608-08-2

Basic information

• Product Name: INDOXYL ACETATE
• Synonyms: 3-ACETOXYINDOLE;3-INDOLYL ACETATE;3-INDOXYL-3-ACETATE;3-INDOXYL ACETATE;ACETIC ACID 3-INDOLYL ESTER;3-Acetoxyindole~Indolyl acetate~Y-acetate;Indoxyl acetate 3-Indoxyl acetate;IndoxylAcetateA.R.
• CAS NO: 608-08-2
• Molecular Formula: C₁₀H₉NO₂
• Molecular Weight: 175.18
• EINECS: 210-154-2
• Product Categories: Indoles and derivatives;Indole Derivatives;Simple Indoles;Indoles;Intermediates;substrate
• Mol File: 608-08-2.mol
• Article Data: 6

Chemical Properties

• Melting Point: 128-130 °C(lit.)
• Boiling Point: 306.47°C (rough estimate)
• Flash Point: 158.9 °C
• Appearance: Colorless to lilac/Glistening Crystals
• Density: 1.1999 (rough estimate)
• Vapor Pressure: 9.41E-05mmHg at 25°C
• Refractive Index: 1.5060 (estimate)
• Storage Temp.: 2-8°C
• Solubility: DMSO (Slightly), Ethanol (Slightly), Methanol (Slightly)
• PKA: 15.89±0.30(Predicted)
• Water Solubility: Soluble in ethanol, water, chloroform, dichloromethane and methanol.
• BRN: 143086
• CAS DataBase Reference: INDOXYL ACETATE(CAS DataBase Reference)
• NIST Chemistry Reference: INDOXYL ACETATE(608-08-2)
• EPA Substance Registry System: INDOXYL ACETATE(608-08-2)

Safety Data

• Hazard Codes: Xn
• Statements: 22-36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• RTECS: AI3325000
• F: 8-10-21
• TSCA: Yes
• Hazardous Substances Data: 608-08-2(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 608-08-2 differently. You can refer to the following data:
1. Useful for detection of esterases3-Indoxyl acetate acts as a colorimetric substrate used for differentiating esterases from various microbiological species. Further, it is used as a plant growth-stimulating hormone and reagent. In addition to this, it acts as a useful synthetic intermediate.
2. INDOXYL ACETATE is a useful synthetic intermediate.

InChI:InChI=1/C10H9NO2/c1-7(12)13-10-6-11-9-5-3-2-4-8(9)10/h2-6,11H,1H3

Synthetic route

indole (120-72-9) + [bis(acetoxy)iodo]benzene (3240-34-4) → 3-indoxyl acetate (608-08-2)

Conditions	Yield
With potassium hydroxide In acetonitrile at 35℃; for 1.5h;	76%
With potassium hydroxide In toluene; acetonitrile at 20℃; for 1.5h; Green chemistry;

5-acetoxy-3-methoxycarbonyl-5H-1,2-benzodiazepine → 3-indoxyl acetate (608-08-2) + ethyl cyanoformate (623-49-4)

Conditions	Yield
In dichloromethane for 0.133333h; Irradiation;	A 74% B n/a

indole (120-72-9) + thallium(III) acetate (2570-63-0) → 3-indoxyl acetate (608-08-2)

Conditions	Yield
With acetic acid at 30℃; for 2h;	43%

3-Iodo-1H-indole (26340-47-6) + silver(I) acetate (563-63-3) → 3-indoxyl acetate (608-08-2)

Conditions	Yield
With acetic acid at 90℃; for 1h;	41%
With acetic acid

2-Acetyl-1H-indol-3-yl-acetat (100063-39-6) → 3-indoxyl acetate (608-08-2)

Conditions	Yield
With sodium hydroxide; water unter Stickstoff und Behandeln des Reaktionsprodukts mit Acetanhydrid bei 0grad;

phenylglycine-o-carboxylic acid (612-42-0) → 3-indoxyl acetate (608-08-2) + 1-acetyl-3-hydroxy-indole-2-carboxylic acid

Conditions	Yield
With potassium hydroxide at 260℃; Behandeln des mit CO2 und Essigsaeure teilweise neutralisierten Reaktionsgemisches mit Acetanhydrid;

indoxyl (480-93-3) + acetic anhydride (108-24-7) → 3-indoxyl acetate (608-08-2)

Conditions	Yield
With sulfuric acid; water
With alkali
With alkali

1-Nitrosoindol-3-yl acetate (140843-81-8) → 3-indoxyl acetate (608-08-2)

Conditions	Yield
In 1,4-dioxane; water at 25℃; Equilibrium constant;

3-methoxycarbonyl-5H-1,2-benzodiazepine (67790-18-5) → 3-indoxyl acetate (608-08-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: 68 percent / CH2Cl2 / 0 - 20 °C 2: 74 percent / CH2Cl2 / 0.13 h / Irradiation View Scheme

3-hydroxy-1H-indole-2-carboxylic acid (6245-93-8) → 3-indoxyl acetate (608-08-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: water / 70 - 80 °C 2: alkali View Scheme
Multi-step reaction with 2 steps 2: alkali View Scheme

indole (120-72-9) → 3-indoxyl acetate (608-08-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: methanol. NaOH-solution; iodine; potassium iodide 2: acetic acid View Scheme

3-indoxyl acetate (608-08-2) + N-Methyl-7-azaisatin → (2'Z)-7-aza-1-methylindirubin (1202876-71-8)

Conditions	Yield
Stage #1: 3-indoxyl acetate; N-Methyl-7-azaisatin In methanol at 25℃; Inert atmosphere; Stage #2: With sodium carbonate In methanol at 25℃; Inert atmosphere;	100%

5-fluoro-1H-indole-2,3-dione (443-69-6) + 3-indoxyl acetate (608-08-2) → 5-Fluoroindirubin (910035-37-9)

Conditions	Yield
With sodium carbonate In methanol at 20℃; for 3h;	95%
With sodium carbonate In methanol at 20℃;
With sodium carbonate

3-indoxyl acetate (608-08-2) + 5-Bromo-1H-indole-2,3-dione (87-48-9) → 5-Bromoindirubin (126433-41-8)

Conditions	Yield
With sodium carbonate In methanol at 20℃; for 3h;	95%
With sodium carbonate In methanol for 3.5h;	80%

3-indoxyl acetate (608-08-2) + 7-chloro-1-methylindoline-2,3-dione (63220-48-4) → 7-Chloro-1-methylindirubin (906660-40-0)

Conditions	Yield
With sodium carbonate In methanol	95%

5-fluoro-1H-indole-2,3-dione (443-69-6) + 3-indoxyl acetate (608-08-2) → 5-fluoro-indirubin (251903-00-1)

Conditions	Yield
With sodium carbonate In methanol at 20℃; for 3h; Inert atmosphere;	95%

3-indoxyl acetate (608-08-2) + indole-2,3-dione (91-56-5) → indirubin (479-41-4)

Conditions	Yield
With sodium carbonate In methanol for 48h;	94%
With potassium carbonate In methanol at 20℃; for 25h;	85%
With sodium carbonate In methanol at 20℃; for 24.5h;	81%

3-indoxyl acetate (608-08-2) + indole-2,3-dione (91-56-5) → indirubin (479-41-4)

Conditions	Yield
With potassium carbonate In methanol at 20℃; for 5h; Inert atmosphere;	93%
With sodium carbonate In methanol at 25℃; for 36h;	82%
With sodium carbonate In methanol at 20℃;	73%

3-indoxyl acetate (608-08-2) + indole-2,3-dione (91-56-5) → indirubin-3'-oxime

Conditions	Yield
With sodium carbonate In methanol at 20℃; for 3h; Inert atmosphere;	93%
Multi-step reaction with 2 steps 1: sodium carbonate / methanol / 20 °C 2: hydroxylamine hydrochloride; pyridine / 2 h / 120 °C View Scheme
Multi-step reaction with 2 steps 1: sodium carbonate / methanol 2: hydroxylamine hydrochloride; pyridine / Heating View Scheme

7-fluoro-1H-indole-2,3-dione (317-20-4) + 3-indoxyl acetate (608-08-2) → C16H9FN2O2

Conditions	Yield
With sodium carbonate In methanol at 20℃;	93%

3-indoxyl acetate (608-08-2) + 1H-indole-2,3-dione-5-carboxylic acid (25128-32-9) → indirubin-5-carboxylic acid (1238056-78-4)

Conditions	Yield
With sodium carbonate In methanol at 20℃; for 20h; Inert atmosphere;	92%

3-indoxyl acetate (608-08-2) + 6-(Trifluoromethyl)-1H-indol-2,3-dione (343-69-1) → 6-trifluoromethylindirubin (1257060-35-7)

Conditions	Yield
With toluene-4-sulfonic acid In ethanol at 65 - 70℃; for 3h;	91%

7-bromoisatin (20780-74-9) + 3-indoxyl acetate (608-08-2) → 7-bromoindirubin (950669-85-9)

Conditions	Yield
With sodium carbonate In methanol at 20℃;	91%
With sodium carbonate In methanol
With sodium carbonate In methanol

5-Aminoisatin (42816-53-5) + 3-indoxyl acetate (608-08-2) → 5-Aminoindirubin (910035-26-6)

Conditions	Yield
With sodium carbonate In methanol at 20℃; for 3h;	90%
Stage #1: 5-Aminoisatin; 3-indoxyl acetate In methanol at 25℃; for 0.416667h; Stage #2: With sodium carbonate In methanol at 25℃; for 3h;	90%
With sodium carbonate In methanol at 45℃; for 1h; Inert atmosphere;	90%

3-indoxyl acetate (608-08-2) + N-(2,3-dioxoindolin-5-yl)acetamide (75591-28-5) → 5-Acetylaminoindirubin (910035-28-8)

Conditions	Yield
With sodium carbonate In methanol at 20℃; for 3h;	90%
With sodium carbonate In methanol at 45℃; for 1h; Inert atmosphere;	90%

3-indoxyl acetate (608-08-2) + 1-methyl-5-nitro-1H-indole-2,3-dione (3484-32-0) → 1-Methyl-5-nitroindirubin

Conditions	Yield
With sodium carbonate In methanol at 20℃; for 3h;	90%

7-iodoisatin (20780-78-3) + 3-indoxyl acetate (608-08-2) → 7-Iodoindirubin (906660-39-7)

Conditions	Yield
With sodium carbonate In methanol	90%

6-bromoisatin (6326-79-0) + 3-indoxyl acetate (608-08-2) → 6-Bromoindirubin (667463-60-7)

Conditions	Yield
Stage #1: 6-bromoisatin; 3-indoxyl acetate In methanol for 0.416667h; Stage #2: With sodium carbonate In methanol for 3h;	90%
With sodium carbonate In methanol at 25℃; for 5h; Inert atmosphere; Darkness;	90%
With toluene-4-sulfonic acid In ethanol at 65 - 70℃; for 3h;	87%

3-indoxyl acetate (608-08-2) + 6-bromo-5-aminoisatin (851366-93-3) → 6-bromo-5-aminoindirubin

Conditions	Yield
Stage #1: 3-indoxyl acetate; 6-bromo-5-aminoisatin In methanol at 25℃; for 0.416667h; Stage #2: With sodium carbonate In methanol at 25℃; for 3h;	90%

3-indoxyl acetate (608-08-2) + 5-nitroisatin (611-09-6) → 5-Nitroindirubin (910035-18-6)

Conditions	Yield
With sodium carbonate In methanol at 20℃; for 3h;	89%
With sodium carbonate In methanol at 45℃; for 1h; Inert atmosphere;	89%
With sodium carbonate In methanol at 20℃;
With sodium carbonate In methanol at 20℃;
With sodium carbonate

6-bromoisatin (6326-79-0) + 3-indoxyl acetate (608-08-2) → 6′-bromoindirubin (200273-66-1)

Conditions	Yield
With sodium carbonate In methanol at 20℃; for 3h; Inert atmosphere;	89%
With sodium carbonate In methanol at 20℃; Inert atmosphere;	85%
With sodium carbonate In methanol
In methanol Alkaline conditions;
With sodium carbonate In methanol

7-chloroisatin (7477-63-6) + 3-indoxyl acetate (608-08-2) → C16H9ClN2O2

Conditions	Yield
With sodium carbonate In methanol at 20℃;	88%

7-iodo-1-methylindolin-2,3-dione (906660-36-4) + 3-indoxyl acetate (608-08-2) → 7-Iodo-1-methylindirubin (906660-42-2)

Conditions	Yield
With sodium carbonate In methanol	87%

3-indoxyl acetate (608-08-2) + 4-dimethylamino-benzaldehyde (100-10-7) → (Z)-2-(4-(dimethylamino)benzylidene)indolin-3-one (38072-53-6)

Conditions	Yield
Stage #1: 3-indoxyl acetate With sodium hydroxide In methanol; water at 100℃; for 0.25h; Inert atmosphere; Stage #2: 4-dimethylamino-benzaldehyde In methanol; water at 0 - 20℃; for 72h; Inert atmosphere;	86%

3-indoxyl acetate (608-08-2) + ethyl (2Z)-3-bromo-2-(hydroxyimino)propanoate (127033-04-9) → ethyl α-(hydroxyimino)-β-(3-acetoxyindolen-3-yl)propanoate (106040-13-5) + 3-(ethoxycarbonyl)-4a-acetoxy-4,4a,9,9a-tetrahydro-1,2-oxazino<5,6-b>indole (106040-12-4)

Conditions	Yield
With sodium carbonate In dichloromethane for 18h; Ambient temperature;	A 15% B 85%

7-bromoisatin (20780-74-9) + 3-indoxyl acetate (608-08-2) → 7-Bromoindirubin (906660-38-6)

Conditions	Yield
With sodium carbonate In methanol	85%
With sodium carbonate In methanol at 20℃; for 3.5h; Inert atmosphere;
With sodium carbonate In methanol

3-indoxyl acetate (608-08-2) + 7-trifluoromethylisatin (391-12-8) → (2’Z)-7-trifluoromethyl-indirubin (1409933-16-9)

Conditions	Yield
With sodium carbonate In methanol at 20℃; for 3.5h; Inert atmosphere;	85%

7-bromo-1-methylindoline-2,3-dione (906660-35-3) + 3-indoxyl acetate (608-08-2) → 7-Bromo-1-methylindirubin (906660-41-1)

Conditions	Yield
With sodium carbonate In methanol	83%
With sodium carbonate In methanol at 20℃; for 3.5h;

3-indoxyl acetate (608-08-2) + acetic anhydride (108-24-7) → N,O-diacetylindoxyl (16800-67-2)

Conditions	Yield
With triethylamine at 80 - 90℃; for 0.5h;	82%
With dmap; triethylamine In tetrahydrofuran for 3h; Heating / reflux;	67%

benzo-[b]thiophene-2,3-dione (493-57-2) + 3-indoxyl acetate (608-08-2) → (2'Z)-thioindirubin

Conditions	Yield
With hydrogenchloride; acetic acid In water at 20℃; for 18h; Darkness;	82%

6-bromoisatin (6326-79-0) + 3-indoxyl acetate (608-08-2) → indirubin (479-41-4)

Conditions	Yield
With sodium sulfate; triethylamine In tetrahydrofuran; isopropyl alcohol at 30℃; for 60h; Enzymatic reaction;	82%

Upstream product

• 120-72-9 indole 
• 3240-34-4 [bis(acetoxy)iodo]benzene 
• 6245-93-8 3-hydroxy-1H-indole-2-carboxylic acid 
• 67790-18-5 3-methoxycarbonyl-5H-1,2-benzodiazepine 
• 2570-63-0 thallium(III) acetate 
• 140843-81-8 1-Nitrosoindol-3-yl acetate 
• 480-93-3 indoxyl 
• 108-24-7 acetic anhydride 
• 100063-39-6 2-Acetyl-1H-indol-3-yl-acetat 
• 26340-47-6 3-Iodo-1H-indole 
• 563-63-3 silver(I) acetate 
• 612-42-0 phenylglycine-o-carboxylic acid 

Downstream Products

• 106040-17-9 ethyl α-(benzyloximino)-β-<2-((3-methyl-2-butenyl)thio)-3-(3-methyl-2-butenyl)indolen-3-yl>propanoate 
• 106040-18-0 ethyl α-(benzyloximino)-β-<2-(ethylthio)-3-(1,1-dimethyl-2-propenyl)indolen-3-yl>propanoate 
• 106063-02-9 ethyl α-(benzyloximino)-β-<2-(ethylthio)-N-(3-methyl-2-butenyl)indol-3-yl>propanoate 
• 106040-16-8 ethyl α-(benzyloximino)-β-<2-(ethylthio)-3-(3-methyl-2-butenyl)indolen-3-yl>propanoate 
• 106040-15-7 ethyl α-(benzyloximino)-β-<2-(methylthio)-3-(3-methyl-2-butenyl)indolen-3-yl>propanoate 
• 106040-20-4 2-[(Z)-Benzyloxyimino]-3-[2-(3-methyl-but-2-enylsulfanyl)-1H-indol-3-yl]-propionic acid ethyl ester 
• 106040-19-1 ethyl α-(benzyloximino)-β-<2-(ethylthio)indol-3-yl>propanoate 

Relevant articles and documents

Preparation method of 3-substituted oxidized indole and derivative

The invention belongs to the technical field of organic chemistry and pharmaceutical chemistry and particularly relates to a method of preparing 3-substituted oxidized indole and a derivative. In themethod, with a 3-substituted indole derivative as a raw material and one or more of a tetrabutyl ammonium halide compound/sodium chloride/sodium iodide/potassium iodide as additives, and one or more of dichloromethane/1,2-dichloroethane/tetrahydrofurane/methylbenzene/1,4-dioxane/ethyl acetate/methanol are added as solvents; then one or more of [bis(trifluoroacetoxyl)iodine]benzene/iodosobenzene diacetate are added as oxidants in order to carry out a reaction with reaction temperature being controlled, thus producing the 3-substituted oxidized indole derivative. The method has gentle reaction conditions, simple operations, short reaction time and high yield, and is free of a metal catalyst and is environment-friendly.

COMPOUNDS HAVING 5-HT6 RECEPTOR AFFINITY

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Kinetic Study of the Nitrosation of 3-Substituted Indoles

Kinetic studies of the nitrosation reaction of three 3-substituted indoles (3-methylindole, indol-3-yl acetate and indole-3-acetic acid) show that the final state is an equilibrium between the reactants (nitrous acid and indole derivative) and the 1-nitroso derivative.Values of the rate constants for the nitrosation of the three indoles and denitrosation of the corresponding nitrosoindoles as well as values of the equilibrium constants have been obtained.The almost complete insensitivity of the reaction rates to medium acidity, the absence of catalysis by the usual catalysts of nitrosation (halides) and the high reactivity at low acidities, are in contrast to the kinetic characteristics of other N-nitrosation reactions.This atypical behaviour is discussed in terms of possible reaction mechanisms.