4773-87-9

Basic information

• Product Name: 3-bromo-2,4-dimethylpenta-1,3-diene
• CAS NO: 4773-87-9
• Molecular Formula: C₇H₁₁Br
• Molecular Weight: 175.0662
• Mol File: 4773-87-9.mol
• Article Data: 14

Chemical Properties

• Boiling Point: 175.7°C at 760 mmHg
• Flash Point: 70.2°C
• Density: 1.204g/cm³
• Vapor Pressure: 1.52mmHg at 25°C
• Refractive Index: 1.483
• CAS DataBase Reference: 3-bromo-2,4-dimethylpenta-1,3-diene(CAS DataBase Reference)
• NIST Chemistry Reference: 3-bromo-2,4-dimethylpenta-1,3-diene(4773-87-9)
• EPA Substance Registry System: 3-bromo-2,4-dimethylpenta-1,3-diene(4773-87-9)

Safety Data

• Hazardous Substances Data: 4773-87-9(Hazardous Substances Data)

Upstream product

• 110-00-9 furan 
• 22715-57-7 2,2,3,3-tetramethyl-1,1-dibromocyclopropane 
• 563-79-1 2,3-Dimethyl-2-butene 
• 75-25-2 Bromoform 
• 55531-95-8 2,3-dimethyl-1,4-bis(trimethylsilyl)-2-butene 

Downstream Products

• 1350704-12-9 C₁₆H₂₆O 
• 1442555-59-0 C₂₂H₃₄O 
• 1442555-60-3 C₂₂H₄₀OSi 
• 1442555-61-4 C₁₉H₃₄OSi 
• 1442555-62-5 C₁₆H₂₄O 
• 155588-13-9 (2aR,4S,4aS,6R,11S,12S,12aR,12bS)-12-benzoyloxy-11-hydroxy-4a,8,13,13-tetramethyl-5-oxo-4-triethylsilyloxy-3,4,4a,5,6,9,10,11,12,12a-decahydro-1H-7,11-methanocyclodeca[3,4]benzo[1,2-b]oxete-6,12b(2aH)diyl diacetate 
• 155588-14-0 13-deoxybaccatin III 

Relevant articles and documents

Two-Phase Synthesis of Taxol

Taxol (a brand name for paclitaxel) is widely regarded as among the most famed natural isolates ever discovered, and has been the subject of innumerable studies in both basic and applied science. Its documented success as an anticancer agent, coupled with early concerns over supply, stimulated a furious worldwide effort from chemists to provide a solution for its preparation through total synthesis. Those pioneering studies proved the feasibility of retrosynthetically guided access to synthetic Taxol, albeit in minute quantities and with enormous effort. In practice, all medicinal chemistry efforts and eventual commercialization have relied upon natural (plant material) or biosynthetically derived (synthetic biology) supplies. Here we show how a complementary divergent synthetic approach that is holistically patterned off of biosynthetic machinery for terpene synthesis can be used to arrive at Taxol.

Total synthesis of taxane terpenes: Cyclase phase Dedicated to Professor Melanie S. Sanford on the occasion of her receipt of the Tetrahedron Young Investigator Award

A full account of synthetic efforts toward a lowly oxidized taxane framework is presented. A non-natural taxane, dubbed 'taxadienone', was synthesized as our first entry into the taxane family of diterpenes. The final synthetic sequence illustrates a seven-step, gram-scale, and enantioselective route to this tricyclic compound in 18% overall yield. This product was then modified further to give (+)-taxadiene, the lowest oxidized member of the taxane family of natural products.

Scalable enantioselective total synthesis of taxanes

Taxanes form a large family of terpenes comprising over 350 members, the most famous of which is Taxol (paclitaxel), a billion-dollar anticancer drug. Here, we describe the first practical and scalable synthetic entry to these natural products via a concise preparation of (+)-taxa-4(5),11(12)-dien-2-one, which has a suitable functional handle with which to access more oxidized members of its family. This route enables a gram-scale preparation of the 'parent' taxane-taxadiene-which is the largest quantity of this naturally occurring terpene ever isolated or prepared in pure form. The characteristic 6-8-6 tricyclic system of the taxane family, containing a bridgehead alkene, is forged via a vicinal difunctionalization/Diels-Alder strategy. Asymmetry is introduced by means of an enantioselective conjugate addition that forms an all-carbon quaternary centre, from which all other stereocentres are fixed through substrate control. This study lays a critical foundation for a planned access to minimally oxidized taxane analogues and a scalable laboratory preparation of Taxol itself.