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556-96-7 Usage

Chemical Properties

white to light yellow crystal powder

Uses

Different sources of media describe the Uses of 556-96-7 differently. You can refer to the following data:
1. 5-Bromo-m-xylene has been used in the synthesis of substituted 2,2′-bis(diphenylphosphanylmethyl)-1,1′-binaphthyl derivatives.
2. 5-Bromo-m-xylene is used in the preparation of substituted 2,2'-bis(diphenylphosphanylmethyl)-1,1'-binaphthyl derivatives. It is also used to prepare o-tolyl-3,5-xylyl ether by reacting with o-cresol. Further, it is an organic building block used in the synthesis of various chemicals as well as in the preparation of tri-o-tolylphosphine.
3. 1-Bromo-3,5-dimethylbenzene has been used in the synthesis of substituted 2,2′-bis(diphenylphosphanylmethyl)-1,1′-binaphthyl derivatives.

General Description

Palladium catalyzed carbon-oxygen coupling of 1-bromo-3,5-dimethylbenzene and o-cresol to potassium hydroxide to produce o-tolyl-3,5-xylyl ether has been reported.

Check Digit Verification of cas no

The CAS Registry Mumber 556-96-7 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,5 and 6 respectively; the second part has 2 digits, 9 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 556-96:
(5*5)+(4*5)+(3*6)+(2*9)+(1*6)=87
87 % 10 = 7
So 556-96-7 is a valid CAS Registry Number.
InChI:InChI=1/C8H9Br/c1-6-3-7(2)5-8(9)4-6/h3-5H,1-2H3

556-96-7 Well-known Company Product Price

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  • Alfa Aesar

  • (B21610)  5-Bromo-m-xylene, 98%   

  • 556-96-7

  • 5g

  • 204.0CNY

  • Detail
  • Alfa Aesar

  • (B21610)  5-Bromo-m-xylene, 98%   

  • 556-96-7

  • 25g

  • 381.0CNY

  • Detail
  • Alfa Aesar

  • (B21610)  5-Bromo-m-xylene, 98%   

  • 556-96-7

  • 100g

  • 1313.0CNY

  • Detail

556-96-7SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 15, 2017

Revision Date: Aug 15, 2017

1.Identification

1.1 GHS Product identifier

Product name 5-Bromo-m-xylene

1.2 Other means of identification

Product number -
Other names 1-bromo-3,5-dimethylbenzene

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:556-96-7 SDS

556-96-7Synthetic 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;
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;
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%
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%
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%

556-96-7Relevant articles and documents

Catalyst

-

Paragraph 0426; 0467-0470, (2021/03/16)

A complex of formula (I): (I′) M is Hf; each X is a sigma ligand; L is a bridge of formula -(ER82)y—; y is 1 or 2; E is C or Si; each R8 is independently a C1-C20-hydrocarbyl, tri(C1-C20-alkyl)silyl, C6-C20- aryl, C7-C20-arylalkyl or C7-C20-alkylaryl or L is an alkylene group such as methylene or ethylene; Ar and Ar′ are each independently an aryl or heteroaryl group optionally substituted by 1 to 3 groups R1 or R1′ respectively; R1 and R1′ are each independently the same or can be different and are a linear or branched C1-C6-alkyl group, C7-20 arylalkyl, C7-20 alkylaryl group or C6-20 aryl group with the proviso that if there are four or more R1 and R1′ groups present in total, one or more of R1 and R1′ is other than tert butyl; R2 and R2′ are the same or are different and are a CH2—R9 group, with R9 being H or linear or branched C1-C6-alkyl group, C3-8 cycloalkyl group, C6-10 aryl group; each R is a —CH2—, —CHRx- or C(Rx)2-group wherein Rx is C1-4 alkyl and where m is 2-6; R5 is a linear or branched C1-C6-alkyl group, C7-20 arylalkyl, C7-20 alkylaryl group or C6-C20-aryl group; R6 is a C(R10)3 group, with R10 being a linear or branched C1-C6 alkyl group; and R6 and R7′ are the same or are different and are H or a linear or branched C1-C6-alkyl group. Invention relates also to a catalyst in solid form comprising (i) a complex of formula (I) and (ii) a cocatalyst of an aluminium compound and (iii) a cocatalyst of a boron compound.

PROCESS FOR PREPARING PROPYLENE COPOLYMERS COMPRISING C4-C12-ALPHA OLEFIN COMONOMER UNITS

-

Page/Page column 59-60, (2020/01/10)

The present invention relates to a process for producing a copolymer of propylene, optionally ethylene, and at least one comonomer selected from alpha olefins having from 4 to 12 carbon atoms using a specific class of metallocene complexes in combination with a cocatalyst system comprising a boron containing cocatalyst and an aluminoxane cocatalyst, preferably in a multistage polymerization process including a gas phase polymerization step.

Lewis acidity of organofluorophosphonium salts: Hydrodefluorination by a saturated acceptor

Caputo, Christopher B.,Hounjet, Lindsay J.,Dobrovetsky, Roman,Stephan, Douglas W.

, p. 1374 - 1377 (2013/10/08)

Prototypical Lewis acids, such as boranes, derive their reactivity from electronic unsaturation. Here, we report the Lewis acidity and catalytic application of electronically saturated phosphorus-centered electrophilic acceptors. Organofluorophosphonium salts of the formula [(C6F 5)3-xPhxPF][B(C6F5) 4] (x = 0 or 1; Ph, phenyl) are shown to form adducts with neutral Lewis bases and to react rapidly with fluoroalkanes to produce difluorophosphoranes. In the presence of hydrosilane, the cation [(C 6F5)3PF]+ is shown to catalyze the hydrodefluorination of fluoroalkanes, affording alkanes and fluorosilane. The mechanism demonstrates the impressive fluoride ion affinity of this highly electron-deficient phosphonium center.

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