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1889-71-0

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1889-71-0 Usage

Synthesis Reference(s)

Journal of the American Chemical Society, 89, p. 7009, 1967 DOI: 10.1021/ja01002a033The Journal of Organic Chemistry, 48, p. 4407, 1983 DOI: 10.1021/jo00171a056

Check Digit Verification of cas no

The CAS Registry Mumber 1889-71-0 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 1,8,8 and 9 respectively; the second part has 2 digits, 7 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 1889-71:
(6*1)+(5*8)+(4*8)+(3*9)+(2*7)+(1*1)=120
120 % 10 = 0
So 1889-71-0 is a valid CAS Registry Number.
InChI:InChI=1/C14H11ClO/c15-13-8-6-12(7-9-13)14(16)10-11-4-2-1-3-5-11/h1-9H,10H2

1889-71-0 Well-known Company Product Price

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  • Alfa Aesar

  • (A15959)  Benzyl 4-chlorophenyl ketone, 98%   

  • 1889-71-0

  • 5g

  • 483.0CNY

  • Detail
  • Alfa Aesar

  • (A15959)  Benzyl 4-chlorophenyl ketone, 98%   

  • 1889-71-0

  • 25g

  • 1728.0CNY

  • Detail
  • Alfa Aesar

  • (A15959)  Benzyl 4-chlorophenyl ketone, 98%   

  • 1889-71-0

  • 100g

  • 5874.0CNY

  • Detail

1889-71-0SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name 1-(4-chlorophenyl)-2-phenylethanone

1.2 Other means of identification

Product number -
Other names 4'-Chloro-2-phenylacetophenone

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:1889-71-0 SDS

1889-71-0Synthetic route

α-benzyl-4,4'-dichlorobenzoin

α-benzyl-4,4'-dichlorobenzoin

A

4,4'-dichlorobenzoin
4254-20-0

4,4'-dichlorobenzoin

B

4'-chloro-2-phenylacetophenone
1889-71-0

4'-chloro-2-phenylacetophenone

Conditions
ConditionsYield
With tetra-n-butylammonium cyanide In tetrahydrofuran for 1.5h; Ambient temperature;A 12%
B 100%
N-[1-(4-Chloro-phenyl)-1-cyano-2-phenyl-ethyl]-N-phenyl-benzamide
72867-63-1

N-[1-(4-Chloro-phenyl)-1-cyano-2-phenyl-ethyl]-N-phenyl-benzamide

4'-chloro-2-phenylacetophenone
1889-71-0

4'-chloro-2-phenylacetophenone

Conditions
ConditionsYield
With potassium hydroxide In ethanol; water Heating;99%
S-phenyl 4-chlorobenzothioate
28122-82-9

S-phenyl 4-chlorobenzothioate

benzyl(bromo)zinc
62673-31-8

benzyl(bromo)zinc

4'-chloro-2-phenylacetophenone
1889-71-0

4'-chloro-2-phenylacetophenone

Conditions
ConditionsYield
With (phenyl)(bis-triphenylphosphine)palladium(II) chloride In tetrahydrofuran; toluene at 20℃; for 1h; Fukuyama Coupling; Inert atmosphere;98%
4-chlorobenzenesulfinic acid
100-03-8

4-chlorobenzenesulfinic acid

phenylacetonitrile
140-29-4

phenylacetonitrile

4'-chloro-2-phenylacetophenone
1889-71-0

4'-chloro-2-phenylacetophenone

Conditions
ConditionsYield
With [2,2]bipyridinyl; sulfuric acid; water; palladium diacetate In 2-methyl-propan-1-ol at 100℃; for 6h; Inert atmosphere;95%
2-(4-chlorophenyl)-2-oxo-1-phenylethyl benzoate
114679-00-4

2-(4-chlorophenyl)-2-oxo-1-phenylethyl benzoate

4'-chloro-2-phenylacetophenone
1889-71-0

4'-chloro-2-phenylacetophenone

Conditions
ConditionsYield
With palladium(II) trifluoroacetate; hydrogen; [(4S)-4-[5-bis(3,5-di-tert-butyl-4-methoxyphenyl)phosphanyl-1,3-benzodioxol-4-yl]-4,5,6,7-tetrahydro-1,3-benzodioxol-5-yl]-bis(3,5-di-tert-butyl-4-methoxyphenyl)phosphane In acetone at 60℃; under 45004.5 Torr; for 24h; Glovebox; Autoclave; chemoselective reaction;94%
2-(4-chlorophenyl)-2-oxo-1-phenylethyl acetate
119267-71-9

2-(4-chlorophenyl)-2-oxo-1-phenylethyl acetate

4'-chloro-2-phenylacetophenone
1889-71-0

4'-chloro-2-phenylacetophenone

Conditions
ConditionsYield
With tris(bipyridine)ruthenium(II) dichloride hexahydrate; diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate; triethylamine In acetonitrile at 20℃; for 1h; Inert atmosphere; UV-irradiation;92%
benzyl bromide
100-39-0

benzyl bromide

4-chloro-benzoyl chloride
122-01-0

4-chloro-benzoyl chloride

4'-chloro-2-phenylacetophenone
1889-71-0

4'-chloro-2-phenylacetophenone

Conditions
ConditionsYield
With bis-triphenylphosphine-palladium(II) chloride; zinc In 1,2-dimethoxyethane for 0.333333h; Ambient temperature;90%
With bis-triphenylphosphine-palladium(II) chloride; zinc In 1,2-dimethoxyethane at 20℃; for 0.5h; Inert atmosphere; Schlenk technique;
C7H7ClZn*Cl3LiMg

C7H7ClZn*Cl3LiMg

4-chloro-benzoyl chloride
122-01-0

4-chloro-benzoyl chloride

4'-chloro-2-phenylacetophenone
1889-71-0

4'-chloro-2-phenylacetophenone

Conditions
ConditionsYield
With iron(II) chloride In tetrahydrofuran at 25℃; for 0.5h; Reagent/catalyst; Solvent; Inert atmosphere; Schlenk technique;90%
3-(4-chlorophenyl)-3-oxo-2-phenylpropanal

3-(4-chlorophenyl)-3-oxo-2-phenylpropanal

4'-chloro-2-phenylacetophenone
1889-71-0

4'-chloro-2-phenylacetophenone

Conditions
ConditionsYield
With ethylenediamine In tetrahydrofuran for 4h; Heating;88%
chlorobenzene
108-90-7

chlorobenzene

phenylacetyl chloride
103-80-0

phenylacetyl chloride

4'-chloro-2-phenylacetophenone
1889-71-0

4'-chloro-2-phenylacetophenone

Conditions
ConditionsYield
With zinc(II) oxide at 20℃; for 0.0833333h; Friedel-Crafts acylation;85%
With aluminum (III) chloride In dichloromethane at 0 - 20℃;79%
With aluminium trichloride at 20℃;74%
4-chloro-benzoyl chloride
122-01-0

4-chloro-benzoyl chloride

benzyltetrabutyl stiborane
131973-46-1

benzyltetrabutyl stiborane

4'-chloro-2-phenylacetophenone
1889-71-0

4'-chloro-2-phenylacetophenone

Conditions
ConditionsYield
In tetrahydrofuran for 1h; Ambient temperature;85%
phenyl 1H-imidazole-1-sulfonate
1198183-95-7

phenyl 1H-imidazole-1-sulfonate

para-chloroacetophenone
99-91-2

para-chloroacetophenone

4'-chloro-2-phenylacetophenone
1889-71-0

4'-chloro-2-phenylacetophenone

Conditions
ConditionsYield
With palladium diacetate; caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In 1,4-dioxane at 110℃; for 24h; Inert atmosphere; chemoselective reaction;84%
4-vinylbenzyl chloride
1073-67-2

4-vinylbenzyl chloride

phenylhydrazine
100-63-0

phenylhydrazine

4'-chloro-2-phenylacetophenone
1889-71-0

4'-chloro-2-phenylacetophenone

Conditions
ConditionsYield
With 1,4-diaza-bicyclo[2.2.2]octane; 3,7-bis(dimethylamine)phenothiazonium In acetonitrile at 25℃; Irradiation; Green chemistry;83%
2-(4-Chloro-phenyl)-1,3-diphenyl-propan-2-ol

2-(4-Chloro-phenyl)-1,3-diphenyl-propan-2-ol

4'-chloro-2-phenylacetophenone
1889-71-0

4'-chloro-2-phenylacetophenone

Conditions
ConditionsYield
With ammonium cerium(IV) nitrate In water; acetonitrile at 50 - 55℃; for 0.166667h;81%
4-Chlorophenylboronic acid
1679-18-1

4-Chlorophenylboronic acid

phenylacetonitrile
140-29-4

phenylacetonitrile

4'-chloro-2-phenylacetophenone
1889-71-0

4'-chloro-2-phenylacetophenone

Conditions
ConditionsYield
With [2,2]bipyridinyl; potassium fluoride; acetic acid; palladium diacetate In tetrahydrofuran at 80℃; for 48h;80%
phenylacetic acid
103-82-2

phenylacetic acid

Methyl 4-chlorobenzoate
1126-46-1

Methyl 4-chlorobenzoate

4'-chloro-2-phenylacetophenone
1889-71-0

4'-chloro-2-phenylacetophenone

Conditions
ConditionsYield
With lithium hexamethyldisilazane In tetrahydrofuran; N,N-dimethyl-formamide at -4℃; Claisen Condensation; Inert atmosphere;80%
With sodium hexamethyldisilazane In N,N-dimethyl-formamide at -10℃; for 3.5h;
1-chloro-4-(2-phenylethynyl)benzene
5172-02-1

1-chloro-4-(2-phenylethynyl)benzene

4'-chloro-2-phenylacetophenone
1889-71-0

4'-chloro-2-phenylacetophenone

Conditions
ConditionsYield
With methanol In water at -5℃; for 0.5h; Irradiation; Green chemistry;77%
1-(2-(4-chlorophenyl)-2-oxoethyl)tetrahydro-1H-thiophen-1-ium tetraphenylborate
1619239-35-8

1-(2-(4-chlorophenyl)-2-oxoethyl)tetrahydro-1H-thiophen-1-ium tetraphenylborate

4'-chloro-2-phenylacetophenone
1889-71-0

4'-chloro-2-phenylacetophenone

Conditions
ConditionsYield
In toluene at 120℃; Inert atmosphere;76%
1-(4-chloro-benzoyl)-1H-imidazole
10364-95-1

1-(4-chloro-benzoyl)-1H-imidazole

diethyl 2,6-dimethyl-4-benzyl-1,4-dihydropyridine-3,5-dicarboxylate
1539-57-7

diethyl 2,6-dimethyl-4-benzyl-1,4-dihydropyridine-3,5-dicarboxylate

4'-chloro-2-phenylacetophenone
1889-71-0

4'-chloro-2-phenylacetophenone

Conditions
ConditionsYield
With [4,4’-bis(1,1-dimethylethyl)-2,2’-bipyridine-N1,N1‘]bis [3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-N]phenyl-C]iridium(III) hexafluorophosphate; caesium carbonate; 1,4-dimethyl-1,2,4-triazolium iodide In acetonitrile at 20℃; Inert atmosphere; Irradiation; Sealed tube;76%
benzyl chloride
100-44-7

benzyl chloride

4-chloro-benzoyl chloride
122-01-0

4-chloro-benzoyl chloride

4'-chloro-2-phenylacetophenone
1889-71-0

4'-chloro-2-phenylacetophenone

Conditions
ConditionsYield
With nickel In 1,2-dimethoxyethane at 85℃; for 0.25h;72%
tris(4-chlorophenyl)bismuthane
5575-51-9

tris(4-chlorophenyl)bismuthane

phenylacetyl chloride
103-80-0

phenylacetyl chloride

A

4,4'-dichlorobiphenyl
2050-68-2

4,4'-dichlorobiphenyl

B

4'-chloro-2-phenylacetophenone
1889-71-0

4'-chloro-2-phenylacetophenone

Conditions
ConditionsYield
With bis-triphenylphosphine-palladium(II) chloride; triethylamine In tetrahydrofuran at 80℃; for 3h; Schlenk tube; Inert atmosphere;A n/a
B 71%
4-vinylbenzyl chloride
1073-67-2

4-vinylbenzyl chloride

benzenediazonium tetrafluoroborate
369-57-3

benzenediazonium tetrafluoroborate

4'-chloro-2-phenylacetophenone
1889-71-0

4'-chloro-2-phenylacetophenone

Conditions
ConditionsYield
With ascorbic acid In N,N-dimethyl-formamide at 20℃; for 20h; Cooling with ice;71%
N-Benzyl-N-(benzylsulfanyl-phenyl-methyl)-4-chloro-benzamide
80351-84-4

N-Benzyl-N-(benzylsulfanyl-phenyl-methyl)-4-chloro-benzamide

A

N-benzylidene benzylamine
780-25-6

N-benzylidene benzylamine

B

4'-chloro-2-phenylacetophenone
1889-71-0

4'-chloro-2-phenylacetophenone

C

S

S

Conditions
ConditionsYield
With lithium diisopropyl amide In tetrahydrofuran for 4h; Ambient temperature; addition, -70 deg C;A n/a
B 70%
C n/a
1-(4-Chloro-phenyl)-2-phenyl-1-quinazolin-4-yl-ethanol
187336-13-6

1-(4-Chloro-phenyl)-2-phenyl-1-quinazolin-4-yl-ethanol

4'-chloro-2-phenylacetophenone
1889-71-0

4'-chloro-2-phenylacetophenone

Conditions
ConditionsYield
With potassium cyanide In N,N-dimethyl-formamide at 80℃; for 1h;68%
1-(4-Chloro-phenyl)-2-phenyl-1-quinazolin-4-yl-ethanol
187336-13-6

1-(4-Chloro-phenyl)-2-phenyl-1-quinazolin-4-yl-ethanol

A

quinazoline-4-carbonitrile
36082-71-0

quinazoline-4-carbonitrile

B

quinazoline-4-carbonamide
16499-37-9

quinazoline-4-carbonamide

C

4-benzyl-quinazoline
92437-11-1

4-benzyl-quinazoline

D

4'-chloro-2-phenylacetophenone
1889-71-0

4'-chloro-2-phenylacetophenone

Conditions
ConditionsYield
With potassium cyanide In N,N-dimethyl-formamide at 80℃; for 1h;A 9%
B 10%
C 9%
D 68%
sodium p-chlorobenzenesulphinate
14752-66-0

sodium p-chlorobenzenesulphinate

phenylacetonitrile
140-29-4

phenylacetonitrile

4'-chloro-2-phenylacetophenone
1889-71-0

4'-chloro-2-phenylacetophenone

Conditions
ConditionsYield
With palladium(II) trifluoroacetate; trifluoroacetic acid; 6-methyl-2,2'-bipyridine In tetrahydrofuran; water at 100℃; for 1h; Microwave irradiation;66%
benzylic zinc mesylate

benzylic zinc mesylate

4-chloro-benzoyl chloride
122-01-0

4-chloro-benzoyl chloride

4'-chloro-2-phenylacetophenone
1889-71-0

4'-chloro-2-phenylacetophenone

Conditions
ConditionsYield
With copper(l) cyanide; lithium chloride In tetrahydrofuran at 0℃; for 2h; Inert atmosphere;60%
4-chloro-benzoyl chloride
122-01-0

4-chloro-benzoyl chloride

toluene
108-88-3

toluene

4'-chloro-2-phenylacetophenone
1889-71-0

4'-chloro-2-phenylacetophenone

Conditions
ConditionsYield
With dipotassium hydrogenphosphate; nickel(II) chloride hexahydrate; 4-acetoxybenzophenone; 4,4'-di-tert-butyl-2,2'-bipyridine at 35℃; for 48h; Inert atmosphere; Sealed tube; Irradiation; Schlenk technique;60%
1-(4-chlorophenyl)-3-phenyl-2,3-ditosyloxypropanone

1-(4-chlorophenyl)-3-phenyl-2,3-ditosyloxypropanone

4'-chloro-2-phenylacetophenone
1889-71-0

4'-chloro-2-phenylacetophenone

Conditions
ConditionsYield
With potassium hydroxide In ethanol Heating;58%
benzyl (N-benzyl-p-chlorobenzamido)methylsulfide
77863-85-5

benzyl (N-benzyl-p-chlorobenzamido)methylsulfide

4'-chloro-2-phenylacetophenone
1889-71-0

4'-chloro-2-phenylacetophenone

Conditions
ConditionsYield
With sodium hydride In tetrahydrofuran for 13h; Heating;55%
With sodium hydride In tetrahydrofuran for 13h; Heating;55%
4'-chloro-2-phenylacetophenone
1889-71-0

4'-chloro-2-phenylacetophenone

2-bromo-1-(4-chlorophenyl)-2-phenylethanone
1889-78-7

2-bromo-1-(4-chlorophenyl)-2-phenylethanone

Conditions
ConditionsYield
With bromine In diethyl ether for 0.5h;100%
With copper(II) nitrate trihydrate; hydrogen bromide; oxygen In acetic acid at 60℃; for 4.5h; Green chemistry;91%
With bromine In chloroform; acetic acid at 20℃; for 24h;86%
4'-chloro-2-phenylacetophenone
1889-71-0

4'-chloro-2-phenylacetophenone

4-chlorobenzil
22711-23-5

4-chlorobenzil

Conditions
ConditionsYield
With 1,4-diaza-bicyclo[2.2.2]octane In N,N-dimethyl-formamide at 90℃; for 24h;100%
With potassium hydrogencarbonate; dimethyl sulfoxide at 80℃;91%
With oxygen; copper(II) acetate monohydrate; potassium carbonate In N,N-dimethyl-formamide at 50℃; under 760.051 Torr; for 0.5h;87%
N,N-dimethyl-formamide dimethyl acetal
4637-24-5

N,N-dimethyl-formamide dimethyl acetal

4'-chloro-2-phenylacetophenone
1889-71-0

4'-chloro-2-phenylacetophenone

C17H16ClNO
611217-74-4

C17H16ClNO

Conditions
ConditionsYield
In toluene at 20 - 50℃; for 156h;100%
3-Iodotoluene
625-95-6

3-Iodotoluene

4'-chloro-2-phenylacetophenone
1889-71-0

4'-chloro-2-phenylacetophenone

1-(4-chlorophenyl)-2-phenyl-2-m-tolylethanone
1443223-40-2

1-(4-chlorophenyl)-2-phenyl-2-m-tolylethanone

Conditions
ConditionsYield
With copper(l) iodide; 1,10-Phenanthroline; caesium carbonate In 1,4-dioxane at 110℃; for 24h; Inert atmosphere;99%
3,5-dimethylphenyl iodide
22445-41-6

3,5-dimethylphenyl iodide

4'-chloro-2-phenylacetophenone
1889-71-0

4'-chloro-2-phenylacetophenone

1-(4-chlorophenyl)-2-(3,5-dimethylphenyl)-2-phenylethanone
1443223-42-4

1-(4-chlorophenyl)-2-(3,5-dimethylphenyl)-2-phenylethanone

Conditions
ConditionsYield
With copper(l) iodide; 1,10-Phenanthroline; caesium carbonate In 1,4-dioxane at 110℃; for 24h; Inert atmosphere;99%
With copper(l) iodide; caesium carbonate; 1,7-phenanthroline In 1,4-dioxane at 110℃; for 24h; Inert atmosphere;95%
4-fluoro-1-iodobenzene
352-34-1

4-fluoro-1-iodobenzene

4'-chloro-2-phenylacetophenone
1889-71-0

4'-chloro-2-phenylacetophenone

2-(4-fluorophenyl)-2-(4-chlorophenyl)-1-phenylethanone
1443223-60-6

2-(4-fluorophenyl)-2-(4-chlorophenyl)-1-phenylethanone

Conditions
ConditionsYield
With copper(l) iodide; 2-acetylcyclohexanone; caesium carbonate In tert-butyl alcohol at 70℃; for 24h; Inert atmosphere;99%
4'-chloro-2-phenylacetophenone
1889-71-0

4'-chloro-2-phenylacetophenone

(1S)-(-)-1-(4'-chlorophenyl)-2-phenylethanol
650601-10-8

(1S)-(-)-1-(4'-chlorophenyl)-2-phenylethanol

Conditions
ConditionsYield
With (S)-methyl oxazaboralidine; borane In tetrahydrofuran at 30℃; for 1h;98%
With D-glucose In ethanol; hexane; water; allyl alcohol at 50℃; for 168h; optical yield given as %ee; enantioselective reaction;
4'-chloro-2-phenylacetophenone
1889-71-0

4'-chloro-2-phenylacetophenone

(R)-1-(4'-chlorophenyl)-2-phenylethanol
811830-11-2

(R)-1-(4'-chlorophenyl)-2-phenylethanol

Conditions
ConditionsYield
With borane-THF In tetrahydrofuran at 30℃; for 16h; Inert atmosphere; optical yield given as %ee; enantioselective reaction;98%
Multi-step reaction with 2 steps
1: sodium tetrahydroborate / methanol; dichloromethane / 24 h / 20 °C
2: Pseudomonas cepacia lipase / tert-butyl methyl ether / 168 h / 20 °C / Resolution of racemate
View Scheme
Multi-step reaction with 2 steps
1: sodium tetrahydroborate / methanol; dichloromethane / 24 h / 20 °C
2: Porcine pancreas lipase type II / tert-butyl methyl ether / 264 h / 40 °C / Resolution of racemate
View Scheme
5,5-dimethyl-2-(2-methylallyl)-1,3,2-dioxaborinane
1398647-62-5

5,5-dimethyl-2-(2-methylallyl)-1,3,2-dioxaborinane

4'-chloro-2-phenylacetophenone
1889-71-0

4'-chloro-2-phenylacetophenone

(R)-2-(4-chlorophenyl)-4-methyl-1-phenylpent-4-en-2-ol
1428476-55-4

(R)-2-(4-chlorophenyl)-4-methyl-1-phenylpent-4-en-2-ol

Conditions
ConditionsYield
With (S)-3,3'-difluoro-1,1'-binaphthyl-2,2'-diol In tert-Amyl alcohol at 40℃; for 2h; Inert atmosphere; enantioselective reaction;97%
benzylacrylate
2495-35-4

benzylacrylate

4'-chloro-2-phenylacetophenone
1889-71-0

4'-chloro-2-phenylacetophenone

benzyl 5-(4-chlorophenyl)-5-oxo-4-phenylpentanoate

benzyl 5-(4-chlorophenyl)-5-oxo-4-phenylpentanoate

Conditions
ConditionsYield
With tetrabutylammonium tricarbonylnitrosylferrate In acetonitrile at 100℃; for 30h; Michael Addition; Inert atmosphere; Schlenk technique;97%
4'-chloro-2-phenylacetophenone
1889-71-0

4'-chloro-2-phenylacetophenone

1-(4-chlorophenyl)-2-phenylethanol
31233-66-6

1-(4-chlorophenyl)-2-phenylethanol

Conditions
ConditionsYield
With sodium tetrahydroborate In ethanol96%
With sodium tetrahydroborate In methanol; dichloromethane at 20℃; for 24h;94%
With C19H29N4Ru(1+)*C24H20B(1-); potassium hydroxide In isopropyl alcohol at 80℃; for 2h; Inert atmosphere; Schlenk technique;92%
1,2-diamino-benzene
95-54-5

1,2-diamino-benzene

4'-chloro-2-phenylacetophenone
1889-71-0

4'-chloro-2-phenylacetophenone

2-(4-chlorophenyl)-3-phenylquinoxaline
193145-75-4

2-(4-chlorophenyl)-3-phenylquinoxaline

Conditions
ConditionsYield
With 1,4-diaza-bicyclo[2.2.2]octane In N,N-dimethyl-formamide at 90℃; for 3h;96%
With [Cu(II)[5,11,17,23-tetrakis(trimethylammonium)-25,26,27,28-tetrahydroxycalix[4]arene](H2O)]I2; oxygen; potassium carbonate In water for 15h; Reflux; Green chemistry;88%
2-azido-1,3-dimethyl-4,5-dihydro-1H-imidazol-3-ium hexafluorophosphate (V)
1266134-54-6

2-azido-1,3-dimethyl-4,5-dihydro-1H-imidazol-3-ium hexafluorophosphate (V)

4'-chloro-2-phenylacetophenone
1889-71-0

4'-chloro-2-phenylacetophenone

C19H20ClN3O
1309977-03-4

C19H20ClN3O

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran; acetonitrile at 0℃; for 0.5h;96%
methanol
67-56-1

methanol

4'-chloro-2-phenylacetophenone
1889-71-0

4'-chloro-2-phenylacetophenone

1-(4-chlorophenyl)-2-phenyl-1-propanone
126866-24-8

1-(4-chlorophenyl)-2-phenyl-1-propanone

Conditions
ConditionsYield
With C34H27IrN2P(1+)*C32H12BF24(1-); caesium carbonate at 65℃; for 24h; Inert atmosphere;96%
With sodium hydroxide at 100℃; for 15h; Sealed tube; Autoclave; Inert atmosphere;85%
bromoacetic acid methyl ester
96-32-2

bromoacetic acid methyl ester

4'-chloro-2-phenylacetophenone
1889-71-0

4'-chloro-2-phenylacetophenone

β-p-Chlorbenzoyl-β-phenyl-propionsaeure-methylester
101441-22-9

β-p-Chlorbenzoyl-β-phenyl-propionsaeure-methylester

Conditions
ConditionsYield
With sodium hydride In dimethyl sulfoxide at 20℃; for 1h;95%
benzaldehyde
100-52-7

benzaldehyde

toluene-4-sulfonamide
70-55-3

toluene-4-sulfonamide

4'-chloro-2-phenylacetophenone
1889-71-0

4'-chloro-2-phenylacetophenone

(2S,3S)-1-(4-chlorophenyl)-2,3-diphenyl-3-(tosylamino)propan-1-one
1421353-67-4

(2S,3S)-1-(4-chlorophenyl)-2,3-diphenyl-3-(tosylamino)propan-1-one

Conditions
ConditionsYield
With C35H32F6N4OS In toluene at 0℃; for 35h; Mannich Aminomethylation; Molecular sieve; enantioselective reaction;95%
β-azidostyrene
16722-99-9

β-azidostyrene

4'-chloro-2-phenylacetophenone
1889-71-0

4'-chloro-2-phenylacetophenone

C22H16ClN3

C22H16ClN3

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In dimethyl sulfoxide at 25℃; for 0.82h; regioselective reaction;95%
2-Amino-5-chlorobenzophenone
719-59-5

2-Amino-5-chlorobenzophenone

4'-chloro-2-phenylacetophenone
1889-71-0

4'-chloro-2-phenylacetophenone

2-(4-chlorophenyl)-3,4-diphenyl-6-chloroquinoline
144757-84-6

2-(4-chlorophenyl)-3,4-diphenyl-6-chloroquinoline

Conditions
ConditionsYield
With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide In ethyl acetate at 60℃; Friedlaender synthesis;94%
ethylene glycol
107-21-1

ethylene glycol

phenethylamine
64-04-0

phenethylamine

4'-chloro-2-phenylacetophenone
1889-71-0

4'-chloro-2-phenylacetophenone

C24H20ClN

C24H20ClN

Conditions
ConditionsYield
With C34H27MnNO3P2(1+)*Br(1-); potassium tert-butylate In tert-Amyl alcohol at 135℃; for 24h;94%
4'-chloro-2-phenylacetophenone
1889-71-0

4'-chloro-2-phenylacetophenone

1,4-bis(4-chlorophenyl)-2,3-diphenylbutane-1,4-dione
36122-13-1

1,4-bis(4-chlorophenyl)-2,3-diphenylbutane-1,4-dione

Conditions
ConditionsYield
With silver fluoride In 5,5-dimethyl-1,3-cyclohexadiene at 140℃; for 4.5h;93%
With copper(II) acetate monohydrate In 5,5-dimethyl-1,3-cyclohexadiene at 140℃; for 2h;81%
In benzene Irradiation;
1-azidostyrene
16717-64-9

1-azidostyrene

4'-chloro-2-phenylacetophenone
1889-71-0

4'-chloro-2-phenylacetophenone

C22H16ClN3

C22H16ClN3

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In dimethyl sulfoxide at 25℃; for 0.5h; regioselective reaction;93%
2-aminopyridine
504-29-0

2-aminopyridine

4'-chloro-2-phenylacetophenone
1889-71-0

4'-chloro-2-phenylacetophenone

2-(4-chlorophenyl)-3-phenylimidazo[1,2-a]pyridine
342783-28-2

2-(4-chlorophenyl)-3-phenylimidazo[1,2-a]pyridine

Conditions
ConditionsYield
With potassium hydrogencarbonate In acetonitrile at 80℃; for 4h;91%
thiourea
17356-08-0

thiourea

4'-chloro-2-phenylacetophenone
1889-71-0

4'-chloro-2-phenylacetophenone

2-amino-4-(p-chlorophenyl)-5-phenylthiazole

2-amino-4-(p-chlorophenyl)-5-phenylthiazole

Conditions
ConditionsYield
With cesium bicarbonate; Bromotrichloromethane In acetonitrile at 80℃; for 2h;91%
1-azido-4-bromobenzene
2101-88-4

1-azido-4-bromobenzene

4'-chloro-2-phenylacetophenone
1889-71-0

4'-chloro-2-phenylacetophenone

1-(4-bromophenyl)-5-(4-chlorophenyl)-4-phenyl-1H-1,2,3-triazole

1-(4-bromophenyl)-5-(4-chlorophenyl)-4-phenyl-1H-1,2,3-triazole

Conditions
ConditionsYield
With tetra(n-butyl)ammonium hydrogensulfate; potassium hydroxide In water at 100℃; for 24h; Inert atmosphere; regioselective reaction;91%

1889-71-0Relevant articles and documents

-

Jenkins

, p. 682 (1934)

-

Electrochemical oxidation-induced benzyl C–H carbonylation for the synthesis of aromatic α-diketones

Tan, Yu-Fang,Chen, Yuan,Li, Rui-Xue,Guan, Zhi,He, Yan-Hong

supporting information, (2021/12/21)

Electrochemical oxidation-induced direct carbonylation of benzyl C–H bond for the synthesis of aromatic α-diketones is described. In this process, tetrabutylammonium iodide (nBu4NI) not only acts as an electrolyte, but its iodine anion is oxidized to an iodine radical at the anode, acting as a hydrogen atom transfer agent. The iodine radical extracts the benzyl hydrogen atom and causes the carbonylation of the benzyl position, where O2 in the air is used as an oxygen source.

Copper-Catalyzed Three-Component Carboboronation of Allenes Using Highly Strained Cyclic Ketimines as Electrophiles

Deng, Hao,Dong, Yujie,Shangguan, Yu,Yang, Fazhou,Han, Sheng,Wu, Jiaqi,Liang, Bo,Guo, Hongchao,Zhang, Cheng

supporting information, p. 4431 - 4435 (2021/05/26)

A diastereoselective copper and NHC-ligand-catalyzed three-component difunctionalization of allenes with bis(pinacolato)diboron and 2H-azirines to afford borylated allylaziridines is described. The reaction exhibits complete diastereoselectivity and good yields, and the further chlorination of the corresponding borylated products was also performed. It is believed that the high ring-strain force of 2H-azirines facilitates the reaction. More chemical transformations of borylated allylaziridines are also reported.

Palladium-catalyzed synthesis of α-aryl acetophenones from styryl ethers and aryl diazonium saltsviaregioselective Heck arylation at room temperature

Kandasamy, Jeyakumar,Lee, Yong Rok,Singh, Adesh Kumar,Venkatesh, Rapelly

, p. 7832 - 7837 (2021/09/28)

Preparation of α-aryl acetophenones from styryl ethers and aryldiazonium salts is described. The reaction is catalyzed by palladium acetate at room temperature in the absence of ligand and base. The developed method is highly attractive in terms of reaction conditions, substrate scope, functional group tolerance and yields. Synthetic applications of the present method are demonstrated by preparing α-aryl indoles and 3-aryl isocoumarin from styryl ethers.

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