475102-11-5

Basic information

• Product Name: 4-CHLORO-N-(BOC)-INDOLE-2-BORONIC ACID
• Synonyms: 1-BOC-4-CHLORO-2-INDOLEBORONIC ACID;1-BOC-4-CHLOROINDOLE-2-BORONIC ACID;4-CHLORO-1H-INDOL-2-YLBORONIC ACID, N-BOC PROTECTED;4-CHLORO-N-(BOC)-INDOLE-2-BORONIC ACID;4-Chloroindole-2-boronic acid, N-BOC protected;4-Chloroindole-2-boronic acid, N-BOC protected 98%;1H-Indole-1-carboxylicacid,2-borono-4-chloro-,1-(1,1-dimethylethyl)ester(9CI);N-BOC-4-CHLOROINDOLE-2-BORONIC ACID
• CAS NO: 475102-11-5
• Molecular Formula: C₁₃H₁₅BClNO₄
• Molecular Weight: 295.53
• Product Categories: BORONICACID;blocks;BoronicAcids;IndolesOxindoles
• Mol File: 475102-11-5.mol
• Article Data: 3

Chemical Properties

• Melting Point: 107-110
• Boiling Point: 471.366 °C at 760 mmHg
• Flash Point: 238.874 °C
• Appearance: /
• Density: 1.279 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.56
• Storage Temp.: Keep Cold
• PKA: 7.72±0.30(Predicted)
• CAS DataBase Reference: 4-CHLORO-N-(BOC)-INDOLE-2-BORONIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 4-CHLORO-N-(BOC)-INDOLE-2-BORONIC ACID(475102-11-5)
• EPA Substance Registry System: 4-CHLORO-N-(BOC)-INDOLE-2-BORONIC ACID(475102-11-5)

Safety Data

• Hazard Codes: Xi
• Hazardous Substances Data: 475102-11-5(Hazardous Substances Data)

Usage

General Description

4-Chloro-N-(Boc)-indole-2-boronic acid is a chemical compound with the molecular formula C14H13BClNO4. It is a boronic acid derivative with a 4-chloro substitution on the indole ring. The compound contains a Boc (tert-butyloxycarbonyl) protecting group on the nitrogen atom of the indole ring. Boronic acids are known for their ability to form stable covalent bonds with diols and have been widely used in organic synthesis and pharmaceutical research as building blocks for various biologically active molecules. The presence of the indole ring and the boronic acid functionality makes this compound a potentially valuable intermediate for the synthesis of complex organic molecules and pharmaceuticals.

InChI:InChI=1/C13H15BClNO4/c1-13(2,3)20-12(17)16-10-6-4-5-9(15)8(10)7-11(16)14(18)19/h4-7,18-19H,1-3H3

Upstream product

• 129822-46-4 tert-butyl 4-chloro-1H-indole-1-carboxylate 
• 25235-85-2 4-chloro-1H-indole 
• 24424-99-5 di-tert-butyl dicarbonate 
• 5419-55-6 Triisopropyl borate 

Downstream Products

• 1004558-24-0 4-chloro-2-(4-chloro-3-cyclohexylsulfamoyl-phenyl)-indole-1-carboxylic acid tert-butyl ester 
• 1443151-93-6 tert-butyl 4-chloro-2-(4-{[2-(4-fluorophenyl)ethyl]amino}-6-methoxy-1,3,2-triazin-2-yl)-1H-indole-1-carboxylate 
• 1443151-42-5 4-(4-chloro-1H-indol-2-yl)-N-[2-(4-fluorophenyl)ethyl]-6-methoxy-1,3,5-triazin-2-amine 

Relevant articles and documents

1,3,5-TRIAZINE-2-AMINE DERIVATIVES, PREPARATION THEREOF AND DIAGNOSTIC AND THERAPEUTIC USE THEREOF

The present invention relates to compounds corresponding to formula (I) in which: - R1 represents a substituted phenyl; - R2 represents: - a substituted phenyl; - a heteroaromatic group, the said group being unsubstituted or substituted one or more times; - R3 represents a group Alk; - R4 represents a hydrogen atom or a (C1-C4)alkyl; - R5 represents a hydrogen atom, a (C3-C6)cycloalkyl or a (C1-C4)alkyl-O-Alk; - or alternatively R4 and R5, together with the nitrogen atom to which they are attached, constitute a heterocyclic radical chosen from: azetidin-1-yl, pyrrolidin-1-yl, piperid-1-yl, morpholin-4-yl; - R6 represents a group -COOAlk, a group -CONH2 or a group -NHSO2 Alk; - Alk represents a (C1-C4)alkyl, which is unsubstituted or substituted one or more times with a halogen atom; in the form of the base or of an acid-addition salt. Preparation process and diagnostic and therapeutic use

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%).