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495-40-9

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495-40-9 Usage

Description

Butyrophenone is a chemical compound with the formula C10H12O. Butyrophenone has been used to study the relationship between the electrolyte counter-ion concentration and the critical micelle concentration for several surfactants. It has been used to generate PhCO+ ions by 70 eV electron ionization. Some of its derivatives (called commonly butyrophenones) are used to treat various psychiatric disorders such as schizophrenia, as well as acting as antiemetics. They can interfere with neurotransmitter functions, usually blocking dopamine receptors, and induce behavioral, endocrine, motor-kinetic effects. Examples of butyrophenones include: Haloperidol, the most widely used classical antipsychotic drug in this class; Benperidol, the most potent commonly used antipsychotic ( 200 times more potent than chlorpromazine).

References

1. https://en.wikipedia.org/wiki/Butyrophenone 2. http://www.rightdiagnosis.com/medical/butyrophenone.htm 3. http://www.sigmaaldrich.com/catalog/product/aldrich/124338?lang=en®ion=CA

Chemical Properties

colourless to yellow liquid

Uses

Different sources of media describe the Uses of 495-40-9 differently. You can refer to the following data:
1. Butyrophenone is used as intermediates of Liquid Crystals
2. Intermediates of Liquid Crystals

Synthesis Reference(s)

The Journal of Organic Chemistry, 61, p. 376, 1996 DOI: 10.1021/JO951500RTetrahedron Letters, 30, p. 6357, 1989 DOI: 10.1016/S0040-4039(01)93893-6

Biochem/physiol Actions

Butyrophenones constitutes neuroleptic drugs and interacts with the opiate receptor by inhibiting the stereospecific binding of 3H-naloxone.

Check Digit Verification of cas no

The CAS Registry Mumber 495-40-9 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 4,9 and 5 respectively; the second part has 2 digits, 4 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 495-40:
(5*4)+(4*9)+(3*5)+(2*4)+(1*0)=79
79 % 10 = 9
So 495-40-9 is a valid CAS Registry Number.
InChI:InChI=1/C10H12O/c1-2-6-10(11)9-7-4-3-5-8-9/h3-5,7-8H,2,6H2,1H3

495-40-9 Well-known Company Product Price

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  • Alfa Aesar

  • (A11345)  Butyrophenone, 99%   

  • 495-40-9

  • 25g

  • 219.0CNY

  • Detail
  • Alfa Aesar

  • (A11345)  Butyrophenone, 99%   

  • 495-40-9

  • 50g

  • 358.0CNY

  • Detail
  • Alfa Aesar

  • (A11345)  Butyrophenone, 99%   

  • 495-40-9

  • 250g

  • 1571.0CNY

  • Detail

495-40-9SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name Butyrophenone

1.2 Other means of identification

Product number -
Other names Phenyl Propyl Ketone

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Food additives -> Flavoring Agents
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:495-40-9 SDS

495-40-9Synthetic route

1-Phenyl-1-butanol
614-14-2

1-Phenyl-1-butanol

butyrophenone
495-40-9

butyrophenone

Conditions
ConditionsYield
With dinitrogen monoxide; dioxo(tetramesitylporphyrinato)ruthenium(VI) In 1,2-dichloro-ethane at 150℃; under 7600 Torr; for 7.5h;100%
With dinitrogen monoxide; dioxo(tetramesitylporphyrinato)ruthenium(VI) In 1,2-dichloro-ethane at 150℃; under 7500.6 Torr; for 7.5h;100%
With silica-supported Jones reagent In dichloromethane for 0.00269444h;100%
(E)-1-phenyl-2-buten-1-one
35660-91-4, 35845-66-0, 495-41-0

(E)-1-phenyl-2-buten-1-one

butyrophenone
495-40-9

butyrophenone

Conditions
ConditionsYield
With indium; acetic acid In tetrahydrofuran Heating;100%
With indium(III) chloride; Bu3SnH4 In methanol at -78 - 20℃; for 1h;97%
With samarium diiodide; 2,4-dichlorophenoxyacetic acid dimethylamine; tert-butyl alcohol In tetrahydrofuran93%
1-phenyl-1-butanone 2-naphthylethanone p-toluenesulfonylhydrazone
41780-81-8

1-phenyl-1-butanone 2-naphthylethanone p-toluenesulfonylhydrazone

butyrophenone
495-40-9

butyrophenone

Conditions
ConditionsYield
With copper(II) sulfate In tetrahydrofuran; methanol; water for 3h; Heating;100%
Bis-1-phenyl-n-butyliden-diazin
17745-98-1

Bis-1-phenyl-n-butyliden-diazin

butyrophenone
495-40-9

butyrophenone

Conditions
ConditionsYield
With 2-phenyl-1,2-benzoisoselenazol-3(2H)-one; dihydrogen peroxide In methanol; water at 65℃; for 1.5h;100%
With ammonium cerium(IV) nitrate In water; acetonitrile at 20℃; for 16h; Oxidation;96%
propyl bromide
106-94-5

propyl bromide

benzonitrile
100-47-0

benzonitrile

butyrophenone
495-40-9

butyrophenone

Conditions
ConditionsYield
Stage #1: propyl bromide With iodine; magnesium In diethyl ether
Stage #2: benzonitrile In diethyl ether for 6h; Heating;
100%
4-iodobutyrophenone
65488-05-3

4-iodobutyrophenone

butyrophenone
495-40-9

butyrophenone

Conditions
ConditionsYield
With tri(2-furyl)germane; triethyl borane In tetrahydrofuran at 20℃; for 2h; Reduction;99%
With tri(2-furyl)germane; triethyl borane In tetrahydrofuran; hexane at 20℃; for 2h;99%
With gallium(III) trichloride; triethyl borane; sodium bis(2-methoxyethoxy)aluminium dihydride; oxygen In tetrahydrofuran; hexane; toluene at 0℃; for 9h;80%
With (2-((dimethylamino)methyl)phenyl)dimethyltin In tetrahydrofuran at 20℃; for 12h;98 % Chromat.
In N,N,N,N,N,N-hexamethylphosphoric triamide Rate constant; Mechanism; Ambient temperature; Irradiation; transient absorption spectra at various times after irradiation; other solvents;
2-cyano-butyric acid ethyl ester
1619-58-5

2-cyano-butyric acid ethyl ester

phenylboronic acid
98-80-6

phenylboronic acid

butyrophenone
495-40-9

butyrophenone

Conditions
ConditionsYield
With trifluorormethanesulfonic acid; water; palladium diacetate; 2-(3,5-dimethyl-1H-pyrazol-1-yl)pyridine at 60℃; for 5h;99%
1-phenylbut-2-en-1-one
495-41-0

1-phenylbut-2-en-1-one

butyrophenone
495-40-9

butyrophenone

Conditions
ConditionsYield
With tri-n-butyl-tin hydride In benzene at 20 - 80℃; for 3h; Inert atmosphere;98%
With formic acid; [Pd(C,N-2-chloro-7-(mesitylimidazolylidenylmethyl)naphthyridine)(η3-allyl)](BF4); triethylamine In isopropyl alcohol for 16h; Inert atmosphere; Reflux;96%
With Li(1+)*HSe(1-); water In tetrahydrofuran at 50℃; for 5h;95%
2-bromo-1-phenylbutan-1-one
877-35-0

2-bromo-1-phenylbutan-1-one

butyrophenone
495-40-9

butyrophenone

Conditions
ConditionsYield
With diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate; acetic acid for 1.3h; Irradiation; Inert atmosphere;98%
With N,N,N,N,-tetramethylethylenediamine; diisobutylaluminium hydride; tin(ll) chloride In tetrahydrofuran; toluene at -78℃; for 0.166667h;90%
With indium; water for 7.5h; ultrasound;85%
With hydrogen selenide; triethylamine In methanol at -20℃; for 3h; Yield given;
1,2-diphenylcyclopentene ozonide
73258-08-9

1,2-diphenylcyclopentene ozonide

A

4-hydroxy-1-phenyl-butan-1-one
39755-03-8

4-hydroxy-1-phenyl-butan-1-one

B

butyrophenone
495-40-9

butyrophenone

C

3,4-dihydronaphthalene-1(2H)-one
529-34-0

3,4-dihydronaphthalene-1(2H)-one

D

benzoic acid
65-85-0

benzoic acid

Conditions
ConditionsYield
With iron(II) sulfate In tetrahydrofuran; water at 20℃; for 16h; Product distribution; Mechanism; other ozonides; 18O-tracer exp. with ethereal oxygen labeled; reduction also in presence of 18O-labeled H2O or D2O;A 7%
B 33%
C 19%
D 98%
With iron(II) sulfate In tetrahydrofuran; water at 20℃; for 16h;A 7%
B 33%
C 19%
D 98%
Conditions
ConditionsYield
With [RuCl(η5-(3-phenyl)indenyl)(PPh3)2] In toluene at 20℃; for 1h;97%
Multi-step reaction with 3 steps
1: n-butyllithium / tetrahydrofuran / 0 °C / Inert atmosphere
2: [RhCl2(p-cymene)]2; phosphorous acid trimethyl ester / tetrahydrofuran / 2 h / 67 °C / Inert atmosphere
3: water / tetrahydrofuran / Inert atmosphere
View Scheme
butyrophenone phenylhydrazone
54431-10-6

butyrophenone phenylhydrazone

butyrophenone
495-40-9

butyrophenone

Conditions
ConditionsYield
With copper(II) sulfate In tetrahydrofuran; methanol; water for 2h; Heating;95%
1-phenyl-1-butyne
622-76-4

1-phenyl-1-butyne

butyrophenone
495-40-9

butyrophenone

Conditions
ConditionsYield
With water In neat (no solvent) at 100℃; for 22h; Green chemistry; regioselective reaction;93%
With iron(III) chloride; water; silver(I) triflimide In 1,4-dioxane at 95℃; for 60h; regioselective reaction;92%
With trifluorormethanesulfonic acid; water In 2,2,2-trifluoroethanol at 25℃; for 45h; Sealed tube; regioselective reaction;92%
(2E)-1-phenylbut-2-en-1-ol
52755-39-2

(2E)-1-phenylbut-2-en-1-ol

butyrophenone
495-40-9

butyrophenone

Conditions
ConditionsYield
With chloro(1,5-cyclooctadiene)rhodium(I) dimer; cesium acetate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In tetrahydrofuran at 70℃; for 15h; Glovebox; Sealed tube; Inert atmosphere;93%
With iron pentacarbonyl In pentane for 5h; UV-irradiation;64%
With Cp*RuCl(Ph2P(CH2)2NH2-κ2-P,N) In toluene at 30℃; for 1h;99 % Spectr.
1-Phenyl-3-buten-1-ol
80735-94-0

1-Phenyl-3-buten-1-ol

butyrophenone
495-40-9

butyrophenone

Conditions
ConditionsYield
With C30H29BrMnNO2P2; potassium tert-butylate In toluene at 120℃; for 1h;93%
With Fe(II)(bis(2-(diisopropylphosphino)ethyl)amine)(CO)(H)(Cl); potassium tert-butylate In toluene at 80℃; for 1h; Inert atmosphere;88%
With chloro(1,5-cyclooctadiene)rhodium(I) dimer; cesium acetate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In tetrahydrofuran at 70℃; for 15h; Glovebox; Sealed tube; Inert atmosphere;88%
butyrophenone
495-40-9

butyrophenone

Conditions
ConditionsYield
With ferrous(II) sulfate heptahydrate; benzyl seleninic acid In ethyl acetate at 60℃; for 24h; Green chemistry;93%
With dibenzyl diselenide; dihydrogen peroxide In acetonitrile at 60℃; for 24h;67%
With wool supported manganese dioxide nanoparticles at 20℃; for 7h;94 %Chromat.
With Manganese dioxide nanostructures coated on natural silk at 20℃; for 0.0833333h;
1-butylbenzene
104-51-8

1-butylbenzene

butyrophenone
495-40-9

butyrophenone

Conditions
ConditionsYield
With potassium permanganate; Rexyn 101 H ion exchange resin In dichloromethane for 5.45h; Heating;92%
With manganese(IV) oxide; potassium permanganate In dichloromethane at 20℃; for 27h;92%
With tert.-butylhydroperoxide In water at 20℃; for 48h; Sealed tube;92%
2-iodo-1-phenylbutan-1-one
108350-39-6

2-iodo-1-phenylbutan-1-one

butyrophenone
495-40-9

butyrophenone

Conditions
ConditionsYield
With indium; water for 3.5h; ultrasound;91%
iodobenzene
591-50-4

iodobenzene

butyraldehyde
123-72-8

butyraldehyde

butyrophenone
495-40-9

butyrophenone

Conditions
ConditionsYield
With caesium carbonate In 1,4-dioxane for 8h; Reflux;91%
With C20H19Cl2PPdS; caesium carbonate In 1,4-dioxane; dichloromethane at 100℃; for 16h; Reagent/catalyst;59%
With dibromo[1,2-bis(diphenylphosphino)ethane]nickel(II); zinc In tetrahydrofuran at 110℃; for 36h;33%
(RS)-2-phenylpentanoic acid
7782-21-0

(RS)-2-phenylpentanoic acid

butyrophenone
495-40-9

butyrophenone

Conditions
ConditionsYield
With mercury(II) fluoride; oxygen In acetonitrile at 25℃; for 24h; Irradiation;91%
propyl cyanide
109-74-0

propyl cyanide

phenylboronic acid
98-80-6

phenylboronic acid

butyrophenone
495-40-9

butyrophenone

Conditions
ConditionsYield
With trifluorormethanesulfonic acid; palladium diacetate; 2-(3,5-dimethyl-1H-pyrazol-1-yl)pyridine In water at 60℃; for 4.5h;91%
With 1,10-Phenanthroline; nickel(II) bromide 2-methoxyethyl ether complex; sodium hydrogencarbonate In water at 100℃; for 5h; Autoclave;83%
With bathophenanthroline; water; copper diacetate; manganese(III) triacetate dihydrate In 1,4-dioxane at 90℃;76%
butyryl chloride
141-75-3

butyryl chloride

benzene
71-43-2

benzene

butyrophenone
495-40-9

butyrophenone

Conditions
ConditionsYield
Stage #1: butyryl chloride With aluminum (III) chloride In 1,2-dichloro-ethane at 0℃; for 0.166667h; Friedel-Crafts Acylation;
Stage #2: benzene In 1,2-dichloro-ethane at 50℃; for 2h; Friedel-Crafts Acylation;
90%
With aluminium trichloride
With aluminum (III) chloride
Stage #1: butyryl chloride With aluminum (III) chloride In 1,2-dichloro-ethane at 0℃; for 0.166667h;
Stage #2: benzene In 1,2-dichloro-ethane at 0 - 50℃; for 2h;
With aluminum (III) chloride In dichloromethane Friedel-Crafts Acylation;
iodobenzene
591-50-4

iodobenzene

carbon monoxide
201230-82-2

carbon monoxide

1-iodo-propane
107-08-4

1-iodo-propane

butyrophenone
495-40-9

butyrophenone

Conditions
ConditionsYield
With copper; zinc; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran at 50℃; under 760 Torr; for 24h;90%
With copper; zinc; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran at 50℃; under 760 Torr; for 24h; Product distribution; new ketone synthesis; aryl iodides with alkyl iodides or benzyl chlorides;90%
2-phenyl-2-propyl acetamide
14387-51-0

2-phenyl-2-propyl acetamide

butyrophenone
495-40-9

butyrophenone

Conditions
ConditionsYield
With tetraethylammonium bromide; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In acetonitrile at 20 - 60℃;90%
propyl cyanide
109-74-0

propyl cyanide

allylmagnesium bromide
2622-05-1

allylmagnesium bromide

phenyllithium
591-51-5

phenyllithium

A

4-phenylhept-1-en-4-amine

4-phenylhept-1-en-4-amine

B

butyrophenone
495-40-9

butyrophenone

Conditions
ConditionsYield
Stage #1: propyl cyanide; phenyllithium With water In dibutyl ether at 20℃; for 0.0166667h; Inert atmosphere; Schlenk technique;
Stage #2: allylmagnesium bromide With water In dibutyl ether at 20℃; for 0.0833333h; Inert atmosphere; Schlenk technique; chemoselective reaction;
A 90%
B 10%
ethanol
64-17-5

ethanol

1-Phenylethanol
98-85-1, 13323-81-4

1-Phenylethanol

butyrophenone
495-40-9

butyrophenone

Conditions
ConditionsYield
With chlorine[2-(4,5-dihydro-1H-imidazol-2-yl)-6-methoxypyridine](pentamethylcyclopentadienyl)iridium(III) chloride; potassium hydroxide In water at 80℃; Schlenk technique; Inert atmosphere;90%
With chlorine[2-(4,5-dihydro-1H-imidazol-2-yl)-6-methoxypyridine](pentamethylcyclopentadienyl)iridium(III) chloride; potassium hydroxide In water at 80℃; for 16h; Schlenk technique; Inert atmosphere; chemoselective reaction;90%
diethyl 1-trimethylsilyloxy-1-phenylbutylphosphonate
66731-84-8

diethyl 1-trimethylsilyloxy-1-phenylbutylphosphonate

butyrophenone
495-40-9

butyrophenone

Conditions
ConditionsYield
With sodium hydroxide In ethanol for 0.333333h;88%
2-phenyl-2-propyl-1,3-dioxolane
5660-57-1

2-phenyl-2-propyl-1,3-dioxolane

butyrophenone
495-40-9

butyrophenone

Conditions
ConditionsYield
With sodium tetrahydroborate; nickel(II) chloride hexahydrate In methanol for 3.5h; Reflux; chemoselective reaction;88%
α-n-propylstyrene
5676-32-4

α-n-propylstyrene

butyrophenone
495-40-9

butyrophenone

Conditions
ConditionsYield
With monoethylene glycol diethyl ether at 90℃; for 12h; Green chemistry;88%
With 1-hydroxy-pyrrolidine-2,5-dione; graphitic carbon nitride; oxygen In acetonitrile at 20℃; Inert atmosphere; Irradiation;72%
4-Octyne
1942-45-6

4-Octyne

N-fluorobis(benzenesulfon)imide
133745-75-2

N-fluorobis(benzenesulfon)imide

butyrophenone
495-40-9

butyrophenone

Conditions
ConditionsYield
With tert.-butylhydroperoxide; water; copper(II) sulfate In acetonitrile at 80℃; for 4h; Schlenk technique; Inert atmosphere;88%
butyrophenone
495-40-9

butyrophenone

Conditions
ConditionsYield
With hydroxylamine hydrochloride; sodium acetate In ethanol; water at 95℃;100%
With hydroxylamine hydrochloride; sodium acetate In ethanol; water for 2h; Reflux;89%
butyrophenone
495-40-9

butyrophenone

2-bromo-1-phenylbutan-1-one
877-35-0

2-bromo-1-phenylbutan-1-one

Conditions
ConditionsYield
With bromine at 20℃; for 0.333333h;100%
With Oxalyl bromide In dichloromethane; dimethyl sulfoxide at -10 - 30℃; for 0.666667h; Inert atmosphere;95%
With Oxalyl bromide; dimethyl sulfoxide In dichloromethane at -10 - 30℃; for 0.5h; Inert atmosphere;95%
sodium cyanide
773837-37-9

sodium cyanide

butyrophenone
495-40-9

butyrophenone

aniline
62-53-3

aniline

2-Phenyl-2-phenylamino-pentanenitrile
68230-34-2

2-Phenyl-2-phenylamino-pentanenitrile

Conditions
ConditionsYield
In acetic acid at 5 - 20℃; for 13h;100%
ethane-1,2-dithiol
540-63-6

ethane-1,2-dithiol

butyrophenone
495-40-9

butyrophenone

2-phenyl-2-propyl-1,3-dithiolane
5769-03-9

2-phenyl-2-propyl-1,3-dithiolane

Conditions
ConditionsYield
With amberlyst-15 In acetonitrile for 1h;99.9%
With PPA; silica gel In 1,2-dichloro-ethane at 20℃; for 2h;45%
With silica-supported aluminum chloride In 1,2-dichloro-ethane for 3h; Heating;17%
With hydrogenchloride
1.3-propanedithiol
109-80-8

1.3-propanedithiol

butyrophenone
495-40-9

butyrophenone

2-phenyl-2-propyl-1,3-dithiane
60832-18-0

2-phenyl-2-propyl-1,3-dithiane

Conditions
ConditionsYield
With amberlyst-15 In acetonitrile for 1h;99.9%
butyrophenone
495-40-9

butyrophenone

thiourea
17356-08-0

thiourea

5-ethyl-4-phenyl-1,3-thiazol-2-amine
34176-47-1

5-ethyl-4-phenyl-1,3-thiazol-2-amine

Conditions
ConditionsYield
With iodine at 100℃;99%
With iodine
With iodine at 100℃; for 14h;
butyrophenone
495-40-9

butyrophenone

1-Phenyl-1-butanol
614-14-2

1-Phenyl-1-butanol

Conditions
ConditionsYield
With Tetrahydrofurfuryl alcohol; sodium tetrahydroborate; ethanol; (S,S)-(β-oxoaldiminato)cobalt(II) In chloroform at -20℃; for 12h;99%
With sodium tetrahydroborate In ethanol for 5h;96.2%
With C44H40ClN2NiP2(1+)*F6P(1-); hydrogen; potassium hydroxide In isopropyl alcohol at 120℃; under 30003 Torr; for 12h; Autoclave;96%
butyrophenone
495-40-9

butyrophenone

(S)-1-phenylbutan-1-ol
22135-49-5

(S)-1-phenylbutan-1-ol

Conditions
ConditionsYield
With bis(1,5-cyclooctadiene)diiridium(I) dichloride; C53H73FeN2O2PS; hydrogen; lithium tert-butoxide In isopropyl alcohol at 25 - 30℃; under 22801.5 Torr; for 12h; Autoclave; enantioselective reaction;99%
With sodium tetrahydroborate; third-generation glucose-persubstituted amidoamine dendrimer In tetrahydrofuran at 25℃;96%
With C58H56Cl2N2P2Ru; potassium tert-butylate; hydrogen In isopropyl alcohol at 25℃; under 6080.41 Torr; for 3h; Inert atmosphere; optical yield given as %ee;96%
trimethylsilyl cyanide
7677-24-9

trimethylsilyl cyanide

butyrophenone
495-40-9

butyrophenone

2-phenyl-2-trimethylsilyloxy-pentanenitrile

2-phenyl-2-trimethylsilyloxy-pentanenitrile

Conditions
ConditionsYield
With N,N-dimethyl-(2-hydroxybenzyl)amine N-oxide In diethyl ether at 23℃; for 3h;99%
With tin ion-exchanged montmorillonite In dichloromethane at 20℃; for 0.0333333h; Inert atmosphere;98%
indium(III) bromide In dichloromethane at 20℃; for 16h;96%
With indium(III) bromide In dichloromethane at 20℃; for 3h;94%
ethyl acetoacetate
141-97-9

ethyl acetoacetate

butyrophenone
495-40-9

butyrophenone

malononitrile
109-77-3

malononitrile

6-amino-2,4-dihydro-3-methyl-4-phenyl-4-propylpyrano[2,3-c]pyrazole-5-carbonitrile
1235990-51-8

6-amino-2,4-dihydro-3-methyl-4-phenyl-4-propylpyrano[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%
2,2,6,6-tetramethyl-piperidine-N-oxyl
2564-83-2

2,2,6,6-tetramethyl-piperidine-N-oxyl

butyrophenone
495-40-9

butyrophenone

1-phenyl-2-((2,2,6,6-tetramethylpiperidin-1-yl)oxy)butan-1-one
1394206-52-0

1-phenyl-2-((2,2,6,6-tetramethylpiperidin-1-yl)oxy)butan-1-one

Conditions
ConditionsYield
With 2,6-di-tert-butyl-pyridine; 2-chloro-1,3,2-benzodioxaborole In dichloromethane at 0 - 20℃; for 3h;99%
butyrophenone
495-40-9

butyrophenone

1-phenyl-1-butanone-d12

1-phenyl-1-butanone-d12

Conditions
ConditionsYield
With 10% Pt/activated carbon; water-d2 In cyclohexane; isopropyl alcohol at 80℃; for 24h; Inert atmosphere;99%
methanol
67-56-1

methanol

butyrophenone
495-40-9

butyrophenone

2-methyl-1-phenyl-butan-1-one
938-87-4

2-methyl-1-phenyl-butan-1-one

Conditions
ConditionsYield
With trimethylamine-N-oxide; tricarbonyl(η4-1,3-bis(trimethylsilyl)-4,5,6,7-tetrahydro-2H-inden-2-one)iron; potassium carbonate at 80℃; for 24h; Catalytic behavior; Reagent/catalyst; Temperature;99%
With C34H27IrN2P(1+)*C32H12BF24(1-); caesium carbonate at 65℃; for 24h; Reagent/catalyst; Inert atmosphere;97%
With bis[dichloro(pentamethylcyclopentadienyl)ruthenium(III)]; bis[2-(diphenylphosphino)phenyl] ether; lithium tert-butoxide at 110℃; for 24h; Catalytic behavior; Reagent/catalyst; Temperature; Inert atmosphere; regioselective reaction;96%
4-methylphenyl isocyanide
7175-47-5

4-methylphenyl isocyanide

butyrophenone
495-40-9

butyrophenone

C18H19NO

C18H19NO

Conditions
ConditionsYield
With 1,3-bis(mesityl)imidazolium chloride; sodium t-butanolate In N,N-dimethyl acetamide at 80℃; for 12h;99%
ketene t-butyldimethylsilyl methyl acetal
77086-38-5

ketene t-butyldimethylsilyl methyl acetal

butyrophenone
495-40-9

butyrophenone

methyl 3-((tert-butyldimethylsilyl)oxy)-3-phenylhexanoate

methyl 3-((tert-butyldimethylsilyl)oxy)-3-phenylhexanoate

Conditions
ConditionsYield
Stage #1: propiophenone With bis(trifluoromethanesulfonyl)amide In diethyl ether at -78 - 23℃; Mukaiyama Aldol Addition; Schlenk technique; Inert atmosphere;
Stage #2: ketene t-butyldimethylsilyl methyl acetal In diethyl ether at -20℃; for 0.5h; Mukaiyama Aldol Addition; Schlenk technique; Inert atmosphere;
99%
butyrophenone
495-40-9

butyrophenone

1-butylbenzene
104-51-8

1-butylbenzene

Conditions
ConditionsYield
With amalgamated zinc; hydrogen iodide In methanol for 5h; Irradiation;98%
With hydrogen; K-10 montmorillonite; platinum In diethylene glycol dimethyl ether under 37503 Torr; for 30h; Reduction;97%
With hydrogen In 1,4-dioxane at 220℃; under 15001.5 Torr;97.3%
butyrophenone
495-40-9

butyrophenone

(R)-1-butylphenylethanol
22144-60-1

(R)-1-butylphenylethanol

Conditions
ConditionsYield
With (2-((2,4-dimethyl-5-phenylimidazo[1,5-b]pyridazin-7-yl)amido)-4-methylpentan-1-ol)(1,5-cyclooctadiene)iridium(I); potassium tert-butylate; hydrogen; acetone In tetrahydrofuran at 20℃; under 15.0015 Torr; for 48h; Autoclave; optical yield given as %ee; enantioselective reaction;98%
With triethylboron hydride; hydrogen; (R)-CoCl2[4'-phenyl-5-OMeCH3PyCH2NH(CH2)2PPh2]; tris(5-ethyl-2-furanyl)phosphine; caesium carbonate In diethyl ether at 25℃; under 30003 Torr; for 12h; Autoclave; enantioselective reaction;98%
With C44H48FeIrNO2P(1+)*C32H12BF24(1-); hydrogen; sodium carbonate In methanol at 20℃; under 3750.38 Torr; for 24h; Autoclave; enantioselective reaction;97%
butyrophenone
495-40-9

butyrophenone

[2,2-d2]-1-phenylbutan-1-one
129848-88-0

[2,2-d2]-1-phenylbutan-1-one

Conditions
ConditionsYield
With [D]-sodium hydroxide; deuteromethanol In water-d2 for 15h; Reflux;98%
by exchanging twice, 2 M NaOH, reflux, 16 h; Multistep reaction;
Multi-step reaction with 2 steps
1: bromine / dichloromethane / 0.25 h
2: water-d2; potassium carbonate / d(4)-methanol / 20 h / 20 °C / Inert atmosphere
View Scheme
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

butyrophenone
495-40-9

butyrophenone

4-phenylhept-1-en-4-ol
124734-11-8

4-phenylhept-1-en-4-ol

Conditions
ConditionsYield
With methanol; indium (III) tris(hexamethyldisilyl) amide In toluene at 20℃; for 6h; Inert atmosphere;98%
With indium In water at 30℃; for 24h; Inert atmosphere;92%
butyrophenone
495-40-9

butyrophenone

(Z)-(1-chloro-1-butenyl)benzene
28273-67-8

(Z)-(1-chloro-1-butenyl)benzene

Conditions
ConditionsYield
With silica gel; acetyl chloride; zinc(II) chloride In 1,2-dichloro-ethane at 30℃; for 1h;97%
With silica-supported ZnCl2 (30%); acetyl chloride In 1,2-dichloro-ethane for 1h; Inert atmosphere;85%
With iron(III) chloride; butyryl chloride

495-40-9Relevant articles and documents

Aqueous aerobic oxidation of alkyl arenes and alcohols catalyzed by copper(ii) phthalocyanine supported on three-dimensional nitrogen-doped graphene at room temperature

Mahyari, Mojtaba,Laeini, Mohammad Sadegh,Shaabani, Ahmad

, p. 7855 - 7857 (2014)

Copper(ii) tetrasulfophthalocyanine supported on three-dimensional nitrogen-doped graphene-based frameworks was synthesized and introduced as a bifunctional catalyst for selective aerobic oxidation of alkyl arenes and alcohols to the corresponding carbonyl compounds. The ease of catalyst separation, high turnover, low catalyst loading and recyclability could potentially render it applicable in industrial setting. This journal is the Partner Organisations 2014.

Gold nanoparticles supported on three-dimensional nitrogen-doped graphene: An efficient catalyst for selective aerobic oxidation of hydrocarbons under mild conditions

Mahyari, Mojtaba,Laeini, Mohammad Sadegh,Shaabani, Ahmad,Kazerooni, Hanif

, p. 456 - 461 (2015)

The development of efficient and selective aerobic oxidation of alkylarenes to form more functional compounds by heterogeneously catalysed routes still presents a great challenge in the fine chemical industry and is a major research topic. In this work, gold nanoparticles supported on three-dimensional nitrogen-doped graphene-based frameworks (Au NPs@3D-(N)GFs) were successfully synthesized and found to have an impressive performance as bifunctional catalysts (nitrogen dopant as base and gold nanoparticles as active site) in the controlled oxidation of alkylarenes. The catalyst was found to be a simple bench top, stable, recyclable and selective catalytic system for the aerobic oxidation of various types of alkylarenes into their corresponding ketones at room temperature under environmentally friendly conditions with good yields and high selectivity.

Reductive selenation of aliphatic ketones to dialkyl diselenides with Se-CO-H2O under atmospheric pressure

Chen, Yahong,Tian, Fengshou,Song, Maoping,Lu, Shiwei

, p. 1235 - 1237 (2008)

-

Diastereoselective reductive aldol reaction of enones to ketones catalyzed by halogenotin hydride

Shibata, Ikuya,Tsunoi, Shinji,Sakabe, Kumiko,Miyamoto, Shinji,Kato, Hirofumi,Nakajima, Hideto,Yasuda, Makoto,Baba, Akio

, p. 13335 - 13338 (2010)

It's in the tin: The reductive aldol reaction of enones has been established by the Bu2SnClH (cat.)/Ph2SiH2/MeOH system (see scheme). The reaction of enones with α-ketoesters or α-alkoxyketones is highly diastereoselective through a chelation-controlled mechanism. Copyright

Indium hydride catalyzed chemo- and diastereoselective reductive aldol reactions

Ieki, Ryosuke,Miyamoto, Shinji,Tsunoi, Shinji,Shibata, Ikuya

, p. 471 - 474 (2014)

The reductive aldol reaction of enones has been established catalyzed by Br2InOMe (cat.)-MePhSiH2 system where Br2InH acted as an active catalytic species. Addition of 1.0 equivalent of MeOH was essential for catalytic turnover. The system, Br2InOMe(cat.)- MePhSiH2-MeOH, provided highly chemoand diastereoselective reductive aldol reaction of enones with functionalized substrates such as α-bromo carbonyls, α-keto esters and α-alkoxy ketones.

Sonochemical fabrication of Pd/TiO2-nanotubes/Ti plate as a green catalyst for oxidation of alkylarenes and benzyl alcohols

Keshipour, Sajjad,Faraji, Masoud,Asl, Parisa Aboozari

, p. 1423 - 1429 (2019)

A facile and fast strategy has been employed to fabricate Pd nanoparticles supported on TiO2 nanotubes/Ti plate via sonochemical deposition. Microstructure studies showed the homogeneous deposition of Pd nanoparticles on the walls of TiO2 nanotubes/Ti plate. The synthesized plate was applied as a novel catalyst for the oxidation of benzyl alcohol and ethylbenzene derivatives. The results of catalytic experiments demonstrated that the modified plate was an efficient green catalyst for the oxidation of benzyl alcohols to benzoic acid derivatives in H2O. The oxidation of alkylarenes was carried out in EtOH:H2O (1:1) ended up with the formation of the corresponding ketone as the sole product. High yields and excellent selectivities were obtained for the oxidation reactions in green solvents using green oxidant. Superior catalytic activity, easy catalyst recovery, and reusability of the catalyst are some advantages of the modified PdNPs/TiO2 nanotubes/Ti plate, indicating a potential application of the catalyst in the industrial oxidation reactions.

Nickel-Catalyzed Reductive Acylation of Carboxylic Acids with Alkyl Halides and N-Hydroxyphthalimide Esters Enabled by Electrochemical Process

Guo, Lin,Xia, Raymond Yang,Xia, Wujiong,Yang, Chao,Zhang, Haoxiang,Zhou, Xiao

supporting information, (2022/03/31)

A sustainable Ni-catalyzed reductive acylation reaction of carboxylic acids via an electrochemical pathway is presented, affording a variety of ketones as major products. The reaction proceeds at ambient temperature using unactivated alkyl halides and N-hydroxyphthalimide (NHP) esters as coupling partners, which exhibits several synthetic advantages, including mild conditions and convenience of amplification (58% yield for 6 mmol scale reaction). (Figure presented.).

Designed pincer ligand supported Co(ii)-based catalysts for dehydrogenative activation of alcohols: Studies onN-alkylation of amines, α-alkylation of ketones and synthesis of quinolines

Singh, Anshu,Maji, Ankur,Joshi, Mayank,Choudhury, Angshuman R.,Ghosh, Kaushik

, p. 8567 - 8587 (2021/06/30)

Base-metal catalystsCo1,Co2andCo3were synthesized from designed pincer ligandsL1,L2andL3having NNN donor atoms respectively.Co1,Co2andCo3were characterized by IR, UV-Vis. and ESI-MS spectroscopic studies. Single crystal X-ray diffraction studies were investigated to authenticate the molecular structures ofCo1andCo3. CatalystsCo1,Co2andCo3were utilized to study the dehydrogenative activation of alcohols forN-alkylation of amines, α-alkylation of ketones and synthesis of quinolines. Under optimized reaction conditions, a broad range of substrates including alcohols, anilines and ketones were exploited. A series of control experiments forN-alkylation of amines, α-alkylation of ketones and synthesis of quinolines were examined to understand the reaction pathway. ESI-MS spectral studies were investigated to characterize cobalt-alkoxide and cobalt-hydride intermediates. Reduction of styrene by evolved hydrogen gas during the reaction was investigated to authenticate the dehydrogenative nature of the catalysts. Probable reaction pathways were proposed forN-alkylation of amines, α-alkylation of ketones and synthesis of quinolines on the basis of control experiments and detection of reaction intermediates.

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