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100-52-7

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100-52-7 Usage

Chemical Description

Different sources of media describe the Chemical Description of 100-52-7 differently. You can refer to the following data:
1. Benzaldehyde is an aromatic aldehyde used as a substrate in the synthesis of cyanohydrins.
2. Benzaldehyde is an organic compound with the formula C6H5CHO.
3. Benzaldehyde is an organic compound with the chemical formula C6H5CHO.
4. Benzaldehyde is an aldehyde used in the study, and NH4Cl is used to quench the reaction.
5. Benzaldehyde is an aromatic aldehyde used as a flavoring agent and in the synthesis of other chemicals.
6. Benzaldehyde is an aromatic aldehyde used in the production of fragrances and flavors.
7. Benzaldehyde is used as a reactant in the synthesis of propargylic alcohols.
8. Benzaldehyde is an organic compound with a sweet, almond-like odor.
9. Benzaldehyde is used as a reactant in the preparation of one of the primary phosphine oxides.
10. Benzaldehyde is used in the condensation reaction to obtain the pyrimidine derivative 13.
11. Benzaldehyde is a colorless liquid with a bitter almond odor, used in the production of fragrances, dyes, and pharmaceuticals.
12. Benzaldehyde is an organic compound with the formula C6H5CHO, used as a flavoring agent and in the manufacture of dyes and perfumes.
13. Benzaldehyde is an aromatic aldehyde, and allylic alcohols are alcohols with an allylic group, which is a carbon-carbon double bond adjacent to a carbon-carbon single bond.

Safety Profile

Poison by ingestion andintraperitoneal routes. Moderately toxic by subcutaneousroute. An allergen. Acts as a feeble local anesthetic. Localcontact may cause contact dermatitis. Causes centralnervous system depression in small doses and convulsionsin

Check Digit Verification of cas no

The CAS Registry Mumber 100-52-7 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,0 and 0 respectively; the second part has 2 digits, 5 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 100-52:
(5*1)+(4*0)+(3*0)+(2*5)+(1*2)=17
17 % 10 = 7
So 100-52-7 is a valid CAS Registry Number.
InChI:InChI=1/C7H6O/c8-6-7-4-2-1-3-5-7/h1-6H

100-52-7SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name benzaldehyde

1.2 Other means of identification

Product number -
Other names Benzoylhydride

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:100-52-7 SDS

100-52-7Synthetic route

styrene
292638-84-7

styrene

benzaldehyde
100-52-7

benzaldehyde

Conditions
ConditionsYield
With sodium periodate; C31H29Br2N3Ru*CH2Cl2 In water; ethyl acetate; acetonitrile at 25℃; for 0.5h; Activation energy; Reagent/catalyst; Solvent; Temperature; Inert atmosphere; Schlenk technique;100%
With ruthenium trichloride; [bis(acetoxy)iodo]benzene In dichloromethane; water at 30℃; for 1.5h; Catalytic behavior; Reagent/catalyst; Solvent;99.8%
With sodium periodate; C22H23ClIN2Os(1+)*F6P(1-) In water; tert-butyl alcohol at 60℃; Catalytic behavior; Reagent/catalyst; Schlenk technique; Inert atmosphere;97%
stilbene
588-59-0

stilbene

benzaldehyde
100-52-7

benzaldehyde

Conditions
ConditionsYield
With oxygen In dichloromethane at 20℃; for 2h; visible light irradiation;100%
With sodium periodate; [η5-C5H5Ru(CO)2NH2C6H11]BF4 In water; acetonitrile at 60℃; for 1h; Catalytic behavior; Schlenk technique; Inert atmosphere;100%
With dihydrogen peroxide In acetonitrile at 65℃; for 6h;96%
Conditions
ConditionsYield
With dinitratocerium (IV) chromate In benzene for 0.666667h; Heating;100%
With tris paraperiodate In benzene for 1.5h; Heating;100%
With pyridine chromium peroxide In dichloromethane for 0.25h; Product distribution; Ambient temperature; effect of various chromium(VI) based oxidants;100%
toluene
108-88-3

toluene

benzaldehyde
100-52-7

benzaldehyde

Conditions
ConditionsYield
With laccase from Coriolus versicolor MTCC-138; 2,2'-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) diammonium salt In 1,4-dioxane for 0.5h; pH=4.5; Green chemistry; Enzymatic reaction;100%
With nickel-doped graphene carbon nitride nanoparticles; air In ethanol at 25℃; for 8h; Reagent/catalyst; Solvent; Irradiation; Green chemistry;98%
With water at 20℃; for 3h; Reagent/catalyst;98%
benzylamine
100-46-9

benzylamine

benzaldehyde
100-52-7

benzaldehyde

Conditions
ConditionsYield
With dinitratocerium (IV) chromate In benzene for 1.25h; Heating;100%
With 2,2'-bipyridylchromium peroxide for 0.4h; Product distribution; effect of various chromium(VI) based oxidants;100%
With barium ferrate(VI) In benzene for 1h; Product distribution; Heating;100%
benzyl alcohol
100-51-6

benzyl alcohol

benzaldehyde
100-52-7

benzaldehyde

Conditions
ConditionsYield
With bis(pyridine)silver(I) permanganate In benzene for 0.5h;100%
With pyridine chromium peroxide In dichloromethane for 0.5h; Ambient temperature;100%
With manganese(IV) oxide; Pyridine-2,6-dicarboxylic acid In water; acetonitrile at 20℃; for 20h;100%
cyclohexene sulfide
286-28-2

cyclohexene sulfide

cis-2-methyl-3-phenyloxaziridine
39245-63-1

cis-2-methyl-3-phenyloxaziridine

A

(Z)-azomethane
4143-42-4

(Z)-azomethane

B

N,N'-bis(methyl)sulphur di-imide
13849-02-0, 84878-02-4, 84878-03-5, 84878-04-6

N,N'-bis(methyl)sulphur di-imide

C

benzaldehyde
100-52-7

benzaldehyde

D

cyclohexene
110-83-8

cyclohexene

Conditions
ConditionsYield
In chloroform Mechanism; Ambient temperature; via thionitrosomethane, CH3NS (also used: other oxaziridines and episulfides);A n/a
B 83%
C 100%
D 100%
(2,3-dihydro-4H-benzo[b][1,4]oxazin-4-yl)(phenyl)methanone
19202-00-7

(2,3-dihydro-4H-benzo[b][1,4]oxazin-4-yl)(phenyl)methanone

A

1,4-benzoxazine
5735-53-5

1,4-benzoxazine

B

benzaldehyde
100-52-7

benzaldehyde

Conditions
ConditionsYield
With sodium bis(2-methoxyethoxy)aluminium dihydride In ethyl acetate; benzene at -40℃;A 100%
B 100%
2-phenyl-1,3-dioxolane
936-51-6

2-phenyl-1,3-dioxolane

benzaldehyde
100-52-7

benzaldehyde

Conditions
ConditionsYield
1,3-di(NCS)-tetrabutyldistannoxane In diethylene glycol dimethyl ether; water at 100℃; for 2h; Deprotection of acetal;100%
Tetrabutyl-1,3-diisothiocyanato-distannoxane In diethylene glycol dimethyl ether; water at 100℃; for 2h;100%
With 4-phenyl-2,2,5,5-tetramethyl-3-imidazolin-1-yloxy-3-oxide; 15-crown-5; KCrO5Cl In acetonitrile at 60℃; for 7h; Product distribution; Further Variations:; Reagents;100%
phenylethane 1,2-diol
93-56-1

phenylethane 1,2-diol

4-cyano-N,N-dimethylaniline-N-oxide
62820-00-2

4-cyano-N,N-dimethylaniline-N-oxide

A

formaldehyd
50-00-0

formaldehyd

B

4-cyano-N-methylaniline
4714-62-9

4-cyano-N-methylaniline

C

benzaldehyde
100-52-7

benzaldehyde

D

4-cyano-N,N-dimethylaniline
1197-19-9

4-cyano-N,N-dimethylaniline

Conditions
ConditionsYield
With chloro(5,10,15,20-tetraphenylporphyrinato)chromium(III) In acetonitrile for 0.666667h; Rate constant; Ambient temperature; Irradiation; oxygen transfer was investigated, different irradiation time;A n/a
B n/a
C 100%
D 100%
phenylethane 1,2-diol
93-56-1

phenylethane 1,2-diol

benzaldehyde
100-52-7

benzaldehyde

Conditions
ConditionsYield
With tris paraperiodate In benzene for 1.5h; Heating;100%
With N-iodo-succinimide In tetrahydrofuran for 3h; Ambient temperature; in the dark;98%
With calcium hypochlorite; water; aluminum oxide for 0.00555556h; microwave irradiation;98%
2-Phenyl-[1,3]dithiane
5425-44-5

2-Phenyl-[1,3]dithiane

benzaldehyde
100-52-7

benzaldehyde

Conditions
ConditionsYield
With K-10 clay supported copper(II) nitrate trihydrate In dichloromethane for 5h; Ambient temperature; K-10 clay supported iron(III) nitrate nonahydrate; mild cleavege of thioacetals into the corresponding carbonyl compounds;100%
With K-10 clay supported iron(III) nitrate nonahydrate In dichloromethane for 5h; Ambient temperature; with K-10 clay-supported copper(II) nitrate trihydrate;100%
With dihydrogen peroxide; iodine; sodium dodecyl-sulfate In water at 20℃; for 0.75h; Micellar solution;100%
(E)-1,2-diphenyl-ethene
103-30-0

(E)-1,2-diphenyl-ethene

benzaldehyde
100-52-7

benzaldehyde

Conditions
ConditionsYield
With 1,2,3,4,5-pentafluoro-6-iodosylbenzene; iron(III) perchlorate In acetonitrile at -10℃; for 0.0833333h;100%
With air; [Pt(2,2':6',2'':6'',2'''-quaterpyridine)](CF3SO3)2; Nafion In acetonitrile at 20℃; for 5h; Irradiation;100%
With sodium periodate; osmium(VIII) oxide In tetrahydrofuran; water at 20℃;99%
(2-methyl-1-propenyl)-benzene
768-49-0

(2-methyl-1-propenyl)-benzene

benzaldehyde
100-52-7

benzaldehyde

Conditions
ConditionsYield
With sodium nitrite In water; acetic acid 1.) 0 deg C 2.) 60 deg C, 0,5 h;100%
With oxygen at 25℃; under 1500.15 Torr; for 24h; pH=6; aq. buffer; Enzymatic reaction; chemoselective reaction;
benzyloxy-trimethylsilane
14642-79-6

benzyloxy-trimethylsilane

benzaldehyde
100-52-7

benzaldehyde

Conditions
ConditionsYield
With benzyltriphenylphosphonium chlorate; aluminium trichloride In acetonitrile for 0.25h; Heating;100%
With nitrogen dioxide at 20℃; for 0.0833333h;100%
With N-benzyl-N,N-dimethyl anilinium peroxodisulfate In acetonitrile for 0.0833333h; Reflux;99%
(diethoxymethyl)benzene
774-48-1

(diethoxymethyl)benzene

benzaldehyde
100-52-7

benzaldehyde

Conditions
ConditionsYield
With water at 80℃; for 2h;100%
With iodo trichloro silane for 0.333333h; Ambient temperature;95%
With iodo trichloro silane for 0.333333h; Product distribution; Mechanism; Ambient temperature; other acyclic and cyclic acetals and ketals;95%
benzaldehyde p-toluenesulfonylhydrazone
1666-17-7

benzaldehyde p-toluenesulfonylhydrazone

benzaldehyde
100-52-7

benzaldehyde

Conditions
ConditionsYield
With copper(II) sulfate In tetrahydrofuran; methanol; water for 24h; Heating;100%
With Cr-MCM-41 zeolite on silica gel for 0.1h; microwave irradiation;96%
With copper(II) nitrate In tetrachloromethane at 25℃; for 2h; regeneration of aldehydes and ketones from tosylhydrazones; further tosylhydrazones;92%
benzyl nitrite
935-05-7

benzyl nitrite

benzaldehyde
100-52-7

benzaldehyde

Conditions
ConditionsYield
With nitric acid In dichloromethane at 20℃; for 1h;100%
With sulfuric acid In dichloromethane; water for 0.5h; in air;100%
With dimethyl sulfoxide at 70℃; for 6h;87.9%
With Amberlyst-15 In 1,4-dioxane at 40℃; Kinetics; Concentration; Temperature;
benzaldehyde dimethyl acetal
1125-88-8

benzaldehyde dimethyl acetal

benzaldehyde
100-52-7

benzaldehyde

Conditions
ConditionsYield
sodium tetrakis[(3,5-di-trifluoromethyl)phenyl]borate In water at 30℃; for 0.0833333h;100%
With water at 80℃; for 2h;100%
With water at 90℃; Inert atmosphere;100%
benzylidene 1,1-diacetate
581-55-5

benzylidene 1,1-diacetate

benzaldehyde
100-52-7

benzaldehyde

Conditions
ConditionsYield
With [NO(1+)*18-crown-6*H(NO3)2(1-)]; silica gel In dichloromethane at 20℃; for 0.0833333h;100%
With sulphated zirconia In acetonitrile at 60℃; for 0.45h; Microwave irradiation;100%
With aluminum oxide at 35℃; for 0.0111111h; microwave irradiation;98%
benzaldehyde dibenzyldithioacetal
5418-20-2

benzaldehyde dibenzyldithioacetal

A

dibenzyl disulphide
150-60-7

dibenzyl disulphide

B

benzaldehyde
100-52-7

benzaldehyde

Conditions
ConditionsYield
With hydrogenchloride; sodium nitrate In tetrachloromethane; water for 5h; Ambient temperature; other reagent;A n/a
B 100%
1-(N,N-dibenzylamino)cyclopropanecarboxylic acid
119111-63-6

1-(N,N-dibenzylamino)cyclopropanecarboxylic acid

A

benzaldehyde
100-52-7

benzaldehyde

B

1-(N-benzylamino)cyclopropanecarboxylic acid hydrochloride
119111-75-0

1-(N-benzylamino)cyclopropanecarboxylic acid hydrochloride

Conditions
ConditionsYield
With pivaloyl chloride In chloroform Ambient temperature;A 100%
B 63%
benzaldehyde semicarbazone
1574-10-3

benzaldehyde semicarbazone

benzaldehyde
100-52-7

benzaldehyde

Conditions
ConditionsYield
With Oxone; silica gel In dichloromethane for 0.333333h; Reflux;100%
With benzyltriphenylphosphonium dichromate; silica gel for 0.166667h;97%
With hexaaquairon(III) perchlorate for 2h;96%
1-Acetamido-N-benzyloxy-6,7-dihydro-5H-dibenzazepin
83080-95-9

1-Acetamido-N-benzyloxy-6,7-dihydro-5H-dibenzazepin

A

benzaldehyde
100-52-7

benzaldehyde

B

1-Acetamido-5H-dibenzazepin-N-oxid
83081-01-0

1-Acetamido-5H-dibenzazepin-N-oxid

C

11-Acetamido-5H-dibenzazepin-N-oxid
83081-02-1

11-Acetamido-5H-dibenzazepin-N-oxid

Conditions
ConditionsYield
With dihydrogen peroxide In acetic acid for 1.66667h; Ambient temperature; Yield given. Title compound not separated from byproducts;A 100%
B n/a
C n/a
benzaldehyde phenylhydrazone
588-64-7

benzaldehyde phenylhydrazone

benzaldehyde
100-52-7

benzaldehyde

Conditions
ConditionsYield
With copper(II) sulfate In tetrahydrofuran; methanol; water for 6h; Heating;100%
With baker's yeast; phosphate buffer In ethanol at 37℃; for 12h;98%
With CuCl*Kieselghur; oxygen In dichloromethane at 20℃; for 0.416667h;98%
tetrahydro-2-(benzyloxy)-2H-pyran
1927-62-4

tetrahydro-2-(benzyloxy)-2H-pyran

benzaldehyde
100-52-7

benzaldehyde

Conditions
ConditionsYield
With aluminium trichloride; benzyltriphenylphosphonium chlorate In acetonitrile at 20℃; for 3h;100%
With aluminium trichloride; tetramethylammonium chlorochromate In acetonitrile for 0.75h; Heating;98%
With β‐cyclodextrin; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In water; acetone at 20℃; for 1h;96%
2-hydroxy-1,2,3-triphenyl-propan-1-one
7540-93-4

2-hydroxy-1,2,3-triphenyl-propan-1-one

A

phenyl benzyl ketone
451-40-1

phenyl benzyl ketone

B

2-hydroxy-2-phenylacetophenone
119-53-9

2-hydroxy-2-phenylacetophenone

C

benzaldehyde
100-52-7

benzaldehyde

Conditions
ConditionsYield
With tetra-n-butylammonium cyanide In tetrahydrofuran for 1h; Heating;A 100%
B 38%
C 6%
α-(2-cyanoethyl)benzoin
174869-02-4

α-(2-cyanoethyl)benzoin

A

4-oxo-4-phenylbutanenitrile
5343-98-6

4-oxo-4-phenylbutanenitrile

B

2-hydroxy-2-phenylacetophenone
119-53-9

2-hydroxy-2-phenylacetophenone

C

benzaldehyde
100-52-7

benzaldehyde

Conditions
ConditionsYield
With tetra-n-butylammonium cyanide In tetrahydrofuran for 1h; Ambient temperature;A 100%
B 75%
C 2%
2-phenyl-1,3-dioxane
772-01-0

2-phenyl-1,3-dioxane

benzaldehyde
100-52-7

benzaldehyde

Conditions
ConditionsYield
With 4-phenyl-2,2,5,5-tetramethyl-3-imidazolin-1-yloxy-3-oxide; 15-crown-5; KCrO5Cl In acetonitrile at 60℃; for 7h; Product distribution; Further Variations:; Reagents;100%
indium(III) chloride In methanol; water for 1.16667h; Heating;93%
With water; sodium acetate; Pyridine hydrobromide In methanol at 20℃; for 24h; Reagent/catalyst;9%
4-chloromethyl-2-phenyl[1,3]dioxolane
36236-72-3

4-chloromethyl-2-phenyl[1,3]dioxolane

benzaldehyde
100-52-7

benzaldehyde

Conditions
ConditionsYield
With 4-phenyl-2,2,5,5-tetramethyl-3-imidazolin-1-yloxy-3-oxide; 15-crown-5; KCrO5Cl In acetonitrile at 60℃; for 7h; Product distribution; Further Variations:; Reagents;100%
piperidine
110-89-4

piperidine

benzaldehyde
100-52-7

benzaldehyde

1,1'-benzylidenedipiperidine
2538-76-3

1,1'-benzylidenedipiperidine

Conditions
ConditionsYield
With copper(II) bis(trifluoromethanesulfonate) In water at 20℃; for 0.0333333h;100%
In ethanol at 25℃; for 0.5h;95%
With aluminum oxide In diethyl ether at 20℃;90%
morpholine
110-91-8

morpholine

benzaldehyde
100-52-7

benzaldehyde

4,4'-(phenylmethylene)bismorpholine
6425-08-7

4,4'-(phenylmethylene)bismorpholine

Conditions
ConditionsYield
With copper(II) bis(trifluoromethanesulfonate) In water at 20℃; for 0.0333333h;100%
In benzene at 20℃; for 16h; Inert atmosphere;99%
In benzene Reflux;95%
2-methyl-1H-indole
95-20-5

2-methyl-1H-indole

benzaldehyde
100-52-7

benzaldehyde

2-methyl-3-((2-methyl-1H-indol-3-yl)(phenyl)methyl)-1H-indole
17371-59-4

2-methyl-3-((2-methyl-1H-indol-3-yl)(phenyl)methyl)-1H-indole

Conditions
ConditionsYield
With C62H58N8O20Y2Zn2 In ethanol; water for 2h; Friedel-Crafts Alkylation;100%
With tris(hydroxymethyl)methane ammonium hydrogensulphate In neat (no solvent) at 20℃; for 0.0833333h; Green chemistry;99%
With ruthenium trichloride In methanol at 20℃; for 0.05h;98%
N-methyl-N-(pyridin-2-yl)hydrazine
4231-74-7

N-methyl-N-(pyridin-2-yl)hydrazine

benzaldehyde
100-52-7

benzaldehyde

(E)-2-benzylidene-1-methyl-1-(pyridin-2-yl)hydrazine
4231-75-8

(E)-2-benzylidene-1-methyl-1-(pyridin-2-yl)hydrazine

Conditions
ConditionsYield
In ethanol for 6h; Reflux;100%
With water
2-oxoindole
59-48-3

2-oxoindole

benzaldehyde
100-52-7

benzaldehyde

3-benzylideneoxindole
3359-49-7, 23772-61-4, 23782-37-8

3-benzylideneoxindole

Conditions
ConditionsYield
With UiO-66 metal organic framework nanoparticles In neat (no solvent) at 80℃; for 2h; Friedel-Crafts Alkylation; Sealed tube; Darkness;100%
With pyrrolidine In ethanol for 2h; Reflux;94%
With [1-(3-sulfonic acid)]propyl-3-methylimidazolium hydrogen sulfate at 80℃; for 1h;93%
4-aminourazole
21531-96-4

4-aminourazole

benzaldehyde
100-52-7

benzaldehyde

4-benzylidenamino-[1,2,4]triazolidine-3,5-dione
4114-10-7

4-benzylidenamino-[1,2,4]triazolidine-3,5-dione

Conditions
ConditionsYield
In water for 0.5h; Reflux;100%
With water
isobutylamine
78-81-9

isobutylamine

benzaldehyde
100-52-7

benzaldehyde

benzylideneisobutylamine
27845-49-4, 6852-57-9

benzylideneisobutylamine

Conditions
ConditionsYield
at 20℃; for 2h;100%
91%
cyclohexanone
108-94-1

cyclohexanone

benzaldehyde
100-52-7

benzaldehyde

2-Benzylidenecyclohexanone
5682-83-7

2-Benzylidenecyclohexanone

Conditions
ConditionsYield
Stage #1: cyclohexanone With sodium hydroxide In ethanol; water at 0 - 5℃;
Stage #2: benzaldehyde In ethanol; water
100%
With CaO modified with benzyl bromide In methanol at 65℃; under 760.051 Torr; for 3h; Reagent/catalyst; Concentration; Temperature; Time;95.8%
With N,N-Dimethyltrimethylsilylamine; magnesium bromide ethyl etherate at 20℃; for 16h; Inert atmosphere; neat (no solvent);93%
acetic anhydride
108-24-7

acetic anhydride

benzaldehyde
100-52-7

benzaldehyde

benzylidene 1,1-diacetate
581-55-5

benzylidene 1,1-diacetate

Conditions
ConditionsYield
With poly(4-vinylpyridine)-supported sulfuric acid In dichloromethane at 20℃; for 0.25h; Green chemistry; chemoselective reaction;100%
With SBA-15-Ph-PrSO3H at 20℃; for 0.0833333h; Green chemistry;100%
With poly(4-vinylpyridinium) perchlorate In neat (no solvent) at 20℃; for 0.0333333h; Time; Green chemistry; chemoselective reaction;100%
ethyl acetoacetate
141-97-9

ethyl acetoacetate

benzaldehyde
100-52-7

benzaldehyde

urea
57-13-6

urea

ethyl 6-methyl-4-phenyl-3,4-dihydropyrimidin-2(1H)-one-5-carboxylate
123237-03-6, 5395-36-8

ethyl 6-methyl-4-phenyl-3,4-dihydropyrimidin-2(1H)-one-5-carboxylate

Conditions
ConditionsYield
With copper(II) bis(trifluoromethanesulfonate) In ethanol at 100℃; for 1h; Biginelli reaction; Microwave irradiation; Inert atmosphere;100%
With Cl7Fe2(1-)*C6H9N2O2(1+); C8H15N2(1+)*C4H12B(1-) at 80℃; for 2h; Reagent/catalyst; Biginelli Pyrimidone Synthesis;99%
With guanidine In neat (no solvent) at 80℃; for 2h; Biginelli Pyrimidone Synthesis;99%
ethyl acetoacetate
141-97-9

ethyl acetoacetate

benzaldehyde
100-52-7

benzaldehyde

Diethyl 2,6-dimethyl-4-phenyl-1,4-dihydropyridine-3,5-dicarboxylate
1165-06-6

Diethyl 2,6-dimethyl-4-phenyl-1,4-dihydropyridine-3,5-dicarboxylate

Conditions
ConditionsYield
With ammonia for 3h; Heating;100%
With C23H3BF16N2O; ammonium acetate In toluene at 100℃; for 10h; Hantzsch Dihydropyridine Synthesis;100%
With ammonium carbonate In water at 55 - 60℃; for 3.5h; Hantzsch pyridine synthesis;99%
1-amino-naphthalene
134-32-7

1-amino-naphthalene

benzaldehyde
100-52-7

benzaldehyde

N-benzylidenenaphthalen-1-amine
890-51-7

N-benzylidenenaphthalen-1-amine

Conditions
ConditionsYield
With aluminum oxide for 5h; Milling;100%
In water at 20℃; for 2h;80%
In dichloromethane for 10h; Reflux;70%
1.3-propanedithiol
109-80-8

1.3-propanedithiol

benzaldehyde
100-52-7

benzaldehyde

2-Phenyl-[1,3]dithiane
5425-44-5

2-Phenyl-[1,3]dithiane

Conditions
ConditionsYield
With boron trifluoride diethyl etherate at 23℃; for 3h;100%
With lithium tetrafluoroborate at 25℃; for 1h;100%
With lithium bromide at 75 - 80℃; for 0.25h;99%
propylamine
107-10-8

propylamine

benzaldehyde
100-52-7

benzaldehyde

N-benzylidenepropylamine
6852-55-7

N-benzylidenepropylamine

Conditions
ConditionsYield
In toluene for 1h; Ambient temperature;100%
at 26℃; for 24h;96%
With aluminum oxide at 20℃; for 4h;95%
n-butyllithium

n-butyllithium

benzaldehyde
100-52-7

benzaldehyde

1-Phenyl-1-pentanol
583-03-9

1-Phenyl-1-pentanol

Conditions
ConditionsYield
In tetrahydrofuran; hexane at -78 - 20℃;100%
Stage #1: n-butyllithium With mischmetall tribromide In tetrahydrofuran; hexane at -78℃; for 1h;
Stage #2: benzaldehyde In tetrahydrofuran; hexane at -78℃; for 3h; Imamoto reaction;
98%
In hexane at -78 - 20℃; for 1.16667h;95%
nitromethane
75-52-5

nitromethane

benzaldehyde
100-52-7

benzaldehyde

Conditions
ConditionsYield
palladium/alumina at 60℃; for 1h;100%
With 1-butyl-4-aza-1-azoniabicyclo[2.2.2]octane hydroxide In neat (no solvent) at 20℃; for 0.166667h; Reagent/catalyst; Henry Nitro Aldol Condensation; Green chemistry;99%
With 1-butyl-4-aza-1-azoniabicyclo[2.2.2]octane hydroxide In neat (no solvent) at 20℃; for 0.166667h; Catalytic behavior; Reagent/catalyst; Henry Nitro Aldol Condensation; Ionic liquid; Green chemistry;99%
hydrogen cyanide
74-90-8

hydrogen cyanide

benzaldehyde
100-52-7

benzaldehyde

(R)-Mandelonitrile
10020-96-9

(R)-Mandelonitrile

Conditions
ConditionsYield
With (R)-oxynitrilase (almond meal); citric buffer pH 5.5 In ethyl acetate at 4℃; for 48h; Product distribution; other aldehydes and methyl ketones, also in micro-aqueous phase, var temp. and solvents;100%
With (R)-oxynitrilase (almond meal) In ethyl acetate at 4℃; for 48h; 0.02 M citrate buffer pH 5.5;100%
With (R)-hydroxynitrile lyase In tert-butyl methyl ether; dimethyl sulfoxide at 5℃; for 24h; pH=4; aq. citrate buffer; Enzymatic reaction; optical yield given as %ee; enantioselective reaction;100%
(R,R)-2,3-butandiol
24347-58-8

(R,R)-2,3-butandiol

benzaldehyde
100-52-7

benzaldehyde

4,5-dimethyl-2-phenyl-(2α,4α,5β)-1,3-dioxolane
75281-80-0

4,5-dimethyl-2-phenyl-(2α,4α,5β)-1,3-dioxolane

Conditions
ConditionsYield
With toluene-4-sulfonic acid In benzene at 100℃; for 3h; Molecular sieve;100%
With trifluoromethanesulfonate; 1-phenyl-1-trimethylsilyloxyethane In dichloromethane at -20℃; for 3h;96%
With toluene-4-sulfonic acid; orthoformic acid triethyl ester at 140℃; for 2h;85%
hexan-1-amine
111-26-2

hexan-1-amine

benzaldehyde
100-52-7

benzaldehyde

Conditions
ConditionsYield
at 20℃; for 2h;100%
With ethanol; potassium carbonate
With aluminum oxide for 2h; Ambient temperature;
benzaldehyde
100-52-7

benzaldehyde

t-butyl 3-benzylidenecarbazate
24469-50-9

t-butyl 3-benzylidenecarbazate

Conditions
ConditionsYield
In tetrahydrofuran at 20℃; for 4h;100%
In ethanol for 3h; Reflux;100%
In ethanol99%
4,4'-thiobisaniline
139-65-1

4,4'-thiobisaniline

benzaldehyde
100-52-7

benzaldehyde

N,N'-(thiobis(4,1-phenylene))bis(1-phenyl methanimine)
3430-68-0

N,N'-(thiobis(4,1-phenylene))bis(1-phenyl methanimine)

Conditions
ConditionsYield
With piperidine In ethanol100%
With acetic acid In ethanol for 4h; Reflux;86%
With ethanol; zinc(II) chloride
phenyl carbamate
64-10-8

phenyl carbamate

benzaldehyde
100-52-7

benzaldehyde

1,1'-(phenylmethylene)bis(3-phenylurea)
40848-82-6

1,1'-(phenylmethylene)bis(3-phenylurea)

Conditions
ConditionsYield
In acetonitrile at 20℃; for 5h;100%
With silica-bonded N-(propylsulfonyl)piperazine-N-sulfamic acid In toluene for 2.5h; Reflux;78%
vinylmagnesium chloride
3536-96-7

vinylmagnesium chloride

benzaldehyde
100-52-7

benzaldehyde

1-Phenyl-2-propen-1-ol
4393-06-0

1-Phenyl-2-propen-1-ol

Conditions
ConditionsYield
In tetrahydrofuran at 0℃; for 2h; Inert atmosphere;100%
In tetrahydrofuran at -10 - 20℃; Schlenk technique;95%
In tetrahydrofuran at -10℃; for 2h; Inert atmosphere;93%
1-propynylmagnesium bromide
16466-97-0, 13254-27-8

1-propynylmagnesium bromide

benzaldehyde
100-52-7

benzaldehyde

1-phenylbut-2-yn-1-ol
32398-66-6

1-phenylbut-2-yn-1-ol

Conditions
ConditionsYield
In tetrahydrofuran100%
In tetrahydrofuran at 0 - 20℃;86%
In tetrahydrofuran at 0 - 20℃; for 2h; Grignard Reaction; Schlenk technique; Inert atmosphere;77%
l-cysteine hydrochloride
52-89-1

l-cysteine hydrochloride

benzaldehyde
100-52-7

benzaldehyde

(4R)-2-phenyl-1,3-thiazolidine-4-carboxylic acid
196930-46-8

(4R)-2-phenyl-1,3-thiazolidine-4-carboxylic acid

Conditions
ConditionsYield
Stage #1: l-cysteine hydrochloride With sodium hydroxide In water
Stage #2: benzaldehyde In ethanol; water at 20℃; for 3h;
100%
With potassium acetate In methanol; water at 0 - 25℃; for 6h;98%
Stage #1: l-cysteine hydrochloride With potassium carbonate In water
Stage #2: benzaldehyde In methanol; water at 25℃; for 3h;
98%
ethylmagnesium bromide
925-90-6

ethylmagnesium bromide

benzaldehyde
100-52-7

benzaldehyde

1-Phenyl-1-propanol
93-54-9

1-Phenyl-1-propanol

Conditions
ConditionsYield
With methylaluminum bis(2,6-di-tert-butylphenoxide) In diethyl ether; toluene at -78℃; for 2h;100%
In diethyl ether at 0 - 20℃;87%
Stage #1: ethylmagnesium bromide; benzaldehyde In tetrahydrofuran at 30℃; for 24h; Inert atmosphere;
Stage #2: With water In tetrahydrofuran Inert atmosphere;
73%
benzaldehyde
100-52-7

benzaldehyde

4-chloro-aniline
106-47-8

4-chloro-aniline

N-(4-chlorobenzylidene)aniline
780-21-2

N-(4-chlorobenzylidene)aniline

Conditions
ConditionsYield
With acetic acid In 1,2-dichloro-ethane at 20℃; for 24h; Inert atmosphere;100%
With aqueous extract of pericarp of Sapindus trifoliatus fruits at 20℃; for 0.0333333h;98%
sodium hydrogen sulfate; silica gel at 62 - 64℃; for 0.0208333h; microwave irradiation;96%
benzaldehyde
100-52-7

benzaldehyde

dimedone
126-81-8

dimedone

3,3,6,6-tetramethyl-9-phenyl-3,4,5,6,7,9-hexahydro-1H-xanthene-1,8-(2H)-dione
19744-83-3

3,3,6,6-tetramethyl-9-phenyl-3,4,5,6,7,9-hexahydro-1H-xanthene-1,8-(2H)-dione

Conditions
ConditionsYield
With poly[(2-acrylamido-2-methylpropane sulfonic acid)-co-(acrylic acid)-co-(vinyl functionalized halloysite clay)] In water at 20℃; for 3h;100%
With sulfated polyborate catalyst In neat (no solvent) at 100℃; for 0.05h; Catalytic behavior; Temperature; Green chemistry;99%
With acetic acid at 110℃; for 0.25h; Microwave irradiation;98%

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Ortho- and meta-nitrobenzaldehydes are two important intermediates in the chemical industry. They are the main products of benzaldehyde nitration by mixed acid, which is a hazardous chemical process since reaction rates are very sensitive to variations of the operating conditions. In the present...detailed

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100-52-7Relevant articles and documents

Synthesis of zeolite@metal-organic framework core-shell particles as bifunctional catalysts

Zhu, Guanghui,Graver, Richard,Emdadi, Laleh,Liu, Baoyu,Choi, Kyu Yong,Liu, Dongxia

, p. 30673 - 30676 (2014)

A zeolite@metal-organic framework (ZSM-5@UiO-66) core-shell composite has been synthesized for the first time by solvothermal growth of UiO-66 on the surface of ZSM-5 particles. The acidity from ZSM-5 and the basicity from the amine groups in UiO-66 obtai

-

Olah,Ho

, p. 610 (1976)

-

Linear free-energy relationships in chromium(VI) oxidation of substituted benzylamines in nonaqueous media

Thirumoorthi,Bhuvaneshwari,Elango

, p. 362 - 369 (2007)

The kinetics of oxidation of 11 para- and meta-substituted benzylamines by imidazolium fluorochromate (IFC) in different organic solvent media has been investigated in the presence of p-toluenesulfonic acid (TsOH). The reaction was run under pseudo-first-

Heterogeneous Permanganate Oxidations. 5. The Preparation of Aldehydes by Oxidative Cleavage of Carbon-Carbon Double Bonds

Lee, Donald G.,Chen, Tao,Wang, Zhao

, p. 2918 - 2919 (1993)

-

Conversion of acid chlorides to aldehydes by oxidation of alkoxyaluminum intermediates with pyridinium chlorochromate or pyridinium dichromate

Cha, Jin Soon,Kim, Jong Mi,Chun, Joong Hyun,Kwon, Oh Oun,Kwon, Sang Yong,Han, Sung Wook

, p. 204 - 207 (1999)

-

-

Leffingwell,Bluhm

, p. 1151 (1969)

-

A bifunctional approach towards the mild oxidation of organic halides: 2-dimethylamino-N,N-dimethylaniline N-oxide

Chandrasekhar, Sosale,Sridhar, Malayalam

, p. 5423 - 5425 (2000)

The titled reagent incorporates an oxygen-centred nucleophile and a basic moiety - in a suitably mutual orientation - in the same molecule. It oxidises various primary benzylic bromides to the corresponding aromatic aldehydes under relatively mild conditions (MeCN/rt-50°C/6-24 h) in high yields (83-97%), and is thus a useful alternative to the Kornblum procedure. (C) 2000 Elsevier Science Ltd.

Visible-light mediated C-C bond cleavage of 1,2-diols to carbonyls by cerium-photocatalysis

Schwarz, Johanna,K?nig, Burkhard

, p. 486 - 488 (2019)

We describe a photocatalytic method for the cleavage of vicinal diols to aldehydes and ketones. The reaction is catalyzed by blue light and a cerium-catalyst and the scope includes aryl as well as alkyl substituted diols. The simple protocol which works under air and at room temperature enables the valorization of abundant diols.

Synthesis, characterisation and catalytic activities of manganese(III) complexes of pyridoxal-based ONNO donor tetradenatate ligands

Maurya, Mannar R.,Saini, Priyanka,Haldar, Chanchal,Avecilla, Fernando

, p. 710 - 720 (2012)

Reaction of MnII(CH3COO)2 with dibasic tetradentate ligands, N,N′-ethylenebis(pyridoxylideneiminato) (H 2pydx-en, I), N,N′-propylenebis(pyridoxylideneiminato) (H 2pydx-1,3-pn, II) and 1-methyl-N,N′- ethylenebis(pyridoxylideneiminato) (H2pydx-1,2-pn, III) followed by aerial oxidation in the presence of LiCl gives complexes [MnIII(pydx- en)Cl(H2O)] (1) [MnIII(pydx-1,3-pn)Cl(CH3OH)] (2) and [MnIII(pydx-1,2-pn)Cl(H2O)] (3), respectively. Crystal and molecular structures of [Mn(pydx-en)Cl(H2O)] (1) and [Mn(pydx-1,3-pn)Cl(CH3OH)] (2) confirm their octahedral geometry and the coordination of ligands through ONNO(2-) form. Reaction of manganese(II)-exchanged zeolite-Y with these ligands in refluxing methanol followed by aerial oxidation in the presence of NaCl leads to the formation of the corresponding zeolite-Y encapsulated complexes, abbreviated herein as [MnIII(pydx-en)]-Y (4), [MnIII(pydx-1,3-pn)]-Y (5) and [MnIII(pydx-1,2-pn)]-Y (6). These encapsulated complexes are used as catalysts for the oxidation, by H2O2, of methyl phenyl sulfide, styrene and benzoin efficiently. Oxidation of methyl phenyl sulfide under the optimized reaction conditions gave ca. 86% conversion with two major products methyl phenyl sulfoxide and methyl phenyl sulfone in the ca. 70% and 30% selectivity, respectively. Oxidation of styrene catalyzed by these complexes gave at least five products namely styrene oxide, benzaldehyde, benzoic acid, 1-phenylethane-1,2-diol and phenylacetaldehyde with a maximum of 76.9% conversion of styrene by 4, 76.3% by 5 and 76.0% by 6 under optimized conditions. The selectivity of the obtained products followed the order: benzaldehyde > benzoic acid > styrene oxide > phenylacetaldehyde > 1-phenylethane-1,2-diol. Similarly, ca. 93% conversion of benzoin was obtained by these catalysts, where the selectivity of the products followed the order benzil > benzoic acid > benzaldehyde-dimethylacetal. Tests for the recyclability and heterogeneity of the reactions have also been carried. Neat complexes are equally active. However, the recycle ability of encapsulated complexes makes them better over neat ones.

Utilizing Benign Oxidants for Selective Aerobic Oxidations Using Heterogenized Platinum Nanoparticle Catalysts

Hinde, Christopher S.,Gill, Arran M.,Wells, Peter P.,Hor, T. S. Andy,Raja, Robert

, p. 1226 - 1230 (2015)

By using platinum nanoparticle catalysts that are generated in situ by extrusion from a porous copper chlorophosphate framework, the role of oxidants in the selective oxidation of benzyl alcohol to benzaldehyde was evaluated, with a view to establishing s

Mn(III) complexes with tridentate N,N,O-ligands as catalysts for the epoxidation of alkenes

Aghmiz,Mostfa,Iksi,Rivas,Gonzalez,Diaz,El Guemmout,El Laghdach,Echarri,Masdeu-Bulto

, p. 2567 - 2577 (2013)

Mn(III) complexes with tridentate Schiff bases have been prepared and applied as catalyst precursors in epoxidation of alkenes using iodosobenzene as an oxidant providing high conversions and high selectivities when cyclohexene derivatives were studied.

Oxidation of styrene oxide via chemical and photochemical methods using TiO2-CeO2-V2O5 catalysts

Castro, Laura V.,Manríquez, Ma. Elena,Ortiz-Islas, Emma,Pliego, Andrea Sánchez,Valdez, Martín Trejo

, (2020)

This work reports the preparation of the TiO2-CeO2 (TiCe) catalytic support of V2O5 catalysts, which was tested in the oxidation process of styrene oxide via chemical and photochemical methods. The TiCe-V2O5 catalytic support was prepared by the co-precipitated method from the individual metal oxides, varying the amount of vanadium oxide by 3, 6, and 10 % mol with respect to the support. The obtained catalysts were characterized by different spectroscopies, as well as by the N2 adsorption-desorption technique. The catalytic reaction test was carried out in the liquid phase during 120 min with/without ultraviolet light irradiation at 50 °C. There was no V2O5 effect on the surface area, pore volume, and pore diameter since all catalysts had similar textural values. In all samples the structures identified by X-ray diffraction were the Anatase phase and CeO2 in the cubic phase. XPS results revealed the formation of surface carbonate species, which were also identified by infrared spectroscopy. The conversion rate was better when employing ultraviolet light, and the rate increased as the V2O5 amount rose. The main reaction products were 2-phenylethanol and 1-phenylethanol. However, a low amount of benzaldehyde was detected. The selectivity to the desirable product (2-phenylethanol) increased when the reaction was irradiated with UV light and the catalyst contained a higher amount of vanadium. It was observed that the effect of UV radiation on the electric mobility produces an acceleration of the reaction to 2-phenylethanol, avoiding the 1-phenylethanol formation. The bandgap value decreased as the vanadium oxide amount increased, boosting the electric mobility.

Direct synthesis of carbonyl compounds from THP ethers with IBX in the presence of β-cyclodextrin in water

Narender,Reddy, M. Somi,Kumar, V. Pavan,Nageswar,Rao, K. Rama

, p. 1971 - 1973 (2005)

Water, an environmentally friendly reaction medium, has been utilized for the oxidative deprotection of tetrahydropyranyl ethers 1 with IBX at room temperature in the presence of β-cyclodextrin to give the corresponding carbonyl compounds 2.

RHODIUM(II) ACETATE: AN EFFECTIVE HOMOGENEOUS CATALYST FOR SELECTIVE ALLYLIC OXIDATION AND CARBON-CARBON BOND FISSION OF OLEFINS

Uemura, Sakae,Patil, Suresh R.

, p. 1743 - 1746 (1982)

Treatment of some cyclic olefins and allylbenzene with Rh2(OAc)4 in acetic acid in the presence of t-BuOOH gave the corresponding enones and allylic acetates, the former being predominant, Application to several styrene derivatives resulted in a selective C=C bond fission to give benzaldehyde or acetophenone.It is suggested that the reaction proceeds catalytically with Rh(II) acetate via an ionic pathway.

Disulfide-Catalyzed Visible-Light-Mediated Oxidative Cleavage of C=C Bonds and Evidence of an Olefin–Disulfide Charge-Transfer Complex

Deng, Yuchao,Wei, Xiao-Jing,Wang, Hui,Sun, Yuhan,No?l, Timothy,Wang, Xiao

, p. 832 - 836 (2017)

A photocatalytic method for the aerobic oxidative cleavage of C=C bonds has been developed. Electron-rich aromatic disulfides were employed as photocatalyst. Upon visible-light irradiation, typical mono- and multi-substituted aromatic olefins could be converted into ketones and aldehydes at ambient temperature. Experimental and computational studies suggest that a disulfide–olefin charge-transfer complex is possibly responsible for the unconventional dissociation of S?S bond under visible light.

Nitrogen kinetic isotope effects for the monoamine oxidase B-catalyzed oxidation of benzylamine and (1,1-2H2)benzylamine: Nitrogen rehybridization and CH bond cleavage are not concerted

MacMillar, Susanna,Edmondson, Dale E.,Matsson, Olle

, p. 12319 - 12321 (2011)

Nitrogen kinetic isotope effects for the oxidation of benzylamine and (1,1-2H2)benzylamine by recombinant human monoamine oxidase B show that cleavage of the CH bond is not concerted with rehybridization of the nitrogen atom.

Copper-Functionalized Metal–Organic Framework as Catalyst for Oxidant-Controlled Partial Oxidation of Cyclohexene

Chotmongkolsap, Pannapat,Bunchuay, Thanthapatra,Klysubun, Wantana,Tantirungrotechai, Jonggol

, p. 703 - 712 (2018)

Microwave irradiation is exploited for the facile, one-step functionalization of Cu(acac)2 to –NH2 pendant groups of MIL-53(Al)-NH2, a metal–organic framework material, under mild reaction conditions and a short reaction time. PXRD, XPS, XAS, and EPR spectroscopy are used to investigate the structure and chemical nature of the copper species on the framework. The copper center exists in the +2 oxidation state with a square-planar geometry and NO3 coordination environment. The copper complex is anchored to the framework by imine bond formation. This copper-functionalized MIL-53(Al)-NH2 or MIL-53[Cu] is employed in the catalytic oxidation of olefins using molecular oxygen (O2) or tert-butyl hydroperoxide (TBHP) as the oxidant. The chemoselectivities of the oxidation products depend on the type of oxidant and substrate. When O2 is used as the oxidant and isobutyraldehyde as the co-oxidant in the oxidation of cyclohexene with MIL-53[Cu], cyclohexene oxide is the major product. However, when TBHP is employed as the oxidant, 2-cyclohexen-1-one is the major product. Furthermore, the catalyst can be reused at least three times without a significant loss in activity.

Photochemical Electron-Transfer Reactions between Sulfides and Tetranitromethane. Oxidation vs Fragmentation of the Sulfide Radical-Cation Intermediate

Adam, Waldemar,Argueello, Juan E.,Penenory, Alicia B.

, p. 3905 - 3910 (1998)

Oxidation and/or fragmentation products are observed in the photochemical reaction of the alkyl phenyl sulfides 1a-d with tetranitromethane (TNM). The product distribution depends markedly on the substrate structure. Thus, methyl phenyl sulfide (1a) and benzyl phenyl sulfide (1b) give only the corresponding sulfoxides (oxidation). However, when the radical cation 1b?+ is generated by chemical oxidation with triarylaminium salts (Ar3N?+) in acetonitrile, in addition to oxidation fragmentation is also observed, and with an excess of Ar3N?+ oxidation is facilitated and no fragmentation is produced. For the photoreaction of diphenylmethyl phenyl sulfide (1c) with TNM, fragmentation is the main reaction, while for triphenylmethyl phenyl sulfide (1d) only this process is observed. The ease of C-S bond scission in these sulfur-centered radical cations 1.+ follows the ease of alkyl cation formation, i.e., Ph3C > Ph2CH > PhCH2 > CH3.

Selective activation of C-H bonds on the ring of ethylbenzene catalyzed by several diperoxovanadate complexes

Liu, Qiuyuan,Zhu, Liangfang,Li, Li,Guo, Bin,Hu, Xiaoke,Hu, Changwei

, p. 71 - 77 (2010)

The competitive oxidation of the C-H bonds on the aromatic ring and side-chain of ethylbenzene (EB) with hydrogen peroxide is investigated over four diperoxovanadate catalysts, that is, K3[VO(O2) 2(ox)] (bpV(ox)), K2

Double-helical ruthenium complexes of 2,2′:6′,2″,2?:6?,2″″-quinquepyridine (qpy) for multi-electron oxidation reactions

Ho, Paul Kwok-Keung,Cheung, Kung-Kai,Che, Chi-Ming

, p. 1197 - 1198 (1996)

Double-helical ruthenium complexes of 2,′:6′,2″:6″,2?:6?,2″″- quinquepyridine (qpy) are prepared from RuCl3·xH2O and qpy and the crystal structure of [Ru2(qPy)2(C2O4)][CF 3SOsub

Synergistic catalysis within TEMPO-functionalized periodic mesoporous organosilica with bridge imidazolium groups in the aerobic oxidation of alcohols

Karimi, Babak,Vahdati, Saleh,Vali, Hojatollah

, p. 63717 - 63723 (2016)

Anchoring 2,2,6,6-tetramethylpiperidine-1-oxyl radical (TEMPO) within the nanospaces of a periodic mesoporous organosilica with bridged imidazolium groups led to an unprecedented powerful bifunctional catalyst (TEMPO@PMO-IL-Br), which showed enhanced activity in the metal-free aerobic oxidation of alcohols. The catalyst and its precursors were characterized by N2 adsorption-desorption analysis, transmission electron microscopy (TEM), small angle X-ray scattering (SAXS), thermal gravimetric analysis (TGA), diffuse reflectance infrared Fourier transform spectroscopy (DRIFT), solid state electron paramagnetic resonance (EPR) spectroscopy, elemental analysis, transmission electron microscopy (TEM) and high resolution TEM. It was clearly found that the catalytic activity of SBA-15-functionalized TEMPO (TEMPO@SBA-15) not bearing IL, TEMPO@PMO-IL-Cl, PMO-IL-AMP, or individual catalytic functionalities (PMO-IL/TEMPO@SBA-15) was inferior as compared with those obtained from TEMPO@PMO-IL-Br in the metal-free aerobic oxidation of benzyl alcohol, suggesting the critical role of co-supported TEMPO and imidazolium bromide in obtaining high catalytic activity in the described catalyst system. Our observation clearly points to the fact that the combination of imidazolium bromide units in close proximity to TEMPO moieties in the nanospaces of TEMPO@PMO-IL-Br might be indeed one of the key factors explaining the enhanced catalytic activity observed for this catalyst in the oxidation of benzyl alcohol, possibly through a synergistic catalysis relay pathway. A proposed model was suggested for the observed synergistic effect.

Facile cleavage reactions of styrylic olefins using electrochemical methods

Maki, Shojiro,Niwa, Haruki,Hirano, Takashi

, p. 1385 - 1386 (1997)

Negative constant current electrolysis of styrylic olefins in an aqueous solvent resulted in the oxidative cleavage of the double bonds, giving carbonyl compounds in good yields. The double bond conjugated with more than one aromatic ring was selectively cleaved.

Triplet State and Photodecarboxylation of Phenylglyoxylic Acid in the Presence of Water

Kuhn, Hans Jochen,Goerner, Helmut

, p. 6208 - 6219 (1988)

The photodecarboxylation of phenylglyoxylic acid (PA) was studied by quantum yield (Φd) and time-resolved conductivity measurements in polar solvents at room temperature. Φd is substantial (>/=0.3) in the presence of 3-30 M water in acetonitrile and at pH a = 1.1 in neat water.The triplet states of PA, of its ethyl ester, and of 4-carboxybenzaldehyde were observed by nanosecond laser flash photolysis and emission spectroscopy.The initial transient obtained from PA (e.g., in acetonitrile λmax = 322 nm; lifetime >/= 3 μs) is assigned to the n,?* triplet state, and a second transient (in 2-propanol; λmax = 313 nm; t1/2 > 100 μs) is assigned to the Ph-COH-COOH radical.Phosphorescence was observed in glassy matrices at -196 deg C and in acetonitrile, acetone, and acetic acid at 25 deg C.In the latter ("inert") solvents the phosphorescence intensity and the triplet lifetime (up to 20 μs) are reduced by addition of alcohols or water.The rate constant of H-atom abstraction by triplet PA from 2-propanol is 1.5 * 106 M-1 s-1 in acetonitrile.Addition of water to PA in the "inert" solvents results in a non-Stern-Volmer behavior for triplet quenching.Excitation of PA in neat aqueous solution yields the triplet of benzaldehyde, the excited photoproduct, as main transient whereas triplet PA could not be detected.A mechanism accounting for the dependences of Φd on the pH and on the H2O concentration in mixtures with acetonitrile is proposed.Water governs the photochemistry of PA in three respects, via the acid-base equilibrium, as triplet quencher, and by reducing the quantum yield of intersystem crossing to the anion triplet.

A green and efficient oxidation of benzylic alcohols using H2O2 catalyzed by Montmorillonite-K10 supported MnCl2

Najafi, Gholam Reza

, p. 1162 - 1164 (2010)

Primary and secondary benzylic alcohols were oxidized to the corresponding carbonyl compounds in good to high yields by environmentally friendly and green oxidant, H2O2 catalyzed by Montmorillonite-K10 supported manganese(II) chlorid

Synthesis, structural characterization, and catalytic reactivity of a new molybdenum(VI) complex containing 1,3,4-thiadiazole derivative as a tridentate NNO donor ligand

Moradi-Shoeili, Zeinab,Zare, Maryam,Bagherzadeh, Mojtaba,Kubicki, MacIej,Boghaei, Davar M.

, p. 548 - 559 (2015)

A new cis-dioxo molybdenum(VI) complex was obtained by reaction of 2,4-dihydroxybenzylidene(5-N,N-methylphenylamino-1,3,4-thiadiazol-2-yl)hydrazone as ligand and [MoO2(acac)2] in methanol and was characterized by elemental analyses,

Functionalized-1,3,4-oxadiazole ligands for the ruthenium-catalyzed Lemieux-Johnson type oxidation of olefins and alkynes in water

Hkiri, Shaima,Touil, Soufiane,Samarat, Ali,Sémeril, David

, (2021/11/30)

Three arene-ruthenium(II) complexes bearing alkyloxy(5-phenyl-1,3,4-oxadiazol-2-ylamino)(4-trifluoromethylphenyl)methyl ligands were quantitatively obtained through the reaction of (E)-1-(4-trifluoromethylphenyl)-N-(5-phenyl-1,3,4-oxadiazol-2-yl)-methanimine with the ruthenium precursor [RuCl2(η6-p-cymene)]2 in a mixture of the corresponding alcohol and CH2Cl2 at 50 °C. The obtained complexes were fully characterized by elemental analysis, infrared, NMR and mass spectrometry. Solid-state structures confirmed the coordination of the 1,3,4-oxadiazole moiety to the ruthenium center via their electronically enriched nitrogen atom at position 3 in the aromatic ring. These complexes were evaluated as precatalysts in the Lemieux-Johnson type oxidative cleavage of olefins and alkynes in water at room temperature with NaIO4 as oxidizing agent. Good to full conversions of olefins into the corresponding aldehydes were measured, but low catalytic activity was observed in the case of alkynes. In order to get more insight into the mechanism, three analogue arene-ruthenium complexes were synthesized and tested in the oxidative cleavage of styrene. The latter tests clearly demonstrated the importance of the hemilabile alkyloxy groups, which may form more stable (N,O)-chelate intermediates and increase the efficiency of the cis-dioxo-ruthenium(VI) catalyst.

Efficient and selective oxidation of hydrocarbons with tert-butyl hydroperoxide catalyzed by oxidovanadium(IV) unsymmetrical Schiff base complex supported on γ-Fe2O3 magnetic nanoparticles

Ardakani, Mehdi Hatefi,Sabet, Mohammad,Samani, Mahnaz

, (2022/01/22)

The catalytic activity of an oxidovanadium(IV) unsymmetrical Schiff base complex supported on γ-Fe2O3 magnetic nanoparticles, γ-Fe2O3@[VO(salenac-OH)] in which salenac-OH = [9-(2′,4′-dihydroxyphenyl)-5,8-diaza-4

Selective catalytic synthesis of bio-based high value chemical of benzoic acid from xylan with Co2MnO4@MCM-41 catalyst

Fan, Minghui,He, Yuting,Li, Quanxin,Luo, Yuehui,Yang, Mingyu,Zhang, Yanhua,Zhu, Lijuan

, (2021/12/20)

The efficient synthesis of bio-based chemicals using renewable carbon resources is of great significance to promote sustainable chemistry and develop green economy. This work aims to demonstrate that benzoic acid, an important high added value chemical in petrochemical industry, can be selectively synthesized using xylan (a typical model compound of hemicellulose). This novel controllable transformation process was achieved by selective catalytic pyrolysis of xylan and subsequent catalytic oxidation. The highest benzoic acid selectivity of 88.3 % with 90.5 % conversion was obtained using the 10wt%Co2MnO4@MCM-41 catalyst under the optimized reaction conditions (80 °C, 4 h). Based on the study of the model compounds and catalyst's characterizations, the reaction pathways for the catalytic transformation of xylan to bio-based benzoic acid were proposed.