Product Name

  • Name

    5-Bromo-m-xylene

  • EINECS 629-686-5
  • CAS No. 556-96-7
  • Article Data30
  • CAS DataBase
  • Density 1.339 g/cm3
  • Solubility
  • Melting Point -20.49°C (estimate)
  • Formula C8H9Br
  • Boiling Point 206.9 °C at 760 mmHg
  • Molecular Weight 185.063
  • Flash Point 87.2 °C
  • Transport Information
  • Appearance white to light yellow crystal powder
  • Safety 26-36/37/39-37/39
  • Risk Codes 36/37/38
  • Molecular Structure Molecular Structure of 556-96-7 (5-Bromo-m-xylene)
  • Hazard Symbols IrritantXi
  • Synonyms m-Xylene,5-bromo- (6CI,7CI,8CI);1-Bromo-3,5-dimethylbenzene;1-Bromo-3,5-xylene;3,5-Dimethyl-1-bromobenzene;3,5-Dimethylbromobenzene;3,5-Dimethylphenylbromide;5-Bromo-1,3-xylene;
  • PSA 0.00000
  • LogP 3.06590

Synthetic route

3,5-dimethylaminoaniline
108-69-0

3,5-dimethylaminoaniline

5-bromo-1,3-xylene
556-96-7

5-bromo-1,3-xylene

Conditions
ConditionsYield
With trimethylsilyl bromide; N-benzyl-N,N,N-triethylammonium chloride; sodium nitrite In tetrachloromethane 1.) 0 deg C, 1.5 h, 2.) r.t., 12 h;89%
With hydrogen bromide Diazotization.Behandlung der Diazoniumsalz-Loesung mit CuBr oder mit Kupfer-Pulver;
(i) (diazotization), aq. HBr, (ii) Cu; Multistep reaction;
m-xylene
108-38-3

m-xylene

5-bromo-1,3-xylene
556-96-7

5-bromo-1,3-xylene

Conditions
ConditionsYield
With copper(ll) bromide; aluminum oxide In tetrachloromethane at 80℃; for 2h;85%
With copper(ll) bromide; aluminum oxide In tetrachloromethane at 80℃; for 2h; Product distribution;85%
3,5-dimethylphenyl boronic acid
172975-69-8

3,5-dimethylphenyl boronic acid

5-bromo-1,3-xylene
556-96-7

5-bromo-1,3-xylene

Conditions
ConditionsYield
With 1,10-Phenanthroline; oxygen; potassium bromide; copper(ll) bromide In N,N-dimethyl-formamide at 130℃; for 20h;71%
4-bromo-2,6-dimethylphenylamine
24596-19-8

4-bromo-2,6-dimethylphenylamine

5-bromo-1,3-xylene
556-96-7

5-bromo-1,3-xylene

Conditions
ConditionsYield
Stage #1: 4-bromo-2,6-dimethylphenylamine With sulfuric acid In ethanol at -10 - 20℃; for 1h;
Stage #2: With sodium nitrite In ethanol; water for 1.5h;
Stage #3: With copper In ethanol; water at 20℃;		51%
Stage #1: 4-bromo-2,6-dimethylphenylamine With sulfuric acid In ethanol at 7 - 20℃; for 1h;
Stage #2: With sodium nitrite In ethanol; water at 20℃; for 1.5h; Cooling;
Stage #3: With copper In ethanol; water at 20℃; Inert atmosphere;		51%
Stage #1: 4-bromo-2,6-dimethylphenylamine With sulfuric acid In ethanol at -10 - 20℃;
Stage #2: With sodium nitrite In ethanol; water for 1.5h; Cooling with ice;
Stage #3: With copper In ethanol; water at 20℃;		63.5 g
<(3,5-Dimethylphenyl)azo>pyrrolidine

<(3,5-Dimethylphenyl)azo>pyrrolidine

5-bromo-1,3-xylene
556-96-7

5-bromo-1,3-xylene

Conditions
ConditionsYield
With hydrogen bromide; copper(I) bromide37%
2-bromo-4,6-dimethylaniline
41825-73-4

2-bromo-4,6-dimethylaniline

5-bromo-1,3-xylene
556-96-7

5-bromo-1,3-xylene

Conditions
ConditionsYield
With hydrogenchloride Diazotization.Behandlung der Diazoniumsalz-Loesung mit wss.-alkal. Stannit-Loesung;
2,4-Xylidine
95-68-1

2,4-Xylidine

5-bromo-1,3-xylene
556-96-7

5-bromo-1,3-xylene

Conditions
ConditionsYield
With hydrogenchloride; hydrogen bromide; bromine Behandeln des Reaktionsgemisches mit Natriumnitrit und anschliessend Behandeln mit Zinn(II)-chlorid und wss. Natronlauge;
Multi-step reaction with 2 steps
1: hydrochloric acid; bromine / ueber mehrere Stufen
View Scheme
1-bromo-2,4-dimethylbenzene
583-70-0

1-bromo-2,4-dimethylbenzene

5-bromo-1,3-xylene
556-96-7

5-bromo-1,3-xylene

Conditions
ConditionsYield
With hydrogen fluoride; antimony pentafluoride
2-Bromo-m-xylene
576-22-7

2-Bromo-m-xylene

A

5-bromo-1,3-xylene
556-96-7

5-bromo-1,3-xylene

B

1-bromo-2,4-dimethylbenzene
583-70-0

1-bromo-2,4-dimethylbenzene

Conditions
ConditionsYield
TfOH2+B(OTf)4- In toluene for 18h; Product distribution; Ambient temperature;A 3.5 % Chromat.
B 69.1 % Chromat.
2-Bromo-m-xylene
576-22-7

2-Bromo-m-xylene

A

5-bromo-1,3-xylene
556-96-7

5-bromo-1,3-xylene

B

1-bromo-2,4-dimethylbenzene
583-70-0

1-bromo-2,4-dimethylbenzene

C

m-xylene
108-38-3

m-xylene

Conditions
ConditionsYield
With hydrogen; oxygen at 40℃; under 760 Torr; Product distribution; Mechanism; Irradiation; effect of further reagents;
...Expand
1-bromo-2,4-dimethylbenzene
583-70-0

1-bromo-2,4-dimethylbenzene

A

5-bromo-1,3-xylene
556-96-7

5-bromo-1,3-xylene

B

2-Bromo-m-xylene
576-22-7

2-Bromo-m-xylene

C

m-xylene
108-38-3

m-xylene

Conditions
ConditionsYield
With hydrogen; oxygen at 40℃; under 760 Torr; Product distribution; Mechanism; Irradiation; effect of further reagent;
...Expand
diazotized 5-bromo-4-amino-m-xylene

diazotized 5-bromo-4-amino-m-xylene

5-bromo-1,3-xylene
556-96-7

5-bromo-1,3-xylene

Conditions
ConditionsYield
With sodium hydroxide; tin(ll) chloride
durch Verkochen;
3,6-bis(trifluoromethyl)bromobenzene
328-70-1

3,6-bis(trifluoromethyl)bromobenzene

5-bromo-1,3-xylene
556-96-7

5-bromo-1,3-xylene

Conditions
ConditionsYield
With trityl tetrakis(pentafluorophenyl)borate In 1,2-dichloro-benzene at 22℃; for 24h; Product distribution; Further Variations:; Reagents; Solvents;
With triethylsilane; fluorotris(pentafluorophenyl)phosphonium tetrakis(pentafluorophenyl)borate at 20℃; for 24h;
3,5-dimethylphenyl iodide
22445-41-6

3,5-dimethylphenyl iodide

5-bromo-1,3-xylene
556-96-7

5-bromo-1,3-xylene

Conditions
ConditionsYield
With trans-N,N'-dimethyl-1,2-cyclohexyldiamine; copper(l) iodide; sodium bromide In N,N-dimethyl-formamide at 110℃; for 5h; Product distribution; Further Variations:; Reagents; reaction time; aromatic Finkelstein reaction;
With tetrabutylammomium bromide; trans-N,N'-dimethylcyclohexane-1,2-diamine; copper(l) iodide In DMF (N,N-dimethyl-formamide) at 110℃;
With trans-N,N'-dimethylcyclohexane-1,2-diamine; sodium bromide; copper(l) iodide In DMF (N,N-dimethyl-formamide) at 110℃;
2-(3,5-dimethylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
325142-93-6

2-(3,5-dimethylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

5-bromo-1,3-xylene
556-96-7

5-bromo-1,3-xylene

Conditions
ConditionsYield
With copper(ll) bromide In methanol at 80℃;226 mg
2,6-dimethylaniline
87-62-7

2,6-dimethylaniline

5-bromo-1,3-xylene
556-96-7

5-bromo-1,3-xylene

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: bromine / methanol / 20 °C
2.1: sulfuric acid / ethanol / 1 h / -10 - 20 °C
2.2: 1.5 h
2.3: 20 °C
View Scheme
Multi-step reaction with 2 steps
1.1: bromine / methanol / 20 °C
2.1: sulfuric acid / ethanol / -10 - 20 °C
2.2: 1.5 h / Cooling with ice
2.3: 20 °C
View Scheme
Multi-step reaction with 2 steps
1.1: bromine / methanol / 20 °C
2.1: sulfuric acid / ethanol / 1 h / 7 - 20 °C
2.2: 1.5 h / 20 °C / Cooling
2.3: 20 °C / Inert atmosphere
View Scheme
5-bromo-1,3-xylene
556-96-7

5-bromo-1,3-xylene

phenylboronic acid
98-80-6

phenylboronic acid

3,5-dimethylbiphenyl
17057-88-4

3,5-dimethylbiphenyl

Conditions
ConditionsYield
With potassium phosphate; 3-(2,6-diisopropylphenyl)-1-(2-diphenylphosphanylbenzyl)-3H-imidazol-1-ium chloride; bis(η3-allyl-μ-chloropalladium(II)) In 1,4-dioxane at 80℃; for 12h; Suzuki cross-coupling;100%
With potassium tert-butylate; N,N-dimethylthiocarbamate-phosphine ligand; bis(dibenzylideneacetone)-palladium(0) In dimethyl sulfoxide at 80℃; for 4h; Suzuki cross-coupling reaction;99%
With potassium carbonate In toluene at 110℃; for 2h; Suzuki reaction;99%
5-bromo-1,3-xylene
556-96-7

5-bromo-1,3-xylene

tributylphenylstannane
960-16-7

tributylphenylstannane

3,5-dimethylbiphenyl
17057-88-4

3,5-dimethylbiphenyl

Conditions
ConditionsYield
With 1,4-diaza-bicyclo[2.2.2]octane; tetrabutyl ammonium fluoride; palladium diacetate In 1,4-dioxane at 100℃; for 20h; Stille reaction;100%
With 1,4-diaza-bicyclo[2.2.2]octane; potassium hydroxide; poly(ethylene glycol)-400; palladium diacetate In water at 80℃; for 10h; Stille coupling;93%
With potassium fluoride; 1,4-dicyclohexyl-diazabutadiene; bis(dibenzylideneacetone)-palladium(0) In 1,4-dioxane at 100℃; for 24h; Stille cross-coupling reaction;82%
5-bromo-1,3-xylene
556-96-7

5-bromo-1,3-xylene

1-bromo-3-(bromomethyl)-5-methylbenzene
51719-69-8

1-bromo-3-(bromomethyl)-5-methylbenzene

Conditions
ConditionsYield
With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In tetrachloromethane for 2h; Heating / reflux;100%
With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione; dibenzoyl peroxide In tetrachloromethane for 7h; Product distribution / selectivity; Reflux;99%
With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione; dibenzoyl peroxide In tetrachloromethane for 7h; Product distribution / selectivity; Reflux;99%
5-bromo-1,3-xylene
556-96-7

5-bromo-1,3-xylene

3,5-dimethylaminoaniline
108-69-0

3,5-dimethylaminoaniline

Conditions
ConditionsYield
With copper(I) oxide; ammonium hydroxide In 1-methyl-pyrrolidin-2-one at 80℃; for 15h;100%
With copper(l) iodide; 2-carboxyquinoline N-oxide; potassium carbonate; ammonium hydroxide In dimethyl sulfoxide at 80℃; for 23h; Inert atmosphere;91%
With copper(l) iodide; ammonia; sodium phosphate In water at 100℃; for 24h;86%
With diethylenetriaminopentaacetic acid; ammonia; copper(II) oxide; potassium hydroxide In water at 100℃; for 6h;74%
Stage #1: 5-bromo-1,3-xylene With magnesium In tetrahydrofuran Inert atmosphere;
Stage #2: With C10H17NO In tetrahydrofuran; toluene at -78℃; for 2h; Inert atmosphere;
Stage #3: With ammonium chloride In tetrahydrofuran; water; toluene Inert atmosphere;		74%
triisopropyl phosphite
116-17-6

triisopropyl phosphite

5-bromo-1,3-xylene
556-96-7

5-bromo-1,3-xylene

C14H23O3P
1393678-00-6

C14H23O3P

Conditions
ConditionsYield
With nickel dibromide at 150℃; for 3h; Inert atmosphere;100%
fur-2-ylboronic acid
13331-23-2

fur-2-ylboronic acid

5-bromo-1,3-xylene
556-96-7

5-bromo-1,3-xylene

2-(3,5-dimethylphenyl)furan

2-(3,5-dimethylphenyl)furan

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); caesium carbonate In methanol; toluene at 100℃; for 16h; Inert atmosphere;100%
With tetrakis(triphenylphosphine) palladium(0); caesium carbonate In methanol; toluene at 100℃; for 3h;
diethylphosphoramidous dichloride
1069-08-5

diethylphosphoramidous dichloride

5-bromo-1,3-xylene
556-96-7

5-bromo-1,3-xylene

bis-(3,5-dimethylphenyl)chlorophosphine
74289-57-9

bis-(3,5-dimethylphenyl)chlorophosphine

Conditions
ConditionsYield
Stage #1: 5-bromo-1,3-xylene With n-butyllithium In diethyl ether; hexane at 0℃; for 4h; Inert atmosphere; Sealed tube;
Stage #2: diethylphosphoramidous dichloride In diethyl ether; hexane at 0℃; for 0.166667h; Inert atmosphere; Sealed tube;
Stage #3: With hydrogenchloride In 1,4-dioxane; diethyl ether; hexane Inert atmosphere; Sealed tube;		100%
5-bromo-1,3-xylene
556-96-7

5-bromo-1,3-xylene

3,3',5,5'-tetramethyl-1,1'-biphenyl
25570-02-9

3,3',5,5'-tetramethyl-1,1'-biphenyl

Conditions
ConditionsYield
With (1E,2E)-N1,N2-bis(2,6-dimethylphenyl)ethane-1,2-diimine; nickel dibromide; zinc In tetrahydrofuran at 70℃; for 10h; Inert atmosphere;99%
With indium; tetrakis(triphenylphosphine) palladium(0) In N,N-dimethyl-formamide at 100℃; for 48h;88.6%
Stage #1: 5-bromo-1,3-xylene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 2h;
Stage #2: With copper dichloride In tetrahydrofuran; hexane at -78 - 20℃; for 1h;		65%
With thallium(I) bromide; magnesium 1.) THF, reflux, 2.) THF, benzene, reflux, 4 h;
5-bromo-1,3-xylene
556-96-7

5-bromo-1,3-xylene

1-Naphthylboronic acid
13922-41-3

1-Naphthylboronic acid

1-(3,5-dimethylphenyl)naphthalene
164172-87-6

1-(3,5-dimethylphenyl)naphthalene

Conditions
ConditionsYield
With potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0); dicyclohexyl(1-(naphtho[2,3-b]furan-9-yl)naphthalen-2-yl)phosphine In toluene at 80℃; for 0.5h; Suzuki-Miyaura Coupling; Inert atmosphere; Schlenk technique;99%
With palladium diacetate; 5A molecular sieve; triethylamine; tris-(o-tolyl)phosphine In N,N-dimethyl-formamide at 100℃; for 4h;73%
1H-imidazole
288-32-4

1H-imidazole

5-bromo-1,3-xylene
556-96-7

5-bromo-1,3-xylene

1-(3,5-dimethylphenyl)-1H-imidazole
223762-69-4

1-(3,5-dimethylphenyl)-1H-imidazole

Conditions
ConditionsYield
With copper(I) trifluoromethanesulfonate benzene; caesium carbonate; 1,10-Phenanthroline; (dibenzylidene)acetone In xylene at 125℃; for 36h; Substitution;99%
With caesium carbonate In dimethyl sulfoxide at 120℃; Inert atmosphere;95%
With copper(I) oxide; 1,10-Phenanthroline; tetrabutyl ammonium fluoride at 140 - 145℃; for 24h;86%
With copper(l) iodide; 8-quinolinol; caesium carbonate In water; N,N-dimethyl-formamide at 130℃; for 16h;
With potassium phosphate; copper(l) iodide; tetrabutylammomium bromide; 1,10-phenanthroline-4,7-diol In water at 100℃; for 24h; Ullmann Condensation; Schlenk technique; Inert atmosphere; Green chemistry;73 %Chromat.
morpholine
110-91-8

morpholine

5-bromo-1,3-xylene
556-96-7

5-bromo-1,3-xylene

N (dimethyl-3,5-phenyl-1) morpholine
16800-77-4

N (dimethyl-3,5-phenyl-1) morpholine

Conditions
ConditionsYield
With [Pd(N,N'-bis(2,6-bis(di-p-tolylmethyl)-4-methylphenyl)-imidazol-2-ylidene)(acetylacetonate)Cl]; lithium hexamethyldisilazane In 1,4-dioxane at 110℃; for 3h; Buchwald-Hartwig Coupling; Inert atmosphere; Sealed tube;99%
With bis(tri-t-butylphosphine)palladium(0); potassium tert-butylate In toluene at 20℃; for 4h;99%
With potassium tert-butylate; johnphos; tris(dibenzylideneacetone)dipalladium (0) In tetrahydrofuran at 20℃; for 20h; Arylation;80%
With copper(l) iodide; potassium carbonate; L-proline In dimethyl sulfoxide at 90℃; for 24h;56%
Benzophenone imine
1013-88-3

Benzophenone imine

5-bromo-1,3-xylene
556-96-7

5-bromo-1,3-xylene

N-(3,5-dimethylphenyl)-1,1-diphenylmethanimine
384344-10-9

N-(3,5-dimethylphenyl)-1,1-diphenylmethanimine

Conditions
ConditionsYield
With potassium tert-butylate; bis(dibenzylideneacetone)-palladium(0); 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride In 1,4-dioxane at 100℃; for 10h;99%
5-bromo-1,3-xylene
556-96-7

5-bromo-1,3-xylene

thiophenol
108-98-5

thiophenol

3,5-dimethylphenyl phenyl sulfide

3,5-dimethylphenyl phenyl sulfide

Conditions
ConditionsYield
With 1,1'-bis-(diphenylphosphino)ferrocene; tris-(dibenzylideneacetone)dipalladium(0); N-ethyl-N,N-diisopropylamine In toluene for 3h; Inert atmosphere; Reflux;99%
With (IPr)Ni(π-allyl)Cl; sodium t-butanolate In N,N-dimethyl-formamide at 100℃; for 24h; Inert atmosphere;95%
Stage #1: 5-bromo-1,3-xylene; thiophenol With sodium iodide; N,N`-dimethylethylenediamine; copper(l) iodide In toluene at 110℃; for 24h;
Stage #2: With potassium carbonate; ethylene glycol In isopropyl alcohol at 80℃; for 18 - 20h;		93%
With copper(l) iodide; 2,2',2''-triaminotriethylamine; caesium carbonate In 1,4-dioxane at 110℃; for 23h;82%
With copper(l) iodide; caesium carbonate In 1-methyl-pyrrolidin-2-one at 195℃; for 6h; microwave irradiation;73%
Octanethiol
111-88-6

Octanethiol

5-bromo-1,3-xylene
556-96-7

5-bromo-1,3-xylene

3,5-dimethylphenyl octyl sulfide
1264694-60-1

3,5-dimethylphenyl octyl sulfide

Conditions
ConditionsYield
With 1,1'-bis-(diphenylphosphino)ferrocene; tris-(dibenzylideneacetone)dipalladium(0); N-ethyl-N,N-diisopropylamine In toluene for 3h; Inert atmosphere; Reflux;99%
5-bromo-1,3-xylene
556-96-7

5-bromo-1,3-xylene

benzene
71-43-2

benzene

3,5-dimethylbiphenyl
17057-88-4

3,5-dimethylbiphenyl

Conditions
ConditionsYield
With C34H52Cl2N2Pd; potassium carbonate; Trimethylacetic acid In N,N-dimethyl acetamide at 120℃; for 16h;99%
With dichloro bis(acetonitrile) palladium(II); potassium carbonate; Trimethylacetic acid In N,N-dimethyl acetamide at 120℃; for 18h; Mechanism; Reagent/catalyst;96%
With 2-Hydroxymethylpyridine; potassium tert-butylate at 20 - 80℃; for 24h; Schlenk technique; Inert atmosphere;69%
styrene
292638-84-7

styrene

5-bromo-1,3-xylene
556-96-7

5-bromo-1,3-xylene

(E/Z)-3,5-Dimethylstilbene
172878-95-4

(E/Z)-3,5-Dimethylstilbene

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 9h; Heck reaction;99%
With 1-methyl-pyrrolidin-2-one; potassium phosphate; [Pd(OAc)(1,3,5-triphenyl pyrazole(-H))]2; tetrabutylammomium bromide at 160℃; for 30h; Heck Reaction; Inert atmosphere;93%
With C19H13N3O2Pd; potassium carbonate In methanol for 2h; Reagent/catalyst; Heck Reaction; Reflux;81%
5-bromo-1,3-xylene
556-96-7

5-bromo-1,3-xylene

4-methoxyphenylboronic acid
5720-07-0

4-methoxyphenylboronic acid

4′-methoxy-3,5-dimethyl-1,1′-biphenyl

4′-methoxy-3,5-dimethyl-1,1′-biphenyl

Conditions
ConditionsYield
With bis-triphenylphosphine-palladium(II) chloride; potassium carbonate In ethanol; water; toluene for 14h; Suzuki-Miyaura Coupling; Inert atmosphere; Reflux;99%
5-bromo-1,3-xylene
556-96-7

5-bromo-1,3-xylene

ethylene glycol
107-21-1

ethylene glycol

2-(3,5-dimethylphenoxy)ethanol
5960-05-4

2-(3,5-dimethylphenoxy)ethanol

Conditions
ConditionsYield
With potassium carbonate; copper dichloride at 130℃; for 20h; Inert atmosphere; Schlenk technique;99%
5-methylbenzofuran
18441-43-5

5-methylbenzofuran

5-bromo-1,3-xylene
556-96-7

5-bromo-1,3-xylene

5-methyl-2-(3,5-dimethylphenyl)benzoxazole
920133-32-0

5-methyl-2-(3,5-dimethylphenyl)benzoxazole

Conditions
ConditionsYield
With C13H18Cl2N4OPd; lithium tert-butoxide In N,N-dimethyl-formamide at 130℃; for 24h; Catalytic behavior; Inert atmosphere; Schlenk technique;99%
5-bromo-1,3-xylene
556-96-7

5-bromo-1,3-xylene

zinc(II) chloride
7646-85-7

zinc(II) chloride

(3,5-dimethylphenyl)zinc chloride

(3,5-dimethylphenyl)zinc chloride

Conditions
ConditionsYield
Stage #1: 5-bromo-1,3-xylene With magnesium; lithium chloride In tetrahydrofuran at 25℃; Schlenk technique; Inert atmosphere;
Stage #2: zinc(II) chloride In tetrahydrofuran at 0 - 25℃; for 0.25h; Schlenk technique; Inert atmosphere;		99%
Stage #1: 5-bromo-1,3-xylene With n-butyllithium In tetrahydrofuran at -78℃; for 1h;
Stage #2: zinc(II) chloride In tetrahydrofuran at 20℃; for 1.5h;
5-bromo-1,3-xylene
556-96-7

5-bromo-1,3-xylene

trimethylsilylacetylene
1066-54-2

trimethylsilylacetylene

3,5-dimethyl-1-(trimethylsilylethynyl)benzene
276856-72-5

3,5-dimethyl-1-(trimethylsilylethynyl)benzene

Conditions
ConditionsYield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine at 100℃; for 24h;98.5%
With CuI; diisopropylamine; triphenylphosphine; Pd(PPh3)2Cl2
NH-pyrazole
288-13-1

NH-pyrazole

5-bromo-1,3-xylene
556-96-7

5-bromo-1,3-xylene

1-(3,5-dimethylphenyl)-1H-pyrazole

1-(3,5-dimethylphenyl)-1H-pyrazole

Conditions
ConditionsYield
With caesium carbonate In dimethyl sulfoxide at 120℃; Inert atmosphere;98.2%
With sodium t-butanolate; tert-butyl XPhos; tris-(dibenzylideneacetone)dipalladium(0) In toluene at 80℃; for 22h;88%
5-bromo-1,3-xylene
556-96-7

5-bromo-1,3-xylene

cyclohexylamine
108-91-8

cyclohexylamine

N-(3,5-dimethylphenyl)cyclohexylamine
13342-30-8

N-(3,5-dimethylphenyl)cyclohexylamine

Conditions
ConditionsYield
With C60H86O4P2Pd2(2+)*2BF4(1-); sodium t-butanolate In 1,4-dioxane at 100℃; for 3h;98%
With tris-(dibenzylideneacetone)dipalladium(0); potassium tert-butylate; (S)-(1,1'-binaphthalene)-2,2'-diylbis(diphenylphosphine) In toluene at 80℃; for 18h; Arylation;85%
With tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate In toluene at 80℃; for 18h;83%
acrylic acid n-butyl ester
141-32-2

acrylic acid n-butyl ester

5-bromo-1,3-xylene
556-96-7

5-bromo-1,3-xylene

(E)-n-butyl 3-(3,5-dimethylphenyl)acrylate

(E)-n-butyl 3-(3,5-dimethylphenyl)acrylate

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 140℃; for 12h; Heck reaction;98%
With trans-1,2-cyclohexanediamine-based Pd; cetyltrimethylammonim bromide; potassium carbonate In N,N-dimethyl acetamide at 160℃; for 5h; Heck cross-coupling reaction;88%
With cetyltrimethylammonim bromide; sodium carbonate; binaphthyl-based palladium In N,N-dimethyl acetamide at 160℃; for 18h; Heck cross-coupling;86%
5-bromo-1,3-xylene
556-96-7

5-bromo-1,3-xylene

sodium cyanide
143-33-9

sodium cyanide

3,5-dimethylbenzonitrile
22445-42-7

3,5-dimethylbenzonitrile

Conditions
ConditionsYield
With N,N`-dimethylethylenediamine In toluene at 90℃; for 24h; Rosenmund-von Braun reaction;98%
Stage #1: 5-bromo-1,3-xylene; sodium cyanide With potassium iodide; N,N`-dimethylethylenediamine; copper(l) iodide In toluene at 110℃; for 24h;
Stage #2: With ammonia In dodecane; water; ethyl acetate; toluene at 25℃; for 0.166667h;		86 - 90 %Chromat.
Stage #1: 5-bromo-1,3-xylene; sodium cyanide With potassium iodide; N,N`-dimethylethylenediamine; copper(l) iodide In toluene; benzyl alcohol at 110℃; for 12h;
Stage #2: With ammonia In dodecane; water; ethyl acetate; toluene; benzyl alcohol at 25℃; for 0.166667h;		88 %Chromat.
5-bromo-1,3-xylene
556-96-7

5-bromo-1,3-xylene

o-(phenylethynyl)trifluoroacetanilide
143360-89-8

o-(phenylethynyl)trifluoroacetanilide

3-(3,5-dimethyl-phenyl)-2-phenyl-1H-indole

3-(3,5-dimethyl-phenyl)-2-phenyl-1H-indole

Conditions
ConditionsYield
With caesium carbonate; tetrakis(triphenylphosphine) palladium(0) In acetonitrile at 100℃; for 0.5h;98%
With caesium carbonate; tetrakis(triphenylphosphine) palladium(0) In acetonitrile at 100℃; for 3h;98%
5-bromo-1,3-xylene
556-96-7

5-bromo-1,3-xylene

phenyl trimethylsiloxane
2996-92-1

phenyl trimethylsiloxane

3,5-dimethylbiphenyl
17057-88-4

3,5-dimethylbiphenyl

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride; tris-(o-tolyl)phosphine; dichloro bis(acetonitrile) palladium(II) at 80℃; for 0.583333h; Hiyama cross-coupling reaction;98%
With 1,4-diaza-bicyclo[2.2.2]octane; tetrabutyl ammonium fluoride; palladium diacetate In 1,4-dioxane at 80℃; for 4h; Hiyama cross-coupling reaction;60%
indole
120-72-9

indole

CuOAc

CuOAc

5-bromo-1,3-xylene
556-96-7

5-bromo-1,3-xylene

(R)-1-phenyl-ethyl-amine
3886-69-9

(R)-1-phenyl-ethyl-amine

N,N-diethylsalicylamide
19311-91-2

N,N-diethylsalicylamide

(R)-α-methyl-N-(3,5-dimethylphenyl)benzylamine

(R)-α-methyl-N-(3,5-dimethylphenyl)benzylamine

Conditions
ConditionsYield
With ammonium hydroxide; potassium phosphate In dodecane; hexane; water; ethyl acetate; N,N-dimethyl-formamide98%
...Expand
carbon monoxide
201230-82-2

carbon monoxide

5-bromo-1,3-xylene
556-96-7

5-bromo-1,3-xylene

benzylamine
100-46-9

benzylamine

N-benzyl-3,5-dimethylbenzamide

N-benzyl-3,5-dimethylbenzamide

Conditions
ConditionsYield
With palladium diacetate; sodium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In toluene at 80℃; under 760.051 Torr; for 15h;98%
...Expand
2-thienyl chloride
96-43-5

2-thienyl chloride

5-bromo-1,3-xylene
556-96-7

5-bromo-1,3-xylene

2-chloro-5-(3,5-dimethylphenyl)thiophene
1353658-84-0

2-chloro-5-(3,5-dimethylphenyl)thiophene

Conditions
ConditionsYield
With 2'-(PdPCy3Cl)-2-Aminobiphenyl; potassium carbonate; Trimethylacetic acid at 100℃; Inert atmosphere;98%

5-Bromo-m-xylene Chemical Properties

Molecule structure of 3,5-Dimethylbromobenzene (CAS NO.556-96-7) :

IUPAC Name: 1-bromo-3,5-dimethylbenzene 
Molecular Weight: 185.06106 g/mol
Molecular Formula: C8H9Br 
Density: 1.339 g/cm3 
Boiling Point: 206.9 °C at 760 mmHg 
Flash Point: 87.2 °C
Appreance: white to light yellow crystal powder
Index of Refraction: 1.543
Molar Refractivity: 43.59 cm3
Molar Volume: 138.1 cm3
Polarizability: 17.28*10-24 cm3
Surface Tension: 33.7 dyne/cm 
Enthalpy of Vaporization: 42.5 kJ/mol
Vapour Pressure: 0.333 mmHg at 25 °C 
log P (octanol-water): 3.980 
Atmospheric OH Rate Constant 8.64E-12 cm3/molecule-sec 
XLogP3: 3.4
Exact Mass: 183.988763
MonoIsotopic Mass: 183.988763
Heavy Atom Count: 9
Complexity: 80.6
Canonical SMILES: CC1=CC(=CC(=C1)Br)C
InChI: InChI=1S/C8H9Br/c1-6-3-7(2)5-8(9)4-6/h3-5H,1-2H3
InChIKey: LMFRTSBQRLSJHC-UHFFFAOYSA-N
Product Categories of 3,5-Dimethylbromobenzene (CAS NO.556-96-7) : Aromatic Hydrocarbons (substituted) & Derivatives; Halogen toluene; Benzene derivates; Miscellaneous; Bromine Compounds

5-Bromo-m-xylene Safety Profile

Hazard Codes: Xi
Risk Statements: 36/37/38 
R36/37/38: Irritating to eyes, respiratory system and skin
Safety Statements: 26-36/37/39-37/39 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice 
S36/37/39: Wear suitable protective clothing, gloves and eye/face protection 
S37/39: Wear suitable gloves and eye/face protection
WGK Germany: 3
Hazard Note: Irritant
HS Code: 29036990

5-Bromo-m-xylene Specification

 3,5-Dimethylbromobenzene (CAS NO.556-96-7)  is also called 5-Bromo-1,3-xylene ; m-Xylene, 5-bromo- ; 5-Bromo-m-xylene ; 5-Bromometaxylene ; 5-Bromo-3,5-dimethylbenzene ; 1-Bromo-3,5-dimethylbenzene .

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