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o-Phenanthroline

CAS No.
66-71-7
Chemical Name:
o-Phenanthroline
Synonyms
1,10-PHENANTHROLINE;phen;1,10-Phen;10-Phenanthroline;1,10-Fenanthrolin;ORTHOPHENANTHROLINE;1,10-Phenanthroline anhydrate;4,5-Phenanthroline;1,1-Phenanthroline;1,10-o-Phenanthroline
CBNumber:
CB4283203
Molecular Formula:
C12H8N2
Molecular Weight:
180.21
MDL Number:
MFCD00011678
MOL File:
66-71-7.mol
MSDS File:
SDS
Last updated:2024-04-24 17:21:45

o-Phenanthroline Properties

Melting point 114-117 °C(lit.)
Boiling point >330°C
Density 1.1836 (rough estimate)
refractive index 1.5200 (estimate)
Flash point >330°C
storage temp. Store below +30°C.
solubility 2.69g/l
pka 4.84(at 25℃)
form Powder
color White to light yellow or light pink
Water Solubility slightly soluble
Sensitive Hygroscopic
Merck 14,7214
BRN 126461
Stability Stable. Hygroscopic. Store under nitrogen. Incompatible with strong acids, strong oxidizing agents.
InChIKey DGEZNRSVGBDHLK-UHFFFAOYSA-N
CAS DataBase Reference 66-71-7(CAS DataBase Reference)
EWG's Food Scores 1
FDA UNII W4X6ZO7939
NIST Chemistry Reference o-Phenanthroline(66-71-7)
EPA Substance Registry System 1,10-Phenanthroline (66-71-7)

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictogramsGHS hazard pictograms
GHS06,GHS09
Signal word  Danger
Hazard statements  H301-H410
Precautionary statements  P264-P270-P273-P301+P310-P391-P405
Hazard Codes  T,N
Risk 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
HS Code  29339990
Toxicity dni-hmn:leu 5 mg/L ONCOBS 46,193,89
NFPA 704
1
2 1

o-Phenanthroline price More Price(40)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich 131377 1,10-Phenanthroline ≥99% 66-71-7 2.5g $27.7 2024-03-01 Buy
Sigma-Aldrich 131377 1,10-Phenanthroline ≥99% 66-71-7 5g $43.1 2024-03-01 Buy
TCI Chemical P2099 1,10-Phenanthroline 66-71-7 5G $29 2024-03-01 Buy
TCI Chemical P2099 1,10-Phenanthroline 66-71-7 25G $99 2024-03-01 Buy
Alfa Aesar A13163 1,10-Phenanthroline, 99%, may contain up to 1.5% water 66-71-7 5g $42.1 2024-03-01 Buy
Product number Packaging Price Buy
131377 2.5g $27.7 Buy
131377 5g $43.1 Buy
P2099 5G $29 Buy
P2099 25G $99 Buy
A13163 5g $42.1 Buy

o-Phenanthroline Chemical Properties,Uses,Production

Description

o-Phenanthroline is a white crystalline powder and serves as an organic intermediate. It has multiple uses, acting as both a redox indicator and a reagent for the determination of various metals such as ferrous, palladium, vanadium, copper, and iron.

Chemical Properties

Monohydrate is a white crystalline powder. The melting point is 93-94°C, the melting point of anhydrous is 117°C, soluble in 300 parts of water, 70 parts of benzene, soluble in alcohol and acetone.

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

o-Phenanthroline is a commonly used redox indicator and also a bidentate ligand. It has been widely used in transition metal-catalyzed cross-coupling reactions and C?H bond activation reactions. It also acts as a chelating agent, forming complexes with most metal ions. In addition, it functions as a ligand employed in the spectrophotometric determination of metals and photocatalytic reduction of carbon dioxide.

Uses

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.

Preparation

1,10-Phenanthroline is prepared by heating o-phenylenediamine, glycerin, nitrobenzene and concentrated sulfuric acid.

Definition

ChEBI: 1,10-phenanthroline is a phenanthroline. It has a role as an EC 3.4.19.3 (pyroglutamyl-peptidase I) inhibitor and an EC 2.7.1.1 (hexokinase) inhibitor.

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].

storage

Desiccate at RT

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.]

578-66-5
3054-95-3
66-71-7
Synthesis of o-Phenanthroline from 8-Aminoquinoline and Acrolein diethyl acetal
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View Lastest Price from o-Phenanthroline manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
o-Phenanthroline pictures 2024-04-24 o-Phenanthroline
66-71-7
US $10.00 / kg 1kg 99.8% 10000ton Ouhuang Engineering Materials (Hubei) Co., Ltd
1,10-phenanthroline pictures 2024-02-23 1,10-phenanthroline
66-71-7
US $7.00-99.00 / g 25g 0.98 100kg Shanghai UCHEM Inc.
o-Phenanthroline pictures 2023-10-12 o-Phenanthroline
66-71-7
US $40.00-40.00 / kg 1kg 0.99 10 tons Hebei Yanxi Chemical Co., Ltd.
  • o-Phenanthroline pictures
  • o-Phenanthroline
    66-71-7
  • US $10.00 / kg
  • 99.8%
  • Ouhuang Engineering Materials (Hubei) Co., Ltd
1,10-Phenanthrolineo-Phenanthroline 1,10-Phenanthroline anhydrous(o-phenanthroline, phenantholine) 1,10-Phenanthroline,anhydrous,99% 1,10 PHENANTHROLINE BASE 3 8% Bathophenanthroline: (Use 1,10-o-Phenanthroline) O-PHENANTHROLINE 4,5-Diazaphenanthrene Activ-8 in hexylene glycol beta-Phenanthroline Solution forms containing 1,10-phenanthroline 1,10-Phenanthroline techn. anhydrous 1,10-Phenanthroline p.a. (anhydrous) 1,10-Phenanthroline, 99+% 25GR 1,10-Phenanthroline, 99+% 5GR 1,10-phenanthroline 98% Phenanthroling anhydrous 1,10-PHENANTHROLINE R. G., REAG. ACS, RE DOX INDICATOR 1,10-PHENANTHROLINE, 99+% 1,10-Phenanthroline Base, 38% 1,10-PhenanthrolineAnhydrous97%Min 1,10-Phenanthroline,97% AKOS 92891 1,10-Phenanthroline amhydrous 1,10-PHENANTHROLINE, ANHYDROUS1,10-PHENANTHROLINE, ANHYDROUS1,10-PHENANTHROLINE, ANHYDROUS 1,10-PhenanthroL 1,10-Phenanthroline, 99%, for synthesis 1,10-PHENANTHROLINE ANHYDROUS FOR SYNTHE o-Phenanthroline USP/EP/BP Solution forms containing 1.10-Phenanthroling anhydrous 1,10-Phenanthroline Anhydrous extrapure, 99%, water 2% JACS-66-71-7 phen ORTHOPHENANTHROLINE 4,5-Phenanthroline 1,10-Phenanthroline anhydrate 1,10-Fenanthrolin 1,10-o-Phenanthroline 10-Phenanthroline 1,10-PHENANTHROLINE 1,10-Phen 1,1-Phenanthroline 1,10-Phenanthroline (7CI, 8CI, 9CI, ACI) Anhydrous phenanthroline 66-71-7 C12H8N2 Building Blocks Heterocyclic Building Blocks N-Containing Others Industrial/Fine Chemicals Heterocyclic Building Blocks N-Containing Others Py-N Achiral Nitrogen organic amine Aromatics