1,10-フェナントロリン

1,10-Phenanthroline

HCID 1318CAS 66-71-7

基本情報

標準SMILES
c1cnc2c(c1)ccc1cccnc12
InChIKey
DGEZNRSVGBDHLK-UHFFFAOYSA-N
分子式
C12H8N2
平均分子量
180.2 g/mol
単同位体質量
180.06874826

概要

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.

名称と識別子

優先名称
1,10-Phenanthroline
IUPAC
1,10-phenanthroline
現地名
1,10-フェナントロリン
英語名
o-Phenanthroline
分子式
C12H8N2
分子量
180.21

名称と別名

1,10-phenanthroline66-71-7o-phenanthroline4,5-diazaphenanthreneorthophenanthroline1,10-o-phenanthrolinebeta-phenanthroline2-phenanthrolineDTXSID1025857O-PHEW4X6ZO7939NSC-4265
名称をさらに表示
o-フェナントロリン4,5-ジアザフェナントレン1,10-フェナントロリンβ-フェナントロリン1,10-フェナントロリン一水和物(o-〃)1,10‐フェナントロリン1,10-フェナンスロリン1,10-Phen10-Phenanthroline1,10-Fenanthrolin1,10-Phenanthroline anhydrate4,5-Phenanthroline1,1-Phenanthroline
NSC-203545DTXCID405857CHEBI:44975(OP)2Cu(I)RefChem:410355200-629-2Phenanthrolinephen

データベース識別子

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

物性

構造計算による物性

XLogP
1.8
極性表面積
25.8 Ų
水素結合供与体数
0
水素結合受容体数
2
回転可能結合数
0
重原子数
14

実験および物理化学的性質

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

物理化学的性質

融点
114 · 114-117 °C(lit.)
沸点
330 °C · >330°C
比重(密度)
1.1836 · 1.1836 (rough estimate)
屈折率
1.52 · 1.5200 (estimate)
闪点
330 °C · >330°C
貯蔵温度
30 °C · Store below +30°C.

化学的性質

化学的特性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.

安全と法規制

GHS分類

GHS Classification · 6 件

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)

危険有害性情報

Regulatory Information · 3 件

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 件

Acute Tox. 3 (99.8%)

Acute toxicity - category 3

Acute Tox. 3 *

安全と保護具

Protective Action Criteria (PAC) · 3 件

0.25 [mg/m3]

2.7 [mg/m3]

16 [mg/m3]

毒性情報

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

安全データ

wgk
3
tsca
TSCA listed
rtecs
SF8437000
ridadr
UN 2811 6.1/PG 3
毒性
dni-hmn:leu 5 mg/L ONCOBS 46,193,89
hs_code
29339990

化学と産業

薬理情報

MeSH Pharmacological Classification · 6 件

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).

用途と製造

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 件

Paint and Coating Manufacturing

1,10-Phenanthroline: ACTIVE

応用分野 · 4 件

解説ピリジン環2個がベンゼン環と縮合したフェナントレン形の化合物.多くの金属イオンと安定なキレート化合物をつくるので,分析試薬として使われる.

用途塗料乾燥剤,メッキ薬,架橋ポリエチレン絶縁剤,重合触媒原料。

説明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.

使用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 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.

調製方法 · 2 件

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

純化方法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.]

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