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106-37-6

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106-37-6 Usage

Chemical Properties

Different sources of media describe the Chemical Properties of 106-37-6 differently. You can refer to the following data:
1. 1,4-dibromobenzene is a dibromobenzene. It is a white or off-white powder. freely soluble in hot ethanol, acetone, ether and hot benzene, soluble in ethanol and benzene, insoluble in water. It has a strong smell similar to that of the lighter chlorine analogue. It can be used as a precursor to the dye 6,6-Dibromoindigo.
2. Dibromobenzene is a heavy colorless liquid. Pleasant aromatic odor.

Uses

Different sources of media describe the Uses of 106-37-6 differently. You can refer to the following data:
1. Solvent for oils; ore flotation; motor fuels; organic synthesis.
2. 1,4-Dibromobenzene is used in the synthesis of 2,5-dibromoacetophenone, triarylamines and trans- stilbenes. It is widely used as a heavy liquid solvent as well as a motor oil additive. It finds application as an intermediate in the manufacture of organic chemicals such as dyes, pharmaceuticals and flame retardants for polymeric materials.

Potential Exposure

Dibromobenzene is used as a solvent for oils and in organic synthesis.

Shipping

UN1993 Flammable liquids, n.o.s., Hazard Class: 3; Labels: 3-Flammable liquid, Technical Name Required. UN2514 Bromobenzene, Hazard Class: 3; Labels: 3-Flammable liquid.

Purification Methods

Steam distil the dibromobenzene , then crystallise it from EtOH or MeOH and dry it in the dark under vacuum. Purify it by zone melting. [Beilstein 5 IV 683.]

Incompatibilities

Extremely flammable. May form explosive mixture with air. Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, and epoxides.

Waste Disposal

Use a licensed professional waste disposal service to dispose of this material. All federal, state, and local environmental regulations must be observed. Consult with environmental regulatory agencies for guidance on acceptable disposal practices. Incineration with flue gas scrubbing.

Check Digit Verification of cas no

The CAS Registry Mumber 106-37-6 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,0 and 6 respectively; the second part has 2 digits, 3 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 106-37:
(5*1)+(4*0)+(3*6)+(2*3)+(1*7)=36
36 % 10 = 6
So 106-37-6 is a valid CAS Registry Number.
InChI:InChI:1S/C6H4Br2/c7-5-1-2-6(8)4-3-5/h1-4H

106-37-6 Well-known Company Product Price

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  • TCI America

  • (D0170)  1,4-Dibromobenzene  >99.0%(GC)

  • 106-37-6

  • 25g

  • 98.00CNY

  • Detail
  • TCI America

  • (D0170)  1,4-Dibromobenzene  >99.0%(GC)

  • 106-37-6

  • 100g

  • 270.00CNY

  • Detail
  • TCI America

  • (D0170)  1,4-Dibromobenzene  >99.0%(GC)

  • 106-37-6

  • 500g

  • 650.00CNY

  • Detail
  • Alfa Aesar

  • (A10517)  1,4-Dibromobenzene, 98%   

  • 106-37-6

  • 50g

  • 154.0CNY

  • Detail
  • Alfa Aesar

  • (A10517)  1,4-Dibromobenzene, 98%   

  • 106-37-6

  • 100g

  • 178.0CNY

  • Detail
  • Alfa Aesar

  • (A10517)  1,4-Dibromobenzene, 98%   

  • 106-37-6

  • 250g

  • 378.0CNY

  • Detail
  • Alfa Aesar

  • (A10517)  1,4-Dibromobenzene, 98%   

  • 106-37-6

  • 2500g

  • 2636.0CNY

  • Detail

106-37-6SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name 1,4-dibromobenzene

1.2 Other means of identification

Product number -
Other names Benzene,1,4-dibromo

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:106-37-6 SDS

106-37-6Synthetic route

bromobenzene
108-86-1

bromobenzene

1.4-dibromobenzene
106-37-6

1.4-dibromobenzene

Conditions
ConditionsYield
With bromine fluoride In ethanol; chloroform at -78℃; for 0.5h;100%
With sulfuric acid; bromine; mercury(II) oxide In tetrachloromethane for 2.5h; Heating;76%
With bromine; silver perchlorate; magnesium oxide
potassium 4-bromophenyltrifluoroborate
374564-35-9

potassium 4-bromophenyltrifluoroborate

1.4-dibromobenzene
106-37-6

1.4-dibromobenzene

Conditions
ConditionsYield
With pyridinium hydrobromide perbromide In tetrahydrofuran; water at 20℃; for 0.333333h; chemoselective reaction;99%
4-Bromophenylboronic acid
5467-74-3

4-Bromophenylboronic acid

1.4-dibromobenzene
106-37-6

1.4-dibromobenzene

Conditions
ConditionsYield
With sodium nitrite In acetonitrile at 80℃; for 2h; Sealed tube;97%
With N-Bromosuccinimide In acetonitrile at 81℃; for 8h;71%
(4-bromophenyl)triethylgermane
23268-74-8

(4-bromophenyl)triethylgermane

1.4-dibromobenzene
106-37-6

1.4-dibromobenzene

Conditions
ConditionsYield
With N-Bromosuccinimide In N,N-dimethyl-formamide at 20℃; for 4h;92%
1,4-benzenebisdiazonium tetrafluoroborate

1,4-benzenebisdiazonium tetrafluoroborate

A

bromobenzene
108-86-1

bromobenzene

B

1.4-dibromobenzene
106-37-6

1.4-dibromobenzene

Conditions
ConditionsYield
With dibenzo-18-crown-6; potassium bromide; copper(ll) bromide; 1,10-Phenanthroline; copper(I) bromide In acetonitrile at 20℃; for 0.333333h; Sandmeyer bromination;A 6%
B 91%
4-Bromobenzenediazonium o-benzenedisulfonimide

4-Bromobenzenediazonium o-benzenedisulfonimide

1.4-dibromobenzene
106-37-6

1.4-dibromobenzene

Conditions
ConditionsYield
With tetrabutylammomium bromide; copper In acetonitrile at 20℃; for 0.75h; Substitution;87%
With tetrabutylammomium bromide In acetonitrile at 60℃; for 0.75h; Substitution;83%
(η(5)-C5H5)Fe(CO)2C6H4Fe(CO)2(η(5)-C5H5)
119945-86-7

(η(5)-C5H5)Fe(CO)2C6H4Fe(CO)2(η(5)-C5H5)

A

dicarbonylcyclopentadienylbromoiron(II)

dicarbonylcyclopentadienylbromoiron(II)

B

1.4-dibromobenzene
106-37-6

1.4-dibromobenzene

Conditions
ConditionsYield
With bromine In tetrahydrofuran (N2), stirred for 30 min at room temp.; solvent removed, residue taken up in CH2Cl2, chromy.,;A 82%
B 84%
C6H4{Re(CO)5}2

C6H4{Re(CO)5}2

A

rhenium(I) pentacarbonyl bromide
14220-21-4

rhenium(I) pentacarbonyl bromide

B

1.4-dibromobenzene
106-37-6

1.4-dibromobenzene

Conditions
ConditionsYield
With bromine In tetrahydrofuran (N2), stirred at room temp. for 30 min; solvent removed, chromy.;A 81%
B 76%
4-bromobenzenediazonium tetrafluoroborate
673-40-5

4-bromobenzenediazonium tetrafluoroborate

1.4-dibromobenzene
106-37-6

1.4-dibromobenzene

Conditions
ConditionsYield
With N-Bromosuccinimide; tetrabutylammonium perchlorate In methanol; N,N-dimethyl-formamide at 20℃; for 3h; Sandmeyer Reaction; Electrochemical reaction;81%
With (triphenylphosphine)gold(I) chloride; sodium bromide In acetonitrile at 50℃; for 5h; Sandmeyer Reaction;81 %Spectr.
4-bromo-aniline
106-40-1

4-bromo-aniline

1.4-dibromobenzene
106-37-6

1.4-dibromobenzene

Conditions
ConditionsYield
With p-toluenesulfonyl nitrite; copper(ll) bromide In acetonitrile at 25℃; for 0.0166667h;78%
Stage #1: 4-bromo-aniline With tert.-butylnitrite In dichloromethane; water at 0℃; for 0.166667h;
Stage #2: With carbon tetrabromide; dimethylglyoxal In dichloromethane; water at 15 - 35℃; for 16h;
78%
With N-Bromosuccinimide; sodium nitrite In N,N-dimethyl-formamide at 20℃; for 6h;75%
4-bromophenylhydrazine hydrochloride
622-88-8

4-bromophenylhydrazine hydrochloride

1.4-dibromobenzene
106-37-6

1.4-dibromobenzene

Conditions
ConditionsYield
With boron tribromide; dimethyl sulfoxide at 80℃; for 1h;78%
bromobenzene
108-86-1

bromobenzene

A

1.4-dibromobenzene
106-37-6

1.4-dibromobenzene

B

1,2-dibromobenzene
583-53-9

1,2-dibromobenzene

Conditions
ConditionsYield
With PyHBrCl2; iron(III) chloride In dichloromethane at 20℃; for 2h;A 19%
B 72%
With lead(IV) acetate; trifluoroacetic acid; potassium bromide at 25℃; for 0.5h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
With bromine; ZnBr2 on silica (100 Angstroem) In hexane at 25℃; for 0.116667h; Yields of byproduct given;
benzene
71-43-2

benzene

A

1,2,4,5-tetrabromobenzene
636-28-2

1,2,4,5-tetrabromobenzene

B

1.4-dibromobenzene
106-37-6

1.4-dibromobenzene

C

1,2,4-tribromobenzene
615-54-3

1,2,4-tribromobenzene

Conditions
ConditionsYield
With oxygen; iron; 1,2-dibromomethane at 40℃; for 2h; Overall yield = 520 mg;A 60%
B 11%
C 27%
1,4-benzenebisdiazonium tetrafluoroborate

1,4-benzenebisdiazonium tetrafluoroborate

2-propenamide
79-06-1

2-propenamide

A

1.4-dibromobenzene
106-37-6

1.4-dibromobenzene

B

3,3'-(1,4-phenylene)bis(2-bromopropanamide)

3,3'-(1,4-phenylene)bis(2-bromopropanamide)

Conditions
ConditionsYield
With copper(II) tetrafluroborate hexahydrate; potassium bromide In water; acetone at 0 - 10℃; for 4h;A 32%
B 43%
C7H6BrN7
93680-30-9

C7H6BrN7

1.4-dibromobenzene
106-37-6

1.4-dibromobenzene

Conditions
ConditionsYield
With tetrabutylammomium bromide; trifluoroacetic acid In acetonitrile at 70 - 80℃;40%
allyl bromide
106-95-6

allyl bromide

4-bromo-aniline
106-40-1

4-bromo-aniline

A

1-allyl-4-bromo-benzene
2294-43-1

1-allyl-4-bromo-benzene

B

1.4-dibromobenzene
106-37-6

1.4-dibromobenzene

Conditions
ConditionsYield
With tert.-butylnitrite In acetonitrile at 30℃; for 1.33h;A 34%
B n/a
1-{[(4-bromophenyl)dimethylsilyl]methyl}-3-methylimidazolium tetrafluoroborate
925253-14-1

1-{[(4-bromophenyl)dimethylsilyl]methyl}-3-methylimidazolium tetrafluoroborate

1.4-dibromobenzene
106-37-6

1.4-dibromobenzene

Conditions
ConditionsYield
With pyridine; bromine In dichloromethane at 0℃; for 2h;30%
tetrachloromethane
56-23-5

tetrachloromethane

N-Bromosuccinimide
128-08-5

N-Bromosuccinimide

cyclohexene
110-83-8

cyclohexene

dibenzoyl peroxide
94-36-0

dibenzoyl peroxide

A

1,3-dibromobenzene
108-36-1

1,3-dibromobenzene

B

1.4-dibromobenzene
106-37-6

1.4-dibromobenzene

ethyl bromide
74-96-4

ethyl bromide

bromobenzene
108-86-1

bromobenzene

A

1.4-dibromobenzene
106-37-6

1.4-dibromobenzene

B

1,3,5-triethylbenzene
102-25-0

1,3,5-triethylbenzene

Conditions
ConditionsYield
With aluminium trichloride
bromobenzene
108-86-1

bromobenzene

carbon tetrabromide
558-13-4

carbon tetrabromide

1.4-dibromobenzene
106-37-6

1.4-dibromobenzene

Conditions
ConditionsYield
at 150 - 180℃;
at 150 - 180℃;
bromobenzene
108-86-1

bromobenzene

bromonitromethane
563-70-2

bromonitromethane

1.4-dibromobenzene
106-37-6

1.4-dibromobenzene

Conditions
ConditionsYield
With carbon disulfide; aluminium trichloride
bromobenzene
108-86-1

bromobenzene

A

1.4-dibromobenzene
106-37-6

1.4-dibromobenzene

B

1,1,2,3,4,5,6-heptabromo-cyclohexane
872267-92-0

1,1,2,3,4,5,6-heptabromo-cyclohexane

Conditions
ConditionsYield
With bromine Sonnenlicht;
iodobenzene
591-50-4

iodobenzene

1.4-dibromobenzene
106-37-6

1.4-dibromobenzene

Conditions
ConditionsYield
With ferric(III) bromide
4-bromo-phenol
106-41-2

4-bromo-phenol

1.4-dibromobenzene
106-37-6

1.4-dibromobenzene

Conditions
ConditionsYield
With phosphorus pentabromide durch Destillation;
ethanol
64-17-5

ethanol

4-bromo-benzenediazonium; tribromoide

4-bromo-benzenediazonium; tribromoide

1.4-dibromobenzene
106-37-6

1.4-dibromobenzene

2,5-dibromoaniline
3638-73-1

2,5-dibromoaniline

1.4-dibromobenzene
106-37-6

1.4-dibromobenzene

Conditions
ConditionsYield
Diazotization.Behandlung der Diazoniumsalz-Loesung mit H3PO2 bei 5grad;
4-bromo-benzenediazonium ion
17333-82-3

4-bromo-benzenediazonium ion

1.4-dibromobenzene
106-37-6

1.4-dibromobenzene

1,2-Diiodobenzene
615-42-9

1,2-Diiodobenzene

1.4-dibromobenzene
106-37-6

1.4-dibromobenzene

Conditions
ConditionsYield
With ferric(III) bromide
chloro-trimethyl-silane
75-77-4

chloro-trimethyl-silane

1.4-dibromobenzene
106-37-6

1.4-dibromobenzene

1-bromo-4-(trimethylsilyl)benzene
6999-03-7

1-bromo-4-(trimethylsilyl)benzene

Conditions
ConditionsYield
Stage #1: 1.4-dibromobenzene With n-butyllithium In diethyl ether; hexane at -78℃; for 4h;
Stage #2: chloro-trimethyl-silane In diethyl ether; hexane at -78 - 20℃; for 2.16667h;
100%
Stage #1: 1.4-dibromobenzene With n-butyllithium In diethyl ether; hexane at -78℃; for 0.25h; Inert atmosphere;
Stage #2: chloro-trimethyl-silane In diethyl ether; hexane at 20℃; for 2h; Inert atmosphere;
100%
Stage #1: 1.4-dibromobenzene With n-butyllithium In diethyl ether at -78℃; for 4h; Inert atmosphere; Schlenk technique;
Stage #2: chloro-trimethyl-silane In diethyl ether at -78 - 20℃; Inert atmosphere; Schlenk technique;
100%
Triphenylsilyl chloride
76-86-8

Triphenylsilyl chloride

1.4-dibromobenzene
106-37-6

1.4-dibromobenzene

4-bromophenyltriphenylsilane
18737-40-1

4-bromophenyltriphenylsilane

Conditions
ConditionsYield
Stage #1: 1.4-dibromobenzene With n-butyllithium In diethyl ether; hexane at -78℃;
Stage #2: Triphenylsilyl chloride In diethyl ether; hexane at -78 - 20℃; Further stages.;
100%
Stage #1: 1.4-dibromobenzene With n-butyllithium In diethyl ether at -78℃; for 2.33333h; Inert atmosphere;
Stage #2: Triphenylsilyl chloride In diethyl ether at -78 - 20℃; Inert atmosphere;
87.1%
Stage #1: 1.4-dibromobenzene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Inert atmosphere;
Stage #2: Triphenylsilyl chloride at -78℃; for 2h;
85%
1.4-dibromobenzene
106-37-6

1.4-dibromobenzene

phenylacetylene
536-74-3

phenylacetylene

1,4-bis(2-phenylethynyl)benzene
1849-27-0

1,4-bis(2-phenylethynyl)benzene

Conditions
ConditionsYield
With potassium hydroxide In N,N-dimethyl-formamide at 120℃; for 0.5h; Sonogashira Cross-Coupling;100%
With (1,3-bis(2,6-di-iso-propylphenyl)-4,5-dihydroimidazol-2-ylidene) copper chloride; (1,3-bis(2,6-diisopropylphenyl)-2-imidazolidinylidene)PdCl2(triethylamine); potassium carbonate In dimethyl sulfoxide at 120℃; for 24h; Sonogashira Cross-Coupling;94%
With C28H61ClP2Pd2; diisopropylamine; zinc(II) chloride In tetrahydrofuran at 20℃; for 2h; Inert atmosphere;88%
1.4-dibromobenzene
106-37-6

1.4-dibromobenzene

2,6-diisopropylbenzenamine
24544-04-5

2,6-diisopropylbenzenamine

N,N'-bis(2,6-diisopropylphenyl)-p-phenylenediamine
1068093-94-6

N,N'-bis(2,6-diisopropylphenyl)-p-phenylenediamine

Conditions
ConditionsYield
Stage #1: 1.4-dibromobenzene; 2,6-diisopropylbenzenamine With tri-tert-butyl phosphine; sodium t-butanolate; palladium diacetate In toluene at 110℃; for 14h;
Stage #2: With water; ammonium chloride In toluene Product distribution / selectivity;
100%
Stage #1: 1.4-dibromobenzene; 2,6-diisopropylbenzenamine With tri-tert-butyl phosphine; sodium t-butanolate; dichloro[1,1'-bis(di-t-butylphosphino)ferrocene]palladium(II) In toluene at 110℃; for 14h;
Stage #2: With water; ammonium chloride In toluene Product distribution / selectivity;
1.4-dibromobenzene
106-37-6

1.4-dibromobenzene

tributyl(2,3-dihydrothieno[3,4-b][1,4]dioxin-5-yl)-stannane
175922-79-9

tributyl(2,3-dihydrothieno[3,4-b][1,4]dioxin-5-yl)-stannane

1,4-bis(2-(3,4-ethylenedioxy)thienyl)benzene
168641-43-8

1,4-bis(2-(3,4-ethylenedioxy)thienyl)benzene

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran for 24h; Stille coupling; Inert atmosphere; Reflux;100%
With bis-triphenylphosphine-palladium(II) chloride In N,N-dimethyl-formamide at 80℃; for 2h; Stille coupling; Inert atmosphere;15%
1.4-dibromobenzene
106-37-6

1.4-dibromobenzene

2-(tri-n-butyl)stannyl-5,2'-bithiophene
162717-58-0

2-(tri-n-butyl)stannyl-5,2'-bithiophene

1,4-bis(2,2'-bithiophen-5-yl)benzene

1,4-bis(2,2'-bithiophen-5-yl)benzene

Conditions
ConditionsYield
With bis(tri-t-butylphosphine)palladium(0); cesium fluoride In 1,4-dioxane at 20℃; for 19h; Stille coupling; Inert atmosphere;100%
Diisopropylsilyl dichloride
7751-38-4

Diisopropylsilyl dichloride

1.4-dibromobenzene
106-37-6

1.4-dibromobenzene

1,4-bis(chlorodiisopropylsilyl)benzene

1,4-bis(chlorodiisopropylsilyl)benzene

Conditions
ConditionsYield
Stage #1: 1.4-dibromobenzene With tert.-butyl lithium In tetrahydrofuran; pentane at -78℃; for 1.33333h; Inert atmosphere;
Stage #2: Diisopropylsilyl dichloride In tetrahydrofuran; pentane at -78 - 20℃; for 12h; Inert atmosphere;
100%
1.4-dibromobenzene
106-37-6

1.4-dibromobenzene

4-bromo-N-(4-methoxyphenyl)aniline
13677-42-4

4-bromo-N-(4-methoxyphenyl)aniline

4,4′-dibromo-4′′-methoxytriphenylamine
100308-69-8

4,4′-dibromo-4′′-methoxytriphenylamine

Conditions
ConditionsYield
Stage #1: 1.4-dibromobenzene With 1,1'-bis-(diphenylphosphino)ferrocene; tris-(dibenzylideneacetone)dipalladium(0) In toluene at 20℃; for 0.166667h; Inert atmosphere;
Stage #2: 4-bromo-N-(4-methoxyphenyl)aniline With sodium t-butanolate In toluene at 110℃; for 15h; Hartwig-Buchwald coupling;
100%
Stage #1: 1.4-dibromobenzene With 1,1'-bis-(diphenylphosphino)ferrocene; tris-(dibenzylideneacetone)dipalladium(0) In toluene at 20℃; for 0.166667h; Inert atmosphere;
Stage #2: 4-bromo-N-(4-methoxyphenyl)aniline With sodium t-butanolate In toluene at 110℃; for 15h; Inert atmosphere;
100%
N-(4-bromophenyl)-N-o-tolylacetamide
1069137-53-6

N-(4-bromophenyl)-N-o-tolylacetamide

1.4-dibromobenzene
106-37-6

1.4-dibromobenzene

4-bromo-N-(2-methylphenyl)aniline
1082670-45-8

4-bromo-N-(2-methylphenyl)aniline

Conditions
ConditionsYield
With sodium methylate In methanol; toluene at 100℃; for 3h; Inert atmosphere;100%
3-(tert-butyl)-2-hydroxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde
945629-66-3

3-(tert-butyl)-2-hydroxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde

1.4-dibromobenzene
106-37-6

1.4-dibromobenzene

C28H30O4
1412912-04-9

C28H30O4

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,2-dimethoxyethane; water at 100℃; for 24h; Inert atmosphere;100%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,2-dimethoxyethane; water at 100℃; for 24h; Suzuki-Miyaura Coupling; Inert atmosphere; Schlenk technique;48%
Suzuki Coupling;
1.4-dibromobenzene
106-37-6

1.4-dibromobenzene

cycloheptanone
502-42-1

cycloheptanone

C13H17BrO
1610027-87-6

C13H17BrO

Conditions
ConditionsYield
Stage #1: 1.4-dibromobenzene With n-butyllithium In tetrahydrofuran at -75 - -70℃; Inert atmosphere;
Stage #2: cycloheptanone In tetrahydrofuran at -40℃; Inert atmosphere;
100%
Stage #1: 1.4-dibromobenzene With iodine; magnesium In diethyl ether Grignard Reaction; Reflux;
Stage #2: cycloheptanone In diethyl ether at 20℃; for 2h;
1.4-dibromobenzene
106-37-6

1.4-dibromobenzene

(N,N-dimethyl)-(chloro-phenyl-phosphino)-amine
4073-30-7

(N,N-dimethyl)-(chloro-phenyl-phosphino)-amine

1,4-bis(dimethylaminophenylphosphino)benzene
85573-02-0

1,4-bis(dimethylaminophenylphosphino)benzene

Conditions
ConditionsYield
With n-butyllithium In diethyl ether; hexane room temp., overnight, reflux, 2 h;99.7%
carbon dioxide
124-38-9

carbon dioxide

1.4-dibromobenzene
106-37-6

1.4-dibromobenzene

4-Bromobenzoic acid
586-76-5

4-Bromobenzoic acid

Conditions
ConditionsYield
With magnesium In tetrahydrofuran at -78℃; for 0.5h;99%
1.4-dibromobenzene
106-37-6

1.4-dibromobenzene

tris-para-bromophenylphosphane
29949-81-3

tris-para-bromophenylphosphane

Conditions
ConditionsYield
Stage #1: 1.4-dibromobenzene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h;
Stage #2: With phosphorus trichloride In tetrahydrofuran; hexane at -78 - 20℃; for 2h; Further stages.;
99%
Stage #1: 1.4-dibromobenzene With n-butyllithium In diethyl ether; hexane at 20℃; for 0.0833333h; Substitution;
Stage #2: With phosphorus trichloride In diethyl ether; hexane Addition; Further stages.;
70.8%
Stage #1: 1.4-dibromobenzene With n-butyllithium In tetrahydrofuran at -78℃;
Stage #2: With phosphorus trichloride In tetrahydrofuran at -78 - 20℃;
52%
1.4-dibromobenzene
106-37-6

1.4-dibromobenzene

phenylboronic acid
98-80-6

phenylboronic acid

[1,1';4',1'']terphenyl
92-94-4

[1,1';4',1'']terphenyl

Conditions
ConditionsYield
With trans-chloro(1-naphthyl)bis-(triphenylphosphine)nickel(II); tricyclohexylphosphine tetrafluoroborate; potassium carbonate In water; toluene at 20℃; for 24h; Suzuki-Miyaura cross-coupling reaction; Inert atmosphere;99%
With potassium carbonate In ethanol at 78℃; for 1h; Catalytic behavior; Suzuki-Miyaura Coupling;99%
With C37H28N8O*2Cl(1-)*Pd(2+); potassium carbonate In ethanol at 70℃; for 2h; Suzuki-Miyaura Coupling;99%
1.4-dibromobenzene
106-37-6

1.4-dibromobenzene

2-methyl-but-3-yn-2-ol
115-19-5

2-methyl-but-3-yn-2-ol

1,4-bis(2-hydroxy-2-methyl-4-but-3-ynyl)benzene
2344-53-8

1,4-bis(2-hydroxy-2-methyl-4-but-3-ynyl)benzene

Conditions
ConditionsYield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine for 3h; Inert atmosphere; Reflux;99%
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine for 3h; Sonogashira Cross-Coupling; Inert atmosphere; Reflux;99%
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; diethylamine for 16h; Heating;97%
acrylic acid n-butyl ester
141-32-2

acrylic acid n-butyl ester

1.4-dibromobenzene
106-37-6

1.4-dibromobenzene

1,4-di(2-n-butyloxycarbonyl-trans-vinyl)-benzene

1,4-di(2-n-butyloxycarbonyl-trans-vinyl)-benzene

Conditions
ConditionsYield
With potassium carbonate; bis(dibenzylideneacetone)-palladium(0); 3-(2,6-diisopropylphenyl)-1-(2-diphenylphosphanylbenzyl)-3H-imidazol-1-ium chloride In N,N-dimethyl acetamide at 120℃; for 12h; Heck reaction;99%
With 3-(dimethylamino)propanoic acid hydrochloride; potassium carbonate; palladium diacetate In 1-methyl-pyrrolidin-2-one at 130℃; for 10h; Heck reaction;88%
With palladium diacetate; tri-tert-butyl phosphine; sodium acetate In N,N-dimethyl acetamide at 130℃; for 24h; Heck reaction;75%
With 1,3-bis(5-ferrocenylisoxazoline-3-yl)benzene; tetrabutylammomium bromide; sodium acetate; palladium diacetate In water at 80℃; for 6h; Heck Reaction; diastereoselective reaction;
2,2,2-trifluoroethanol
75-89-8

2,2,2-trifluoroethanol

1.4-dibromobenzene
106-37-6

1.4-dibromobenzene

copper(II)bromide
7789-45-9

copper(II)bromide

1,4-bis(2,2,2-trifluoroethoxy)-benzene
66300-61-6

1,4-bis(2,2,2-trifluoroethoxy)-benzene

Conditions
ConditionsYield
With hydrogenchloride In N-methyl-acetamide; (2S)-N-methyl-1-phenylpropan-2-amine hydrate; diethyl ether99%
Trimethyl borate
121-43-7

Trimethyl borate

1.4-dibromobenzene
106-37-6

1.4-dibromobenzene

4-Bromophenylboronic acid
5467-74-3

4-Bromophenylboronic acid

Conditions
ConditionsYield
Stage #1: 1.4-dibromobenzene With n-butyllithium In tetrahydrofuran; hexane at -30℃; Inert atmosphere; Flow reactor;
Stage #2: Trimethyl borate In tetrahydrofuran; hexane at -30℃; Inert atmosphere; Flow reactor;
99%
Stage #1: 1.4-dibromobenzene With magnesium In tetrahydrofuran at 20℃; for 4h; Inert atmosphere;
Stage #2: Trimethyl borate In tetrahydrofuran at -78 - 20℃; for 19h; Inert atmosphere;
99%
With n-butyllithium In tetrahydrofuran N2; BuLi dropping into org. compd. soln. at -78°C, mixt. keeping 3 h, B-compd. soln. addn. dropwise at -78°C, mixt. allowing to warm to room temp. overnight , stirring 1 h with 10% HCl, extn. (Et2O); org. extracts washing (water), drying, solvent vac. removal;
1.4-dibromobenzene
106-37-6

1.4-dibromobenzene

3-(t-butyl)-4-methoxyphenyl boronic acid
196960-96-0

3-(t-butyl)-4-methoxyphenyl boronic acid

1,4-bis(3-tert-butyl-4-methoxyphenyl)benzene
1202392-74-2

1,4-bis(3-tert-butyl-4-methoxyphenyl)benzene

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); barium hydroxide monohydrate In ISOPROPYLAMIDE; water at 80℃; for 48h; Suzuki-Miyaura double cross-coupling; Inert atmosphere;99%
1.4-dibromobenzene
106-37-6

1.4-dibromobenzene

potassium N-dodecyl-5-(ethoxycarbonyl)-3,4-(propylene-1,3-dioxy)pyrrole-2-carboxylate
1218780-27-8

potassium N-dodecyl-5-(ethoxycarbonyl)-3,4-(propylene-1,3-dioxy)pyrrole-2-carboxylate

diethyl 5,5'-(1,4-phenylene)bis(N-dodecyl-3,4-(propylene-1,3-dioxy)pyrrole-2-carboxylate)
1218780-28-9

diethyl 5,5'-(1,4-phenylene)bis(N-dodecyl-3,4-(propylene-1,3-dioxy)pyrrole-2-carboxylate)

Conditions
ConditionsYield
With 1-methyl-pyrrolidin-2-one; palladium(II) acetylacetonate; tris-(o-tolyl)phosphine at 95℃; Inert atmosphere;99%
1.4-dibromobenzene
106-37-6

1.4-dibromobenzene

1,4-phenylenediamine
106-50-3

1,4-phenylenediamine

Conditions
ConditionsYield
With C24H12Cu2F9N4O7; tetrabutylammomium bromide; ammonia; caesium carbonate In water at 110 - 140℃; for 16h;99%
With ammonia; C16H16N2O2*0.8Ni*0.2Cu at 85℃; under 1500.15 Torr; for 8.5h; Autoclave; Inert atmosphere;92%
Multi-step reaction with 2 steps
1: copper(ll) sulfate pentahydrate; sodium L-ascorbate; potassium carbonate; ammonium hydroxide / dimethyl sulfoxide; glycerol / 8 h / 100 °C
2: copper(ll) sulfate pentahydrate; sodium L-ascorbate; potassium carbonate; ammonium hydroxide / dimethyl sulfoxide; glycerol / 8 h / 100 °C
View Scheme
1.4-dibromobenzene
106-37-6

1.4-dibromobenzene

potassium hexacyanoferrate(II) trihydrate

potassium hexacyanoferrate(II) trihydrate

terephthalonitrile
623-26-7

terephthalonitrile

Conditions
ConditionsYield
With Palladium Nanoparticles with two shape-persistent covalent cages CC1' In N,N-dimethyl-formamide at 140℃; for 15h; Reagent/catalyst; Inert atmosphere;99%
With sodium carbonate In N,N-dimethyl-formamide at 110℃; for 24h; Catalytic behavior; Sealed tube;93 %Chromat.
1.4-dibromobenzene
106-37-6

1.4-dibromobenzene

potassium 3,3-dimethylbutyltrifluoroborate

potassium 3,3-dimethylbutyltrifluoroborate

1,4-bis(3,3-dimethylbutyl)benzene
137039-64-6

1,4-bis(3,3-dimethylbutyl)benzene

Conditions
ConditionsYield
With 2-dicyclohexylphosphino-2′,6′-di-i-propoxy-1,1′-biphenyl; palladium diacetate; caesium carbonate In water; toluene at 115℃; for 16h; Suzuki-Miyaura Coupling; Inert atmosphere;99%
1.4-dibromobenzene
106-37-6

1.4-dibromobenzene

C120H132Ag2Cl8N8O16Rh8(6+)*6CF3O3S(1-)

C120H132Ag2Cl8N8O16Rh8(6+)*6CF3O3S(1-)

C120H132Ag2Cl8N8O16Rh8(6+)*6CF3O3S(1-)*C6H4Br2

C120H132Ag2Cl8N8O16Rh8(6+)*6CF3O3S(1-)*C6H4Br2

Conditions
ConditionsYield
In methanol at 20℃; for 0.0833333h; Solvent; Inert atmosphere; Schlenk technique;99%
1.4-dibromobenzene
106-37-6

1.4-dibromobenzene

1,4-diazidobenzene
2294-47-5

1,4-diazidobenzene

Conditions
ConditionsYield
With sodium azide In ethylene glycol at 100℃; for 3h; Green chemistry;99%
With copper(l) iodide; sodium azide; sodium hydroxide In tetrahydrofuran; water at 95℃; for 4h; Inert atmosphere;60%
1.4-dibromobenzene
106-37-6

1.4-dibromobenzene

4-trifluoromethoxyphenylboronic acid
139301-27-2

4-trifluoromethoxyphenylboronic acid

C20H12F6O2

C20H12F6O2

Conditions
ConditionsYield
With C35H47O3P*C15H16N(1-)*CH3O3S(1-)*Pd(2+); triethylamine In tetrahydrofuran; water at 45℃; for 24h; Suzuki-Miyaura Coupling;99%
1.4-dibromobenzene
106-37-6

1.4-dibromobenzene

C17H14O3S

C17H14O3S

C28H20Br2O2S

C28H20Br2O2S

Conditions
ConditionsYield
Stage #1: 1.4-dibromobenzene With n-butyllithium In tetrahydrofuran at -78℃; for 1h;
Stage #2: C17H14O3S In tetrahydrofuran at 0℃; for 2h;
99%

106-37-6Related news

An STM study of the localized atomic reaction of 1,2- and 1,4-Dibromobenzene (cas 106-37-6) at Si(1 1 1)-7 × 708/20/2019

A comparative study is reported of the thermal reaction of 1,2- and 1,4-dibromobenzene (1,2- and 1,4-diBrPh) on Si(1 1 1)-7 × 7, investigated by STM. Some results are given for the intermediate case of 1,3-diBrPh. The STM images gave evidence of a different pattern of reaction to yield pairs of...detailed

Parent- and daughter-mediated halogenation reactions modeled for 1,2- and 1,4-Dibromobenzene (cas 106-37-6) at Si(1 1 1)-7 × 708/19/2019

We report a first attempt, using AM1, to model the thermal reaction of 1,2- and 1,4-dibromobenzene with a Si(1 1 1)-7 × 7 surface, a reaction recently studied experimentally by scanning tunneling microscopy (STM) [S. Dobrin et al., Surf. Sci. 561 (2004) 11]. As postulated on the basis of the ex...detailed

106-37-6Relevant articles and documents

OXIDATIVE BROMINATION OF AROMATIC COMPOUNDS IN THE KBr-Pb(OAc)4-CF3CO2H SYSTEM

Serguchev, Yu. A.,Davydova, V. G.,Makhon'kov, D. I.,Beletskaya, I. P.

, p. 1550 (1985)

-

Bromination of aromatic compounds using an Fe2O 3/zeolite catalyst

Nishina, Yuta,Takami, Keishi

, p. 2380 - 2383 (2012)

The catalytic bromination of non-activated aromatic compounds has been achieved using an Fe2O3/zeolite catalyst system. FeBr 3 was identified as the catalytic species, formed in situ from HBr and Fe2O3. The catalyst was easy-to-handle and cost effective and could also be recycled. The reaction system was also amenable to the one-pot sequential bromination/C-C bond formation of benzene.

-

Bartsch,Yang

, p. 2503 (1979)

-

A novel synthesis of bromobenzenes using molecular bromine

Oezkan, Hamdi,Disli, Ali,Yildirir, Yilmaz,Tuerker, Lemi

, p. 2478 - 2483 (2007)

Certain substituted bromobenzenes have been synthesized in acceptable yields using a novel Sandmeyer type reaction. The reactions are relatively quick and possibly proceed via a radical mechanism.

Wibaut et al.

, p. 1031,1039 (1950)

-

Billman,Dougherty

, p. 387 (1939)

-

Oxidative bromination of non-activated aromatic compounds with AlBr3/KNO3 mixture

Rahu, Ida,J?rv, Jaak

, p. 1219 - 1227 (2020)

Bromination of non-activated aromatic compounds with reaction mixture containing KNO3 and AlBr3 was studied in liquid substrates and in solvent. Aluminium bromide has three different roles in this reaction mixture. First, it is a source of bromide ions, which are essential in oxidative bromination application. Second, it acts as a catalyst, and lastly, it forms acidic environment via its hydrolysis, which is necessary for enhancement of the oxidising properties of nitrate ions. It was shown that when changing the reaction conditions, different side reactions (like nitration or Friedel–Crafts type arylation) can occur. However, it is possible to guide the reaction path and receive the desired outcome by choosing the suitable reaction conditions. In addition, it was shown that there has to be water content in this reaction mixture as the bromine formation rate depends on it, while there exists an optimal volume of water, where bromine formation is the fastest.

Highly efficient and selective electrophilic and free radical catalytic bromination reactions of simple aromatic compounds in the presence of reusable zeolites

Smith, Keith,El-Hiti, Gamal A.,Hammond, Mark E.W.,Bahzad, Dawoud,Li, Zhaoqiang,Siquet, Christophe

, p. 2745 - 2752 (2000)

Reactions of mono-substituted aromatics of moderate activity with bromine in the presence of stoichiometric amounts of zeolite NaY proceed in high yield and with high selectivity to the corresponding para-bromo products. The zeolites can easily be regenerated by heating and reused. Similar para-selectivity can be achieved in the case of toluene by use of tert-butyl hypobromite as reagent, zeolite HX as catalyst, and a solvent comprising a mixture of tetrachloromethane and diethyl ether. Radical bromination of ethyl 4-methylbenzoate using bromine in the presence of light is catalysed by various zeolites and affords a high yield of ethyl 4-(bromomethyl)benzoate but with no great improvement in selectivity for monobromination.

O'Kelly

, p. 2783 (1934)

Poly-N-bromosulfonamide-melamine as a novel brominating reagent for regioselective ipso-bromination of arylboronic acids

Alavinia, Sedigheh,Ghorbani-Vaghei, Ramin

, p. 1269 - 1276 (2021/08/27)

A practical synthetic method for the synthesis of aryl bromide was developed through regioselective bromination of boronic acid in the presence of poly-N-bromosulfonamide-melamine (PBBSM). In this regard, a novel heterogeneous support, cross-linked poly sulfonamide-melamine, has been successfully synthesized to stabilize bromine with high surface functional group density (6.6?mmol Br+/g). The prepared reagent is a novel brominating reagent that combines the effective functions of N-bromosulfonamide, N-bromosulfonamide-melamine, and melamine groups. The structure of PBBSM was characterized using XRD, FT–IR, 1H NMR, TGA, FE-SEM, EDX, and TGA analysis. Graphic abstract: [Figure not available: see fulltext.]

Photoinduced Acetylation of Anilines under Aqueous and Catalyst-Free Conditions

Yang, Yu-Ming,Yan, Wei,Hu, Han-Wei,Luo, Yimin,Tang, Zhen-Yu,Luo, Zhuangzhu

, p. 12344 - 12353 (2021/09/02)

A green and efficient visible-light induced functionalization of anilines under mild conditions has been reported. Utilizing nontoxic, cost-effective, and water-soluble diacetyl as photosensitizer and acetylating reagent, and water as the solvent, a variety of anilines were converted into the corresponding aryl ketones, iodides, and bromides. With advantages of environmentally friendly conditions, simple operation, broad substrate scope, and functional group tolerance, this reaction represents a valuable method in organic synthesis.

Orthogonal Stability and Reactivity of Aryl Germanes Enables Rapid and Selective (Multi)Halogenations

Deckers, Kristina,Fricke, Christoph,Schoenebeck, Franziska

supporting information, p. 18717 - 18722 (2020/08/25)

While halogenation is of key importance in synthesis and radioimaging, the currently available repertoire is largely designed to introduce a single halogen per molecule. This report makes the selective introduction of several different halogens accessible. Showcased here is the privileged stability of nontoxic aryl germanes under harsh fluorination conditions (that allow selective fluorination in their presence), while displaying superior reactivity and functional-group tolerance in electrophilic iodinations and brominations, outcompeting silanes or boronic esters under rapid and additive-free conditions. Mechanistic experiments and computational studies suggest a concerted electrophilic aromatic substitution as the underlying mechanism.

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