33718-99-9

Basic information

• Product Name: (2Z)-2-bromobut-2-enal
• Synonyms: (2Z)-2-Bromo-2-butenal; 2-butenal, 2-bromo-, (2Z)-
• CAS NO: 33718-99-9
• Molecular Formula: C₄H₅BrO
• Molecular Weight: 148.9859
• Mol File: 33718-99-9.mol
• Article Data: 13

Chemical Properties

• Boiling Point: 173.6°C at 760 mmHg
• Flash Point: 92.1°C
• Density: 1.512g/cm³
• Vapor Pressure: 1.26mmHg at 25°C
• Refractive Index: 1.488
• CAS DataBase Reference: (2Z)-2-bromobut-2-enal(CAS DataBase Reference)
• NIST Chemistry Reference: (2Z)-2-bromobut-2-enal(33718-99-9)
• EPA Substance Registry System: (2Z)-2-bromobut-2-enal(33718-99-9)

Safety Data

• Hazardous Substances Data: 33718-99-9(Hazardous Substances Data)

Usage

Description

(2Z)-2-bromobut-2-enal is a chemical compound belonging to the aldehyde class, characterized by the presence of a bromine atom and a double bond in its molecular structure. It is known for its strong and pungent odor.

Uses

Used in Organic Synthesis:
(2Z)-2-bromobut-2-enal is used as an intermediate in the production of various pharmaceuticals and agrochemicals, contributing to the synthesis of complex organic molecules.
Used in Fragrance and Perfume Industry:
(2Z)-2-bromobut-2-enal is used as a component in the formulation of fragrances and perfumes due to its strong and pungent odor, adding a unique sensory experience to these products.
Used in Flavor and Aroma Compounds Industry:
(2Z)-2-bromobut-2-enal is utilized in the creation of various flavors and aroma compounds, enhancing the sensory profile of consumer products.
Caution:
(2Z)-2-bromobut-2-enal should be handled with care as it is toxic when inhaled, causing irritation to the respiratory system and eyes.

Upstream product

• 123-73-9 crotonaldehyde 
• 15798-64-8 cis-crotonaldehyde 
• 98551-14-5 (Z)-2-bromo-1,1-diethoxy-2-butene 
• 123-73-9 trans-Crotonaldehyde 
• 83769-15-7 (2-Bromo-3,3-dihydroxy-1-methyl-propyl)-dimethyl-sulfonium; bromide 
• 50553-14-5 2,3-dibromo-butyraldehyde 
• 74322-77-3 trans-1-Morpholinobutadien 

Downstream Products

• 1337979-21-1 (Z)-4-bromo-1-phenylhex-4-en-1-yn-3-ol 
• 52467-65-9 (Z)-2-bromobut-2-en-1-ol 
• 2591-86-8 N-Formylpiperidine 
• 52900-92-2 2-Piperidinobut-2-enal 
• 52900-93-3 E-2-Piperidino-2-butenal 
• 22039-42-5 1,2-dipiperidino-ethene 

Relevant articles and documents

Catalytic Enantioselective [2+2] Cycloaddition of α-Halo Acroleins: Construction of Cyclobutanes Containing Two Tetrasubstituted Stereocenters

A catalytic enantioselective formal [2+2] cycloaddition between α-halo acroleins and electronically diverse arylalkenes is described. In the presence of (S)-oxazaborolidinium cation as the catalyst, densely functionalized cyclobutanes containing two vicin

Syntheses of strychnine, norfluorocurarine, dehydrodesacetylretuline, and valparicine enabled by intramolecular cycloadditions of Zincke aldehydes

A full account of the development of the base-mediated intramolecular Diels-Alder cycloadditions of tryptamine-derived Zincke aldehydes is described. This important complexity-generating transformation provides the tetracyclic core of many indole monoterpene alkaloids in only three steps from commercially available starting materials and played a key role in short syntheses of norfluorocurarine (five steps), dehydrodesacetylretuline (six steps), valparicine (seven steps), and strychnine (six steps). Reasonable mechanistic possibilities for this reaction, a surprisingly facile dimerization of the products, and an unexpected cycloreversion to regenerate Zincke aldehydes under specific conditions are also discussed.

Preparation of α-haloacrylate derivatives via dimethyl sulfoxide-mediated selective dehydrohalogenation

(Chemical Equation Presented) Dimethyl sulfoxide causes α/β-dihalopropanoate derivatives to undergo efficient, selective dehydrohalogenation to form α-haloacrylate analogues. A variety of α-halo Michael acceptors were prepared in dimethyl sulfoxide under mild, base-free conditions, including the preparation of α-bromoacrolein and α-chloro- and bromoacrylonitriles. Synthesis of these molecules has been reported in the literature to be difficult. Among all the existing dehydrohalogenation procedures, this protocol is the most facile, practical, and environmentally benign process.