イサチン

Isatin

HCID 7054CAS 91-56-5

基本情報

標準SMILES
O=C1Nc2ccccc2C1=O
InChIKey
JXDYKVIHCLTXOP-UHFFFAOYSA-N
分子式
C8H5NO2
平均分子量
147.13 g/mol
単同位体質量
147.0320284

名称と識別子

優先名称
Isatin
IUPAC
1H-indole-2,3-dione
現地名
イサチン
英語名
Isatin
分子式
C8H5NO2
分子量
147.13

名称と別名

Isatin91-56-51H-Indole-2,3-dioneINDOLE-2,3-DIONE2,3-Diketoindoline2,3-DioxoindolinePseudoisatinIsotinIsatic acid lactamIsatinic acid anhydrideo-Aminobenzoylformic anhydride2,3-Dioxo-2,3-dihydroindole
名称をさらに表示
イサチン2,3-インドリンジオン1H-インドール-2,3-ジオンインドリン-2,3-ジオンイサチン酸ラクタム2,3-ジケトインドリンイサチン酸無水物2,3-ジヒドロ-1H-インドール-2,3-ジオンインドール-2,3-ジオン2,3‐インドリンジオン2.3-インドリンジオンイサチン, 98%IsatinesatinlsatinISATIC ANHYDRIDE2,3-INDOLINEDIONE
2,3-dihydro-1H-indole-2,3-dioneDTXSID3038694CHEBI:27539NSC-926282X95S7M06DTXCID10186942,3 DioxoindolineRefChem:148910

データベース識別子

CAS
91-56-5
PubChem CID
7054
DTXSID
DTXSID3038694
ChEMBL
CHEMBL326294
ChEBI
CHEBI:27539
UNII
82X95S7M06
EC Number
202-077-8
Nikkaji
J4.342G、J608.794I

物性

構造計算による物性

XLogP
0.8
極性表面積
46.2 Ų
水素結合供与体数
1
水素結合受容体数
2
回転可能結合数
0
重原子数
11

実験および物理化学的性質

LogP · 2 件

0.83

0.830

Melting Point · 2 件

203

203.00 °C. @ 760.00 mm Hg

Vapor Pressure0.0000111 [mmHg]
Physical DescriptionOrange solid; [Merck Index] Orange odorless powder; [Alfa Aesar MSDS]
Kovats Retention Index1712;1712

物理化学的性質

融点
193 · 193-195 °C (dec.) (lit.)
沸点
267.22 °C · 267.22°C (rough estimate)
比重(密度)
1.3067 · 1.3067 (rough estimate)
蒸気圧
0 Pa · 0Pa at 25℃
屈折率
1.47 · 1.4700 (estimate)
闪点
220 °C · 220 °C

化学的性質

化学的特性orange-red powder or crystals

安全と法規制

GHS分類

GHS Classification · 6 件

This chemical does not meet GHS hazard criteria for 25.7% (44 of 171) of reports.

Warning

H317 (62.6%): May cause an allergic skin reaction [Warning Sensitization, Skin];H412 (60.8%): Harmful to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]

P261, P272, P273, P280, P302+P352, P321, P333+P317, P362+P364, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 171 reports by companies from 12 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.;Reported as not meeting GHS hazard criteria per 44 of 171 reports by companies.;There are 10 notifications provided by 127 of 171 reports by companies with hazard statement code(s).;Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.

危険有害性情報

Regulatory Information · 3 件

Chemical: 1H-Indole-2,3-dione

Status: Active Update: 02-09-2015 https://echa.europa.eu/registration-dossier/-/registered-dossier/15909

1H-Indole-2,3-dione: Does not have an individual approval but may be used under an appropriate group standard

Other Safety InformationIMAP assessments - 1H-Indole-2,3-dione: Human health tier II assessment
Hazards Summary · 1 件

Not a skin or eye irritant in rabbits; A very potent skin sensitizer in guinea pig maximization study; No evidence of contact allergy in Buehler study of guinea pigs (considered inconclusive due to orange/red staining at application sites); Delayed contact hypersensitivity observed in local lymph node assay (LLNA) studies of mice; Teratogenicity observed in the presence of maternal toxicity in rats; [EC: SCCP] Causes flaccid paralysis without anesthesia (usually neuromuscular blockage) and changes in motor activity in oral and intravenous lethal-dose studies of rats; Causes pigmented or nucleated red blood cells and changes in erythrocyte count in 6-week oral studies of rats; [RTECS] May cause eye irritation; Reproductive effects observed in experimental animals; [Alfa Aesar MSDS]

Hazard Classes and Categories · 2 件

Skin Sens. 1B (62.6%);Aquatic Chronic 3 (60.8%)

Skin sensitisation - category 1

毒性情報

Adverse EffectsSkin Sensitizer - An agent that can induce an allergic reaction in the skin.
Toxicity DataLC50 (rat) > 5,200 mg/m3/4hr

法規制情報

Regulatory Information · 3 件

Chemical: 1H-Indole-2,3-dione

Status: Active Update: 02-09-2015 https://echa.europa.eu/registration-dossier/-/registered-dossier/15909

1H-Indole-2,3-dione: Does not have an individual approval but may be used under an appropriate group standard

安全データ

wgk
1
tsca
TSCA listed
rtecs
NL7873000
ridadr
2811
hs_code
29337900
risk_code
36/37/38-20/21/22

化学と産業

用途と製造

Uses · 2 件

Used to make vat dyes and in analytical chemistry as a reagent for cuprous ions, mercaptans, thiophene, and indican; [Merck Index] Used in hair coloring products; [EC: SCCP]

Dressing Hair [Category: Other]

General Manufacturing Information1H-Indole-2,3-dione: ACTIVE
応用分野 · 3 件

解説イサチン,indoline-2,3-dione.C8H5NO2(147.13).1840年代にエルトマンO.L.ErdmannおよびローレントA.Laurentがインジゴの酸化によって初めて得た。構造はA.F.ケクレが69年に提出,78年にJ.F.W.A.vonバイヤーによって別途に合成されて確認された。インジゴやインドール類の酸化反応で生成する.ラクタム-ラクチム互変異性混合体.反応試薬によってラクタム形あるいはラクチム形として反応する.黄赤色の柱状晶.融点203.5 ℃.pKa 10.34±0.20.昇華性である.冷水に難溶,熱水に易溶,メタノール,エタノール,アセトン,ベンゼンに可溶,冷希アルカリに可溶(紫色).加熱により加水分解してイサチン酸を生じる.バット染料(建染(たてぞ)め染料)の中間体、銀および銅の検出試薬としての用途をもつ。

用途銀及び銅イオンの検出用。内因性MAO阻害物質研究用。染料原料。

使用Isatin is an endogenous monoamine oxidize (MAO) inhibitor involved in stress and anxiety. Additionally, isatin inhibits alkaline phosphatase (ALP), nitric oxide (NO)-stimulated soluble guanylate cyclase, and other enzymes. Isatins undergo a one-pot Wolff-Kishner like reduction with hydrazine hydrate, under surprisingly mild conditions, to give the corresponding oxindoles. It is used as chromatographic spray reagent for amino acid detection.

調製方法

純化方法Crystallise isatin from amyl alcohol and sublime it at 180o/1mm. In aqueous NaOH the ring opens to yield sodium o-aminobenzoylformate. [Beilstein 21 II 327, 567, 21 III/IV 4981, 21/10 V 221.]

サプライヤー50 社

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補足説明

定義ChEBI: An indoledione that is the 2,3-diketo derivative of indole.

関連反応

445 件

関連ノート

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