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445-27-2 Usage

Chemical Properties

clear colorless to light yellow or light green

Uses

2'-Fluoroacetophenone is used as starting reagent in the synthesis of ascididemin. It is used to produce 1-(2-piperidin-1-yl-phenyl)-ethanone by reaction with piperidine.

Synthesis Reference(s)

Tetrahedron Letters, 31, p. 6179, 1990 DOI: 10.1016/S0040-4039(00)97018-7

General Description

The enantioselective reduction of 2′-fluoroacetophenone has been investigated.

Check Digit Verification of cas no

The CAS Registry Mumber 445-27-2 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 4,4 and 5 respectively; the second part has 2 digits, 2 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 445-27:
(5*4)+(4*4)+(3*5)+(2*2)+(1*7)=62
62 % 10 = 2
So 445-27-2 is a valid CAS Registry Number.

445-27-2 Well-known Company Product Price

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  • CAS number
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  • Alfa Aesar

  • (A15128)  2'-Fluoroacetophenone, 97%   

  • 445-27-2

  • 5g

  • 281.0CNY

  • Detail
  • Alfa Aesar

  • (A15128)  2'-Fluoroacetophenone, 97%   

  • 445-27-2

  • 25g

  • 1055.0CNY

  • Detail
  • Alfa Aesar

  • (A15128)  2'-Fluoroacetophenone, 97%   

  • 445-27-2

  • 100g

  • 3795.0CNY

  • Detail

445-27-2SDS

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 2'-Fluoroacetophenone

1.2 Other means of identification

Product number -
Other names 2′-Fluoroacetophenone

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:445-27-2 SDS

445-27-2Synthetic route

1-(2-fluorophenyl)ethanol
445-26-1

1-(2-fluorophenyl)ethanol

2'-Fluoroacetophenone
445-27-2

2'-Fluoroacetophenone

Conditions
ConditionsYield
With [(2-(benzoimidazol-2-yl)-6-(3,5-dimethylpyrazol-1-yl)pyridine)RuCl2(PPh3)]; potassium tert-butylate; acetone In methanol at 56℃; under 750.075 Torr; for 0.5h; Catalytic behavior; Oppenauer Oxidation; Inert atmosphere;97%
With Langlois reagent In acetonitrile at 25℃; for 12h; Irradiation; Sealed tube;89%
With calcomenite; potassium hydroxide In toluene for 28h; Reflux;87%
1-fluoro-2-(prop-1-en-2-yl)benzene
344-73-0

1-fluoro-2-(prop-1-en-2-yl)benzene

2'-Fluoroacetophenone
445-27-2

2'-Fluoroacetophenone

Conditions
ConditionsYield
With iron(III) trifluoromethanesulfonate; C65H77N5O4S2; oxygen In 1,2-dichloro-ethane at 75℃; under 760.051 Torr; for 24h; Green chemistry; chemoselective reaction;97%
(2-fluorophenyl)acetylene
766-49-4

(2-fluorophenyl)acetylene

2'-Fluoroacetophenone
445-27-2

2'-Fluoroacetophenone

Conditions
ConditionsYield
With C22H20AuN3O2P(1+)*CF3O3S(1-); water; silver trifluoromethanesulfonate; acetic acid at 100℃; for 10h;93%
With silver trifluoromethanesulfonate In water; acetic acid at 110℃; for 6h; Schlenk technique;87%
With p-toluenesulfonic acid monohydrate; acetic acid In dichloromethane at 80℃; for 8h; Sealed tube;80%
methyllithium
917-54-4

methyllithium

o-fluoro-benzoic acid
445-29-4

o-fluoro-benzoic acid

2'-Fluoroacetophenone
445-27-2

2'-Fluoroacetophenone

Conditions
ConditionsYield
Stage #1: methyllithium With copper(l) cyanide In diethyl ether at 0℃; for 0.0833333h; Inert atmosphere;
Stage #2: o-fluoro-benzoic acid In diethyl ether at 0 - 20℃; for 15h; Inert atmosphere;
90%
o-fluorophenylboronic acid
1993-03-9

o-fluorophenylboronic acid

acetonitrile
75-05-8

acetonitrile

2'-Fluoroacetophenone
445-27-2

2'-Fluoroacetophenone

Conditions
ConditionsYield
With 1,10-Phenanthroline; nickel(II) bromide 2-methoxyethyl ether complex; sodium hydrogencarbonate In water at 100℃; for 5h; Autoclave;89%
2-Fluorobenzoyl chloride
393-52-2

2-Fluorobenzoyl chloride

diethyl malonate
105-53-3

diethyl malonate

2'-Fluoroacetophenone
445-27-2

2'-Fluoroacetophenone

Conditions
ConditionsYield
Stage #1: diethyl malonate With ethanol; magnesium In tetrachloromethane; tert-butyl methyl ether for 3h; Reflux; Large scale;
Stage #2: 2-Fluorobenzoyl chloride In tert-butyl methyl ether for 0.25h; Reflux; Large scale;
Stage #3: With sulfuric acid; water; acetic acid In tert-butyl methyl ether for 4h; Reagent/catalyst; Reflux; Large scale;
83%
acetophenone
98-86-2

acetophenone

2'-Fluoroacetophenone
445-27-2

2'-Fluoroacetophenone

Conditions
ConditionsYield
With palladium diacetate; silver nitrate; N-fluorobis(benzenesulfon)imide; methyl carbamate In dichloromethane at 95℃; for 12h; Catalytic behavior; Solvent; Sealed tube;82%
Multi-step reaction with 3 steps
1: sodium acetate / ethanol; water / 2 h / Reflux
2: tris(dibenzylideneacetone)dipalladium(0) chloroform complex; N-fluorobis(benzenesulfon)imide; potassium nitrate / nitromethane / 24 h / 25 °C
3: hydrogenchloride; water / diethyl ether / 30 h / 20 °C
View Scheme
o-fluorobromobenzene
1072-85-1

o-fluorobromobenzene

-butyl vinyl ether
111-34-2

-butyl vinyl ether

2'-Fluoroacetophenone
445-27-2

2'-Fluoroacetophenone

Conditions
ConditionsYield
With 1,3-bis-(diphenylphosphino)propane; diisopropylamine; 1-butyl-3-methylimidazolium Tetrafluoroborate; palladium diacetate In dimethyl sulfoxide at 115℃; for 36h; Heck arylation;81%
2-fluorobenzenesulfonyl hydrazide

2-fluorobenzenesulfonyl hydrazide

acetonitrile
75-05-8

acetonitrile

2'-Fluoroacetophenone
445-27-2

2'-Fluoroacetophenone

Conditions
ConditionsYield
With 1,10-Phenanthroline; water; palladium diacetate at 100℃; under 760.051 Torr; for 6h;81%
1-(2,2-dibromovinyl)-2-fluorobenzene
401514-42-9

1-(2,2-dibromovinyl)-2-fluorobenzene

2'-Fluoroacetophenone
445-27-2

2'-Fluoroacetophenone

Conditions
ConditionsYield
With water; zinc at 275℃; for 4h;79%
1-Fluoro-2-iodobenzene
348-52-7

1-Fluoro-2-iodobenzene

acetic anhydride
108-24-7

acetic anhydride

2'-Fluoroacetophenone
445-27-2

2'-Fluoroacetophenone

Conditions
ConditionsYield
With tris(dibenzylideneacetone)dipalladium (0); N-ethyl-N,N-diisopropylamine; lithium chloride In N,N-dimethyl-formamide at 100℃; for 8.5h;74%
o-fluorophenylboronic acid
1993-03-9

o-fluorophenylboronic acid

ethyl 2-cyanoacetate
105-56-6

ethyl 2-cyanoacetate

2'-Fluoroacetophenone
445-27-2

2'-Fluoroacetophenone

Conditions
ConditionsYield
With trifluorormethanesulfonic acid; water; palladium diacetate; 2-(3,5-dimethyl-1H-pyrazol-1-yl)pyridine at 60℃; for 5h; regioselective reaction;72%
2-fluorostyrene
394-46-7

2-fluorostyrene

2'-Fluoroacetophenone
445-27-2

2'-Fluoroacetophenone

Conditions
ConditionsYield
With tert.-butylhydroperoxide; C21H19N5Pd(2+)*2BF4(1-) In decane; acetonitrile at 45℃; for 30h; Wacker Oxidation;70%
With manganese(II) bromide; water; lithium perchlorate; copper dichloride In acetonitrile at 60℃; for 8h; Wacker-Tsuji Olefin Oxidation; Sealed tube; Inert atmosphere; Electrochemical reaction; regioselective reaction;46%
With oxygen; potassium carbonate; isopropyl alcohol at 150℃; under 3000.3 Torr; for 6h; regioselective reaction;82.3 %Chromat.
2'-fluoroacetophenone oxime
364-81-8

2'-fluoroacetophenone oxime

2'-Fluoroacetophenone
445-27-2

2'-Fluoroacetophenone

Conditions
ConditionsYield
Stage #1: 2'-fluoroacetophenone oxime With hexachlorodisilane; silica gel In toluene at 110℃; for 8h;
Stage #2: With water In toluene for 0.5h;
67%
With ruthenium trichloride; toluene-4-sulfonic acid In N,N-dimethyl acetamide; water at 120℃; under 760.051 Torr; for 8h; Inert atmosphere; Green chemistry;61%
2-(2-fluorophenyl)propane-1,2-diol
1547526-82-8

2-(2-fluorophenyl)propane-1,2-diol

2'-Fluoroacetophenone
445-27-2

2'-Fluoroacetophenone

Conditions
ConditionsYield
With oxygen; sodium carbonate In water at 20℃; for 5h; Irradiation; Green chemistry;51%
1-fluoro-2-iso-propylbenzene
2022-67-5

1-fluoro-2-iso-propylbenzene

2'-Fluoroacetophenone
445-27-2

2'-Fluoroacetophenone

Conditions
ConditionsYield
With oxygen at 150℃; under 760.051 Torr; for 24h; Autoclave;36%
2-Fluorobenzoyl chloride
393-52-2

2-Fluorobenzoyl chloride

2'-Fluoroacetophenone
445-27-2

2'-Fluoroacetophenone

Conditions
ConditionsYield
With dimethylcadmium; benzene
1-(2-Fluoro-4-trimethylsilanyl-phenyl)-ethanone
128254-28-4

1-(2-Fluoro-4-trimethylsilanyl-phenyl)-ethanone

2'-Fluoroacetophenone
445-27-2

2'-Fluoroacetophenone

Conditions
ConditionsYield
With potassium fluoride In N,N-dimethyl-formamide at -40℃; for 3h; Yield given;
1-Fluoro-2-iodobenzene
348-52-7

1-Fluoro-2-iodobenzene

acetyl chloride
75-36-5

acetyl chloride

2'-Fluoroacetophenone
445-27-2

2'-Fluoroacetophenone

Conditions
ConditionsYield
With copper 1) THF, 25 deg C, 10 min, 2a) 25 deg C, 30 min; Yield given. Multistep reaction;
With CuI*P(Et)3; naphthalen-1-yl-lithium 1.) DME, 25 deg C, 10 min, 2.) 25 deg C, 30 min; Yield given. Multistep reaction;
acetophenone
98-86-2

acetophenone

A

2'-Fluoroacetophenone
445-27-2

2'-Fluoroacetophenone

B

1-(4-fluorophenyl)ethanone
403-42-9

1-(4-fluorophenyl)ethanone

C

1-(3-fluorophenyl)ethanone
455-36-7

1-(3-fluorophenyl)ethanone

Conditions
ConditionsYield
With cobalt (III) fluoride In chloroform for 18h; Product distribution; Heating;
2-Fluoro-1,4-bis-trimethylsilanyl-benzene
128254-27-3

2-Fluoro-1,4-bis-trimethylsilanyl-benzene

acetyl chloride
75-36-5

acetyl chloride

2'-Fluoroacetophenone
445-27-2

2'-Fluoroacetophenone

Conditions
ConditionsYield
With aluminium trichloride; water; fluoride Multistep reaction;
fluorosulphonic acid
7789-21-1

fluorosulphonic acid

acetophenone
98-86-2

acetophenone

A

2'-Fluoroacetophenone
445-27-2

2'-Fluoroacetophenone

B

2,3-difluoroacetophenone
18355-80-1

2,3-difluoroacetophenone

Conditions
ConditionsYield
at 110℃;
methyl magnesium iodide
917-64-6

methyl magnesium iodide

etheric solution of 2-fluoro-benzonitrile

etheric solution of 2-fluoro-benzonitrile

2'-Fluoroacetophenone
445-27-2

2'-Fluoroacetophenone

Conditions
ConditionsYield
Erhitzen des von Aether befreiten Reaktionsgemisches auf dem Dampfbad und anschliessendes Behandeln mit wss. Essigsaeure;
acetophenone
98-86-2

acetophenone

A

2'-Fluoroacetophenone
445-27-2

2'-Fluoroacetophenone

B

1-(3,3,6,6-tetrafluoro-1,4-cyclohexyldienyl)-1-ethanone
69291-63-0

1-(3,3,6,6-tetrafluoro-1,4-cyclohexyldienyl)-1-ethanone

C

2',5'-difluoroacetophenone
1979-36-8

2',5'-difluoroacetophenone

D

1-(3-fluorophenyl)ethanone
455-36-7

1-(3-fluorophenyl)ethanone

Conditions
ConditionsYield
With hydrogen fluoride In diethyl ether; acetone at 5℃; for 18h; Electrochemical reaction;
1-(1-butoxy-vinyl)-2-fluoro-benzene
839721-38-9

1-(1-butoxy-vinyl)-2-fluoro-benzene

2'-Fluoroacetophenone
445-27-2

2'-Fluoroacetophenone

Conditions
ConditionsYield
With hydrogenchloride for 0.5h;
With hydrogenchloride; water In isopropyl alcohol for 0.5h;
With hydrogenchloride; water In ethylene glycol Inert atmosphere;
With hydrogenchloride; water In diethyl ether at 20℃; for 1h; Inert atmosphere;
With hydrogenchloride In acetone at 20℃; for 1h;
o-fluorobromobenzene
1072-85-1

o-fluorobromobenzene

2'-Fluoroacetophenone
445-27-2

2'-Fluoroacetophenone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1,3-bis(diphenylphosphino)propane; Pd(OAc)2; Et3N / 1-butyl-3-methylimidazolium tetrafluoroborate / 36 h / 115 °C
2: aq. HCl / 0.5 h
View Scheme
2-Fluorobenzaldehyde
446-52-6

2-Fluorobenzaldehyde

2'-Fluoroacetophenone
445-27-2

2'-Fluoroacetophenone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: diethyl ether
2: pyridinium chlorochromate / CH2Cl2
View Scheme
2-Fluoro-1,4-bis-trimethylsilanyl-benzene
128254-27-3

2-Fluoro-1,4-bis-trimethylsilanyl-benzene

2'-Fluoroacetophenone
445-27-2

2'-Fluoroacetophenone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: AlCl3
2: KF / dimethylformamide / 3 h / -40 °C
View Scheme
methylmagnesium bromide
75-16-1

methylmagnesium bromide

2-Fluorobenzaldehyde
446-52-6

2-Fluorobenzaldehyde

2'-Fluoroacetophenone
445-27-2

2'-Fluoroacetophenone

Conditions
ConditionsYield
Stage #1: methylmagnesium bromide; 2-Fluorobenzaldehyde In tetrahydrofuran
Stage #2: With pyridinium chlorochromate In dichloromethane
2'-Fluoroacetophenone
445-27-2

2'-Fluoroacetophenone

1-(2-fluorophenyl)ethanol
445-26-1

1-(2-fluorophenyl)ethanol

Conditions
ConditionsYield
Stage #1: 2'-Fluoroacetophenone 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%
With C40H37ClN2PRuS(1+)*C24H20B(1-); isopropyl alcohol; potassium hydroxide at 82℃; for 2h; Catalytic behavior;100%
With [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; sodium formate; ephedrine hydrochloride at 20℃;99%
2'-Fluoroacetophenone
445-27-2

2'-Fluoroacetophenone

A

(1S)-1-(2-fluorophenyl)ethanol
171032-87-4

(1S)-1-(2-fluorophenyl)ethanol

B

(R)-1-(2-fluorophenyl)ethanol
162427-79-4

(R)-1-(2-fluorophenyl)ethanol

Conditions
ConditionsYield
With RuBr2[(S,S)-2,4-bis(diphenylphosphino)pentane](2-picolylamine); potassium tert-butylate; hydrogen In ethanol at 40℃; under 7600.51 Torr; for 19h; Inert atmosphere; Autoclave;A 100%
B n/a
With dimethylsulfide borane complex; (S)-tetrahydro-1-butyl-3,3-diphenyl-1H,3H-pyrrolo{2,1-c}{1,3,2}oxazaborole In tetrahydrofuran for 0.166667h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
With Cp*RhCl<(R,R)-Tscydn>; potassium tert-butylate In isopropyl alcohol at 30℃; for 12h; Yield given; Yields of byproduct given. Title compound not separated from byproducts;
2'-Fluoroacetophenone
445-27-2

2'-Fluoroacetophenone

(1S)-1-(2-fluorophenyl)ethanol
171032-87-4

(1S)-1-(2-fluorophenyl)ethanol

Conditions
ConditionsYield
With [((R,R)-diphenylethylenediamine)((R)-Binap)dichlororuthenium(II)]; potassium tert-butylate; hydrogen In isopropyl alcohol at 26 - 30℃; under 3040 Torr; for 3h;100%
With tris(bis(trimethylsilyl)amido)lanthanum(III); 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane; ((2S,2'S)-((2-hydroxy-5-methyl-1,3-phenylene)bis(methylene))bis(pyrrolidine-1,2-diyl))bis(diphenylmethanol) In tetrahydrofuran at 0℃; for 8h; enantioselective reaction;99%
In phosphate buffer for 48h; Microbiological reaction;98%
2'-Fluoroacetophenone
445-27-2

2'-Fluoroacetophenone

(R)-1-(2-fluorophenyl)ethanol
162427-79-4

(R)-1-(2-fluorophenyl)ethanol

Conditions
ConditionsYield
With (S,S)-RuCl2(2,2'-bis(di-3,5-xylylphosphino)-1,1'-binaphthyl)(1,1-dianisyl-2-isopropyl-1,2-ethylenediamine); potassium tert-butylate; hydrogen In isopropyl alcohol at 26 - 30℃; under 6080 Torr; for 13h;100%
With water; sodium formate; sodium dodecyl-sulfate at 39.84℃; for 96h; Inert atmosphere; optical yield given as %ee; enantioselective reaction;95%
With bromopentacarbonylmanganese(I); hydrogen; C45H43FeNP2; potassium hydroxide In methanol; toluene at 20℃; for 36h; enantioselective reaction;93%
2'-Fluoroacetophenone
445-27-2

2'-Fluoroacetophenone

(S)-1-phenyl-ethylamine
2627-86-3

(S)-1-phenyl-ethylamine

[1-(3-Fluoro-phenyl)-eth-(E)-ylidene]-((S)-1-phenyl-ethyl)-amine
444643-06-5

[1-(3-Fluoro-phenyl)-eth-(E)-ylidene]-((S)-1-phenyl-ethyl)-amine

Conditions
ConditionsYield
zinc(II) chloride In toluene for 15h; Heating;100%
2'-Fluoroacetophenone
445-27-2

2'-Fluoroacetophenone

2'-fluoroacetophenone oxime
364-81-8

2'-fluoroacetophenone oxime

Conditions
ConditionsYield
With hydroxylamine hydrochloride; sodium acetate In ethanol; water at 95℃;100%
With hydroxylamine hydrochloride; sodium hydroxide In ethanol; water at 25℃; for 4h;94.7%
With hydroxylamine hydrochloride; sodium acetate In ethanol; water Heating;
2'-Fluoroacetophenone
445-27-2

2'-Fluoroacetophenone

Benzylhydrazine
555-96-4

Benzylhydrazine

C15H15FN2

C15H15FN2

Conditions
ConditionsYield
With acetic acid In ethanol for 12h; Reflux; Inert atmosphere;100%
morpholine
110-91-8

morpholine

2'-Fluoroacetophenone
445-27-2

2'-Fluoroacetophenone

C12H14FNO
1606165-14-3

C12H14FNO

Conditions
ConditionsYield
In toluene at -43 - 20℃; for 6.5h; Inert atmosphere;100%
2'-Fluoroacetophenone
445-27-2

2'-Fluoroacetophenone

salicylaldehyde
90-02-8

salicylaldehyde

(E)-1-(2-Fluoro-phenyl)-3-(2-hydroxy-phenyl)-propenone

(E)-1-(2-Fluoro-phenyl)-3-(2-hydroxy-phenyl)-propenone

Conditions
ConditionsYield
With potassium hydroxide In ethanol for 1h; Ambient temperature;99%
trimethylsilyl cyanide
7677-24-9

trimethylsilyl cyanide

2'-Fluoroacetophenone
445-27-2

2'-Fluoroacetophenone

2-(2'-fluorophenyl)-2-(trimethylsilyloxy)propanonitrile

2-(2'-fluorophenyl)-2-(trimethylsilyloxy)propanonitrile

Conditions
ConditionsYield
N,N,N',N'-tetramethylguanidine at 25℃; for 15h;99%
With C42H50Mg2N4 In benzene-d6 at 25℃; for 0.8h; Glovebox; Inert atmosphere;99%
Fe(Cp)2PF6 at 20℃; for 0.166667h;94%
2'-Fluoroacetophenone
445-27-2

2'-Fluoroacetophenone

2-propanethiol
75-33-2

2-propanethiol

1-(2-(isopropylthio)phenyl)ethan-1-one
918811-12-8

1-(2-(isopropylthio)phenyl)ethan-1-one

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 50℃;99%
piperonal
120-57-0

piperonal

2'-Fluoroacetophenone
445-27-2

2'-Fluoroacetophenone

(E)-3-(benzo[d][1,3]dioxol-5-yl)-1-(2-fluorophenyl)prop-2-en-1-one
1352346-99-6

(E)-3-(benzo[d][1,3]dioxol-5-yl)-1-(2-fluorophenyl)prop-2-en-1-one

Conditions
ConditionsYield
With sodium hydroxide In ethanol; water at 20℃;99%
trimethylsilyl cyanide
7677-24-9

trimethylsilyl cyanide

2'-Fluoroacetophenone
445-27-2

2'-Fluoroacetophenone

(S)-2-(2-fluorophenyl)-2-((trimethylsilyl)oxy)propanenitrile

(S)-2-(2-fluorophenyl)-2-((trimethylsilyl)oxy)propanenitrile

Conditions
ConditionsYield
Stage #1: 2'-Fluoroacetophenone With C38H26LiO5P In hexane; water; toluene at -78℃; for 0.166667h; Inert atmosphere;
Stage #2: trimethylsilyl cyanide In hexane; water; toluene at -78℃; for 4h; Inert atmosphere; enantioselective reaction;
99%
Conditions
ConditionsYield
With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; C51H41F4NO6P2; mesitylcopper(I) at 30℃; for 40h; diastereoselective reaction;99%
2'-Fluoroacetophenone
445-27-2

2'-Fluoroacetophenone

4-methoxy-benzaldehyde
123-11-5

4-methoxy-benzaldehyde

3-(4-methoxyphenyl)-1-(2-fluorophenyl)-2-propen-1-one
130581-22-5

3-(4-methoxyphenyl)-1-(2-fluorophenyl)-2-propen-1-one

Conditions
ConditionsYield
With methanol; sodium In methanol at 20℃; Aldol Condensation;98.4%
trimethyl (3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)prop-1-yn-1-yl)silane
129217-85-2

trimethyl (3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)prop-1-yn-1-yl)silane

2'-Fluoroacetophenone
445-27-2

2'-Fluoroacetophenone

(R)-2-(2-fluorophenyl)-5-(trimethylsilyl)pent-4-yn-2-ol
1312791-19-7

(R)-2-(2-fluorophenyl)-5-(trimethylsilyl)pent-4-yn-2-ol

Conditions
ConditionsYield
With copper (II) isobutyrate; (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl; lithium tert-butoxide In tetrahydrofuran at -62℃; for 16h; Inert atmosphere; optical yield given as %ee; enantioselective reaction;98%
2'-Fluoroacetophenone
445-27-2

2'-Fluoroacetophenone

2-bromo-2'-fluoroacetophenone
655-15-2

2-bromo-2'-fluoroacetophenone

Conditions
ConditionsYield
With bromine; acetic acid at 20℃; for 2h;97%
With bromine In acetic acid at 20℃; for 2h;97%
With copper(I) bromide In ethyl acetate at 80℃;95%
2'-Fluoroacetophenone
445-27-2

2'-Fluoroacetophenone

1-(2-fluoro-5-nitrophenyl)ethanone
79110-05-7

1-(2-fluoro-5-nitrophenyl)ethanone

Conditions
ConditionsYield
With sulfuric acid; nitric acid at -42℃; for 0.5h;97%
Stage #1: 2'-Fluoroacetophenone With sulfuric acid; nitric acid at -40℃; for 1.08333h;
Stage #2: With water Cooling with ice;
97%
With sulfuric acid; nitric acid In water at -10 - 5℃; for 0.5h;93.7%
2'-Fluoroacetophenone
445-27-2

2'-Fluoroacetophenone

thiourea
17356-08-0

thiourea

4-(o-fluorophenyl)-1,3-thiazol-2-amine

4-(o-fluorophenyl)-1,3-thiazol-2-amine

Conditions
ConditionsYield
With iodine at 100℃;97%
With iodine at 100℃; for 8h;66%
With iodine; dimethyl sulfoxide at 80℃; for 12h; Schlenk technique;52%
2'-Fluoroacetophenone
445-27-2

2'-Fluoroacetophenone

N-carbethoxy-4-tropinone

N-carbethoxy-4-tropinone

3-(2-fluoro-phenylethynyl)-8-aza-bicyclo[3.2.1]oct-2-ene-8-carboxylic acid ethyl ester

3-(2-fluoro-phenylethynyl)-8-aza-bicyclo[3.2.1]oct-2-ene-8-carboxylic acid ethyl ester

Conditions
ConditionsYield
Stage #1: 2'-Fluoroacetophenone; N-carbethoxy-4-tropinone With Nonafluorobutanesulfonyl fluoride; tert-butylimino-tri(pyrrolidino)phosphorane; lithium chloride In N,N-dimethyl-formamide at 10 - 25℃;
Stage #2: With copper(l) iodide; diisopropylamine; triphenylphosphine; palladium diacetate In N,N-dimethyl-formamide at 60℃; for 5.5h; Sonogashira coupling;
97%
potassium cyanide

potassium cyanide

2'-Fluoroacetophenone
445-27-2

2'-Fluoroacetophenone

ammonium carbonate
506-87-6

ammonium carbonate

(RS)-5-(2-fluoro-phenyl)-5-methyl-imidazolidine-2,4-dione
7248-25-1

(RS)-5-(2-fluoro-phenyl)-5-methyl-imidazolidine-2,4-dione

Conditions
ConditionsYield
With ammonium hydroxide In ethanol; water at 60℃; for 5.5h;97%
With ammonium hydroxide In ethanol; water at 60℃; for 5.5h;97%
In ethanol at 50℃; for 24h; Bucherer-Bergs Reaction;
2'-Fluoroacetophenone
445-27-2

2'-Fluoroacetophenone

Benzimidazol-2-thiol
134469-07-1

Benzimidazol-2-thiol

2-{[2-(2-fluorophenyl)-2-oxoethyl]thio}-1H-benzo[d]imidazol-3-ium sulfate

2-{[2-(2-fluorophenyl)-2-oxoethyl]thio}-1H-benzo[d]imidazol-3-ium sulfate

Conditions
ConditionsYield
With sulfuric acid; acetic acid for 0.5h; Reflux;97%
2'-Fluoroacetophenone
445-27-2

2'-Fluoroacetophenone

benzaldehyde
100-52-7

benzaldehyde

aniline
62-53-3

aniline

C21H18FNO

C21H18FNO

Conditions
ConditionsYield
With C7H13N2O3S(1+)*C10H15O4S(1-) at 25℃; for 0.25h; Mannich Aminomethylation;97%
2'-Fluoroacetophenone
445-27-2

2'-Fluoroacetophenone

ethyl 2-sulfanylacetate
623-51-8

ethyl 2-sulfanylacetate

ethyl 3-methyl-1-benzothiophene-2-carboxylate
31310-22-2

ethyl 3-methyl-1-benzothiophene-2-carboxylate

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 75℃; for 16h; Inert atmosphere;97%
2'-Fluoroacetophenone
445-27-2

2'-Fluoroacetophenone

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-fluorophenyl)pent-4-en-2-ol
1071821-42-5

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

Conditions
ConditionsYield
With ethanol; diethylzinc In tetrahydrofuran at 20℃; for 2h; Inert atmosphere;96%
With indium In water at 30℃; for 24h; Inert atmosphere;91%
2-Aminobenzyl alcohol
5344-90-1

2-Aminobenzyl alcohol

2'-Fluoroacetophenone
445-27-2

2'-Fluoroacetophenone

2-(2-fluorophenyl)quinoline
2836-41-1

2-(2-fluorophenyl)quinoline

Conditions
ConditionsYield
With C22H24ClN3ORu; potassium hydroxide In toluene at 80℃; for 5h; Catalytic behavior; Green chemistry;96%
With copper(l) iodide; 1,10-Phenanthroline; potassium carbonate In tetrahydrofuran at 20℃; for 12h;96%
With caesium carbonate In toluene at 120℃; for 10h; Schlenk technique; Inert atmosphere;71%
piperidine
110-89-4

piperidine

formaldehyd
50-00-0

formaldehyd

2'-Fluoroacetophenone
445-27-2

2'-Fluoroacetophenone

1-(2-fluoro-phenyl)-3-piperidin-1-yl-propan-1-one

1-(2-fluoro-phenyl)-3-piperidin-1-yl-propan-1-one

Conditions
ConditionsYield
With C7H13N2O3S(1+)*C10H15O4S(1-) at 25℃; for 0.416667h; Mannich Aminomethylation;96%
piperazine
110-85-0

piperazine

formaldehyd
50-00-0

formaldehyd

2'-Fluoroacetophenone
445-27-2

2'-Fluoroacetophenone

C13H17FN2O

C13H17FN2O

Conditions
ConditionsYield
With C7H13N2O3S(1+)*C10H15O4S(1-) at 25℃; for 0.416667h; Mannich Aminomethylation;96%

445-27-2Relevant articles and documents

Pd-Catalysed direct C(sp2)-H fluorination of aromatic ketones: Concise access to anacetrapib

Wu, Qiuzi,Mao, Yang-Jie,Zhou, Kun,Wang, Shuang,Chen, Lei,Xu, Zhen-Yuan,Lou, Shao-Jie,Xu, Dan-Qian

supporting information, p. 4544 - 4547 (2021/05/17)

The Pd-cataylsed direct ortho-C(sp2)-H fluorination of aromatic ketones has been developed for the first time. The reaction features good regioselectivity and simple operations, constituting an alternative shortcut to access fluorinated ketones. A concise synthesis of anacetrapib has also been achieved by using late-stage C-H fluorination as a key step.

Decatungstate-mediated solar photooxidative cleavage of CC bonds using air as an oxidant in water

Du, Dongdong,Luo, Junfei,Shi, Sanshan,Xie, Pan,Xue, Cheng

, p. 5936 - 5943 (2021/08/23)

With the increasing attention for green chemistry and sustainable development, there has been much interest in searching for greener methods and sources in organic synthesis. However, toxic additives or solvents are inevitably involved in most organic transformations. Herein, we first report the combination of direct utilization of solar energy, air as the oxidant and water as the solvent for the selective cleavage of CC double bonds in aryl olefins. Various α-methyl styrenes, diaryl alkenes as well as terminal styrenes are well tolerated in this green and sustainable strategy and furnished the desired carbonyl products in satisfactory yields. Like heterogeneous catalysis, this homogeneous catalytic system could also be reused and it retains good activity even after repeating three times. Mechanism investigations indicated that both O2- and 1O2 were involved in the reaction. Based on these results, two possible mechanisms, including the electron transfer pathway and the energy transfer pathway, were proposed.

A sodium trifluoromethanesulfinate-mediated photocatalytic strategy for aerobic oxidation of alcohols

Zhu, Xianjin,Liu, Can,Liu, Yong,Yang, Haijun,Fu, Hua

, p. 12443 - 12446 (2020/10/30)

A sodium trifluoromethanesulfinate-mediated photocatalytic strategy for the aerobic oxidation of alcohols has been developed for the first time, and the photoredox aerobic oxidation of secondary and primary alcohols provided the corresponding ketones and carboxylic acids, respectively, in high to excellent yields.

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