1,10-Phenanthroline

HCID 1318CAS 66-71-7

Basic information

Standard SMILES
c1cnc2c(c1)ccc1cccnc12
InChIKey
DGEZNRSVGBDHLK-UHFFFAOYSA-N
Molecular formula
C12H8N2
Average molar mass
180.2 g/mol
Monoisotopic mass
180.06874826

Overview

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.

Names & identifiers

Preferred name
1,10-Phenanthroline
IUPAC
1,10-phenanthroline
English name
o-Phenanthroline
Molecular formula
C12H8N2
Molecular weight
180.21

Names & synonyms

1,10-phenanthroline66-71-7o-phenanthroline4,5-diazaphenanthreneorthophenanthroline1,10-o-phenanthrolinebeta-phenanthroline2-phenanthrolineDTXSID1025857O-PHEW4X6ZO7939NSC-4265
Show more names
1,10-Phen10-Phenanthroline1,10-Fenanthrolin1,10-Phenanthroline anhydrate4,5-Phenanthroline1,1-Phenanthroline
NSC-203545DTXCID405857CHEBI:44975(OP)2Cu(I)RefChem:410355200-629-2Phenanthrolinephen

Database identifiers

CAS
66-71-7
PubChem CID
1318
DTXSID
DTXSID1025857
ChEMBL
CHEMBL415879
ChEBI
CHEBI:44975
UNII
W4X6ZO7939
EC Number
200-629-2
Nikkaji
J4.844E

Properties

Computed structural properties

XLogP
1.8
Topological polar surface area
25.8 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
2
Rotatable bonds
0
Heavy atoms
14

Experimental & physicochemical properties

DrugsPharmaceuticals -> Listed in ZINC15
PolymersOther Classes -> Polycyclic Aromatic Hydrocarbons
SpringerMaterials PropertiesAngular frequency
LogP1.93
Solubility>27 [ug/mL] (The mean of the results at pH 7.4)
Boiling Point> 300 °C

Physicochemical properties

Melting point
114 · 114-117 °C(lit.)
Boiling point
330 °C · >330°C
Density
1.1836 · 1.1836 (rough estimate)
refractive index
1.52 · 1.5200 (estimate)
Flash point
330 °C · >330°C
storage temp.
30 °C · Store below +30°C.

Safety & regulation

GHS classification

GHS Classification · 6 items

Danger

H301: Toxic if swallowed [Danger Acute toxicity, oral]

P264, P270, P273, P301+P316, P321, P330, P391, P405, and P501 (click each P-code to see the statement)

Danger

H301 (99.8%): Toxic if swallowed [Danger Acute toxicity, oral]

P264, P270, P273, P301+P316, P321, P330, P391, P405, and P501 (click each P-code to see the statement)

Hazard information

Regulatory Information · 3 items

Chemical: 1,10-Phenanthroline

1,10-Phenanthroline is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 1,10-Phenanthroline are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

1,10-Phenanthroline: Does not have an individual approval but may be used under an appropriate group standard

Hazards SummaryCauses kidney changes in intraperitoneal lethal-dose studies of mice (LD50 = 75 mg/kg); [RTECS] May cause irritation; Toxic by ingestion; [Sigma-Aldrich MSDS] See 2,2'-Bipyridine. See POLYCYCLIC AROMATIC HYDROCARBONS.
Hazard Classes and Categories · 3 items

Acute Tox. 3 (99.8%)

Acute toxicity - category 3

Acute Tox. 3 *

Safety & protection

Protective Action Criteria (PAC) · 3 items

0.25 [mg/m3]

2.7 [mg/m3]

16 [mg/m3]

Toxicology

Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).

Safety data

PPE
Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
wgk
3
tsca
TSCA listed
rtecs
SF8437000
ridadr
UN 2811 6.1/PG 3
hs_code
29339990

Chemistry & industry

Pharmacology

MeSH Pharmacological Classification · 6 items

Chemicals that bind to and remove ions from solutions. Many chelating agents function through the formation of COORDINATION COMPLEXES with METALS.

Drugs that inhibit cholinesterases. The neurotransmitter ACETYLCHOLINE is rapidly hydrolyzed, and thereby inactivated, by cholinesterases. When cholinesterases are inhibited, the action of endogenously released acetylcholine at cholinergic synapses is potentiated. Cholinesterase inhibitors are widely used clinically for their potentiation of cholinergic inputs to the gastrointestinal tract and urinary bladder, the eye, and skeletal muscles; they are also used for their effects on the heart and the central nervous system.

Reagents with two reactive groups, usually at opposite ends of the molecule, that are capable of reacting with and thereby forming bridges between side chains of amino acids in proteins; the locations of naturally reactive areas within proteins can thereby be identified; may also be used for other macromolecules, like glycoproteins, nucleic acids, or other.

Agents that are capable of inserting themselves between the successive bases in DNA, thus kinking, uncoiling or otherwise deforming it and therefore preventing its proper functioning. They are used in the study of DNA.

Organic chemicals that form two or more coordination links with an iron ion. Once coordination has occurred, the complex formed is called a chelate. The iron-binding porphyrin group of hemoglobin is an example of a metal chelate found in biological systems.

Compounds which inhibit or antagonize biosynthesis or actions of proteases (ENDOPEPTIDASES).

Uses & manufacturing

UsesUsed as an analytical reagent, metal chelator, and in organic synthesis; [Merck Index] Permitted for use as an inert ingredient in non-food pesticide products; [EPA]
U.S. Production2023: <50,000 lb
Industry UsesDrier
General Manufacturing Information · 2 items

Paint and Coating Manufacturing

1,10-Phenanthroline: ACTIVE

Applications · 3 items

Descriptiono-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.

UsesAs 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.

Useso-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 CH 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.

Preparation methods

Preparation1,10-Phenanthroline is prepared by heating o-phenylenediamine, glycerin, nitrobenzene and concentrated sulfuric acid.

Suppliers50 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
北京华美互利生物化工010-56205725 · [email protected]
衢州润东化工有限公司0570-8789886 18892685668 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
INTATRADE GmbH+49 3493/605464 · [email protected]

Additional notes

DefinitionChEBI: 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.

Related reactions

1,045 records

Linked notes

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