1,4-Dibromobenzene supplier

Name
1,4-Dibromobenzene
EINECS 203-390-2
CAS No. 106-37-6
Article Data165
CAS DataBase
Density 1.936 g/cm³
Solubility Water Solubility: practically insoluble
Melting Point 86-89 °C
Formula C₆H₄Br₂

Boiling Point 217.9 °C at 760 mmHg

Molecular Weight 235.906

Flash Point 89.3 °C

Transport Information UN 2711

Appearance white or off-white powder

Safety 24/25-36-26

Risk Codes 36/37/38

Molecular Structure

Hazard Symbols Xi

Synonyms Benzene,p-dibromo- (8CI);NSC 33942;p-Bromophenyl bromide;p-Dibromobenzene;p-Phenylene dibromide;para-Dibromobenzene;1,4-Dibromobenzene 99%;

PSA 0.00000

LogP 3.21160

Synthetic route

108-86-1
bromobenzene

106-37-6
1.4-dibromobenzene

Conditions

Conditions Yield

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

374564-35-9
potassium 4-bromophenyltrifluoroborate

106-37-6
1.4-dibromobenzene

Conditions

Conditions Yield

With pyridinium hydrobromide perbromide In tetrahydrofuran; water at 20℃; for 0.333333h; chemoselective reaction; 99%

5467-74-3
4-Bromophenylboronic acid

106-37-6
1.4-dibromobenzene

Conditions

Conditions Yield

With sodium nitrite In acetonitrile at 80℃; for 2h; Sealed tube; 97%

With N-Bromosuccinimide In acetonitrile at 81℃; for 8h; 71%

23268-74-8
(4-bromophenyl)triethylgermane

106-37-6
1.4-dibromobenzene

Conditions

Conditions Yield

With N-Bromosuccinimide In N,N-dimethyl-formamide at 20℃; for 4h; 92%

1,4-benzenebisdiazonium tetrafluoroborate

A

108-86-1
bromobenzene

B

106-37-6
1.4-dibromobenzene

Conditions

Conditions Yield

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

106-37-6
1.4-dibromobenzene

Conditions

Conditions Yield

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%

119945-86-7
(η(5)-C5H5)Fe(CO)2C6H4Fe(CO)2(η(5)-C5H5)

A

dicarbonylcyclopentadienylbromoiron(II)

B

106-37-6
1.4-dibromobenzene

Conditions

Conditions Yield

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

A

14220-21-4
rhenium(I) pentacarbonyl bromide

B

106-37-6
1.4-dibromobenzene

Conditions

Conditions Yield

With bromine In tetrahydrofuran (N2), stirred at room temp. for 30 min; solvent removed, chromy.; A 81%
B 76%

673-40-5
4-bromobenzenediazonium tetrafluoroborate

106-37-6
1.4-dibromobenzene

Conditions

Conditions Yield

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.

106-40-1
4-bromo-aniline

106-37-6
1.4-dibromobenzene

Conditions

Conditions Yield

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%

622-88-8
4-bromophenylhydrazine hydrochloride

106-37-6
1.4-dibromobenzene

Conditions

Conditions Yield

With boron tribromide; dimethyl sulfoxide at 80℃; for 1h; 78%

108-86-1
bromobenzene

A

106-37-6
1.4-dibromobenzene

B

583-53-9
1,2-dibromobenzene

Conditions

Conditions Yield

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;

71-43-2
benzene

A

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

B

106-37-6
1.4-dibromobenzene

C

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

Conditions

Conditions Yield

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

...Expand

1,4-benzenebisdiazonium tetrafluoroborate

79-06-1
2-propenamide

A

106-37-6
1.4-dibromobenzene

B

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

Conditions

Conditions Yield

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

...Expand

93680-30-9
C7H6BrN7

106-37-6
1.4-dibromobenzene

Conditions

Conditions Yield

With tetrabutylammomium bromide; trifluoroacetic acid In acetonitrile at 70 - 80℃; 40%

106-95-6
allyl bromide

106-40-1
4-bromo-aniline

A

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

B

106-37-6
1.4-dibromobenzene

Conditions

Conditions Yield

With tert.-butylnitrite In acetonitrile at 30℃; for 1.33h; A 34%
B n/a

...Expand

925253-14-1
1-{[(4-bromophenyl)dimethylsilyl]methyl}-3-methylimidazolium tetrafluoroborate

106-37-6
1.4-dibromobenzene

Conditions

Conditions Yield

With pyridine; bromine In dichloromethane at 0℃; for 2h; 30%

56-23-5
tetrachloromethane

128-08-5
N-Bromosuccinimide

110-83-8
cyclohexene

94-36-0
dibenzoyl peroxide

A

108-36-1
1,3-dibromobenzene

B

106-37-6
1.4-dibromobenzene

...Expand

74-96-4
ethyl bromide

108-86-1
bromobenzene

A

106-37-6
1.4-dibromobenzene

B

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

Conditions

Conditions Yield

With aluminium trichloride

...Expand

108-86-1
bromobenzene

558-13-4
carbon tetrabromide

106-37-6
1.4-dibromobenzene

Conditions

Conditions Yield

at 150 - 180℃;

at 150 - 180℃;

108-86-1
bromobenzene

563-70-2
bromonitromethane

106-37-6
1.4-dibromobenzene

Conditions

Conditions Yield

With carbon disulfide; aluminium trichloride

108-86-1
bromobenzene

A

106-37-6
1.4-dibromobenzene

B

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

Conditions

Conditions Yield

With bromine Sonnenlicht;

591-50-4
iodobenzene

106-37-6
1.4-dibromobenzene

Conditions

Conditions Yield

With ferric(III) bromide

106-41-2
4-bromo-phenol

106-37-6
1.4-dibromobenzene

Conditions

Conditions Yield

With phosphorus pentabromide durch Destillation;

64-17-5
ethanol

4-bromo-benzenediazonium; tribromoide

106-37-6
1.4-dibromobenzene

3638-73-1
2,5-dibromoaniline

106-37-6
1.4-dibromobenzene

Conditions

Conditions Yield

Diazotization.Behandlung der Diazoniumsalz-Loesung mit H3PO2 bei 5grad;

17333-82-3
4-bromo-benzenediazonium ion

106-37-6
1.4-dibromobenzene

615-42-9
1,2-Diiodobenzene

106-37-6
1.4-dibromobenzene

Conditions

Conditions Yield

With ferric(III) bromide

75-77-4
chloro-trimethyl-silane

106-37-6
1.4-dibromobenzene

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

Conditions

Conditions Yield

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%

76-86-8
Triphenylsilyl chloride

106-37-6
1.4-dibromobenzene

18737-40-1
4-bromophenyltriphenylsilane

Conditions

Conditions Yield

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%

106-37-6
1.4-dibromobenzene

536-74-3
phenylacetylene

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

Conditions

Conditions Yield

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%

106-37-6
1.4-dibromobenzene

24544-04-5
2,6-diisopropylbenzenamine

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

Conditions

Conditions Yield

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;

106-37-6
1.4-dibromobenzene

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

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

Conditions

Conditions Yield

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%

106-37-6
1.4-dibromobenzene

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

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

Conditions

Conditions Yield

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

7751-38-4
Diisopropylsilyl dichloride

106-37-6
1.4-dibromobenzene

1,4-bis(chlorodiisopropylsilyl)benzene

Conditions

Conditions Yield

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%

106-37-6
1.4-dibromobenzene

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

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

Conditions

Conditions Yield

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%

1069137-53-6
N-(4-bromophenyl)-N-o-tolylacetamide

106-37-6
1.4-dibromobenzene

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

Conditions

Conditions Yield

With sodium methylate In methanol; toluene at 100℃; for 3h; Inert atmosphere; 100%

945629-66-3
3-(tert-butyl)-2-hydroxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde

106-37-6
1.4-dibromobenzene

1412912-04-9
C28H30O4

Conditions

Conditions Yield

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;

106-37-6
1.4-dibromobenzene

502-42-1
cycloheptanone

1610027-87-6
C13H17BrO

Conditions

Conditions Yield

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;

106-37-6
1.4-dibromobenzene

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

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

Conditions

Conditions Yield

With n-butyllithium In diethyl ether; hexane room temp., overnight, reflux, 2 h; 99.7%

124-38-9
carbon dioxide

106-37-6
1.4-dibromobenzene

586-76-5
4-Bromobenzoic acid

Conditions

Conditions Yield

With magnesium In tetrahydrofuran at -78℃; for 0.5h; 99%

106-37-6
1.4-dibromobenzene

29949-81-3
tris-para-bromophenylphosphane

Conditions

Conditions Yield

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%

106-37-6
1.4-dibromobenzene

98-80-6
phenylboronic acid

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

Conditions

Conditions Yield

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%

106-37-6
1.4-dibromobenzene

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

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

Conditions

Conditions Yield

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%

141-32-2
acrylic acid n-butyl ester

106-37-6
1.4-dibromobenzene

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

Conditions

Conditions Yield

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;

75-89-8
2,2,2-trifluoroethanol

106-37-6
1.4-dibromobenzene

7789-45-9
copper(II)bromide

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

Conditions

Conditions Yield

With hydrogenchloride In N-methyl-acetamide; (2S)-N-methyl-1-phenylpropan-2-amine hydrate; diethyl ether 99%

...Expand

121-43-7
Trimethyl borate

106-37-6
1.4-dibromobenzene

5467-74-3
4-Bromophenylboronic acid

Conditions

Conditions Yield

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;

106-37-6
1.4-dibromobenzene

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

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

Conditions

Conditions Yield

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

106-37-6
1.4-dibromobenzene

1218780-27-8
potassium N-dodecyl-5-(ethoxycarbonyl)-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

Conditions Yield

With 1-methyl-pyrrolidin-2-one; palladium(II) acetylacetonate; tris-(o-tolyl)phosphine at 95℃; Inert atmosphere; 99%

106-37-6
1.4-dibromobenzene

106-50-3
1,4-phenylenediamine

Conditions

Conditions Yield

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

106-37-6
1.4-dibromobenzene

potassium hexacyanoferrate(II) trihydrate

623-26-7
terephthalonitrile

Conditions

Conditions Yield

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.

106-37-6
1.4-dibromobenzene

potassium 3,3-dimethylbutyltrifluoroborate

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

Conditions

Conditions Yield

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%

106-37-6
1.4-dibromobenzene

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

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

Conditions

Conditions Yield

In methanol at 20℃; for 0.0833333h; Solvent; Inert atmosphere; Schlenk technique; 99%

106-37-6
1.4-dibromobenzene

2294-47-5
1,4-diazidobenzene

Conditions

Conditions Yield

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%

106-37-6
1.4-dibromobenzene

139301-27-2
4-trifluoromethoxyphenylboronic acid

C20H12F6O2

Conditions

Conditions Yield

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

106-37-6
1.4-dibromobenzene

C17H14O3S

C28H20Br2O2S

Conditions

Conditions Yield

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

1,4-Dibromobenzene Chemical Properties

Detail of p-BROMOPHENYL BROMIDE (106-37-6).
Molecular Structure:

Name:1,4-DIBROMOBENZENE
CAS Number:106-37-6
Molecular Formula:C₆H₄Br₂
Molecular Weight:235.92
EINECS:203-390-2
Density:1.841
Melting Point:87 - 89 ^。C
Boiling Point:219 ^。C
Flash Point:91 ^。C
Solubility:Insoluble (< 0.1 g/100ml at 25 ^。C) AUTOIGNITION
Appearance:white to yellow crystalline powder
liansport Information:50kgs
Water Solubility practically insoluble
Merck:14,3019
BRN:1904543
CAS DataBase Reference:106-37-6(CAS DataBase Reference)
NIST Chemistry Reference:106-37-6(NIST)
EPA Substance Registry System:106-37-6(EPA Substance)
Synonyms of p-BROMOPHENYL BROMIDE (106-37-6): 1,4-DIBROMOBENZENE;PARA-DIBROMOBENZENE;P-BENZENE DIBROMIDE;P-DIBROMOBENZENE;1,4-Dibrombenzol;1,4-dibromo-benzen;Benzene, p-dibromo-;Benzene,1,4-dibromo-

1,4-Dibromobenzene Uses

p-BROMOPHENYL BROMIDE (106-37-6) can be used in organic synthesis, dye intermediates.

1,4-Dibromobenzene Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source

mouse LD50 intraperitoneal 1891mg/kg (1891mg/kg) Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 44(12), Pg. 19, 1979.

mouse LD50 oral 3120mg/kg (3120mg/kg) Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 44(12), Pg. 19, 1979.

1,4-Dibromobenzene Consensus Reports
Reported in EPA TSCA Inventory.
1,4-Dibromobenzene Safety Profile

Moderately toxic by ingestion and intraperitoneal routes. When heated to decomposition it emits toxic vapors of Br⁻.
Safety Information of p-BROMOPHENYL BROMIDE (106-37-6).
Hazard Codes:Xi
Risk Statements:36/37/38
Safety Statements:24/25-36-26
RIDADR:UN 2711
RTECS:CZ1791000
HazardClass:9
PackingGroup:III
HS Code:29036990
Hazardous:Substances Data 106-37-6(Hazardous Substances Data)

1,4-Dibromobenzene Specification

Stability and Reactivity of p-BROMOPHENYL BROMIDE (106-37-6).
Chemical Stability: Stable under normal temperatures and pressures.
Conditions to Avoid: Incompatible materials.
Incompatibilities with Other Materials Strong oxidizing agents.
Hazardous Decomposition Products Carbon monoxide, carbon dioxide, hydrogen bromide. Hazardous Polymerization Has not been reported.
First Aid Measures of p-BROMOPHENYL BROMIDE (106-37-6).
Eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid.
Skin: Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes.
Ingestion: Get medical aid. Wash mouth out with water.
Inhalation: Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid.
Notes to Physician: Treat symptomatically and supportively.
Handling and Storage of p-BROMOPHENYL BROMIDE (106-37-6).
Handling: Avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and eyes. Avoid ingestion and inhalation.
Storage: Store in a cool, dry place. Store in a tightly closed container. Store under nitrogen.

Related Products

10,10'-Bis([1,1'-biphenyl]-4-yl)-9,9'-bianthracene

10,10'-Dibromo-9,9'-bianthryl

10,10-Dimethylanthrone

10,10-Oxybisphenoxarsine

10-[1,1'-Biphenyl]-4-yl-2-(1-methylethyl)-9-oxo-9H-thioxanthenium hexafluorophosphate

10,11-Dehydroimipramine

10,11-Dihydro-11-oxodibenzo[b,f][1,4]thiazepine

10,11-Dihydro-2-(4-methyl-1-piperazinyl)-11-(2-athiazolyl)-pyridazino(3,4-b)(1,4)benzoxazepine

10,11-DIHYDRO-2-(4-METHYL-1-PIPERAZINYL)-11-(3,4-XYLYL)PYRIDAZINO(3,4b)(1,4)-BENZOXAZEPINE MALEATE

10,11-Dihydro-5-(3-dimethylamino-2-methylpropyl)-5h-dibenz (b,f)azepine

1063-77-0

106-38-7

106388-34-5

106391-86-0

106391-87-1

106391-88-2

106-39-8

106-40-1

106-41-2

106418-67-1

Hot Products

104987-11-3

141-53-7

8001-54-5

9003-39-8

10161-34-9

402957-28-2

68-19-9

7631-86-9

302-79-4

77-92-9

7758-29-4

9004-65-3

75-05-8

151-21-3

96829-58-2

Conditions	Yield
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

Conditions	Yield
With sodium nitrite In acetonitrile at 80℃; for 2h; Sealed tube;	97%
With N-Bromosuccinimide In acetonitrile at 81℃; for 8h;	71%

Conditions	Yield
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%

Conditions	Yield
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.

Conditions	Yield
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%

Conditions	Yield
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;

Conditions	Yield
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%

Conditions	Yield
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%

Conditions	Yield
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;

Conditions	Yield
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%

Conditions	Yield
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%

Conditions	Yield
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;

Conditions	Yield
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%

Conditions	Yield
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 C37H28N8O2Cl(1-)Pd(2+); potassium carbonate In ethanol at 70℃; for 2h; Suzuki-Miyaura Coupling;	99%

Conditions	Yield
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;

Conditions	Yield
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;

Conditions	Yield
With C24H12Cu2F9N4O7; tetrabutylammomium bromide; ammonia; caesium carbonate In water at 110 - 140℃; for 16h;	99%
With ammonia; C16H16N2O20.8Ni0.2Cu 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

Conditions	Yield
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.

Conditions	Yield
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%

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
mouse	LD50	intraperitoneal	1891mg/kg (1891mg/kg)		Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 44(12), Pg. 19, 1979.
mouse	LD50	oral	3120mg/kg (3120mg/kg)		Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 44(12), Pg. 19, 1979.

Product Name

1,4-Dibromobenzene

Synthetic route

1,4-Dibromobenzene Chemical Properties

1,4-Dibromobenzene Uses

1,4-Dibromobenzene Toxicity Data With Reference

1,4-Dibromobenzene Consensus Reports

1,4-Dibromobenzene Safety Profile

1,4-Dibromobenzene Specification

Related Products

Hot Products