52370-21-5

Basic information

• Product Name: (E)-2-BROMO-2-BUTEN-1-OL
• Synonyms: (E)-2-BROMO-2-BUTEN-1-OL
• CAS NO: 52370-21-5
• Molecular Formula: C₄H₇BrO
• Molecular Weight: 151
• Mol File: 52370-21-5.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (E)-2-BROMO-2-BUTEN-1-OL(CAS DataBase Reference)
• NIST Chemistry Reference: (E)-2-BROMO-2-BUTEN-1-OL(52370-21-5)
• EPA Substance Registry System: (E)-2-BROMO-2-BUTEN-1-OL(52370-21-5)

Safety Data

• Hazardous Substances Data: 52370-21-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(E)-2-BROMO-2-BUTEN-1-OL is used as a building block for the synthesis of various pharmaceuticals. Its reactivity in different chemical reactions enables the development of a broad range of medicinal compounds.
Used in Agrochemical Industry:
In the agrochemical industry, (E)-2-BROMO-2-BUTEN-1-OL is utilized as an intermediate for the production of agrochemicals. Its unique structure and reactivity contribute to the creation of effective compounds for agricultural applications.
Used in Specialty Chemicals Production:
(E)-2-BROMO-2-BUTEN-1-OL is also used as an intermediate in the synthesis of specialty chemicals. Its versatility in chemical reactions allows for the development of a wide array of specialty products.
Safety Precautions:
It is important to handle (E)-2-BROMO-2-BUTEN-1-OL with care due to its potential hazards, which include skin and eye irritation. It should be used in a well-ventilated environment and proper protective equipment should be worn to ensure safety.

Upstream product

• 51263-38-8 2-bromo-cis-crotonic acid ethyl ester 
• 24247-53-8 2-bromocrotonaldehyde 
• 4021-75-4 2,3-dibromo-1-butanol 
• 33718-99-9 (Z)-2-bromobut-2-enal 
• 17642-18-1 methyl bromo-crotonate 

Downstream Products

• 352354-52-0 N-benzyl-N-[2(E)-2-bromo-2-buten-1-yl]amine 

Relevant articles and documents

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.

New observations in organozinc chemistry: Control of relative stereochemistry in reactions of silicon substituted alkenylzinc reagents

Reagents have been synthesised that behave as both Lewis acids and nucleophiles. Reaction of these reagents with electrophiles has led to the finding that diastereoselectivity is observed upon addition to aldehydes. An ordered transition state to account

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

A new synthesis of indoles

Aryl radical cyclisation onto appropriate vinyl bromides leads to a new route to indoles.