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
名称をさらに表示
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
- 形式電荷
- 0
- 複雑度
- 182
実験および物理化学的性質
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)
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.
安全と法規制
GHS分類
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)
危険有害性情報
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 *
安全と保護具
Protective Action Criteria (PAC)
0.25 [mg/m3]
2.7 [mg/m3]
16 [mg/m3]
毒性情報
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
化学と産業
薬理情報
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).
用途と製造
General Manufacturing Information
Paint and Coating Manufacturing
1,10-Phenanthroline: ACTIVE
応用分野
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
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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