PRODUCTS

ISATIN

Isatin is an important indole-based compound used in the preparation of numerous specialty chemicals and research intermediates.
Isatin's structure supports the synthesis of diverse substituted derivatives for pharmaceutical and material applications.
Isatin is also employed in laboratory studies involving heterocyclic chemistry, molecular design, and analytical research.

CAS Number: 91-56-5
EC Number: 202-077-8
Molecular Formula: C8H5NO2
Molecular Weight: 147.13

Synonyms: Isatin, 91-56-5, 1H-Indole-2,3-dione, INDOLE-2,3-DIONE, 2,3-Diketoindoline, 2,3-Dioxoindoline, Pseudoisatin, Isotin, Isatic acid lactam, Isatinic acid anhydride, o-Aminobenzoylformic anhydride, 2,3-Dioxo-2,3-dihydroindole, 2,3-dihydro-1H-indole-2,3-dione, DTXSID3038694, CHEBI:27539, NSC-9262, 82X95S7M06, DTXCID1018694, 2,3 Dioxoindoline, RefChem:148910, Indoline-2,3-dione, 2,3-Indolinedione, Isatine, Tribulin, 2,3-Ketoindoline, NSC 9262, MFCD00005718, UNII-82X95S7M06, 84788-92-1, 2,3-dihydroindole-2,3-dione, CHEMBL326294, 5-21-10-00221 (Beilstein Handbook Reference), AKOS000119125, AS-10908, 1H-benzo[d]azoline-2,3-dione, 1186480-61-4, EINECS 202-077-8, BRN 0383659, AI3-03111, 3-Indolinedione, indol-2, Indole-2, hydroxy-3-indolone, Isatin, p.a., 3-hydroxy-2-indolone, Isatin (Compound 1), Isatin, technical grade, 2H-indole-2,3-dione, ISATIN [MI], Isatin(NSC 9262), EC 202-077-8, WLN: T56 BMVVJ, A843979, SCHEMBL34016, MLS001066355, orb1221661, orb1300398, SCHEMBL1386281, SCHEMBL1501860, SCHEMBL1501879, SCHEMBL1809708, SCHEMBL7073534, SCHEMBL9027945, SCHEMBL28614049, SCHEMBL31087266, 2,3-Dihydro-indole-2,3-dione, BDBM11022, NSC9262, HMS2267D18, HMS3885P18, HMS5083G20, HMS6018N07, S00335a, HY-Y0265, 2,3-dihydro-1H-indol-2,3-dione, Tox21_202876, EBC-13637, s4717, SBB009100, STK387523, CCG-266182, CS-W020128, DB02095, FI02371, SB64041, CAS-91-56-5, NCGC00246983-01, NCGC00260422-01, AC-10666, SMR000471835, SY005277, DB-061345, I0080, I7302, NS00005535, ST50213409, T6862, EN300-17956, D70304, I-7801, F077309, Q421348, doi:10.14272/JXDYKVIHCLTXOP-UHFFFAOYSA-N.1, F9995-1662, Isatin, for spectrophotometric det. of proline and thiophene, >=99.0%, 2,3-Diketoindoline, 2,3-Dioxo-2,3-dihydroindole, 2,3-Dioxoindoline, 2,3-Indolinedione, 202-077-8, 2H-Indol-2-one, 3-hydroxy-, 3-hydroxy-2-oxoindole, 3-Hydroxy-2H-indol-2-on, 3-Hydroxy-2H-indol-2-one, 3-Hydroxy-2H-indol-2-one, 383659, 5-21-10-00221, 91-56-5, Indolequinone, indoline-2,3-dione, Isatic acid lactam, Isatin, Isatine, Isatinic acid anhydride, O-AMINOBENZOYLFORMIC ANHYDRIDE, 1186480-61-4, 1H-benzo[d]azoline-2,3-dione, 1H-Indole-2,3-dione, 1H-indole-2,3-dioneisatin, 2,3 Dioxoindoline, 2,3-Dihydro-1H-indole-2,3-dione, 2,3-Dihydroindole-2,3-dione, 2,3-dioxoindole, 2,3-Ketoindoline, 2043-61-0, 3-hydroxy-2-indolone, 5815-00-9, 84788-92-1, 98%, ACES_ELEEL, ACES_HUMAN, Acetylcholinesterase, Amine oxidase [flavin-containing] A, Amine oxidase [flavin-containing] B, AOFA_HUMAN, AOFB_BOVIN, AOFB_HUMAN, CHLE_HORSE, CHLE_HUMAN, Cholinesterase, Coagulation factor XII, EINECS 202-077-8, EST1_HUMAN, EST1_RABIT, FA12_HUMAN, hydroxy indolone, Indole-2,3-dione, Isatin;Indole-2,3-dione, isn, Isotin, Liver carboxylesterase 1, Pseudoisatin, Pseudoisatin, Indoline-2,3-dione, 2,3-Indolinedione, S00335a, SCMU_MYCTU, Secreted chorismate mutase, T56 BMVVJ, [WLN], Tribulin, 靛红

Isatin is an organic compound derived from indole with formula C8H5NO2.
Isatin was first obtained by Otto Linné Erdman and Auguste Laurent in 1840 as a product from the oxidation of indigo dye by nitric acid and chromic acids.

Isatin is a well-known natural product which can be found in plants of the genus Isatis, in Couroupita guianensis and also in humans, as a metabolic derivative of adrenaline.
Isatin looks like a red-orange powder, and it is usually employed as building block for the synthesis of a wide variety of biologically active compounds including antitumorals, antivirals, anti-HIVs and antituberculars.

The isatin core is also responsible for the color of "Maya blue" and "Maya yellow" dyes.
Studies in rats indicate that isatin modulates neurotransmitter activity, antagonizes atrial natriuretic peptide and inhibits monoamine oxidase.

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.
Isatin is used as chromatographic spray reagent for amino acid detection.

Isatin is an indoledione that is the 2,3-diketo derivative of indole.
Isatin has a role as an EC 1.4.3.4 (monoamine oxidase) inhibitor and a plant metabolite.

Isatin is an indole derivative first obtained by Erdman and Laurent in 1841 as an oxidation product of Indigo dye with nitric acid and chromic acids.
Isatin is found in many plants and Schiff bases of Isatin are have been investigated for pharmaceutical applications.

Isatin has been reported in Calanthe discolor, Capparis spinosa, and other organisms with data available.
Isatin's chemical name is indol(o)-2,3-dione, it is orange-red monoclinic prism crystal at room temperature.

Isatin is an indole-derived heterocyclic organic compound with the molecular formula C8H5NO2.
Isatin is an important intermediate in organic and medicinal chemistry, especially in the synthesis of pharmaceuticals, dyes, and biologically active compounds.
Isatin's reactive carbonyl groups make it useful in condensation reactions and the preparation of various substituted isatin derivatives.

Isatin is an indole derivative found in Isatis, Calanthe, and Couroupita that exhibits anti-inflammatory, antioxidative, neuromodulatory, and anticancer chemotherapeutic activities.
Isatin prevents TNBS-induced increases in TNF-α, COX-2, and PGE2 levels as well as decreases in SOD and GSH levels, protecting against colitis-induced injuries in animal models.

Isatin also inhibits monoamine oxidase B (MAO-B) and guanylate cyclase (natriuretic peptide receptors).
Schiff base derivatives of isatin inhibit the growth of various cancer cells and tumors, likely due to decreasing cyclin B1 and Cdc2 expression and inducing G2/M phase cell cycle arrest.

Derivatives of isatin also inhibit tubulin polymerization, Akt activation, and caspases 3, 7, and 9.
Isatin may also exhibit antiepileptic/anticonvulsant activity.

Applications of Isatin:
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.

Isatin 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].

Isatin 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.
Isatin is responsible for the yellow color exhibited by the "Maya Yellow" pigment.

Isatin undergoes Pd(II)-catalyzed C-H addition by direct sp2/sp3 C-H bond activation to form 3-substituted-3-hydroxy-2-oxindoles.
Isatin derivatives (bis-Schiff base) are synthesized by the condensation of the natural or synthetic isatins with hydrazine.

Uses of Isatin:
Isatin is widely used as an intermediate in the synthesis of pharmaceuticals, heterocyclic compounds, and biologically active molecules.
Isatin is employed in medicinal chemistry for preparing derivatives investigated for antimicrobial, anticancer, antiviral, and anti-inflammatory applications.

Isatin is also used in the manufacture of dyes, pigments, and color-forming compounds.
Isatin serves as a versatile reagent in condensation, cyclization, and functionalization reactions.
In addition, isatin is used in biochemical research, analytical chemistry, and the development of specialty organic materials.

Isatin is used to make vat dyes and in analytical chemistry as a reagent for cuprous ions, mercaptans, thiophene, and indican.
Isatin is used in hair coloring products.

Synthesis of Isatin:

Sandmeyer methodology:
The Sandmeyer methodology is the oldest and straightforward way for the synthesis of isatin.
The method involves the condensation between chloral hydrate and a primary arylamine (e.g. aniline), in the presence of hydroxylamine hydrochloride, in aqueous sodium sulfate to form an α‐isonitrosoacetanilide.
Isolation of this intermediate and subsequent electrophilic cyclization promoted by strong acids (e.g. sulfuric acid) furnishes isatin in >75% yield.

Stolle methodology:
The Stolle procedure is considered the best alternative to Sandmeyer methodology for the synthesis of both substituted and unsubstituted isatins.
In this case primary or secondary arylamines are condensed with oxalyl chloride to form a chlorooxalylanilide intermediate which can then cyclize in the presence of a Lewis acid (e.g. aluminium trichloride, titanium tetrachloride, boron trifluoride, etc.).

Other procedures:
More recent approaches to the synthesis of N-substituted isatins involves the direct oxidation of commercially available, substituted indoles or oxindoles with different oxidizing agents such as TBHP, IBX-SO3K, tBuONO etc.

Reactivity of Isatin:
The presence of an aromatic ring, a ketone and a γ-lactam moiety, gives to isatin the rare potential to be used as both an electrophile and a nucleophile: indeed, Isatin undergoes an enormous number of reactions, such as N-substitutions, electrophilic aromatic substitution at positions C-5 and C-7 of the phenyl ring, nucleophilic additions onto the C-3 carbonyl group, chemoselective reductions, oxidations, ring-expansions and spiro-annulations.
Because of this unique reactivity, isatin is considered one of the most valuable building blocks in organic synthesis.

N-Substitution:
The N-functionalization of the isatin core can be readily obtained by the deprotonation of the amino moiety, forming the corresponding sodium or potassium salt, and subsequent addition of an electrophile (e.g. alkyl or acyl halides).
On the other hand, N-arylation is usually achieved by cross-coupling reactions with aryl halides using copper or palladium catalysts.

Ring expansion:
In the field of organic synthesis, ring expansions are considered valuable reactions since they allow the obtainment medium-size ring (7-9 atoms) which are difficult to synthesize through "classical" methods.

To date, only few articles concerning the ring expansion of isatin derivatives has been reported.
The first one is an acid-catalyzed one-pot multicomponent reaction involving isatins, aminouracils, and isooxazolones to form isoxazoquinolines, important scaffolds in medicinal chemistry.

In another one-pot multicomponent reaction, a unique two-carbon expansion has been achieved by reacting isatin with indene-1,3-dione and N-substituted pyridinium bromide to form dibenzo[b,d]azepin-6-ones.

C-2/C-3 nucleophilic addition:
Isatin suffers nucleophilic addition on carbonyls at C-2 and C-3 positions.
The regioselectivity of the process strongly depends both on the substrate (properties of the substituents on the isatin core, especially those bonded to the nitrogen atom) and the reaction conditions (solvent, temperature etc.).
In some cases the nucleophilic addition could be followed by secondary reactions (e.g. cyclization, ring expansion, ring opening etc.)

Oxidation:
The oxidation of isatin using hydrogen peroxide (Baeyer–Villiger oxidation) or chromic anhydride yields isatoic anhydride, a compound widely used either in herbicide products and in medicinal chemistry.
The use of peroxydisulfuric acid gives rise to 1,4‑benzoxazine compounds.

Dimerization:
Dimerization of isatin with KBH4 in methanol yields Indirubin.
This represents the indigo pigment's red component and a highly effective cytotoxic compound.

Reduction:
Reduction of the non-amide carbonyl group occurs to give oxindole.

Stability and Reactivity of Isatin:

Chemical stability:
Stable under normal storage and handling conditions.

Conditions to avoid:
Avoid excessive heat, moisture, and incompatible materials.

Incompatible materials:
Strong oxidizing agents, strong acids, and strong bases.

Hazardous decomposition products:
Thermal decomposition may produce carbon oxides and nitrogen-containing fumes.

Handling and Storage of Isatin:

Safe handling:
Avoid dust formation and contact with skin and eyes.
Use adequate ventilation.

Storage conditions:
Store tightly closed in a cool, dry, well-ventilated place.

First Aid Measures of Isatin:

Inhalation:
Move to fresh air if dust is inhaled.

Skin contact:
Wash thoroughly with soap and water.

Eye contact:
Rinse cautiously with water for several minutes.

Ingestion:
Rinse mouth and seek medical advice if discomfort occurs.

Firefighting Measures of Isatin:

Suitable extinguishing media:
Use water spray, foam, dry chemical, or CO₂.

Protective equipment:
Firefighters should wear suitable protective equipment.

Accidental Release Measures of Isatin:

Personal precautions:
Avoid dust formation and ensure adequate ventilation.

Cleanup methods:
Collect carefully into a suitable closed container.

Exposure Controls / Personal Protective Equipment of Isatin:

Engineering controls:
Provide adequate ventilation.

Personal protection:
Wear protective gloves, safety glasses, and suitable protective clothing.
Use respiratory protection if dust is generated.

Identifiers of Isatin:
Article No.: 04211
Grade: AR
Purity: 98%: CAS No.: 91-56-5
Molecular Formula: C8H5NO2
Molecular Weight: 147.14
H.S. Code: 2933.7990

Cas No.: 91-56-5
Purity: ≥97%
Formula: C8H5NO2
Formula Wt.: 147.13
Chemical Name: Indole-2,3-dione
IUPAC Name: 1H-indole-2,3-dione
Synonym: 2,3-Indolinedione, 2,3-Diketoindoline
Melting Point: 203.5°C (partial subliminati°n)
Solubility: Soluble in boiling alcohol, ether, boiling water and alkali hydroxide.
Appearance: Red Powder

CAS No: 91-56-5
Chemical Name: Isatin
CBNumber: CB2447182
Molecular Formula: C8H5NO2
Molecular Weight: 147.13
MDL Number: MFCD00005718
MOL File: 91-56-5.mol

CAS: 91-56-5
IUPAC Name: 2,3-dihydro-1H-indole-2,3-dione
Molecular Formula: C8H5NO2
InChI Key: JXDYKVIHCLTXOP-UHFFFAOYSA-N
SMILES: O=C1NC2=CC=CC=C2C1=O
Molecular Weight (g/mol): 147.13

Product Number: I0080
Purity / Analysis Method : >98.0%(GC)(T)
Molecular Formula / Molecular Weight: C8H5NO2 = 147.13
Physical State (20 deg.C): Solid
Storage Temperature : Room Temperature (Recommended in a cool and dark place, <15°C)
CAS RN: 91-56-5
Reaxys Registry Number: 383659
PubChem Substance ID: 87571483
SDBS (AIST Spectral DB): 2597
Merck Index (14): 5104
MDL Number: MFCD00005718

CAS Number: 91-56-5
Beilstein Reference: 383659
ChEBI: CHEBI:27539
ChEMBL: ChEMBL326294
ChemSpider: 6787
DrugBank: DB02095
ECHA InfoCard: 100.001.889
EC Number: 202-077-8
Gmelin Reference: 165206
KEGG: C11129
PubChem CID: 7054
UNII: 82X95S7M06
CompTox Dashboard (EPA): DTXSID3038694
InChI: InChI=1S/C8H5NO2/c10-7-5-3-1-2-4-6(5)9-8(7)11/h1-4H,(H,9,10,11)
Key: JXDYKVIHCLTXOP-UHFFFAOYSA-N
InChI=1/C8H5NO2/c10-7-5-3-1-2-4-6(5)9-8(7)11/h1-4H,(H,9,10,11)
SMILES: O=C2c1ccccc1NC2=O

Empirical Formula (Hill Notation): C8H5NO2
CAS Number: 91-56-5
Molecular Weight: 147.13
UNSPSC Code: 12352100
NACRES: NA.22
PubChem Substance ID: 24847187
EC Number: 202-077-8
Beilstein/REAXYS Number: 383659
MDL number: MFCD00005718
Assay: 97%
Form: powder

Properties of Isatin:
Physical state at 20 °C: Solid
Colour: Orange powder
Melting point/ Freezing point [°C]: 193 - 195 °C
Flash point [°C]: 193° C
Solubility in water [% weight]: Insoluble in water

Melting point: 193-195 °C (dec.) (lit.)
Boiling point: 267.22°C (rough estimate)
Density: 1.3067 (rough estimate)
bulk density: 600kg/m3
vapor pressure: 0Pa at 25℃
refractive index: 1.4700 (estimate)
Flash point: 220 °C
storage temp.: Store below +30°C.
solubility: soluble
pka: 10.34±0.20(Predicted)
form: Powder
color: Orange
PH: 7 (1.9g/l, H2O, 20℃)
Water Solubility: Soluble in water (1.9 g/L at 20°C).
Decomposition: 194 ºC
Merck: 14,5104
BRN: 383659
Stability: Stable. Incompatible with strong acids.
Cosmetics Ingredients Functions: HAIR DYEING
InChI: 1S/C8H5NO2/c10-7-5-3-1-2-4-6(5)9-8(7)11/h1-4H,(H,9,10,11)
InChIKey: JXDYKVIHCLTXOP-UHFFFAOYSA-N
SMILES: O=C1Nc2ccccc2C1=O
LogP: 0.45
CAS DataBase Reference: 91-56-5(CAS DataBase Reference)
EWG's Food Scores: 1-3
FDA UNII: 82X95S7M06
NIST Chemistry Reference: Isatin(91-56-5)
EPA Substance Registry System: 1H-Indole-2,3-dione (91-56-5)
UNSPSC Code: 12352115
NACRES: NA.22

Chemical formula: C8H5NO2
Molar mass: 147.1308 g/mol
Appearance: Orange-red solid
Melting point: 200 °C (392 °F; 473 K)

Quality Segment: 100
assay: 97%
form: powder
mp: 193-195 °C (dec.) (lit.)
solubility: boiling water: soluble, diethyl ether: soluble, soluble
functional group: ketone
SMILES string: O=C1Nc2ccccc2C1=O
InChI: 1S/C8H5NO2/c10-7-5-3-1-2-4-6(5)9-8(7)11/h1-4H,(H,9,10,11)
InChI key: JXDYKVIHCLTXOP-UHFFFAOYSA-N

Molecular Weight: 147.13 g/mol
XLogP3: 0.8
Hydrogen Bond Donor Count: 1
Hydrogen Bond Acceptor Count: 2
Rotatable Bond Count: 0
Exact Mass: 147.032028402 Da
Monoisotopic Mass: 147.032028402 Da
Topological Polar Surface Area: 46.2 Å²
Heavy Atom Count: 11
Complexity: 212
Isotope Atom Count: 0
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Covalently-Bonded Unit Count: 1
Compound Is Canonicalized: Yes

Specifications of Isatin:
Appearance: Light yellow to Brown powder to crystal
Purity(GC): min. 98.0 %
Purity(Neutralization titration): min. 98.0 %
Melting point: 200.0 to 204.0 °C
NMR: confirm to structure

Water Content (Karl Fischer Titration): ≤1%
Appearance (Color): Orange
Form: Powder
Assay (HPLC): ≥97.5%
Identification (FTIR): Conforms

Names of Isatin:

Preferred IUPAC name:
1H-Indole-2,3-dione