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1,10-Phenanthrolin

1,10-Phenanthroline

HCID 1318
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Grundinformationen

CAS
66-71-7
Standard-SMILES
c1cnc2c(c1)ccc1cccnc12
InChIKey
DGEZNRSVGBDHLK-UHFFFAOYSA-N
Summenformel
C12H8N2
Durchschnittliche Molmasse
180,2 g/mol
Monoisotopische Masse
180,06874826

Überblick

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.

Namen und Bezeichner

Bevorzugter Name
1,10-Phenanthroline
IUPAC
1,10-phenanthroline
Lokaler Name
1,10-Phenanthrolin
Englischer Name
o-Phenanthroline
Summenformel
C12H8N2
Molmasse
180.21

Namen und Synonyme

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

Datenbank-Bezeichner

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

Eigenschaften

Berechnete StruktureigenschaftenWird ergänzt

XLogP
1,8
Polarare Oberfläche (TPSA)
25,8 Ų
H-Brücken-Donoren
0
H-Brücken-Akzeptoren
2
Frei drehbare Bindungen
0
Schwere Atome
14
Formalladung
0
Komplexität
182

Experimentelle und physikochemische Eigenschaften

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
Melting Point117 °C
Vapor Pressure0.0000523 [mmHg]
Physical Description · 2 Einträge

Liquid

White solid; [Merck Index] Hygroscopic solid; [Sigma-Aldrich MSDS]

Ionization Efficiency · 6 Einträge

Positive

3.25

2.7

Agilent XCT

Sicherheit und Regulatorisches

Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.

GHS-Klassifizierung

GHS Classification · 6 Einträge

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)

Gefahrenhinweise

Regulatory Information · 3 Einträge

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 Einträge

Acute Tox. 3 (99.8%)

Acute toxicity - category 3

Acute Tox. 3 *

Sicherheit und Schutzausrüstung

Protective Action Criteria (PAC) · 3 Einträge

0.25 [mg/m3]

2.7 [mg/m3]

16 [mg/m3]

Chemie und Industrie

Pharmakologische Informationen

MeSH Pharmacological Classification · 6 Einträge

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).

Verwendung und Herstellung

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 Einträge

Zugehörige Reaktionen

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Electrospray ionization

formic acid (5.3nM)

Dissociation Constants4.27 (at 20 °C)
Collision Cross Section132.4 Ų [M+H]+ [CCS Type: DT; Buffer gas: N2; Ionization: ESI+; Dataset: TOXCAST; Source Identifier: DTXSID1025857]

Physikochemische Eigenschaften

Schmelzpunkt
114 · 114-117 °C(lit.)
Siedepunkt
330 °C · >330°C
Dichte
1.1836 · 1.1836 (rough estimate)
Brechungsindex
1.52 · 1.5200 (estimate)
Flammpunkt
330 °C · >330°C
storage temp.
30 °C · Store below +30°C.
Löslichkeit
2.69 g/l · 2.69g/l
pka
4.84 · 4.84(at 25℃)
Aggregatzustand
Powder
Farbe
White to light yellow or light pink
Wasserlöslichkeit
slightly soluble
Merck
14 · 14,7214
BRN
126461 · 126461
Henry's Law Constant
1.1 · 1.1×105 mol/(m3Pa) at 25℃, Zhang et al. (2010)
Stabilität
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 Datenbank
66 · 66-71-7(CAS DataBase Reference)
NIST chemische Informationen
o-Phenanthroline(66-71-7)
EPA chemische Informationen
1 · 1,10-Phenanthroline (66-71-7)

Toxikologische Informationen

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

Sicherheitsdaten

wgk
3
tsca
TSCA listed
ridadr
UN 2811 6.1/PG 3
hs_code
29339990
RTECS-Nr.
SF8437000
risk_code
25-50/53
Toxizität
dni-hmn:leu 5 mg/L ONCOBS 46,193,89
hazard_code
T,N
safety_code
45-60-61
hazard_class
6.1
packing_group
III
Speicherklasse
6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
Hazard Classifications
Acute Tox. 3 OralAquatic Acute 1Aquatic Chronic 1

Paint and Coating Manufacturing

1,10-Phenanthroline: ACTIVE

Anwendungen · 2 Einträge

Beschreibungo-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.

Verwendeno-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.

Darstellung

synthetische1,10-Phenanthroline is prepared by heating o-phenylenediamine, glycerin, nitrobenzene and concentrated sulfuric acid.

Vor- und nachgelagerte Produkte

Vorgelagerte Rohstoffe

8-Chinolylamino-Phenylendiamin1,10-Phenanthroline, 1,2,3,4-tetrahydro-Pyridine, 3,3'-(1Z)-1,2-ethenediylbis[2-bromo-2-Amino-3-pyridinecarboxaldehyde5 6-Epoxy-5 6-dihydro-(1 10)phenanthrol&Dinatriumsuccinat

Nachgelagerte Produkte

1 10-Phenanthroline-5 6-dione 972,9-dibromo-1,10-phenanthroline-5,6-dioneSodium 2,4-pentanedionate1,10-Phenanthroline-5,6-dione,3,8-dibromo5,6-Dimethyl-1,10-phenanthrolin2-Methoxybenzylalkohol[2,2'-Bichinolin]-4,4'-dicarbonsure2,9-Dichloro-1,10-phenanthroline