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2142-68-9

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2142-68-9 Usage

Uses

Different sources of media describe the Uses of 2142-68-9 differently. You can refer to the following data:
1. 2''-Chloroacetophenone (cas# 2142-68-9) is a compound useful in organic synthesis.
2. 2′-Chloroacetophenone was employed as model substrate to investigate the enzymatic performance of Aspergillus terreus and Rhizopus oryzae in enantioselective bioreductions using glycerol as a co-solvent.

General Description

2′-Chloroacetophenone undergoes stereoselective reduction to (R)-2′-chloro-1-phenyl-ethanol by Saccharomyces cerevisiae B5. It is commonly used as lacrimator.

Check Digit Verification of cas no

The CAS Registry Mumber 2142-68-9 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 8 respectively.
Calculate Digit Verification of CAS Registry Number 2142-68:
(6*2)+(5*1)+(4*4)+(3*2)+(2*6)+(1*8)=59
59 % 10 = 9
So 2142-68-9 is a valid CAS Registry Number.

2142-68-9 Well-known Company Product Price

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  • Alfa Aesar

  • (A15232)  2'-Chloroacetophenone, 98%   

  • 2142-68-9

  • 50g

  • 554.0CNY

  • Detail
  • Alfa Aesar

  • (A15232)  2'-Chloroacetophenone, 98%   

  • 2142-68-9

  • 250g

  • 1403.0CNY

  • Detail
  • Alfa Aesar

  • (A15232)  2'-Chloroacetophenone, 98%   

  • 2142-68-9

  • 1000g

  • 4806.0CNY

  • Detail

2142-68-9SDS

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 1-(2-chlorophenyl)ethanone

1.2 Other means of identification

Product number -
Other names 1-(2-Chlorophenyl)ethanone

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:2142-68-9 SDS

2142-68-9Synthetic route

2'-chloro-sec-phenethyl alcohol
13524-04-4

2'-chloro-sec-phenethyl alcohol

1-(2-chlorophenyl)ethanone
2142-68-9

1-(2-chlorophenyl)ethanone

Conditions
ConditionsYield
With dihydrogen peroxide; benzenesulfonic acid; potassium bromide In dichloromethane; water at 20℃; for 24h; Reagent/catalyst; Solvent;99%
With C53H46ClN3P2Ru; potassium tert-butylate; acetone at 56℃; under 750.075 Torr; for 2h; Oppenauer Oxidation;97%
With cobalt(III) acetate; sodium bromide In acetic acid at 60℃; for 1h;96%
acetyl chloride
75-36-5

acetyl chloride

chlorobenzene
108-90-7

chlorobenzene

A

1-(2-chlorophenyl)ethanone
2142-68-9

1-(2-chlorophenyl)ethanone

B

para-chloroacetophenone
99-91-2

para-chloroacetophenone

Conditions
ConditionsYield
With aluminium trichloride; 1-ethyl-3-methyl-1H-imidazol-3-ium chloride at 20℃; for 24h;A 2%
B 97%
With iron(III) sulfate In hexane at 20℃; for 0.75h; Friedel-Crafts acylation; Sonication;A 8.3%
B 73%
With iron(III) oxide In water at 20℃; for 2h; Friedel Crafts acylation; regioselective reaction;
acetic anhydride
108-24-7

acetic anhydride

chlorobenzene
108-90-7

chlorobenzene

1-(2-chlorophenyl)ethanone
2142-68-9

1-(2-chlorophenyl)ethanone

Conditions
ConditionsYield
With antimony(III) chloride In dichloromethane at 50℃; for 3h;95.3%
2-chlorophenylacetylene
873-31-4

2-chlorophenylacetylene

1-(2-chlorophenyl)ethanone
2142-68-9

1-(2-chlorophenyl)ethanone

Conditions
ConditionsYield
With C22H20AuN3O2P(1+)*CF3O3S(1-); water; silver trifluoromethanesulfonate; acetic acid at 100℃; for 10h;95%
With iron(III) chloride; water; silver(I) triflimide In 1,4-dioxane at 80℃; for 40h; regioselective reaction;94%
With water at 80℃; for 2h; Temperature; Green chemistry;87%
2-chlorostyrene
2039-87-4

2-chlorostyrene

1-(2-chlorophenyl)ethanone
2142-68-9

1-(2-chlorophenyl)ethanone

Conditions
ConditionsYield
With oxygen; palladium diacetate; trifluoroacetic acid In water; dimethyl sulfoxide at 70℃; under 760.051 Torr; for 10h; Wacker Oxidation; Sealed tube; regioselective reaction;95%
With perchloric acid; oxygen; palladium diacetate; p-benzoquinone; sodium nitrite In methanol; water at 20℃; for 5h; Wacker Oxidation; Schlenk technique; Sealed tube; Green chemistry;84%
With iron(II) chloride In ethanol at 80℃; for 4h;78%
1-(2-chlorophenyl)ethanone oxime
7147-44-6

1-(2-chlorophenyl)ethanone oxime

1-(2-chlorophenyl)ethanone
2142-68-9

1-(2-chlorophenyl)ethanone

Conditions
ConditionsYield
With dihydrogen peroxide; tripropylammonium fluorochromate (VI) In acetone at 0 - 10℃; for 6h;94%
With NTPPPODS In water; acetonitrile for 0.3h; Reflux;94%
With ferrous(II) sulfate heptahydrate; benzyl seleninic acid In ethyl acetate at 60℃; for 24h; Green chemistry;90%
1-chloro-2-(1-methoxyethyl)benzene
20001-46-1

1-chloro-2-(1-methoxyethyl)benzene

1-(2-chlorophenyl)ethanone
2142-68-9

1-(2-chlorophenyl)ethanone

Conditions
ConditionsYield
With dihydrogen peroxide; bromine In dichloromethane; water at 20℃; for 24h;92%
2-(2-chloro-phenyl)-2-methyl-[1,3]dithiane
310905-00-1

2-(2-chloro-phenyl)-2-methyl-[1,3]dithiane

1-(2-chlorophenyl)ethanone
2142-68-9

1-(2-chlorophenyl)ethanone

Conditions
ConditionsYield
With [bis(acetoxy)iodo]benzene In water; acetone at 20℃; for 0.05h; Ring cleavage;88%
1-chloro-2-ethylbenzene
89-96-3

1-chloro-2-ethylbenzene

1-(2-chlorophenyl)ethanone
2142-68-9

1-(2-chlorophenyl)ethanone

Conditions
ConditionsYield
With oxygen In water for 4h; Reflux;88%
With oxygen; silica gel; 4-aminoperbenzoic acid In dichloromethane at 20℃; for 12h;76%
acetic anhydride
108-24-7

acetic anhydride

chlorobenzene
108-90-7

chlorobenzene

A

1-(2-chlorophenyl)ethanone
2142-68-9

1-(2-chlorophenyl)ethanone

B

para-chloroacetophenone
99-91-2

para-chloroacetophenone

Conditions
ConditionsYield
With aluminum (III) chloride at 50 - 75℃; for 5.5h; Temperature;A 6%
B 88%
2-(2-chlorophenyl)-2-methyl-1,3-dioxolane
122801-34-7

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

1-(2-chlorophenyl)ethanone
2142-68-9

1-(2-chlorophenyl)ethanone

Conditions
ConditionsYield
With bismuth(III) chloride; benzyltriphenylphosphonium peroxymonosulfate In dichloromethane for 0.0833333h; microwave irradiation;85%
With aluminum oxide; potassium permanganate for 0.25h; Product distribution; Further Variations:; Reagents; reaction times;85%
With aluminium trichloride; benzyltriphenylphosphonium peroxymonosulfate at 20℃; for 0.216667h;85%
C15H15ClO
1616490-78-8

C15H15ClO

1-(2-chlorophenyl)ethanone
2142-68-9

1-(2-chlorophenyl)ethanone

Conditions
ConditionsYield
With Oxone; potassium bromide In acetonitrile at 0 - 30℃; for 24.5h; Green chemistry;85%
2-(1-(2-chlorophenyl)vinyl)-4,4,5,5-tetramethyl-1,3-dioxa-2-borolane
1239700-56-1

2-(1-(2-chlorophenyl)vinyl)-4,4,5,5-tetramethyl-1,3-dioxa-2-borolane

1-(2-chlorophenyl)ethanone
2142-68-9

1-(2-chlorophenyl)ethanone

Conditions
ConditionsYield
With triethylsilane; cyclohexa-1,4-diene; oxygen; cobalt acetylacetonate In methanol; nonane at 24℃; under 760.051 Torr; Reagent/catalyst;79%
1-(2-chlorophenyl)ethane-1-thiol

1-(2-chlorophenyl)ethane-1-thiol

1-(2-chlorophenyl)ethanone
2142-68-9

1-(2-chlorophenyl)ethanone

Conditions
ConditionsYield
With dipotassium peroxodisulfate; tetrakis(pyridine)silver(II) peroxodisulfate; oxygen In N,N-dimethyl-formamide at 23℃; under 760.051 Torr; Irradiation;79%
carbon dioxide
124-38-9

carbon dioxide

1-(2,4-dichlorophenyl)ethan-1-one
2234-16-4

1-(2,4-dichlorophenyl)ethan-1-one

A

1-(2-chlorophenyl)ethanone
2142-68-9

1-(2-chlorophenyl)ethanone

B

4-acetyl-3-chloro-benzoic acid
57542-72-0

4-acetyl-3-chloro-benzoic acid

C

2-acetyl-5-chlorobenzoic acid
115382-34-8

2-acetyl-5-chlorobenzoic acid

D

methoxybenzene
100-66-3

methoxybenzene

Conditions
ConditionsYield
With tetrabutylammomium bromide In N,N-dimethyl-formamide at 5℃; electrolysis (I=0.4 A); Yields of byproduct given;A n/a
B 78%
C n/a
D n/a
With tetrabutylammomium bromide In N,N-dimethyl-formamide at 5℃; electrolysis (I=0.4 A); Yields of byproduct given;A n/a
B n/a
C 78%
D n/a
2-chlorostyrene
2039-87-4

2-chlorostyrene

aniline
62-53-3

aniline

A

1-(2-chlorophenyl)ethanone
2142-68-9

1-(2-chlorophenyl)ethanone

B

1-chloro-2-ethylbenzene
89-96-3

1-chloro-2-ethylbenzene

C

2-chloro-β-methyl-N-phenyl-benzene ethanamine
1572529-59-9

2-chloro-β-methyl-N-phenyl-benzene ethanamine

D

N-(2-(2-chlorophenyl)propyl)aniline
103391-83-9

N-(2-(2-chlorophenyl)propyl)aniline

Conditions
ConditionsYield
With propan-1-ol; carbon monoxide; hydrogen; cetyltrimethylammonim bromide In water at 60℃; Inert atmosphere; regioselective reaction;A 5%
B 9%
C 78%
D 8%
carbon monoxide
201230-82-2

carbon monoxide

tetramethylstannane
594-27-4

tetramethylstannane

2-chlorobenzenediazonium tetrafluoroborate
1956-97-4

2-chlorobenzenediazonium tetrafluoroborate

1-(2-chlorophenyl)ethanone
2142-68-9

1-(2-chlorophenyl)ethanone

Conditions
ConditionsYield
palladium diacetate In acetonitrile under 6619.6 Torr; for 1.5h; Heating;76%
With palladium diacetate In acetonitrile for 0.5h; Ambient temperature;76%
tetramethylstannane
594-27-4

tetramethylstannane

o-chlorobenzoyl chloride
609-65-4

o-chlorobenzoyl chloride

1-(2-chlorophenyl)ethanone
2142-68-9

1-(2-chlorophenyl)ethanone

Conditions
ConditionsYield
With N,N,N,N,N,N-hexamethylphosphoric triamide; poly-γ-(diphenylphosphino)propylsiloxane palladium(0) at 65℃; for 20h;76%
acetophenone
98-86-2

acetophenone

1-(2-chlorophenyl)ethanone
2142-68-9

1-(2-chlorophenyl)ethanone

Conditions
ConditionsYield
With sodium periodate; sulfuric acid; sodium chloride In water; acetonitrile at 80℃; for 3h;75%
With N-chloro-succinimide; 2Ru(2+)*4F6P(1-)*C47H34N8*Pd(2+)*C2H6OS*2I(1-) In 1,2-dichloro-ethane at 95℃; for 16h; Sealed tube;43 %Chromat.
2-Chlorobenzeneboronic acid
3900-89-8

2-Chlorobenzeneboronic acid

acetonitrile
75-05-8

acetonitrile

1-(2-chlorophenyl)ethanone
2142-68-9

1-(2-chlorophenyl)ethanone

Conditions
ConditionsYield
With 1,10-Phenanthroline; nickel(II) bromide 2-methoxyethyl ether complex; sodium hydrogencarbonate In water at 100℃; for 5h; Autoclave;75%
1-chloro-2-(prop-1-en-2-yl)benzene
3609-45-8

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

1-(2-chlorophenyl)ethanone
2142-68-9

1-(2-chlorophenyl)ethanone

Conditions
ConditionsYield
With monoethylene glycol diethyl ether at 110℃; for 12h; Green chemistry;75%
1-(2-chloro-phenyl)-ethanone-(2,4-dinitro-phenylhydrazone)
35468-02-1

1-(2-chloro-phenyl)-ethanone-(2,4-dinitro-phenylhydrazone)

1-(2-chlorophenyl)ethanone
2142-68-9

1-(2-chlorophenyl)ethanone

Conditions
ConditionsYield
aluminum oxide; potassium permanganate at 20℃; for 0.0166667h;72%
4CH3(1-)*Zn(2+)*Li(1+)

4CH3(1-)*Zn(2+)*Li(1+)

ortho-chlorobenzoic acid
118-91-2

ortho-chlorobenzoic acid

1-(2-chlorophenyl)ethanone
2142-68-9

1-(2-chlorophenyl)ethanone

Conditions
ConditionsYield
In tetrahydrofuran; diethyl ether; hexane at -20℃; for 14h; Solvent; Schlenk technique; Inert atmosphere; chemoselective reaction;70%
2-Chlorobenzeneboronic acid
3900-89-8

2-Chlorobenzeneboronic acid

acetic anhydride
108-24-7

acetic anhydride

1-(2-chlorophenyl)ethanone
2142-68-9

1-(2-chlorophenyl)ethanone

Conditions
ConditionsYield
With 2C60H80NaO12(2+)*Cl6Pd2(2-); potassium hydrogencarbonate; triphenylphosphine In toluene at 110℃; for 3h; Inert atmosphere;59%
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)

1-(trimethylsiloxy)-1-o-chloro-phenylethene
942625-95-8

1-(trimethylsiloxy)-1-o-chloro-phenylethene

A

1-(2-chlorophenyl)ethanone
2142-68-9

1-(2-chlorophenyl)ethanone

B

C13H16ClN3O

C13H16ClN3O

Conditions
ConditionsYield
In acetonitrile for 5h; Reflux;A 29%
B 50%
2'-chloro-sec-phenethyl alcohol
13524-04-4

2'-chloro-sec-phenethyl alcohol

A

1-(2-chlorophenyl)ethanone
2142-68-9

1-(2-chlorophenyl)ethanone

Conditions
ConditionsYield
With C50H42ClN2O3Ru In chloroform at 25℃; Kinetics; Molecular sieve; Resolution of racemate; enantioselective reaction;A n/a
B 48.4%
Stage #1: 2'-chloro-sec-phenethyl alcohol 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
With sulfuric acid; MnII((1R,2R)-N,N'-dimethyl-N,N'-bis((R)-(3,5-di-tert-butylphenyl)-2-pyridinylmethyl)cyclohexane-1,2-diamine)(OTf)2; dihydrogen peroxide In water; acetonitrile at 0℃; for 1h; Inert atmosphere; Schlenk technique;A n/a
B n/a
2-(2-chlorophenyl)propane-1,2-diol

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

1-(2-chlorophenyl)ethanone
2142-68-9

1-(2-chlorophenyl)ethanone

Conditions
ConditionsYield
With oxygen; sodium carbonate In water at 20℃; for 5h; Irradiation; Green chemistry;47%
o-chloro-α-phenoxyacetophenone
135774-33-3

o-chloro-α-phenoxyacetophenone

1-(2-chlorophenyl)ethanone
2142-68-9

1-(2-chlorophenyl)ethanone

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 35h; Rate constant; Irradiation;34.6%
2-Chlorobenzoyl acetonitrile
40018-25-5

2-Chlorobenzoyl acetonitrile

A

1-(2-chlorophenyl)ethanone
2142-68-9

1-(2-chlorophenyl)ethanone

B

3-(2-chloro-phenyl)-3-oxo-propionamide

3-(2-chloro-phenyl)-3-oxo-propionamide

Conditions
ConditionsYield
With Rhodococcus rhodochrous IFO 15564A n/a
B 27%
1-(2-chlorophenyl)ethanone
2142-68-9

1-(2-chlorophenyl)ethanone

Conditions
ConditionsYield
With RuBr2[(S,S)-2,4-bis(diphenylphosphino)pentane](2-aminomethyl-3,5-dimethylpyridine); potassium tert-butylate; hydrogen In ethanol at 40℃; under 7600.51 Torr; for 19h; Catalytic behavior; Solvent; Reagent/catalyst; Inert atmosphere; Autoclave;100%
With n-hexan-2-ol In hexane; water at 30℃; for 24h; immobilized Geotrichum candidum;99%
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%
1-(2-chlorophenyl)ethanone
2142-68-9

1-(2-chlorophenyl)ethanone

Conditions
ConditionsYield
With dimethylsulfide borane complex; 4-chloro-2-(((1S,2R)-1-hydroxy-1-phenylpropan-2-ylamino)methyl)phenol In tetrahydrofuran for 2h; Inert atmosphere; Reflux; optical yield given as %ee; enantioselective reaction;100%
With bis(1,5-cyclooctadiene)diiridium(I) dichloride; C45H58NP; potassium tert-butylate; hydrogen In propan-1-ol at 25 - 30℃; under 4560.31 Torr; for 0.166667h; Autoclave; optical yield given as %ee; enantioselective reaction;100%
With Ir-SpiroPAP; potassium tert-butylate In ethanol at 40℃; for 10h; Inert atmosphere;99%
1-(2-chlorophenyl)ethanone
2142-68-9

1-(2-chlorophenyl)ethanone

oxalic acid diethyl ester
95-92-1

oxalic acid diethyl ester

Lithium; (Z)-3-(2-chloro-phenyl)-1-ethoxycarbonyl-3-oxo-propen-1-olate

Lithium; (Z)-3-(2-chloro-phenyl)-1-ethoxycarbonyl-3-oxo-propen-1-olate

Conditions
ConditionsYield
With lithium hexamethyldisilazane In diethyl ether at -78 - 20℃;100%
1-(2-chlorophenyl)ethanone
2142-68-9

1-(2-chlorophenyl)ethanone

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

(E)-1-(2-chlorophenyl)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;93%
With hydroxylamine hydrochloride; sodium hydroxide In ethanol; water at 0 - 20℃; for 24h; pH=9;93%
1-(2-chlorophenyl)ethanone
2142-68-9

1-(2-chlorophenyl)ethanone

2'-chloro-sec-phenethyl alcohol
13524-04-4

2'-chloro-sec-phenethyl alcohol

Conditions
ConditionsYield
With [biphenyl-2-O-Al(OiPr)-N(SO2C8H17)-2'] In dichloromethane; isopropyl alcohol at 25℃; for 1h; Meerwein-Ponndorf-Verley reduction;99%
With [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; sodium formate; ephedrine hydrochloride at 20℃;99%
With sodium tetrahydroborate In tetrahydrofuran for 2h; Heating; ultrasound irradiation;99%
1-(2-chlorophenyl)ethanone
2142-68-9

1-(2-chlorophenyl)ethanone

2-chlorophenacyl bromide
5000-66-8

2-chlorophenacyl bromide

Conditions
ConditionsYield
With bromine In water at 20℃; for 0.75h; Large scale;99%
With 5,5-dibromohydantoin; tetrabutylammomium bromide In ethanol at 65℃; for 3h; Temperature; Reagent/catalyst; Solvent;92.5%
With copper(II) nitrate trihydrate; hydrogen bromide; oxygen at 70℃; for 3.5h; Green chemistry;86%
trimethylsilyl cyanide
7677-24-9

trimethylsilyl cyanide

1-(2-chlorophenyl)ethanone
2142-68-9

1-(2-chlorophenyl)ethanone

2-(2-chlorophenyl)-2-(trimethylsilyloxy)propanenitrile

2-(2-chlorophenyl)-2-(trimethylsilyloxy)propanenitrile

Conditions
ConditionsYield
With rasta resin-PPh3BnCl In chloroform at 50℃; for 10h; Inert atmosphere;99%
With C40H52LiN8O2Sm at 20℃; for 3h; Inert atmosphere; Schlenk technique;96%
Fe(Cp)2PF6 at 20℃; for 0.166667h;91%
1-(2-chlorophenyl)ethanone
2142-68-9

1-(2-chlorophenyl)ethanone

ethyl acetoacetate
141-97-9

ethyl acetoacetate

malononitrile
109-77-3

malononitrile

6-amino-4-(2-chlorophenyl)-2,4-dihydro-3,4-dimethylpyrano[2,3-c]pyrazole-5-carbonitrile
1235990-54-1

6-amino-4-(2-chlorophenyl)-2,4-dihydro-3,4-dimethylpyrano[2,3-c]pyrazole-5-carbonitrile

Conditions
ConditionsYield
With hydrazine hydrate; heptakis(6-amino-6-deoxy)-β-cyclodextrin at 20℃; for 0.0166667h; Neat (no solvent);99%
1-(2-chlorophenyl)ethanone
2142-68-9

1-(2-chlorophenyl)ethanone

2-propynyl chloride
624-65-7

2-propynyl chloride

C11H11ClO
1340170-80-0

C11H11ClO

Conditions
ConditionsYield
With 2,4,6-trimethyl-pyridine; bis(cyclopentadienyl)titanium dichloride; manganese; chloro-trimethyl-silane In tetrahydrofuran at 20℃; for 7h; Barbier Coupling Reaction; Inert atmosphere; chemoselective reaction;99%
1-(2-chlorophenyl)ethanone
2142-68-9

1-(2-chlorophenyl)ethanone

diphenylsilane
775-12-2

diphenylsilane

(1-(2-chlorophenyl)ethoxy)diphenylsilane

(1-(2-chlorophenyl)ethoxy)diphenylsilane

Conditions
ConditionsYield
With C84H110N10Zn2 In neat (no solvent) at 20℃; for 12h; Sealed tube; Inert atmosphere; Schlenk technique; Glovebox;99%
With (1,3-dibutyldibenzo[a,c]phenazino[11,12-d]imidazolin-2-ylidene)iridium(1,5-cyclooctadiene) chloride In benzene-d6 for 10h;88 %Spectr.
1-(2-chlorophenyl)ethanone
2142-68-9

1-(2-chlorophenyl)ethanone

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
25015-63-8

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane

2-(1-(2-chlorophenyl)ethoxy)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

2-(1-(2-chlorophenyl)ethoxy)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Conditions
ConditionsYield
at 140℃; for 9h;99%
With C84H110N10Zn2 In neat (no solvent) at 20℃; for 6h; Sealed tube; Inert atmosphere; Schlenk technique; Glovebox;99%
With C24H34N5PSeTi In neat (no solvent) at 60℃; for 4h; Glovebox; Schlenk technique; chemoselective reaction;93%
1-(2-chlorophenyl)ethanone
2142-68-9

1-(2-chlorophenyl)ethanone

benzaldehyde
100-52-7

benzaldehyde

1-(2-chloro-phenyl)-3-phenyl-2-propen-1-one
144017-77-6, 20426-47-5

1-(2-chloro-phenyl)-3-phenyl-2-propen-1-one

Conditions
ConditionsYield
With potassium hydroxide In ethanol; water at 25℃; Claisen-Schmidt Condensation;98.7%
With sodium hydroxide In ethanol at 20℃;81%
With sodium hydroxide In ethanol; water at 79.84℃; Kinetics; Temperature; Claisen-Schmidt condensation; Microwave irradiation;
1-(2-chlorophenyl)ethanone
2142-68-9

1-(2-chlorophenyl)ethanone

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 tetrabutylammomium bromide; potassium carbonate; Pd(NH3)2Cl2 In water at 140℃; for 18h; Suzuki cross-coupling reaction;98%
With potassium carbonate; MgLa mixed oxide; palladium In ethanol at 80℃; for 2h; Suzuki-Miyaura cross-coupling;97%
With 1,4-diaza-bicyclo[2.2.2]octane; potassium phosphate tribasic trihydrate; tetrabutylammomium bromide; palladium diacetate In water; N,N-dimethyl-formamide at 50℃; for 24h; Suzuki coupling;96%
1-(2-chlorophenyl)ethanone
2142-68-9

1-(2-chlorophenyl)ethanone

cyclohexylmagnesiumchloride
931-51-1

cyclohexylmagnesiumchloride

1-(2-cyclohexylphenyl)ethan-1-one
817556-88-0

1-(2-cyclohexylphenyl)ethan-1-one

Conditions
ConditionsYield
Stage #1: cyclohexylmagnesiumchloride With lithium chloride; manganese(ll) chloride In tetrahydrofuran at -10℃;
Stage #2: 1-(2-chlorophenyl)ethanone In tetrahydrofuran at 0 - 5℃; for 0.5h;
98%
1-(2-chlorophenyl)ethanone
2142-68-9

1-(2-chlorophenyl)ethanone

2-chloro-1-(2-chlorophenyl)ethanone
4209-25-0

2-chloro-1-(2-chlorophenyl)ethanone

Conditions
ConditionsYield
With sulfuryl dichloride In methanol; hexane at 0℃; for 8h;98%
With potassium peroxymonosulfate; ammonium chloride In methanol for 10h; Reflux;84 %Chromat.
Stage #1: 1-(2-chlorophenyl)ethanone With N-chloro-succinimide In acetonitrile
Stage #2: With toluene-4-sulfonic acid In acetonitrile at 60℃; for 6h;
With N-chloro-succinimide; toluene-4-sulfonic acid
1-(2-chlorophenyl)ethanone
2142-68-9

1-(2-chlorophenyl)ethanone

4-(2-chlorophenyl)-4-hydroxybut-3-en-2-one

4-(2-chlorophenyl)-4-hydroxybut-3-en-2-one

Conditions
ConditionsYield
With sodium hydride In ethyl acetate; mineral oil at 0 - 20℃; for 12h;98%
1-(2-chlorophenyl)ethanone
2142-68-9

1-(2-chlorophenyl)ethanone

4-methoxy-benzaldehyde
123-11-5

4-methoxy-benzaldehyde

3-(4-methoxyphenyl)-1-(2-chlorophenyl)-2-propen-1-one
92873-89-7

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

Conditions
ConditionsYield
With methanol; sodium In methanol at 20℃; Aldol Condensation;97.8%
In ethanol at 20℃; Claisen-Schmidt Condensation;
1-(2-chlorophenyl)ethanone
2142-68-9

1-(2-chlorophenyl)ethanone

(S)-2-chloro-1-phenylethanol
70111-05-6

(S)-2-chloro-1-phenylethanol

Conditions
ConditionsYield
With borane-THF; oxazaborolidine (3) In tetrahydrofuran at 20 - 30℃; for 0.166667h;97.1%
1-(2-chlorophenyl)ethanone
2142-68-9

1-(2-chlorophenyl)ethanone

ethylmagnesium bromide
925-90-6

ethylmagnesium bromide

1-(2-ethylphenyl)ethanone
2142-64-5

1-(2-ethylphenyl)ethanone

Conditions
ConditionsYield
Stage #1: ethylmagnesium bromide With lithium chloride; manganese(ll) chloride In tetrahydrofuran at -50℃;
Stage #2: 1-(2-chlorophenyl)ethanone In tetrahydrofuran at -50℃; for 1h;
97%
With lithium chloride; manganese(ll) chloride In tetrahydrofuran at -50℃; for 4.25h;80%
1-(2-chlorophenyl)ethanone
2142-68-9

1-(2-chlorophenyl)ethanone

butyl magnesium bromide
693-04-9

butyl magnesium bromide

1-(2-butylphenyl)ethan-1-one
58632-85-2

1-(2-butylphenyl)ethan-1-one

Conditions
ConditionsYield
Stage #1: butyl magnesium bromide With lithium chloride; manganese(ll) chloride In tetrahydrofuran at -20℃;
Stage #2: 1-(2-chlorophenyl)ethanone In tetrahydrofuran at 0 - 5℃; for 0.5h;
97%
triethylsilane
617-86-7

triethylsilane

1-(2-chlorophenyl)ethanone
2142-68-9

1-(2-chlorophenyl)ethanone

[1-(2-chlorophenyl)ethoxy](triethyl)silane

[1-(2-chlorophenyl)ethoxy](triethyl)silane

Conditions
ConditionsYield
With (N,N'-dicyclohexyl-2H-imidazol-2-ylidene)CuCl; sodium t-butanolate In toluene at 80℃; for 1.5h;97%
With copper; 1,3-bis(mesityl)imidazolium chloride; sodium t-butanolate In toluene at 80℃; for 2h; Schlenk technique; Inert atmosphere;97%
With sodium t-butanolate; [Cu(N,N'-bis(cyclohexyl)imidazol-2-ylidene)2]BF4 In tetrahydrofuran at 55℃; for 2.5h;92%
With (1,3-dimesitylimidazolidin-2-yl)copper(I) chloride; sodium t-butanolate In tetrahydrofuran at 80℃; for 1h;91%
With (1,3-dimesityl-5-methyl-6-oxo-6H-pyrimidin-2-ylidene-4-olate)-copper(I) lithium(THF)2; sodium t-butanolate In tetrahydrofuran at 65℃; for 2h; Schlenk technique; Inert atmosphere;22%
1-(2-chlorophenyl)ethanone
2142-68-9

1-(2-chlorophenyl)ethanone

tris(allyl)aluminum
18854-66-5

tris(allyl)aluminum

2-(2-chlorophenyl)-4-penten-2-ol

2-(2-chlorophenyl)-4-penten-2-ol

Conditions
ConditionsYield
In diethyl ether at 20℃; for 0.5h;97%
1-(2-chlorophenyl)ethanone
2142-68-9

1-(2-chlorophenyl)ethanone

rel-(R)-1-(o-chlorophenyl)ethanol

rel-(R)-1-(o-chlorophenyl)ethanol

Conditions
ConditionsYield
With bis(1,5-cyclooctadiene)diiridium(I) dichloride; (R)-N-(3-methylpyridine-2-methyl)-7-bis-(3,5-di-tert-butylphenyl)phosphino-7′-amino-1,1′-spirodihydroindane; potassium tert-butylate; hydrogen In ethanol at 20℃; under 6080.41 - 7600.51 Torr; for 0.583333h; Inert atmosphere; Sealed tube;97%
With bis(1,5-cyclooctadiene)diiridium(I) dichloride; (R)-N-(3-methylpyridine-2-methyl)-7-bis-(3,5-di-tert-butylphenyl)phosphino-7′-amino-1,1′-spirodihydroindane; potassium tert-butylate; hydrogen In ethanol at 20℃; under 6080.41 - 7600.51 Torr; for 0.583333h; Autoclave;97%
With (S)-N-(2,6-diisopropyl-phenyl)pyrrolidine-2-carboxamide; [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; sodium formate; sodium dodecyl-sulfate In water at 40℃; for 4h; Temperature; enantioselective reaction;92%
1-(2-chlorophenyl)ethanone
2142-68-9

1-(2-chlorophenyl)ethanone

4-Phenyl-3-thiosemicarbazide
5351-69-9

4-Phenyl-3-thiosemicarbazide

ClC6H4C(CH3)NNHC(S)NHC6H5

ClC6H4C(CH3)NNHC(S)NHC6H5

Conditions
ConditionsYield
With hydrogenchloride In water at 20℃; for 4h;97%
1-(2-chlorophenyl)ethanone
2142-68-9

1-(2-chlorophenyl)ethanone

tert-butylferrocenylmethylsilane
1204405-72-0

tert-butylferrocenylmethylsilane

1-((1-(o-chlorophenyl)ethoxy)(methyl)tert-butylsilyl)ferrocene
1263321-62-5, 1263321-69-2

1-((1-(o-chlorophenyl)ethoxy)(methyl)tert-butylsilyl)ferrocene

Conditions
ConditionsYield
With ((C6H5)3C)(B(C6F5)4) In dichloromethane Ar, Schlenk technique; dry CH2Cl2 added to Ph3CB(C6F5)4 (0.010 mmol), cooled to -60°C, Fe complex (0.040 mmol) added, stirred for 10 min,soln. of ketone (0.20 mmol) and Fe complex (0.20 mmol) added, mixt. kep t at -60°C for 2.5 h; cold (-60°C) hexane added, soln. filtered through Celite, filtrate evapd. under vac., flash chromy. (silica gel, cyclohexane);97%
1-(2-chlorophenyl)ethanone
2142-68-9

1-(2-chlorophenyl)ethanone

m-xylene
108-38-3

m-xylene

1-[1-(2-chlorophenyl)ethyl]-2,4-dimethylbenzene

1-[1-(2-chlorophenyl)ethyl]-2,4-dimethylbenzene

Conditions
ConditionsYield
With triethylsilane; iron(III) chloride; chloro-trimethyl-silane at 20 - 50℃; Catalytic behavior; Friedel-Crafts Alkylation; regioselective reaction;97%
1-(2-chlorophenyl)ethanone
2142-68-9

1-(2-chlorophenyl)ethanone

ethylene glycol
107-21-1

ethylene glycol

2-(2-chlorophenyl)-2-methyl-1,3-dioxolane
122801-34-7

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

Conditions
ConditionsYield
With toluene-4-sulfonic acid In benzene for 12h; Heating;96%
With toluene-4-sulfonic acid In toluene for 48h; Dean-Stark; Reflux;91%
1-(2-chlorophenyl)ethanone
2142-68-9

1-(2-chlorophenyl)ethanone

n-octylmagnesium chloride
38841-98-4

n-octylmagnesium chloride

1-(2-octyl-phenyl)-ethanone

1-(2-octyl-phenyl)-ethanone

Conditions
ConditionsYield
Stage #1: n-octylmagnesium chloride With lithium chloride; manganese(ll) chloride In tetrahydrofuran at -10℃;
Stage #2: 1-(2-chlorophenyl)ethanone In tetrahydrofuran at 0 - 5℃; for 0.5h;
96%

2142-68-9Relevant articles and documents

-

Forbes,Mueller

, p. 488,498 (1957)

-

V2O5 anchored RuO2: An efficient nanocatalyst for aerial oxidation of alcohols

Ganesh Babu,Krishnamoorthi,Thiruneelakandan,Karvembu

, p. 1245 - 1252 (2014)

RuO2/V2O5 nanocatalyst has been prepared from Ru(acac)3 and V2O5 by a simple dry synthesis for the first time. The formation of RuO2/V 2O5 nanocatalyst was confirmed by XRD and FT-IR analyses. Morphology and size of the nanocatalyst were found using SEM and TEM respectively. SEM-EDS analysis was carried out to know the weight percentage of Ru in the catalyst. Thermal stability of the catalyst was found using TG/DTA analysis. Further, RuO2/V2O5 was found to be an efficient catalyst for the aerial oxidation of alcohols to their corresponding carbonyl compounds. Moreover, very low Ru content (0.36 mol%) was exploited for this conversion, nevertheless very high turnover number was observed. The use of recyclable nanocatalyst and atmospheric oxygen as oxidant made the system interesting from the green chemistry point of view.

An efficient and scalable room temperature aerobic alcohol oxidation catalyzed by iron chloride hexahydrate/mesoporous silica supported TEMPO

Wang, Lianyue,Li, Jun,Zhao, Xiaoping,Lv, Ying,Zhang, Hengyun,Gao, Shuang

, p. 6041 - 6045 (2013)

An efficient room temperature catalytic system FeCl3· 6H2O/SBA-15-TEMPO/NaNO2 for the oxidation of alcohols with dioxygen or air as terminal oxidant has been developed. Various alcohols were oxidized at a low catalyst loading (0.1-1 mol %) to the corresponding carbonyl compounds in good to excellent yields. For the oxidation of benzyl alcohol, the excellent turn-over frequency (TOF) of 81.4 h-1 was achieved (turn-over number (TON) up to 9770). The catalyst SBA-15-TEMPO can be reused for 10 reaction runs without significant loss of catalytic activity. In addition, the two components FeCl3·6H2O and SBA-15-TEMPO can also be reused for at least four reaction runs without appreciable loss of catalytic activity. In the case of large-scale experiment for the oxidation of benzyl alcohol, the desired product benzaldehyde was obtained in 94.5% yield.

-

Rogers

, p. 2784,2786 (1956)

-

Highly ordered mesoporous hybrid silica functionalized with ionic liquid framework supported copper and its application in the oxidation of alcohols

Rajabi, Fatemeh,Bahrami, Nazli,Vessally, Esmail,Luque, Rafael

, (2021/10/27)

A highly ordered organic-inorganic hybrid nanomaterial containing copper N-heterocyclic carbene complex (Cu-NHC@Pyrm-OMS) was synthesized and characterized using various techniques including FTIR, MAS NMR, XRD, TGA, SEM, and TEM. Cu-NHC@Pyrm-OMS nanomaterial is highly efficient heterogeneous system towards the selective oxidation of primary and secondary alcohols to corresponding aldehydes and ketones under mild conditions. Moreover, the supported copper nanocatalyst exhibited outstanding stability and could be reused at least ten times, remaining almost unchanged from initial activity. This work has focused on sustainable and green chemistry that use recoverable nanocatalyst, clean oxidant and aqueous media.

Ruthenium(II) Complexes Bearing Schiff Base Ligands for Efficient Acceptorless Dehydrogenation of Secondary Alcohols?

Dong, Qing,Feng, Qi,Han, Zhangang,Hao, Zhiqiang,Lin, Jin,Liu, Kang,Lu, Guo-Liang,Ma, Dongzhu

, p. 121 - 128 (2020/12/25)

Four ruthenium(II) complexes 1—4 [RN=CH-(2,4-(tBu)2C6H2O)]RuH(PPh3)2(CO) (R = C6H5, 1; R = 4-MeC6H4, 2; R = 4-ClC6H4, 3; R = 4-BrC6H4, 4) bearing Schiff base ligands were prepared by treating RuHClCO(PPh3)3 with RN=CH-(2,4-(tBu)2C6H2OH (L1—L4) in the presence of triethylamine. Their structures were fully characterized by elemental analysis, IR, NMR spectroscopy and X-ray crystallography. These Ru(II) complexes exhibit high catalytic performance and good functional-group compatibility in the acceptorless dehydrogenation of secondary alcohols, affording the corresponding ketones in 82%—94% yields.

Iron-catalyzed domino decarboxylation-oxidation of α,β-unsaturated carboxylic acids enabled aldehyde C-H methylation

Gong, Pei-Xue,Xu, Fangning,Cheng, Lu,Gong, Xu,Zhang, Jie,Gu, Wei-Jin,Han, Wei

supporting information, p. 5905 - 5908 (2021/06/18)

A practical and general iron-catalyzed domino decarboxylation-oxidation of α,β-unsaturated carboxylic acids enabling aldehyde C-H methylation for the synthesis of methyl ketones has been developed. This mild, operationally simple method uses ambient air as the sole oxidant and tolerates sensitive functional groups for the late-stage functionalization of complex natural-product-derived and polyfunctionalized molecules.

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