475102-14-8

Basic information

• Product Name: 1-BOC-5-METHYL-1H-INDOLE-2-BORONIC ACID
• Synonyms: N-TERT-BUTOXYCARBONYL-5-METHYL-1H-INDOLE-2-BORONIC ACID;5-Methyl-1H-indole-2-boronic acid, BOC protected;5-Methyl-1H-indole-2-boronic acid, BOC protected 97%;1H-Indole-1-carboxylicacid,2-borono-5-methyl-,1-(1,1-dimethylethyl)ester(9CI);N-BOC-5-METHYL-1H-INDOLE-2-BORONIC ACID;1H-Indole-1-carboxylic acid, 2-borono-5-methyl-, 1-(1,1-dimethylethyl) ester;1-(tert-butoxycarbonyl)-5-methyl-1H-indol-2-yl-2-boronic acid;N-Boc-5-Methyl-1H-indol-2-yl boronic acid
• CAS NO: 475102-14-8
• Molecular Formula: C₁₄H₁₈BNO₄
• Molecular Weight: 275.11
• Product Categories: BORONICACID;blocks;BoronicAcids;IndolesOxindoles
• Mol File: 475102-14-8.mol
• Article Data: 2

Chemical Properties

• Melting Point: 112-116
• Boiling Point: 456.8 °C at 760 mmHg
• Flash Point: 230.1 °C
• Appearance: /
• Density: 1.16 g/cm³
• Vapor Pressure: 3.87E-09mmHg at 25°C
• Refractive Index: 1.541
• Storage Temp.: Keep Cold
• CAS DataBase Reference: 1-BOC-5-METHYL-1H-INDOLE-2-BORONIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 1-BOC-5-METHYL-1H-INDOLE-2-BORONIC ACID(475102-14-8)
• EPA Substance Registry System: 1-BOC-5-METHYL-1H-INDOLE-2-BORONIC ACID(475102-14-8)

Safety Data

• Hazard Codes: Xi
• Hazardous Substances Data: 475102-14-8(Hazardous Substances Data)

Usage

General Description

1-BOC-5-METHYL-1H-INDOLE-2-BORONIC ACID is a boronic acid derivative containing a BOC (tert-butyloxycarbonyl) protecting group and a 5-methyl-1H-indole moiety. It is commonly used in organic synthesis as a building block for various pharmaceuticals and agrochemicals. The boronic acid functionality allows for it to undergo Suzuki-Miyaura cross-coupling reactions with aryl halides, which is a widely used method for forming carbon-carbon bonds. The BOC protecting group can be removed under mild conditions, making it a versatile intermediate in organic synthesis. Overall, 1-BOC-5-METHYL-1H-INDOLE-2-BORONIC ACID is a valuable compound for the preparation of complex organic molecules.

InChI:InChI=1/C14H18BNO4/c1-9-5-6-11-10(7-9)8-12(15(18)19)16(11)13(17)20-14(2,3)4/h5-8,18-19H,1-4H3

Upstream product

• 129822-49-7 5-methylindole-1-carboxylic acid tert-butyl ester 
• 614-96-0 5-methyl-1H-indole 
• 24424-99-5 di-tert-butyl dicarbonate 

Downstream Products

• 1356140-72-1 β-D-1-(3-methyl-pyrimido[4,5-d]pyrimido[1,6-a]indol-10-yl)-5-O-(4,4'-dimethoxytrityl)-2-deoxyribose-3-(2-cyanoethyl N,N-diisopropylphosphoramidite) 
• 1356140-71-0 β-D-1-(3-methyl-pyrimido[4,5-d]pyrimido[1,6-a]indol-10-yl)-5-O-(4,4'-dimethoxytrityl)-2-deoxyribose 
• 944707-85-1 C₂₉H₃₀N₂O₄S 

Relevant articles and documents

DNA duplexes and triplex-forming oligodeoxynucleotides incorporating modified nucleosides forming stable and selective triplexes

We have previously reported DNA triplexes containing the unnatural base triad G-PPI·C3, in which PPI is an indole-fused cytosine derivative incorporated into DNA duplexes and C3 is an abasic site in triplex-forming oligonucleotides (TFOs) introduced by a propylene linker. In this study, we developed a new unnatural base triad A-ψ·CR1 where ψ and CR1 are base moieties 2′-deoxypseudouridine and 5-substituted deoxycytidine, respectively. We examined several electron-withdrawing substituents for R1 and found that 5-bromocytosine (C Br) could selectively recognize ψ. In addition, we developed a new PPI derivative, PPIMe, having a methyl group on the indole ring in order to achieve selective triplex formation between DNA duplexes incorporating various Watson-Crick base pairs, such as T-A, C-G, A-ψ, and G-PPIMe, and TFOs containing T, C, CBr, and C3. We studied the selective triplex formation between these duplexes and TFOs using UV-melting and gel mobility shift assays.