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
Show more names
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
- Formal charge
- 0
- Complexity
- 182
Experimental & physicochemical properties
Physical Description
Liquid
White solid; [Merck Index] Hygroscopic solid; [Sigma-Aldrich MSDS]
Ionization Efficiency
Positive
3.25
2.7
Agilent XCT
Electrospray ionization
formic acid (5.3nM)
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.
- solubility
- 2.69 g/l · 2.69g/l
- pka
- 4.84 · 4.84(at 25℃)
- form
- Powder
- color
- White to light yellow or light pink
- Water Solubility
- slightly soluble
- Sensitive
- Hygroscopic
- Merck
- 14 · 14,7214
- BRN
- 126461 · 126461
- Henry's Law Constant
- 1.1 · 1.1×105 mol/(m3Pa) at 25℃, Zhang et al. (2010)
- Stability
- Stable. Hygroscopic. Store under nitrogen. Incompatible with strong acids, strong oxidizing agents.
- InChI
- 1S/C12H8N2/c1-3-9-5-6-10-4-2-8-14-12(10)11(9)13-7-1/h1-8H
- InChIKey
- DGEZNRSVGBDHLK-UHFFFAOYSA-N
- SMILES
- c1cnc2c(c1)ccc3cccnc23
- CAS DataBase Reference
- 66 · 66-71-7(CAS DataBase Reference)
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 4 X6ZO7939 · W4X6ZO7939
- NIST Chemistry Reference
- o-Phenanthroline(66-71-7)
- EPA Substance Registry System
- 1 · 1,10-Phenanthroline (66-71-7)
- UNSPSC Code
- 12352100 · 12352100
- NACRES
- 22 · NA.22
- Symbol(GHS)
- 6 · GHS06,GHS09
- Signal word
- Danger
- Hazard statements
- 301 · H301-H410
- Precautionary statements
- 264 · P264-P270-P273-P301+P310-P391-P405
- PPE
- 2 · Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
- Hazard Codes
- T,N
- Risk Statements
- 25 · 25-50/53
- Safety Statements
- 45 · 45-60-61
- RIDADR
- 2811 · UN 2811 6.1/PG 3
- WGK Germany
- 3 · 3
- RTECS
- 8437000 · SF8437000
- TSCA
- TSCA listed
- HazardClass
- 6.1 · 6.1
- PackingGroup
- III
- HS Code
- 29339990 · 29339990
- Storage Class
- 6.1 C · 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
- Hazard Classifications
- 3 OralAquatic · Acute Tox. 3 OralAquatic Acute 1Aquatic Chronic 1
- Toxicity
- 5 mg/L · dni-hmn:leu 5 mg/L ONCOBS 46,193,89
Safety & regulation
GHS classification
GHS Classification
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
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
Hazard Classes and Categories
Acute Tox. 3 (99.8%)
Acute toxicity - category 3
Acute Tox. 3 *
Safety & protection
Protective Action Criteria (PAC)
0.25 [mg/m3]
2.7 [mg/m3]
16 [mg/m3]
Toxicology
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
- Toxicity
- dni-hmn:leu 5 mg/L ONCOBS 46,193,89
- risk_code
- 25-50/53
- Signal word
- Danger
- Symbol(GHS)
- GHS06,GHS09
- hazard_code
- T,N
- safety_code
- 45-60-61
- hazard_class
- 6.1
- Storage Class
- 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
- packing_group
- III
- Hazard statements
- H301-H410
- Hazard Classifications
- Acute Tox. 3 OralAquatic Acute 1Aquatic Chronic 1
- Precautionary statements
- P264-P270-P273-P301+P310-P391-P405
Chemistry & industry
Pharmacology
MeSH Pharmacological Classification
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
General Manufacturing Information
Paint and Coating Manufacturing
1,10-Phenanthroline: ACTIVE
Applications
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.
Upstream & downstream products
Upstream raw materials
Downstream products
Suppliers50 total
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
Linked notes
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