4103-11-1

Basic information

• Product Name: (1E)-1-bromocyclooctene
• Synonyms: 1-Bromo-1-cyclooctene; Cyclooctene, 1-bromo-
• CAS NO: 4103-11-1
• Molecular Formula: C₈H₁₃Br
• Molecular Weight: 189.0928
• Mol File: 4103-11-1.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 212.1°C at 760 mmHg
• Flash Point: 83.5°C
• Density: 1.281g/cm³
• Vapor Pressure: 0.256mmHg at 25°C
• Refractive Index: 1.511
• CAS DataBase Reference: (1E)-1-bromocyclooctene(CAS DataBase Reference)
• NIST Chemistry Reference: (1E)-1-bromocyclooctene(4103-11-1)
• EPA Substance Registry System: (1E)-1-bromocyclooctene(4103-11-1)

Safety Data

• Hazardous Substances Data: 4103-11-1(Hazardous Substances Data)

Usage

General Description

(1E)-1-bromocyclooctene is a chemical compound with the molecular formula C8H13Br. It is a colorless liquid that is insoluble in water but soluble in organic solvents. (1E)-1-bromocyclooctene is commonly used in organic synthesis as a reagent for various chemical reactions, including the preparation of other organic compounds. It is also used as a starting material in the production of pharmaceuticals, agrochemicals, and other fine chemicals. The presence of the bromine atom in the molecule makes it a versatile building block for the synthesis of complex organic molecules. Additionally, (1E)-1-bromocyclooctene is also used in research and development laboratories for its unique reactivity and its ability to undergo a variety of chemical transformations. Overall, (1E)-1-bromocyclooctene is a valuable chemical compound with wide-ranging applications in the field of organic chemistry.

Upstream product

• 29974-69-4 trans-1,2- dibromocyclooctane 
• 29974-69-4 trans-1,2-dibromocyclooctane 
• 502-49-8 cycloactanone 
• 931-88-4 1,2-cyclooctene 
• 67-64-1 acetone 
• 931-88-4 cis-Cyclooctene 
• 29974-69-4 1,2-dibromocyclooctane 

Downstream Products

• 505-48-6 octane-1,8-dioic acid 
• 68629-76-5 5,6,7,8,9,10-Hexahydro-1,4-diphenylcycloocta<1,2-d>pyridazin 
• 15922-51-7 1-benzyl-4,5,6,7,8,9-hexahydro-1H-cycloocta[d][1,2,3]triazole 
• 448211-45-8 2-(cyclooct-1-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 1781-78-8 cyclooctyne 
• 6038-12-6 cyclooctene-1-carboxaldehyde 
• 18208-81-6 1,2,3,4-tetraphenyl-5,6,7,8,9,10-hexahydrobenzocyclooctene 
• 4103-09-7 Cyclooct-1-encarbonsaeure 
• 52113-70-9 cyclooct-1-enyl-diphenyl-methanol 

Relevant articles and documents

Reactions of Sodium Diisopropylamide: Liquid-Phase and Solid-Liquid Phase-Transfer Catalysis by N, N, N′, N″, N″-Pentamethyldiethylenetriamine

Sodium diisopropylamide (NaDA) in N,N-dimethylethylamine (DMEA) and DMEA-hydrocarbon mixtures with added N,N,N′,N″,N″-pentamethyldiethylenetriamine (PMDTA) reacts with alkyl halides, epoxides, hydrazones, arenes, alkenes, and allyl ethers. Comparisons of PMDTA with N,N,N′,N′-tetramethylethylenediamine (TMEDA) accompanied by detailed rate and computational studies reveal the importance of the trifunctionality and κ2-κ3 hemilability. Rate studies show exclusively monomer-based reactions of 2-bromooctane, cyclooctene oxide, and dimethylresorcinol. Catalysis with 10 mol % PMDTA shows up to >30-fold accelerations (kcat > 300) with no evidence of inhibition over 10 turnovers. Solid-liquid phase-transfer catalysis (SLPTC) is explored as a means to optimize the catalysis as well as explore the merits of heterogeneous reaction conditions.

Electronic effects versus distortion energies during strain-promoted alkyne-azide cycloadditions: A theoretical tool to predict reaction kinetics

Second-order reaction kinetics of known strain-promoted azide-alkyne cycloaddition (SPAAC) reactions were compared with theoretical data from a range of ab initio methods. This produced both detailed insights into the factors determining the reaction rates and two straightforward theoretical tools that can be used to predict a priori the reaction kinetics of novel cyclooctynes for strain-promoted cycloaddition reactions. Multiple structural and electronic effects contribute to the reactivity of various cyclooctynes. It is therefore hard to relate a physical or electronic property directly and independently to the reactivity of the cyclooctyne. However, we show that Hartree-Fock LUMO energies, which were acquired while calculating activation energies at the MP2 level of theory, correlate with second-order kinetic rate data and are therefore usable for reactivity predictions of cyclooctynes towards azides. Using this correlation, we developed a simple theoretical tool that can be used to predict the reaction kinetics of (novel) cyclooctynes for SPAAC reactions. Activation energies, distortion energies, and TS conformational data were compared in a set of strained cyclooctynes in strain-promoted azide-alkyne cycloaddition (SPAAC) reactions. Only electronic effects could be accurately related to experimental rate data. Copyright

Clicking 1,2,4,5-tetrazine and cyclooctynes with tunable reaction rates

Substituted tetrazines have been found to undergo facile inverse electron demand Diels-Alder reactions with "tunable" reaction rates.