18719-27-2

Basic information

• Product Name: 3-Pentynyl bromide
• Synonyms: 3-Pentynyl bromide;5-BroMo-2-pentyne
• CAS NO: 18719-27-2
• Molecular Formula: C₅H₇Br
• Molecular Weight: 147.01308
• Mol File: 18719-27-2.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3-Pentynyl bromide(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Pentynyl bromide(18719-27-2)
• EPA Substance Registry System: 3-Pentynyl bromide(18719-27-2)

Safety Data

• Hazardous Substances Data: 18719-27-2(Hazardous Substances Data)

Upstream product

• 113984-39-7 1,3-Diisopropyl-2-pent-3-ynyl-isourea 
• 3329-88-2 pent-3-yn-1-yl 4-methylbenzenesulfonate 

Downstream Products

• 126459-32-3 (4S)-3-(9-phenylfluoren-9-yl)-4-(1'-oxo-4'-hexynyl)oxazolidine 
• 126459-30-1 (4S)-2-oxo-3-(9-phenylfluoren-9-yl)-4-(1'-oxo-4'-hexynyl)oxazolidine 
• 827575-30-4 4-pent-3-ynyl-1-(toluene-4-sulfonyl)-1,2,3,6-tetrahydropyridine 
• 84654-29-5 5-(bromomethyl)-3-isoxazolecarboxylic acid ethyl ester 
• 79402-23-6 C₁₇H₂₀O₂Se 
• 79402-21-4 2-Pent-2-ynyl-3-phenylselanylmethyl-cyclopentanone 
• 79402-26-9 C₁₇H₂₂O₂Se 
• 79402-25-8 (2RS,3SR)-2-((Z)-2-Penten-1-yl)-3-((phenylselenyl)methyl)cyclopentan-1-one 
• 174226-69-8 (S)-N--o-toluidine 
• 157948-87-3 N-Benzyl-N-(non-8-en-2-ynyl)-N-(pent-3-ynyl)amine 
• 157948-96-4 1-Benzyl-4-((E)-ethylidene)-3-((Z)-hept-6-enylidene)piperidine 

Relevant articles and documents

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The important biochemical probe molecule brefeldin A (1) has served as an inspirational target in the past, but none of the many routes has actually delivered more than just a few milligrams of product, where documented. The approach described herein is clearly more efficient; it hinges upon the first implementation of ruthenium-catalyzed trans-hydrogenation in natural products total synthesis. Because this unorthodox reaction is selective for the triple bond and does not touch the transannular alkene or the lactone site of the cycloalkyne, it outperforms the classical Birch-type reduction that could not be applied at such a late stage. Other key steps en route to 1 comprise an iron-catalyzed reductive formation of a non-terminal alkyne, an asymmetric propiolate carbonyl addition mediated by a bulky amino alcohol, and a macrocyclization by ring-closing alkyne metathesis catalyzed by a molybdenum alkylidyne.

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The present invention relates to the synthesis of ent-progesterone and intermediates thereof.

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Treatment of O-alkylisoureas with trifluoromethanesulphonic acid and a tetrabutylammonium salt (bromide or iodide) affords alkyl halides in high yields.