1037088-26-8

Basic information

• Product Name: 1-allyl-4-bromo-2-methylbenzene
• Synonyms: 1-allyl-4-bromo-2-methylbenzene
• CAS NO: 1037088-26-8
• Molecular Weight: 211.101
• Mol File: 1037088-26-8.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: 1-allyl-4-bromo-2-methylbenzene(CAS DataBase Reference)
• NIST Chemistry Reference: 1-allyl-4-bromo-2-methylbenzene(1037088-26-8)
• EPA Substance Registry System: 1-allyl-4-bromo-2-methylbenzene(1037088-26-8)

Safety Data

• Hazardous Substances Data: 1037088-26-8(Hazardous Substances Data)

Usage

Physical state

Colorless to light yellow liquid

Odor

Strong, aromatic

Uses

Intermediate in the synthesis of pharmaceuticals, agrochemicals, and other organic compounds; production of fragrances and flavors

Reactivity

Highly reactive

Safety precautions

Causes skin and eye irritation; harmful if ingested or inhaled

Storage

Cool, dry place away from direct sunlight and sources of ignition

Upstream product

• 116632-39-4 2-methyl-4-bromoiodobenzene 
• 106-95-6 allyl bromide 

Downstream Products

• 853796-39-1 2-(4-bromo-2-methyl-phenyl)acetic acid 
• 1037082-19-1 (R)-(4-(1-((tert-butyldimethylsilyl)oxy)propan-2-yl)-3-methylphenyl)boronic acid 
• 1037082-18-0 (R)-(2-(4-bromo-2-methylphenyl)propoxy)(tert-butyl)dimethylsilane 
• 1037082-12-4 (R)-2-(4-bromo-2-methylphenyl)propan-1-ol 

Relevant articles and documents

Atropisomer Control in Macrocyclic Factor VIIa Inhibitors

Incorporation of a methyl group onto a macrocyclic FVIIa inhibitor improves potency 10-fold but is accompanied by atropisomerism due to restricted bond rotation in the macrocyclic structure, as demonstrated by NMR studies. We designed a conformational constraint favoring the desired atropisomer in which this methyl group interacts with the S2 pocket of FVIIa. A macrocyclic inhibitor incorporating this constraint was prepared and demonstrated by NMR to reside predominantly in the desired conformation. This modification improved potency 180-fold relative to the unsubstituted, racemic macrocycle and improved selectivity. An X-ray crystal structure of a closely related analogue in the FVIIa active site was obtained and matches the NMR and modeled conformations, confirming that this conformational constraint does indeed direct the methyl group into the S2 pocket as designed. The resulting rationally designed, conformationally stable template enables further optimization of these macrocyclic inhibitors.