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536-60-7 Usage

Description

p-Isopropylbenzyl alcohol has an intense, persistent, caraway-like odor and an aromatic, burning taste. Prepared from cuminaldehyde with H2 or NH3 under pressure in methanol solution and in the presence of Raney Ni catalyst; or by catalytic reduction of methyl p-isopropy lbenzoate.

Chemical Properties

Different sources of media describe the Chemical Properties of 536-60-7 differently. You can refer to the following data:
1. p-Isopropylbenzene alcohol has an intense, persistent, caraway-like odor and an aromatic, burning taste
2. CLEAR COLOURLESS TO SLIGHTLY YELLOW LIQUID

Occurrence

Reported found in the oil from fruits of Cuminum cyminum and Carum carvi L.; also in the oils of Eucalyptus bakeris (esterified) and French lavender. Also reported found in mandarin peel oil, lingonberry, black currants, blackberry, tomato, cumin seed, peppermint oil, nutmeg, thymus, cognac, licorice, lovage seed, dill, laurel, turmeric, calabash nutmeg, angelica root oil and mastic gum leaf and fruit oil

Uses

Flavoring.

Definition

Found in caraway seed.

Preparation

From cuminaldehyde with H2 or NH3 under pressure in methanol solution and in the presence of Raney Ni catalyst, or by catalytic reduction of methyl p-isopropylbenzoate

General Description

4-Isopropylbenzyl alcohol has mosquito repellent properties and has been isolated from Eucalyptus camaldulensis. Oxidation of 4-isopropylbenzyl alcohol over TiO2-supported nano gold catalyst has been investigated.

Check Digit Verification of cas no

The CAS Registry Mumber 536-60-7 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,3 and 6 respectively; the second part has 2 digits, 6 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 536-60:
(5*5)+(4*3)+(3*6)+(2*6)+(1*0)=67
67 % 10 = 7
So 536-60-7 is a valid CAS Registry Number.
InChI:InChI=1/C9H12O/c1-9(2,10)8-6-4-3-5-7-8/h3-7,10H,1-2H3

536-60-7 Well-known Company Product Price

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  • Alfa Aesar

  • (A12172)  4-Isopropylbenzyl alcohol, tech. 90%   

  • 536-60-7

  • 25g

  • 402.0CNY

  • Detail
  • Alfa Aesar

  • (A12172)  4-Isopropylbenzyl alcohol, tech. 90%   

  • 536-60-7

  • 100g

  • 778.0CNY

  • Detail

536-60-7SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 19, 2017

Revision Date: Aug 19, 2017

1.Identification

1.1 GHS Product identifier

Product name 4-Isopropylbenzyl Alcohol

1.2 Other means of identification

Product number -
Other names 4-Isopropylbenzyl alcohol

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:536-60-7 SDS

536-60-7Synthetic route

4-iso-propylbenzyl trimethylsilyl ether
71700-48-6

4-iso-propylbenzyl trimethylsilyl ether

cuminol
536-60-7

cuminol

Conditions
ConditionsYield
With Nafion-H(R); silica gel In hexane at 20℃; for 0.333333h;98%
With methanol; 1,3-disulfonic acid imidazolium hydrogen sulfate at 20℃; for 0.0666667h; Green chemistry;97%
With poly (ethylene glycol)-sulfonated sodium montmorillonite nanocomposite In methanol at 20℃; for 0.0166667h;96%
With methanol; vanadium hydrogen sulfate at 20℃; for 0.0166667h;90%
With Nanoporous Na+-Montmorillonite Perchloric Acid In ethanol at 20℃; for 0.0333333h;87%
isopropylboronic acid
80041-89-0

isopropylboronic acid

4-bromobenzenemethanol
873-75-6

4-bromobenzenemethanol

cuminol
536-60-7

cuminol

Conditions
ConditionsYield
Stage #1: 4-bromobenzenemethanol With C44H35BrN2O2P2Pd In toluene at 20℃; for 0.5h; Suzuki-Miyaura Coupling; Inert atmosphere; Irradiation;
Stage #2: isopropylboronic acid With potassium phosphate In water at 100℃; for 48h; Suzuki-Miyaura Coupling; Inert atmosphere;
98%
(4-isopropylbenzaldehyde)
122-03-2

(4-isopropylbenzaldehyde)

cuminol
536-60-7

cuminol

Conditions
ConditionsYield
With sodium tetrahydroborate In methanol at 0℃; Inert atmosphere;97%
With methanol; sodium tetrahydroborate at 0℃; for 0.5h;97.3%
With hydrogen In water at 20℃; under 760.051 Torr; for 10h; Green chemistry; chemoselective reaction;96%
tert-butyl-(4-isopropyl-benzyloxy)-dimethyl-silane

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

cuminol
536-60-7

cuminol

Conditions
ConditionsYield
With N-iodo-succinimide In methanol at 20℃; for 24h;96%
sulfonic acid functionalized nanoporous silica In methanol at 35℃; for 1.5h;95%
With methanol at 20℃; for 2h;92%
perillol
536-59-4

perillol

cuminol
536-60-7

cuminol

Conditions
ConditionsYield
With cis-Octadecenoic acid; palladium on activated charcoal In cyclohexane at 110℃; for 2h; Temperature;95%
With 5 weight% palladium(0) nanoparticles supported on mesoporous natural phosphate In neat (no solvent) for 24h; Reflux;91%
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

cuminol
536-60-7

cuminol

Conditions
ConditionsYield
With silica gel In methanol for 4h; Reflux;91%
4-iso-propyl-1-[(ethoxymethoxy)methyl]benzene
1058648-64-8

4-iso-propyl-1-[(ethoxymethoxy)methyl]benzene

cuminol
536-60-7

cuminol

Conditions
ConditionsYield
phosphotungstic acid In ethanol for 5h; Heating;83%
4-Me2CHC6H4CH2OMOM
1058648-60-4

4-Me2CHC6H4CH2OMOM

cuminol
536-60-7

cuminol

Conditions
ConditionsYield
phosphotungstic acid In ethanol for 5.5h; Heating;81%
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-i-propylbenzyl bromide
73789-86-3

4-i-propylbenzyl bromide

cuminol
536-60-7

cuminol

Conditions
ConditionsYield
With oxygen; eosin y In dimethyl sulfoxide at 25℃; for 12h; Irradiation;76%
4-methylisopropylbenzene
99-87-6

4-methylisopropylbenzene

A

p-cymene-8-ol
1197-01-9

p-cymene-8-ol

B

cuminol
536-60-7

cuminol

Conditions
ConditionsYield
With ferredoxin reductase; [2Fe-2S] ferredoxin; cytochrome P450 101B1 enzyme from Novosphingobium aromaticivorans DSM12444; oxygen; NADH; bovine liver catalase In aq. buffer at 30℃; pH=7.4; Catalytic behavior; Kinetics; Enzymatic reaction;A 25%
B 75%
With lithium aluminium tetrahydride; oxygen; dibenzoyl peroxide 1.) 125 deg C; Multistep reaction. Title compound not separated from byproducts;
With lithium aluminium tetrahydride; 2,2'-azobis(isobutyronitrile); oxygen Product distribution; multistep reaction: 1) 90 deg C, 2) ether, 30 min, reflux; obj. of study: autoxidation, relative reaction rate;A 84.4 % Chromat.
B 15.6 % Chromat.
With NADPH In dimethyl sulfoxide at 30℃; pH=7.4; Product distribution; Further Variations:; Reagents;A 76 % Chromat.
B 2 % Chromat.
With ferredoxin reductase; ferredoxin; P450 monooxygenase CYP101B1 from a Novosphingobium bacterium, wild type; NADH; bovine liver catalase In aq. buffer at 30℃; pH=7.4; Kinetics; Reagent/catalyst; Enzymatic reaction; regioselective reaction;
4-(i-propyl)benzyl acetate
59230-57-8

4-(i-propyl)benzyl acetate

A

4,4'-(oxybis(methylene))bis(isopropylbenzene)
146689-61-4

4,4'-(oxybis(methylene))bis(isopropylbenzene)

B

cuminol
536-60-7

cuminol

Conditions
ConditionsYield
With sodium hydroxide In methanol; water for 3h; Heating;A 24%
B 72%
4-bromobenzenemethanol
873-75-6

4-bromobenzenemethanol

isopropyllithium
1888-75-1

isopropyllithium

cuminol
536-60-7

cuminol

Conditions
ConditionsYield
With bis(tri-t-butylphosphine)palladium(0) In toluene at 20℃; for 1h;61%
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%
(1R,2S,4S,6R)-7,7-dimethyl-3-oxabicyclo[4.1.1.02.4]octane-2-methanol
35670-95-2, 104320-46-9, 105815-51-8

(1R,2S,4S,6R)-7,7-dimethyl-3-oxabicyclo[4.1.1.02.4]octane-2-methanol

A

(1R)-3-(hydroxymethyl)-2,2-dimethylcyclopent-3-ene-1-acetaldehyde

(1R)-3-(hydroxymethyl)-2,2-dimethylcyclopent-3-ene-1-acetaldehyde

B

cuminol
536-60-7

cuminol

Conditions
ConditionsYield
With askanite-bentonite clay In dichloromethane at 20℃; for 0.666667h;A 27%
B 16%
(1R)-Myrtenol
19894-97-4

(1R)-Myrtenol

A

6,6-dimethyl-2-methylene-bicyclo[3.1.1]heptan-3-ol
19894-98-5

6,6-dimethyl-2-methylene-bicyclo[3.1.1]heptan-3-ol

B

(-)-perillyl alcohol
536-59-4, 18457-55-1

(-)-perillyl alcohol

C

cuminol
536-60-7

cuminol

Conditions
ConditionsYield
With askanite-bentonite clay In dichloromethane at 20℃; for 1h;A 9%
B 12%
C 6%
formaldehyd
50-00-0

formaldehyd

4-isopropylphenylmagnesium bromide
18620-03-6

4-isopropylphenylmagnesium bromide

cuminol
536-60-7

cuminol

formaldehyd
50-00-0

formaldehyd

4-isopropyl-phenyl magnesium (1+); bromide

4-isopropyl-phenyl magnesium (1+); bromide

cuminol
536-60-7

cuminol

p-isopropylbenzoic acid methyl ester
20185-55-1

p-isopropylbenzoic acid methyl ester

A

4-Isopropylbenzoic acid
536-66-3

4-Isopropylbenzoic acid

B

cuminol
536-60-7

cuminol

Conditions
ConditionsYield
With methanol; copper oxide-chromium oxide barium oxide; hydrogen at 155 - 160℃; under 220652 - 294203 Torr;
(4-isopropylbenzyl)magnesium chloride
405506-94-7

(4-isopropylbenzyl)magnesium chloride

cuminol
536-60-7

cuminol

Conditions
ConditionsYield
With diethyl ether; oxygen
(4-isopropylbenzaldehyde)
122-03-2

(4-isopropylbenzaldehyde)

A

4-Isopropylbenzoic acid
536-66-3

4-Isopropylbenzoic acid

B

cuminol
536-60-7

cuminol

Conditions
ConditionsYield
With potassium carbonate
(4-isopropylbenzaldehyde)
122-03-2

(4-isopropylbenzaldehyde)

A

4-isopropylbenzylamine
4395-73-7

4-isopropylbenzylamine

B

cuminol
536-60-7

cuminol

Conditions
ConditionsYield
With ammonia; nickel at 60℃; under 66195.7 Torr; Hydrogenation;
4-isopropylbenzyl chloride
2051-18-5

4-isopropylbenzyl chloride

cuminol
536-60-7

cuminol

Conditions
ConditionsYield
With potassium carbonate; acetone
Multi-step reaction with 2 steps
1: 55.7 percent / triethylamine / ethyl acetate / Heating
2: 72 percent / sodium hydroxide / methanol; H2O / 3 h / Heating
View Scheme
p-isopropylbenzoic acid methyl ester
20185-55-1

p-isopropylbenzoic acid methyl ester

cuminol
536-60-7

cuminol

Conditions
ConditionsYield
With bis(cyclopentadienyl)titanium dichloride; sodium In benzene
4-methylisopropylbenzene
99-87-6

4-methylisopropylbenzene

A

p-cymene-8-ol
1197-01-9

p-cymene-8-ol

B

8-hydroperoxy-p-cymene
3077-71-2

8-hydroperoxy-p-cymene

C

4-isopropylbenzyl nitrate
95543-77-4

4-isopropylbenzyl nitrate

D

para-methylacetophenone
122-00-9

para-methylacetophenone

E

(4-isopropylbenzaldehyde)
122-03-2

(4-isopropylbenzaldehyde)

F

cuminol
536-60-7

cuminol

Conditions
ConditionsYield
With oxygen In acetonitrile for 5h; photochemical autooxidation;A n/a
B n/a
C 9 % Spectr.
D n/a
E 31 % Spectr.
F 9 % Spectr.
4-methylisopropylbenzene
99-87-6

4-methylisopropylbenzene

A

4-isopropyl-benzyl hydroperoxide
5699-45-6

4-isopropyl-benzyl hydroperoxide

B

4-isopropylbenzyl nitrate
95543-77-4

4-isopropylbenzyl nitrate

C

(4-isopropylbenzaldehyde)
122-03-2

(4-isopropylbenzaldehyde)

D

cuminol
536-60-7

cuminol

Conditions
ConditionsYield
With oxygen; ammonium cerium(IV) nitrate In acetonitrile for 5h; Ambient temperature; Irradiation; Further byproducts given. Title compound not separated from byproducts;A 6 % Spectr.
B 9 % Spectr.
C 31 % Spectr.
D 9 % Spectr.
4-methylisopropylbenzene
99-87-6

4-methylisopropylbenzene

cuminol
536-60-7

cuminol

Conditions
ConditionsYield
Yield given. Multistep reaction;
Multi-step reaction with 3 steps
1: N-methyl-N,N,N-tributylammonium methyl sulfate / 57 °C / Electrochemical reaction
2: water / 2 h / Industry scale; Reflux
3: hydrogen / 24 h / 180 °C / 150015 Torr
View Scheme
With p-cymene methyl hydroxylase; NADH at 25℃; for 2h; pH=7; aq. phosphate buffer; Enzymatic reaction;
4-methylisopropylbenzene
99-87-6

4-methylisopropylbenzene

A

CH3C6H4CH(CH3)OH
536-50-5

CH3C6H4CH(CH3)OH

B

p-cymene-8-ol
1197-01-9

p-cymene-8-ol

C

cuminol
536-60-7

cuminol

Conditions
ConditionsYield
With lithium aluminium tetrahydride; oxygen; cobalt(II) stearate Product distribution; multistep reaction; other p-dialkylbenzenes; var. catalysts, solvents and temperatures;A n/a
B 61 % Chromat.
C 17 % Chromat.
4-methylisopropylbenzene
99-87-6

4-methylisopropylbenzene

A

p-cymene-8-ol
1197-01-9

p-cymene-8-ol

B

para-cymen-9-ol
4371-50-0

para-cymen-9-ol

C

cuminol
536-60-7

cuminol

Conditions
ConditionsYield
With lithium aluminium tetrahydride; Perbenzoic acid Mechanism; Product distribution; 2.) ether, 30 min, reflux; study of the regioselectivity of autoxidation by reduction of the corresponding oxidation-mixture;
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%
cuminol
536-60-7

cuminol

diisopropyl-carbodiimide
693-13-0

diisopropyl-carbodiimide

C17H28N2O

C17H28N2O

Conditions
ConditionsYield
With copper(II) bis(trifluoromethanesulfonate) at 100℃; for 0.0833333h; Microwave irradiation;100%
cuminol
536-60-7

cuminol

4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol
269409-70-3

4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol

C22H29BO3

C22H29BO3

Conditions
ConditionsYield
With di-tert-butyl-diazodicarboxylate In dichloromethane at 20℃; for 18h;100%
With di-tert-butyl-diazodicarboxylate In dichloromethane at 20℃; for 18h;100%
5-bromo-2-fluoropyridine
766-11-0

5-bromo-2-fluoropyridine

cuminol
536-60-7

cuminol

C15H16BrNO

C15H16BrNO

Conditions
ConditionsYield
Stage #1: cuminol With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 1h;
Stage #2: 5-bromo-2-fluoropyridine In N,N-dimethyl-formamide; mineral oil at 20℃; for 72h;
100%
Stage #1: cuminol With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 1h;
Stage #2: 5-bromo-2-fluoropyridine In N,N-dimethyl-formamide; mineral oil at 20℃; for 72h;
100%
triethylsilane
617-86-7

triethylsilane

cuminol
536-60-7

cuminol

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

triethyl((4-isopropylbenzyl)oxy)silane

Conditions
ConditionsYield
With C23H26IrN2(1+)*C32H12BF24(1-) In 1,2-dichloro-ethane for 0.0166667h; Catalytic behavior; Schlenk technique; Inert atmosphere;100%
1,1,1,3,3,3-hexamethyl-disilazane
999-97-3

1,1,1,3,3,3-hexamethyl-disilazane

cuminol
536-60-7

cuminol

4-iso-propylbenzyl trimethylsilyl ether
71700-48-6

4-iso-propylbenzyl trimethylsilyl ether

Conditions
ConditionsYield
With polyvinylpolypyrrolidonium tribromide In acetonitrile at 20℃; for 0.0833333h;99%
iodine In dichloromethane at 20℃; for 0.0333333h; Substitution;98%
With L-Aspartic acid In acetonitrile at 20℃; for 0.1h;98%
aniline
62-53-3

aniline

cuminol
536-60-7

cuminol

N-(4-isopropylbenzyl)benzenamine
81308-22-7

N-(4-isopropylbenzyl)benzenamine

Conditions
ConditionsYield
With Co2Rh2 nanoparticles immobilized on charcoal at 100℃; for 24h; Inert atmosphere; Schlenk technique; Green chemistry; chemoselective reaction;99%
With 1,10-Phenanthroline; potassium tert-butylate; nickel dibromide In toluene at 130℃; for 48h; chemoselective reaction;84%
With potassium carbonate at 160℃; for 12h;82%
1-Phenylethanol
98-85-1, 13323-81-4

1-Phenylethanol

cuminol
536-60-7

cuminol

3-(4-isopropylphenyl)-1-phenylprop-2-en-1-one
36336-80-8

3-(4-isopropylphenyl)-1-phenylprop-2-en-1-one

Conditions
ConditionsYield
With oxygen; lithium hydroxide In water; tert-butyl alcohol at 70℃;99%
cuminol
536-60-7

cuminol

1-(iodomethyl)-4-isopropylbenzene

1-(iodomethyl)-4-isopropylbenzene

Conditions
ConditionsYield
With bis(1,5-cyclooctadiene)rhodium(I) trifluoromethanesulfonate; hydrogen; iodine; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In 1,2-dichloro-ethane at 20℃; under 22502.3 Torr; Autoclave; Schlenk technique;99%
cuminol
536-60-7

cuminol

4-i-propylbenzyl bromide
73789-86-3

4-i-propylbenzyl bromide

Conditions
ConditionsYield
With 1,1,1,2,2,2-hexamethyldisilane In chloroform for 1.5h; Reflux;98%
Stage #1: cuminol With copper(l) chloride; diisopropyl-carbodiimide at 20℃; for 0.5h;
Stage #2: With N-Bromosuccinimide In 1,2-dichloro-ethane at 80℃; for 2h;
85%
With phosphorus tribromide In diethyl ether at 0℃; for 0.0833333h;84%
cuminol
536-60-7

cuminol

4-Isopropylbenzoic acid
536-66-3

4-Isopropylbenzoic acid

Conditions
ConditionsYield
With diethylene glycol dimethyl ether at 70℃; for 0.5h; Sonication;98%
With methyl 3,5-bis((1H-1,2,4-triazol-1-yl)methyl)benzoate; oxygen; sodium acetate; nickel dibromide at 120℃; under 760.051 Torr; for 72h;94%
With C14H14N6O2; oxygen; sodium acetate; palladium diacetate at 120℃; under 760.051 Torr; for 72h;94%
N,N-dimethyl acetamide
127-19-5

N,N-dimethyl acetamide

cuminol
536-60-7

cuminol

N,N-dimethyl-3-(4-isopropylphenyl)propanamide

N,N-dimethyl-3-(4-isopropylphenyl)propanamide

Conditions
ConditionsYield
With tri-tert-butyl phosphine; potassium tert-butylate; nickel diacetate In 1,4-dioxane; toluene at 80℃; for 12h; Inert atmosphere; Glovebox; Schlenk technique;98%
acetic anhydride
108-24-7

acetic anhydride

cuminol
536-60-7

cuminol

4-(i-propyl)benzyl acetate
59230-57-8

4-(i-propyl)benzyl acetate

Conditions
ConditionsYield
With decamolybdodivanadogermanic acid nanoparticles at 24.84℃; for 0.0583333h; Neat (no solvent);97%
With polyvinylpolypyrrolidone-bound boron trifluoride In acetonitrile at 20℃; for 1.5h;97%
With lithium trifluoromethanesulfonate at 20℃; for 13h;96%
aniline
62-53-3

aniline

cuminol
536-60-7

cuminol

N,N-bis(4-isopropylbenzyl)aniline
1428343-24-1

N,N-bis(4-isopropylbenzyl)aniline

Conditions
ConditionsYield
With Co2Rh2 nanoparticles immobilized on charcoal at 140℃; for 24h; Inert atmosphere; Schlenk technique; Green chemistry; chemoselective reaction;97%
1-aminodecane
2016-57-1

1-aminodecane

cuminol
536-60-7

cuminol

N-(4-isopropylbenzyl)decan-1-amine

N-(4-isopropylbenzyl)decan-1-amine

Conditions
ConditionsYield
With Co2Rh2 nanoparticles immobilized on charcoal at 80℃; for 24h; Schlenk technique; Inert atmosphere; Green chemistry; chemoselective reaction;96%
cuminol
536-60-7

cuminol

4-isopropylbenzyl chloride
2051-18-5

4-isopropylbenzyl chloride

Conditions
ConditionsYield
With thionyl chloride In dichloromethane at 0℃; for 0.833333h; Temperature;95%
With 1-methyl-pyrrolidin-2-one; benzenesulfonyl chloride In 1,2-dichloro-ethane at 80℃; for 1.5h;92%
With thionyl chloride for 1h; Chlorination; Heating;87%
toluene-4-sulfonamide
70-55-3

toluene-4-sulfonamide

cuminol
536-60-7

cuminol

N-(4-isopropylbenzyl)-4-methylbenzenesulfonamide

N-(4-isopropylbenzyl)-4-methylbenzenesulfonamide

Conditions
ConditionsYield
With air; copper diacetate; potassium carbonate at 150℃; for 12h;95%
With copper diacetate; potassium carbonate at 150℃; for 12h;95%
With potassium carbonate at 160℃; for 12h;93%
cuminol
536-60-7

cuminol

4-(i-propyl)benzyl acetate
59230-57-8

4-(i-propyl)benzyl acetate

Conditions
ConditionsYield
With phenyl-trimethyl-ammonium perbromide In acetone at 20℃; for 0.833333h;95%
1-Phenylethanol
98-85-1, 13323-81-4

1-Phenylethanol

cuminol
536-60-7

cuminol

3-(4-isopropylphenyl)-1-phenylpropan-1-ol

3-(4-isopropylphenyl)-1-phenylpropan-1-ol

Conditions
ConditionsYield
With C27H24Cl3F6IrN2; sodium hydroxide In toluene at 135℃; for 8h;95%
With C21H18MnN5O4; potassium tert-butylate In toluene at 110℃; under 750.075 Torr; for 24h; Inert atmosphere;78%
With N,N,N,N,-tetramethylethylenediamine; potassium hydroxide; nickel dibromide In octane at 130℃; for 18h; Schlenk technique; Inert atmosphere;78%
With C30H43ClCoN2P3(1+)*Cl(1-); potassium tert-butylate In toluene at 110℃; for 24h; Inert atmosphere; Glovebox; Sealed tube;79 %Spectr.
thiophenol
108-98-5

thiophenol

cuminol
536-60-7

cuminol

C16H18S

C16H18S

Conditions
ConditionsYield
With nanolayered cobalt-molybdenum sulphide with Co/(Mo+Co) mole ratio 0.83 In Hexadecane; toluene at 180℃; under 2625.26 Torr; for 18h; Inert atmosphere; Autoclave; chemoselective reaction;95%
cuminol
536-60-7

cuminol

p-Cyanocumen
13816-33-6

p-Cyanocumen

Conditions
ConditionsYield
With copper(II) choride dihydrate; ammonium formate; potassium carbonate In neat (no solvent) at 135℃; under 760.051 Torr; for 24h; Sealed tube; Schlenk technique; Green chemistry;94%
With ammonia at 250℃; Inert atmosphere;83%
With ammonium hydroxide; sodium periodate; potassium iodide at 60℃; for 3h;77%
N-hydroxyphthalimide
524-38-9

N-hydroxyphthalimide

cuminol
536-60-7

cuminol

N-(4-isopropylbenzyloxy)phthalimide
796061-04-6

N-(4-isopropylbenzyloxy)phthalimide

Conditions
ConditionsYield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 20℃; for 1h; Inert atmosphere;94%
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 20℃; Mitsunobu Displacement;
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 20℃; for 3h; Mitsunobu Displacement; Inert atmosphere;
With triphenylphosphine In tetrahydrofuran at 0 - 20℃;
acetic anhydride
108-24-7

acetic anhydride

cuminol
536-60-7

cuminol

A

4-(i-propyl)benzyl acetate
59230-57-8

4-(i-propyl)benzyl acetate

B

acetic acid
64-19-7

acetic acid

Conditions
ConditionsYield
With 3-((3-(trisilyloxy)propyl)propionamide)-1-methylimidazolium chloride ionic liquid supported on magnetic nanoparticle Fe2O3 at 20℃; for 0.416667h;A 93%
B n/a
aniline
62-53-3

aniline

cuminol
536-60-7

cuminol

N-(4-isopropylbenzylidene)benzenamine
17693-88-8

N-(4-isopropylbenzylidene)benzenamine

Conditions
ConditionsYield
With CeO2 nanorods anchored on mesoporous carbon; air In toluene at 80℃; under 760.051 Torr; for 2h;93%
With air; iron catalyst supported on mesoporous carbon In toluene at 80℃; under 750.075 Torr; for 8h; Green chemistry;84.2%
With air; Mg-Al acid-base bifunctional oxide catalyst In toluene under 750.075 Torr; for 12h;76.1%
N-(heptyl)aniline
3007-70-3

N-(heptyl)aniline

cuminol
536-60-7

cuminol

N-heptyl-N-(4-isopropylbenzyl)aniline

N-heptyl-N-(4-isopropylbenzyl)aniline

Conditions
ConditionsYield
With Co2Rh2 nanoparticles immobilized on charcoal at 140℃; for 24h; Schlenk technique; Inert atmosphere; Green chemistry; chemoselective reaction;93%

536-60-7Relevant articles and documents

COLEOSIDE, A MONOTERPENE GLYCOSIDE FROM COLEUS FORSKOHLII

Ahmed, Bahar,Vishwakarma, R. A.

, p. 3309 - 3310 (1988)

The alcoholic extract of the roots of Coleus forskohlii yielded caffeic acid and a new monoterpene glycoside, coleoside, characterised as cuminyl-O-β-D-glucopyranosyl(1->2)-β-D-galactopyranoside.Key Word Index - Coleus forskohlii; Labiatae; coleoside; cuminyl alcohol; caffeic acid.

Palladium complexes of anionic N-heterocyclic carbenes derived from sydnones in catalysis

Lücke, Ana-Luiza,Wiechmann, Sascha,Freese, Tyll,Guan, Zong,Schmidt, Andreas

, p. 643 - 650 (2016)

The anion of N-phenylsydnone, which can be generated on treatment of N-phenylsydnone with cyanomethyllithium without decomposition, can be represented as tripolar zwitterionic and as anionic N-heterocyclic carbene resonance forms. Its palladium complex was prepared from 4-bromo-3-phenylsydnone and tetrakis(triphenylphosphine)palladium and proved to be active as catalyst in Suzuki-Miyaura reactions. Thus, 2,5-dibromo-3,4-dinitrothiophene was effectively converted into 2,5-diaryl-3,4-dinitrothiophenes with 1-naphthyl, (4-trifluoromethoxy)phenyl, [4-(methylsulfanyl) phenyl], and biphenyl-4-yl boronic acid. 3-(Phenanthren-9-yl)quinoline was prepared by Suzuki-Miyaura reaction starting from 3-bromoquinoline. 1-Chloro-2,4-dinitrobenzene cross-coupled with phenyl boronic acid, 1-naphthyl boronic acid, 9-phenanthryl boronic acid. 4-Bromobenzylic alcohol gave (4-isopropylphenyl)methanol on sydnone-palladium complex-catalyzed reaction with isopropyl boronic acid.

Efficient and chemoselective hydrogenation of aldehydes catalyzed by well-defined PN3-pincer manganese(ii) catalyst precursors: An application in furfural conversion

Gholap, Sandeep Suryabhan,Dakhil, Abdullah Al,Chakraborty, Priyanka,Li, Huaifeng,Dutta, Indranil,Das, Pradip K.,Huang, Kuo-Wei

supporting information, p. 11815 - 11818 (2021/11/30)

Well-defined and air-stable PN3-pincer manganese(ii) complexes were synthesized and used for the hydrogenation of aldehydes into alcohols under mild conditions using MeOH as a solvent. This protocol is applicable for a wide range of aldehydes containing various functional groups. Importantly, α,β-unsaturated aldehydes, including ynals, are hydrogenated with the CC double bond/CC triple bond intact. Our methodology was demonstrated for the conversion of biomass derived feedstocks such as furfural and 5-formylfurfural to furfuryl alcohol and 5-(hydroxymethyl)furfuryl alcohol respectively.

Novel palladium nanoparticles supported on mesoporous natural phosphate: Catalytic ability for the preparation of aromatic hydrocarbons from natural terpenes

Mekkaoui, Ayoub Abdelkader,Aberkouks, Abderrazak,Fkhar, Lahcen,Ait Ali, Mustapha,El Firdoussi, Larbi,El Houssame, Soufiane

, (2020/07/24)

Various ratios of palladium nanoparticles supported on mesoporous natural phosphate (Pd@NP) were prepared using the wetness impregnation method. The prepared catalysts were characterized by IR, XRD, CV, SEM, EDX, XRF, TEM and BET analysis. The reduction and preparation of the palladium nanoparticles afford a crystallite size of 10.88 nm. The performance of the synthesized catalyst was investigated in the solvent-free dehydroaromatization of α-, β- and γ-himachalene mixture from Cedrus atlantica oil as a model substrate. In order to achieve an efficient and selective catalysis, the catalytic dehydroaromatization of various terpenes such as limonene, limonaketone, carvone, carveol and perillyl alcohol was studied. The Pd@NP catalyst performed a high catalytic activity, selectivity and recyclability in the terpenes dehydroaromatization reaction.

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