5144-89-8

Basic information

• Product Name: 1,10-Phenanthroline monohydrate
• Synonyms: 1,10-Phenanthroline hydrate; o-Phenanthroline,Monohydrate; 1,10-Phenanthroline,Monohydrate; 1,10-phenanthroline hydrate (1:1); Orthophenanthroline Monohydrate; O-Phenanthroline Monohydrate
• CAS NO: 5144-89-8
• Molecular Formula: C₁₂H₈N₂*H₂O
• Molecular Weight: 198.2206
• EINECS: 200-629-2
• Product Categories: Miscellaneous;Analytical Chemistry;Chelating Reagents;Environmentally-friendly Oxidation;Ligands (Environmentally-friendly Oxidation);Phenanthrolines;Synthetic Organic Chemistry;ACS Grade;Analytical Reagents;Analytical/Chromatography;Bioactive Small Molecules;Building Blocks;Cell Biology;Chemical Synthesis;Essential Chemicals;Heterocyclic Building Blocks;Indicators;Inorganic Salts;N-Containing;Others;P;Redox Indicators;Research Essentials;Solutions and Reagents;Titration
• Mol File: 5144-89-8.mol
• Article Data: 0

Chemical Properties

• Melting Point: 97-101℃
• Density: 1.10
• Vapor Density: 6.2 (vs air)
• Storage Temp.: Store at RT.
• Solubility: methanol: soluble200MM (Stock solution is stable for months at –20° C.)
• Water Solubility: <0.01 g/100 mL at 21℃
• Stability: Stable. Incompatible with iron, other heavy metals, strong oxidizing agents, strong acids.
• Merck: 14,7214
• BRN: 4008096
• CAS DataBase Reference: 1,10-Phenanthroline monohydrate(CAS DataBase Reference)
• NIST Chemistry Reference: 1,10-Phenanthroline monohydrate(5144-89-8)
• EPA Substance Registry System: 1,10-Phenanthroline monohydrate(5144-89-8)

Safety Data

• Hazard Codes: T:Toxic;;
• Statements: R25:; R50/53:
• Safety Statements: S45:; S60:; S61:
• RIDADR: UN 2811 6.1/PG 3
• WGK Germany: 3
• RTECS: SF8437000
• TSCA: Yes
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 5144-89-8(Hazardous Substances Data)

Usage

Chemical Properties

white crystals or powder

Uses

Different sources of media describe the Uses of 5144-89-8 differently. You can refer to the following data:
1. 1,10-Phenanthroline monohydrate is useful to study the DNA-protein interactions due to its nuclease activity. It is used as a redox indicator and reagent for spectrophotometric assay of silver. It acts as a chelating ligand for the determination of Fe, Pd and V. It also acts as a matrix metalloproteinase inhibitor. It is a photometric reagent for iron, which forms a red chelate with ferrous (iron II) ion.
2. When complexed with copper, it possesses nuclease activity that has been used to study DNA-protein interactions.1,10-Phenanthroline monohydrate is an aromatic nitrogen heterocycle that may be used as a chelating agent in the preparation of metal-chelate complexes.

General Description

White crystalline powder or solid. Slight odor.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

1,10-Phenanthroline hydrate is incompatible with strong oxidizers. 1,10-Phenanthroline hydrate is also incompatible with strong acids. 1,10-Phenanthroline hydrate forms complex compounds with ferrous ions. .

Fire Hazard

Flash point data for 1,10-Phenanthroline hydrate are not available. 1,10-Phenanthroline hydrate is probably combustible.

Biochem/physiol Actions

Metalloprotease inhibitor; chelates iron, zinc and other divalent metals. Effective concentration 1-10 mM.

Purification Methods

Crystallise its picrate (m 191o) from EtOH; then the free base is liberated with aqueous alkali, dried at 78o/8mm over P2O5 and crystallised from pet ether (b 80-100o). [Cumper et al. J Chem Soc 1188 1962.] It can be purified by zone melting. It has also been crystallised from hexane, *benzene/pet ether (b 40-60o) or sodium-dried *benzene, dried and stored over H2SO4. The monohydrate is obtained by crystallisation from aqueous EtOH or ethyl acetate. It has been crystallised from H2O (300 parts) to give the monohydrate m 102-103o which sublimes at 10-3mm [Fielding & LeFevre J Chem Soc 1811 1951.] The anhydrous compound has m 118o (after drying at high vacuum at 80o) and is also obtained by recrystallisation from pet ether or *C6H6 (70 parts) and drying at 78o/8mm. [UV: Badger et al. J Chem Soc 3199 1951.] IthasapKainH2Oof 4.857 (25o) or 5.02 (20o) and 4.27 in 50% aqueous EtOH (20o). [Albert et al. J Chem Soc 2240 1948]. [Beilstein 23 H 227, 23 II 235, 23/8 V 419.]

Synthetic route

manganese (II) acetate tetrahydrate (6156-78-1) + 1,10-phenanthroline hydrate (5144-89-8) → {Mn3(O2CCH3)6(1,10-phenanthroline)2}

Conditions	Yield
In N,N-dimethyl-formamide stirred for 10 min; filtered, washed with DMF, acetone and diethyl ether, dried in vac.; elem. anal.;	99%

tetrakis(acetonitrile)copper(I)tetrafluoroborate + 1,10-phenanthroline hydrate (5144-89-8) + 1,2-bis-(diphenylphosphino)ethane (1663-45-2) → (1,10-phenanthroline)(1,2-bis(diphenylphosphino)ethane)copper(I) tetrafluoroborate (498584-34-2)

Conditions	Yield
In dichloromethane (N2); Cu complex was reacted with P ligand in CH2Cl2; phenanthroline wasadded after dissolution; mixt. was stirred for 1 h; solvent removed (vac.); Et2O added; pptd.; washed (Et2O);	99%

hydrogenchloride (7647-01-0) + sodium tetrachloropalladate(II) + 1,10-phenanthroline hydrate (5144-89-8) → [palladium(II)dichloride(1,10-phenanthroline)] (14783-10-9)

Conditions	Yield
In water stirring Na2PdCl4 with 1 equiv. ligand and excess HCl (80°C, 30 min); standing at room temp. for several h, collection (filtration), washing (water, MeOH); elem. anal.;	99%

1,10-phenanthroline hydrate (5144-89-8) + copper (12775-96-1, 15158-11-9, 15721-63-8, 16941-75-6, 17493-86-6, 19498-52-3, 20499-83-6, 20499-84-7, 20499-85-8, 20499-86-9, 20573-10-8, 20573-11-9, 21595-51-7, 21595-52-8, 22206-52-6, 26445-28-3, 28959-95-7, 37362-93-9, 39417-05-5, 54603-16-6, 54603-23-5, 54603-32-6, 54603-40-6, 54603-48-4, 54603-81-5, 54603-89-3, 56316-56-4, 95985-91-4, 122297-32-9, 7440-50-8) + copper(II) nitrate + 1,2-bis-(diphenylphosphino)ethane (1663-45-2) → [Cu(1,2-bis(diphenylphosphino)ethane)(1,10-phenanthroline)]NO3 (498584-36-4)

Conditions	Yield
In acetonitrile (N2); mixt. of Cu(NO3)2 and Cu in CH3CN was stirred for 2 h; filtered under N2; P ligand and phenanthroline were subsequently added to filtrate;soln. was stirred for 15 min; solvent removed (vac.); extd. (CH2Cl2); CH2Cl2 removed (vac.); Et2O added; washed (Et2O);	99%

tetrakis(acetonitrile)copper(I) perchlorate (14057-91-1) + 1,10-phenanthroline hydrate (5144-89-8) + 1,2-bis-(diphenylphosphino)ethane (1663-45-2) → [Cu(1,2-bis(diphenylphosphino)ethane)(1,10-phenanthroline)]ClO4 (498584-33-1)

Conditions	Yield
In dichloromethane (N2); Cu complex was reacted with P ligand in CH2Cl2; phenanthroline wasadded after dissolution; mixt. was stirred for 1 h; solvent removed (vac.); Et2O added; pptd.; washed (Et2O);	99%

1,10-phenanthroline hydrate (5144-89-8) → 5,6-epoxy-5,6-dihydro-[1,10]phenanthroline (65115-91-5)

Conditions	Yield
With industrial bleach (pH 8.2-8.3 with conc. HCl); tetra(n-butyl)ammonium hydrogensulfate In chloroform; water	98%

copper(II) acetate monohydrate (6046-93-1) + 1,10-phenanthroline hydrate (5144-89-8) → (1,10-Phen)Cu(OAc)2

Conditions	Yield
In ethanol addn. of a soln. of 1,10-phenanthroline*H2O in ethanol to a filtered soln. of Cu(OAc)2*H2O in ethanol; stirring the soln. for 1 h, evapn. of the solvent, washing the residue with benzene and drying in vacuo, elem. anal.;	98%

nickel(II) chloride hexahydrate + dicesium dodecachloro-closo-dodecaborate + 1,10-phenanthroline hydrate (5144-89-8) → [nickel(II)(1,10-phenanthroline)3]B12Cl12

Conditions	Yield
In ethanol; water addn. of a soln. of organic compound in boiling ethanol to a soln. of Ni-salt and B-compound in water with stirring; filtn., washing (warm water, hot ethanol, absolute ether), drying over P2O5, elem. anal.;	98%

manganese(II) chloride tetrahydrate + caesium [3,3'-commo-bis(η5-nonahydro-1,2-dicarba-3-nickel-closo-decarborate)] + 1,10-phenanthroline hydrate (5144-89-8) → [Mn(II)(1,10-phenantroline)3][bis(η5-1,2-B9C2H11)nickeliate(III)]2

Conditions	Yield
With CH3COOH; CH3COONa; Na2SO3 In hydrogenchloride; water soln. of MnCl2*4H2O in acetate buffer (pH 4.56) mixed with phen*H2O soln. in aq. HCl (H2O:HCl=1:4), Na2SO3 added, heated at 70°C, hot soln. Cs-Ni-complex in H2O added, stored for 12 h; ppt. filtered off, washed with H2O and C6H6, dried under vac. at 70°C; elem. anal.;	98%

manganese(II) chloride tetrahydrate + cesium 1,2;1',2'-trans-bis[nonahydro-closo-decaborate] + 1,10-phenanthroline hydrate (5144-89-8) → [tris(1,10-phenanthroline)manganese(II)] 1,2;1',2'-trans-bis[nonahydro-closo-decaborate]

Conditions	Yield
With acetate buffer In water Mn salt dissolved in acetate buffer (pH 4.56); 1,10-phenanthroline monohydrate dissolved with stirring in acetate buffer soln.; solns. combined with stirring; soln. heated to 70°C; hot soln. of Cs2B20H18 in H2O added with stirring; ppt. formed; suspn. allowed to coagulate for 12 h; ppt. filtered off on glass frit; washed (H2O); dried (vac., 70°C);	98%

manganese(II) chloride tetrahydrate + cesium nido-1,2-dicarbaundecaborate + 1,10-phenanthroline hydrate (5144-89-8) → tris-(1,10-phenanthroline)manganese(II) nido-1,2-dicarbaundecaborate

Conditions	Yield
With HCl In water Mn compd. dissolved (acetate buffer), mixed with a soln. of ligand (water, dilute HCl (drops)) under stirring, heated to 70°C, a hot soln. of borate added, kept for 12 h at 70°C; ppt. filtered, washed (water), dried (vac., 70°C); elem. anal.;	98%

hydrogenchloride (7647-01-0) + potassium tetrachloroplatinate(II) (10025-99-7) + 1,10-phenanthroline hydrate (5144-89-8) → dichloro(1,10-phenanthroline)platinum(II) (18432-95-6)

Conditions	Yield
In water elem. anal.;	97.7%

1,10-phenanthroline hydrate (5144-89-8) + cobalt(II) perchlorate hexahydrate + thiourea (17356-08-0) → {Co(C12H8N2)3(SC(NH2)2)}(2+)*2(ClO4)(1-) = Co(ClO4)2(C12H8N2)3(SC(NH2)2)

Conditions	Yield
In ethanol Co-compound, PHA and Tu were suspended in EtOH; the product was stirred in its mother soln. for many h; washed (EtOH, Et2O); elem.anal.;	97%

nitric acid (7697-37-2) + 1,10-phenanthroline hydrate (5144-89-8) + palladium (7440-05-3) → Pd(phen)(ONO2)2 (31476-92-3)

Conditions	Yield
With water In ethanol; nitric acid addn. of a soln. of 1,10-phenanthroline*H2O in ethanol to the aq. HNO3 soln. obtained after dissolution of Pd black in concd. HNO3 and dilutionwith water; stirring the soln. at room temp. for 2 h, filtration of the yellow ppt., washing with ethanol and drying in vacuo, elem. anal.;	97%

trans-(S,S)-[PdBr2(NH2CH(CO2Me)CH2C6H4-I-2)2] + 1,10-phenanthroline hydrate (5144-89-8) → (PdBr2(phen)) (41876-11-3)

Conditions	Yield
In dichloromethane byproducts: IC6H4CH2CH(CO2CH3)NH2; ligand added to a soln. of Pd complex, stirred for 3 h at room temp.; filtered, washed (Et2O), air-dried;	97%

1,10-phenanthroline hydrate (5144-89-8) + palladium dichloride → [palladium(II)dichloride(1,10-phenanthroline)] (14783-10-9)

Conditions	Yield
With hydrogenchloride In ethanol; water addn. of concd. HCl to an aq. PdCl2 soln., filtration of the soln. and addn. of a soln of 1,10-phenanthroloine*H2O in ethanol to the filtered soln.; stirring for 2 h, filtering the ppt., washing with ethanol and drying in vacuo, elem. anal.;	96%

cadmium(II) bis(tri-tert-butoxysilanethiolate) + 1,10-phenanthroline hydrate (5144-89-8) → (1,10-phenanthroline)cadmium(II) bis(tri-tert-butoxysilanethiolate) (142372-83-6)

Conditions	Yield
In benzene mixing solns. of Cd-complex and ligand in benzene gives instantaneously a white voluminous ppt., addn. of more benzene, refluxing under Ar until a clear soln. is obtained; slow cooling to room temp., pptn., washing with benzene, drying in vacuo, elem. anal.;	96%

chloro{2-(dimethylamino)-1-methylpropyl-C,N}(dimethylamine)palladium(II) (91409-21-1) + 1,10-phenanthroline hydrate (5144-89-8) → {2-(dimethylamino)-1-methylpropyl-C,N}(phenanthroline)palladium(II) chloride

Conditions	Yield
In acetone added at 0°C, stirred for 10 min; evaporated to dryness; elem. anal.;	96%

[{Au(C6Cl5)2}Ag]n + 1,10-phenanthroline hydrate (5144-89-8) → Au(1+)*Ag(1+)*2C6Cl5(1-)*N2C12H8=(AuAg(C6Cl5)2(N2C12H8))

Conditions	Yield
In hexane; dichloromethane to a suspn. of (AuAg(C6Cl5)2)n in dichloromethane added 1,10-phenantroline in hexane and stirred at room temp. for 24 h; solid filtered off and washed with diethylether; elem. anal.;	96%

chlorotris(triphenylphosphine)palladium(II) hexafluorophosphate * acetone + 1,10-phenanthroline hydrate (5144-89-8) → chlorobis(triphenylphosphine)(1,10-phenanthroline)palladium(II) hexafluorophosphate (101019-70-9)

Conditions	Yield
In acetone to suspn. of Pd complex ligand was added, standing for 30 min; soln. was reduced in vac., pptd. with ether, elem. anal.;	96%

caesium cobalt(III)bis(1,2-dicarboilide) + manganese(II) chloride tetrahydrate + 1,10-phenanthroline hydrate (5144-89-8) → tris-(1,10-phenanthroline)manganese(II) 3,3-commo-bis[η5-1,2-dicarba-(3)-cobalt(III)-closo-dodecaborate]

Conditions	Yield
With HCl In water Mn compd. dissolved (acetate buffer), mixed with a soln. of ligand (water, dilute HCl (drops)) under stirring, heated to 70°C, a hot soln. of borate added, kept for 12 h; ppt. filtered, washed (water), dried (vac., 70°C); elem. anal.;	96%

oxalic acid dihydrate (6153-56-6) + copper(II) acetate monohydrate (6046-93-1) + germanium dioxide + 1,10-phenanthroline hydrate (5144-89-8) → [Cu(1,10'-phenanthroline)3][tris(oxalate-O,O')germanate] (947503-45-9)

Conditions	Yield
In water addn. of distld. water to 1:3:1:3 mixt. of germanium dioxide, oxalic acid, copper acetate and phenanthroline, stirring for 30 min at room temp.,heating at 100°C for 72 h; isolation of crystals, washing with distld. water, filtration, air drying, elem. anal.;	95.6%

Ir(OClO3)(C6F4C6H6)2 (90634-69-8) + 1,10-phenanthroline hydrate (5144-89-8) → {Ir(tetrafluorobenzobarrelene)(1,10-phenanthroline)}ClO4 (90634-76-7)

Conditions	Yield
In dichloromethane (N2); complex suspn. treated for 30 min with stoich. amt. of ligand; concd. (vac.), pptd. (ether), filtered off, washed (ether), dried in vac.; elem. anal.;	95%

silver tetrafluoroborate (14104-20-2) + {IrCl(tetrafluorobenzobarrelene)2} (88478-63-1) + 1,10-phenanthroline hydrate (5144-89-8) → [Ir(C6F4C6H6)(C12H8N2)](1+)*BF4(1-)=[Ir(C6F4C6H6)(C12H8N2)]BF4 (90634-85-8)

Conditions	Yield
In acetone byproducts: AgCl; under N2 and protected from daylight complex suspn. in acetone or CH2Cl2 treated for 30 min with ligand and with AgBF4 in acetone; AgCl filtered off, filtrate concd. (vac.), pptd. (ether), filtered off,washed with ether, dried in vac.; elem. anal.;	95%

2-methyllactic acid (594-61-6) + 1,10-phenanthroline hydrate (5144-89-8) + zinc(II) carbonate (743369-26-8) → [Zn(2-methyllactate)(1,10-phenanthroline)2](2-methyllactate)*4H2O

Conditions	Yield
In ethanol mixt. of ZnCO3, α-hydroxycarboxylic acid, and diamine in EtOH refluxed for 4 h, allowed to cool to room temp., stirred for 1 wk; recrystd. from nethanol/isopropanol (1/1), dried under vac.; elem. anal.;	95%

lead(II) nitrate + copper(II) choride dihydrate + 1,10-phenanthroline hydrate (5144-89-8) → poly[chlorobis(1,10-phenanthroline)copper(II) trichloroplumbate(II)]

Conditions	Yield
With HCl In water; N,N-dimethyl-formamide High Pressure; solvothermal synthesis; mixt. of Pb(NO3)2, phen*H2O, CuCl2*2H2O (0.5:1:0.5 mmol) in DMF with 36 % aq. HCl (1 ml) heated in Teflon-lined stainless steel vessel at 120°C for 3 d; cooled to room temp. (rate 3°C/h); elem. anal.;	95%

cyclo-tetrakis-{tri-tert-butoxysilanethiolatocopper(I)} + 1,10-phenanthroline hydrate (5144-89-8) → ((CH3)3CO)3SiS(1-)*Cu(1+)*C12H8N2=((CH3)3CO)3SiSCu*C12H8N2

Conditions	Yield
In benzene addn. of phen*H2O to anhyd. benzene, refluxing (until a clear soln. was obtained), addn. of soln. of ((t-BuO)3SiSCu)4 (colour change to deep red), left to stand, 1 day, room temp., pptn.; filtered, washed (hexane), vac. dried, elem. anal.;	94%

erbium(III) nitrate pentahydrate + 1,10-phenanthroline hydrate (5144-89-8) → trinitrato-bis-(1,10-phenantroline)erbium(III)

Conditions	Yield
In isopropyl alcohol soln. of Er-comp. in isopropanol treated with isopropanol-soln. of 2,2'-1,10-phenantroline monohydrate, mixt.allowed to stay for 24 h; filtered, crystals dried over P4O10, elem. anal.;	94%

bis(dimethylphenylphosphine)bis(monothiobenzoato)ruthenium(II) (81704-56-5, 68249-87-6) + 1,10-phenanthroline hydrate (5144-89-8) → bis(dimethylphenylphosphine)bis(monothiobenzoato)(1,10-phenanthroline)ruthenium(II) (74244-05-6, 74215-94-4)

Conditions	Yield
In ethanol reflux for 2 h under N2; the volume of the soln. reduced, after standing for some h the product filtered; elem. anal.;	94%

potassium tetrachloroplatinate(II) (10025-99-7) + dicesium dodecachloro-closo-dodecaborate + 1,10-phenanthroline hydrate (5144-89-8) → [platinum(II)(1,10-phenanthroline)2]B12Cl12

Conditions	Yield
In ethanol; water addn. of a soln. of organic compound in ethanol to a soln. of B-compound in water, addn. of a soln. of Pt-complex in water, keeping the mixtureat 35°C. for 24 h; filtn., washing (warm water, ethanol, absolute ether), drying in vac. over P2O5, elem. anal.;	94%

Downstream Products

• 116287-98-0 2,9-bis-(4-methylphenyl)-1,10-phenanthroline 
• 18432-95-6 dichloro(1,10-phenanthroline)platinum(II) 
• 19319-86-9 dibromo(1,10-phenanthroline)copper(II) 
• 498584-34-2 (1,10-phenanthroline)(1,2-bis(diphenylphosphino)ethane)copper(I) tetrafluoroborate 
• 14783-10-9 [palladium(II)dichloride(1,10-phenanthroline)] 
• 144082-24-6 Zr⁽⁴⁺⁾*O₂^(2-)*C₆H₄CH₂COO(COO)^(2-)*C₁₂H₈N₂ = {Zr(O₂)(C₉H₆O₄)(C₁₂H₈N₂)} 
• 150293-39-3 Pd⁽²⁺⁾*C₉H₆NCH₂^(1-)*C₆F₅^(1-)*C₁₂H₈N₂={Pd(C₉H₆NCH₂)(C₆F₅)(C₁₂H₈N₂)} 
• 108548-10-3 dihydrido(1,10-phenanthroline)bis(triphenylphosphine)iridium(III) trifluoromethanesulphonate