5176-27-2

Basic information

• Product Name: N-T-BOC-PYRROLE
• Synonyms: TERT-BUTYL PYRROL-1-CARBOXYLATE;TERT-BUTYL 1-PYRROLECARBOXYLATE;N-T-BOC-PYRROLE;N-BOC-1H-PYRROLE;N-Boc-Pyrrole;1-Boc-pyrrole;t-Butyl 1H-pyrrole-1-carboxylate;tert-butyl-pyrrole-carboxylate,98%
• CAS NO: 5176-27-2
• Molecular Formula: C₉H₁₃NO₂
• Molecular Weight: 167.21
• Product Categories: Building Blocks;Chemical Synthesis;Heterocyclic Building Blocks;Pyrroles;carboxylic ester
• Mol File: 5176-27-2.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 91-92 °C20 mm Hg(lit.)
• Flash Point: 167 °F
• Appearance: Colorless to yellow/Solution
• Density: 1 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0977mmHg at 25°C
• Refractive Index: n20/D 1.4685(lit.)
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Acetonitrile, Dichloromethane, Ethyl Acetate, Methanol, Tetrahydrofuran
• PKA: -6.10±0.70(Predicted)
• CAS DataBase Reference: N-T-BOC-PYRROLE(CAS DataBase Reference)
• NIST Chemistry Reference: N-T-BOC-PYRROLE(5176-27-2)
• EPA Substance Registry System: N-T-BOC-PYRROLE(5176-27-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26
• WGK Germany: 3
• Hazardous Substances Data: 5176-27-2(Hazardous Substances Data)

Usage

Chemical Properties

Colorless liquid

Uses

Different sources of media describe the Uses of 5176-27-2 differently. You can refer to the following data:
1. Pyrrole-1-carboxylic Acid tert-Butyl Ester is an intermediate in the synthesis of pyrrole derived anti-cancer Agent.
2. N-Boc-pyrrole was used in the synthesis of 1-(tert-butoxycarbonyl)-1H-pyrrol-2-ylboronic acid by treating with n-BuLi and subsequent reaction with trimethyl borate.It may be used as starting material in the synthesis of the following:tropane drivativesN-boc-2-(4-methoxyphenyl)pyrroleN-boc-pyrrol-2-ylboronic acid

Synthesis Reference(s)

The Journal of Organic Chemistry, 31, p. 764, 1966 DOI: 10.1021/jo01341a027

General Description

N-Boc-pyrrole is an N-protected pyrrole. It undergoes Diels–Alder reaction with enantiomerically pure allene-1,3-dicarboxylates to form endo-adducts with retention in configurations at two newly generated stereogenic centers. It also undergoes cyclopropanation with methyl phenyldiazoacetate to form both monocyclopropane and dicyclopropane. Its Ir-catalyzed C-H borylation followed by cross coupling with 3-chlorothiophene to form biheterocycle has been reported.

InChI:InChI=1/C9H13NO2/c1-9(2,3)12-8(11)10-6-4-5-7-10/h4-7H,1-3H3

Upstream product

• 696-62-8 para-iodoanisole 
• 172282-33-6 N-(tert-butoxycarbonyl)-2-(trimethylstannyl)pyrrole 
• 163332-59-0 (3-Methoxy-cyclohex-1-enesulfonyl)-benzene 
• 160732-46-7 endo-2-(p-tolyl-sulfone)-7-tert-butoxycarbonyl-7-azabicyclo<2.2.1>hepta-2,5-diene 
• 114221-05-5 dimethyl 7-(tert-butyloxycarbonyl)-7-azabicyclo<2.2.1.>-hepta-2,5-diene-2,3-dicarboxylate 
• 934-16-7 phenylhydroxamoyl chloride 
• 82912-39-8 N-(t-Butoxycarbonyl)-2,3-bis-7-azabicyclo<2.2.1>hepta-2,5-diene 

Downstream Products

• 219700-34-2 (1S,2R,3E,4R)-(-)-(l)-menthyl 7-tert-butoxycarbonyl-3-[2'-(l)-menthyloxy-2'-oxoethylidene]-7-azabicyclo[2.2.1]hept-5-ene-2-carboxylate 
• 887401-28-7 2-(4-bromo-benzenesulfonyl)-7-aza-bicyclo[2.2.1]hept-2-ene-7-carboxylic acid tert-butyl ester 
• 887401-30-1 2-(4-hexyl-benzenesulfonyl)-7-aza-bicyclo[2.2.1]hept-2-ene-7-carboxylic acid tert-butyl ester 

Relevant articles and documents

Azabicyclic vinyl sulfones for residue-specific dual protein labelling

We have developed [2.2.1]azabicyclic vinyl sulfone reagents that simultaneously enable cysteine-selective protein modification and introduce a handle for further bioorthogonal ligation. The reaction is fast and selective for cysteine relative to other amino acids that have nucleophilic side-chains, and the formed products are stable in human plasma and are moderately resistant to retro Diels-Alder degradation reactions. A model biotinylated [2.2.1]azabicyclic vinyl sulfone reagent was shown to efficiently label two cysteine-tagged proteins, ubiquitin and C2Am, under mild conditions (1-5 equiv. of reagent in NaPi pH 7.0, room temperature, 30 min). The resulting thioether-linked conjugates were stable and retained the native activity of the proteins. Finally, the dienophile present in the azabicyclic moiety on a functionalised C2Am protein could be fluorescently labelled through an inverse electron demand Diels-Alder reaction in cells to allow selective apoptosis imaging. The combined advantages of directness, site-specificity and easy preparation mean [2.2.1]azabicyclic vinyl sulfones can be used for residue-specific dual protein labelling/construction strategies with minimal perturbation of native function based simply on the attachment of an [2.2.1]azabicyclic moiety to cysteine.

Synthesis and spectroscopic characterisation of BODIPY based fluorescent off-on indicators with low affinity for calcium

Two fluorescent off-on Ca2+ indicators based on APTRA (o-aminophenol-N,N-triacetic acid) as low-affinity ligand for Ca2+ and BODIPY (4,4-difluoro-4-bora-3a,4a-diaza-s-indacene) as a fluorophore were synthesized. The new BODIPY-APTRA

Synthesis and Chemistry of N-Oxygenated Pyrroles: Crystal and Molecular Structure of a Highly Stable N-Hydroxypyrrole 18-Crown Ether Hydrate

N-Oxygenated succimides 5-8, 13, and 14, N-oxydithiosuccinimides 10 and 11, and N-oxygenated pyrroles 12, 30a,e, 38, and 39 were synthesized as possible precursors of a pyrrole nitroxide crown ether.N-Methoxypyrrole dithiocrown ethers 21 and 23-27 were pr