29245-44-1

Basic information

• Product Name: 5-bromo-2-(5-bromo-4-chloro-1,3-dihydro-3-oxo-2H-indol-2-ylidene)-4-chloro-1,2-dihydro-3H-indol-3-one
• Synonyms: 5-bromo-2-(5-bromo-4-chloro-1,3-dihydro-3-oxo-2H-indol-2-ylidene)-4-chloro-1,2-dihydro-3H-indol-3-one;4,4'-Dichloro-5,5'-dibromo-Δ2,2'-biindoline-3,3'-dione;5,5'-Dibromo-4,4'-dichloro-Δ2,2'(3H,3'H)-bi[1H-indole]-3,3'-dione;BASF Brilliant Indigo 4G-D;BASF Brilliant Indigo 4G-N;C.I.73045;C.I.Vat Blue 2
• CAS NO: 29245-44-1
• Molecular Formula: C₁₆H₆Br₂Cl₂N₂O₂
• Molecular Weight: 488.94504
• EINECS: 249-533-2
• Mol File: 29245-44-1.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 556.3°Cat760mmHg
• Flash Point: 290.2°C
• Appearance: /
• Density: 2.026g/cm³
• Vapor Pressure: 2.05E-12mmHg at 25°C
• Refractive Index: 1.74
• CAS DataBase Reference: 5-bromo-2-(5-bromo-4-chloro-1,3-dihydro-3-oxo-2H-indol-2-ylidene)-4-chloro-1,2-dihydro-3H-indol-3-one(CAS DataBase Reference)
• NIST Chemistry Reference: 5-bromo-2-(5-bromo-4-chloro-1,3-dihydro-3-oxo-2H-indol-2-ylidene)-4-chloro-1,2-dihydro-3H-indol-3-one(29245-44-1)
• EPA Substance Registry System: 5-bromo-2-(5-bromo-4-chloro-1,3-dihydro-3-oxo-2H-indol-2-ylidene)-4-chloro-1,2-dihydro-3H-indol-3-one(29245-44-1)

Safety Data

• Hazardous Substances Data: 29245-44-1(Hazardous Substances Data)

Usage

Preparation

(a) in the Chloroacetic acid or methyl bromide in sulfate Janson 3H-indol-3-one,2-(1,3-dihydro-3-oxo-2H-indol-2-ylidene)-1,2-dihydro- (namely VAT dye C.I. 73025) [FIAT 764 and 1313], or in the cold sulfuric acid in?3H-indol-3-one,2-(1,3-dihydro-3-oxo-2H-indol-2-ylidene)-1,2-dihydro- (GP 23496 l); (b) 3-Bromo-6-(carboxymethylamino)-2-chlorobenzoic acid?and Sodium methanolate reaction, product with Potassium hydroxide treatment, and air oxidation (USP 957683). Note: C.I. 73025 chemical structure as above.

Properties and Applications

green light blue. Soluble in Xylene is blue. In concentrated sulfuric acid to green light blue, dilution after blue floc precipitation; In the basic insurance powder solution for yellow brown; In the acidic insurance powder solution for colorless. Standard Ironing Fastness Chlorine bleach Light Fastness Mercerized Oxygen bleach Soaping Fading Stain ISO 4-5 3 3-4 3 2-3

Standard

Ironing Fastness

Fading

Stain

ISO

4-5

InChI:InChI=1/C16H6Br2Cl2N2O2/c17-5-1-3-7-9(11(5)19)15(23)13(21-7)14-16(24)10-8(22-14)4-2-6(18)12(10)20/h1-4,21-22H/b14-13-

Upstream product

• 125328-76-9 1-acetyl-5-bromo-4-chloro-3-hydroxyindole 
• 1174456-59-7 5-bromo-4-chloroindoxyl α-D-galactopyranoside 
• 3030-06-6 1-acetyl-5-bromo-4-chloro-3-indolyl acetate 
• 3252-36-6 (5-bromo-4-chloroindol-3-yl) acetate 
• 117887-41-9 5-bromo-4-chloro-3-hydroxyindole 
• 15548-60-4 (5-bromo-4-chloroindol-3-yl)-β-D-glucopyranoside 
• 4264-82-8 5-bromo-4-chloro-3-indolylacetyl-beta-D-glucosaminide 
• 7240-90-6 5-bromo-4-chloro-3-indolyl β-D-galactopyranoside 
• 38404-93-2 5-bromo-4-chloro-3-indolyl phosphate 

Relevant articles and documents

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CROSS-LINKING COMPOUNDS AND METHODS OF USE THEREOF

Compounds comprising a cross-linking moiety and a protecting group are described herein along with their methods of use. The cross-linking moiety may comprise an indoxyl and the protecting group may comprise a sugar (e.g., a glucuronide or glucoside), phosphoester, or sulfoester group. The cross-linking moiety and protecting group may be attached to each other via an oxygen atom, sulfur atom, or linker. In some embodiments, the linker attaching the cross-linking moiety and protecting group is a self-immolative linker. A compound of the present invention may cross-link under physiological conditions and/or in vivo.

Enzymatically triggered chromogenic cross-linking agents under physiological conditions

The ability to cross-link molecules upon enzymatic action under physiological conditions holds considerable promise for use in diverse life sciences applications. Here, an enzymatically triggered "click reaction" has been developed by exploiting the longstanding indigo-forming reaction from indoxyl β-glucoside. The covalent cross-linking proceeds in aqueous solution, requires the presence only of an oxidant (e.g., O2), and is readily detectable owing to the blue color of the resulting indigoid dye. To achieve facile indigoid formation in the presence of a bioconjugatable tether, diverse indoxyl β-glucosides were synthesized and studied in enzyme assays with four glucosidases including from tritosomes (derived from hepatic lysosomes) and rat liver homogenates. Altogether 36 new compounds (including 15 target indoxyl-glucosides for enzymatic studies) were prepared and fully characterized in pursuit of four essential requirements: enzyme triggering, facile subsequent indigoid dye formation, bioconjugatability, and synthetic accessibility. The 4,6-dibromo motif in a 5-alkoxy-substituted indoxyl-glucoside was a key design feature for fast and high-yielding indigoid dye formation. Two attractive molecular designs include (1) an indoxyl-glucoside linked to a bicyclo[6.1.0]nonyl (BCN) group for Cu-free click chemistry, and (2) a bis(indoxyl-glucoside). In both cases the linker between the reactive moieties is composed of two short PEG groups and a central triazine derivatized with a sulfobetaine moiety for water solubilization. Glucosidase treatment of the bis(indoxyl-glucoside) in aqueous solution gave oligomers that were characterized by absorption, dynamic light-scattering, and 1H NMR spectroscopy; optical microscopy; mass spectrometry; and HPLC. Key attractions of in situ indigoid dye formation, beyond enzymatic triggering under physiological conditions without exogenous catalysts or reagents, are the chromogenic readout and compatibility with attachment to diverse molecules.

Enzymatic glycosylation of indoxyglycosides catalyzed by a novel maltose phosphorylase from Emticicia oligotrophica

Maltose phosphorylases (EC 2.4.1.8) catalyze the reversible conversion of maltose to glucose and glucose-1-phosphate in the presence of inorganic phosphate. Herein, we describe for the first time the use of a maltose phosphorylase for the synthesis of various anomerically modified diglycosides. The maltose phosphorylase used was isolated from the bacterium Emticicia oligotrophica and showed a high selectivity towards the phosphorolysis of maltose, whereas no phosphorolysis was observed using other glucose-containing disaccharides such as cellobiose, melibiose, sucrose and trehalose. The addition of glucose to various 5-bromo-4-chloro-3-indolyl-glycosides (X-sugars) was used to evaluate the promiscuity of the maltose phosphorylase, and product formation was verified by LC-ESI-MS and MALDI-TOF-MS. The simple expression and purification protocol and the use of maltose as an inexpensive starting material make this maltose phosphorylase from Emticicia oligotrophica a valuable novel biocatalyst for the synthesis of glucose-containing glycosides.