485-47-2

Basic information

• Product Name: NINHYDRIN
• Synonyms: 1,2,3-Indantrione monohydrate, 2,2-Dihydroxy-1,3-indanedione, Trioxohydrindene monohydrate;Ninhydrin, Monohydrate, Reagent;Ninhydrin , (1,2,3-Indantrione monohydrate);Ninhydrin (Ethanol Solution) (contains Acetic Acid) [for TLC Stain];NINHYDRINANALYTICAL GRADE;Ninhydrin,1,2,3-Indantrione monohydrate, 2,2-Dihydroxy-1,3-indanedione, Trioxohydrindene monohydrate;Ninhydrin p.a.;Ninthydrin
• CAS NO: 485-47-2
• Molecular Formula: C₉H₆O₄
• Molecular Weight: 178.14
• EINECS: 207-618-1
• Product Categories: Building Blocks;C9;Carbonyl Compounds;Chemical Synthesis;Ketones;Organic Building Blocks;Analytical Chemistry;TLC Stains;Pyridines ,Halogenated Heterocycles
• Mol File: 485-47-2.mol

Chemical Properties

• Melting Point: 250 °C (dec.)(lit.)
• Boiling Point: 230.35°C (rough estimate)
• Flash Point: 13 °C
• Appearance: white to brownish-white, crystals/Powder/Solid
• Density: 0.862
• Vapor Density: 6.16 (vs air)
• Vapor Pressure: 9.83E-05mmHg at 25°C
• Refractive Index: 1.4209 (estimate)
• Storage Temp.: Store at RT.
• Solubility: ethanol: soluble100mg/mL
• PKA: 8.47±0.20(Predicted)
• Water Solubility: 0.1-0.5 g/100 mL at 20 ºC
• Sensitive: Light Sensitive
• Stability: Stable. Incompatible with amines, alkalies, strong bases. Light-sensitive.
• Merck: 14,6554
• BRN: 1910963
• CAS DataBase Reference: NINHYDRIN(CAS DataBase Reference)
• NIST Chemistry Reference: NINHYDRIN(485-47-2)
• EPA Substance Registry System: NINHYDRIN(485-47-2)

Safety Data

• Hazard Codes: Xn,T,F
• Statements: 22-36/37/38-39/23/24/25-20/21/22-11
• Safety Statements: 26-28A-45-16-36
• RIDADR: UN 1170 3/PG 2
• WGK Germany: 3
• RTECS: NK5425000
• F: 8
• TSCA: Yes
• HazardClass: 3
• PackingGroup: II
• Hazardous Substances Data: 485-47-2(Hazardous Substances Data)

Usage

Uses

1. Used in Forensic Science:
Ninhydrin hydrate is used as a fingerprint reagent for the development of latent fingermarks on porous surfaces. It has been used as a fingerprint reagent since the 1950s and as a cell stain since the early 1900s. Ninhydrin molecules form a complex with amino acids, resulting in a purple product known as Ruhmann's purple, which makes purple fingerprints easily visible on light-colored porous substrates.
2. Used in Chemical Analysis:
Ninhydrin hydrate is used as a reagent for the detection of free amino groups in amino acids, peptides, and proteins. It is particularly useful in identifying these groups in various chemical and biological applications.
3. Used in Sequence with Other Reagents:
Ninhydrin can be used in sequence with other reagents, such as indanedione and DFO, to develop latent prints on porous substrates. The recommended order of use is indanedione, DFO, and then ninhydrin. Using a reagent out of sequence may inhibit or limit the effectiveness of the other reagents.

History

Ninhydrin was discovered in 1910 by the German-English chemist Siegfried Ruhemann (1859–1943). In the same year, Ruhemann observed ninhydrin's reaction with amino acids. In 1954, Swedish investigators Oden and von Hofsten proposed that ninhydrin could be used to develop latent fingerprints.

Reactions

Ninhydrin reacts with primary and secondary amines (including amino acids, proteins, and peptides) to give a dark purple product known as Ruhemann's purple (RP) . As the eccrine component of a latent mark deposit contains amino acids, this reaction can be exploited as a means of developing fingermarks on porous surfaces such as paper and cardboard. The use of ninhydrin as a fingermark detection reagent was first proposed in 1954 by Odén and von Hofsten (1954). Since then, ninhydrin has become the most popular technique for fingermark detection on porous substrates. Eccrine glands secrete a range of different amino acids that may ultimately be present in a latent fingermark deposit (Hamilton 1965; Ramotowski 2001). Ninhydrin is a nonspecific amino acid reagent in that it reacts in the same manner with different amino acids. In this way, each amino acid present in the latent fingermark deposit will contribute to the developed fingermark image. Amino acids are stable compounds that, due to an affinity for cellulose, do not migrate to any significant extent through dry paper substrates. As a result, very old latent marks can be developed with ninhydrin (the development of 40-year-old marks has been recorded), and the revealed marks are normally of good quality. In addition, the amino acid composition of the eccrine secretion appears to remain relatively constant. Due to these qualities, the use of amino acid reagents (ninhydrin and ninhydrin analogs, including 1,8-diazafluoren-9-one [DFO]) constitutes an effective chemical technique for the development of latent fingermarks on paper surfaces.

Synthesis Reference(s)

Synthetic Communications, 24, p. 695, 1994 DOI: 10.1080/00397919408012648Tetrahedron Letters, 9, p. 6201, 1968

Air & Water Reactions

Slightly soluble in water.

Reactivity Profile

Ninhydrin hydrate is sensitive to prolonged exposure to light. Ninhydrin hydrate yields highly fluorescent ternary compounds with aldehydes and primary amines.

Hazard

Irritant.

Health Hazard

Symptoms of exposure to Ninhydrin hydrate may include skin irritation and sensitization, and redness of the skin. ?ACUTE/CHRONIC HAZARDS: This compound causes irritation on contact. When heated to decomposition it emits acrid smoke and fumes.

Fire Hazard

Flash point data for Ninhydrin hydrate are not available. Ninhydrin hydrate is probably combustible.

Synthesis

The synthesis of?Ninhydrin hydrate is as follows:A sealed-pressurised reaction vessel (5mL) equipped with a magnetic stirrer was charged with indan-1-one (1equiv), selenium dioxide (3.1equiv) and dioxane/water (3mL/0.3mL). It was then irradiated in a Biotage Initiator Microwave synthesizer 2.0 440W with microwave heating to 180°C with a maximum of 400W for 5min. Then, the vessel was rapidly forced-air cooled to room temperature. The mixture was transferred into a round bottom flask, and the vessel washed with acetone. Silica was added to prepare a solid deposit. The volatile solvents were then evaporated in vacuo before purification by flash chromatography (ethyl acetate/cyclohexane) to afford the corresponding ninhydrin.

Purification Methods

Crystallise ninhydrin from hot water (charcoal). Dry it under vacuum and store it in sealed brown containers. [Beilstein 7 IV 2786.]

InChI:InChI=1/C9H4O3.H2O/c10-7-5-3-1-2-4-6(5)8(11)9(7)12;/h1-4H;1H2

Synthetic route

1H-indene-1,3(2H)-dione (606-23-5) → indan-1,2,3-trione hydrate (485-47-2)

Conditions	Yield
With N-Bromosuccinimide; dimethyl sulfoxide Ambient temperature;	94%
With oxygen; Sensitox; tetrabutyl ammonium fluoride In chloroform for 3h; Irradiation;	75%
With polymer bound rose bengal; tetrabutyl ammonium fluoride; oxygen In chloroform at 0℃; for 3h; Irradiation;	75%
Multi-step reaction with 2 steps 1: alcohol 2: diluted sulfuric acid View Scheme

inden-1-one (83-33-0) → indan-1,2,3-trione hydrate (485-47-2)

Conditions	Yield
With N-Bromosuccinimide; dimethyl sulfoxide Ambient temperature;	85%
With selenium(IV) oxide; water In 1,4-dioxane at 180℃; for 0.0833333h; Temperature; Sealed tube; Microwave irradiation;	84%

2-indanone (615-13-4) → indan-1,2,3-trione hydrate (485-47-2)

Conditions	Yield
With N-Bromosuccinimide; dimethyl sulfoxide Ambient temperature;	82%

2,2-diethoxy-1H-indene-1,3(2H)-dione (20847-51-2) → indan-1,2,3-trione hydrate (485-47-2)

Conditions	Yield
With sulfuric acid In ethanol at 40℃; for 2h;	82%

2,2-dimethoxy-1,3-indanedione (65299-21-0) → indan-1,2,3-trione hydrate (485-47-2)

Conditions	Yield
With sulfuric acid In ethanol at 40℃; for 2h;	82%

phenyliodonium betaine of 1,3-indanedione (1283-97-2) → indan-1,2,3-trione hydrate (485-47-2)

Conditions	Yield
With water; nitric acid In chloroform at -5 - 0℃; for 0.166667h;	80%

C30H23NO7*BF4(1-)*H(1+) → indan-1,2,3-trione hydrate (485-47-2) + 2-hydroxy-2-(2-oxo-2-phenylethyl)-1H-indene-1,3(2H)-dione (70780-36-8)

Conditions	Yield
In water for 12h;	A n/a B 68%

β-bromoindenone (90271-93-5) → indan-1,2,3-trione hydrate (485-47-2)

Conditions	Yield
With bromine; dimethyl sulfoxide In benzene for 6h; Heating;	60%

1-methyl-4-nitrosobenzene (623-11-0) + isonaphthazarine (605-37-8) → indan-1,2,3-trione hydrate (485-47-2) + phthalonic acid (528-46-1) + benzene-1,2-dicarboxylic acid (88-99-3) + phthalide-3-carboxylic acid (708-14-5, 62283-01-6, 99266-05-4)

Conditions	Yield
Produkt 5:Hydrindantin;

2-nitro-1,3-indanedione (3674-33-7) → indan-1,2,3-trione hydrate (485-47-2)

Conditions	Yield
Erwaermen;

2-(4'-dimethylaminophenylimino)-1,3-indanedione (60130-82-7) → indan-1,2,3-trione hydrate (485-47-2)

Conditions	Yield
With sulfuric acid

2-iodo-2-nitro-indan-1,3-dione (872785-94-9) → indan-1,2,3-trione hydrate (485-47-2) + benzene-1,2-dicarboxylic acid (88-99-3)

Conditions	Yield
at 145 - 165℃; anschliessend Behandeln mit Wasser;

2-chloro-2-nitro-indan-1,3-dione (90415-25-1) + nitrobenzene (98-95-3) → indan-1,2,3-trione hydrate (485-47-2) + 2,2-dichloroindan-1,3-dione (32974-80-4)

2-bromo-2-nitro-indan-1,3-dione (40005-25-2) + nitrobenzene (98-95-3) → indan-1,2,3-trione hydrate (485-47-2) + 2,2-dibromo-indan-1,3-dione (1685-97-8)

indantrione (938-24-9) → indan-1,2,3-trione hydrate (485-47-2)

Conditions	Yield
With H2O In 1,4-dioxane; water at 25℃; Kinetics; Thermodynamic data; var. solvents ratios, var. temp., ΔH(excit.), ΔS(excit.), kinetic solvents isotope effect;
With water Yield given;

2,3-epoxy-2,3-dihydro-1,4-naphthoquinone (15448-58-5) + aqueous solution → indan-1,2,3-trione hydrate (485-47-2) + isonaphthazarine (605-37-8) + phthalonic acid (528-46-1) + 2,2'-dihydroxy.<2,2'>biindanyl-1,3,1',3'-tetraone

Conditions	Yield
Erhitzen bei pH 7,0 unter Durchleiten von Luft - Produkt 5: Verbindung C20H12O6;

selenium(IV) oxide (7446-08-4) + 1H-indene-1,3(2H)-dione (606-23-5) + aqueous dioxane → indan-1,2,3-trione hydrate (485-47-2)

1-oxo-2.3-bis-<4-dimethylamino-phenylimino>-hydrindene → indan-1,2,3-trione hydrate (485-47-2)

Conditions	Yield
With sulfuric acid

2-oxo-1.3-bis-<4-dimethylamino-phenylimino>-hydrindene(?) → indan-1,2,3-trione hydrate (485-47-2)

Conditions	Yield
With sulfuric acid

isonaphthazarine (605-37-8) + water (7732-18-5) → indan-1,2,3-trione hydrate (485-47-2) + phthalonic acid (528-46-1) + benzene-1,2-dicarboxylic acid (88-99-3) + phthalide-3-carboxylic acid (708-14-5, 62283-01-6, 99266-05-4)

Conditions	Yield
Produkt 5:Hydrindantin;

sulfuric acid (7664-93-9) + 2-(4'-dimethylaminophenylimino)-1,3-indanedione (60130-82-7) → indan-1,2,3-trione hydrate (485-47-2)

water (7732-18-5) + naphthalene-1,2,3,4-tetraone; dihydrate (34333-95-4) → indan-1,2,3-trione hydrate (485-47-2) + isonaphthazarine (605-37-8)

1,2,3,4-tetrahydro-1,4-dioxo-2,2,3,3-tetrahydroxynaphthalene (100343-43-9) → indan-1,2,3-trione hydrate (485-47-2)

Conditions	Yield
In water for 1h; Heating;

1-methyl-pyrrolidin-2-one (872-50-4) + TOYO-Pearl resin + benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate (128625-52-5) → indan-1,2,3-trione hydrate (485-47-2)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dichloromethane

TOYO-Pearl resin + succinylsulfathiazole (116-43-8) → indan-1,2,3-trione hydrate (485-47-2)

Conditions	Yield
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane; N,N-dimethyl-formamide

1H-indene-1,3(2H)-dione (606-23-5) + thionaphthenequinon-anil-(2) → indan-1,2,3-trione hydrate (485-47-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: 80 percent / CHCl3; ethanol; diethyl ether / 0.08 h / 7 - 12 °C 2: 80 percent / nitric acid, water / CHCl3 / 0.17 h / -5 - 0 °C View Scheme

1H-indene-1,3(2H)-dione (606-23-5) + 2-aminomethylene-indandione-(1.3) → indan-1,2,3-trione hydrate (485-47-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: 44 percent / iodobenzene diacetate, H2SO4 / 2 h / Ambient temperature 2: 82 percent / conc. H2SO4 / ethanol / 2 h / 40 °C View Scheme
Multi-step reaction with 2 steps 1: 49 percent / iodobenzene diacetate, H2SO4 / 2 h / Ambient temperature 2: 82 percent / aq. H2SO4 / ethanol / 2 h / 40 °C View Scheme
Multi-step reaction with 2 steps 1: 49 percent / iodobenzene diacetate, H2SO4, ethanol / 2 h / Ambient temperature 2: 82 percent / aq. H2SO4 / ethanol / 2 h / 40 °C View Scheme

indan-1,2,3-trione hydrate (485-47-2) + dimedone (126-81-8) → 2-hydroxy-2-(4,4-dimethyl-2,6-dioxocyclohexane-1-yl)-1H-indene-1,3(2H)-dione (30511-21-8)

Conditions	Yield
at 20℃; for 1h;	100%
In water for 0.0166667h; Heating;	90%
With acetic acid at 20℃; for 0.5h;	62%

2,3-Dimethylphenol (526-75-0) + indan-1,2,3-trione hydrate (485-47-2) → 2-Hydroxy-2-(2-hydroxy-3,4-dimethyl-phenyl)-indan-1,3-dione (71321-28-3)

Conditions	Yield
In acetic acid for 1h; Heating;	100%

indan-1,2,3-trione hydrate (485-47-2) + thiourea (17356-08-0) → 1,3,3a,8a-tetrahydro-3a,8a-hydroxy-2-thioindeno<1,2-d>imidazole-2,8-dione

Conditions	Yield
at 20℃; for 0.75h;	100%
With acetic acid for 0.25h; Heating;	100%
In water at 20℃; for 0.75h; Green chemistry;	98%
In water at 80℃; for 1h;	91%
With acetic acid for 0.25h; Heating;

indan-1,2,3-trione hydrate (485-47-2) + 2,4-Xylenol (105-67-9) → 2-Hydroxy-2-(2-hydroxy-3,5-dimethyl-phenyl)-indan-1,3-dione (71321-32-9)

Conditions	Yield
In acetic acid for 0.5h; Heating;	100%

indan-1,2,3-trione hydrate (485-47-2) + allyl-trimethyl-silane (762-72-1) → 2,2-bis(trimethylsilyloxy)-1,3-indandione (95920-26-6)

Conditions	Yield
trimethylsilyl trifluoromethanesulfonate In acetonitrile for 1h; Ambient temperature;	100%

indan-1,2,3-trione hydrate (485-47-2) + 3-methyl-1,2-benzenediamine (2687-25-4) → 11H-6-methylindeno<1,2-b>quinoxalin-11-one (154457-99-5)

Conditions	Yield
for 1h;	100%
In ethanol for 2h; Reflux;	85%
In ethanol for 0.0833333h;	75%

N,N'-Dimethylurea (96-31-1) + indan-1,2,3-trione hydrate (485-47-2) → 3a,8a-dihydroxy-1,3-dimethyl-1,3,3a,8a-tetrahydroindeno[1,2-d]imidazole-2,8-dione (22431-02-3)

Conditions	Yield
at 20℃; for 2h;	100%
In water at 50 - 60℃;	82%

indan-1,2,3-trione hydrate (485-47-2) + 4,5-dimethyl-1,2-phenylenediamine (3171-45-7) → 11H-7,8-dimethylindeno[1,2-b]quinoxaline-11-one (40114-83-8)

Conditions	Yield
for 1h;	100%
With bismuth(lll) trifluoromethanesulfonate In water at 20℃; for 0.1h;	91%
With acetic acid In ethanol at 20℃; for 2h;	82%

indan-1,2,3-trione hydrate (485-47-2) + N,N-dimethylthiourea (534-13-4) → 3a,8a-dihydroxy-1,3-dimethyl-2-thioxo-2,3,3a,8a-tetrahydro-1H-indeno[1,2-d]imidazole-8-one

Conditions	Yield
at 20℃; for 2h;	100%

indan-1,2,3-trione hydrate (485-47-2) + urea (57-13-6) → 3a,8a-dihydroxy-1,3,3a,8a-tetrahydroindeno[1,2-d]imidazole-2,8-dione (22431-00-1)

Conditions	Yield
at 80℃; for 1h;	100%
In water at 20℃; for 0.833333h; Green chemistry;	98%
In water at 50 - 60℃;	93%

indan-1,2,3-trione hydrate (485-47-2) + N,N-diphenylthiourea (102-08-9) → 3a,8a-dihydroxy-1,3-diphenyl-2-thioxo-2,3,3a,8a-tetrahydro-1H-indeno[1,2-d]imidazole-8-one

Conditions	Yield
at 60℃; for 1h;	100%
In acetic acid for 0.25h; Heating;	100%
In water at 20℃; for 0.75h; Green chemistry;	95%
In water at 50 - 60℃;	52%

indan-1,2,3-trione hydrate (485-47-2) + bis(diphenyl)urea (102-07-8) → 3a,8a-dihydroxy-1,3-diphenyl-1,3,3a,8a-tetrahydro-indeno[1,2-d]imidazole-2,8-dione (58137-72-7)

Conditions	Yield
In acetic acid for 0.25h; Heating;	100%
In water at 50 - 60℃;	64%
In benzene Reflux; regioselective reaction;

Cyanoacetohydrazide (140-87-4) + indan-1,2,3-trione hydrate (485-47-2) → 2-cyano-N'-(1,3-dioxo-1H-inden-2(3H)-ylidene)acetohydrazide

Conditions	Yield
at 20℃; for 1h;	100%
In 1,4-dioxane for 3h; Reflux;	84.94%

4-amino-2,3-dimethyl-1-phenylpyrazolin-5-one (83-07-8) + indan-1,2,3-trione hydrate (485-47-2) → 2-(2,3-dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazol-4-ylimino)-2H-indene-1,3-dione

Conditions	Yield
at 20℃; for 1h;	100%

indan-1,2,3-trione hydrate (485-47-2) + 1,3-cylohexanedione (504-02-9) → 4b,9b-dihydroxy-7,8-dihydro-4bH-indeno[1,2-b]benzofuran-9,10(6H,9bH)-dione (374918-82-8)

Conditions	Yield
With acetic acid for 0.25h; Heating;	100%

indan-1,2,3-trione hydrate (485-47-2) + acetic anhydride (108-24-7) → 2-chloro-1,3-dioxo-2,3-dihydro-1H-inden-2-yl acetate (20847-53-4)

Conditions	Yield
With hydrogenchloride In water	100%
With hydrogenchloride	100%

indan-1,2,3-trione hydrate (485-47-2) + 5-isopropyl-3-isopropylaminocyclohex-2-enone → 4b,9b-dihydroxy-5,7-diisopropyl-4b,5,6,7,8,9b-hexahydroindeno[1,2-b]indole-9,10-dione

Conditions	Yield
In methanol at 20℃; for 22h;	100%
In methanol at 20℃;
In methanol at 20℃; for 22h;

indan-1,2,3-trione hydrate (485-47-2) + 5-furan-2-yl-3-isopropylaminocyclohex-2-enone → 7-furan-2-yl-4b,9b-dihydroxy-5-isopropyl-4b,5,6,7,8,9b-hexahydroindeno[1,2-b]indole-9,10-dione

Conditions	Yield
In methanol at 20℃; for 22h;	100%
In methanol at 20℃;

indan-1,2,3-trione hydrate (485-47-2) + 3-isopropylamino-5-phenylcyclohex-2-enone → 4b,9b-dihydroxy-5-isopropyl-7-phenyl-4b,5,6,7,8,9b-hexahydroindeno[1,2-b]indole-9,10-dione

Conditions	Yield
In methanol at 20℃; for 22h;	100%
In methanol at 20℃;

indan-1,2,3-trione hydrate (485-47-2) + 1,2-diamino-benzene (95-54-5) → 11H-Indeno[1,2-b]quinoxaline-11-one (6954-91-2)

Conditions	Yield
at -5℃; for 0.25h;	99%
In water at 30℃; for 0.0138889h; Solvent; Irradiation; Sonication; Green chemistry;	98%
With acetic acid In ethanol for 3h; Reflux;	95%

indan-1,2,3-trione hydrate (485-47-2) → indantrione (938-24-9)

Conditions	Yield
With pyridine; chloro-trimethyl-silane In tetrachloromethane for 3h; Ambient temperature;	99%
In chlorobenzene for 0.5h; Heating;	99%
at 120℃;	93%

indan-1,2,3-trione hydrate (485-47-2) + 4-methyl-1,2-diaminobenzene (496-72-0) → 7-methyl-11H-indeno[1,2-b]quinoxalin-11-one

Conditions	Yield
In water at 30℃; for 0.00972222h; Irradiation; Sonication; Green chemistry;	99%
With bismuth(lll) trifluoromethanesulfonate In water at 20℃; for 0.1h;	91%
In ethanol for 2h; Heating;

indan-1,2,3-trione hydrate (485-47-2) + L-proline (147-85-3) → 1-oxo-2-(1-pyrrolin-1-ylium)-1H-indene-3-olat (15365-97-6, 109159-92-4)

Conditions	Yield
for 1h;	99%
In methanol at 25℃;	96%
With sodium acetate; acetic acid In water at 79.9℃; Rate constant; Mechanism; Thermodynamic data; E, ΔS, ΔH, var. ninhydrin concentration, var. pH;

indan-1,2,3-trione hydrate (485-47-2) + 2-aminobenzenethiol hydrochloride (3292-42-0) → 10a-Hydroxybenzo[e]indeno[2,1-b][1,4]thiazin-11(10aH)-one (60117-55-7)

Conditions	Yield
for 1h;	99%

indan-1,2,3-trione hydrate (485-47-2) + methyl 3-aminocrotonate (21731-17-9) → 3a,8a-dihydroxy-2-methyl-8-oxo-3,3a,8,8a-tetrahydro-3-aza-cyclopenta[a]indene-1-carboxylic methyl ester

Conditions	Yield
for 1h;	99%

indan-1,2,3-trione hydrate (485-47-2) + 3-(p-tolylamino)-5,5-dimethylcyclohex-2-enone (36646-78-3) → 7,7-dimethyl-5-[(4-methylphenyl)]-dihydroxy-4b,5,6,7,8,9b-hexahydroindeno [1,2-b]indole-9,10-dione

Conditions	Yield
In chloroform at 20℃; for 24h;	99%

indan-1,2,3-trione hydrate (485-47-2) → 2,3-dihydro-1H-indene-1,2,3-triol (5930-39-2)

Conditions	Yield
With formic acid; C18H24ClIrN3 In water at 80℃; for 4h; Schlenk technique; Inert atmosphere;	99%

5-chloro-2-methylindole (1075-35-0) + indan-1,2,3-trione hydrate (485-47-2) → 2-(5-Chloro-2-methyl-1H-indol-3-yl)-2-hydroxy-indan-1,3-dione (124312-85-2)

Conditions	Yield
In diethyl ether; water	98%

5-methoxylindole (1006-94-6) + indan-1,2,3-trione hydrate (485-47-2) → 2-hydroxy-2-(5-methoxy-1H-indol-3-yl)-1H-indene-1,3(2H)-dione (124312-84-1)

Conditions	Yield
In diethyl ether; water	98%
With acetic acid at 20℃; for 2h;	92%

indan-1,2,3-trione hydrate (485-47-2) + 3,5-Dimethoxyaniline (10272-07-8) → 5,5a,10,10a-Tetrahydro-5a,10a-dihydroxy-4-(2-hydroxy-1,3-dioxoindanyl)-1,3-dimethoxyindeno<1,2-b>indol-10-one

Conditions	Yield
In acetic acid for 16h; Ambient temperature;	98%

Upstream product

• 623-11-0 1-methyl-4-nitrosobenzene 
• 605-37-8 isonaphthazarine 
• 3674-33-7 2-nitro-1,3-indanedione 
• 60130-82-7 2-(4'-dimethylaminophenylimino)-1,3-indanedione 
• 872785-94-9 2-iodo-2-nitro-indan-1,3-dione 
• 90415-25-1 2-chloro-2-nitro-indan-1,3-dione 
• 98-95-3 nitrobenzene 
• 40005-25-2 2-bromo-2-nitro-indan-1,3-dione 
• 606-23-5 1H-indene-1,3(2H)-dione 
• 1283-97-2 phenyliodonium betaine of 1,3-indanedione 
• 938-24-9 indantrione 
• 90271-93-5 3-bromo-1H-inden-1-one 
• 83-33-0 inden-1-one 
• 615-13-4 2-indanone 

Downstream Products

• 103327-16-8 2-[2-(4-benzoyl-3,5-dimethyl-pyrrol-2-ylidene)-1-hydroxy-3-oxo-indan-1-yloxy]-2-hydroxy-indane-1,3-dione 
• 75-07-0 acetaldehyde 
• 5103-42-4 hydrindantin 
• 296800-92-5 2-(8-oxo-1⁽³⁾,8-dihydro-indeno[1,2-d]imidazole-2-carbonyl)-benzoic acid 
• 30511-21-8 2-hydroxy-2-(4,4-dimethyl-2,6-dioxocyclohexane-1-yl)-1H-indene-1,3(2H)-dione 
• 67-64-1 acetone 
• 6583-74-0 1,3-diphenylcyclopenta[a]indene-2,8-dione 
• 60117-49-9 2-hydroxy-2-(1H-indol-3-yl)-1H-indene-1,3(2H)-dione 
• 104680-74-2 1',2,3,3'α,3a'β,4',6',6a'β-octahydro-3'-(4-methoxyphenyl)-5'-methylspiropyrrole>-1,3,4',6'-tetraone 
• 104680-74-2 1',2,3,3'α,3a'α,4',6',6a'α-octahydro-3'-(4-methoxyphenyl)-5'-methylspiropyrrole>-1,3,4',6'-tetraone 
• 60117-50-2 2-hydroxy-2-(3-methyl-indol-2-yl)-indan-1,3-dione 
• 77510-26-0 3-(2-hydroxy-2-indane-1,3-dionyl)-2,5-dimethylindole 
• 71917-42-5 2-Hydroxy-2-(2-hydroxy-4-methoxy-phenyl)-indan-1,3-dione 
• 71917-43-6 2-Hydroxy-2-(2-hydroxy-5-methoxy-phenyl)-indan-1,3-dione 

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Chemistry of Free Cyclic Vicinal Tricarbonyl Compounds ('1,2,3-Triones'). Part 3. Polar and Redox Reactions of 1,2,3-Triones with Enamines of Different Types - News on Oxonol Dyes, Radicals, and Biradicals

The central C=O groups of cyclic 1,2,3-triones possess outstanding electrophilic (electron-pair-accepting) as well as oxidizing (one-electron-accepting) properties. Thus, 1,2,3-triones are chemically related to 1,2- and 1,4-benzoquinones. Whereas polar reactions with carbanion-like (electron rich) species give rise to nucleophilic addition reactions to C=O groups under exclusive C,C-bond formation, SET (single-electron transfer) or redox reactions effect a partial 'carbonyl Umpolung' via ketyl intermediates (C,C- and/or C,O-bond formation). Here, we report on numerous reactions between electron-rich, more- or less-polar enamines with 5,5-dimethylcyclohexane-1,2,3-trione (9a) and 1H-indene-1,2,3-trione (9b). Various new derivatives of basic oxonol dyes were formed, including the first oxonol dye incorporating a 1,3-dioxocyclohexyl moiety. A novel stable radical, 50/50′, was obtained from 9b and lla via addition, hydrolysis, and treatment with conc. H2SO4. Radical 50/50′ represents a vinylogous 'monodehydroreductone' and is, thus, related to monodehydroascorbic acid (143), to Russell's radical cation (144), to indigo (141/141′), and to quinhydrone.