87630-40-8

Basic information

• Product Name: 3-BROMO-1H-PYRROLE
• Synonyms: 3-BROMO-1H-PYRROLE;1H-Pyrrole,3-bromo-(9CI);3-Bromopyrrole;EOS-61579
• CAS NO: 87630-40-8
• Molecular Formula: C₄H₄BrN
• Molecular Weight: 145.99
• Product Categories: HALIDE;Benzenes
• Mol File: 87630-40-8.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 210.837 °C at 760 mmHg
• Flash Point: 81.312 °C
• Appearance: /
• Density: 1.739 g/cm³
• Vapor Pressure: 0.273mmHg at 25°C
• Refractive Index: 1.591
• PKA: 15.33±0.50(Predicted)
• CAS DataBase Reference: 3-BROMO-1H-PYRROLE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-BROMO-1H-PYRROLE(87630-40-8)
• EPA Substance Registry System: 3-BROMO-1H-PYRROLE(87630-40-8)

Safety Data

• Hazardous Substances Data: 87630-40-8(Hazardous Substances Data)

Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 49, p. 3239, 1984 DOI: 10.1021/jo00191a047Tetrahedron Letters, 24, p. 3455, 1983 DOI: 10.1016/S0040-4039(00)86011-6

InChI:InChI=1/C4H4BrN/c5-4-1-2-6-3-4/h1-3,6H

Upstream product

• 87630-36-2 3-bromo-1-triisopropylsilanyl-1H-pyrrole 
• 429-41-4 tetrabutyl ammonium fluoride 

Downstream Products

• 18159-13-2 1-benzyl-3-bromo-1H-pyrrole 
• 1071444-90-0 C₂₃H₂₀N₂O₃ 
• 1403230-02-3 N-nosyl-3-bromo-pyrrole 
• 214360-77-7 3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrrole 
• 172100-29-7 3-bromo-1H-pyrrol-1-amine 

Relevant articles and documents

Metal-Free Directed C?H Borylation of Pyrroles

Robust strategies to enable the rapid construction of complex organoboronates in selective, practical, low-cost, and environmentally friendly modes remain conspicuously underdeveloped. Here, we develop a general strategy for the site-selective C?H borylation of pyrroles by using only BBr3 directed by pivaloyl groups, avoiding the use of any metal. The site-selectivity is generally dominated by chelation and electronic effects, thus forming diverse C2-borylated pyrroles against the steric effect. The formed products can readily engage in downstream transformations, enabling a step-economic process to access drugs such as Lipitor. DFT calculations (wB97X-D) demonstrate the preferred positional selectivity of this reaction.

Silylpyrrole Oxidation En Route to Saxitoxin Congeners including 11-Saxitoxinethanoic Acid

Saxitoxin (STX) is the archetype of a large family (>50) of architecturally distinct, bisguanidinium natural products. Among this collection of isolates, two members, 11-saxitoxinethanoic acid (11-SEA) and zetekitoxin AB (ZTX), are unique, bearing carbon substitution at C11. A desire to efficiently access these compounds has motivated the development of new tactical approaches to a late-stage C11-ketone intermediate 26, designed to enable C–C bond formation using any one of a number of possible reaction technologies. Highlights of the synthesis of 26 include a metal-free, silylpyrrole oxidative dearomatization reaction and a vinylsilane epoxidation–rearrangement cascade to generate the requisite ketone. Nucleophilic addition to 26 makes possible the preparation of unnatural C11-substituted STXs. Olefination of this ketone is also demonstrated and, when followed by a redox-neutral isomerization reaction, affords 11-SEA.

SIP3 antagonists

The present invention relates to antagonists of the S1P3 receptor formula (A) as herein described and pharmaceutical compositions thereof. The compounds of formula (A) are useful in the preparation of a medicament, in particular for the treatment of Alzheimer's disease.