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66-71-7

Basic Information
CAS No.: 66-71-7
Name: o-Phenanthroline
Article Data: 74
Molecular Structure:
Molecular Structure of 66-71-7 (o-Phenanthroline)
Formula: C12H8N2
Molecular Weight: 181.217
Synonyms: 1,10-o-Phenanthroline;4,5-Diazaphenanthrene;β-Phenanthroline;phenanthroline;
EINECS: 200-629-2
Density: 1.25 g/cm3
Melting Point: 114-117°C(lit.)
Boiling Point: 365.089 °C at 760 mmHg
Flash Point: 164.756 °C
Solubility: slightly soluble in water
Appearance: off-white powder
Hazard Symbols: ToxicT,DangerousN
Risk Codes: 25-50/53
Safety: 45-60-61
Transport Information: UN 2811 6.1/PG 3
PSA: 25.78000
LogP: 2.78300
Synthetic route
122108-94-5

{(C12H8N2)((C6H5)3P)Cu(O2CC5H7N2)(H2O)}

A

66-71-7

1,10-Phenanthroline

B

{copper(I)-3,5-dimethylpyrazolate}(n)

Conditions
ConditionsYield
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);
3188-84-9

1,2,3,4-tetrahydro-1,10-phenanthroline

66-71-7

1,10-Phenanthroline

Conditions
ConditionsYield
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

A

66-71-7

1,10-Phenanthroline

B

14126-11-5

{Ru(1,10-phenanthroline)3}(NO3)2*2H2O

Conditions
ConditionsYield
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]

58034-59-6

{Ag(1,10-phenanthroline)2}ClO4

sodium perchlorate

A

66-71-7

1,10-Phenanthroline

B

{Ru(phan)3}(ClO4)2*H2O

Conditions
ConditionsYield
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%
942267-02-9

(Z)-1,2-di(2-bromopyridin-3-yl)ethene

66-71-7

1,10-Phenanthroline

Conditions
ConditionsYield
With copper In N,N-dimethyl-formamide for 5h; Ullmann coupling; Heating;67%
65115-91-5

5,6-epoxy-5,6-dihydro-[1,10]phenanthroline

66-71-7

1,10-Phenanthroline

Conditions
ConditionsYield
With 2,4,6-trimereaptotriazine, trisodium salt, nonahydrate In ethanol65%

2,3-dinitrobenzene-1,4-dicarbaldehyde

75-07-0

acetaldehyde

66-71-7

1,10-Phenanthroline

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

ruthenium(III) chloride trihydrate

di (1,10-phenanthroline)silver(I) nitrate

A

66-71-7

1,10-Phenanthroline

B

14126-11-5

{Ru(1,10-phenanthroline)3}(NO3)2*2H2O

Conditions
ConditionsYield
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

58034-59-6

{Ag(1,10-phenanthroline)2}ClO4

sodium perchlorate

A

66-71-7

1,10-Phenanthroline

B

{Ru(phan)3}(ClO4)2*H2O

Conditions
ConditionsYield
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

75-07-0

acetaldehyde

66-71-7

1,10-Phenanthroline

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

Reported in EPA TSCA Inventory.

Specification

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%.

1,10-Phenanthroline can react with butyllithium to produce 2,9-di-n-butyl-1,10-phenanthroline

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.