57709-61-2

Basic information

• Product Name: 1,10-PHENANTHROLINE-2,9-DICARBOXYLIC ACID
• Synonyms: 1,10-PHENANTHROLINE-2,9-DICARBOXYLIC ACID;1,10-PHENANTHROLINE-2,9-DICARBOXYLIC ACID HYDRATE, 98%;2,9-dicarboxy-1,10-phenanthroline;2,9-Dicarboxylicacid-1,10-phenanthroline;1,10-PHENTHROLINE-2,9-DICARBOXYLIC ACID
• CAS NO: 57709-61-2
• Molecular Formula: C₁₄H₈N₂O₄
• Molecular Weight: 268.22
• Product Categories: MOFS COFS
• Mol File: 57709-61-2.mol
• Article Data: 20

Chemical Properties

• Melting Point: 239 °C(Solv: methanol (67-56-1))
• Boiling Point: 563.1 °C at 760 mmHg
• Flash Point: 294.3 °C
• Appearance: /
• Density: 1.585 g/cm³
• Vapor Pressure: 1.62E-13mmHg at 25°C
• Storage Temp.: 2-8°C
• PKA: 0.61±0.30(Predicted)
• CAS DataBase Reference: 1,10-PHENANTHROLINE-2,9-DICARBOXYLIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 1,10-PHENANTHROLINE-2,9-DICARBOXYLIC ACID(57709-61-2)
• EPA Substance Registry System: 1,10-PHENANTHROLINE-2,9-DICARBOXYLIC ACID(57709-61-2)

Safety Data

• Statements: 36/38
• Safety Statements: 26
• Hazardous Substances Data: 57709-61-2(Hazardous Substances Data)

Usage

Uses

1,10-Phenanthroline-2,9-dicarboxylic acid hydrate is used to produce 1,10-phenanthroline-2,9-dicarbonyl chloride.

InChI:InChI=1/C14H8N2O4/c17-13(18)9-5-3-7-1-2-8-4-6-10(14(19)20)16-12(8)11(7)15-9/h1-6H,(H,17,18)(H,19,20)/p-2

Synthetic route

2,9-Bis(trichloromethyl)-1,10-phenanthroline (78831-41-1) → 1,10-phenanthroline-2,9-dicarboxylic acid (57709-61-2)

Conditions	Yield
With sulfuric acid In water at 85℃; for 7h;	100%
With sulfuric acid at 80 - 90℃; for 6h;	91%
With nitric acid for 3h; Heating;

1,10-phenanthroline-2,9-dicarboxaldehyde (57709-62-3) → 1,10-phenanthroline-2,9-dicarboxylic acid (57709-61-2)

Conditions	Yield
With nitric acid for 4h; Heating;	96%
With nitric acid for 24h; Reflux;	90%
With nitric acid for 6h; Reflux;	83.15%

2,9-bis(tribromomethyl)-1,10-phenanthroline (78831-40-0) → 1,10-phenanthroline-2,9-dicarboxylic acid (57709-61-2)

Conditions	Yield
With nitric acid for 3h; Heating;

2.9-dimethyl-1,10-phenanthroline (484-11-7) → 1,10-phenanthroline-2,9-dicarboxylic acid (57709-61-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: SeO2 / dioxane / 2 h / Heating 2: 430 mg / aq. HNO3 / 2 h / Heating View Scheme
Multi-step reaction with 2 steps 1: 86 percent / NCS, 3-chloroperbenzoic acid / CCl4 / 12 h / Heating 2: 91 percent / 98percent H2SO4 / 6 h / 80 - 90 °C View Scheme
Multi-step reaction with 2 steps 1: SeO2 / dioxane 2: 96 percent / 60percent nitric acid / 4 h / Heating View Scheme

1,10-phenanthroline-2,9-dicarboxylic acid (57709-61-2) → 1,10‐phenanthroline‐2,9‐dicarbonyl dichloride (84670-37-1)

Conditions	Yield
With thionyl chloride at 120℃; for 1h; Inert atmosphere;	100%
With thionyl chloride for 2h; Heating;	76%
With thionyl chloride In toluene

pentafluorophenyl trifloroacetate (14533-84-7) + 1,10-phenanthroline-2,9-dicarboxylic acid (57709-61-2) → bis(pentafluorophenyl)-1,10-phenanthroline-2,9-dicarboxylate (516462-64-9)

Conditions	Yield
In pyridine; N,N-dimethyl-formamide at 20℃; for 12h;	98%

1,10-phenanthroline-2,9-dicarboxylic acid (57709-61-2) + 4,4',4-tri-tert-butyl-2,2':6',2-terpyridine → C41H41N5O4Ru (1452388-81-6)

Conditions	Yield
With triethylamine In ethanol; water for 2h; Reflux;	97%

3-aminoquinoline (580-17-6) + 1,10-phenanthroline-2,9-dicarboxylic acid (57709-61-2) → N2,N9-di(quinolin-3-yl)-1,10-phenanthroline-2,9-dicarboxamide (929895-49-8)

Conditions	Yield
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 1-hydroxy-7-aza-benzotriazole In N,N-dimethyl-formamide at 20℃; for 1h;	89%
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 48h; Reagent/catalyst; Solvent; Inert atmosphere;	85%

Ru(2,2′;6,2″-terpyridine)Cl3 + 1,10-phenanthroline-2,9-dicarboxylic acid (57709-61-2) → C29H17N5O4Ru (1452388-79-2)

Conditions	Yield
With triethylamine In ethanol; water for 2h; Reflux;	89%

methanol (67-56-1) + 1,10-phenanthroline-2,9-dicarboxylic acid (57709-61-2) → 2,9-dimethyl 1,10-phenanthroline-2,9-dicarboxylate (78831-35-3)

Conditions	Yield
With sulfuric acid Reflux;	86%
With sulfuric acid at 70℃; for 10h;	78%
With hydrogenchloride for 2.5h; Heating;	67%
With hydrogenchloride for 2.5h; Reflux;	65%
With sulfuric acid

2,6-Diaminopyridine (141-86-6) + 1,10-phenanthroline-2,9-dicarboxylic acid (57709-61-2) → N,N'-bis(2-amino-6-pyridyl)-1,10-phenanthroline-2,9-dicarboxamide

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 3h;	85%

4-(trimethylsilyloxy)aniline (36309-42-9) + 1,10-phenanthroline-2,9-dicarboxylic acid (57709-61-2) → N,N'-bis(4-aminophenol)-1,10-phenanthroline-2,9-carboxamide (1266331-36-5)

Conditions	Yield
With 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 2h;	78%

ethanol (64-17-5) + 1,10-phenanthroline-2,9-dicarboxylic acid (57709-61-2) → 1,10-phenanthroline-2,9-dicarboxylic acid diethyl ester (1172621-51-0)

Conditions	Yield
With sulfuric acid for 11h; Reflux;	78%
With sulfuric acid for 12h; Reflux;	73%

1,10-Phenanthroline (66-71-7) + iron(III) chloride hexahydrate + 1,10-phenanthroline-2,9-dicarboxylic acid (57709-61-2) → [FeCl(1,10-phenanthroline)(1,10-phenanthroline-2,9-dicarboxylate)]*H2O

Conditions	Yield
In methanol at 130℃; for 72h; High pressure; Autoclave;	75%

methanol (67-56-1) + iron(II) perchlorate hexahydrate + 1,10-phenanthroline-2,9-dicarboxylic acid (57709-61-2) → [FeII(2,9-bis(carbomethoxy)-1,10-phenanthroline)2](ClO4)2

Conditions	Yield
for 5h; Reflux;	74%

1-iodo-10-undecene (7766-49-6) + 1,10-phenanthroline-2,9-dicarboxylic acid (57709-61-2) → C36H48N2O4

Conditions	Yield
Stage #1: 1,10-phenanthroline-2,9-dicarboxylic acid With tetrabutyl ammonium fluoride In tetrahydrofuran at 20℃; for 3h; Inert atmosphere; Stage #2: 1-iodo-10-undecene In tetrahydrofuran at 20℃; for 48h; Inert atmosphere;	74%

2-(aminoethyl)pyridine (2706-56-1) + 1,10-phenanthroline-2,9-dicarboxylic acid (57709-61-2) → 2,9-bis{[2-(2-pyridyl)ethylamino]carbonyl}-1,10-phenanthroline

Conditions	Yield
Stage #1: 1,10-phenanthroline-2,9-dicarboxylic acid With 1,1'-carbonyldiimidazole In N,N-dimethyl-formamide at 40 - 50℃; Stage #2: 2-(aminoethyl)pyridine In N,N-dimethyl-formamide at 20℃; for 108h;	73%

iron(III) chloride hexahydrate + 1,10-phenanthroline-2,9-dicarboxylic acid (57709-61-2) + acetonitrile (75-05-8) → NH4[Fe(1,10-phenanthroline-2,9-dicarboxylate)2]*2(acetonitrile)

Conditions	Yield
With 1,10-Phenanthroline In water at 130℃; for 72h; High pressure; Autoclave;	73%

methanol (67-56-1) + dysprosium(III) nitrate hexahydrate + 1,10-phenanthroline-2,9-dicarboxylic acid (57709-61-2) → C28H12DyN4O8(1-)*4CH4O

Conditions	Yield
With triethylamine at 120℃; for 48h; pH=8.2; pH-value; Sealed tube;	72%

C24H24Br2O4 + 1,10-phenanthroline-2,9-dicarboxylic acid (57709-61-2) → C38H30N2O8

Conditions	Yield
Stage #1: 1,10-phenanthroline-2,9-dicarboxylic acid With tetrabutyl ammonium fluoride In tetrahydrofuran at 20℃; for 3h; Inert atmosphere; Stage #2: C24H24Br2O4 In tetrahydrofuran at 20℃; for 48h; Inert atmosphere;	66%

methyl 3-methoxy-4-aminobenzoate (41608-64-4) + 1,10-phenanthroline-2,9-dicarboxylic acid (57709-61-2) → C32H26N4O8

Conditions	Yield
Stage #1: 1,10-phenanthroline-2,9-dicarboxylic acid With oxalyl dichloride; triethylamine; N,N-dimethyl-formamide In dichloromethane Stage #2: methyl 3-methoxy-4-aminobenzoate In dichloromethane	65%

histamine (51-45-6) + 1,10-phenanthroline-2,9-dicarboxylic acid (57709-61-2) → 2,9-bis-{[2-(4-imidazolyl)ethylamino]carbonyl}-1,10-phenanthroline

Conditions	Yield
Stage #1: 1,10-phenanthroline-2,9-dicarboxylic acid With 1,1'-carbonyldiimidazole In N,N-dimethyl-formamide Stage #2: histamine In N,N-dimethyl-formamide	63%

2-(1H-benzimidazol-2-yl)ethylamine (29518-68-1) + 1,10-phenanthroline-2,9-dicarboxylic acid (57709-61-2) → 2,9-bis-{[2-(2-benzimidazolyl)ethylamino]carbonyl}-1,10-phenanthroline

Conditions	Yield
Stage #1: 1,10-phenanthroline-2,9-dicarboxylic acid With 1,1'-carbonyldiimidazole In N,N-dimethyl-formamide Stage #2: 2-(1H-benzimidazol-2-yl)ethylamine In N,N-dimethyl-formamide	61%

nickel(II) perchlorate hexahydrate + 1,10-phenanthroline-2,9-dicarboxylic acid (57709-61-2) → [Ni(1,10-phenanthroline-2,9-dicarboxylate)(H2O)3]*H2O (854933-76-9)

Conditions	Yield
With KOH In methanol; water Ni(ClO4)2*6H2O mixed with 1,10-phenanthroline-2,9-dicarboxylic acid; pH adjusted to about 7 (aq. KOH); filtered; allowed to stand at room temp.; solvent was slowly evapd.; elem. anal.;	60%

3-(1H-imidazol-1-yl)propan-1-amine (5036-48-6) + 1,10-phenanthroline-2,9-dicarboxylic acid (57709-61-2) → 2,9-bis(N-(1-imidazolyl)propylaminocarbonyl)-1,10-phenanthroline

Conditions	Yield
Stage #1: 1,10-phenanthroline-2,9-dicarboxylic acid With 1,1'-carbonyldiimidazole In N,N-dimethyl-formamide at 45℃; for 2h; Stage #2: 3-(1H-imidazol-1-yl)propan-1-amine In N,N-dimethyl-formamide at 20℃; for 96h;	59%

n-dioctylamine (1120-48-5) + 1,10-phenanthroline-2,9-dicarboxylic acid (57709-61-2) → N,N′-dioctyl-N,N′-dioctyl-2,9-diamide-1,10-phenanthroline

Conditions	Yield
Stage #1: 1,10-phenanthroline-2,9-dicarboxylic acid With thionyl chloride for 6h; Reflux; Stage #2: n-dioctylamine With N-ethyl-N,N-diisopropylamine In dichloromethane for 6h; Reflux;	59%

dysprosium(III) nitrate hexahydrate + silicotungstic acid hydrate + 1,10-phenanthroline-2,9-dicarboxylic acid (57709-61-2) → 4C14H6N2O4(2-)*O40SiW12(4-)*18H2O*4Dy(3+)

Conditions	Yield
Stage #1: dysprosium(III) nitrate hexahydrate; silicotungstic acid hydrate; 1,10-phenanthroline-2,9-dicarboxylic acid In water for 0.5h; Stage #2: In water for 0.5h; Stage #3: With ammonium metavanadate; sodium hydroxide In water at 130℃; for 72h; pH=2.5; Autoclave;	55%

ZnCl2*5H2O + water (7732-18-5) + 1,10-phenanthroline-2,9-dicarboxylic acid (57709-61-2) + acetonitrile (75-05-8) → C28H12N4O8Zn(2-)*2CH3NO2*2H2O*2H3O(1+)

Conditions	Yield
Stage #1: ZnCl2*5H2O; water; 1,10-phenanthroline-2,9-dicarboxylic acid; acetonitrile for 0.5h; High pressure; Stage #2: at 130℃; for 72h; Autoclave;	53%

dysprosium(III) nitrate hexahydrate + α-H4SiMo12O40*xH2O + water (7732-18-5) + 1,10-phenanthroline-2,9-dicarboxylic acid (57709-61-2) → 2[Dy4(PDA)4(H2O)11(SiMo12O40)]*7H2O

Conditions	Yield
Stage #1: dysprosium(III) nitrate hexahydrate; α-H4SiMo12O40*xH2O; water; 1,10-phenanthroline-2,9-dicarboxylic acid for 0.5h; Stage #2: With sodium hydroxide at 130℃; for 72h; pH=1.8; Autoclave; High pressure;	51.44%

cerium(III) chloride heptahydrate + 1,10-phenanthroline-2,9-dicarboxylic acid (57709-61-2) → 3Ce(3+)*3C14H6N2O4(2-)*3C14H7N2O4(1-)

Conditions	Yield
In water at 180℃; for 24h; Autoclave;	47%

n-Octylamine (111-86-4) + 1,10-phenanthroline-2,9-dicarboxylic acid (57709-61-2) → 2,9-bis(N-octylaminocarbonyl)-1,10-phenanthroline

Conditions	Yield
Stage #1: 1,10-phenanthroline-2,9-dicarboxylic acid With thionyl chloride for 6h; Reflux; Stage #2: n-Octylamine With N-ethyl-N,N-diisopropylamine In dichloromethane for 6h; Reflux;	46%

1,10-phenanthroline-2,9-dicarboxylic acid (57709-61-2) + 3-(2-methyl-1H-imidazol-1-yl)propan-1-amine (2258-21-1) → 2,9-bis(N-(1-(2-methylimidazolyl))propylaminocarbonyl)-1,10-phenanthrolin

Conditions	Yield
Stage #1: 1,10-phenanthroline-2,9-dicarboxylic acid With 1,1'-carbonyldiimidazole In N,N-dimethyl-formamide at 45℃; for 2h; Stage #2: 3-(2-methyl-1H-imidazol-1-yl)propan-1-amine In N,N-dimethyl-formamide at 20℃; for 96h;	46%

Upstream product

• 484-11-7 2.9-dimethyl-1,10-phenanthroline 
• 39069-02-8 2,9-dibromo-1,10-phenanthroline 
• 78831-40-0 2,9-bis(tribromomethyl)-1,10-phenanthroline 
• 78831-41-1 2,9-Bis(trichloromethyl)-1,10-phenanthroline 
• 57709-62-3 1,10-phenanthroline-2,9-dicarboxaldehyde 

Downstream Products

• 516462-64-9 bis(pentafluorophenyl)-1,10-phenanthroline-2,9-dicarboxylate 
• 57709-62-3 1,10-phenanthroline-2,9-dicarboxaldehyde 
• 1301127-07-0 N,N'-bis(phenyl-4-ethoxydimethylamino)-1,10-phenanthroline-2,9-carboxamide 
• 1301127-06-9 N,N'-bis(phenyl-4-ethoxymorpholine)-1,10-phenanthroline-2,9-carboxamide 
• 1266331-38-7 N,N'-bis(phenyl-4-ethoxypyrrole)-1,10-phenanthroline-2,9-carboxamide 
• 1266331-37-6 N,N'-bis(phenyl-4-ethoxypiperidine)-1,10-phenanthroline-2,9-carboxamide 
• 1266331-36-5 N,N'-bis(4-aminophenol)-1,10-phenanthroline-2,9-carboxamide 
• 78831-36-4 1,10-phenanthroline-2,9-dimethanol 

Relevant articles and documents

Highly Efficient Trivalent Americium/Europium Separation by Phenanthroline-Derived Bis(pyrazole) Ligands

The synthesis, Eu3+ complexation, and solvent extraction of Am3+ and Eu3+ from nitric acid solutions by tetradentate phenanthroline-derived bis(pyrazole) (BPPhen) ligands were described. By using meta-nitrobenzotrifluoride as diluent, BPPhen ligands in combination with 2-bromohexanoic acid extracted Am3+ and Eu3+ with remarkably high efficiency, excellent selectivity, and fast extraction kinetics. Stripping posed no issues. The ligands also showed excellent hydrolytic stability and acid tolerance. 2-Bromohexanoic anion neutralized the charge and increased the lipophilicity of the extracted ion pair. The extraction conformed to a cation exchange model. Slope analysis demonstrated the extraction of 1:2 metal/ligand complexes. Analyses by electrospray ionization mass spectrometry, time-resolved laser-induced fluorescence spectroscopy, Raman, and Fourier transform infrared techniques indicated that the composition of the extracted species is [Eu(nOct-BPPhen)2(H2O)]3+. The formation of 1:2 complexes was also confirmed by UV-vis spectroscopic titration and microcalorimetric titration methods. Meanwhile, the stability constants (K) and the thermodynamic parameters (ΔH, ΔS, ΔG) for the complexation of Eu3+ with nOct-BPPhen were presented too.

Towards understanding the correlation between UO22+ extraction and substitute groups in 2,9-diamide-1,10-phenanthroline

2,9-Diamide-1,10-phenanthroline (DAPhen) ligands represent a new family of tetradentate extractants given their strong affinity to actinides and the CHON principle. Among this family, N,N′-diethyl-N,N′-ditolyl-2,9-diamide-1,10-phenanthroline (Et-Tol-DAPhen), initially reported by us, exhibits excellent selectivity towards actinides (U, Th, Am, Pu) over lanthanides and thus can be potentially applied in the group actinide extraction (GANEX) process for the group separation of actinides. In this article, by tailoring the lengths of alkyl chains, we synthesized other four DAPhen ligands with different substitute groups in the diamide moieties, and characterized the relationship between properties and substitute groups of DAPhen ligand. The extraction results show that three of the ligands exhibit high performance in UO22+ extraction from an acidic solution and the extracted UO22+ can be easily stripped by only using ultrapure water. Spectrophotometry titration confirms that UO22+ combined with all the four ligands in 1:1 mode. The extended X-ray absorption finestructure (EXAFS) study shows that six donor atoms comprise the first equatorial shell of the UO22+ ions bonded by the DAPhen ligands, among which two nitrogen and two oxygen atoms are from the DAPhen ligand, while other two oxygen atoms are from one nitrate ions. This article promises to provide basic data for assessing the feasibility of this kind of DAPhen ligands applied in actinides separation from nuclear wastes.

A novel 1,10-phenanthroline based chemosensor for differential metal ion sensing and constructing molecular logic gates

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Selective separation of trivalent f-ions using 1,10-phenanthroline-2,9-dicarboxamide ligands in ionic liquids

1,10-Phenanthroline-2,9-dicarboxamide complexants decorated with alkyl chains and imidazolium cations have been studied for extraction of trivalent f-ions into imidazolium ionic liquids. The dicationic complexants are shown to extract Am over Eu with separation factors >50 and high extraction efficiencies. The different size selectivities for lanthanide ions were observed for these two types of complexants, highlighting the importance of the positive charge in controlling both extraction efficiencies and extraction selectivities.

Palladium-Catalyzed Butoxycarbonylation of Polybromo(hetero)arenes: A Practical Method for the Preparation of (Hetero)arenepolycarboxylates and -carboxylic Acids

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Phenanthroline-derived dipyrazole extractant as well as preparation method and application thereof

The invention discloses a double-pyrazole extracting agent derived from o-phenanthroline with the following structural general formula, and a preparation method and application of the double-pyrazoleextracting agent. In the formula, R is any one selected from n-octyl, n-butyl, isobutyl, ethyl, pyridyl and phenyl. The double-pyrazole extracting agent derived from the o-phenanthroline provided by the invention has a unique rigid structure and an alkyl chain for improving the solubility, and simultaneously only four elements of C, H, O and N are contained, so that the extraction kinetics of a separation extraction system can be greatly increased, the extraction capacity of an organic phase can be increased, secondary pollutants cannot be produced, and thus the environmental protection is facilitated. The extraction agent can be used to separate Ans (actinide elements)/Lns (lanthanide elements), and can not only form a separation extraction system of the Ans/Lns, but also can be used to form a separation reverse extraction system of the Ans/Lns.