79413-93-7

Basic information

• Product Name: (R)-4-BROMO-1,2-EPOXYBUTANE
• Synonyms: (R)-4-BROMO-1,2-EPOXYBUTANE;OXIRANE, (2-BROMOETHYL)-,(R)
• CAS NO: 79413-93-7
• Molecular Formula: C₄H₇BrO
• Molecular Weight: 151
• Mol File: 79413-93-7.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (R)-4-BROMO-1,2-EPOXYBUTANE(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-4-BROMO-1,2-EPOXYBUTANE(79413-93-7)
• EPA Substance Registry System: (R)-4-BROMO-1,2-EPOXYBUTANE(79413-93-7)

Safety Data

• Hazardous Substances Data: 79413-93-7(Hazardous Substances Data)

Usage

General Description

The chemical (R)-4-Bromo-1,2-epoxybutane is a colorless liquid that is used in organic synthesis and as a building block for the production of pharmaceuticals and agrochemicals. It is a chiral epoxide, meaning it has a specific orientation of its atoms in space. (R)-4-BROMO-1,2-EPOXYBUTANE is primarily used as a reagent in organic chemistry reactions, particularly in the synthesis of chiral compounds. It is important to handle this chemical with care, as it is toxic and may cause allergic skin reactions. Additionally, it should only be used in a well-ventilated area and with proper protective equipment.

Upstream product

• 70681-41-3 (R)-dimethyl malate 
• 64028-90-6 (S)-1,4-dibromo-2-butanol 
• 13287-42-8 (2-bromoethyl)oxirane 

Downstream Products

• 674483-18-2 (R)-8-acenaphthen-1-yl-1-(4-fluorophenyl)-3-(2-(R)-oxiranyl-ethyl)-1,3,8-triazaspiro[4.5]decan-4-one 
• 794466-70-9 (3R)-1-{(1R,2R)-2-[2-(3,4-dimethoxyphenyl)ethoxy]cyclohexyl}pyrrolidin-3-ol 

Relevant articles and documents

Predictable stereoselective and chemoselective hydroxylations and epoxidations with P450 3A4

Enantioselective hydroxylation of one specific methylene in the presence of many similar groups is debatably the most challenging chemical transformation. Although chemists have recently made progress toward the hydroxylation of inactivated C-H bonds, enzymes such as P450s (CYPs) remain unsurpassed in specificity and scope. The substrate promiscuity of many P450s is desirable for synthetic applications; however, the inability to predict the products of these enzymatic reactions is impeding advancement. We demonstrate here the utility of a chemical auxiliary to control the selectivity of CYP3A4 reactions. When linked to substrates, inexpensive, achiral theobromine directs the reaction to produce hydroxylation or epoxidation at the fourth carbon from the auxiliary with pro-R facial selectivity. This strategy provides a versatile yet controllable system for regio-, chemo-, and stereoselective oxidations at inactivated C-H bonds and demonstrates the utility of chemical auxiliaries to mediate the activity of highly promiscuous enzymes.

Synthesis of optically active 2-methyl- and 2-ethyl-1,6-dioxaspiro[4.4]nonane- and -[4.5]decane pheromones from a common chiral precursor

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