Isatin

HCID 7054CAS 91-56-5
Substructure searchFind similar structures

Basic information

Standard SMILES
O=C1Nc2ccccc2C1=O
InChIKey
JXDYKVIHCLTXOP-UHFFFAOYSA-N
Molecular formula
C8H5NO2
Average molar mass
147.13 g/mol
Monoisotopic mass
147.0320284

Names & identifiers

Preferred name
Isatin
IUPAC
1H-indole-2,3-dione
English name
Isatin
Molecular formula
C8H5NO2
Molecular weight
147.13

Names & synonyms

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
Show more names
IsatinesatinlsatinISATIC ANHYDRIDE2,3-INDOLINEDIONE
2,3-dihydro-1H-indole-2,3-dioneDTXSID3038694CHEBI:27539NSC-926282X95S7M06DTXCID10186942,3 DioxoindolineRefChem:148910

Database identifiers

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

Properties

Computed structural properties

XLogP
0.8
Topological polar surface area
46.2 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
2
Rotatable bonds
0
Heavy atoms
11

Experimental & physicochemical properties

LogP · 2 items

0.83

0.830

Melting Point · 2 items

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

Physicochemical properties

Melting point
193 · 193-195 °C (dec.) (lit.)
Boiling point
267.22 °C · 267.22°C (rough estimate)
Density
1.3067 · 1.3067 (rough estimate)
bulk density
600 kg/m3 · 600kg/m3
vapor pressure
0 Pa · 0Pa at 25℃
refractive index
1.47 · 1.4700 (estimate)

Safety & regulation

GHS classification

GHS Classification · 6 items

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.

Hazard information

Regulatory Information · 3 items

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 item

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 items

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

Skin sensitisation - category 1

Toxicology

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

Regulatory information

Regulatory Information · 3 items

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

Safety data

PPE
dust mask type N95 (US), Eyeshields, Gloves
wgk
1
tsca
TSCA listed
rtecs
NL7873000
ridadr
2811
hs_code
29337900

Chemistry & industry

Uses & manufacturing

Uses · 2 items

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
Applications · 4 items

Uses(1) The product is used as medicine and dye intermediates ,and it is used for the production of drug quinophan, dye disperse Yellow E-3G ; in chemical analysis,it is used as reagents for the determination of copper ions, mercaptans, thiophene, indoxyl-beta-glucoside. (2) Isatin as a reference material for the preparation of indigo and Maya blue; for the preparation of phthalazinone derivatives, spirooxindole derivatives, the expression of P-glycoprotein for multi-drug resistant cells; The ketone is fused to form indole-2-one as a tubercular mycobacterial protein tyrosine phosphatase B, a potent selective inhibitor, as a powerful antimicrobial and antifungal triazole-isatine complex, And the Knoevenagel enrichment reaction; the isatin is activated by the direct sp2/sp3C-H bond, and undergoes a reaction with the cyclopentadienyl-Pd (II) catalyzes the CH addition reaction to form 3-substituted-3-hydroxy 2-oxindole.

UsesIsatin 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.

UsesIsatin can be used as a reactant to prepare:Phthalazinone derivatives.Spirooxindole derivatives.Agents against multidrug-resistant cells expressing P-glycoprotein.Thiazolidinones spiro-fused to indolin-2-ones as potent and selective inhibitors of Mycobacterium tuberculosis protein tyrosine phosphatase B.Triazole-isatine compounds as potential antibacterial and antifungal agents.Biologically relevant scaffolds such as spiro[indole-thiazolidinones].It can be a reactant for:Cascade reactions with heterocyclic ketene aminals.Knoevenagel condensation reactions.Isatin can also be used as a chromatographic spray reagent for amino acids, and also as a reference material in the preparation of indigo and Maya Blue. It is responsible for the yellow color exhibited by the "Maya Yellow" pigment.

Usesmanufacture of vat dyes. In analytical chemistry as a reagent for cuprous ions, mercaptans, thiophene, and indican.

Upstream & downstream products

Upstream raw materials

Suppliers50 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
衢州润东化工有限公司0570-8789886 18892685668 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
上海如吉生物科技发展有限公司+86-21-65211385-8001 36031160 · [email protected]

Additional notes

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

Related reactions

445 records
New reaction record

Linked notes

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