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553-94-6 Usage

Chemical Properties

Clear colourless to light yellow liquid

Uses

2-Bromo-1,4-dimethylbenzene was used in the synthesis of 2,5,2′,5′-tetrakismethylbiphenyl via Yamamoto coupling reaction. It was also used in the synthesis of cis-3,4-diphenyl-5,8-dimethylisocoumarins.

Check Digit Verification of cas no

The CAS Registry Mumber 553-94-6 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 3 respectively; the second part has 2 digits, 9 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 553-94:
(5*5)+(4*5)+(3*3)+(2*9)+(1*4)=76
76 % 10 = 6
So 553-94-6 is a valid CAS Registry Number.
InChI:InChI=1/C8H9Br/c1-6-3-4-7(2)8(9)5-6/h3-5H,1-2H3

553-94-6 Well-known Company Product Price

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  • Alfa Aesar

  • (A14358)  2-Bromo-p-xylene, 98+%   

  • 553-94-6

  • 25g

  • 744.0CNY

  • Detail
  • Alfa Aesar

  • (A14358)  2-Bromo-p-xylene, 98+%   

  • 553-94-6

  • 100g

  • 1960.0CNY

  • Detail
  • Alfa Aesar

  • (A14358)  2-Bromo-p-xylene, 98+%   

  • 553-94-6

  • 500g

  • 9045.0CNY

  • Detail

553-94-6SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 14, 2017

Revision Date: Aug 14, 2017

1.Identification

1.1 GHS Product identifier

Product name 2,5-Dimethylbromobenzene

1.2 Other means of identification

Product number -
Other names 2-bromo-1,4-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:553-94-6 SDS

553-94-6Synthetic route

para-xylene
106-42-3

para-xylene

4-bromo-m-xylene
553-94-6

4-bromo-m-xylene

Conditions
ConditionsYield
With potassium bromide; sodium nitrite In water; trifluoroacetic acid at 20℃; for 0.16h; Product distribution; under argon;100%
With oxygen; potassium bromide; sodium nitrite In water; trifluoroacetic acid at 20℃; for 5h; Product distribution;96%
With sulfuric acid; dihydrogen peroxide; sodium bromide In water at 49.84℃;94%
para-xylene
106-42-3

para-xylene

A

4-bromo-m-xylene
553-94-6

4-bromo-m-xylene

B

2,5-dibromo-p-xylene
1074-24-4

2,5-dibromo-p-xylene

Conditions
ConditionsYield
With carbon dioxide; bromine at 40℃; under 187519 Torr; for 2h; Supercritical conditions; Green chemistry;A 92%
B 8%
With aluminum oxide; bromine for 0.0166667h; Ambient temperature; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
With N-Bromosuccinimide at 20℃; for 16h; Overall yield = 85 %Spectr.; regioselective reaction;
para-xylene
106-42-3

para-xylene

A

4-bromo-m-xylene
553-94-6

4-bromo-m-xylene

B

2,5-dibromo-p-xylene
1074-24-4

2,5-dibromo-p-xylene

C

4-Methylbenzyl bromide
104-81-4

4-Methylbenzyl bromide

Conditions
ConditionsYield
With bromine; acetic acidA 77%
B 10%
C 13%
With bromineA 48%
B n/a
C n/a
para-xylene
106-42-3

para-xylene

A

4-bromo-m-xylene
553-94-6

4-bromo-m-xylene

B

4-Methylbenzyl bromide
104-81-4

4-Methylbenzyl bromide

Conditions
ConditionsYield
With sodium bromate; sodium hydrogensulfite In water; acetonitrile at 20℃; for 4h; Bromination;A 62%
B n/a
With bromine; bentonite In carbon disulfide for 4h; Heating;A 50%
B 30%
With N-Bromosuccinimide In methanol at 150℃; under 2625.26 Torr; for 0.0666667h; microwave irradiation;A 27 % Chromat.
B 32 % Chromat.
With hydrogen bromide; dihydrogen peroxide In water at 20℃; for 24h; Darkness;A 66 %Spectr.
B 14 %Spectr.
With N-Bromosuccinimide; silver hexafluoroantimonate; adamantan-1-yl(methyl)sulfane In 1,2-dichloro-ethane at 20℃; for 1h; Inert atmosphere; Schlenk technique;A 50 %Chromat.
B 20 %Chromat.
1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,5-dimethylbenzene
356570-53-1

1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,5-dimethylbenzene

4-bromo-m-xylene
553-94-6

4-bromo-m-xylene

Conditions
ConditionsYield
With copper(ll) bromide In methanol Heating;46%
2,5-Dimethylaniline
95-78-3

2,5-Dimethylaniline

4-bromo-m-xylene
553-94-6

4-bromo-m-xylene

Conditions
ConditionsYield
With hydrogen bromide diazotization;40%
(i) (diazotization), aq. HBr, (ii) Cu; Multistep reaction;
Methyl fluoride
593-53-3

Methyl fluoride

2-methylphenyl bromide
95-46-5

2-methylphenyl bromide

A

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

2-Bromo-m-xylene

B

4-bromo-m-xylene
553-94-6

4-bromo-m-xylene

C

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

1-bromo-2,4-dimethylbenzene

D

2,3-dimethylbromobenzene
576-23-8

2,3-dimethylbromobenzene

Conditions
ConditionsYield
With oxygen at 40℃; under 720 Torr; Mechanism; Irradiation;A n/a
B n/a
C 13.7%
D 32.8%
2,5-dimethylbenzenesulfonic acid
609-54-1

2,5-dimethylbenzenesulfonic acid

4-bromo-m-xylene
553-94-6

4-bromo-m-xylene

Conditions
ConditionsYield
With copper(ll) bromide
2,2,2-trifluoroethanol
75-89-8

2,2,2-trifluoroethanol

(E)-1,4-Dimethyl-1,3-hexadien-5-in-1-yl-triflat
93362-61-9

(E)-1,4-Dimethyl-1,3-hexadien-5-in-1-yl-triflat

A

4-bromo-m-xylene
553-94-6

4-bromo-m-xylene

B

(4-Methylbenzyl)-(2,2,2-trifluorethyl)-ether
79644-39-6

(4-Methylbenzyl)-(2,2,2-trifluorethyl)-ether

C

(Z)-3-Methyl-hept-3-ene-1,5-diyne
79644-36-3

(Z)-3-Methyl-hept-3-ene-1,5-diyne

D

(2,5-Dimethylphenyl)-(2,2,2-trifluorethyl)-ether
79644-38-5

(2,5-Dimethylphenyl)-(2,2,2-trifluorethyl)-ether

Conditions
ConditionsYield
With 1,3,5-triisopropyl benzene; sodium carbonate; lithium bromide In 1,4-dioxane; water at 120℃; for 120h; Mechanism; Product distribution;A 17 % Chromat.
B 14 % Chromat.
C n/a
D 14 % Chromat.
para-xylene
106-42-3

para-xylene

A

4-bromo-m-xylene
553-94-6

4-bromo-m-xylene

B

2,6-dibromo-1,4-dimethylbenzene
66788-13-4

2,6-dibromo-1,4-dimethylbenzene

Conditions
ConditionsYield
With aluminum oxide; copper(ll) bromide In tetrachloromethane at 80℃; for 1.5h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
para-xylene
106-42-3

para-xylene

A

4-Methylbenzyl alcohol
589-18-4

4-Methylbenzyl alcohol

B

4-bromo-m-xylene
553-94-6

4-bromo-m-xylene

C

1,4-dimethyl-2-(4-methylbenzyl)benzene
721-45-9

1,4-dimethyl-2-(4-methylbenzyl)benzene

D

4-methyl-benzaldehyde
104-87-0

4-methyl-benzaldehyde

Conditions
ConditionsYield
With sulfuric acid; hydrogen bromide In water; acetic acid at 90℃; for 1h; Product distribution; Mechanism; other solvent, effect of the absence of HBr;A 65 % Chromat.
B 30 % Chromat.
C 71 % Chromat.
D 22 % Chromat.
3-methylbicyclo<4.1.0>hepta-1,3,5-triene
75366-05-1

3-methylbicyclo<4.1.0>hepta-1,3,5-triene

A

4-bromo-m-xylene
553-94-6

4-bromo-m-xylene

B

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

1-bromo-2,4-dimethylbenzene

Conditions
ConditionsYield
With bromine; tri-n-butyl-tin hydride Product distribution; Mechanism; multistep reaction; reaction regioselectivity; a series of reagents;
(E)-1,4-Dimethyl-1,3-hexadien-5-in-1-yl-triflat
93362-61-9

(E)-1,4-Dimethyl-1,3-hexadien-5-in-1-yl-triflat

A

4-bromo-m-xylene
553-94-6

4-bromo-m-xylene

B

(4-Methylbenzyl)-(2,2,2-trifluorethyl)-ether
79644-39-6

(4-Methylbenzyl)-(2,2,2-trifluorethyl)-ether

C

(2,5-Dimethylphenyl)-(2,2,2-trifluorethyl)-ether
79644-38-5

(2,5-Dimethylphenyl)-(2,2,2-trifluorethyl)-ether

D

2,5-dimethylphenyl trifluoromethanesulfonate
79644-40-9

2,5-dimethylphenyl trifluoromethanesulfonate

Conditions
ConditionsYield
With 2,2,2-trifluoroethanol; sodium carbonate; lithium bromide In 1,4-dioxane; water at 100℃; for 120h; Further byproducts given;A 16.6 % Chromat.
B 41.2 % Chromat.
C 14.4 % Chromat.
D 1 % Chromat.
para-xylene
106-42-3

para-xylene

iodine
7553-56-2

iodine

4-bromo-m-xylene
553-94-6

4-bromo-m-xylene

Conditions
ConditionsYield
beim Bromieren;
para-xylene
106-42-3

para-xylene

iodine
7553-56-2

iodine

A

4-bromo-m-xylene
553-94-6

4-bromo-m-xylene

B

2,5-dibromo-p-xylene
1074-24-4

2,5-dibromo-p-xylene

Conditions
ConditionsYield
beim Bromieren;
para-xylene
106-42-3

para-xylene

iodine
7553-56-2

iodine

A

4-bromo-m-xylene
553-94-6

4-bromo-m-xylene

B

2,5-dibromo-p-xylene
1074-24-4

2,5-dibromo-p-xylene

C

2,3,5,6-tetrabromo-p-xylene
23488-38-2

2,3,5,6-tetrabromo-p-xylene

Conditions
ConditionsYield
beim Bromieren;
diazotized 2-amino-p-xylene

diazotized 2-amino-p-xylene

4-bromo-m-xylene
553-94-6

4-bromo-m-xylene

Conditions
ConditionsYield
With hydrogen bromide; copper(I) bromide
2,5-Dimethylphenol
95-87-4

2,5-Dimethylphenol

platinum

platinum

4-bromo-m-xylene
553-94-6

4-bromo-m-xylene

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 93 percent / pyridine / CH2Cl2 / 0.25 h / 0 °C
2: 99 percent / Et3N / PdCl2(dppf) / dioxane / Heating
3: 46 percent / aq. CuBr2 / methanol / Heating
View Scheme
2,5-dimethylphenyl trifluoromethanesulfonate
79644-40-9

2,5-dimethylphenyl trifluoromethanesulfonate

4-bromo-m-xylene
553-94-6

4-bromo-m-xylene

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 99 percent / Et3N / PdCl2(dppf) / dioxane / Heating
2: 46 percent / aq. CuBr2 / methanol / Heating
View Scheme
2,3-dibromo-1,4-dimethylbenzene
15540-84-8

2,3-dibromo-1,4-dimethylbenzene

A

para-xylene
106-42-3

para-xylene

B

4-bromo-m-xylene
553-94-6

4-bromo-m-xylene

Conditions
ConditionsYield
With tris(2,2'-bipyridine)ruthenium(II) perchlorate; triethanolamine; Ni((C6H5)CH2O)(C5H2N)(CH2)2(NHCH2CH2CH2)2NH(2+) In acetonitrile at 25℃; for 3h; Photolysis;
With nickel(II) 1,4,8,11-tetraazacyclotetradecane; tris(2,2'-bipyridine)ruthenium(II) perchlorate; triethanolamine In acetonitrile at 25℃; for 3h; Photolysis;
4-bromo-m-xylene
553-94-6

4-bromo-m-xylene

triethyl phosphite
122-52-1

triethyl phosphite

(2,5-dimethylphenyl)diethyl phosphonate
58983-18-9

(2,5-dimethylphenyl)diethyl phosphonate

Conditions
ConditionsYield
With nickel dibromide at 160℃; for 2h; Inert atmosphere;100%
Irradiation;
2-tert-Butylphenol
88-18-6

2-tert-Butylphenol

4-bromo-m-xylene
553-94-6

4-bromo-m-xylene

3-tert-butyl-2',5'-dimethylbiphenyl-2-ol

3-tert-butyl-2',5'-dimethylbiphenyl-2-ol

Conditions
ConditionsYield
With tris(triphenylphosphine)rhodium(I) chloride; caesium carbonate; diisopropyl(2-tert-butyl)phenoxyphosphine In toluene for 18h; Heating;100%
With caesium carbonate; diisopropyl(2-tert-butyl)phenoxyphosphine; RhCl(PPh3)3 In toluene for 18h; Heating;100%
With caesium carbonate; chloro(1,5-cyclooctadiene)rhodium(I) dimer In toluene for 18h; Heating;94 % Spectr.
triisopropyl phosphite
116-17-6

triisopropyl phosphite

4-bromo-m-xylene
553-94-6

4-bromo-m-xylene

(2,5-dimethylphenyl)diisopropyl phosphonate

(2,5-dimethylphenyl)diisopropyl phosphonate

Conditions
ConditionsYield
With nickel dibromide at 150℃; for 3h; Inert atmosphere;100%
4-bromo-m-xylene
553-94-6

4-bromo-m-xylene

2-chloropropionyl chloride
625-36-5

2-chloropropionyl chloride

4-bromo-1-(3'-chloro-1'-oxopropyl)-2,5-dimethylbenzene
246022-83-3

4-bromo-1-(3'-chloro-1'-oxopropyl)-2,5-dimethylbenzene

Conditions
ConditionsYield
Stage #1: 2-chloropropionyl chloride With aluminum (III) chloride In dichloromethane for 0.25h; Schlenk technique; Inert atmosphere;
Stage #2: 4-bromo-m-xylene In dichloromethane at 20℃; for 20h; Inert atmosphere;
99%
With aluminium trichloride In dichloromethane at 50℃; for 3h; Addition;87%
With aluminum (III) chloride In carbon disulfide at 0℃; for 1h; Reflux;61%
With aluminium trichloride In carbon disulfide at 20℃; for 16h;
4-bromo-m-xylene
553-94-6

4-bromo-m-xylene

2-Methylphenylboronic acid
16419-60-6

2-Methylphenylboronic acid

2,5,2'-trimethyl-1,1'-biphenyl
76708-72-0

2,5,2'-trimethyl-1,1'-biphenyl

Conditions
ConditionsYield
With Merrifield resin-bound dicyclohexylphosphinobiphenyl ligand; caesium carbonate; tris(dibenzylideneacetone)dipalladium (0) In tetrahydrofuran at 65℃; Suzuki reaction;99%
4-bromo-m-xylene
553-94-6

4-bromo-m-xylene

1-amino-3-methylbenzene
108-44-1

1-amino-3-methylbenzene

N-(2,5-dimethylphenyl)-m-toluidine

N-(2,5-dimethylphenyl)-m-toluidine

Conditions
ConditionsYield
With Merrifield resin-bound dicyclohexylphosphinobiphenyl ligand; sodium t-butanolate; tris(dibenzylideneacetone)dipalladium (0) In toluene at 100℃;99%
4-bromo-m-xylene
553-94-6

4-bromo-m-xylene

2-phenylaniline
90-41-5

2-phenylaniline

2,5-dimethyl-2'-phenyldiphenylamine

2,5-dimethyl-2'-phenyldiphenylamine

Conditions
ConditionsYield
With palladium diacetate; P(i-BuNCH2CH2)3N; sodium t-butanolate In toluene at 80℃;99%
4-bromo-m-xylene
553-94-6

4-bromo-m-xylene

chloroacetyl chloride
79-04-9

chloroacetyl chloride

2-(2,5-dimethylphenyl)acetyl chloride
55312-97-5

2-(2,5-dimethylphenyl)acetyl chloride

Conditions
ConditionsYield
Stage #1: 4-bromo-m-xylene; chloroacetyl chloride With hydrogenchloride; ruthenium(IV) oxide; palladium 10% on activated carbon In dimethyl sulfoxide at 100℃; for 5h;
Stage #2: With sodium sulfite In water; dimethyl sulfoxide at 135℃; for 8.25h; Temperature;
98.1%
1-methyl-piperazine
109-01-3

1-methyl-piperazine

4-bromo-m-xylene
553-94-6

4-bromo-m-xylene

1-(2,5-dimethylhenyl)-4-methylpiperazine

1-(2,5-dimethylhenyl)-4-methylpiperazine

Conditions
ConditionsYield
With tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate In toluene at 80℃; for 4h;98%
With tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate at 80℃; for 4h; Arylation;98%
With tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate In neat (no solvent) at 80℃; for 4h; Inert atmosphere;98%
With tris(dibenzylideneacetone)dipalladium (0); sodium isopropylate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In toluene at 110℃; for 7h; Substitution;68%
4-bromo-m-xylene
553-94-6

4-bromo-m-xylene

p-toluidine
106-49-0

p-toluidine

N-(4-methylphenyl)-2,5-dimethylaniline
34160-15-1

N-(4-methylphenyl)-2,5-dimethylaniline

Conditions
ConditionsYield
With bis[2-(diphenylphosphino)phenyl] ether; sodium t-butanolate; palladium dichloride In toluene at 80℃; for 17h;98%
With palladium diacetate; bis[2-(diphenylphosphino)phenyl] ether; sodium t-butanolate In toluene at 80℃; for 3h;95%
With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate In toluene at 110℃; for 4h; Inert atmosphere;67%
4-bromo-m-xylene
553-94-6

4-bromo-m-xylene

bis(2,5-dimethylphenyl) sulfide
35019-02-4

bis(2,5-dimethylphenyl) sulfide

Conditions
ConditionsYield
With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; thiourea; [2-((diphenylphospino)methyl)-2-methyl-1,3-propanediyl]bis[diphenylphosphine] In 1,4-dioxane at 100℃; for 18h; Inert atmosphere;98%
lithium trimethoxy(1,2,2-trifluorovinyl)borate

lithium trimethoxy(1,2,2-trifluorovinyl)borate

4-bromo-m-xylene
553-94-6

4-bromo-m-xylene

1,4-dimethyl-2-(1,2,2-trifluorovinyl)benzene
1361925-73-6

1,4-dimethyl-2-(1,2,2-trifluorovinyl)benzene

Conditions
ConditionsYield
With potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0); XPhos In tetrahydrofuran at 20 - 80℃; for 15.25h; Suzuki coupling; Inert atmosphere;98%
2-bromoacetyl chloride
22118-09-8

2-bromoacetyl chloride

4-bromo-m-xylene
553-94-6

4-bromo-m-xylene

2-(2,5-dimethylphenyl)acetyl chloride
55312-97-5

2-(2,5-dimethylphenyl)acetyl chloride

Conditions
ConditionsYield
Stage #1: 2-bromoacetyl chloride; 4-bromo-m-xylene With hydrogenchloride; ruthenium(IV) oxide; palladium 10% on activated carbon In dimethyl sulfoxide at 100℃; for 5h;
Stage #2: With sodium sulfite In water; dimethyl sulfoxide at 135℃; for 8.25h;
97.1%
dimethylmonochlorosilane
1066-35-9

dimethylmonochlorosilane

4-bromo-m-xylene
553-94-6

4-bromo-m-xylene

(2,5-dimethylphenyl)dimethylsilane

(2,5-dimethylphenyl)dimethylsilane

Conditions
ConditionsYield
Stage #1: 4-bromo-m-xylene With n-butyllithium In tetrahydrofuran at -78℃; for 3h; Inert atmosphere;
Stage #2: dimethylmonochlorosilane In tetrahydrofuran at -78 - 20℃;
97%
With tert.-butyl lithium In diethyl ether; pentane 1.) -78 deg C, 2.) -78 deg C to 20 deg C, 2 h; Yield given;
morpholine
110-91-8

morpholine

4-bromo-m-xylene
553-94-6

4-bromo-m-xylene

4-(2,5-dimethylphenyl)morpholine

4-(2,5-dimethylphenyl)morpholine

Conditions
ConditionsYield
With tris(dibenzylideneacetone)dipalladium (0); (-)-2-(dicyclohexylphosphino)-2'-(dimethylamino)-1,1'-binaphthyl; sodium t-butanolate In 1,2-dimethoxyethane Ambient temperature;97%
With potassium hexamethylsilazane In 1,4-dioxane at 100℃; for 0.25h; metal-free Buchwald-Hartwig amination; Inert atmosphere;88 %Chromat.
4-bromo-m-xylene
553-94-6

4-bromo-m-xylene

2-methoxy-phenylamine
90-04-0

2-methoxy-phenylamine

N-(2-methoxyphenyl)-2,5-dimethylaniline

N-(2-methoxyphenyl)-2,5-dimethylaniline

Conditions
ConditionsYield
With tris(dibenzylideneacetone)dipalladium (0); sodium isopropylate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In toluene at 110℃; for 19h; Substitution;97%
With bis[2-(diphenylphosphino)phenyl] ether; sodium t-butanolate; palladium dichloride In toluene at 80℃; for 4h;93%
With palladium diacetate; bis[2-(diphenylphosphino)phenyl] ether; sodium t-butanolate In toluene at 80℃; for 21h;90%
4-bromo-m-xylene
553-94-6

4-bromo-m-xylene

trans-2-phenylvinylboronic acid
6783-05-7

trans-2-phenylvinylboronic acid

(E)-2,5-dimethyl-1-styrylbenzene
19290-86-9, 21162-42-5

(E)-2,5-dimethyl-1-styrylbenzene

Conditions
ConditionsYield
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; palladium diacetate In tetrahydrofuran at 40℃; for 24h; Suzuki-Miyaura coupling;97%
4-bromo-m-xylene
553-94-6

4-bromo-m-xylene

1-Naphthylboronic acid
13922-41-3

1-Naphthylboronic acid

1-(2,5-dimethylphenyl)naphthalene
131117-61-8

1-(2,5-dimethylphenyl)naphthalene

Conditions
ConditionsYield
With potassium phosphate; C29H37O2P; palladium diacetate In toluene at 110℃; for 3h; Suzuki-Miyaura Coupling; Inert atmosphere; Schlenk technique;97%
4-bromo-m-xylene
553-94-6

4-bromo-m-xylene

ortho-cresol
95-48-7

ortho-cresol

1,4-dimethyl-2-(o-tolyloxy)benzene

1,4-dimethyl-2-(o-tolyloxy)benzene

Conditions
ConditionsYield
With palladium diacetate; potassium phosphate; 2-N,N-(dimethylamino)-2'-di-tert-butylphosphino-1,1'-binaphthyl In toluene at 100℃; for 24h;96%
With potassium phosphate; tert-butyl XPhos; palladium diacetate In toluene at 100℃; for 24h;92%
With potassium phosphate; 2-di-tert-butylphosphino-2',4',6'-tricyclohexyl-3,6-dimethoxybiphenyl In 1,2-dimethoxyethane; toluene at 40℃; for 24h; Inert atmosphere;80%
4-bromo-m-xylene
553-94-6

4-bromo-m-xylene

N-methylaniline
100-61-8

N-methylaniline

N-methyl-N-phenyl-2,5-dimethylbenzenamine

N-methyl-N-phenyl-2,5-dimethylbenzenamine

Conditions
ConditionsYield
With tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate at 80℃; for 36h; Arylation;95%
With tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate In toluene at 80℃; for 36h;94%
With tris(dibenzylideneacetone)dipalladium (0); sodium isopropylate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In toluene at 110℃; for 22h; Substitution;85%
4-bromo-m-xylene
553-94-6

4-bromo-m-xylene

4-Chlorophenylboronic acid
1679-18-1

4-Chlorophenylboronic acid

4’-chloro-2,5-dimethyl-1,1’-biphenyl
71149-93-4

4’-chloro-2,5-dimethyl-1,1’-biphenyl

Conditions
ConditionsYield
With potassium phosphate; monophosphine 1,2,3,4,5-pentaphenyl-1'-(di-tert-butylphosphino)ferrocene; bis(dibenzylideneacetone)-palladium(0) In toluene at 100℃; for 14h; Suzuki coupling;95%
With potassium phosphate; monophosphine 1,2,3,4,5-pentaphenyl-1'-(di-tert-butylphosphino)ferrocene; bis(dibenzylideneacetone)-palladium(0) In toluene95%
4-bromo-m-xylene
553-94-6

4-bromo-m-xylene

bicyclo[2.2.1]hepta-2,5-diene
121-46-0

bicyclo[2.2.1]hepta-2,5-diene

C23H24

C23H24

Conditions
ConditionsYield
With palladium diacetate; caesium carbonate; triphenylphosphine In toluene at 20 - 115℃; for 5h; Temperature; Reagent/catalyst; Solvent; Sealed tube; stereoselective reaction;95%
4-bromo-m-xylene
553-94-6

4-bromo-m-xylene

acrylic acid methyl ester
292638-85-8

acrylic acid methyl ester

methyl 3-(2,5-dimethylphenyl)prop-2-enoate

methyl 3-(2,5-dimethylphenyl)prop-2-enoate

Conditions
ConditionsYield
With N-Methyldicyclohexylamine; 2C32H41O4P*Pd(2+)*2Cl(1-) In N,N-dimethyl acetamide at 100℃; for 16h; Heck Reaction; Inert atmosphere;95%
oxirane
75-21-8

oxirane

4-bromo-m-xylene
553-94-6

4-bromo-m-xylene

2-(2,5-dimethylphenyl)ethan-1-ol
6972-51-6

2-(2,5-dimethylphenyl)ethan-1-ol

Conditions
ConditionsYield
Stage #1: 4-bromo-m-xylene With iodine; magnesium In diethyl ether at 60℃; for 1h; Inert atmosphere;
Stage #2: oxirane In diethyl ether at 0℃; for 3h; Temperature; Inert atmosphere;
94.69%
(i) Mg, Et2O, (ii) /BRN= 102378/; Multistep reaction;
4-bromo-m-xylene
553-94-6

4-bromo-m-xylene

phenylboronic acid
98-80-6

phenylboronic acid

2,5-dimethylbiphenyl
7372-85-2

2,5-dimethylbiphenyl

Conditions
ConditionsYield
With palladium diacetate; potassium fluoride; johnphos In tetrahydrofuran at 45℃; for 12h; Suzuki coupling;94%
With potassium phosphate; Pd (sulfur-containing palladacycle); tetra(n-tert-butyl)ammonium bromide In N,N-dimethyl-formamide at 25℃; for 38h; Suzuki cross-coupling;94%
With Pd(4,4'-bis(diphenylphosphino)-2,2',6,6'-tetra-methoxy-3,3'-bipyridine)Cl2; potassium hydroxide In ethanol; dichloromethane at 25℃; for 6h; Suzuki-Miyaura Coupling;94%
4-bromo-m-xylene
553-94-6

4-bromo-m-xylene

phenylacetylene
536-74-3

phenylacetylene

1,4-dimethyl-2-(phenylethynyl)benzene
29778-30-1

1,4-dimethyl-2-(phenylethynyl)benzene

Conditions
ConditionsYield
With potassium phosphate; bis(η3-allyl-μ-chloropalladium(II)); N,N,N′,N′-tetra(diphenylphosphinomethyl)-1,2-ethylenediamine In 1,4-dioxane at 105℃; for 20h; Sonogashira coupling; Inert atmosphere;94%
With dichloro[1-(2,4,6-trimethylbenzyl)-3-(4-adamantylbenzyl)-5,6-dimethylbenzimidazole-2-ylidene]triphenylphosphine palladium(II); potassium tert-butylate In N,N-dimethyl-formamide at 100℃; for 3h; Reagent/catalyst; Sonogashira Cross-Coupling; Schlenk technique;94%
With potassium phosphate; bis(η3-allyl-μ-chloropalladium(II)); tetraphosphine N,N,N′,N′-tetra(diphenylphosphinomethyl)-pyridine-2,6-diamine In N,N-dimethyl acetamide; water at 100℃; for 20h; Sonogashira Cross-Coupling; Schlenk technique; Inert atmosphere;93%
2,6-bis-(toluene-4-sulfonyl)-[1,5,2,6]dithiadiazocane
23516-76-9

2,6-bis-(toluene-4-sulfonyl)-[1,5,2,6]dithiadiazocane

4-bromo-m-xylene
553-94-6

4-bromo-m-xylene

C17H21NO2S2

C17H21NO2S2

Conditions
ConditionsYield
Stage #1: 4-bromo-m-xylene With n-butyllithium In tetrahydrofuran at -78℃; for 1h; Inert atmosphere;
Stage #2: 2,6-bis-(toluene-4-sulfonyl)-[1,5,2,6]dithiadiazocane In tetrahydrofuran for 0.5h; Inert atmosphere;
94%
pyrrolidine
123-75-1

pyrrolidine

4-bromo-m-xylene
553-94-6

4-bromo-m-xylene

N-(2,5-xylyl)pyrrolidine
97053-04-8

N-(2,5-xylyl)pyrrolidine

Conditions
ConditionsYield
With palladium diacetate; caesium carbonate; (S)-(1,1'-binaphthalene)-2,2'-diylbis(diphenylphosphine) In 1,4-dioxane at 100℃; for 17h; Arylation;93%
With pyridine; bis(1,5-cyclooctadiene)nickel (0); 1,10-Phenanthroline; sodium t-butanolate at 100℃; Glovebox; Inert atmosphere;8 %Chromat.
4-bromo-m-xylene
553-94-6

4-bromo-m-xylene

1-amino-2-propene
107-11-9

1-amino-2-propene

N-allyl-2,5-xylidine
13519-81-8

N-allyl-2,5-xylidine

Conditions
ConditionsYield
With tris-(dibenzylideneacetone)dipalladium(0); johnphos; sodium t-butanolate; tris(dibenzylideneacetone)dipalladium (0) In toluene at 80℃; for 6h; Arylation;93%

553-94-6Relevant articles and documents

Molecular tweezers based on trivalent phosphine, preparation method of molecular tweezers, metal-molecular tweezers catalyst, and preparation method and application of metal-molecular tweezers catalyst

-

Paragraph 0038; 0059-0060, (2020/12/14)

The invention relates to the technical field of inorganic-metal organic crossing and relates to the technical field of molecular tweezers, in particular to molecular tweezers based on trivalent phosphine, a preparation method of the molecular tweezers, a metal-molecular tweezer catalyst, a preparation method of the metal-molecular tweezer catalyst and an application of the metal-molecular tweezercatalyst, the molecular tweezer based on trivalent phosphine is named as P-MV-PCN-521-R, and R is any one of benzoic acid, p-nitrobenzoic acid, formic acid, p-methylbenzoic acid and dichloroacetic acid. The molecular tweezers based on the trivalent phosphine have distance adjustability. The trivalent phosphine-based metal-molecular tweezer catalyst provided by the invention has a high crystallinesurface area and a high specific surface area. The trivalent phosphine-based metal-molecular tweezer catalyst has good chemical stability and thermal stability, and is a primary condition for applyingthe trivalent phosphine-based metal-molecular tweezer catalyst to the actual field. The trivalent phosphine-based metal-molecular tweezer catalyst with adjustable distance provided by the invention has good selectivity for bromination of aromatic compounds.

Molecular Vises for Precisely Positioning Ligands near Catalytic Metal Centers in Metal-Organic Frameworks

Yan, Wei,Li, Shenhui,Yang, Tao,Xia, Yucong,Zhang, Xinrui,Wang, Chao,Yan, Zier,Deng, Feng,Zhou, Qianghui,Deng, Hexiang

supporting information, p. 16182 - 16187 (2020/10/26)

We report the construction of a molecular vise by pairing a tritopic phenylphosphorus(III) linker and a monotopic linker in opposite positions within a metal-organic framework. The angle between these linkers at metal sites is fixed upon changing the functionality in the monotopic linker, while the distance between them is precisely tuned. This distance within the molecular vise is accurately measured by 1H-31P solid-state nuclear magnetic resonance spectroscopy. This unveils the impact of the distance on catalytic performance without interference from electrostatic effects or changes in the angle of the ligand, which is unprecedented in classic organometallic complexes.

Regioselective monobromination of aromatics via a halogen bond acceptor-donor interaction of catalytic thioamide and N-bromosuccinimide

Bovonsombat, Pakorn,Teecomegaet, Pattaradra,Kulvaranon, Panisanun,Pandey, Aditi,Chobtumskul, Kittithorn,Tungsirisurp, Sireethorn,Sophanpanichkul, Punyanuch,Losuwanakul, Satreerat,Soimaneewan, Dechathon,Kanjanwongpaisan, Patcharida,Siricharoensang, Pornpawit,Choosakoonkriang, Sirirat

, p. 6564 - 6572 (2017/10/17)

Regioselective monobromination of various aromatics was achieved at room temperature using N-bromosuccinimide and 5 mol% of thioamides in acetonitrile. With thiourea as catalyst, activated aromatics, such as anisole, acetanilide, benzamide and phenol analogues containing electron donating or withdrawing groups, were brominated with high regioselectivity. Room temperature brominations of weakly activated aromatics and deactivated 9-fluorenone were accomplished by 5 mol% thioacetamide, higher substrates concentrations and longer reaction times. A backbonding of the bromine lone pairs with the π*of C[dbnd]S group and a halogen bond between the halogen bond donor bromine and the halogen bond acceptor sulfur of the thioamide are thought to be the principal interactions and cause of N-bromosuccinimide activation.

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