33718-99-9

Usage

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

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

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

Sequential O-Arylation/Lanthanide(III)-Catalyzed [3,3]-Sigmatropic Rearrangement of Bromo-Substituted Allylic Alcohols

Lanthanide(III)-catalyzed aryl-Claisen rearrangement of substrates bearing halo-substituted allyl groups, specifically 2-bromoallyl aryl ethers, afford ortho -2-bromoallylphenols. Aryl ether substrates were synthesized from brominated allylic alcohols via Mitsunobu reaction, Cu(II)-catalyzed arylation using potassium aryltrifluoroborate salts, or S N Ar reaction. Aryl-Claisen rearrangements proceeded in moderate to excellent yields using Eu(III) catalysis. The alkenylbromide functionality remains intact, illustrating the compatibility of synthetically important alkenylhalides during C-O/C-C σ-bond migration processes. Subsequent derivatization of the ortho -2-bromoallylphenol products through O-alkylation or C-arylation/alkenylation via Suzuki-Miyaura cross-coupling demonstrate the potential to access densely-functionalized molecules.

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.

Enantioselective Diels-Alder reaction of α-(acylthio)acroleins: A new entry to sulfur-containing chiral quaternary carbons

A catalytic and enantioselective Diels-Alder reaction of α-(carbamoylthio)acroleins induced by an organoammonium salt of chiral triamine is described. α-(Carbamoylthio)acroleins are designed and synthesized as new sulfur-containing dienophiles for the fir

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.

Regioselective synthesis of acyclic cis-enediynes via an acid-catalyzed rearrangement of 1,2-dialkynylallyl alcohols. Syntheses, computational calculations, and mechanism

A novel synthesis of acyclic cis-enediynes 2 has been established by an acid-catalyzed rearrangement of 1,2-diyn-2-propen-1-ols 1 possessing a C3- aryl group in the presence of water, alcohols, or thiols. Reactivity of allyl alcohols and regio- and cis/trans diastereoselectivity of the allylic migration were examined. In the presence of (±)-10-camphorsulfonic acid (CSA), the parent allyl alcohol 5 and the C3-methyl-substituted 9 failed to give enediynes, whereas the C3-aryl-substituted 12 and 29 underwent the allylic rearrangement to provide predominantly cis-enediynes 16 and 31 at room temperature or below. Under similar acidic conditions, enediyne alcohol 13 produced 16b and 16d with the same regio- and cis/trans diastereoselectivity observed for 12. Allyl alcohol 30, an isomer of 29, also provided enediynes 31c and 32c after a prolonged reaction (90 h) at room temperature in the presence of CSA and EtOH. These results suggested that the same allylic cations were obtained from allyl alcohols 12 and 13 or 29 and 30 even though the ease of ionization differed for each substrate. Involvement of allylic cations in the product-forming step was confirmed by the finding that chiral allyl alcohols (-)-12 and (-)-18c furnished racemic products. In general, the p-MeOPh-substituted allyl alcohol 29 gave a better regioselectivity than the Ph-substituted 12. In the reactions with alcohols, the regioisomeric ratios were 100:0 (31:33) for 29 and ca. 96:4 (16:17) for 12; the ratios decreased to ca. 90:10 (31:33) for 29 and ca. 70:30 (16:17) for 12 when thiols were used. The cis/trans diastereoselectivity is higher for allyl alcohol 12 (100% for 16 at 20°C) compared to that for 29 (31:32 = 80:20-94:6 at 0°C). Computational calculations at the RHF/3-21G level, carried out on the model compounds and allylic cations, indicated that nucleophilic trapping takes place preferentially at the C3 carbon to form the thermodynamically much more stable enediynes. Under the best reaction conditions (1 equiv of CSA and 2 equiv of EtOH in CH2Cl2, 20°C), a number of acyclic cis-enediynes can be synthesized in three steps from the commercially available α-bromocinnamaldehyde (10).

Studies towards total synthesis of antillatoxin: Investigation of the indium-mediated allylation reactions of carbonyl compounds with β-bromocrotylbromide in water

Indium mediates the coupling of β-bromocrotylbromide with carbonyl compounds in saturated ammonium chloride in the presence of lanthanide triflate under sonication to give the corresponding compounds in good yield and moderate to high syn diastereoselecti

Synthese regioselective par voie organometallique de vinylsilanes fonctionnels a partir de derives carbonyles α-ethyleniques α-trimethylsilyles

The α-trimethylsilyl conjugated carbonyl derivatives 1 easily react with organometallics 2 (M = Al, Mg, Zn) and allow preparation of functional vinylsilanes 3 or 4, in regioselective manner: R'-CH C(SiMe3)-C(OH)(R')(R) 3; (R')(R)CH-C(SiMe3)C(R')(OSiMe3) 4.

Formation of acetylenic acetals by ring opening of 1,1,2-trihalocyclopropanes under phase-transfer conditions

A number of substituted 1,1-dibromo- and 1,1-dichlorocyclopropanes with an additional chlorine or bromine atom attached to C-2 were synthesized in reasonabk to good yields by dihalocarbene addition to the corresponding alkenes under phase-transfer conditions. When the trihalides were treated with 50% aqueous sodium hydroxide in the presence of ethanol. triethylbenzylammonium chloride and dichloromethane. most of the compounds underwent ring opening and afforded mixtures of acetylenic acetals, usually in good yields. The reaction most likely involves cyclopropene intermediates, which in some cases also rearrange to a minor extent to the corresponding vinylcarbenes and afford α,β-unsaturated aldehydes. Acta Chemica Scandinavica 1996.

New Enantioselective Syntheses of Acetylenic Alcohols Using Functionalized Diorganozincs

Two new enantioselective preparations of polyfunctional propargylic alcohols (82 to >96 percent ee) have been developed.They were obtained by using the addition of functionalized dialkylzincs to acetylenic aldehydes in the presence of a 1:1 mixture of Ti(