71566-70-6

Basic information

• Product Name: 2,5-Dibromo-1,5-hexadiene
• Synonyms: 2,5-Dibromo-1,5-hexadiene;2,5-dibromohexa-1,5-diene
• CAS NO: 71566-70-6
• Molecular Formula: C6H8Br2
• Molecular Weight: 239.9357
• Mol File: 71566-70-6.mol

Chemical Properties

• Boiling Point: 193.9°Cat760mmHg
• Flash Point: 69°C
• Appearance: /
• Density: 1.669g/cm³
• Vapor Pressure: 0.633mmHg at 25°C
• Refractive Index: 1.53
• CAS DataBase Reference: 2,5-Dibromo-1,5-hexadiene(CAS DataBase Reference)
• NIST Chemistry Reference: 2,5-Dibromo-1,5-hexadiene(71566-70-6)
• EPA Substance Registry System: 2,5-Dibromo-1,5-hexadiene(71566-70-6)

Safety Data

• Hazardous Substances Data: 71566-70-6(Hazardous Substances Data)

Usage

Appearance

Colorless to pale yellow liquid The compound has a pale color and is in a liquid state at room temperature.

Odor

Pungent The compound has a strong, unpleasant smell.

Usage

Reactant in organic synthesis, diene in polymer preparation It is primarily used as a reactant in organic synthesis and as a diene in the preparation of various polymers.

Chemical structure

Six-carbon chain with two bromine atoms and two double bonds The structure consists of a chain with 6 carbon atoms, two bromine atoms attached at the 2nd and 5th positions, and two double bonds between the 1st and 2nd carbon and the 4th and 5th carbon.

Toxicity

Moderately toxic The compound is considered to be moderately toxic and may cause harm upon exposure.

Health hazards

Skin, eye, and respiratory system irritation Exposure to 2,5-Dibromo-1,5-hexadiene may cause irritation to the skin, eyes, and respiratory system.

Storage

Cool, dry, and away from direct sunlight The compound is sensitive to light and air, so it should be stored in a cool, dry place away from direct sunlight to maintain its stability.

InChI:InChI=1/C6H8Br2/c1-5(7)3-4-6(2)8/h1-4H2

Upstream product

• 513-31-5 2-bromoallyl bromide 
• 1730-25-2 allylmagnesium bromide 
• 58443-86-0 1,2,5,6-tetrabromohexane 
• 628-16-0 hexa-1,5-diyne 
• 124080-27-9 2,5-bis(trimethylsilyl)1,5-hexadiene 
• 592-42-7 1,5-Hexadien 
• 87373-49-7 1,4-dibromo-2,3-diazabicyclo<2.2.2>oct-2-ene 

Relevant articles and documents

Synthesis of 2,5-Diaryl-1,5-dienes from Allylic Bromides Using Visible-Light Photoredox Catalysis

Visible-light photoreductive coupling of 2-arylallyl bromides in the presence of the photocatalyst Ru(bpy)3(PF6)2, a Hantzsch ester, and i-Pr2NEt gives 2,5-diaryl-1,5-dienes in high yield. This method avoids the use of stoichiometric metal reductants and is compatible with the presence of halogen, alkyl, electron-donating, and electron-withdrawing substituents on the aromatic ring.

En route to stable all-carbon-substituted silylenes: Synthesis and reactivity of a bis(α-spirocyclopropyl)silylene

The synthesis of a bis(α-spirocyclopropyl)silylene is reported and its reactivity revealed. Liberation of the silylene was accomplished by UV-light-mediated photolysis of a trisilane precursor. Insertion and addition reactions prove the existence and versatility of this new family of bis(α-spirocyclopropyl)-substituted silylenes. Substitution on the flanking cyclopropyls for improved steric shielding of the reactive center remains challenging.

Synthesis of [m.n]cyclophanes: Regiochemistry transfer from vinyl halides to cyclophanes via fischer carbene complexes

The double benzannulation of bis-carbene complexes of chromium with α,ω-diynes generates [m.n]cyclophanes in which all three rings are generated in a single reaction. This triple annulation process is very flexible allowing for the construction of symmetrical [n.n]cyclophanes and unsymmetrical [m.n]cyclophanes as well as isomers in which the two benzene rings are both meta bridged or both para bridged, and isomers that contain both meta and para bridges. The connectivity patterns of the bridges in the cyclophanes can be controlled by regioselectivity transfer from the bis-vinyl carbene complexes in which the substitution pattern of the vinyl groups in the carbene complexes dictate the connectivity pattern in the [m.n]cyclophanes. This synthesis of [n.n]cyclophanes is quite flexible with regard to ring size and can be used with tether lengths ranging from n=2 to n=16 and thus to ring sizes with up to 40 member rings. The only limitation to regioselectivity transfer from the carbene complexes to the [m.n]cyclophanes was found in the synthesis of para,para-cyclophanes with four carbon tethers for which the loss of fidelity occurred with the unexpected formation of meta,para-cyclophanes. Put a ring on it: Regiospecificity is the key in the control of the connectivity patterns in [m.n]cyclophanes. Bis-carbene complexes react with diynes to generate all three rings of [m.n]cyclophanes in a single reaction. The regiochemistry of the vinyl groups in the carbene complexes sets the stage for the nature of the linkages in the cyclophanes. Copyright

An electron-catalyzed cope cyclization. The structure of the 2,5-dicyano-1,5-hexadiene radical anion in the gas phase

The radical anion of 2,5-dicyano-1,5-hexadiene is shown to undergo Cope cyclization in a flowing afterglow-triple quadrupole apparatus. The cyclic structure of the 2,5-dicyano-1,5-hexadiene radical anion was established by using chemical reactivity. The i

PREPARATION AND REACTIONS OF 1,1,4,4-TETRAKIS(TRIMETHYLSILYL)BUTANE-1,4-DIYL DIANION

Reduction of 1,1-bis(trimethylsilyl)ethylene by alkali metal led to the facile dimerization to the 1,1,4,4-tetrakis(trimethylsilyl)butane-1,4-diyl dianion which has been found to be utilized as a reagent for the Peterson reaction.

Photolysis of Reluctant Azoalkanes. Effect of Structure on Photochemical Loss of Nitrogen from 2,3-Diazabicyclooct-2-ene Derivatives

Azoalkanes containing the bicycloskeleton often prove to be remarkable stable toward loss of nitrogen.These derivatives of 2,3-diazabicyclooct-2-ene (DBO) also exhibit fluorescence whose lifetime extends to 600 ns.This paper is an attempt to understand the effect of fused rings and bridgehead substituents on the photochemical and photophysical properties of DBO.The main factor controlling quantum yields of nitrogen is a 6-11 kcal mol-1 activation barrier that differs for the singlet and triplet states and that seems to mimic the barrier to ground-state deazatization.The product distribution for DBO derivatives is rationalized on the basis of interconverting singlet 1,4-biradicaloids.