10364-04-2

Basic information

• Product Name: 1,4-Dibromobicyclo[2.2.2]octane
• Synonyms: 1,4-Dibromobicyclo[2.2.2]octane
• CAS NO: 10364-04-2
• Molecular Formula: C₈H₁₂Br₂
• Molecular Weight: 267.9889
• Mol File: 10364-04-2.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 247.9°Cat760mmHg
• Flash Point: 113.8°C
• Appearance: /
• Density: 1.898g/cm³
• Vapor Pressure: 0.0395mmHg at 25°C
• Refractive Index: 1.631
• CAS DataBase Reference: 1,4-Dibromobicyclo[2.2.2]octane(CAS DataBase Reference)
• NIST Chemistry Reference: 1,4-Dibromobicyclo[2.2.2]octane(10364-04-2)
• EPA Substance Registry System: 1,4-Dibromobicyclo[2.2.2]octane(10364-04-2)

Safety Data

• Hazardous Substances Data: 10364-04-2(Hazardous Substances Data)

Usage

General Description

1,4-Dibromobicyclo[2.2.2]octane is a chemical compound that consists of a bicyclic structure with two bromine atoms attached to the first and fourth carbon atoms. It is a colorless liquid at room temperature with a molecular formula of C8H12Br2. This chemical is used in organic synthesis as a building block for the preparation of various organic compounds, including pharmaceuticals and agrochemicals. It is also used as a reagent in chemical reactions due to its unique structural and chemical properties. In addition, it is important to handle this chemical with caution as it is considered harmful if ingested or inhaled and can cause skin and eye irritation upon contact.

InChI:InChI=1/C8H12Br2/c9-7-1-2-8(10,5-3-7)6-4-7/h1-6H2

Synthetic route

1,4-diiodobicyclo<2.2.2>octane (10364-05-3) → bicyclo[2.2.2]octane-1,4-dibromide (10364-04-2)

Conditions	Yield
With bromine In dichloromethane for 1.25h; Ambient temperature;	96%

1,4-dihydroxybicyclo[2.2.2]nonane (1194-44-1) → bicyclo[2.2.2]octane-1,4-dibromide (10364-04-2)

Conditions	Yield
With PPA; phosphorus tribromide at 130℃; for 0.75h;	66%

4-acetoxybicyclo<2.2.2>octan-1-ol (54774-94-6) → bicyclo[2.2.2]octane-1,4-dibromide (10364-04-2)

Conditions	Yield
With PPA; phosphorus tribromide at 130℃; for 0.75h;	66%

1,4-Diacetoxybicyclo<2.2.2>octane (10364-35-9) → bicyclo[2.2.2]octane-1,4-dibromide (10364-04-2)

Conditions	Yield
With PPA; phosphorus tribromide at 130℃; for 0.75h;	66%
With phosphoric acid; potassium bromide at 100℃; for 4h;

1,4-bicyclo[2.2.2]octanedicarboxylic acid (711-02-4) → bicyclo[2.2.2]octane-1,4-dibromide (10364-04-2)

Conditions	Yield
With bromine; ethylene dibromide; mercury(II) oxide
(i) HgO, MgSO4, BrCH2CH2Br, (ii) Br2; Multistep reaction;
With bromine; magnesium sulfate; mercury(II) oxide In ethylene dibromide at 75℃; for 14h; Inert atmosphere;

1-bromo-4-hydroxybicyclo<2.2.2>octane (72948-88-0) → 1,4-Dichloro-bicyclo<2.2.2>octane (1123-39-3) + bicyclo[2.2.2]octane-1,4-dibromide (10364-04-2) + 1-bromo-4-chlorobicyclo<2.2.2>octane (78016-69-0)

Conditions	Yield
With phosphoric acid; sodium chloride at 120 - 130℃; for 1h; Title compound not separated from byproducts;	A 12.5 % Chromat. B 7.5 % Chromat. C 80 % Chromat.

Bicyclo<2.2.2.>octan-1,4-dicarbonsauere-ethylester (1659-75-2) → bicyclo[2.2.2]octane-1,4-dibromide (10364-04-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: KOH / ethanol 2: Br2, HgO, BrCH2CH2Br View Scheme

o-xylene (95-47-6) + bicyclo[2.2.2]octane-1,4-dibromide (10364-04-2) → 1,4-bis(3,4-dimethylphenyl)bicyclo[2.2.2]octane

Conditions	Yield
With aluminum (III) chloride at 55℃; for 6h; Inert atmosphere;	70%

bicyclo[2.2.2]octane-1,4-dibromide (10364-04-2) → bicyclo[2,2,2]octane (280-33-1)

Conditions	Yield
With potassium hydroxide; hydrogen; nickel In ethanol	50.5%

bicyclo[2.2.2]octane-1,4-dibromide (10364-04-2) + benzene (71-43-2) → 1,4-Diphenyl-bicyclo<2.2.2>octane (23062-63-7)

Conditions	Yield
With aluminum (III) chloride at 0 - 40℃; Inert atmosphere;	38%

bicyclo[2.2.2]octane-1,4-dibromide (10364-04-2) → 1,4-dihydroxybicyclo[2.2.2]nonane (1194-44-1)

Conditions	Yield
With iron; copper(II) oxide at 215℃;

bicyclo[2.2.2]octane-1,4-dibromide (10364-04-2) → 1,4-Dichloro-bicyclo<2.2.2>octane (1123-39-3)

Conditions	Yield
(i) (electrolysis), Br, DMF, (ii) Cl2; Multistep reaction;

bicyclo[2.2.2]octane-1,4-dibromide (10364-04-2) → 1,4-diiodobicyclo<2.2.2>octane (10364-05-3)

Conditions	Yield
With bromine; aluminium; methyl iodide

bicyclo[2.2.2]octane-1,4-dibromide (10364-04-2) → 1,4-Dichloro-1,4-bis-chloromethyl-cyclohexane

Conditions	Yield
(i) (electrolysis), Br, DMF, (ii) Cl2; Multistep reaction;

bicyclo[2.2.2]octane-1,4-dibromide (10364-04-2) → 1,4-Bicyclo<2,2,2>oktylen-di-p-aethoxybenzoat (28099-20-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: CuO, Fe / 215 °C 2: Py View Scheme

bicyclo[2.2.2]octane-1,4-dibromide (10364-04-2) → 1,4-Bicyclo<2,2,2>oktylen-di-4-methoxybicyclo<2,2,2>oktan-1-carboxylat (28099-26-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: CuO, Fe / 215 °C 2: Py / benzene View Scheme

bicyclo[2.2.2]octane-1,4-dibromide (10364-04-2) → 1,4-Bicyclo<2,2,2>oktylen-di-p-propoxybenzoat (28099-21-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: CuO, Fe / 215 °C 2: Py View Scheme

bicyclo[2.2.2]octane-1,4-dibromide (10364-04-2) → 1,4-Bicyclo<2,2,2>oktylen-di-p-butoxybenzoat (28099-22-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: CuO, Fe / 215 °C 2: Py View Scheme

bicyclo[2.2.2]octane-1,4-dibromide (10364-04-2) → 1,4-Bicyclo<2,2,2>oktylen-di-p-hexoxybenzoat (24707-07-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: CuO, Fe / 215 °C 2: Py View Scheme

bicyclo[2.2.2]octane-1,4-dibromide (10364-04-2) → 1,4-Bicyclo<2,2,2>oktylen-di-p-heptoxybenzoat (28099-24-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: CuO, Fe / 215 °C 2: Py View Scheme

bicyclo[2.2.2]octane-1,4-dibromide (10364-04-2) → 1,4-Bicyclo<2,2,2>oktylen-di-p-oktoxy-benzoat (24707-08-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: CuO, Fe / 215 °C 2: Py View Scheme

Upstream product

• 711-02-4 1,4-bicyclo[2.2.2]octanedicarboxylic acid 
• 1194-44-1 1,4-dihydroxybicyclo[2.2.2]octane 
• 72948-88-0 1-bromo-4-hydroxybicyclo<2.2.2>octane 
• 711-02-4 bicyclo<2.2.2>octane-1,4-dicarboxylic acid 
• 1659-75-2 Bicyclo<2.2.2.>octan-1,4-dicarbonsauere-ethylester 
• 10364-35-9 1,4-Diacetoxybicyclo<2.2.2>octane 
• 54774-94-6 4-acetoxybicyclo<2.2.2>octan-1-ol 
• 10364-05-3 1,4-diiodobicyclo<2.2.2>octane 

Downstream Products

• 280-33-1 bicyclo[2,2,2]octane 
• 23062-63-7 1,4-Diphenyl-bicyclo<2.2.2>octane 
• 24707-08-2 1,4-Bicyclo<2,2,2>oktylen-di-p-oktoxy-benzoat 
• 28099-24-3 1,4-Bicyclo<2,2,2>oktylen-di-p-heptoxybenzoat 
• 24707-07-1 1,4-Bicyclo<2,2,2>oktylen-di-p-hexoxybenzoat 
• 28099-22-1 1,4-Bicyclo<2,2,2>oktylen-di-p-butoxybenzoat 
• 28099-21-0 1,4-Bicyclo<2,2,2>oktylen-di-p-propoxybenzoat 
• 28099-20-9 1,4-Bicyclo<2,2,2>oktylen-di-p-aethoxybenzoat 
• 10364-05-3 1,4-diiodobicyclo<2.2.2>octane 
• 1123-39-3 1,4-Dichloro-bicyclo<2.2.2>octane 
• 1194-44-1 1,4-dihydroxybicyclo[2.2.2]octane 

Relevant articles and documents

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Tuning Singlet Fission in π-Bridge-π Chromophores

We have designed a series of pentacene dimers separated by homoconjugated or nonconjugated bridges that exhibit fast and efficient intramolecular singlet exciton fission (iSF). These materials are distinctive among reported iSF compounds because they exist in the unexplored regime of close spatial proximity but weak electronic coupling between the singlet exciton and triplet pair states. Using transient absorption spectroscopy to investigate photophysics in these molecules, we find that homoconjugated dimers display desirable excited-state dynamics, with significantly reduced recombination rates as compared to conjugated dimers with similar singlet fission rates. In addition, unlike conjugated dimers, the time constants for singlet fission are relatively insensitive to the interplanar angle between chromophores, since rotation about σ bonds negligibly affects the orbital overlap within the π-bonding network. In the nonconjugated dimer, where the iSF occurs with a time constant >10 ns, comparable to the fluorescence lifetime, we used electron spin resonance spectroscopy to unequivocally establish the formation of triplet-triplet multiexcitons and uncoupled triplet excitons through singlet fission. Together, these studies enable us to articulate the role of the conjugation motif in iSF.

SYNTHESIS OF BICYCLO[2.2.2]OCTANE DERIVATIVES

Provided is a process for the preparation of certain 1,4-bicyclo[2.2.2]octane derivatives. The new synthetic procedure involves treating 1,4-dimethylene cyclohexane with an oxidizing agent in the presence of a transition metal catalyst to afford an oxo-substituted bicyclo[2.2.2]octane species. This intermediate structure can then be further derivatized. The processes of this disclosure thus affords a novel and simplified means for the commercial production of a wide variety of bicyclo[2.2.2]octane derivatives.

SYNTHESIS OF BRIDGEHEAD CHLORO-, BROMO- AND IODOBICYCLOOCTANES

The paper describes transformations of hydroxy-, acetoxy- or methoxy-bridgehead bicyclooctanes into bridgehead chloro, bromo or iodo derivatives by action of inorganic halides in the medium of orthophosphoric or polyphosphoric acids.