54804-44-3

Basic information

• Product Name: 3-(Bromomethyl)isoquinoline
• Synonyms: 3-(Bromomethyl)isoquinoline;3-Bromomethyl-2-benzazine
• CAS NO: 54804-44-3
• Molecular Formula: C₁₀H₈BrN
• Molecular Weight: 222.08122
• Mol File: 54804-44-3.mol
• Article Data: 5

Chemical Properties

• Melting Point: 270-325 °C (decomp)
• Boiling Point: 322.147 °C at 760 mmHg
• Flash Point: 148.629 °C
• Appearance: /
• Density: 1.518 g/cm³
• Vapor Pressure: 0.000536mmHg at 25°C
• Refractive Index: 1.673
• PKA: 3.85±0.30(Predicted)
• CAS DataBase Reference: 3-(Bromomethyl)isoquinoline(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(Bromomethyl)isoquinoline(54804-44-3)
• EPA Substance Registry System: 3-(Bromomethyl)isoquinoline(54804-44-3)

Safety Data

• Hazardous Substances Data: 54804-44-3(Hazardous Substances Data)

Usage

General Description

3-(Bromomethyl)isoquinoline is a chemical compound that consists of an isoquinoline ring with a bromomethyl group attached at the third position. It is a colorless to yellow crystalline solid that is mainly used in organic synthesis and pharmaceutical research. Its bromomethyl group makes it a useful intermediate in the production of various pharmaceuticals and agrochemicals. 3-(Bromomethyl)isoquinoline is also a precursor in the synthesis of complex organic molecules and can be used as a building block in the creation of novel drug compounds. It is important to handle and use this chemical with caution, as it may pose hazards if not handled properly.

InChI:InChI=1/C10H8BrN/c11-6-10-5-8-3-1-2-4-9(8)7-12-10/h1-5,7H,6H2

Upstream product

• 1125-80-0 3-methylisoquinoline 
• 76884-34-9 3-Hydroxymethylisoquinoline 
• 5470-80-4 3-formylisoquinoline 

Downstream Products

• 72033-13-7 2-(isoquinolin-3-yl)acetic acid 
• 76884-34-9 3-Hydroxymethylisoquinoline 

Relevant articles and documents

Palladium-Catalyzed Isoquinoline Synthesis by Tandem C-H Allylation and Oxidative Cyclization of Benzylamines with Allyl Acetate

A novel approach to synthesize 3-methylisoquinolines via a one-pot, two-step, palladium(II)-catalyzed tandem C-H allylation/intermolecular amination and aromatization is reported. A wide series of 3-methylisoquinoline derivatives were obtained directly using this method in moderate to good yields, and we highlight the synthetic importance of this new transformation.

Design, syntheses, and pharmacological characterization of 17-cyclopropylmethyl-3,14β-dihydroxy-4,5α-epoxy-6α-(isoquinoline-3′-carboxamido)morphinan analogues as opioid receptor ligands

A series of 17-cyclopropylmethyl-3,14β-dihydroxy-4,5α-epoxy-6α-(isoquinoline-3′-carboxamido)morphinan (NAQ) analogues were synthesized and pharmacologically characterized to study their structure-activity relationship at the mu opioid receptor (MOR). The competition binding assay showed two-atom spacer and aromatic side chain were optimal for MOR selectivity. Meanwhile, substitutions at the 1′- and/or 4′-position of the isoquinoline ring retained or improved MOR selectivity over the kappa opioid receptor while still possessing above 20-fold MOR selectivity over the delta opioid receptor. In contrast, substitutions at the 6′- and/or 7′-position of the isoquinoline ring reduced MOR selectivity as well as MOR efficacy. Among this series of ligands, compound 11 acted as an antagonist when challenged with morphine in warm-water tail immersion assay and produced less significant withdrawal symptoms compared to naltrexone in morphine-pelleted mice. Compound 11 also antagonized the intracellular Ca2+ increase induced by DAMGO. Molecular dynamics simulation studies of 11 in three opioid receptors indicated orientation of the 6′-nitro group varied significantly in the different 'address' domains of the receptors and played a crucial role in the observed binding affinities and selectivity. Collectively, the current findings provide valuable insights for future development of NAQ-based MOR selective ligands.

Synthesis and SAR of novel isoquinoline CXCR4 antagonists with potent anti-HIV activity

Using AMD070 as a starting point for structural modification, a novel series of isoquinoline CXCR4 antagonists was developed. A structure-activity scan of alternate lower heterocycles led to the 3-isoquinolinyl moiety as an attractive replacement for benzimidazole. Side chain optimization in the isoquinoline series led to a number of compounds with low nanomolar anti-HIV activities and promising rat PK properties.