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1,10-フェナントロリン

1,10-Phenanthroline

HCID 1318
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基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
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基本情報

CAS
66-71-7
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補完中

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
形式電荷
0
複雑度
182

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

Liquid

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

Ionization Efficiency · 6 件

Positive

3.25

2.7

Agilent XCT

Electrospray ionization

formic acid (5.3nM)

Dissociation Constants4.27 (at 20 °C)

安全と法規制

安全情報は参考情報です。供給元の安全データシート(SDS)、適用法令、専門家による評価に代わるものではありません。

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

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

関連反応

1,045 件
反応記録を作成
HRID 1300 の反応式
HRID 1300反応物としてuspto-grants-1998_03
HRID 1301 の反応式
HRID 1301触媒としてuspto-grants-1998_03
HRID 11745 の反応式
HRID 11745反応物としてuspto-grants-2006_08
HRID 32282 の反応式
HRID 32282反応物としてuspto-grants-2008_09
HRID 32728 の反応式
HRID 32728反応物としてuspto-grants-2008_09
HRID 33275 の反応式
HRID 33275反応物としてuspto-grants-2008_09
HRID 33907 の反応式
HRID 33907反応物としてuspto-grants-2008_09
HRID 41595 の反応式
HRID 41595反応物としてuspto-grants-2013_09
1 / 131 ページ

化合物ノート

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このページの内容基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
その他の操作
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Collision Cross Section
132.4 Ų [M+H]+ [CCS Type: DT; Buffer gas: N2; Ionization: ESI+; Dataset: TOXCAST; Source Identifier: DTXSID1025857]

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.
溶解性
2.69 g/リットル · 2.69g/リットル
酸解離定数(Pka)
4.84 · 4.84(at 25℃)
外見
粉
色
白色から淡い黄色または淡いピンク
水溶解度
わずかに溶ける
Merck
14 · 14,7214
BRN
126461 · 126461
Henry's Law Constant
1.1 · 1.1×105 mol/(m3Pa) at 25℃, Zhang et al. (2010)
安定性
安定。吸湿性。窒素下で保管してください。強酸、強酸化剤とは相容れない。
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 データベース
66 · 66-71-7(CAS DataBase Reference)
NISTの化学物質情報
o-Phenanthroline(66-71-7)
EPAの化学物質情報
1 · 1,10-Phenanthroline (66-71-7)

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.

Carcinogen Classification
No 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
risk_code
25-50/53
hazard_code
T,N
safety_code
45-60-61
hazard_class
6.1
packing_group
III
Hazard Classifications
Acute Tox. 3 OralAquatic Acute 1Aquatic Chronic 1
ストレージクラス
6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects

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.]

上流・下流製品情報

上流原料

8-アミノキノリン1,2-フェニレンジアミン1,10-Phenanthroline, 1,2,3,4-tetrahydro-Pyridine, 3,3'-(1Z)-1,2-ethenediylbis[2-bromo-2-アミノニコチンアルデヒド5,6-エポキシ-5,6-ジヒドロ-[1,10]フェナントロリンこはく酸ジナトリウム

下流製品

1,10-フェナントロリン-5,6-ジオン2,9-dibromo-1,10-phenanthroline-5,6-dioneアセチルアセトナトナトリウム1,10-Phenanthroline-5,6-dione,3,8-dibromo5,6-ジメチル-1,10-フェナントロリン2-メトキシベンジルアルコール2,2'-ビ[4-キノリンカルボン酸]2,9-ジクロロ-1,10-フェナントロリン