475102-13-7

Basic information

• Product Name: 5-Bromo-1-(tert-butoxycarbonyl)-1H-indol-2-ylboronic acid
• Synonyms: N-BOC-5-BROMOINDOLE-2-BORONIC ACID;5-Bromoindol-2-ylboronic acid, N-BOC protected;5-BROMO-N-(BUTOXYCARBONY)INDOKE-2-BORONIC ACID;5-Bromo-1H-indole-2-boronic acid, N-BOC protected;1H-Indole-1-carboxylicacid,2-borono-5-bromo-,1-(1,1-dimethylethyl)ester(9CI);5-Bromo-1-(tert-butoxycarbonyl)-1H-indole-2-boronic acid;1H-Indole-1-carboxylic acid, 2-borono-5-bromo-, 1-(1,1-dimethylethyl) ester;1-(tert-butoxycarbonyl)-5-bromo-1H-indol-2-yl-2-boronic acid
• CAS NO: 475102-13-7
• Molecular Formula: C₁₃H₁₅BBrNO₄
• Molecular Weight: 339.98
• Product Categories: BORONICACID;blocks;BoronicAcids;IndolesOxindoles;Boronic acids;Boronic acid;Indole;Organoborons;Boronic Acids;Boronic Acids and Derivatives;Heteroaryl
• Mol File: 475102-13-7.mol

Chemical Properties

• Melting Point: 93 °C
• Boiling Point: 488.3 °C at 760 mmHg
• Flash Point: 249.1 °C
• Appearance: white to light yellow crystal powder
• Density: 1.45
• Vapor Pressure: 2.39E-10mmHg at 25°C
• Refractive Index: 1.576
• Storage Temp.: Keep Cold
• CAS DataBase Reference: 5-Bromo-1-(tert-butoxycarbonyl)-1H-indol-2-ylboronic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Bromo-1-(tert-butoxycarbonyl)-1H-indol-2-ylboronic acid(475102-13-7)
• EPA Substance Registry System: 5-Bromo-1-(tert-butoxycarbonyl)-1H-indol-2-ylboronic acid(475102-13-7)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 22-26-36/37/39
• WGK Germany: 3
• Hazardous Substances Data: 475102-13-7(Hazardous Substances Data)

Usage

Chemical Properties

white to light yellow crystal powde

InChI:InChI=1/C13H15BBrNO4/c1-13(2,3)20-12(17)16-10-5-4-9(15)6-8(10)7-11(16)14(18)19/h4-7,18-19H,1-3H3

Upstream product

• 10075-50-0 5-bromo-1H-indole 
• 5419-55-6 Triisopropyl borate 
• 7732-18-5 water 
• 182344-70-3 5-bromo-indole-1-carboxylic acid tert-butyl ester 
• 24424-99-5 di-tert-butyl dicarbonate 

Downstream Products

• 1187841-24-2 dimethyl 2-(2-((5-bromo-1-(tert-butoxycarbonyl)-1H-indol-2-yl)methyl)benzylidene)malonate 
• 1222174-96-0 5-bromo-2-(4-fluoro-3-methyl-phenyl)-indole-1-carboxylic acid tert-butyl ester 
• 1416632-67-1 potassium N-Boc-5-bromo-2-indolyltrifluoroborate 

Relevant articles and documents

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JAK INHIBITOR

A JAK inhibitor comprising, as an active ingredient, a nitrogen-containing heterocyclic compound represented by formula (I) {wherein W represents a nitrogen atom or -CH-; X represents -C (=O) - or -CHR4- (wherein R4 represents a hydrogen atom, or the like); R1 represents the formula described below [wherein Q1 represents-CR8-(wherein R8 represents a hydrogen atom, substituted or unsubstituted lower alkyl, or the like); Q2 represents -NR15- (wherein R15 represents a hydrogen atom, substituted or unsubstituted lower alkyl, or the like); and R5 and R6 may be the same or different and each represents a hydrogen atom, halogen, carboxy, substituted or unsubstituted lower alkyl, or the like], or the like; and R2 and R3 may be the same or different and each represents a hydrogen atom, halogen, substituted or unsubstituted lower alkyl, or the like} or a pharmaceutically acceptable salt thereof.

A non-cryogenic method for the preparation of 2-(indolyl) borates, silanes, and silanols

2-Indolyl borates are prepared via addition of LDA to a mixture of N-Bo-indole and triisopropyl borate at 0-5 °C. Following acidic hydrolysis, the boronic acids are isolated by crystallization in good to excellent yield (73-99%). The method is quite general, tolerating a wide range of functional groups, and also provides access to 2-silyl derivatives (80-91%).