75400-67-8

Basic information

• Product Name: 1-BOC-INDOLE
• Synonyms: TERT-BUTYL 1H-INDOLE-1-CARBOXYLATE;TERT-BUTYL 1-INDOLECARBOXYLATE;INDOLE, BOC PROTECTED;1-BOC-INDOLE;1-(TERT-BUTOXYCARBONYL)INDOLE;Indole, N-BOC protected;Indole, N-BOC protected 98%;N-BOC INDOLE
• CAS NO: 75400-67-8
• Molecular Formula: C₁₃H₁₅NO₂
• Molecular Weight: 217.26
• EINECS: -0
• Product Categories: blocks;IndolesOxindoles;Indole;Building Blocks;Heterocyclic Building Blocks;Indoles
• Mol File: 75400-67-8.mol

Chemical Properties

• Melting Point: 24-26
• Boiling Point: 201 °C(lit.)
• Flash Point: 160 °F
• Appearance: /
• Density: 1.07 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.000368mmHg at 25°C
• Refractive Index: n20/D 1.543(lit.)
• Storage Temp.: Keep Cold
• BRN: 4674239
• CAS DataBase Reference: 1-BOC-INDOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-BOC-INDOLE(75400-67-8)
• EPA Substance Registry System: 1-BOC-INDOLE(75400-67-8)

Safety Data

• Hazard Codes: Xi
• Safety Statements: 24/25
• WGK Germany: 3
• HazardClass: IRRITANT, KEEP COLD
• Hazardous Substances Data: 75400-67-8(Hazardous Substances Data)

Usage

Uses

1. Used in Pharmaceutical Industry:
1-Boc-Indole is used as a reactant for the preparation of potent plant-growth inhibitors, which are essential in the development of new agrochemicals and plant growth regulators.
2. Used in Medicinal Chemistry:
1-Boc-Indole is used as a reactant for the preparation of cannabinoid CB2 receptor ligands, which have potential applications in the treatment of various medical conditions, including pain, inflammation, and neurodegenerative diseases.
3. Used in Drug Discovery:
1-Boc-Indole is used as a reactant for the synthesis of analogues of isomeridianin G and evaluation as GSK-3β inhibitors. These compounds have potential applications in the treatment of various diseases, including cancer and neurodegenerative disorders.
4. Used in Antibacterial Agents:
1-Boc-Indole is used as an inhibitor of the Yersinia pestis salicylate adenylation domain YbtE, which is a potential target for the development of new antibiotics against Yersinia pestis, the causative agent of plague.
5. Used in Gastrointestinal Applications:
1-Boc-Indole is used as a reactant for the preparation of cholecystokinin-2 receptor antagonists, which have potential applications in the treatment of gastrointestinal disorders, such as irritable bowel syndrome and pancreatitis.
6. Used in Antiparasitic Agents:
1-Boc-Indole is used as a reactant for the preparation of antileishmanial agents, which are essential in the development of new treatments for leishmaniasis, a vector-borne disease caused by protozoan parasites.
7. Used in Organic Synthesis:
1-Boc-Indole is used as a reactant for palladium-catalyzed Suzuki-Miyaura cross-coupling reactions, which are widely employed in the synthesis of various organic compounds, including pharmaceuticals, agrochemicals, and advanced materials.
8. Used in Friedel-Crafts Alkylation:
1-Boc-Indole is used as a reactant in Friedel-Crafts alkylation reactions, which are important in the synthesis of a wide range of organic compounds, including pharmaceuticals, agrochemicals, and natural products.

InChI:InChI=1/C13H15NO2/c1-13(2,3)16-12(15)14-9-8-10-6-4-5-7-11(10)14/h4-9H,1-3H3

Upstream product

• 5652-38-0 N-phenyl-β-alanine 
• 121494-14-2 3-((tert-butoxycarbonyl)(phenyl)amino)propanoic acid 
• 24424-99-5 di-tert-butyl dicarbonate 
• 120-72-9 indole 
• 1093942-95-0 tert-butyl benzyl(ethynyl)carbamate 
• 187099-49-6 2-((trimethylsilyl)ethynyl)phenylaminocarboxylic acid tert-butyl ester 
• 100-52-7 benzaldehyde 
• 192189-07-4 tert-butyl 3-iodo-1H-indol-1-carboxylate 
• 108-90-7 chlorobenzene 
• 369-57-3 benzenediazonium tetrafluoroborate 
• 100-68-5 methyl-phenyl-thioether 
• 119-61-9 benzophenone 
• 143262-10-6 1-(tert-butoxycarbonyl)indoline 

Downstream Products

• 120-72-9 indole 
• 19013-51-5 3-tert-butyl-1H-indole 
• 138343-89-2 tert-butyl 2-phenyl-1H-indole-1-carboxylate 
• 205310-48-1 tert-butyl 2-{[4-(tert-butyl)cyclohex-1-enyl]carbonyl}indol-1-carboxylate 
• 205310-54-9 tert-butyl 2-[(3,5,5-trimethylcyclohexa-1⁽⁶⁾,2-dienyl)carbonyl]indole-1-carboxylate 
• 261895-13-0 phenylmethyl 4-({1-[(tert-butyl)oxycarbonyl]indol-2-yl}ethylidene)-3-ethylidenepiperidine-1-carboxylate 
• 784161-48-4 2-(hydroxydimethylsilyl)-1H-indole-1-carboxylic acid 1,1-dimethylethyl ester 
• 872983-77-2 2-chlorosulfonyl-indole-1-carboxylic acid tert-butyl ester 
• 213318-44-6 N-Boc-indole-2-boronic acid 
• 639514-64-0 C₁₈H₁₅F₃N₂O₃S 
• 143259-56-7 3-bromoindole-1-carboxylic acid tert-butyl ester 
• 193810-88-7 2-(4-nitrophenyl)-1H-indole-1-carboxylic acid 1,1-dimethylethyl ester 
• 157427-60-6 2-(4-cyanophenyl)-1H-indole-1-carboxylic acid 1,1-dimethylethyl ester 
• 942070-45-3 tert-butyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole-1-carboxylate 

Relevant articles and documents

Decarboxylative Intramolecular Arene Alkylation Using N-(Acyloxy)phthalimides, an Organic Photocatalyst, and Visible Light

An intramolecular arene alkylation reaction has been developed using the organic photocatalyst 4CzIPN, visible light, and N-(acyloxy)phthalimides as radical precursors. Reaction conditions were optimized via high-throughput experimentation, and electron-rich and electron-deficient arenes and heteroarenes are viable reaction substrates. This reaction enables access to a diverse set of fused, partially saturated cores which are of high interest in synthetic and medicinal chemistry.

Transition-metal-free tunable chemoselective nfunctionalization of indoles with ynamides

Two unprecedented Nfunctionalizations of indoles with ynamides are described. By varying the electron-withdrawing group on the ynamide nitrogen atom, either Z-indolo-etheneamides or indolo-amidines can be selectively obtained under the same metal-free reaction conditions. The scope and synthetic potential of these reactions, as well as some mechanistic insights provided by DFT calculations, are reported.

Synthesis of 2-(1-phenylvinyl)benzofurans and 2-(1-phenylvinyl)indoles as antimitotic agents by a tandem palladium-assisted coupling-cyclization reaction between 1-phenylvinyl iodides and ortho-substituted arylalkynes

A series of functionalized 2-(1-phenylvinyl)benzofurans 2 and 2-(1-phenylvinyl)indoles 3 were prepared from 1-phenylvinyl iodides and silylated alkynes in a one-pot reaction. After a desilylation step, the Sonogashira coupling reaction between the resulti

Automated generation and reactions of 3-hydroxymethylindoles in continuous-flow microreactors

An automated sequential approach for the generation and reactions of 3-hydroxymethylindoles in continuous-flow microreactors is described. Consecutive halogen-magnesium exchanges of four 3-iodoindoles followed by addition to three aldehydes provided twelv

Potassium [1-(tert-butoxycarbonyl)-1H-indol-2-yl]trifluoroborate as an efficient building block in palladium-catalyzed Suzuki-Miyaura cross couplings

Potassium [1-(tert-butoxycarbonyl)-1H-indol-2-yl]trifluoroborate (1) was used in Suzuki-type coupling reactions. First, the best coupling conditions were assessed using bromobenzene as the electrophile. Then, 1 was successfully coupled with various aryl a

Asymmetric Deprotonations: Lithiation of N-(tert-Butoxycarbonyl)indoline with sec-Butyllithium/ (-)-Sparteine

The asymmetric lithiation of N-Boc indoline (1) with s-BuLi/(-)-sparteine and subsequent substitution provides the 2-substituted N-Boc indolines 3 and 5-11 with excellent enantiomeric ratios and in variable yields. The asymmetric lithiation-substitution sequence with N-Boc-7-chloroindoline (12) provides products 13-19 with good enantiomeric ratios. Mechanistic investigation establishes that the enantioselectivities arise from an initial asymmetric deprotonation to provide the enantioenriched and configurationally stable organolithium intermediates (S)-28 and (S)-29, which react stereoselectively with electrophiles.