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2142-69-0

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2142-69-0 Usage

Chemical Properties

Clear pale yellow to orange liquid

Uses

Different sources of media describe the Uses of 2142-69-0 differently. You can refer to the following data:
1. 2-bromoacetophenone is employed in the selective derivatization of cytosine moieties for the determination of global DNA methylation by reversed phase high performance liquid chromatography with spectrofluorimetric detection.
2. 2′-Bromoacetophenone (2-Bromoacetophenone) was used in the synthesis of novel series of non-condensed 5,5-bicycles.

General Description

2′-Bromoacetophenone (2-Bromoacetophenone) undergoes enantioselective addition reaction with phenylacetylene catalyzed by chiral camphorsulfonamide. It reacts with aliphatic primary amines in the presence of palladium catalyst to afford 3-methyleneisoindolin-1-ones.

Check Digit Verification of cas no

The CAS Registry Mumber 2142-69-0 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 2,1,4 and 2 respectively; the second part has 2 digits, 6 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 2142-69:
(6*2)+(5*1)+(4*4)+(3*2)+(2*6)+(1*9)=60
60 % 10 = 0
So 2142-69-0 is a valid CAS Registry Number.

2142-69-0 Well-known Company Product Price

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  • Alfa Aesar

  • (A11982)  2'-Bromoacetophenone, 99%   

  • 2142-69-0

  • 10g

  • 661.0CNY

  • Detail
  • Alfa Aesar

  • (A11982)  2'-Bromoacetophenone, 99%   

  • 2142-69-0

  • 50g

  • 2586.0CNY

  • Detail
  • Alfa Aesar

  • (A11982)  2'-Bromoacetophenone, 99%   

  • 2142-69-0

  • 250g

  • 6329.0CNY

  • Detail

2142-69-0SDS

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 2'-Bromoacetophenone

1.2 Other means of identification

Product number -
Other names 2'-BroMoacetophenone

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:2142-69-0 SDS

2142-69-0Synthetic route

(1-(2-bromophenyl)ethoxy)trimethylsilane
1025869-90-2

(1-(2-bromophenyl)ethoxy)trimethylsilane

2-bromophenyl methyl ketone
2142-69-0

2-bromophenyl methyl ketone

Conditions
ConditionsYield
With nitrogen dioxide at 20℃; for 1h;100%
1-bromo-2-ethylbenzene
1973-22-4

1-bromo-2-ethylbenzene

2-bromophenyl methyl ketone
2142-69-0

2-bromophenyl methyl ketone

Conditions
ConditionsYield
With Iron(III) nitrate nonahydrate; 1-hydroxy-pyrrolidine-2,5-dione; oxygen In benzonitrile at 90℃; for 21h;99%
With Iron(III) nitrate nonahydrate; N-hydroxyphthalimide In benzonitrile at 100℃; for 20h;95%
With oxygen; silica gel; 4-aminoperbenzoic acid In dichloromethane at 20℃; for 12h;73%
o-cyanobromobenzene
2042-37-7

o-cyanobromobenzene

methylmagnesium bromide
75-16-1

methylmagnesium bromide

2-bromophenyl methyl ketone
2142-69-0

2-bromophenyl methyl ketone

Conditions
ConditionsYield
With hydrogenchloride In tetrahydrofuran; water; toluene at 20 - 25℃; for 2h; Friedel-Crafts Acylation;96.5%
1-(2-bromophenyl)ethanol
5411-56-3

1-(2-bromophenyl)ethanol

2-bromophenyl methyl ketone
2142-69-0

2-bromophenyl methyl ketone

Conditions
ConditionsYield
With silica gel; pyridinium chlorochromate In dichloromethane at 20℃; for 2h; Inert atmosphere;96%
With silica gel; pyridinium chlorochromate In dichloromethane at 20℃; for 2h; Inert atmosphere;95%
With C53H46ClN3P2Ru; potassium tert-butylate; acetone at 56℃; under 750.075 Torr; for 3h; Oppenauer Oxidation;94%
2-bromo-1-ethynylbenzene
766-46-1

2-bromo-1-ethynylbenzene

2-bromophenyl methyl ketone
2142-69-0

2-bromophenyl methyl ketone

Conditions
ConditionsYield
With water at 80℃; for 2h; Temperature; Green chemistry;86%
With iron(III) chloride; water; silver(I) triflimide In 1,4-dioxane at 80℃; for 60h; regioselective reaction;84%
With water at 80℃; for 15h;84%
methylmagnesium bromide
75-16-1

methylmagnesium bromide

2-bromobenzoic acid chloride
7154-66-7

2-bromobenzoic acid chloride

A

2-bromophenyl methyl ketone
2142-69-0

2-bromophenyl methyl ketone

B

2-Methylacetophenone
577-16-2, 122382-54-1

2-Methylacetophenone

Conditions
ConditionsYield
With iron(III)-acetylacetonate In tetrahydrofuran at -78℃;A 85%
B 7 % Chromat.
ortho-bromobenzenesulfonyl hydrazide
60199-33-9

ortho-bromobenzenesulfonyl hydrazide

acetonitrile
75-05-8

acetonitrile

2-bromophenyl methyl ketone
2142-69-0

2-bromophenyl methyl ketone

Conditions
ConditionsYield
With 1,10-Phenanthroline; water; palladium diacetate at 100℃; under 760.051 Torr; for 6h;82%
acetophenone
98-86-2

acetophenone

2-bromophenyl methyl ketone
2142-69-0

2-bromophenyl methyl ketone

Conditions
ConditionsYield
With trifluoromethanesulfonic acid anhydride; magnesium bromide In diethyl ether at 0℃; for 0.166667h;79%
With N-Bromosuccinimide; silver hexafluoroantimonate; dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; copper diacetate In 1,2-dichloro-ethane at 120℃; for 21h; Inert atmosphere; regioselective reaction;50%
With tetra-n-butylammonium tribromide In methanol; diethyl ether; dichloromethane
With N-Bromosuccinimide; C18H24I2N5Pd(1+) In acetonitrile at 95℃; for 24h; Reagent/catalyst; Sealed tube;22 %Chromat.
With N-Bromosuccinimide; 2Ru(2+)*4F6P(1-)*C47H34N8*Pd(2+)*C2H6OS*2I(1-) In 1,2-dichloro-ethane at 95℃; for 16h; Sealed tube;57 %Chromat.
3-(2-bromophenyl)-3-oxopropionic acid methyl ester
294881-08-6

3-(2-bromophenyl)-3-oxopropionic acid methyl ester

2-bromophenyl methyl ketone
2142-69-0

2-bromophenyl methyl ketone

Conditions
ConditionsYield
With hydrogenchloride In methanol; water at 70℃; for 6h;76%
bromobenzene
108-86-1

bromobenzene

acetyl chloride
75-36-5

acetyl chloride

A

2-bromophenyl methyl ketone
2142-69-0

2-bromophenyl methyl ketone

B

para-bromoacetophenone
99-90-1

para-bromoacetophenone

Conditions
ConditionsYield
With iron(III) sulfate In hexane at 20℃; for 0.75h; Friedel-Crafts acylation; Sonication;A 5.2%
B 74%
With poly(4-vinylpyridine) supported trifluoromethanesulfonic acid at 0 - 20℃; for 6h; Friedel-Crafts Acylation; Overall yield = 20 %;
C10H11BrOS
1429632-21-2

C10H11BrOS

2-bromophenyl methyl ketone
2142-69-0

2-bromophenyl methyl ketone

Conditions
ConditionsYield
With 2,2,6,6-tetramethylpiperidinyl-lithium In tetrahydrofuran; hexane at -78℃; for 3h; Inert atmosphere;74%
trimethylsiloxyethene
6213-94-1

trimethylsiloxyethene

1-Bromo-2-iodobenzene
583-55-1

1-Bromo-2-iodobenzene

2-bromophenyl methyl ketone
2142-69-0

2-bromophenyl methyl ketone

Conditions
ConditionsYield
With palladium diacetate; triethylamine; triphenylphosphine In dimethyl sulfoxide; N,N-dimethyl-formamide at 20 - 100℃; for 2h; Heck Reaction; Microwave irradiation; regioselective reaction;72%
2-bromo-N-methoxy-N-methylbenzamide
899425-05-9

2-bromo-N-methoxy-N-methylbenzamide

methylmagnesium bromide
75-16-1

methylmagnesium bromide

2-bromophenyl methyl ketone
2142-69-0

2-bromophenyl methyl ketone

Conditions
ConditionsYield
In tetrahydrofuran; diethyl ether at 0℃; for 15h; Inert atmosphere;72%
In tetrahydrofuran; diethyl ether at 0 - 20℃;
2-bromostyrene
2039-88-5

2-bromostyrene

A

2-bromophenyl methyl ketone
2142-69-0

2-bromophenyl methyl ketone

B

1-(2-bromophenyl)ethanol
5411-56-3

1-(2-bromophenyl)ethanol

Conditions
ConditionsYield
With tris(dibenzoylmethano)iron(III); phenylsilane In ethanol at 20℃; for 27h; Reagent/catalyst; Wacker Oxidation;A 72%
B 23%
With triethylsilane; (1,2,3,4,8,9,10,11,15,16,17,18,22,23,24,25-Hexadecafluorophthalocyaninato)iron(II); oxygen In ethanol at 20℃; under 760.051 Torr; for 13h; Wacker Oxidation; Sealed tube; Green chemistry; chemoselective reaction;A 65%
B 5%
ethyl 2-cyanoacetate
105-56-6

ethyl 2-cyanoacetate

(2-bromophenyl)boronic acid
244205-40-1

(2-bromophenyl)boronic acid

2-bromophenyl methyl ketone
2142-69-0

2-bromophenyl methyl ketone

Conditions
ConditionsYield
With trifluorormethanesulfonic acid; water; palladium diacetate; 2-(3,5-dimethyl-1H-pyrazol-1-yl)pyridine at 60℃; for 5h; regioselective reaction;66%
2-aminoacetophenone
551-93-9

2-aminoacetophenone

2-bromophenyl methyl ketone
2142-69-0

2-bromophenyl methyl ketone

Conditions
ConditionsYield
Stage #1: 2-aminoacetophenone With hydrogen bromide; sodium nitrite In water at 0℃; for 0.333333h; Inert atmosphere;
Stage #2: With copper(I) bromide In water Inert atmosphere;
60%
With hydrogen bromide; copper(I) bromide
With sulfuric acid; copper(I) bromide Diazotization;
2-(2-bromophenyl)propanol
7073-69-0

2-(2-bromophenyl)propanol

2-bromophenyl methyl ketone
2142-69-0

2-bromophenyl methyl ketone

Conditions
ConditionsYield
With bismuth(lll) trifluoromethanesulfonate; dipotassium peroxodisulfate; silver nitrate In water at 30℃; for 24h; Inert atmosphere; Green chemistry;60%
1-(2-bromophenyl)ethanol
5411-56-3

1-(2-bromophenyl)ethanol

A

2-bromophenyl methyl ketone
2142-69-0

2-bromophenyl methyl ketone

B

(1S)-1-(2-bromophenyl)ethanol
5411-56-3, 76116-20-6, 118375-26-1, 114446-55-8

(1S)-1-(2-bromophenyl)ethanol

C

(1R)-1-(2-bromophenyl)ethan-1-ol
5411-56-3, 114446-55-8, 118375-26-1, 76116-20-6

(1R)-1-(2-bromophenyl)ethan-1-ol

Conditions
ConditionsYield
With sodium hydrogencarbonate; sodium bromide; chiral 4,1'-dinaphthyl-3,2'-cyclo[C(Me)2-N(oxyl)-C(Me)2] In dichloromethane; water at -15℃; for 1.5h; resolution of racemate; Electrolysis; Title compound not separated from byproducts;A 54%
B n/a
C n/a
Stage #1: 1-(2-bromophenyl)ethanol With N,N'-bis(salicylidene)-1,2-cyclohexanediaminomanganese(III) chloride; potassium acetate In dichloromethane; water for 0.0833333h;
Stage #2: With N-Bromosuccinimide In dichloromethane; water at 20℃; for 4h; Kinetics; enantioselective reaction;
A n/a
B n/a
C n/a
2-bromostyrene
2039-88-5

2-bromostyrene

2-bromophenyl methyl ketone
2142-69-0

2-bromophenyl methyl ketone

Conditions
ConditionsYield
With manganese(IV) oxide; palladium dichloride In water; acetonitrile at 60℃; for 25h;53%
With methanol; oxygen; potassium carbonate at 150℃; under 3000.3 Torr; for 12h; regioselective reaction;47.3 %Chromat.
1-(2-bromophenyl)ethanol
5411-56-3

1-(2-bromophenyl)ethanol

A

2-bromophenyl methyl ketone
2142-69-0

2-bromophenyl methyl ketone

B

(1R)-1-(2-bromophenyl)ethan-1-ol
5411-56-3, 114446-55-8, 118375-26-1, 76116-20-6

(1R)-1-(2-bromophenyl)ethan-1-ol

Conditions
ConditionsYield
With C50H42ClN2O3Ru In chloroform at 25℃; Kinetics; Molecular sieve; Resolution of racemate; enantioselective reaction;A n/a
B 48.8%
Stage #1: 1-(2-bromophenyl)ethanol With C28H36ClMnN2O2; potassium acetate In dichloromethane; water for 0.0833333h;
Stage #2: With N-Bromosuccinimide In dichloromethane; water at 20℃; for 4h; Kinetics; enantioselective reaction;
A n/a
B n/a
1-bromo-2-isopropylbenzene
7073-94-1

1-bromo-2-isopropylbenzene

2-bromophenyl methyl ketone
2142-69-0

2-bromophenyl methyl ketone

Conditions
ConditionsYield
With oxygen at 190℃; under 760.051 Torr; for 24h; Autoclave;34%
o-bromo-α-fluoroacetophenone
135774-34-4

o-bromo-α-fluoroacetophenone

A

2-fluoroacetophenone
450-95-3

2-fluoroacetophenone

B

2-bromophenyl methyl ketone
2142-69-0

2-bromophenyl methyl ketone

Conditions
ConditionsYield
With 1,3-dimethyl-2-phenyl-2,3-dihydro-1H-benzo[d]imidazole; azobisisobutyronitrile In acetonitrile at 90℃; for 1.5h; Rate constant; other temp., other concentration, and time;A 8.5%
B 21.7%
α-(benzoyloxy)-o-bromoacetophenone
135774-35-5

α-(benzoyloxy)-o-bromoacetophenone

A

phenacyl benzoate
33868-50-7

phenacyl benzoate

B

2-bromophenyl methyl ketone
2142-69-0

2-bromophenyl methyl ketone

Conditions
ConditionsYield
With tris(2,2'-bipyridine)ruthenium(II) perchlorate; 1,3-dimethyl-2-phenyl-2,3-dihydro-1H-benzo[d]imidazole In acetonitrile at 20℃; for 13h; Rate constant; Irradiation; other reagents, reaction without irradiation, var. time;A 15.7%
B 12.5%
2-bromobenzoic acid chloride
7154-66-7

2-bromobenzoic acid chloride

2-bromophenyl methyl ketone
2142-69-0

2-bromophenyl methyl ketone

methyl magnesium iodide
917-64-6

methyl magnesium iodide

o-cyanobromobenzene
2042-37-7

o-cyanobromobenzene

2-bromophenyl methyl ketone
2142-69-0

2-bromophenyl methyl ketone

Conditions
ConditionsYield
With diethyl ether anschliessendes Behandeln mit wss. HCl;
3-(2-bromophenyl)-3-oxopropionic acid ethyl ester
50671-05-1

3-(2-bromophenyl)-3-oxopropionic acid ethyl ester

2-bromophenyl methyl ketone
2142-69-0

2-bromophenyl methyl ketone

Conditions
ConditionsYield
With sulfuric acid
2-bromobenzoic acid chloride
7154-66-7

2-bromobenzoic acid chloride

2-bromophenyl methyl ketone
2142-69-0

2-bromophenyl methyl ketone

Conditions
ConditionsYield
With diethyl (ethoxymagnesio)malonate
With dimethylcadmium
Multi-step reaction with 3 steps
1: aqueous ammonia
2: thionyl chloride
3: diethyl ether / anschliessendes Behandeln mit wss. HCl
View Scheme
Multi-step reaction with 2 steps
1: triethylamine / dichloromethane / 1 h / 0 - 20 °C
2: tetrahydrofuran; diethyl ether / 0 - 20 °C
View Scheme
3-methyl-4-(o-bromophenyl)-1,2-dioxetane
143798-76-9

3-methyl-4-(o-bromophenyl)-1,2-dioxetane

A

formaldehyd
50-00-0

formaldehyd

B

2-bromophenyl methyl ketone
2142-69-0

2-bromophenyl methyl ketone

Conditions
ConditionsYield
With 9,10-Dibromoanthracene; 9,10-diphenylanthracene In tetrachloromethane at 60℃; Rate constant; Thermodynamic data; Ea; ΔH(excit.); ΔS(excit.); ΔG(excit.);
acetophenone
98-86-2

acetophenone

A

2-bromophenyl methyl ketone
2142-69-0

2-bromophenyl methyl ketone

B

1-(3-Bromophenyl)ethanone
2142-63-4

1-(3-Bromophenyl)ethanone

Conditions
ConditionsYield
With potassium bromate; sulfuric acid In water Ambient temperature; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
2-bromophenyl methyl ketone
2142-69-0

2-bromophenyl methyl ketone

1-(2-bromophenyl)ethanol
5411-56-3

1-(2-bromophenyl)ethanol

Conditions
ConditionsYield
With [{(CH3)2C3HN2-C5H3N-C3H3N2}RuCl2(PPh3)]; potassium isopropoxide; isopropyl alcohol at 82℃; for 0.00277778h; Inert atmosphere;100%
Stage #1: 2-bromophenyl methyl ketone With C107H90Cl2N10P4Ru2(2+)*2Cl(1-) In isopropyl alcohol at 82℃; for 0.166667h; Inert atmosphere;
Stage #2: With potassium isopropoxide In isopropyl alcohol for 2h; Catalytic behavior; Inert atmosphere;
100%
Stage #1: 2-bromophenyl methyl ketone With sodium tetrahydroborate In methanol at 20℃; for 24h;
Stage #2: With water In methanol
100%
2-bromophenyl methyl ketone
2142-69-0

2-bromophenyl methyl ketone

phenylhydrazine
100-63-0

phenylhydrazine

N-[1-(2-Bromo-phenyl)-eth-(Z)-ylidene]-N'-phenyl-hydrazine
1011736-72-3

N-[1-(2-Bromo-phenyl)-eth-(Z)-ylidene]-N'-phenyl-hydrazine

Conditions
ConditionsYield
In 1-methyl-pyrrolidin-2-one at 160℃; for 0.166667h; microwave irradiation;100%
In diethyl ether Heating;
With acetic acid In ethanol for 0.166667h; Heating; Yield given;
2-bromophenyl methyl ketone
2142-69-0

2-bromophenyl methyl ketone

2-Methylphenylboronic acid
16419-60-6

2-Methylphenylboronic acid

1-(2′-methyl-[1,1′-biphenyl]-2-yl)ethanone
217468-51-4

1-(2′-methyl-[1,1′-biphenyl]-2-yl)ethanone

Conditions
ConditionsYield
With potassium phosphate; CyJohnPhos; polymer-incarcerated palladium In water; toluene for 2h; Suzuki-Miyaura coupling; Heating;100%
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In 1,2-dimethoxyethane; ethanol Product distribution; Heating; Suzuki coupling of bromo-acylbenzenes resp. bromo-indole carbaldehydes with boronic acids;98%
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In 1,2-dimethoxyethane; ethanol rt, 15 min; reflux, 48 h;98%
2-bromophenyl methyl ketone
2142-69-0

2-bromophenyl methyl ketone

4-(2-bromophenyl)-1,2,3-thiadiazole

4-(2-bromophenyl)-1,2,3-thiadiazole

Conditions
ConditionsYield
Stage #1: 2-bromophenyl methyl ketone With polystyrene-sulfonylhydrazide resin; acetic acid In tetrahydrofuran at 50℃; for 4h; Solid phase reaction;
Stage #2: With thionyl chloride In 1,2-dichloro-ethane at 60℃; for 5h; Solid phase reaction; Hurd-Mori cyclization;
100%
Multi-step reaction with 2 steps
1: sulfuric acid / ethanol / 2 h / Reflux
2: thionyl chloride / 2 h / 5 - 60 °C
View Scheme
Multi-step reaction with 2 steps
1: sulfuric acid / ethanol / 20 °C / Reflux
2: thionyl chloride / 2 h / Reflux
View Scheme
Multi-step reaction with 2 steps
1: ethanol / 3 h / 80 °C
2: thionyl chloride / 2 h / 80 °C
View Scheme
2-bromophenyl methyl ketone
2142-69-0

2-bromophenyl methyl ketone

dimethyl zinc(II)
544-97-8

dimethyl zinc(II)

2-Methylacetophenone
577-16-2, 122382-54-1

2-Methylacetophenone

Conditions
ConditionsYield
(1,2-bis(diphenylphosphino)ethane)palladium(II) chloride In 1,4-dioxane for 1.5h; Heating;100%
2-bromophenyl methyl ketone
2142-69-0

2-bromophenyl methyl ketone

sodium thiomethoxide
5188-07-8

sodium thiomethoxide

2'-(methylthio)acetophenone
1441-97-0

2'-(methylthio)acetophenone

Conditions
ConditionsYield
In tetrahydrofuran at 75℃; for 10h;100%
In tetrahydrofuran at 75℃; for 12h;88%
In tetrahydrofuran
2-bromophenyl methyl ketone
2142-69-0

2-bromophenyl methyl ketone

2-(2-bromophenyl)-2-oxoacetic acid
26767-16-8

2-(2-bromophenyl)-2-oxoacetic acid

Conditions
ConditionsYield
With pyridine; selenium(IV) oxide at 100℃; for 2h;100%
With hydrogenchloride; sodium dichromate In water at 95℃; for 6h;90%
With pyridine; selenium(IV) oxide at 120℃; for 18h; Inert atmosphere;87%
2-bromophenyl methyl ketone
2142-69-0

2-bromophenyl methyl ketone

(E)-1-(2-bromophenyl)ethan-1-one oxime

(E)-1-(2-bromophenyl)ethan-1-one oxime

Conditions
ConditionsYield
With hydroxylamine hydrochloride; sodium acetate In methanol Heating;100%
With hydroxylamine hydrochloride; sodium hydroxide In ethanol; water at 20℃; for 24h; pH=9; Cooling with ice;92%
With hydroxylamine hydrochloride; sodium carbonate In ethanol; water pH=5; Reflux;89%
2-bromophenyl methyl ketone
2142-69-0

2-bromophenyl methyl ketone

1-bromo-2-(1,1-difluoroethyl)benzene
444581-46-8

1-bromo-2-(1,1-difluoroethyl)benzene

Conditions
ConditionsYield
With 4-tert-butyl-2,6-dimethylphenylsulfur trifluoride; pyridine hydrofluoride In dichloromethane at 23℃; for 18h;100%
With (bis-(2-methoxyethyl)amino)sulfur trufluoride; methanol at 70℃; for 18h;63%
With morpholinosulfur trifluoride In dichloromethane; water at 20℃; for 672h;12%
2-bromophenyl methyl ketone
2142-69-0

2-bromophenyl methyl ketone

1-(tert-butoxycarbonyl)-4-((tert-butoxycarbonyl)amino)piperidine-4-carboxylic acid
189321-65-1

1-(tert-butoxycarbonyl)-4-((tert-butoxycarbonyl)amino)piperidine-4-carboxylic acid

4-tert-butoxycarbonylamino-4-(5-phenyl-1H-imidazol-2-yl)-piperidine-1-carboxylic acid tert-butyl ester
1035389-11-7

4-tert-butoxycarbonylamino-4-(5-phenyl-1H-imidazol-2-yl)-piperidine-1-carboxylic acid tert-butyl ester

Conditions
ConditionsYield
Stage #1: 1-(tert-butoxycarbonyl)-4-((tert-butoxycarbonyl)amino)piperidine-4-carboxylic acid With caesium carbonate In methanol for 2h;
Stage #2: 2-bromophenyl methyl ketone In N,N-dimethyl-formamide for 2h;
Stage #3: With ammonium acetate In xylenes at 20 - 135℃; for 52h;
100%
2-bromophenyl methyl ketone
2142-69-0

2-bromophenyl methyl ketone

B-allyl-1,3,2-dioxaborinane
54655-41-3

B-allyl-1,3,2-dioxaborinane

(S)-(−)-2-(2-bromophenyl)-pent-4-en-2-ol
1201827-38-4

(S)-(−)-2-(2-bromophenyl)-pent-4-en-2-ol

Conditions
ConditionsYield
Stage #1: B-allyl-1,3,2-dioxaborinane With (S)-3,3'-dibromo-1,1'-bi-2-naphthol In toluene at 135℃; for 1h; Inert atmosphere;
Stage #2: 2-bromophenyl methyl ketone In toluene at 35℃; for 120h; Inert atmosphere;
100%
With (S)-3,3'-dibromo-1,1'-bi-2-naphthol; tert-butyl alcohol In toluene at 20℃; for 24h; Inert atmosphere; enantioselective reaction;95%
2-bromophenyl methyl ketone
2142-69-0

2-bromophenyl methyl ketone

(1R)-1-(2-bromophenyl)ethan-1-ol
5411-56-3, 114446-55-8, 118375-26-1, 76116-20-6

(1R)-1-(2-bromophenyl)ethan-1-ol

Conditions
ConditionsYield
With lithium hydroxide; (S)-quinolin-4-yl((1S,2S,4S,5R)-5-vinylquinuclidin-2-yl)methanamine; hydrogen; triphenylphosphine; iridium In methanol at 30℃; under 45004.5 Torr; for 3h; optical yield given as %ee; enantioselective reaction;99%
With dimethylsulfide borane complex; 3-hydroxy-N-[(1R,2S)-cis-2-hydroxy-2,3-dihydro-1H-inden-1-yl]naphthalene-2-carboxamide In tetrahydrofuran at 65℃; Inert atmosphere; enantioselective reaction;99%
With formic acid; triethylamine In water at 50℃; for 6h; enantioselective reaction;98%
2-bromophenyl methyl ketone
2142-69-0

2-bromophenyl methyl ketone

Conditions
ConditionsYield
With hydrogen; potassium hydroxide; 9-amino-9-deoxyepicinchonine In isopropyl alcohol at 40℃; under 45004.5 Torr; for 5h; Autoclave; optical yield given as %ee; enantioselective reaction;99%
With dimethylsulfide borane complex; 3-hydroxy-N-[(2S)-1-hydroxy-1,1,3-triphenylpropan-2-yl]naphthalene-2-carboxamide In tetrahydrofuran at 65℃; Inert atmosphere; enantioselective reaction;99%
With D-glucose In aq. phosphate buffer at 25℃; for 24h; pH=7.0; stereoselective reaction;99%
phthalimide
136918-14-4

phthalimide

2-bromophenyl methyl ketone
2142-69-0

2-bromophenyl methyl ketone

2-(2-acetylphenyl)-1H-isoindole-1,3(2H)-dione
83665-31-0

2-(2-acetylphenyl)-1H-isoindole-1,3(2H)-dione

Conditions
ConditionsYield
With copper(I) oxide at 100℃; for 48h;99%
2-bromophenyl methyl ketone
2142-69-0

2-bromophenyl methyl ketone

phenylboronic acid
98-80-6

phenylboronic acid

1-([1,1'-biphenyl]-2-yl)ethanone
2142-66-7

1-([1,1'-biphenyl]-2-yl)ethanone

Conditions
ConditionsYield
With palladium diacetate; N,N-diisopropyl-1,1-diphenylphosphanamine; potassium carbonate In tetrahydrofuran for 48h; Suzuki-Miyamura cross-coupling reaction; Heating;99%
With potassium phosphate monohydrate; 1‐ethyl‐2‐(1‐ethylindol-2-yl)benzoimidazole; palladium diacetate In 1,4-dioxane at 60℃; for 24h; Suzuki-Miyaura Coupling; Inert atmosphere; Schlenk technique;99%
With Ph2P(CH2CH2O)22CH3; triethylamine; palladium dichloride In water at 100℃; for 1h; Suzuki coupling; Inert atmosphere;98%
2-bromophenyl methyl ketone
2142-69-0

2-bromophenyl methyl ketone

4-methoxyphenylboronic acid
5720-07-0

4-methoxyphenylboronic acid

2'-p-methoxyphenylacetophenone

2'-p-methoxyphenylacetophenone

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; toluene for 18h; Suzuki coupling; Inert atmosphere; Reflux;99%
With triethylamine In methanol for 8h; Suzuki Coupling;91%
With C42H48Cl4N4Pd2S2; potassium carbonate In water at 60℃; for 24h; Time; Suzuki-Miyaura Coupling; Inert atmosphere;88%
2-bromophenyl methyl ketone
2142-69-0

2-bromophenyl methyl ketone

1,3,5-tris(2’-bromophenyl)benzene
380626-56-2

1,3,5-tris(2’-bromophenyl)benzene

Conditions
ConditionsYield
With tetrachlorosilane In ethanol at 20℃;99%
With tetrachlorosilane In ethanol at 0 - 20℃; for 16h; Inert atmosphere;97%
With tetrachlorosilane In ethanol at 0 - 20℃; for 25.5h; Inert atmosphere;90%
2-bromophenyl methyl ketone
2142-69-0

2-bromophenyl methyl ketone

ethyltriphenylphosphonium bromide
1530-32-1

ethyltriphenylphosphonium bromide

(E)-1-bromo-2-(but-2-en-2-yl)benzene
96308-15-5

(E)-1-bromo-2-(but-2-en-2-yl)benzene

Conditions
ConditionsYield
Stage #1: ethyltriphenylphosphonium bromide With potassium tert-butylate In toluene at 0 - 23℃;
Stage #2: 2-bromophenyl methyl ketone In toluene for 8h; Heating;
99%
trimethylsilyl cyanide
7677-24-9

trimethylsilyl cyanide

2-bromophenyl methyl ketone
2142-69-0

2-bromophenyl methyl ketone

2-(trimethylsilyloxy)-2-(2'-bromophenyl)propanenitrile

2-(trimethylsilyloxy)-2-(2'-bromophenyl)propanenitrile

Conditions
ConditionsYield
With KNdF4 for 0.0666667h; Irradiation;99%
With C29H38AlN4O2(1+)*CF3O3S(1-) In neat (no solvent) at 20℃; for 0.5h; Catalytic behavior; Inert atmosphere; Schlenk technique;97%
Fe(Cp)2PF6 at 20℃; for 0.166667h;93%
With R-(+)-α-methylbenzylamine-(2R,3R)-(-)-2,3-dihydroxybutanedioic acid In dichloromethane at 10 - 20℃; for 84h; optical yield given as %ee;
2-bromophenyl methyl ketone
2142-69-0

2-bromophenyl methyl ketone

2-formylbenzene boronic acid
40138-16-7

2-formylbenzene boronic acid

2’acetyl-[1,1'-biphenyl]-2-carbaldehyde
100914-80-5

2’acetyl-[1,1'-biphenyl]-2-carbaldehyde

Conditions
ConditionsYield
With potassium fluoride; palladium diacetate; 2-[bis(1,1-dimethylethyl)phosphino]-1-phenyl-1H-indole In tetrahydrofuran at 20℃; for 2h; Suzuki-Miyaura coupling; Inert atmosphere;99%
With tris-(dibenzylideneacetone)dipalladium(0); potassium fluoride dihydrate; tri tert-butylphosphoniumtetrafluoroborate In tetrahydrofuran at 40℃; for 12h; Suzuki-Miyaura Coupling; Inert atmosphere;99%
With tris-(dibenzylideneacetone)dipalladium(0); potassium fluoride dihydrate; tri tert-butylphosphoniumtetrafluoroborate In tetrahydrofuran Suzuki-Miyaura coupling; Inert atmosphere;95%
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,3-dioxane at 80℃; for 14h; Inert atmosphere;71%
2-bromophenyl methyl ketone
2142-69-0

2-bromophenyl methyl ketone

2-formyl-4,5-(methylenedioxy)benzeneboronic acid
94838-88-7

2-formyl-4,5-(methylenedioxy)benzeneboronic acid

6-(2-acetylphenyl)benzo[d][1,3]dioxole-5-carbaldehyde
1149344-88-6

6-(2-acetylphenyl)benzo[d][1,3]dioxole-5-carbaldehyde

Conditions
ConditionsYield
With potassium fluoride; palladium diacetate; 2-[bis(1,1-dimethylethyl)phosphino]-1-phenyl-1H-indole In tetrahydrofuran at 20℃; for 2h; Suzuki-Miyaura coupling; Inert atmosphere;99%
2,6-bis(hydrazino)pyridine
23743-82-0

2,6-bis(hydrazino)pyridine

2-bromophenyl methyl ketone
2142-69-0

2-bromophenyl methyl ketone

C21H19Br2N5
1337906-88-3

C21H19Br2N5

Conditions
ConditionsYield
With toluene-4-sulfonic acid In benzene Reflux; Inert atmosphere;99%
fur-2-ylboronic acid
13331-23-2

fur-2-ylboronic acid

2-bromophenyl methyl ketone
2142-69-0

2-bromophenyl methyl ketone

1-(2-(furan-2-yl)phenyl)ethan-1-one
19275-14-0

1-(2-(furan-2-yl)phenyl)ethan-1-one

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; toluene for 18h; Inert atmosphere; Reflux;99%
pent-1-yn-5-ol
5390-04-5

pent-1-yn-5-ol

2-bromophenyl methyl ketone
2142-69-0

2-bromophenyl methyl ketone

1-(2-(5-hydroxypent-1-yn-1-yl)phenyl)ethan-1-one

1-(2-(5-hydroxypent-1-yn-1-yl)phenyl)ethan-1-one

Conditions
ConditionsYield
Stage #1: 2-bromophenyl methyl ketone With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; triphenylphosphine at 20℃; for 0.5h; Sealed tube; Inert atmosphere;
Stage #2: pent-1-yn-5-ol at 85℃; for 48h; Sealed tube; Inert atmosphere;
99%
2-bromophenyl methyl ketone
2142-69-0

2-bromophenyl methyl ketone

benzaldehyde
100-52-7

benzaldehyde

1-(2-bromophenyl)-3-phenylprop-2-en-1-one
108237-92-9

1-(2-bromophenyl)-3-phenylprop-2-en-1-one

Conditions
ConditionsYield
With potassium hydroxide In ethanol; water at 25℃; Claisen-Schmidt Condensation;98.3%
With sodium hydroxide In ethanol at 20℃; for 3h;91%
2-bromophenyl methyl ketone
2142-69-0

2-bromophenyl methyl ketone

ethylene glycol
107-21-1

ethylene glycol

2-(2-bromophenyl)-2-methyl-1,3-dioxolane
50777-64-5

2-(2-bromophenyl)-2-methyl-1,3-dioxolane

Conditions
ConditionsYield
With toluene-4-sulfonic acid In toluene Dean-Stark; Reflux; Inert atmosphere;98%
With toluene-4-sulfonic acid In toluene for 18h; Dean-Stark; Reflux;94%
With toluene-4-sulfonic acid In benzene for 2h; Heating;93%
2-bromophenyl methyl ketone
2142-69-0

2-bromophenyl methyl ketone

2-Allyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
72824-04-5

2-Allyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

2-(2-bromophenyl)-pent-4-en-2-ol
116384-68-0, 1221721-25-0

2-(2-bromophenyl)-pent-4-en-2-ol

Conditions
ConditionsYield
With indium In water at 30℃; for 24h; Inert atmosphere;98%
With indium iodide In tetrahydrofuran at 40℃; for 24h;97%
furfural
98-01-1

furfural

2-bromophenyl methyl ketone
2142-69-0

2-bromophenyl methyl ketone

(E)-1-(2-bromophenyl)-3-(furan-2-yl)prop-2-en-1-one

(E)-1-(2-bromophenyl)-3-(furan-2-yl)prop-2-en-1-one

Conditions
ConditionsYield
With sodium hydroxide In methanol at 20℃; Inert atmosphere;98%
With ethanol; sodium hydroxide at 20℃; for 3h; Claisen Schmidt condensation;70%

2142-69-0Relevant articles and documents

Intramolecular One-Carbon Homologation of Unstrained Ketones via C-C Activation-Enabled 1,1-Insertion of Alkenes

Huang, Jiangkun,Zhang, Rui,Wu, Xiuli,Dong, Guangbin,Xia, Ying

supporting information, p. 2436 - 2440 (2022/04/07)

Here, we describe the development of a Rh-catalyzed intramolecular one-carbon homologation of unstrained aryl ketones through a formal 1,1-insertion process of olefins, enabled by temporary directing group (TDG)-aided C-C activation. The reaction provides a distinct approach to access various substituted 1-indanones. Computational mechanistic studies reveal that the formal 1,1-insertion is realized by a selective C(sp2)-C(sp3) activation and turnover limiting 2,1-insertion into the alkene, followed by a facile β-H elimination and reinsertion process.

Stepwise benzylic oxygenation via uranyl-photocatalysis

Hu, Deqing,Jiang, Xuefeng

supporting information, p. 124 - 129 (2022/01/19)

Stepwise oxygenation at the benzylic position (1°, 2°, 3°) of aromatic molecules was comprehensively established under ambient conditions via uranyl photocatalysis to produce carboxylic acids, ketones, and alcohols, respectively. The accuracy of the stepwise oxygenation was ensured by the tunability of catalytic activity in uranyl photocatalysis, which was adjusted by solvents and additives demonstrated through Stern–Volmer analysis. Hydrogen atom transfer between the benzylic position and the uranyl catalyst facilitated oxygenation, further confirmed by kinetic studies. Considerably improved efficiency of flow operation demonstrated the potential for industrial synthetic application.

Trinuclear ruthenium carbonyl complexes with salicylaldimine ligands as efficient catalysts for the oxidation of secondary alcohols

Han, Zhangang,Hao, Zhiqiang,Li, Ying,Lin, Jin,Lu, Guo-Liang,Ma, Zhihong

, (2020/12/21)

A series of novel trinuclear ruthenium carbonyl complexes [μ-?2-2-OC6H4-CH=N-Ar)]2Ru3(CO)8 [Ar = Ph (8), C6H4-4-Me (9), C6H4-4-CF3 (10), C6H4-4-Cl (11), C6H3-2,6-Me2 (12), C6H3-2,6-Et2 (13)] and [μ-?2-2-OC6H4-CH=N-C6H3-2,6-iPr2]Ru3(CO)9 (14) were designed and synthesized. All the seven novel complexes were fully characterized by elemental analysis, IR and NMR spectroscopy. Molecular structures of 8, 11, 13 and 14 were further confirmed by single-crystal X-ray diffraction. The catalytic performance of these complexes in the oxidation of secondary alcohols was explored and it was found the combination of such complexes and N-methylmorpholine-N-oxide (NMO) exhibits high catalytic activities for the oxidation of secondary alcohols, giving the corresponding carbonyl compounds in excellent yields.

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