[ 80186-78-3 ]

References: [1]Journal of the American Chemical Society,1982,vol. 104,p. 1319 - 1330.

3
[ 66-71-7 ]
[ 40000-20-2 ]

References: [1]Crystal Growth and Design,2016,vol. 16,p. 6992 - 6999.
[2]Inorganic Chemistry,2010,vol. 49,p. 2889 - 2900.
[3]Dalton Transactions,2007,p. 3421 - 3426.
[4]European Journal of Inorganic Chemistry,2017,vol. 2017,p. 3799 - 3810.
[5]Photochemistry and Photobiology,2019,vol. 95,p. 267 - 279.
[6]Chemical Communications,2015,vol. 51,p. 17269 - 17272.
[7]Inorganic Chemistry,2018,vol. 57,p. 14362 - 14373.
[8]Antimicrobial Agents and Chemotherapy,2017,vol. 61.
[9]Chemistry - A European Journal,2019,vol. 25,p. 334 - 342.
[10]Molecules,2011,vol. 16,p. 8353 - 8367.
[11]Synthesis,2013,vol. 45,p. 753 - 758.
[12]Journal of the American Chemical Society,2014,vol. 136,p. 7861 - 7864.
[13]Journal of the American Chemical Society,2014,vol. 136,p. 15300 - 15309.
[14]European Journal of Inorganic Chemistry,2017,vol. 2017,p. 623 - 629.

4
[ 66-71-7 ]
[ 7089-68-1 ]

Yield	Reaction Conditions	Operation in experiment
		2-Chloro-1,10-Phenanthroline, (1) 2-Chloro-1,10-phenanthroline was prepared from 1,10-phenanthroline following the procedure of B. E. Halcrow, Wm. O. Kermack; Journal of the Chemical Society (1946), 155-7 and was isolated in satisfactory yield.

References: [1]Journal of Organic Chemistry,2007,vol. 72,p. 2318 - 2328.
[2]Journal of the Indian Chemical Society,1993,vol. 70,p. 877 - 884.
[3]Patent: US2009/142618,2009,A1 .
[4]Patent: WO2011/30566,2011,A1 .
[5]Patent: WO2012/124310,2012,A1 .
[6]European Journal of Inorganic Chemistry,2013,p. 6137 - 6146.
[7]Journal of Organic Chemistry,2017,vol. 82,p. 4203 - 4215.
[8]Chemistry - A European Journal,2017,vol. 23,p. 6499 - 6503.
[9]Molecules,2019,vol. 24.
[10]Patent: CN109776532,2019,A .
[11]ACS Catalysis,2019,p. 5336 - 5344.

5
[ 52522-40-4 ]
[ 66-71-7 ]
[ 81191-65-3 ]

References: [1]Synthesis and Reactivity in Inorganic and Metal-Organic Chemistry,1981,vol. 11,p. 517 - 524.

6
[ 66-71-7 ]
[ 940-07-8 ]
copper(II) acetate dihydrate [ No CAS ]
[ 7732-18-5 ]
[ 937021-44-8 ]

References: [1]Inorganica Chimica Acta,2007,vol. 360,p. 2029 - 2038.

7
[ 66-71-7 ]
[ 940-07-8 ]
[ 5970-45-6 ]
[ 935730-72-6 ]

References: [1]Journal of Molecular Structure,2007,vol. 832,p. 48 - 54.

8
[ 66-71-7 ]
[ 5743-04-4 ]
[ 130-85-8 ]
[ 1221273-08-0 ]

References: [1]Zeitschrift fur Anorganische und Allgemeine Chemie,2009,vol. 635,p. 1664 - 1668.

9
oxovanadium(IV) sulfate [ No CAS ]
[ 66-71-7 ]
[ 1119-34-2 ]
[ 90-02-8 ]
[VO(N-salicylidene-L-arginine(-1H))(1,10-phenanthroline)]Cl [ No CAS ]

References: [1]Dalton Transactions,2010,vol. 39,p. 7104 - 7113.

10
[ 67-56-1 ]
[ 66-71-7 ]
[ 2645-22-9 ]
cadmium(II) perchlorate hexahydrate [ No CAS ]
[cadmium(1,10-phenanthroline)(μ-4,4'-dithiodipyridine)(4,4'-dithiodipyridine)(H2O)](perchlorate)2*2MeOH*1.5H2O [ No CAS ]

References: [1]Zeitschrift fur Anorganische und Allgemeine Chemie,2011,vol. 637,p. 94 - 101.

11
[ 66-71-7 ]
[ 16490-02-1 ]
manganese(II) chloride dihydrate [ No CAS ]
sodium perchlorate [ No CAS ]
[ 7732-18-5 ]
Mn4(μ-pyrimidine-4,6-dicarboxylate)3(H2O)4(1,10-phenanthroline)(ClO4)2*11H2O [ No CAS ]

References: [1]European Journal of Inorganic Chemistry,2011,p. 68 - 77.

12
[ 66-71-7 ]
[ 16490-02-1 ]
manganese(II) chloride dihydrate [ No CAS ]
[ 7732-18-5 ]
potassium nitrate [ No CAS ]
Mn4(μ-pyrimidine-4,6-dicarboxylate)3(H2O)4(1,10-phenanthroline)(NO3)2*11H2O [ No CAS ]

References: [1]European Journal of Inorganic Chemistry,2011,p. 68 - 77.

13
[ 66-71-7 ]
[ 42906-19-4 ]

References: [1]Patent: US2013/1521,2013,A1 .

14
[ 66-71-7 ]
iron(II) chloride tetrahydrate [ No CAS ]
[ 499-49-0 ]
[ 7732-18-5 ]
[Fe(1,10-phenanthroline)3]*(5-methylisophthalic acid(-1.5H))*(5-methylisophthalic acid(-0.5H))*(5-methylisophthalic acid)*4.5H₂O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
61%	With sodium hydroxide; at 120℃; for 72h;Autoclave;	General procedure: Under vigorous magnetic stirring, <strong>[499-49-0]5-methylisophthalic acid</strong> (H2mip, 0.090 g, 0.50 mmol) was suspended in 10 ml water, an accurate amount of 1.0 mmol (if not mentioned specially) NaOH was slowly added, and then the (hydrated) chloride salt of manganese, iron, cobalt, nickel, copper or zinc was added. Finally, 2,2?-bipyridine (bpy, 0.078 g, 0.50 mmol) or 1,10-phenanthroline (phen, 0.100 g, 0.50 mmol) was added. The mixture was transferred into a 20 ml Teflon-lined vessel, heated to 120?200 °C at the rate of 5 °C/h, and kept at that temperature for 3 days, then slowly cooled down to room temperature at the rate of 5 °C/h. Crystals were obtained by filtration, washed with water and dried in air. The purity of products was verified by powder X-ray diffraction measurement.

References: [1]Polyhedron,2013,vol. 50,p. 219 - 228.

15
[ 66-71-7 ]
cobalt(II) chloride hexahydrate [ No CAS ]
[ 499-49-0 ]
[ 7732-18-5 ]
[ 1422466-55-4 ]

Yield	Reaction Conditions	Operation in experiment
28%	With sodium hydroxide; at 180℃; for 72h;Autoclave;	General procedure: Under vigorous magnetic stirring, <strong>[499-49-0]5-methylisophthalic acid</strong> (H2mip, 0.090 g, 0.50 mmol) was suspended in 10 ml water, an accurate amount of 1.0 mmol (if not mentioned specially) NaOH was slowly added, and then the (hydrated) chloride salt of manganese, iron, cobalt, nickel, copper or zinc was added. Finally, 2,2?-bipyridine (bpy, 0.078 g, 0.50 mmol) or 1,10-phenanthroline (phen, 0.100 g, 0.50 mmol) was added. The mixture was transferred into a 20 ml Teflon-lined vessel, heated to 120?200 °C at the rate of 5 °C/h, and kept at that temperature for 3 days, then slowly cooled down to room temperature at the rate of 5 °C/h. Crystals were obtained by filtration, washed with water and dried in air. The purity of products was verified by powder X-ray diffraction measurement.

References: [1]Polyhedron,2013,vol. 50,p. 219 - 228.

16
[ 66-71-7 ]
nickel(II) chloride hexahydrate [ No CAS ]
[ 499-49-0 ]
[ 7732-18-5 ]
[Ni₃(5-methylisophthalic acid(-2H))3(1,10-phenanthroline)2]*3.8H₂O}n [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
37%	With sodium hydroxide; at 200℃; for 72h;Autoclave;	General procedure: Under vigorous magnetic stirring, <strong>[499-49-0]5-methylisophthalic acid</strong> (H2mip, 0.090 g, 0.50 mmol) was suspended in 10 ml water, an accurate amount of 1.0 mmol (if not mentioned specially) NaOH was slowly added, and then the (hydrated) chloride salt of manganese, iron, cobalt, nickel, copper or zinc was added. Finally, 2,2?-bipyridine (bpy, 0.078 g, 0.50 mmol) or 1,10-phenanthroline (phen, 0.100 g, 0.50 mmol) was added. The mixture was transferred into a 20 ml Teflon-lined vessel, heated to 120?200 °C at the rate of 5 °C/h, and kept at that temperature for 3 days, then slowly cooled down to room temperature at the rate of 5 °C/h. Crystals were obtained by filtration, washed with water and dried in air. The purity of products was verified by powder X-ray diffraction measurement.

References: [1]Polyhedron,2013,vol. 50,p. 219 - 228.

17
[ 66-71-7 ]
copper(II) choride dihydrate [ No CAS ]
[ 499-49-0 ]
[Cu₃(5-methylisophthalic acid(-1H))2(5-methylisophthalic acid(-2H))2(1,10-phenanthroline)2]n [ No CAS ]
[Cu(5-methylisophthalic acid(-1H))2(1,10-phenanthroline)] [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
12%	With sodium hydroxide; In water; at 150℃; for 72h;Autoclave;	General procedure: Under vigorous magnetic stirring, <strong>[499-49-0]5-methylisophthalic acid</strong> (H2mip, 0.090 g, 0.50 mmol) was suspended in 10 ml water, an accurate amount of 1.0 mmol (if not mentioned specially) NaOH was slowly added, and then the (hydrated) chloride salt of manganese, iron, cobalt, nickel, copper or zinc was added. Finally, 2,2?-bipyridine (bpy, 0.078 g, 0.50 mmol) or 1,10-phenanthroline (phen, 0.100 g, 0.50 mmol) was added. The mixture was transferred into a 20 ml Teflon-lined vessel, heated to 120?200 °C at the rate of 5 °C/h, and kept at that temperature for 3 days, then slowly cooled down to room temperature at the rate of 5 °C/h. Crystals were obtained by filtration, washed with water and dried in air. The purity of products was verified by powder X-ray diffraction measurement.

References: [1]Polyhedron,2013,vol. 50,p. 219 - 228.

18
[ 66-71-7 ]
[ 499-49-0 ]
[ 7646-85-7 ]
[Zn₄(5-methylisophthalic acid(-2H))4(1,10-phenanthroline)4]n [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
81%	With sodium hydroxide; In water; at 200℃; for 72h;Autoclave;	General procedure: Under vigorous magnetic stirring, <strong>[499-49-0]5-methylisophthalic acid</strong> (H2mip, 0.090 g, 0.50 mmol) was suspended in 10 ml water, an accurate amount of 1.0 mmol (if not mentioned specially) NaOH was slowly added, and then the (hydrated) chloride salt of manganese, iron, cobalt, nickel, copper or zinc was added. Finally, 2,2?-bipyridine (bpy, 0.078 g, 0.50 mmol) or 1,10-phenanthroline (phen, 0.100 g, 0.50 mmol) was added. The mixture was transferred into a 20 ml Teflon-lined vessel, heated to 120?200 °C at the rate of 5 °C/h, and kept at that temperature for 3 days, then slowly cooled down to room temperature at the rate of 5 °C/h. Crystals were obtained by filtration, washed with water and dried in air. The purity of products was verified by powder X-ray diffraction measurement.

References: [1]Polyhedron,2013,vol. 50,p. 219 - 228.

19
[ 66-71-7 ]
europium(III) chloride hexahydrate [ No CAS ]
[ 39207-65-3 ]
Eu(iButCHex)₃*1,10-phenanthroline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; In ethanol; water;	General procedure: In the preparation of the Ln(CA)3·Phn and Ln(CA)3·Bpy adducts the 3-N NaOH water solution and an ethanol solution of Phn or Bpy were added to an ethanol solution of CA. Then, a water?ethanol (1:1) solution of LnCl3·6H2O was drop by drop added to the previous mixture at heating in a water bath (at 60?70°C) or sometimes without heating. A molar ratio of the reagents CA: Phn (Bpy): lanthanide chloride: NaOH was equal to 3:1:1:3. The compound Eu(AcCHex)3·Phen was also synthesized by other method involving the preparation of an ethanol solution of a mixture of CA, Phen and EuCl3·6H2O in a molar ratio of 3:1:1 and adjusting the pH value of reaction mixture to 6 with a liquid ammonia. It should be pointed out that the heating of the reaction mixture results in a decrease in the keto/enol ratio of cycloalkanone [37] that promotes a binding of CA with the Ln3+ ion. At the same time, the probability of decomposition of cycloalkanonate anion increases.

References: [1]Journal of Photochemistry and Photobiology A: Chemistry,2016,vol. 314,p. 14 - 21.

20
[ 66-71-7 ]
terbium(III) chloride hexahydrate [ No CAS ]
[ 39207-65-3 ]
Tb(iButCHex)₃*1,10-phenanthroline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; In ethanol; water;	General procedure: In the preparation of the Ln(CA)3·Phn and Ln(CA)3·Bpy adducts the 3-N NaOH water solution and an ethanol solution of Phn or Bpy were added to an ethanol solution of CA. Then, a water?ethanol (1:1) solution of LnCl3·6H2O was drop by drop added to the previous mixture at heating in a water bath (at 60?70°C) or sometimes without heating. A molar ratio of the reagents CA: Phn (Bpy): lanthanide chloride: NaOH was equal to 3:1:1:3. The compound Eu(AcCHex)3·Phen was also synthesized by other method involving the preparation of an ethanol solution of a mixture of CA, Phen and EuCl3·6H2O in a molar ratio of 3:1:1 and adjusting the pH value of reaction mixture to 6 with a liquid ammonia. It should be pointed out that the heating of the reaction mixture results in a decrease in the keto/enol ratio of cycloalkanone [37] that promotes a binding of CA with the Ln3+ ion. At the same time, the probability of decomposition of cycloalkanonate anion increases.

References: [1]Journal of Photochemistry and Photobiology A: Chemistry,2016,vol. 314,p. 14 - 21.

21
[ 66-71-7 ]
gadolinium(III) chloride hexahydrate [ No CAS ]
[ 39207-65-3 ]
Gd(iButCHex)₃*1,10-phenanthroline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; In ethanol; water;	General procedure: In the preparation of the Ln(CA)3·Phn and Ln(CA)3·Bpy adducts the 3-N NaOH water solution and an ethanol solution of Phn or Bpy were added to an ethanol solution of CA. Then, a water?ethanol (1:1) solution of LnCl3·6H2O was drop by drop added to the previous mixture at heating in a water bath (at 60?70°C) or sometimes without heating. A molar ratio of the reagents CA: Phn (Bpy): lanthanide chloride: NaOH was equal to 3:1:1:3. The compound Eu(AcCHex)3·Phen was also synthesized by other method involving the preparation of an ethanol solution of a mixture of CA, Phen and EuCl3·6H2O in a molar ratio of 3:1:1 and adjusting the pH value of reaction mixture to 6 with a liquid ammonia. It should be pointed out that the heating of the reaction mixture results in a decrease in the keto/enol ratio of cycloalkanone [37] that promotes a binding of CA with the Ln3+ ion. At the same time, the probability of decomposition of cycloalkanonate anion increases.

References: [1]Journal of Photochemistry and Photobiology A: Chemistry,2016,vol. 314,p. 14 - 21.

22
[ 66-71-7 ]
manganese(II) chloride tetrahydrate [ No CAS ]
[ 23351-91-9 ]
Mn(1,10-phenanthroline)(5-bromoisophthalic acid) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	In water; at 160℃; for 72h;Autoclave;	A mixture of MnCl24H2O (0.0594 g, 0.3 mmol), 5-Br-H2ipa (0.0735 g, 0.3 mmol) and 1,10-phen (0.1189 g,0.6 mmol) was sealed in a 25 mL Teflon-lined stainless steel Parr bomb containing deionized H2O (20 mL), heated at 160 °C for 72 h, and then cooled down to room temperature. Small yellow rod-like crystals of complex 1 (yield 90 percent based on MnCl24H2O) were isolated and washed with deionized water and ethanol. Anal. Calcd. for 1, C20H11BrMnN2O4:C, 50.2; N, 5.9; H, 2.3. Found: C, 50.3; N, 5.9; H,2.4 percent. IR (KBr)/cm-1: 3417m, 3089m, 1619s, 1567m, 1530m, 1518m, 1451m, 1426s, 1344m, 1145w, 1102w, 920m, 865m, 852m, 790m, 730m, 639m, 537w, 421w.

References: [1]Transition Metal Chemistry,2016,vol. 41,p. 375 - 385.

23
[ 66-71-7 ]
dysprosium(III) nitrate hexahydrate [ No CAS ]
[ 720-94-5 ]
Dy(1,10-phenanthroline)(4,4,4-trifluoro-1-(4-methylphenyl)-1,3-butanedione)<SUB>3</SUB> [ No CAS ]

References: [1]Inorganic Chemistry,2016,vol. 55,p. 3865 - 3871.

24
[ 66-71-7 ]
[ 422-64-0 ]
[ 35342-67-7 ]
[(1,10-phenanthroline)₂Cu][O₂CC₂F₅] [ No CAS ]

References: [1]Dalton Transactions,2016,vol. 45,p. 8468 - 8474.

25
[ 10016-52-1 ]
[ 66-71-7 ]
C₃₆H₂₀N₄O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Under an argon gas atmosphere, 1,4-dibromobenzene (50 g, 211 mmol) was dissolved in diethylether (350 mL). The obtained solution was cooled down to 0°C., into which n-butyllithium (2.69M hexane solution) (72 mL, 194 mmol) was dropped for 30 minutes and was stirred for another 30 minutes. The prepared p-bromophenyllithium was dropped into a suspension of diethylether (350 mL) of 1,10-phenanthroline (15 g, 85 mmol) (compound 1) at 0°C. for 45 minutes and was further stirred for five hours. After the completion of the reaction, water was dropped into the reaction solution at 0 degree C. for 30 minutes. The reaction solution was extracted by dichloromethane. A solvent was distilled off under reduced pressure while leaving 200 mL of dichloromethane Manganese dioxide (150 g) was added to the obtained solution and stirred for 4.5 hours at the room temperature. Subsequently, the solution was added with magnesium sulfate and separated by filtration. The solvent was distilled off under reduced pressure. A residue was refined by silica-gel column chromatography (dichloromethane/hexane/methanol). The obtained solid was washed with methanol and then was dried under reduced pressure to provide the compound 2 (23 g, a yield of 81percent) as a white solid. As a result of FD-MS (Field Desorption Mass Spectrometry) analysis, the reactant was identified as the compound 2. A compound 1D was synthesized according to the above scheme by the same method as in synthesis of the compound 13 except forreplacing the compound 11 with <strong>[10016-52-1]2,8-dibromodibenzofuran</strong>.

References: [1]Patent: KR2015/54797,2015,A .Location in patent: Paragraph 0678; 0704; 0712-0716.

26
[ 66-71-7 ]
[ 5467-57-2 ]
praseodymium(III) chloride hexahydrate [ No CAS ]
[Pr₂(2-chloroquinoline-4-carboxylate)₆(1,10-phenanthroline)₂(H₂O)₂]2H₂O [ No CAS ]