15481-39-7

Basic information

• Product Name: BROMINE-1,4-DIOXANE COMPLEX
• Synonyms: BROMINE-1,4-DIOXANE COMPLEX, 0.25M SOLUTION IN 1,4-DIOXANE;Bromine-1,4-dioxane complex0.25M solution in 1,4-dioxaneAcroSeal§3;Bromine-1,4-dioxane complex,95%;Bromine-1,4-dioxane complex, 0.25M solution in 1,4-dioxane, AcroSeal;Bromine-1,4-Dioxane;1,4-DIOXANE-BROMINE COMPLEX;1 4-DIETHYLENE DIOXIDE DIBROMIDE;BROMINE-1,4-DIOXANE COMPLEX
• CAS NO: 15481-39-7
• Molecular Formula: Br₂*C₄H₈O₂
• Molecular Weight: 247.91
• Product Categories: Dioxanes;Dioxanes & Dioxolanes
• Mol File: 15481-39-7.mol
• Article Data: 6

Chemical Properties

• Melting Point: 66 °C
• Boiling Point: 95 °C
• Flash Point: 12.2°C
• Appearance: Clear red/Liquid
• Density: g/cm³
• Vapor Pressure: 38.2mmHg at 25°C
• Storage Temp.: Freezer
• Solubility: soluble in Methanol
• CAS DataBase Reference: BROMINE-1,4-DIOXANE COMPLEX(CAS DataBase Reference)
• NIST Chemistry Reference: BROMINE-1,4-DIOXANE COMPLEX(15481-39-7)
• EPA Substance Registry System: BROMINE-1,4-DIOXANE COMPLEX(15481-39-7)

Safety Data

• RIDADR: 1325
• HazardClass: 4.1
• PackingGroup: III
• Hazardous Substances Data: 15481-39-7(Hazardous Substances Data)

Usage

Description

BROMINE-1,4-DIOXANE COMPLEX, also known as Dioxane Bromonium Bromide, is a clear red solution with unique chemical properties. It is a complex compound that plays a significant role in various chemical reactions and applications across different industries.

Uses

Used in Pharmaceutical Industry:
BROMINE-1,4-DIOXANE COMPLEX is used as a synthetic agent for the production of 2-hydroxy glycals, which are essential intermediates in the synthesis of various pharmaceutical compounds. These glycals have potential applications in the development of new drugs and therapies.
Used in Agricultural Industry:
BROMINE-1,4-DIOXANE COMPLEX is used as a precursor in the preparation of phytoalexins, which are natural antimicrobial and antioxidant compounds produced by plants in response to pathogen attacks. These phytoalexins help protect plants from diseases and enhance their overall health, contributing to increased crop yields and improved food security.

InChI:InChI=1/C4H8O2.Br2/c1-2-6-4-3-5-1;1-2/h1-4H2;

Synthetic route

1,4-dioxane (123-91-1) + bromine (7726-95-6) → dioxane dibromide (15481-39-7)

Conditions	Yield
at 20℃; for 2h; Cooling with ice;	65%

1,4-dioxane (123-91-1) → dioxane dibromide (15481-39-7)

Conditions	Yield
With bromine at 0 - 23℃; for 3h;	57%
With bromine
With bromine	10 g

oxirane (75-21-8) → dioxane dibromide (15481-39-7)

Conditions	Yield
With bromine im geschlossenen Gefaess;

dioxane dibromide (15481-39-7) + 2,4-diethoxy-3-methylphenol (162976-09-2) → 6-bromo-2,4-diethoxy-3-methylphenol (1061630-50-9)

Conditions	Yield
With potassium carbonate In dichloromethane at -78 - 20℃; for 0.916667h;	88%

dioxane dibromide (15481-39-7) + 7-cinnamyloxy-4-methylcoumarin → 3-bromo-7-(2,3-dibromo-3-phenylpropoxy)-4-methylcoumarin (1374992-44-5)

Conditions	Yield
at 0 - 20℃; for 4h; Neat (no solvent); regioselective reaction;	86%

4-methyl-7-methoxy-2H-1-benzopyran-2-one (2555-28-4) + dioxane dibromide (15481-39-7) → 3-bromo-7-methoxy-4-methylcoumarin (75908-67-7)

Conditions	Yield
at 0 - 20℃; for 2h; Neat (no solvent); regioselective reaction;	85%

7-hydroxy-4-methyl-chromen-2-one (90-33-5, 79566-13-5) + dioxane dibromide (15481-39-7) → 3-bromo-7-hydroxy-4-methyl-chromen-2-one (55977-10-1)

Conditions	Yield
at 0 - 20℃; for 3h; Neat (no solvent); regioselective reaction;	84%

4-methyl-2H-chromen-2-one (607-71-6) + dioxane dibromide (15481-39-7) → 3-bromo-4-hydroxycoumarin (50361-81-4)

Conditions	Yield
at 0 - 20℃; for 2h; Neat (no solvent); regioselective reaction;	83%

7-allyloxycoumarin (31005-03-5) + dioxane dibromide (15481-39-7) → 7-(2,3-dibromopropoxy)coumarin

Conditions	Yield
at 0 - 20℃; for 0.5h; Neat (no solvent); regioselective reaction;	83%

bis[4,6-di-tert-butyl-N-(2,6-diisopropylphenyl)-o-amidophenolato]tin(IV) tetrahydrofuratate (922509-12-4) + dioxane dibromide (15481-39-7) → dibromobis(4,6-di-tert-butyl-N-(2,6-diisopropylphenyl)-o-iminobenzosemiquinonato)tin(IV)

Conditions	Yield
In acetonitrile exclusion of air and moisture; soln. of Br2*diox (1 mmol) in MeCN added dropwise to soln. of Sn complex (1 mmol) in MeCN; soln. concd., stored at -12°C for 12 h, crystals isolated; elem. anal.;	82.3%

[(η5-methylcyclopentadienyl)4Fe4(μ4-η2:η2:η1:η1-HCCH)2] + dioxane dibromide (15481-39-7) → [(η5-C5H4Me)4Fe4(HCCH)2](Br3)2

Conditions	Yield
In dichloromethane (N2); using Schlenk techniques; addn. of excess of Br2*C4H8O2 to soln. of (η5-C5H4Me)4Fe4(HCCH)2 in CH2Cl2 at room temp. under constant stirring; pptn., filtration, washing with CH2Cl2, extn. with MeCN; removal of solvent, elem. anal.;	79%

7-hydroxy-2H-chromen-2-one (93-35-6) + dioxane dibromide (15481-39-7) → 3-bromo-7-hydroxy-2H-1-benzopyran-2-one (146900-52-9)

Conditions	Yield
at 0 - 20℃; for 2h; Neat (no solvent); regioselective reaction;	79%

7-methoxycoumarin (531-59-9) + dioxane dibromide (15481-39-7) → 3-bromo-7-methoxy-2H-chromen-2-one (72167-80-7)

Conditions	Yield
at 0 - 20℃; for 3h; Neat (no solvent); regioselective reaction;	79%

7-amino-4-methylcoumarin (103264-02-4) + dioxane dibromide (15481-39-7) → 6-amino-5,7-dibromo-4-methylcoumarin (1374992-46-7)

Conditions	Yield
at 0 - 20℃; for 2h; Neat (no solvent); regioselective reaction;	77%

coumarin (91-64-5) + dioxane dibromide (15481-39-7) → (3R*,4R*)-3,4-dibromo-3,4-dihydrocoumarin

Conditions	Yield
at 0 - 20℃; for 0.5h; Neat (no solvent); regioselective reaction;	76%

dioxane dibromide (15481-39-7) + 7-propargyloxy-4-methyl-2H-chromen-2-one (67268-43-3) → 3-bromo-7-(2,3-dibromoallyloxy)-4-methylcoumarin (1374992-45-6)

Conditions	Yield
at 0 - 20℃; for 2h; Neat (no solvent); regioselective reaction;	73%

7-hydroxy-2H-chromen-2-one (93-35-6) + dioxane dibromide (15481-39-7) → 3,8-dibromo-7-hydroxycoumarin (1374992-42-3)

Conditions	Yield
at 0 - 20℃; for 4h; Neat (no solvent); regioselective reaction;	72%

(3,6-di-tert-butylcatecholato)dichlorotin(IV) ditetrahydrofuranate (873853-16-8) + dioxane dibromide (15481-39-7) → (3,6-di-tert-butyl-o-benzosemiquinonato)dichlorobromotin(IV) tetrahydrofuranate

Conditions	Yield
In acetonitrile a soln. of Br compd. added dropwise to a soln. of Sn compd.; concd., stored at -12°C overnight; elem. anal., TGA;	72%

(3,6-di-tert-butylcatecholato)dichlorotin(IV) ditetrahydrofuranate (1357090-57-3) + dioxane dibromide (15481-39-7) → (3,6-di-tert-butyl-o-benzosemiquinonato)tribromotin(IV) tetrahydrofuranate

Conditions	Yield
In acetonitrile a soln. of Br compd. added dropwise to a soln. of Sn compd.; concd., stored at -12°C overnight; elem. anal., TGA;	71%

Cp2Nb(SiHMe2)2H (252027-47-7) + dioxane dibromide (15481-39-7) → [NbH(C5H5)2(SiBr(CH3)2)2] (252027-52-4) + NbH(C5H5)2(Si(CH3)2(2)H)(Si(CH3)2Br)

Conditions	Yield
In diethyl ether under Ar; to Nb complex was added a soln. of Br2*O2C4H8 (1 equiv.) in ether, the mixt. was stirred overnight at 25°C; the mixt. was filtered, the volatiles were removed; Nb(C5H5)2H(Si(CH3)2((2)H)(Si(CH3)2Br) was observed only by NMR;	A 70% B n/a

6-aminocoumarin (14415-44-2) + dioxane dibromide (15481-39-7) → 5,7-dibromo-6-aminocoumarin (866475-81-2)

Conditions	Yield
at 0 - 20℃; for 1h; Neat (no solvent); regioselective reaction;	70%

3-Trimethylsilylinden (18053-75-3) + dioxane dibromide (15481-39-7) → 1-bromoindene (61083-09-8)

Conditions	Yield
In tetrahydrofuran at -78℃;	66%

6-aminocoumarin (14415-44-2) + dioxane dibromide (15481-39-7) → 6-amino-5-bromo-2H-chromen-2-one

Conditions	Yield
at 0 - 20℃; for 1h; Neat (no solvent); regioselective reaction;	62%

7-allyloxy-4-methyl-2H-chromen-2-one (3993-57-5) + dioxane dibromide (15481-39-7) → 3-bromo-7-(2,3-dibromopropoxy)-4-methylcoumarin (1374992-43-4)

Conditions	Yield
at 0 - 20℃; for 4h; Neat (no solvent); regiospecific reaction;	56%

Cp2Nb(SiHMe2)2H (252027-47-7) + dioxane dibromide (15481-39-7) → Cp2Nb(SiHMe2)H(SiBrMe2) (717827-34-4)

Conditions	Yield
anaerobic and anhydrous conditions; 0.5 equiv. of Br2*dioxane;	44%

1-phenyl-2,8,9-trioxa-5-aza-1-silabicyclo{3.3.3}undecane (2097-19-0) + dioxane dibromide (15481-39-7) → 1-bromosilatrane (33446-82-1) + 1-[2-(2-bromoethoxy)ethoxy]silatrane

Conditions	Yield
In dichloromethane at 20℃; Substitution;	A 39% B 11.7%

dioxane dibromide (15481-39-7) + 1-vinylsilatrane (2097-18-9) → 1-bromosilatrane (33446-82-1) + 1-[2-(2-bromoethoxy)ethoxy]silatrane

Conditions	Yield
In dichloromethane at 20℃; Substitution;	A 16.4% B 14.6%

Upstream product

• 123-91-1 1,4-dioxane 
• 7726-95-6 bromine 
• 75-21-8 oxirane 

Downstream Products

• 146900-52-9 3-bromo-7-hydroxy-2H-1-benzopyran-2-one 
• 72167-80-7 3-bromo-7-methoxy-2H-chromen-2-one 
• 55977-10-1 3-bromo-7-hydroxy-4-methyl-chromen-2-one 
• 1374992-44-5 3-bromo-7-(2,3-dibromo-3-phenylpropoxy)-4-methylcoumarin 
• 1061630-50-9 6-bromo-2,4-diethoxy-3-methylphenol 
• 61083-09-8 1-bromoindene 
• 106-41-2 4-bromo-phenol 
• 2648-71-7 3-bromo-3-methyl-2-butanone 
• 19967-55-6 1-bromo-3-methyl-2-butanone 
• 106-93-4 ethylene dibromide 
• 123-91-1 1,4-dioxane 

Relevant articles and documents

A convenient and efficient method for the synthesis of 2-hydroxy glycals

A convenient and efficient method for preparing 2-hydroxy glycals was developed from thioglycosides by using 1,4-dioxane-bromine complex/DMAP as an efficient promoter with good yield (61-85%). In this synthetic method, a wide range of sugar thioglycosides could be used as substrates.

Dioxane dibromide mediated bromination of substituted coumarins under solvent-free conditions

An efficient solvent-free protocol for regioselective bromination of substituted coumarins has been developed by using dioxane dibromide as the solid brominating agent. The efficacy of the solvent-free protocol has been established. The effects of the electronic nature and location of the substituents on the outcome of the reaction have been rationalized with a proposed mechanism.

PROCESS FOR THE PREPARATION OF OPTICALLY ACTIVE 2-AMINO-1-PHENYLETHANOLS

Optically active 2-amino-l-phenylethanols of formula (I) or its mirror image, wherein R1 is C1-6 alkyl or aryl-substituted C1-6 alkyl and R2 through R6 are independently hydrogen, hydroxy or C1-6 alkoxy, or salts thereof are prepared by asymmetric hydrogenation of the corresponding 2-aminoaceto-phenones in the presence of a rhodium complex catalyst comprising a chiral diphosphine ligand, wherein each phosphorus atom is part of a heterocyclic ring system which contains at least one chiral carbon atom directly bound to the phosphorus atom.