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122-03-2

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122-03-2 Usage

Chemical Properties

Different sources of media describe the Chemical Properties of 122-03-2 differently. You can refer to the following data:
1. clear colorless to yellow liquid
2. Cuminaldehyde has a strong, pungent, cumin-like odor and similar taste.

Occurrence

Reported in a large number of essential oils, cumin, Acacia farnesiana, cinnamon, bitter orange, Mexican lime, Eucalyptus globulus, rue, boldus, Artemisia hausiliensis and others. Also reported in lemon and mandarin peel oil, cinnamon bark, anise, clove bud, cumin seed, turmeric, parsley, calabash nutmeg (Monodora myristica Dunal), angelica root, thyme, beef, brandy, grape and mastic gum fruit oil.

Uses

Different sources of media describe the Uses of 122-03-2 differently. You can refer to the following data:
1. Cuminaldehyde is a flavoring agent that is a liquid, colorless to yellow in appearance, with a strong pungent odor resembling cumin oil. It is insoluble in water and soluble in alcohol and ether. It is obtained from cumin oil. It is also termed p-, cumaldehyde, and cuminal.
2. Cuminaldehyde has been used to study larvicidal and adulticidal toxicity of monoterpenes against Culex pipiens. It has been used in evaluation of chemical composition, antimicrobial and antioxidant activities of essential oil and various extracts of Eucalyptus gilii.

Definition

ChEBI: A member of the class of benzaldehydes that is benzaldehyde substituted by an isopropyl group at position 4. It is a component of essential oils from Cumin and exhibits insecticidal activities.

Preparation

From p-isopropylbenzyl chloride and hexamethylenetetramine (Arctander, 1969).

Taste threshold values

Taste characteristics at 10 ppm: spicy with green cumin and herbal nuances.

General Description

Cuminaldehyde is a constituent of cumin oil that exhibits strong antifungal and antibacterial activities.

Biochem/physiol Actions

Cuminaldehyde increases the insulin secretion in streptozotocin-induced diabetic rats. It suppresses melanin formation in cultured murine B16-F10 melanoma cells.

Safety Profile

Moderately toxic by ingestion and skin contact. A skin irritant. Combustible liquid. When heated to decomposition it emits acrid smoke and irritating fumes. See also ALDEHYDES.

Synthesis

Prepared synthetically by heating p-isopropyl benzoyl chloride with an aqueous or alcoholic hexamethylenetetraamine solution.

Purification Methods

A likely impurity is the benzoic acid. Check the IR for the presence of OH from CO2H, and the CO frequencies. If the acid is present, then dissolve the aldehyde in Et2O, wash it with 10% NaHCO3 until effervescence ceases, then with brine, dry over CaCl2, evaporate and distil the residual oil, preferably under vacuum. It is almost insoluble in H2O, but soluble in EtOH and Et2O. The thiosemicarbazone has m 147o after recrystallisation from aqueous EtOH, MeOH or *C6H6. [Crounse J Am Chem Soc 71 1263 1949, Bernstein et al. J Am Chem Soc 73 906 1951, Gensler & Berman J Am Chem Soc 80 4949 1958, Beilstein 7 H 318, 7 II 347, 7 III 1095, 7 IV 723.]

Check Digit Verification of cas no

The CAS Registry Mumber 122-03-2 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,2 and 2 respectively; the second part has 2 digits, 0 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 122-03:
(5*1)+(4*2)+(3*2)+(2*0)+(1*3)=22
22 % 10 = 2
So 122-03-2 is a valid CAS Registry Number.

122-03-2 Well-known Company Product Price

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  • (Code)Product description
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  • TCI America

  • (I0168)  Cuminaldehyde  >97.0%(GC)

  • 122-03-2

  • 25g

  • 170.00CNY

  • Detail
  • TCI America

  • (I0168)  Cuminaldehyde  >97.0%(GC)

  • 122-03-2

  • 500g

  • 1,140.00CNY

  • Detail
  • Alfa Aesar

  • (A14019)  4-Isopropylbenzaldehyde, tech. 90%   

  • 122-03-2

  • 25g

  • 227.0CNY

  • Detail
  • Alfa Aesar

  • (A14019)  4-Isopropylbenzaldehyde, tech. 90%   

  • 122-03-2

  • 100g

  • 454.0CNY

  • Detail
  • Alfa Aesar

  • (A14019)  4-Isopropylbenzaldehyde, tech. 90%   

  • 122-03-2

  • 500g

  • 986.0CNY

  • Detail

122-03-2SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name cuminaldehyde

1.2 Other means of identification

Product number -
Other names Cuminaldehyde

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Fragrances
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:122-03-2 SDS

122-03-2Synthetic route

cuminol
536-60-7

cuminol

(4-isopropylbenzaldehyde)
122-03-2

(4-isopropylbenzaldehyde)

Conditions
ConditionsYield
With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; oxygen In dichloromethane; water under 760.051 Torr; for 2h; Green chemistry;100%
With dmap; C25H30F17N5O4S(1-)*K(1+); oxygen; copper(II) sulfate In water at 25℃; for 2h; chemoselective reaction;99%
With titanium(IV) oxide; oxygen at 29.84℃; under 760.051 Torr; for 6h; Sealed tube; Irradiation;99%
isopropyllithium
1888-75-1

isopropyllithium

4-bromo-benzaldehyde
1122-91-4

4-bromo-benzaldehyde

(4-isopropylbenzaldehyde)
122-03-2

(4-isopropylbenzaldehyde)

Conditions
ConditionsYield
Stage #1: 4-bromo-benzaldehyde With bis(tri-tert-butylphosphine)palladium(0); sodium chloride In water at 20℃; for 0.166667h; Negishi Coupling; Schlenk technique;
Stage #2: isopropyllithium With zinc(II) chloride In 2-methyltetrahydrofuran; water at 10℃; for 0.00555556h; Schlenk technique; chemoselective reaction;
98%
4-isopropylbenzaldehyde oxime
3717-17-7, 3717-18-8, 13372-80-0

4-isopropylbenzaldehyde oxime

(4-isopropylbenzaldehyde)
122-03-2

(4-isopropylbenzaldehyde)

Conditions
ConditionsYield
With iron(III) chloride; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; oxygen In water; toluene at 60℃; under 760.051 Torr; for 4h;95%
With tungsten(VI) chloride; zinc In acetonitrile at 20℃; for 0.333333h;92%
2-(4-isopropylphenyl)-1,3-dithiane

2-(4-isopropylphenyl)-1,3-dithiane

(4-isopropylbenzaldehyde)
122-03-2

(4-isopropylbenzaldehyde)

Conditions
ConditionsYield
With 1,3,5-trichloro-2,4,6-triazine; dimethyl sulfoxide In dichloromethane at 20℃; for 1h;94%
2-(4-isopropylphenyl)-1,3-dithiolane
23229-31-4

2-(4-isopropylphenyl)-1,3-dithiolane

(4-isopropylbenzaldehyde)
122-03-2

(4-isopropylbenzaldehyde)

Conditions
ConditionsYield
With 1,3,5-trichloro-2,4,6-triazine; dimethyl sulfoxide In dichloromethane at 20℃; for 2.45h;93%
With Oxone; potassium bromide In water; acetonitrile at 20℃; for 0.333333h;92%
With iodosylbenzene In dichloromethane at 20℃; for 0.25h;91%
4-isopropylstyrene
2055-40-5

4-isopropylstyrene

(4-isopropylbenzaldehyde)
122-03-2

(4-isopropylbenzaldehyde)

Conditions
ConditionsYield
With dihydrogen peroxide In acetonitrile at 65℃; for 6h;93%
With sodium periodate In water; ethyl acetate; acetonitrile at 0℃; for 3.5h;63%
Stage #1: 4-isopropylstyrene With BO40W12(5-)*2C12H12N6*Co(2+)*3H(1+)*10H2O In acetonitrile for 0.0833333h;
Stage #2: With dihydrogen peroxide In acetonitrile at 70℃; for 7h;
4-isopropylbenzyl chloride
2051-18-5

4-isopropylbenzyl chloride

(4-isopropylbenzaldehyde)
122-03-2

(4-isopropylbenzaldehyde)

Conditions
ConditionsYield
With potassium hydroxide; cetyltrimethylammonim bromide; potassium nitrate In water for 4h; pH=10 - 11; Reflux;92%
With 4Na(1+)*6H(1+)*NiMo6O24(10-)=Na4H6NiMo6O24; oxygen In water; acetonitrile at 20℃; under 760.051 Torr; for 12h; Irradiation;92%
With potassium nitrite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; oxygen; potassium bromide In water for 5h; Reflux;89%
4-i-propylbenzyl bromide
73789-86-3

4-i-propylbenzyl bromide

(4-isopropylbenzaldehyde)
122-03-2

(4-isopropylbenzaldehyde)

Conditions
ConditionsYield
With potassium nitrite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; oxygen In water for 4h; Reflux;92%
Multi-step reaction with 2 steps
1: eosin y; oxygen / dimethyl sulfoxide / 12 h / 25 °C / Irradiation
2: eosin y / dimethyl sulfoxide / 24 h / 80 °C / Irradiation
View Scheme
4-bromo-benzaldehyde
1122-91-4

4-bromo-benzaldehyde

isopropyl zinc bromide
77047-87-1

isopropyl zinc bromide

(4-isopropylbenzaldehyde)
122-03-2

(4-isopropylbenzaldehyde)

Conditions
ConditionsYield
Stage #1: 4-bromo-benzaldehyde With C40H55Cl5N3Pd In toluene at 0℃; for 0.0833333h; Negishi Coupling; Inert atmosphere; Cooling with ice;
Stage #2: isopropyl zinc bromide In tetrahydrofuran; toluene at 23℃; for 0.5h; Inert atmosphere;
92%
With dichloro(1,3-bis(2,6-bis(3-pentyl)phenyl)imidazolin-2-ylidene)(3-chloropyridyl)palladium(II) In tetrahydrofuran; toluene at 0 - 20℃; for 3h; Negishi coupling reaction; Inert atmosphere;78%
tert-butyl-(4-isopropyl-benzyloxy)-dimethyl-silane

tert-butyl-(4-isopropyl-benzyloxy)-dimethyl-silane

(4-isopropylbenzaldehyde)
122-03-2

(4-isopropylbenzaldehyde)

Conditions
ConditionsYield
With N-hydroxyphthalimide; oxygen; cobalt(II) benzoate In acetonitrile at 20℃; for 0.666667h;90%
1,1-diacetoxy-1-(4-i-propylphenyl)methane
7154-10-1

1,1-diacetoxy-1-(4-i-propylphenyl)methane

(4-isopropylbenzaldehyde)
122-03-2

(4-isopropylbenzaldehyde)

Conditions
ConditionsYield
With saccharin sulfonic acid at 90℃; for 0.0333333h; Neat (no solvent);90%
With water at 20℃; for 0.166667h; Green chemistry;96 %Chromat.
2-(4-isopropyl-phenyl)-[1,3]oxathiolane
23229-35-8

2-(4-isopropyl-phenyl)-[1,3]oxathiolane

(4-isopropylbenzaldehyde)
122-03-2

(4-isopropylbenzaldehyde)

Conditions
ConditionsYield
With Iron(III) nitrate nonahydrate at 90℃; for 0.05h;90%
4-iso-propylbenzyl trimethylsilyl ether
71700-48-6

4-iso-propylbenzyl trimethylsilyl ether

(4-isopropylbenzaldehyde)
122-03-2

(4-isopropylbenzaldehyde)

Conditions
ConditionsYield
With N-hydroxyphthalimide; oxygen; cobalt(II) benzoate In acetonitrile at 20℃; for 0.333333h;89%
With silica chromate; silica gel In dichloromethane at 20℃; for 0.666667h;82%
2-(4-Isopropylbenzyloxy)-tetrahydropyran
394738-99-9

2-(4-Isopropylbenzyloxy)-tetrahydropyran

(4-isopropylbenzaldehyde)
122-03-2

(4-isopropylbenzaldehyde)

Conditions
ConditionsYield
With 1,4-dichloro-1,4-diazoniabicyclo[2,2,2]octane bis-chloride In water at 50℃; for 0.25h; pH=7;88%
1-(4-isopropylphenyl)ethanol
1475-10-1

1-(4-isopropylphenyl)ethanol

A

4-Isopropylbenzoic acid
536-66-3

4-Isopropylbenzoic acid

B

(4-isopropylbenzaldehyde)
122-03-2

(4-isopropylbenzaldehyde)

Conditions
ConditionsYield
With sodium nitrate; water; oxygen In dimethyl sulfoxide at 130℃; for 24h;A 88%
B 8%
4-isopropylbenzylamine
4395-73-7

4-isopropylbenzylamine

(4-isopropylbenzaldehyde)
122-03-2

(4-isopropylbenzaldehyde)

Conditions
ConditionsYield
With immobilised amine transaminase from the moderate halophilic bacterium Halomonas elongata; sodium pyruvate In aq. phosphate buffer; dimethyl sulfoxide at 37℃; under 760.051 Torr; for 5h; pH=8;84%
4-i-propylbenzyl bromide
73789-86-3

4-i-propylbenzyl bromide

A

(4-isopropylbenzaldehyde)
122-03-2

(4-isopropylbenzaldehyde)

B

cuminol
536-60-7

cuminol

Conditions
ConditionsYield
With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; oxygen In water for 4h; Reflux;A 19%
B 76%
4-isopropylbenzyl chloride
2051-18-5

4-isopropylbenzyl chloride

A

4-Isopropylbenzoic acid
536-66-3

4-Isopropylbenzoic acid

B

(4-isopropylbenzaldehyde)
122-03-2

(4-isopropylbenzaldehyde)

Conditions
ConditionsYield
With potassium hydroxide; cetyltrimethylammonim bromide; potassium nitrate In water for 4h; pH=10 - 11; Reflux;A 2 g
B 71%
Isopropylbenzene
98-82-8

Isopropylbenzene

carbon dioxide
124-38-9

carbon dioxide

(4-isopropylbenzaldehyde)
122-03-2

(4-isopropylbenzaldehyde)

Conditions
ConditionsYield
Stage #1: carbon dioxide With zinc(II) cyanide; ruthenium trichloride; rhodium (III) acetate; cobalt(II) acetate; zirconium(IV) acetate for 1h; Autoclave;
Stage #2: Isopropylbenzene at 50℃; under 15001.5 Torr; for 5h;
70.2%
4-isopropylbenzaldehyde oxime
3717-17-7, 3717-18-8, 13372-80-0

4-isopropylbenzaldehyde oxime

A

p-Cyanocumen
13816-33-6

p-Cyanocumen

B

(4-isopropylbenzaldehyde)
122-03-2

(4-isopropylbenzaldehyde)

Conditions
ConditionsYield
With pyridine; N-chloro-succinimide In acetonitrile at 20℃;A 70%
B n/a
(4-isopropylphenyl)acetic acid
4476-28-2

(4-isopropylphenyl)acetic acid

A

1-(fluoromethyl)-4-isopropylbenzene
477219-29-7

1-(fluoromethyl)-4-isopropylbenzene

B

(4-isopropylbenzaldehyde)
122-03-2

(4-isopropylbenzaldehyde)

Conditions
ConditionsYield
With xenon fluoride In dichloromethane at 20℃; for 14 - 18h; Inert atmosphere;A 67%
B 10%
isopropylboronic acid
80041-89-0

isopropylboronic acid

4-(trifluormethanesulfonyloxy)benzaldehyde
17763-69-8

4-(trifluormethanesulfonyloxy)benzaldehyde

(4-isopropylbenzaldehyde)
122-03-2

(4-isopropylbenzaldehyde)

Conditions
ConditionsYield
With potassium phosphate; C20H34O3P2; [Pd(cinnamyl)Cl]2 In toluene at 110℃; for 12h; Suzuki-Miyaura Coupling; Inert atmosphere;67%
4-methylisopropylbenzene
99-87-6

4-methylisopropylbenzene

A

(4-Isopropyl-phenyl)-nitromethan
33241-77-9

(4-Isopropyl-phenyl)-nitromethan

B

4-isopropylbenzyl nitrate
95543-77-4

4-isopropylbenzyl nitrate

C

para-methylacetophenone
122-00-9

para-methylacetophenone

D

(4-isopropylbenzaldehyde)
122-03-2

(4-isopropylbenzaldehyde)

Conditions
ConditionsYield
With ammonium cerium(IV) nitrate In acetonitrile at 17℃; for 0.666667h; Irradiation;A 3%
B 62%
C 6%
D 6%
With ammonium cerium(IV) nitrate In acetonitrile at 17℃; for 0.666667h; Irradiation; Further byproducts given;A 3%
B 62%
C 6%
D 6%
2-hydroxy-2-(4-isopropylphenyl)acetonitrile
91132-18-2

2-hydroxy-2-(4-isopropylphenyl)acetonitrile

A

4-Isopropylbenzoic acid
536-66-3

4-Isopropylbenzoic acid

B

(4-isopropylbenzaldehyde)
122-03-2

(4-isopropylbenzaldehyde)

Conditions
ConditionsYield
Stage #1: 2-hydroxy-2-(4-isopropylphenyl)acetonitrile With (η(6)-benzene)chloro[1,2-bis(diphenylphosphino)ethane]ruthenium(II) chloride In benzene at 120℃; for 24h; Inert atmosphere; Schlenk technique;
Stage #2: With water In dichloromethane; ethyl acetate; benzene for 24h;
A 58%
B 36%
4-isopropyl-1-cyclopropylbenzene
27546-49-2

4-isopropyl-1-cyclopropylbenzene

A

(E)-3-(4-isopropylphenyl)acrylaldehyde
86604-05-9

(E)-3-(4-isopropylphenyl)acrylaldehyde

B

5-(4-isopropylphenyl)isoxazoline
119200-34-9

5-(4-isopropylphenyl)isoxazoline

C

(4-isopropylbenzaldehyde)
122-03-2

(4-isopropylbenzaldehyde)

Conditions
ConditionsYield
With dinitrogen tetraoxide; triethylamine In dichloromethane at -30℃; for 1h;A 28%
B 50%
C 7%
With dinitrogen tetraoxide In pentane at -30℃; for 6h;A 41%
B 40%
C 10%
With dinitrogen tetraoxide In pentane at -30℃; for 6h;A 40%
B 40%
C 10%
With dinitrogen tetraoxide In dichloromethane at -30℃; for 1h;A 39%
B 40%
C 8%
4-methylisopropylbenzene
99-87-6

4-methylisopropylbenzene

A

1-methyl-4-isopropenylbenzene
1195-32-0

1-methyl-4-isopropenylbenzene

B

2-(4-isopropylbenzyl)-1,4-benzoquinone
69897-58-1

2-(4-isopropylbenzyl)-1,4-benzoquinone

C

4-(2-hydroxy-2-propyl)benzene-1-carbaldehyde
81036-81-9

4-(2-hydroxy-2-propyl)benzene-1-carbaldehyde

D

(4-isopropylbenzaldehyde)
122-03-2

(4-isopropylbenzaldehyde)

Conditions
ConditionsYield
With sodium persulfate; sulfuric acid; silver nitrate; p-benzoquinone In water at 60℃; for 0.5h;A 5%
B 45%
C 10%
D 20%
4-methylisopropylbenzene
99-87-6

4-methylisopropylbenzene

A

2-(4-isopropylbenzyl)-1,4-benzoquinone
69897-58-1

2-(4-isopropylbenzyl)-1,4-benzoquinone

B

4-(2-hydroxy-2-propyl)benzene-1-carbaldehyde
81036-81-9

4-(2-hydroxy-2-propyl)benzene-1-carbaldehyde

C

(4-isopropylbenzaldehyde)
122-03-2

(4-isopropylbenzaldehyde)

D

cuminol
536-60-7

cuminol

Conditions
ConditionsYield
With sodium persulfate; sulfuric acid; silver nitrate; p-benzoquinone In water at 60℃; for 0.5h; Further byproducts given;A 45%
B 10%
C 20%
D 5%
4-methylisopropylbenzene
99-87-6

4-methylisopropylbenzene

p-benzoquinone
106-51-4

p-benzoquinone

A

2-(4-isopropylbenzyl)-1,4-benzoquinone
69897-58-1

2-(4-isopropylbenzyl)-1,4-benzoquinone

B

4-(2-hydroxy-2-propyl)benzene-1-carbaldehyde
81036-81-9

4-(2-hydroxy-2-propyl)benzene-1-carbaldehyde

C

(4-isopropylbenzaldehyde)
122-03-2

(4-isopropylbenzaldehyde)

D

cuminol
536-60-7

cuminol

Conditions
ConditionsYield
With sodium persulfate; sulfuric acid; silver nitrate In water at 60℃; for 0.5h; Further byproducts given;A 45%
B 10%
C 20%
D 5%
Isopropylbenzene
98-82-8

Isopropylbenzene

tris(diformylamino)methane
332047-72-0

tris(diformylamino)methane

(4-isopropylbenzaldehyde)
122-03-2

(4-isopropylbenzaldehyde)

Conditions
ConditionsYield
Stage #1: Isopropylbenzene; tris(diformylamino)methane With aluminium trichloride In 1,2-dichloro-ethane at -13 - -1℃; for 14h;
Stage #2: With water
38%
With aluminium trichloride In 1,2-dichloro-ethane at -13 - -1℃; for 14h;38%
(4-isopropylbenzaldehyde)
122-03-2

(4-isopropylbenzaldehyde)

4-isopropylbenzaldehyde oxime
3717-17-7, 3717-18-8, 13372-80-0

4-isopropylbenzaldehyde oxime

Conditions
ConditionsYield
With hydroxylamine hydrochloride; sodium acetate In ethanol; water Reflux;100%
With hydroxylamine hydrochloride; sodium carbonate In methanol; water at 20℃; for 19.5h;99%
With bismuth(lll) trifluoromethanesulfonate; acetylhydroxamic acid In methanol for 24h; Reflux;97%
cis, trans-1,3-dimethylaminocyclohexane
2579-20-6

cis, trans-1,3-dimethylaminocyclohexane

(4-isopropylbenzaldehyde)
122-03-2

(4-isopropylbenzaldehyde)

C28H38N2
1217526-87-8

C28H38N2

Conditions
ConditionsYield
In methanol at 20℃; Molecular sieve;100%
In methanol at 20℃; Molecular sieve;
propylamine
107-10-8

propylamine

(4-isopropylbenzaldehyde)
122-03-2

(4-isopropylbenzaldehyde)

C13H19N
100617-19-4

C13H19N

Conditions
ConditionsYield
at 20℃; for 12h;100%
1.3-propanedithiol
109-80-8

1.3-propanedithiol

(4-isopropylbenzaldehyde)
122-03-2

(4-isopropylbenzaldehyde)

2-(4-isopropylphenyl)-1,3-dithiane

2-(4-isopropylphenyl)-1,3-dithiane

Conditions
ConditionsYield
With 1-methyl-3-octylimidazolium hydrogen sulfate ionic liquid [OMIm]HSO4 inside the mesochannels of SBA-15-Pr-SO3H In neat (no solvent) at 20℃; for 2h; chemoselective reaction;100%
With oxygen In acetonitrile at 20℃; for 24h; Irradiation; Green chemistry; chemoselective reaction;95%
With cobalt(II) chloride In acetonitrile at 20℃;93%
With boron trifluoride diethyl etherate In dichloromethane Inert atmosphere;
C17H25NO3

C17H25NO3

(4-isopropylbenzaldehyde)
122-03-2

(4-isopropylbenzaldehyde)

C27H36N2O2

C27H36N2O2

Conditions
ConditionsYield
With ammonium acetate In ethanol at 20℃; for 17h; Inert atmosphere;100%
C21H27NO3

C21H27NO3

(4-isopropylbenzaldehyde)
122-03-2

(4-isopropylbenzaldehyde)

C31H38N2O2

C31H38N2O2

Conditions
ConditionsYield
With ammonium acetate In ethanol at 60℃; Inert atmosphere; Sealed tube;100%
C21H28FNO3

C21H28FNO3

(4-isopropylbenzaldehyde)
122-03-2

(4-isopropylbenzaldehyde)

C31H37FN2O2

C31H37FN2O2

Conditions
ConditionsYield
With ammonium acetate In ethanol at 20℃; for 16h; Inert atmosphere; Sealed tube;100%
ethylenediamine
107-15-3

ethylenediamine

(4-isopropylbenzaldehyde)
122-03-2

(4-isopropylbenzaldehyde)

N,N‐bis(4‐isopropylbenzylidene)ethane‐1,2‐diamine

N,N‐bis(4‐isopropylbenzylidene)ethane‐1,2‐diamine

Conditions
ConditionsYield
In ethanol at 20℃; for 6h;99%
In methanol for 6h;92%
In ethanol at 40℃; for 10h;80%
at 120℃;
In methanol Inert atmosphere;
(4-isopropylbenzaldehyde)
122-03-2

(4-isopropylbenzaldehyde)

4-Isopropylbenzoic acid
536-66-3

4-Isopropylbenzoic acid

Conditions
ConditionsYield
With C4H11FeMo6NO24(3-)*3C16H36N(1+); water; oxygen; sodium carbonate at 50℃; under 760.051 Torr; for 8h; Green chemistry;99%
With 4H3N*4H(1+)*CuMo6O18(OH)6(4-); water; oxygen; sodium carbonate at 50℃; under 760.051 Torr; for 12h;99%
With tris[2-(4,6-difluorophenyl)pyridinato-C2,N]-iridium(III); oxygen In acetonitrile at 20℃; Irradiation; Sealed tube; Green chemistry; chemoselective reaction;95%
acetone
67-64-1

acetone

(4-isopropylbenzaldehyde)
122-03-2

(4-isopropylbenzaldehyde)

(E)-4-(4-isopropylphenyl)but-3-en-2-one
74389-78-9, 81467-89-2

(E)-4-(4-isopropylphenyl)but-3-en-2-one

Conditions
ConditionsYield
With sodium hydroxide In water at 20℃; for 6h; Claisen-Schmidt Condensation;99%
With sodium hydroxide In water at 25℃; for 18h;41%
With sodium hydroxide In water Ambient temperature;16%
With sodium hydroxide In water at 25℃; for 12h;
With sodium hydroxide at 20℃; for 24h; Claisen-Schmidt Condensation;
cycl-isopropylidene malonate
2033-24-1

cycl-isopropylidene malonate

(4-isopropylbenzaldehyde)
122-03-2

(4-isopropylbenzaldehyde)

3-(p-isopropylphenyl)propionic acid
58420-21-6

3-(p-isopropylphenyl)propionic acid

Conditions
ConditionsYield
Stage #1: cycl-isopropylidene malonate; (4-isopropylbenzaldehyde) With formic acid; triethylamine In N,N-dimethyl-formamide at 0 - 80℃; for 14h;
Stage #2: With hydrogenchloride; water In N,N-dimethyl-formamide pH=1 - 2;
99%
ethyl acetoacetate
141-97-9

ethyl acetoacetate

(4-isopropylbenzaldehyde)
122-03-2

(4-isopropylbenzaldehyde)

malononitrile
109-77-3

malononitrile

6-amino-2,4-dihydro-4-(4-isopropylphenyl)-3-methylpyrano[2,3-c]pyrazole-5-carbonitrile
326915-75-7, 340812-03-5

6-amino-2,4-dihydro-4-(4-isopropylphenyl)-3-methylpyrano[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%
With hydrazine hydrate; 2-amino-2-hydroxymethyl-1,3-propanediol In ethanol; water at 20℃; for 2.5h; Green chemistry;84%
(4-isopropylbenzaldehyde)
122-03-2

(4-isopropylbenzaldehyde)

malononitrile
109-77-3

malononitrile

β,β-dicyano-4-isopropylstyrene
26088-83-5

β,β-dicyano-4-isopropylstyrene

Conditions
ConditionsYield
With Zn(N4,N4'-di(pyridin-4-yl)biphenyl-4,4'-dicarboxamide)(5-aminoisophthalate) In neat (no solvent) for 4h; Knoevenagel Condensation;99%
With 1-butyl-1,2,4-triazolium tetrafluoroborate In ethanol; water at 70℃; for 0.25h; Reagent/catalyst; Knoevenagel Condensation;92%
With tin dioxide In neat (no solvent) at 20℃; Knoevenagel Condensation; Green chemistry;90%
2-Hydroxy-1,4-naphthoquinone
83-72-7

2-Hydroxy-1,4-naphthoquinone

1,3-cylohexanedione
504-02-9

1,3-cylohexanedione

(4-isopropylbenzaldehyde)
122-03-2

(4-isopropylbenzaldehyde)

C26H22O4

C26H22O4

Conditions
ConditionsYield
With silica-supported tungstic acid In neat (no solvent) at 60℃; for 0.0666667h; Sonication; Green chemistry;99%
(4-isopropylbenzaldehyde)
122-03-2

(4-isopropylbenzaldehyde)

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

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

2-((4-isopropylbenzyl)oxy)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

2-((4-isopropylbenzyl)oxy)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Conditions
ConditionsYield
With C34H28N6Zn In neat (no solvent) at 20℃; for 1h; Glovebox; Schlenk technique;99%
With C24H34N5PSeTi In neat (no solvent) at 30℃; for 2h; Glovebox; Schlenk technique; chemoselective reaction;96%
With [{2-(AdN=CH)–C4H3NK(THF)}n] at 30℃; for 1h; Inert atmosphere; Glovebox; Schlenk technique;92 %Spectr.
triethylsilane
617-86-7

triethylsilane

(4-isopropylbenzaldehyde)
122-03-2

(4-isopropylbenzaldehyde)

triethyl((4-isopropylbenzyl)oxy)silane
53172-95-5

triethyl((4-isopropylbenzyl)oxy)silane

Conditions
ConditionsYield
With C42H43BN3P2(1+)*C18HBF15(1-) In chloroform at 40℃; for 1h; Reagent/catalyst; Temperature; Schlenk technique; Glovebox;99%
ethane-1,2-dithiol
540-63-6

ethane-1,2-dithiol

(4-isopropylbenzaldehyde)
122-03-2

(4-isopropylbenzaldehyde)

2-(4-isopropylphenyl)-1,3-dithiolane
23229-31-4

2-(4-isopropylphenyl)-1,3-dithiolane

Conditions
ConditionsYield
at 20℃;99%
1-methylindole
603-76-9

1-methylindole

(4-isopropylbenzaldehyde)
122-03-2

(4-isopropylbenzaldehyde)

bis(1-methyl-indol-3-yl)-4-isopropylphenylmethane

bis(1-methyl-indol-3-yl)-4-isopropylphenylmethane

Conditions
ConditionsYield
With ruthenium trichloride In methanol at 20℃; for 0.05h;98%
2-hydroxy-2-phenylacetophenone
119-53-9

2-hydroxy-2-phenylacetophenone

(4-isopropylbenzaldehyde)
122-03-2

(4-isopropylbenzaldehyde)

2‐(4‐isopropylphenyl)‐4,5‐diphenyl‐1H‐imidazole
5496-37-7

2‐(4‐isopropylphenyl)‐4,5‐diphenyl‐1H‐imidazole

Conditions
ConditionsYield
With 4,4'-diiodobiphenyl; ammonium acetate In ethanol for 0.5h; Heating;98%
With oxaline; ammonium acetate at 110℃; for 1h;80%
3-amino-2-methyl-6,7-methylenedioxyquinazolin-4(3H)-one
66117-84-8

3-amino-2-methyl-6,7-methylenedioxyquinazolin-4(3H)-one

(4-isopropylbenzaldehyde)
122-03-2

(4-isopropylbenzaldehyde)

3-[(4-isopropylbenzylidene)amino]-2-methyl-6,7-methylenedioxy-quinazolin-4(3H)-one
1192243-22-3

3-[(4-isopropylbenzylidene)amino]-2-methyl-6,7-methylenedioxy-quinazolin-4(3H)-one

Conditions
ConditionsYield
With hydrogenchloride In ethanol; water at 20℃; for 1h; diastereoselective reaction;98%
anthranilic acid amide
28144-70-9

anthranilic acid amide

(4-isopropylbenzaldehyde)
122-03-2

(4-isopropylbenzaldehyde)

2,3-dihydro-2-(4-isopropylphenyl)quinazolin-4(1H)-one
83800-96-8

2,3-dihydro-2-(4-isopropylphenyl)quinazolin-4(1H)-one

Conditions
ConditionsYield
With phosphatidylcholine In water at 80℃; for 1h; Green chemistry;98%
With 1,3,5-trichloro-2,4,6-triazine In acetonitrile at 20℃; for 0.166667h; chemoselective reaction;90%
With silica supported ceric ammonium nitrate (CAN*SiO2) In acetonitrile at 20℃; for 0.166667h;90%
2-oxo-propionic acid
127-17-3

2-oxo-propionic acid

(4-isopropylbenzaldehyde)
122-03-2

(4-isopropylbenzaldehyde)

C12H16O2

C12H16O2

Conditions
ConditionsYield
With cyclohexane-1,2-dione hydrolase In aq. buffer at 30℃; for 48h; pH=6.5; Enzymatic reaction;98%
1H-benzimidazol-2-amine
934-32-7

1H-benzimidazol-2-amine

(4-isopropylbenzaldehyde)
122-03-2

(4-isopropylbenzaldehyde)

malononitrile
109-77-3

malononitrile

2-amino-4-(4-isopropylphenyl)-1,4-dihydrobenzo[4,5]imidazolo[1,2-a]pyrimidine-3-carbonitrile
932995-93-2

2-amino-4-(4-isopropylphenyl)-1,4-dihydrobenzo[4,5]imidazolo[1,2-a]pyrimidine-3-carbonitrile

Conditions
ConditionsYield
With poly(vinylpyrrolidonium) perchlorate ([PVPH]ClO4) at 100℃; for 0.0666667h;98%
With toluene-4-sulfonic acid In neat (no solvent) at 80℃; for 0.55h; Green chemistry;92%
With 1-methyl-3-(trimethoxysilylpropyl)imidazolium hydrogen sulfate supported on rice husk ash In neat (no solvent) at 100℃; for 0.0833333h; Green chemistry;88%
cyclohexanecarbohydrazide
38941-47-8

cyclohexanecarbohydrazide

(4-isopropylbenzaldehyde)
122-03-2

(4-isopropylbenzaldehyde)

(E)-N'-(4-isopropylbenzylidene)cyclohexanecarbohydrazide

(E)-N'-(4-isopropylbenzylidene)cyclohexanecarbohydrazide

Conditions
ConditionsYield
In ethanol at 20℃; for 2h;98%
diisopropyl hydrogenphosphonate
1809-20-7

diisopropyl hydrogenphosphonate

(4-isopropylbenzaldehyde)
122-03-2

(4-isopropylbenzaldehyde)

malononitrile
109-77-3

malononitrile

diisopropyl [2,2-dicyano-1-(4-isopropylphenyl)ethyl]phosphonate

diisopropyl [2,2-dicyano-1-(4-isopropylphenyl)ethyl]phosphonate

Conditions
ConditionsYield
With dibutylamine In neat (no solvent) at 20℃; Green chemistry;98%
1-(7-hydroxy-2,2-dimethylchroman-6-yl)ethanone
31273-58-2

1-(7-hydroxy-2,2-dimethylchroman-6-yl)ethanone

(4-isopropylbenzaldehyde)
122-03-2

(4-isopropylbenzaldehyde)

(E)-1-(7-hydroxy-2,2-dimethylchroman-6-yl)-3-(4-isopropylphenyl)prop-2-en-1-one

(E)-1-(7-hydroxy-2,2-dimethylchroman-6-yl)-3-(4-isopropylphenyl)prop-2-en-1-one

Conditions
ConditionsYield
With potassium hydroxide In ethanol at 90℃; Claisen-Schmidt Condensation; Microwave irradiation;98%
cuminol
536-60-7

cuminol

(4-isopropylbenzaldehyde)
122-03-2

(4-isopropylbenzaldehyde)

Conditions
ConditionsYield
With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; oxygen In dichloromethane; water under 760.051 Torr; for 2h; Green chemistry;100%
With dmap; C25H30F17N5O4S(1-)*K(1+); oxygen; copper(II) sulfate In water at 25℃; for 2h; chemoselective reaction;99%
With titanium(IV) oxide; oxygen at 29.84℃; under 760.051 Torr; for 6h; Sealed tube; Irradiation;99%
isopropyllithium
1888-75-1

isopropyllithium

4-bromo-benzaldehyde
1122-91-4

4-bromo-benzaldehyde

(4-isopropylbenzaldehyde)
122-03-2

(4-isopropylbenzaldehyde)

Conditions
ConditionsYield
Stage #1: 4-bromo-benzaldehyde With bis(tri-tert-butylphosphine)palladium(0); sodium chloride In water at 20℃; for 0.166667h; Negishi Coupling; Schlenk technique;
Stage #2: isopropyllithium With zinc(II) chloride In 2-methyltetrahydrofuran; water at 10℃; for 0.00555556h; Schlenk technique; chemoselective reaction;
98%
4-isopropylbenzaldehyde oxime
3717-17-7, 3717-18-8, 13372-80-0

4-isopropylbenzaldehyde oxime

(4-isopropylbenzaldehyde)
122-03-2

(4-isopropylbenzaldehyde)

Conditions
ConditionsYield
With iron(III) chloride; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; oxygen In water; toluene at 60℃; under 760.051 Torr; for 4h;95%
With tungsten(VI) chloride; zinc In acetonitrile at 20℃; for 0.333333h;92%
2-(4-isopropylphenyl)-1,3-dithiane

2-(4-isopropylphenyl)-1,3-dithiane

(4-isopropylbenzaldehyde)
122-03-2

(4-isopropylbenzaldehyde)

Conditions
ConditionsYield
With 1,3,5-trichloro-2,4,6-triazine; dimethyl sulfoxide In dichloromethane at 20℃; for 1h;94%
2-(4-isopropylphenyl)-1,3-dithiolane
23229-31-4

2-(4-isopropylphenyl)-1,3-dithiolane

(4-isopropylbenzaldehyde)
122-03-2

(4-isopropylbenzaldehyde)

Conditions
ConditionsYield
With 1,3,5-trichloro-2,4,6-triazine; dimethyl sulfoxide In dichloromethane at 20℃; for 2.45h;93%
With Oxone; potassium bromide In water; acetonitrile at 20℃; for 0.333333h;92%
With iodosylbenzene In dichloromethane at 20℃; for 0.25h;91%

122-03-2Relevant articles and documents

A polyoxometalate@covalent triazine framework as a robust electrocatalyst for selective benzyl alcohol oxidation coupled with hydrogen production

Li, Zhen,Zhang, Junhao,Jing, Xiaoting,Dong, Jing,Liu, Huifang,Lv, Hongjin,Chi, Yingnan,Hu, Changwen

, p. 6152 - 6159 (2021)

Electrocatalytic oxidation has been proven as a sustainable and promising alternative to traditional chemical transformation, but its further development is limited by the use of noble-metal electrocatalysts. Herein, a polyoxometalate-based electrode material,H5PMo10V2O40@CTF(denoted asPMo10V2@CTF), has been successfully fabricated through electrostatic assembly of a molecular polyoxometalate catalyst,PMo10V2, with a porous cationic covalent triazine framework (CTF), which, to our knowledge, represents the first combination of polyoxometalate with a cationic CTF. The resultingPMo10V2@CTFexhibits high activity for the selective electrocatalytic oxidation of alcohols to aldehydes, achieving 99% conversion of benzyl alcohol, over 99% selectivity of benzyl aldehyde, and at the same time near unity H2production. Notably, the reported electrocatalytic system presents good atom economy, high energy conversion (96% faradaic efficiency), remarkable catalytic activity and robustness for at least eight recycles. Based on the various experimental and spectroscopic analyses, a possible catalytic mechanism was proposed, revealing that such excellent electrocatalytic performance is attributed to the versatile redox ability ofPMo10V2and the good porosity and adsorption property of the CTF in the constructedPMo10V2@CTFcomposite.

Gold nanoparticles supported on Cs2CO3 as recyclable catalyst system for selective aerobic oxidation of alcohols at room temperature

Karimi, Babak,Kabiri Esfahani, Farhad

, p. 5555 - 5557 (2009)

NaAuCl4/Cs2CO3 was found to be a simple bench top, recyclable and selective catalyst system for the aerobic oxidation of various types of alcohols into their corresponding aldehydes and ketones at room temperature without the need for any further polymeric and/or oxidic support.

Design and development of natural and biocompatible raffinose-Cu2O magnetic nanoparticles as a heterogeneous nanocatalyst for the selective oxidation of alcohols

Eivazzadeh-Keihan, Reza,Esmaeili, Mir Saeed,Ghafuri, Hossein,Maleki, Ali,Varzi, Zahra

, (2020)

Natural polymers are recently playing a vital role as a support for the noble metals. In the present study, raffinose from the classes of oligosaccharide polymer with a high capacity of magnetization was used as active support for the copper metal. The copper immobilized on the raffinose-based magnetic nanoparticles (MNPs) which can be used as a recyclable heterogeneous nanocatalyst for the selective oxidation of primary benzyl alcohols (PBA) to benzaldehyde (BAD) derivatives. The morphology and structure of the recoverable magnetic nanocatalyst were characterized using different microscopic and spectroscopic techniques including FT-IR, GC, VSM, XRD, TEM, TGA, FESEM and EDS analyses. Also, the optimum conditions of co-reactant, reaction time, oxidant, temperature and amount of the nanocatalyst for oxidation reaction were investigated. Moreover, the Fe3O4?raffinose-Cu2O NPs had a significant effect to enhance yield and reduce the reaction time.

Preparation of large-size, superparamagnetic, and highly magnetic Fe3O4@PDA core-shell submicrosphere-supported nano-palladium catalyst and its application to aldehyde preparation through oxidative dehydrogenation of benzyl alcohols

Guo, Haichang,Zheng, Renhua,Jiang, Huajiang,Xu, Zhenyuan,Xia, Aibao

, (2019)

Large-size, superparamagnetic, and highly magnetic Fe3O4@PDA core-shell submicrospheresupported nano-palladium catalysts were prepared in this study. Dopamine was encapsulated on the surface of Fe3O4 particles via self-polymerization and then protonated to positively charge the microspheres. PdCl42- was dispersed on the surface of the microspheres by positive and negative charge attraction and then reduced to nano-palladium. With air as oxidant, the catalyst can successfully catalyze the dehydrogenation of benzyl alcohols to produce the corresponding aldehydes at 120 °C.

Multifunctional radical-doped polyoxometalate-based host-guest material: Photochromism and photocatalytic activity

Liao, Jian-Zhen,Zhang, Hai-Long,Wang, Sa-Sa,Yong, Jian-Ping,Wu, Xiao-Yuan,Yu, Rongmin,Lu, Can-Zhong

, p. 4345 - 4350 (2015)

An effective strategy to synthesize multifunctional materials is the incorporation of functional organic moieties and metal oxide clusters via self-assembly. A rare multifunctional radical-doped zinc-based host-guest crystalline material was synthesized with a fast-responsive reversible ultraviolet visible light photochromism, photocontrolled tunable luminescence, and highly selective photocatalytic oxidation of benzylic alcohols as a result of blending of distinctively different functional components, naphthalenediimide tectons, and polyoxometalates (POMs). It is highly unique to link π-electron-deficient organic tectons and POMs by unusual POMs anion-π interactions, which are not only conducive to keeping the independence of each component but also effectively promoting the charge transfer or exchange among the components to realize the fast-responsive photochromism, photocontrolled tunable luminescence, and photocatalytic activity.

TEMPO-mediated aerobic oxidation of alcohols using copper(II) complex of bis(phenol) di-amine ligand as biomimetic model for Galactose oxidase enzyme

Safaei, Elham,Hajikhanmirzaei, Leila,Karimi, Babak,Wojtczak, Andrzej,Coti?, Patricia,Lee, Yong-Ill

, p. 153 - 162 (2016)

Mononuclear copper complexes of four-dentate N2O2 bis(phenol) diamine ligands (H2LNEX X: C and OB in which C and OB are chloro and tert-butyl-methoxy substituents on phenol groups) have been synthesized and characterized by IR, UV-Vis, single crystal X-ray diffraction, magnetic susceptibility studies and cyclic voltammetry techniques. The CuLNEX complexes show the square pyramid geometry of the coordination sphere with the copper centers surrounded by two nitrogen and oxygen atoms from the coordinating ligand and an axially bound water molecule. The effective magnetic moments of 1.7 and 1.8 BM confirm a monomer complex with copper(II) center. Electrochemical oxidation of these complexes yielded the corresponding Cu(II)-phenoxyl radical species. In addition, CuLNEX complexes, have shown efficient catalytic activities for TEMPO-mediated oxidation of a set of alcohols to the corresponding aldehydes in the presence of molecular oxygen as oxidant at room temperature.

Protonated Pteridine and Flavin Analogues acting as Efficient and Substrate-selective Photocatalysts in the Oxidation of Benzyl Alcohol Derivatives by Oxygen

Fukuzumi, Shunichi,Tanii, Kumiko,Tanaka, Toshio

, p. 816 - 818 (1989)

Protonated aminopterin, lumazine, and riboflavin-tetra-acetate efficiently catalyse the substrate selective photo-oxidation of benzyl alcohol derivatives by oxygen in the presence of perchloric acid in acetonitrile at 298 K.

A copper complex of a noninnocent iminophenol-amidopyridine hybrid ligand: Synthesis, characterization, and aerobic alcohol oxidation

Alaji, Zahra,Safaei, Elham,Chiang, Linus,Clarke, Ryan M.,Mu, Changhua,Storr, Tim

, p. 6066 - 6074 (2014)

Reaction of the noninnocent iminophenol-iminopyridine hybrid ligand HLIPIP, where LIPIP denotes [2-((E)-{(E)-2-[(E)-pyridin-2-ylmethyleneamino]benzylidene}amino)-4,6-di-tert-butylphenolate], with copper acetate afforded a copper complex, LAPIPCuII, in which one of the imine functional groups is oxidized to an amide during metal complexation. The new CuII complex is capable of catalyzing efficient aerobic alcohol oxidation under mild conditions. The crystal structure of LAPIPCuII exhibits a square-planar geometry with the CuII center coordinated by three nitrogen atoms and one oxygen atom. Electrochemical studies were conducted to evaluate the redox-active behavior of the complex, and the results showed a quasireversible reduction and a ligand-based oxidation process. The neutral species of LAPIPCuII is EPR active, which is consistent with a paramagnetic electronic ground state (d9, S = 1/2), whereas the one-electron oxidized complex was X-band EPR silent. One-electron chemical oxidation of LAPIPCuII gave a new species that can be attributed to a CuII-phenoxyl radical complex. Based on EPR measurements in conjunction with density functional theory calculations, [LAPIPCuII]+ is proposed to have a triplet electronic ground state, exhibiting a weak ferromagnetic interaction between the CuII center and the coordinated phenoxyl radical. A new copper complex of a noninnocent iminophenol-pyridine hybrid ligand that is capable of efficient aerobic alcohol oxidation was studied.

Efficient and Reusable Sn(II)-containing Imidazolium-based Ionic Liquid as a Catalyst for the Oxidation of Benzyl Alcohol

Wang, Bingtong,Hu, Yulin,Fang, Dong,Wu, Lin,Xing, Rong

, p. 991 - 999 (2016)

A simple and efficient catalytic system [BBIM]Br–SnCl2 for the oxidation of benzyl alcohol using hydrogen peroxide as the oxidant has been developed. Reaction conditions such as the catalyst dose, the solvents, reaction temperature, reaction time, and the amount of hydrogen peroxide were investigated. The optimum reaction conditions identified were 0.11 g of catalyst, no solvent, 65°C, 15 min, and 2 mmol of hydrogen peroxide. Oxidation of various alcohols was also investigated under the optimized conditions. The catalyst [BBIM]Br–SnCl2 can be easily recovered and reused for six reaction runs without significant loss of catalytic activity, because the Sn species of the catalyst can be coordinated with the imidazole ring of the ionic liquid. The reused catalyst was further characterized by Fourier transform infrared spectroscopy to evaluate its chemical properties. The results proved that the [BBIM]Br–SnCl2 catalyst was stable and reusable for the oxidation reactions. A possible mechanism for the oxidation of benzyl alcohol to benzaldehyde is proposed.

Substrate-selective Photo-oxidation of Benzyl Alcohol Derivatives with Oxygen, catalysed by an NAD+ Model Compound

Fukuzumi, Shunichi,Kuroda, Sadaki,Tanaka, Toshio

, p. 120 - 122 (1987)

An NAD+ model compound, 10-methylacridinium ion (AcrH+), catalyses the substrate-selective photo-oxidation of benzyl alcohol derivatives with oxygen in acetonitrile at 298 K, which is initiated by the electron-transfer reactions from benzyl alcohol derivatives to the singlet excited state of AcrH+.

On the stabilization of gold nanoparticles over silica-based magnetic supports modified with organosilanes

Oliveira, Rafael L.,Zanchet, Daniela,Kiyohara, Pedro K.,Rossi, Liane M.

, p. 4626 - 4631 (2011)

The immobilization of gold nanoparticles (Au NPs) on silica is made possible by the functionalization of the silica surfaces with organosilanes. Au NPs could only be stabilized and firmly attached to silica-support surfaces that were previously modified with amino groups. Au NPs could not be stabilized on bare silica surfaces and most of the NPs were then found in the solution. The metal-support interactions before and after the Au NP formation, observed by X-ray absorption fine structure spectroscopy (XAFS), indicate a stronger interaction of gold(III) ions with amino-modified silica surfaces than with the silanol groups in bare silica. An amino-modified, silica-based, magnetic support was used to prepare an active Au NP catalyst for the chemoselective oxidation of alcohols, a reaction of great interest for the fine chemical industry.

Creation of a high-valent manganese species on hydrotalcite and its application to the catalytic aerobic oxidation of alcohols

Nagashima, Kohji,Mitsudome, Takato,Mizugaki, Tomoo,Jitsukawa, Koichiro,Kaneda, Kiyotomi

, p. 2142 - 2144 (2010)

A high-valent Mn oxide species is successfully synthesized on the surface of hydrotalcite (Mn/HT-Ox), and is found to act as an efficient heterogeneous catalyst for the oxidation of alcohols using molecular oxygen as an oxidant.

Maximizing the Number of Interfacial Sites in Single-Atom Catalysts for the Highly Selective, Solvent-Free Oxidation of Primary Alcohols

Li, Tianbo,Liu, Fei,Tang, Yan,Li, Lin,Miao, Shu,Su, Yang,Zhang, Junying,Huang, Jiahui,Sun, Hui,Haruta, Masatake,Wang, Aiqin,Qiao, Botao,Li, Jun,Zhang, Tao

, p. 7795 - 7799 (2018)

The solvent-free selective oxidation of alcohols to aldehydes with molecular oxygen is highly attractive yet challenging. Interfacial sites between a metal and an oxide support are crucial in determining the activity and selectivity of such heterogeneous catalysts. Herein, we demonstrate that the use of supported single-atom catalysts (SACs) leads to high activity and selectivity in this reaction. The significantly increased number of interfacial sites, resulting from the presence of individually dispersed metal atoms on the support, renders SACs one or two orders of magnitude more active than the corresponding nanoparticle (NP) catalysts. Lattice oxygen atoms activated at interfacial sites were found to be more selective than O2 activated on metal NPs in oxidizing the alcohol substrate. This work demonstrates for the first time that the number of interfacial sites is maximized in SACs, providing a new avenue for improving catalytic performance by developing appropriate SACs for alcohol oxidation and other reactions occurring at metal–support interfacial sites.

The selective catalytic oxidation of terminal alcohols: A novel four-component system with MTO as catalyst

Herrmann, Wolfgang A.,Zoller, Jochen P.,Fischer, Richard W.

, p. 404 - 407 (1999)

A four-component system (H2O2, MTO, HBr, TEMPO) in acetic acid catalyzes the selective oxidation of terminal alcohols to the corresponding aldehydes with excellent selectivity and yield. The system allows the oxidation of alcohols with hydrogen peroxide as oxidants either selectively to aldehydes or to the corresponding acids, depending on the reaction parameters. The new technique is especially applicable to the oxidation of carbohydrates.

Zinc substituted Keggin-type polyoxometalate on Dowex: a green heterogeneous catalyst for oxidation of alcohols in water

Aghayi, Mehdi,Yadollahi, Bahram,Farsani, Mostafa Riahi

, p. 2895 - 2900 (2020)

In this work, homogeneous and heterogeneous oxidation of alcohols by H2O2 in the presence of [(n-C4H9)4?N]5[PW11ZnO39].3H2O and [PW11ZnO39]5? supported on Dowex 22 as catalysts have been investigated. Using water as a green solvent, different alcohols were converted into the corresponding aldehydes and ketones in high to excellent yields. Dowex 22 supported polyoxometalate, PW11Zn@Dowex, was also catalyzed highly robust and selective oxidation of unsaturated alcohols. Leaching and recycling experiments on supported catalyst revealed the excellent stability and reusability of this catalytic system.

-

Arai,M.

, p. 252 - 255 (1965)

-

-

Borgwardt,Schwenk

, p. 1185,1187 (1934)

-

Electrochemical Aerobic Oxidative Cleavage of (sp3)C-C(sp3)/H Bonds in Alkylarenes

Liu, Shuai,Liu, Zhong-Quan,Shen, Tong,Shen, Xu,Wang, Nengyong,Wu, Jintao,Yang, Le,Zhao, Jianyou

, p. 3286 - 3295 (2022/03/14)

An electrochemistry-promoted oxidative cleavage of (sp3)C-C(sp3)/H bonds in alkylarenes was developed. Various aryl alkanes can be smoothly converted into ketones/aldehydes under aerobic conditions using a user-friendly undivided cell setup. The features of air as oxidant, scalability, and mild conditions make them attractive in synthetic organic chemistry.

Selective Electrochemical Oxygenation of Alkylarenes to Carbonyls

Li, Xue,Bai, Fang,Liu, Chaogan,Ma, Xiaowei,Gu, Chengzhi,Dai, Bin

supporting information, p. 7445 - 7449 (2021/10/02)

An efficient electrochemical method for benzylic C(sp3)-H bond oxidation has been developed. A variety of methylarenes, methylheteroarenes, and benzylic (hetero)methylenes could be converted into the desired aryl aldehydes and aryl ketones in moderate to excellent yields in an undivided cell, using O2 as the oxygen source and lutidinium perchlorate as an electrolyte. On the basis of cyclic voltammetry studies, 18O labeling experiments, and radical trapping experiments, a possible single-electron transfer mechanism has been proposed for the electrooxidation reaction.

PhIO-Mediated oxidative dethioacetalization/dethioketalization under water-free conditions

Du, Yunfei,Ouyang, Yaxin,Wang, Xi,Wang, Xiaofan,Yu, Zhenyang,Zhao, Bingyue,Zhao, Kang

, p. 48 - 65 (2021/06/16)

Treatment of thioacetals and thioketals with iodosobenzene in anhydrous DCM conveniently afforded the corresponding carbonyl compounds in high yields under water-free conditions. The mechanistic studies indicate that this dethioacetalization/dethioketalization process does not need water and the oxygen of the carbonyl products comes from the hypervalent iodine reagent.

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