17357-14-1

Basic information

• Product Name: 3-ACETOXY-5-BROMOINDOLE
• Synonyms: 3-ACETOXY-5-BROMOINDOLE;5-BROMOINDOXYL-3-ACETATE;5-BROMOINDOXYL ACETATE;5-BROMOINDOLYL 3-ACETATE;5-BROMO-1H-INDOL-3-YL ACETATE;O-ACETYL-5-BROMOINDOXYL;5-BROMOINDOLYL ACETATE;5-BROMOINDOXYL-3-ACETATE 98%
• CAS NO: 17357-14-1
• Molecular Formula: C₁₀H₈BrNO₂
• Molecular Weight: 254.08
• EINECS: 241-387-8
• Product Categories: Heterocyclic Compounds;Indoles;Simple Indoles;substrate
• Mol File: 17357-14-1.mol
• Article Data: 7

Chemical Properties

• Melting Point: 130-132 °C(lit.)
• Boiling Point: 393.3 °C at 760 mmHg
• Flash Point: 191.6 °C
• Appearance: White to off-white powder
• Density: 1.632 g/cm³
• Vapor Pressure: 2.16E-06mmHg at 25°C
• Refractive Index: 1.661
• Storage Temp.: 2-8°C
• Solubility: ethanol: soluble50mg/mL, clear, colorless
• BRN: 168698
• CAS DataBase Reference: 3-ACETOXY-5-BROMOINDOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-ACETOXY-5-BROMOINDOLE(17357-14-1)
• EPA Substance Registry System: 3-ACETOXY-5-BROMOINDOLE(17357-14-1)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• F: 8-10
• Hazardous Substances Data: 17357-14-1(Hazardous Substances Data)

Usage

Description

3-ACETOXY-5-BROMOINDOLE is a halogenated heterocyclic compound that serves as an esterase substrate. It is characterized by the presence of an indole ring with a bromine atom at the 5-position and an acetoxy group at the 3-position. This unique structure allows it to be utilized in various applications across different industries.

Uses

Used in Histochemical Studies:
3-ACETOXY-5-BROMOINDOLE is used as an esterase substrate for investigating the activity of non-specific esterase in the matrix of developing bovine enamel. This application aids researchers in understanding the enzymatic processes involved in the development and maturation of dental enamel.
Used in Mouse Epididymis Research:
In the field of reproductive biology, 3-ACETOXY-5-BROMOINDOLE is used as a substrate to study the esterase activity in mouse epididymis epithelial cells. This helps in exploring the role of esterases in the epididymis and their potential involvement in sperm maturation and function.
Used in Guinea-Pig Thyroid Research:
3-ACETOXY-5-BROMOINDOLE is also employed as a substrate to investigate esterase activity in guinea-pig thyroid cells. This application is valuable for studying the enzymatic processes in the thyroid gland and their implications in thyroid hormone synthesis and regulation.
Used in Staining Procedures:
In the context of histology and pathology, 3-ACETOXY-5-BROMOINDOLE is used in staining procedures for the frozen sections of muscle fixed in buffered formaldehyde. This allows for the visualization and analysis of esterase activity in muscle tissues, providing insights into muscle metabolism and function.

InChI:InChI=1/C10H8BrNO2/c1-6(13)14-10-5-12-9-3-2-7(11)4-8(9)10/h2-5,12H,1H3

Upstream product

• 33588-54-4 5-bromoindoxyl diacetate 
• 10075-50-0 5-bromo-1H-indole 
• 3240-34-4 [bis(acetoxy)iodo]benzene 
• 868694-19-3 5-bromo-3-iodo-1H-indole 
• 563-63-3 silver(I) acetate 
• 64-19-7 acetic acid 

Downstream Products

• 84-40-2 (E)-5,5′-dibromo-[2,2′-biindolinylidene]-3,3'-dione 
• 126433-42-9 5-Iodoindirubin 
• 331467-03-9 5-iodoindirubin-3'-oxime 
• 84-40-2 5,5'-dibromo-1H,1'H-[2,2']biindolylidene-3,3'-dione 
• 33588-54-4 5-bromoindoxyl diacetate 
• 106698-07-1 1-acetyl-5-bromo-1,2-dihydro-3H-indol-3-one 
• 114165-30-9 1-acetyl-5-bromo-3-hydroxyindole 

Relevant articles and documents

High performance ambipolar organic field-effect transistors based on indigo derivatives

A bio-inspired organic semiconductor 5,5′-diphenylindigo shows excellent and well-balanced ambipolar transistor properties; its hole and electron mobilities are 0.56 and 0.95 cm2 V-1 s-1, respectively. The enhanced performance is attributed to the extended π-π overlap of the phenyl groups as well as the characteristic packing pattern that is a hybrid of the herringbone and brickwork structures. The ambipolar transistor characteristics are analyzed considering its operating regions, where a large unipolar saturated region appears due to the difference of the electron and hole threshold voltages.

PHOTOPROTECTIVE COMPOSITIONS CONTAINING MALASSEZIA-DERIVED COMPOUNDS AND/OR CHEMICAL ANALOGS THEREOF

The present invention relates to compounds, compositions, and methods for modulating skin pigmentation and treating or preventing UV-induced skin damage, erythema, aging of the skin, sunburn, and hyperpigmentation in a subject. The compounds, compositions, and methods of the present invention generally involve Malassezia-derived compounds, including malassezin and indirubin, and/or chemical analogs thereof. Other applications of the compounds and compositions disclosed herein include, but are not limited to, improving hyperpigmentation caused by a hyperpigmentation disorder, inducing melanocyte apoptosis, and modulating arylhydrocarbon receptor (AhR) activity, melanogenesis, melanin production, melanosome biogenesis, melanosome transfer, melanocyte activity, and melanin concentration.

An iodine effect in ambipolar organic field-effect transistors based on indigo derivatives

5,5′-Diiodoindigo (4) exhibits excellent ambipolar transistor properties with hole/electron mobilities of μh/μe = 0.42/0.85 cm2 V-1 s-1. The halogen substituted indigos show decreasing tilt angles from F to I in the crystals. In addition, the iodine-iodine interaction provides extraordinarily large interchain interaction. However, the X-ray diffraction suggests that the indigo molecules are arranged approximately perpendicular to the substrate in the thin films, probably due to the extra iodine-iodine interaction. The remarkable performance is ascribed to this characteristic supramolecular interaction.