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4-Bromobenzaldehyde is a white crystalline solid that serves as a versatile intermediate in the synthesis of various organic compounds, including agrochemicals and pharmaceuticals.

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  • 1122-91-4 Structure
  • Basic information

    1. Product Name: 4-Bromobenzaldehyde
    2. Synonyms: 4-Brombenzaldehyd;4-bromo-benzaldehyd;Benzaldehyde, p-bromo-;Benzaldehyde,4-bromo-;p-bromo-benzaldehyd;AKOS BBS-00003194;4-BROMOBENZYLALDEHYDE;4-BROMOBENZALDEHYDE
    3. CAS NO:1122-91-4
    4. Molecular Formula: C7H5BrO
    5. Molecular Weight: 185.02
    6. EINECS: 214-365-0
    7. Product Categories: FINE Chemical & INTERMEDIATES;Aromatic Aldehydes & Derivatives (substituted);Benzaldehyde;Benzaldehyde (Building Blocks for Liquid Crystals);Bifunctional Compounds (Building Blocks for Liquid Crystals);Building Blocks for Liquid Crystals;Functional Materials;Aldehydes;C7;Carbonyl Compounds;Pyridines ,Indolines ,Indoles
    8. Mol File: 1122-91-4.mol
    9. Article Data: 582
  • Chemical Properties

    1. Melting Point: 55-58 °C(lit.)
    2. Boiling Point: 66-68°C 2mm
    3. Flash Point: 228 °F
    4. Appearance: White/Crystalline Solid
    5. Density: 1.85 g/cm3
    6. Vapor Pressure: 0.0249mmHg at 25°C
    7. Refractive Index: 1.5727 (estimate)
    8. Storage Temp.: Room temperature.
    9. Solubility: Chloroform, Ethyl Acetate
    10. Water Solubility: INSOLUBLE
    11. Sensitive: Air Sensitive
    12. BRN: 507100
    13. CAS DataBase Reference: 4-Bromobenzaldehyde(CAS DataBase Reference)
    14. NIST Chemistry Reference: 4-Bromobenzaldehyde(1122-91-4)
    15. EPA Substance Registry System: 4-Bromobenzaldehyde(1122-91-4)
  • Safety Data

    1. Hazard Codes: Xn,Xi
    2. Statements: 22-36/37/38-43
    3. Safety Statements: 26-36/37-36/37/39-22
    4. RIDADR: 2811
    5. WGK Germany: 2
    6. RTECS: CU4810000
    7. TSCA: Yes
    8. HazardClass: 6.1(b)
    9. PackingGroup: III
    10. Hazardous Substances Data: 1122-91-4(Hazardous Substances Data)

1122-91-4 Usage

Uses

Used in Pharmaceutical and Agrochemical Industries:
4-Bromobenzaldehyde is used as an intermediate for the preparation of pharmaceuticals and agrochemicals due to its reactivity and ability to form a wide range of derivatives.
Used in the Synthesis of Schiff's Base:
4-Bromobenzaldehyde is used as a precursor and reacts with sulfamethoxazole to prepare Schiff's base, 4-[(4-Bromo-benzylidene)-amino]-N-(5-methyl-isoxazol-3-yl)-benzene sulfonamide, which can be used for the photo stability of polyvinyl chloride (PVC).
Used in Palladium-Catalyzed Arylation:
4-Bromobenzaldehyde plays an important role in palladium-catalyzed monoand bis-arylation of 3,4-(ethylenedioxy)thiophenes, which are important for the development of new materials and compounds.
Used in Cross-Coupling Studies:
4-Bromobenzaldehyde is employed in a cross-coupling study with potassium vinyltrifluoroborate, which is a significant process in the synthesis of various organic compounds and materials.

Synthesis Reference(s)

Journal of the American Chemical Society, 81, p. 4113, 1959 DOI: 10.1021/ja01524a080Tetrahedron Letters, 21, p. 813, 1980 DOI: 10.1016/S0040-4039(00)71512-7

Check Digit Verification of cas no

The CAS Registry Mumber 1122-91-4 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 1,1,2 and 2 respectively; the second part has 2 digits, 9 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 1122-91:
(6*1)+(5*1)+(4*2)+(3*2)+(2*9)+(1*1)=44
44 % 10 = 4
So 1122-91-4 is a valid CAS Registry Number.
InChI:nChI=1/C7H5BrO/c8-7-3-1-6(5-9)2-4-7/h1-5H

1122-91-4 Well-known Company Product Price

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  • (Code)Product description
  • CAS number
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  • Detail
  • TCI America

  • (B0549)  4-Bromobenzaldehyde  >97.0%(GC)

  • 1122-91-4

  • 25g

  • 155.00CNY

  • Detail
  • TCI America

  • (B0549)  4-Bromobenzaldehyde  >97.0%(GC)

  • 1122-91-4

  • 250g

  • 890.00CNY

  • Detail
  • Alfa Aesar

  • (A14237)  4-Bromobenzaldehyde, 98+%   

  • 1122-91-4

  • 25g

  • 404.0CNY

  • Detail
  • Alfa Aesar

  • (A14237)  4-Bromobenzaldehyde, 98+%   

  • 1122-91-4

  • 100g

  • 1146.0CNY

  • Detail
  • Alfa Aesar

  • (A14237)  4-Bromobenzaldehyde, 98+%   

  • 1122-91-4

  • 500g

  • 5010.0CNY

  • Detail

1122-91-4SDS

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 4-Bromobenzaldehyde

1.2 Other means of identification

Product number -
Other names p-Bromobenzaldehyde

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:1122-91-4 SDS

1122-91-4Synthetic route

4-bromobenzenemethanol
873-75-6

4-bromobenzenemethanol

4-bromo-benzaldehyde
1122-91-4

4-bromo-benzaldehyde

Conditions
ConditionsYield
With dinitrogen tetraoxide; ferric nitrate for 0.08h; Ambient temperature; further oxidizing agent, further conditions and solvents;100%
With butyltriphenylphosphonium chlorochromate In acetonitrile for 0.333333h; Heating;100%
With 1H-imidazole; sodium periodate; manganese(III)-porphyrin complex immobilized on polystyrene In water; acetonitrile at 20℃; for 0.75h;100%
(4-bromophenyl)methylenediacetate
55605-27-1

(4-bromophenyl)methylenediacetate

4-bromo-benzaldehyde
1122-91-4

4-bromo-benzaldehyde

Conditions
ConditionsYield
With [NO(1+)*18-crown-6*H(NO3)2(1-)]; silica gel In dichloromethane at 20℃; for 0.0833333h;100%
With caro's acid; silica gel In dichloromethane for 1.4h; Heating;98%
With potassium tert-butylate; 3-Dimethylaminophenol In tetrahydrofuran for 0.0833333h;97%
2-(4-bromophenyl)-1,3-dithiolane
83521-65-7

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

4-bromo-benzaldehyde
1122-91-4

4-bromo-benzaldehyde

Conditions
ConditionsYield
With pyridine hydrogenfluoride; Selectfluor In dichloromethane at 20℃;100%
With bromine; dimethyl sulfoxide In chloroform at 20℃; for 0.0666667h;97%
With silica gel; ferric nitrate In hexane at 50℃; for 0.25h;94%
(E)-1-(4-bromobenzylidene)semicarbazide

(E)-1-(4-bromobenzylidene)semicarbazide

4-bromo-benzaldehyde
1122-91-4

4-bromo-benzaldehyde

Conditions
ConditionsYield
With caro's acid; silica gel In dichloromethane for 0.0833333h; Heating;100%
1-bromo-4-ethenyl-benzene
2039-82-9

1-bromo-4-ethenyl-benzene

4-bromo-benzaldehyde
1122-91-4

4-bromo-benzaldehyde

Conditions
ConditionsYield
With dihydrogen peroxide In water at 75℃; for 6h;100%
With eosin Y; oxygen In dimethyl sulfoxide at 20℃; for 10h; Irradiation; Green chemistry;95%
With oxygen at 110℃; for 12h; Green chemistry;92%
benzaldehyde
100-52-7

benzaldehyde

A

4-bromo-benzaldehyde
1122-91-4

4-bromo-benzaldehyde

B

ortho-bromobenzaldehyde
6630-33-7

ortho-bromobenzaldehyde

Conditions
ConditionsYield
With sulfuric acid; C18H16Br4N2O3V; dihydrogen peroxide; potassium bromide In methanol; water at 20℃; for 2.33333h; Catalytic behavior;A 100%
B n/a
4-bromobenzenemethanol
873-75-6

4-bromobenzenemethanol

nitrobenzene
98-95-3

nitrobenzene

A

4-bromo-benzaldehyde
1122-91-4

4-bromo-benzaldehyde

B

N-(4-bromobenzylidene)aniline
5877-51-0

N-(4-bromobenzylidene)aniline

Conditions
ConditionsYield
With α,α,α-trifluorotoluene; titanium(IV) oxide In dodecane under 750.075 Torr; for 3h; Darkness; Inert atmosphere; Irradiation;A n/a
B 100%
Ethyl 4-bromobenzoate
5798-75-4

Ethyl 4-bromobenzoate

4-bromo-benzaldehyde
1122-91-4

4-bromo-benzaldehyde

Conditions
ConditionsYield
Stage #1: Ethyl 4-bromobenzoate With morpholine; diisobutylaluminium hydride In tetrahydrofuran; hexane at 0℃; for 3.16667h; Inert atmosphere;
Stage #2: With diisobutylaluminium hydride In tetrahydrofuran; hexane at 0℃; for 0.166667h; Inert atmosphere;
99%
With H2SiEt2; C15H27Br2CoN3; potassium tert-butylate In toluene at 50℃; for 12h; Inert atmosphere; Glovebox; Sealed tube;51%
With naphthalene In tetrahydrofuran; hexane at 0℃; for 3h;83 % Chromat.
4-bromobenzenemethanol
873-75-6

4-bromobenzenemethanol

di(p-tolyl) sulfoxide
1774-35-2

di(p-tolyl) sulfoxide

A

di-(p-tolyl)sulfane
620-94-0

di-(p-tolyl)sulfane

B

4-bromo-benzaldehyde
1122-91-4

4-bromo-benzaldehyde

Conditions
ConditionsYield
With per-rhenic acid In toluene for 17h; Reflux;A 99%
B 98%
C16H17BrO2

C16H17BrO2

4-bromo-benzaldehyde
1122-91-4

4-bromo-benzaldehyde

Conditions
ConditionsYield
With silica-OSO3H; silica gel In toluene at 60 - 70℃; for 1h;98%
With tetrachlorosilane; silica gel In toluene at 60 - 70℃; for 1h;92%
With potassium sulfate; potassium hydrogensulfate; potassium peroxomonosulfate; aluminium trichloride In acetonitrile Heating;
4-formylphenylboronic acid,
87199-17-5

4-formylphenylboronic acid,

4-bromo-benzaldehyde
1122-91-4

4-bromo-benzaldehyde

Conditions
ConditionsYield
With N-Bromosuccinimide In acetonitrile at 80℃; for 12h;98%
With 1,10-Phenanthroline; oxygen; potassium bromide; copper(ll) bromide In N,N-dimethyl-formamide at 130℃; for 20h;80%
4-bromobenzaldehyde oxime
25062-46-8, 40979-16-6, 34158-73-1

4-bromobenzaldehyde oxime

4-bromo-benzaldehyde
1122-91-4

4-bromo-benzaldehyde

Conditions
ConditionsYield
With quinolinium dichromate(VI) In acetonitrile for 0.5h; Heating;97%
With potassium permanganate; 1-n-butyl-3-methylimidazolim bromide at 20℃; for 0.283333h; Ionic liquid; chemoselective reaction;97%
With aluminum(III) nitrate nonahydrate; sodium bromide In dichloromethane at 20℃; for 6.75h;96%
4-bromobenzaldehyde phenylhydrazone
16917-42-3

4-bromobenzaldehyde phenylhydrazone

4-bromo-benzaldehyde
1122-91-4

4-bromo-benzaldehyde

Conditions
ConditionsYield
With quinolinium dichromate(VI) In acetonitrile for 1h; Heating;97%
With water; silica gel; bis(trimethylsilyl)chromate In chloroform for 0.15h; Heating;97%
With quinolinium dichromate In acetonitrile for 0.266667h; Heating;92%
(4-bromobenzyloxy)trimethylsilane
86605-93-8

(4-bromobenzyloxy)trimethylsilane

4-bromo-benzaldehyde
1122-91-4

4-bromo-benzaldehyde

Conditions
ConditionsYield
With NTPPPODS In acetonitrile for 0.05h; Reflux;97%
With cetyltrimethylammonium peroxodisulphate In acetonitrile for 0.166667h; Reflux;95%
With zinc dichromate(VI) at 20℃;93%
4-bromo-N,N-diethylbenzamide
5892-99-9

4-bromo-N,N-diethylbenzamide

4-bromo-benzaldehyde
1122-91-4

4-bromo-benzaldehyde

Conditions
ConditionsYield
With zirconocene dichloride; lithium tri-t-butoxyaluminum hydride In tetrahydrofuran at 20℃; for 0.0333333h; Product distribution / selectivity;96%
With zirconocene dichloride; lithium tri-t-butoxyaluminum hydride In tetrahydrofuran at 20℃; for 0.0333333h; Solvent; Inert atmosphere;96%
4-bromo-N-isopropyl-benzamide
336182-29-7

4-bromo-N-isopropyl-benzamide

4-bromo-benzaldehyde
1122-91-4

4-bromo-benzaldehyde

Conditions
ConditionsYield
Stage #1: 4-bromo-N-isopropyl-benzamide With 2-fluoropyridine; trifluoromethylsulfonic anhydride In dichloromethane at 0℃; for 0.333333h; Inert atmosphere;
Stage #2: With 1,1,3,3-Tetramethyldisiloxane In dichloromethane at 0 - 20℃; for 6.16667h; Inert atmosphere;
Stage #3: With hydrogenchloride In dichloromethane; water at 20℃; Inert atmosphere;
96%
4-bromobenzenecarbonitrile
623-00-7

4-bromobenzenecarbonitrile

4-bromo-benzaldehyde
1122-91-4

4-bromo-benzaldehyde

Conditions
ConditionsYield
With lithium diisobutylmorpholinoaluminum hydride In tetrahydrofuran; hexane at 0℃; for 0.5h;95%
With calcium bis(hypophosphite); calcium acetate; nickel(II) acetate tetrahydrate In ethanol; water at 100℃; for 23h; Sealed tube;90%
With sodium hydride; zinc(II) chloride In tetrahydrofuran; mineral oil at 40℃; for 0.5h; Inert atmosphere; Sealed tube;80%
With hydrogenchloride; diethyl ether; tin(ll) chloride anschliessenden Hydrolyse;
1.4-dibromobenzene
106-37-6

1.4-dibromobenzene

N,N-dimethyl-formamide
68-12-2, 33513-42-7

N,N-dimethyl-formamide

4-bromo-benzaldehyde
1122-91-4

4-bromo-benzaldehyde

Conditions
ConditionsYield
Stage #1: 1.4-dibromobenzene With n-butyllithium; isopropylmagnesium chloride In tetrahydrofuran; hexane at 0 - 5℃; for 1h;
Stage #2: N,N-dimethyl-formamide In tetrahydrofuran at 0℃; for 1h; Further stages.;
95%
Stage #1: 1.4-dibromobenzene With tri-n-butyllithium magnesate complex In toluene at 0℃; for 5h;
Stage #2: N,N-dimethyl-formamide In toluene at 0℃; for 0.5h;
Stage #3: With citric acid at 20℃;
84%
Stage #1: 1.4-dibromobenzene With n-butyllithium In diethyl ether; hexane at -78℃; for 3.25h;
Stage #2: N,N-dimethyl-formamide In diethyl ether; hexane at -78 - 23℃; for 2.5h;
72%
N-(4-bromobenzylidene)aniline
5877-51-0

N-(4-bromobenzylidene)aniline

4-bromo-benzaldehyde
1122-91-4

4-bromo-benzaldehyde

Conditions
ConditionsYield
With tetrachlorosilane In acetonitrile at 20℃; for 6h;95%
2-((4-bromobenzyl)oxy)tetrahydro-2H-pyran
17100-68-4

2-((4-bromobenzyl)oxy)tetrahydro-2H-pyran

4-bromo-benzaldehyde
1122-91-4

4-bromo-benzaldehyde

Conditions
ConditionsYield
With N-Bromosuccinimide; β‐cyclodextrin In acetone at 20℃; for 0.5h;95%
With NTPPPODS In acetonitrile for 0.133333h; Reflux;93%
With potassium permanganate; tetrachlorosilane In acetonitrile at 20℃; for 0.116667h;90%
(E)-1-(4-bromobenzylidene)-2-phenylhydrazine
16917-42-3

(E)-1-(4-bromobenzylidene)-2-phenylhydrazine

4-bromo-benzaldehyde
1122-91-4

4-bromo-benzaldehyde

Conditions
ConditionsYield
With caro's acid; silica gel In dichloromethane for 1.41667h; Heating;95%
p-bromobenzaldehyde 1,3-dioxolane
10602-01-4

p-bromobenzaldehyde 1,3-dioxolane

trifluoroacetic acid
76-05-1

trifluoroacetic acid

A

2-hydroxyethyl trifluoroacetate
667-32-3

2-hydroxyethyl trifluoroacetate

B

4-bromo-benzaldehyde
1122-91-4

4-bromo-benzaldehyde

Conditions
ConditionsYield
In chloroform at 25℃; for 10h;A n/a
B 95%
2-(4-bromobenzylidene)hydrazinecarboxamide
120445-43-4, 14066-66-1

2-(4-bromobenzylidene)hydrazinecarboxamide

4-bromo-benzaldehyde
1122-91-4

4-bromo-benzaldehyde

Conditions
ConditionsYield
With quinolinium monofluorochromate(VI) In acetonitrile for 2.5h; Heating;94%
With benzyltriphenylphosphonium peroxodisulfate In acetonitrile for 0.166667h; Heating;93%
With NTPPPODS In water; acetonitrile for 0.333333h; Reflux;93%
(4-Bromo-phenyl)-phenylamino-methanesulfonic acid; compound with methylamine
114021-98-6

(4-Bromo-phenyl)-phenylamino-methanesulfonic acid; compound with methylamine

A

4-bromo-benzaldehyde
1122-91-4

4-bromo-benzaldehyde

B

(4-Bromo-phenyl)-phenylamino-methanesulfonic acid; compound with phenylamine
113360-52-4

(4-Bromo-phenyl)-phenylamino-methanesulfonic acid; compound with phenylamine

Conditions
ConditionsYield
With hydrogenchloride for 24h;A n/a
B 94%
(E)-N-(4-(4-bromophenyl)but-3-en-1-yn-1-yl)-N-methylmethanesulfonamide
1562381-84-3

(E)-N-(4-(4-bromophenyl)but-3-en-1-yn-1-yl)-N-methylmethanesulfonamide

Nitrosobenzene
586-96-9

Nitrosobenzene

A

N-methyl-N-(methylsulfonyl)-N'-phenylpropiolimidamide
1562381-21-8

N-methyl-N-(methylsulfonyl)-N'-phenylpropiolimidamide

B

4-bromo-benzaldehyde
1122-91-4

4-bromo-benzaldehyde

Conditions
ConditionsYield
With zinc trifluoromethanesulfonate In 1,2-dichloro-ethane at 60℃; for 2h; Inert atmosphere;A 94%
B 94%
1-(4-bromophenyl)-2,2,2-trichloroethan-1-ol
21757-86-8

1-(4-bromophenyl)-2,2,2-trichloroethan-1-ol

A

p-bromophenyl-α-chloroacetic acid
35549-94-1

p-bromophenyl-α-chloroacetic acid

B

4-bromo-benzaldehyde
1122-91-4

4-bromo-benzaldehyde

Conditions
ConditionsYield
With potassium hydroxide In water at 0℃; for 48h;A 93%
B 0.34 g
With potassium hydroxide In water at 0℃; for 48h; Product distribution;A 93%
B 0.34 g
2-(4-bromophenyl)-1,3-oxathiolane
147441-51-8, 147441-52-9, 77853-37-3

2-(4-bromophenyl)-1,3-oxathiolane

4-bromo-benzaldehyde
1122-91-4

4-bromo-benzaldehyde

Conditions
ConditionsYield
With tetrafluoroboric acid; mercury(II) oxide In tetrahydrofuran Ambient temperature;93%
With tetrafluoroboric acid; mercury(II) oxide In tetrahydrofuran Product distribution; Ambient temperature; various 1,3-oxathiolanes;93%
With methanol; sodium tetrahydroborate; nickel(II) chloride hexahydrate at 20℃; for 1.5h;90%
With eosin Y disodium salt In acetonitrile at 20℃; for 3h; Catalytic behavior; Reagent/catalyst; Solvent; Irradiation;80%
p-bromobenzyl chloride
589-17-3

p-bromobenzyl chloride

4-bromo-benzaldehyde
1122-91-4

4-bromo-benzaldehyde

Conditions
ConditionsYield
With water; sodium hydroxide at 20℃; for 0.0666667h; Microwave irradiation;93%
With (NH4)4[ZnMo6O18(OH)6]; oxygen In water; acetonitrile at 60℃; under 760.051 Torr; for 12h;87%
With dihydrogen peroxide; vanadia; Aliquat 336 In water for 15h; Heating;85%
1,2-bis(4-bromophenyl)ethane-1,2-diol
37580-82-8, 126082-50-6, 24133-54-8

1,2-bis(4-bromophenyl)ethane-1,2-diol

4-bromo-benzaldehyde
1122-91-4

4-bromo-benzaldehyde

Conditions
ConditionsYield
With dimanganese decacarbonyl In toluene at 120℃; Sealed tube;93%
With oxygen; cetyltrimethylammonim bromide In water at 20℃; under 760.051 Torr; for 5h; Irradiation; Green chemistry;85%
With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In trifluoroacetic acid at 30℃; for 0.1h;82%
With dichlorobis(dimethylsulfoxide)dioxomolybdenum(VI); dimethyl sulfoxide at 130℃; for 0.166667h; Sealed tube; Microwave irradiation; Green chemistry; chemoselective reaction;91 %Spectr.
With oxygen In methanol at 140℃; under 2250.23 Torr; for 3h; Autoclave;
ethylene glycol
107-21-1

ethylene glycol

4-bromo-benzaldehyde
1122-91-4

4-bromo-benzaldehyde

p-bromobenzaldehyde 1,3-dioxolane
10602-01-4

p-bromobenzaldehyde 1,3-dioxolane

Conditions
ConditionsYield
With toluene-4-sulfonic acid In toluene at 100 - 110℃; for 5h;100%
With toluene-4-sulfonic acid In toluene at 110℃; for 12h;100%
With toluene-4-sulfonic acid In toluene Reflux;98%
4-bromo-benzaldehyde
1122-91-4

4-bromo-benzaldehyde

N-Phenylhydroxylamine
100-65-2

N-Phenylhydroxylamine

α-(4-bromo)-N-phenylnitrone
24720-81-8, 94664-73-0

α-(4-bromo)-N-phenylnitrone

Conditions
ConditionsYield
With methanesulfonic acid In ethanol at 20℃;100%
With hydrogenchloride In ethanol; water for 0.0833333h;85%
With clay for 2h; Ambient temperature;75%
4-bromo-benzaldehyde
1122-91-4

4-bromo-benzaldehyde

4-bromobenzenemethanol
873-75-6

4-bromobenzenemethanol

Conditions
ConditionsYield
With hydrogen; Et4N In 1,2-dimethoxyethane at 100℃; under 38000 Torr; for 13h;100%
With tri-n-butyl-tin hydride In methanol; diethyl ether for 4h; Reduction; Heating;100%
With hydrogen; phosphotungstic acid 44-hydrate; [Fe(C5H4P(i-Pr)2)2Rh(C8H12)]BF4 In water; isopropyl alcohol at 20℃; under 5171.62 Torr; for 16h;100%
4-Bromophenylacetonitrile
16532-79-9

4-Bromophenylacetonitrile

4-bromo-benzaldehyde
1122-91-4

4-bromo-benzaldehyde

1,2-bis(4-bromophenyl)-1-cyanovinylene
33731-82-7

1,2-bis(4-bromophenyl)-1-cyanovinylene

Conditions
ConditionsYield
With potassium hydroxide In ethanol at 20℃; for 1.5h;100%
With sodium hydroxide In ethanol at 20℃; for 1h;91%
With sodium hydroxide In methanol
4-bromo-benzaldehyde
1122-91-4

4-bromo-benzaldehyde

acrylic acid methyl ester
292638-85-8

acrylic acid methyl ester

methyl (2E)-3-(4-formylphenyl)acrylate
7560-50-1, 71093-79-3, 58045-41-3

methyl (2E)-3-(4-formylphenyl)acrylate

Conditions
ConditionsYield
With tetrabutylammomium bromide; C12H12N4O2Pd(2+)*2Cl(1-); potassium carbonate In water at 75 - 80℃; for 0.5h; Solvent; Heck Reaction; Sonication; Green chemistry;100%
With polystyrene-supported palladacycle catalyst; sodium acetate In N,N-dimethyl acetamide at 100℃; for 10h; Heck reaction;99%
With sodium acetate; palladium diacetate In 1-methyl-pyrrolidin-2-one at 115 - 120℃; for 1h; Heck reaction; Inert atmosphere;99%
4-bromo-benzaldehyde
1122-91-4

4-bromo-benzaldehyde

phenylacetylene
536-74-3

phenylacetylene

4-(phenylethynyl)benzaldehyde
57341-98-7

4-(phenylethynyl)benzaldehyde

Conditions
ConditionsYield
Stage #1: 4-bromo-benzaldehyde With 5% Pd/C; triethylamine; triphenylphosphine for 0.0833333h; Sonogashira Cross-Coupling; Sealed tube; Sonication;
Stage #2: phenylacetylene for 3h; Sealed tube;
100%
With water; potassium carbonate In 1-methyl-pyrrolidin-2-one at 135℃; for 24h; Catalytic behavior; Sonogashira Cross-Coupling;99%
With C19H16ClNPdS; potassium carbonate In N,N-dimethyl-formamide at 90℃; for 1h; Solvent; Reagent/catalyst; Sonogashira Cross-Coupling;99%
4-bromo-benzaldehyde
1122-91-4

4-bromo-benzaldehyde

trimethyl orthoformate
149-73-5

trimethyl orthoformate

1,1-dimethoxy-1-(4-bromophenyl)methane
24856-58-4

1,1-dimethoxy-1-(4-bromophenyl)methane

Conditions
ConditionsYield
Yb-Amberlyst XN-1010 In dichloromethane100%
With Yb(III)-coordinated adamantane-based porous polymer In methanol at 20℃; for 12h; Catalytic behavior; Reagent/catalyst;100%
With amberlyst-15 In acetonitrile for 2.5h; electroosmos;99.7%
3-acetylcoumarin
3949-36-8

3-acetylcoumarin

4-bromo-benzaldehyde
1122-91-4

4-bromo-benzaldehyde

1-(3'-coumarinyl)-3-(4''-bromophenyl)-2-propen-1-one
107126-88-5

1-(3'-coumarinyl)-3-(4''-bromophenyl)-2-propen-1-one

Conditions
ConditionsYield
With potassium hydroxide In ethanol Reflux;100%
With ZnS/g-C3N4 nanocomposite In ethanol for 1h; Claisen-Schmidt Condensation; Reflux; Green chemistry;91%
With piperidine In ethanol Claisen-Schmidt Condensation; Reflux;75%
4-methoxy-aniline
104-94-9

4-methoxy-aniline

4-bromo-benzaldehyde
1122-91-4

4-bromo-benzaldehyde

N-(4-bromobenzylidene)-4-methoxyaniline
28115-12-0

N-(4-bromobenzylidene)-4-methoxyaniline

Conditions
ConditionsYield
for 6h; Ambient temperature;100%
With sulfuric acid In neat (no solvent) Microwave irradiation; Sealed tube; Green chemistry;92%
In dichloromethane at 20℃; for 16h; Inert atmosphere; Molecular sieve;92%
4-methoxy-aniline
104-94-9

4-methoxy-aniline

4-bromo-benzaldehyde
1122-91-4

4-bromo-benzaldehyde

(E)-1-(4-bromophenyl)-N-(4-methoxyphenyl)methanimine
28115-12-0

(E)-1-(4-bromophenyl)-N-(4-methoxyphenyl)methanimine

Conditions
ConditionsYield
With magnesium sulfate In dichloromethane Inert atmosphere;100%
With tris(2,2,2-trifluoroethyl) borate In tetrahydrofuran at 20℃; for 2h; Inert atmosphere;92%
In ethanol at 20℃; Inert atmosphere;81%
tert-Butyl acrylate
1663-39-4

tert-Butyl acrylate

4-bromo-benzaldehyde
1122-91-4

4-bromo-benzaldehyde

(E)-t-butyl 4-formylcinnamate
208036-26-4

(E)-t-butyl 4-formylcinnamate

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 6h; Heck-Mizoroki reaction;100%
With palladium diacetate; triethylamine; tris-(o-tolyl)phosphine Heating;91%
With palladium on silica; triethylamine In N,N-dimethyl-formamide for 0.2h; Heck Reaction; Microwave irradiation; Green chemistry;89%
6-chloro-2-[1-methyl-2-(2-thienylmethylene)hydrazino]quinoxaline-4-oxide
126983-41-3

6-chloro-2-[1-methyl-2-(2-thienylmethylene)hydrazino]quinoxaline-4-oxide

4-bromo-benzaldehyde
1122-91-4

4-bromo-benzaldehyde

2-<2-(p-bromobenzylidene)-1-methylhydrazino>-6-chloroquinoxaline 4-oxide
128960-28-1

2-<2-(p-bromobenzylidene)-1-methylhydrazino>-6-chloroquinoxaline 4-oxide

Conditions
ConditionsYield
In N,N-dimethyl-formamide for 1h; Heating;100%
6-chloro-2-[1-methyl-2-(2-thienylmethylene)hydrazino]quinoxaline-4-oxide
126983-41-3

6-chloro-2-[1-methyl-2-(2-thienylmethylene)hydrazino]quinoxaline-4-oxide

4-bromo-benzaldehyde
1122-91-4

4-bromo-benzaldehyde

2-<2-(p-bromobenzylidene)-1-methylhydrazino>-6-chloroquinoxaline 4-oxide
128960-28-1

2-<2-(p-bromobenzylidene)-1-methylhydrazino>-6-chloroquinoxaline 4-oxide

Conditions
ConditionsYield
In N,N-dimethyl-formamide for 1h; Heating;100%
4-bromo-benzaldehyde
1122-91-4

4-bromo-benzaldehyde

phenylazomalonamamidine hydrochloride
6285-64-9

phenylazomalonamamidine hydrochloride

2,8-Bis-(4-bromo-phenyl)-1,7-dihydro-purin-6-one
81976-29-6

2,8-Bis-(4-bromo-phenyl)-1,7-dihydro-purin-6-one

Conditions
ConditionsYield
at 170℃; for 1h;100%
4-bromo-benzaldehyde
1122-91-4

4-bromo-benzaldehyde

phenylazomalonamamidine hydrochloride
6285-64-9

phenylazomalonamamidine hydrochloride

2-{N-[1-(4-Bromo-phenyl)-meth-(E)-ylidene]-carbamimidoyl}-2-phenylazo-acetamide; hydrochloride
81990-66-1

2-{N-[1-(4-Bromo-phenyl)-meth-(E)-ylidene]-carbamimidoyl}-2-phenylazo-acetamide; hydrochloride

Conditions
ConditionsYield
at 120℃; for 0.25h;100%
4-bromo-benzaldehyde
1122-91-4

4-bromo-benzaldehyde

tert-butylamine
75-64-9

tert-butylamine

N-(4-bromobenzylidene)-2-methylpropan-2-amine
62058-76-8

N-(4-bromobenzylidene)-2-methylpropan-2-amine

Conditions
ConditionsYield
In dichloromethane at 20℃; for 4h;100%
With 4 A molecular sieve for 24h; Ambient temperature;97%
With titanium tetrachloride In diethyl ether; toluene at 0℃; for 0.25h; Glovebox; Inert atmosphere; Schlenk technique;86%
at 100℃; Schlenk technique;
In 1,2-dichloro-ethane at 70℃; for 4h; Glovebox;
4-bromo-benzaldehyde
1122-91-4

4-bromo-benzaldehyde

methylamine
74-89-5

methylamine

1-(4-bromophenyl)-N-methylmethanimine
35003-56-6

1-(4-bromophenyl)-N-methylmethanimine

Conditions
ConditionsYield
In methanol; dichloromethane for 18h; Molecular sieve;100%
at 80℃; for 1h;
In methanol; dichloromethane at 20℃; for 12h; Molecular sieve; Inert atmosphere;
4-bromo-benzaldehyde
1122-91-4

4-bromo-benzaldehyde

ethyl (triphenylphosphoranylidene)acetate
1099-45-2

ethyl (triphenylphosphoranylidene)acetate

ethyl (E)-3-(4-bromophenyl)-2-propenoate
24393-53-1, 136265-11-7, 15795-20-7

ethyl (E)-3-(4-bromophenyl)-2-propenoate

Conditions
ConditionsYield
In dichloromethane at 22℃; for 16h; Wittig reaction;100%
In toluene Wittig reaction;100%
In toluene at 20℃; for 0.5h;97%
4-bromo-benzaldehyde
1122-91-4

4-bromo-benzaldehyde

trimethylsilylacetylene
1066-54-2

trimethylsilylacetylene

4-[(trimethylsilyl)ethynyl]bezaldehyde
77123-57-0

4-[(trimethylsilyl)ethynyl]bezaldehyde

Conditions
ConditionsYield
With copper(l) iodide; diisopropylamine; polymer-supp. 11-(2-[Pd(OAc)2]-1-Mes-3-imidazolyl)undecanol In tetrahydrofuran at 20℃; for 2h; Sonogashira coupling;100%
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine In tetrahydrofuran at 20℃; Inert atmosphere;100%
Stage #1: 4-bromo-benzaldehyde With 5% Pd/C; triethylamine; triphenylphosphine for 0.0833333h; Sonogashira Cross-Coupling; Sealed tube; Sonication;
Stage #2: trimethylsilylacetylene for 3h; Sealed tube;
100%
4-bromo-benzaldehyde
1122-91-4

4-bromo-benzaldehyde

trimethyleneglycol
504-63-2

trimethyleneglycol

2-(4-bromophenyl)-1,3-dioxane
61568-51-2

2-(4-bromophenyl)-1,3-dioxane

Conditions
ConditionsYield
With Amberlyst 15 In benzene for 3h; Heating;100%
With boron trifluoride diethyl etherate In toluene for 4.5h; Acetalization; Heating;96%
With boron trifluoride diethyl etherate In toluene at 100℃; for 4.5h;96%
4-bromo-benzaldehyde
1122-91-4

4-bromo-benzaldehyde

4-bromobenzaldehyde Oxime
25062-46-8, 34158-73-1, 40979-16-6

4-bromobenzaldehyde Oxime

Conditions
ConditionsYield
With pyridine; hydroxylamine hydrochloride In ethanol100%
With hydroxylamine hydrochloride In ethanol100%
With hydroxylamine hydrochloride; sodium acetate In methanol; water Reflux;100%
4-bromo-benzaldehyde
1122-91-4

4-bromo-benzaldehyde

1,2-bis(4-bromophenyl)-2-hydroxyethan-1-one
4254-18-6

1,2-bis(4-bromophenyl)-2-hydroxyethan-1-one

Conditions
ConditionsYield
With 3-ethyl-5-(2-hydroxyethyl)-4-methyl-1,3-thiazolium bromide; triethylamine In ethanol at 20℃; for 60h;100%
With sodium cyanide In ethanol; water for 0.333333h; Heating;91.8%
With sodium cyanide In methanol; water for 0.5h; Reflux;90%
acrylic acid n-butyl ester
141-32-2

acrylic acid n-butyl ester

4-bromo-benzaldehyde
1122-91-4

4-bromo-benzaldehyde

butyl (E)-4-formylcinnamate
169479-49-6

butyl (E)-4-formylcinnamate

Conditions
ConditionsYield
With 2-n-butyl-1,1,1,3,3-tetramethylguanidine acetate; palladium dichloride at 140℃; for 0.25h;100%
With sodium acetate In ISOPROPYLAMIDE100%
With sodium acetate In ISOPROPYLAMIDE100%
styrene
292638-84-7

styrene

4-bromo-benzaldehyde
1122-91-4

4-bromo-benzaldehyde

4-styrylbenzaldehyde
32555-96-7

4-styrylbenzaldehyde

Conditions
ConditionsYield
With triethylamine; tris-(o-tolyl)phosphine In N,N-dimethyl-formamide at 150℃; for 24h; Catalytic behavior; Reagent/catalyst; Heck Reaction; Inert atmosphere;100%
With 2-n-butyl-1,1,1,3,3-tetramethylguanidine acetate; palladium dichloride at 140℃; for 0.25h;99%
With 1,3-bis-(2-ethoxybenzyl)-3,4,5,6-tetrahydropyrimidinium chloride; palladium diacetate; potassium carbonate In water; N,N-dimethyl-formamide at 80℃; for 4h; Heck reaction; stereoselective reaction;99%
4-bromo-benzaldehyde
1122-91-4

4-bromo-benzaldehyde

1,2-bis(4-bromophenyl)ethane-1,2-diol
37580-82-8, 126082-50-6, 24133-54-8

1,2-bis(4-bromophenyl)ethane-1,2-diol

Conditions
ConditionsYield
With aluminium; potassium hydroxide In methanol at 0℃; for 1h; Inert atmosphere;100%
With 2,6-dimethyl-pyridine-3,5-dicarboxylic acid diethyl ester; Cu(5-(4-fluorosulfonyl)amino-3-(2-pyridyl)-pyrazole)((rac)-2,2′-bis(diphenylphosphino)-1,1′-binaphthalene)BF4 In tetrahydrofuran for 18h; Pinacol Rearrangement; Irradiation;99%
With bis(cyclopentadienyl)-titanium(III) chloride In tetrahydrofuran at -78 - 20℃;91%
4-bromo-benzaldehyde
1122-91-4

4-bromo-benzaldehyde

malononitrile
109-77-3

malononitrile

4-bromobenzylidenemalononitrile
2826-24-6

4-bromobenzylidenemalononitrile

Conditions
ConditionsYield
With polyethylenimine functionalized Si-MCM-41 grafted on surfacemodified graphene oxide In tetrahydrofuran; benzene for 0.5h; Knoevenagel Condensation;100%
With 3-(1-piperazino)propyl functionalised silica gel In acetonitrile Knoevenagel condensation;99.9%
With 3-(1-piperazino)propyl-functionalised silica gel In acetonitrile Knoevenagel reaction; electroosmotic flow;99.9%
1-amino-naphthalene
134-32-7

1-amino-naphthalene

4-bromo-benzaldehyde
1122-91-4

4-bromo-benzaldehyde

[1-(4-Bromo-phenyl)-meth-(E)-ylidene]-naphthalen-1-yl-amine
116401-74-2

[1-(4-Bromo-phenyl)-meth-(E)-ylidene]-naphthalen-1-yl-amine

Conditions
ConditionsYield
for 2h; Ambient temperature;100%
In benzene Reflux;

1122-91-4Relevant articles and documents

Regioselective radical aminofluorination of styrenes

Zhang, Hongwei,Song, Yongcheng,Zhao, Jinbo,Zhang, Jingping,Zhang, Qian

, p. 11079 - 11083 (2014)

The copper-catalyzed radical aminofluorination of styrenes with N-fluorobenzenesulfonimide (NFSI) is realized with high regioselectivity thus affording aminofluorination products with regioselectivities opposite that of the palladium-catalyzed and noncatalyzed processes. Preliminary mechanistic studies suggested the reaction went through a radical pathway and was supported by DFT calculations. In these reactions NFSI is utilized as both a radical nitrogen source and radical fluorine source thus rendering it an attractive reagent.

Microwave-assisted chemoselective regeneration of carbonyl compounds from oximes by silica chromate/WET SiO2 under solvent-free conditions

Zolfigol, Mohammad Ali,Khazaei, Ardeshir,Ghorbani-Choghamarani, Arash,Rostami, Amin

, p. 2453 - 2458 (2006)

The regeneration of carbonyl compounds from oximes were performed by using silica chromate and wet SiO2 (w/w 50%) under microwave irradiation and solvent-free conditions with excellent yields. Copyright Taylor & Francis Group, LLC.

A mild and efficient method for the oxidation of benzylic alcohols by two-phase electrolysis

Raju, Thasan,Manivasagan, Sankar,Revathy, Balachandran,Kulangiappar, Kumarasamy,Muthukumaran, Arunachalam

, p. 3681 - 3684 (2007)

Electrochemical oxidation of benzylic and substituted benzylic alcohols by two-phase electrolysis yields the corresponding aldehydes as products. The reaction was carried out in a single compartment cell with platinum electrodes at room temperature in chloroform using an aqueous sodium bromide solution (25%) containing a catalytic amount of HBr. The two-phase electrolysis resulted in high yields (74-96%) of benzaldehyde from primary alcohols and secondary alcohols were oxidized to the corresponding ketone but only in low yields under these conditions.

Novel Schiff base Mn(III) and Co(II) complexes supported on Co nanoparticles: Efficient and recyclable magnetic nanocatalysts for alcohol oxidation

Keypour, Hassan,Saremi, Shokoufeh Ghahri,Veisi, Hojat,Azadbakht, Reza

, p. 77020 - 77029 (2016)

In this study, efficient and highly selective heterogeneous catalysts were developed by immobilization of manganese and cobalt Schiff base complexes on Co magnetite nanoparticles (MNPs). Firstly, Co@SiO2 core-shell nanoparticles were synthesized through a one-pot reaction. Secondly, the Co@SiO2 was amino-functionalized using 3-aminopropyl triethoxysilane and then Schiff base ligand Co@SiO2[(EtO)3Si-L2] was obtained by the reaction of the amino-functionalized nanoparticles with the dialdehyde of 1,2-bis(2-formyl naphthoxy methyl)benzene. Finally, Co@SiO2[(EtO)3Si-L2]/M (M = Mn(iii) and Co(ii)) were successfully synthesized. These surface-modified nanoparticles were characterized using various techniques such as TEM, XRD, TGA, SEM, VSM, XPS, EDX and FT-IR. The catalytic activities of the prepared catalysts were investigated by employing them in the oxidation of various aromatic alcohols with an environmentally friendly oxidant under mild conditions. The catalysts can be readily recovered and reused in at least 5 consecutive cycles without significant leaching and loss their catalytic activity.

Zinc Bismuthate Zn(BiO3)2. I. A Useful Oxidizing Agent for the Efficient Oxidation of Organic Compounds

Firouzabadi, Habib,Mohammadpour-Baltork, Iraj

, p. 1131 - 1134 (1992)

Zinc bismuthate is an easily prepared and a stable compound.It could be used as an oxidant in organic solvents under aprotic or in the presence of a catalytic amount of a protic solvent.Primary and secondary saturated, allylic, and benzylic alcohols are converted to their carbonyl compounds in high yields.Mildness of the reagent is shown by the oxidation of thiols to their disulfides in excellent yields.Thioethers are also oxidized to their corresponding sulfoxides in good yields.

Cerium-Complex-Catalyzed Oxidation of Arylmethanols under Atmospheric Pressure of Dioxygen and Its Mechanism through a Side-On μ-Peroxo Dicerium(IV) Complex

Paul, Mitali,Shirase, Satoru,Morimoto, Yuma,Mathey, Laurent,Murugesapandian, Balasubramanian,Tanaka, Shinji,Itoh, Shinobu,Tsurugi, Hayato,Mashima, Kazushi

, p. 4008 - 4014 (2016)

A new CeIV complex [Ce{NH(CH2CH2N=CHC6H2-3,5-(tBu)2-2-O)2}(NO3)2] (1), bearing a dianionic pentadentate ligand with an N3O2 donor set, has been prepared by treating (NH4)2Ce(NO3)6 with the sodium salt of ligand L1. Complex 1 in the presence of TEMPO and 4 ? molecular sieves (MS4 A) has been found to serve as a catalyst for the oxidation of arylmethanols using dioxygen as an oxidant. We propose an oxidation mechanism based on the isolation and reactivity study of a trivalent cerium complex [Ce{NH(CH2CH2N=CHC6H2-3,5-(tBu)2-2-O)2}(NO3)(THF)] (2), its side-on μ-O2 adduct [Ce{NH(CH2CH2N=CHC6H2-3,5-(tBu)2-2-O)2}(NO3)]2(μ-η2:η2-O2) (3), and the hydroxo-bridged CeIV complex [Ce{NH(CH2CH2N=CHC6H2-3,5-(tBu)2-2-O)2}(NO3)]2(μ-OH)2 (4) as key intermediates during the catalytic cycle. Complex 2 was synthesized by reduction of 1 with 2,5-dimethyl-1,4-bis(trimethylsilyl)-1,4-diazacyclohexadiene. Bubbling O2 into a solution of 2 resulted in formation of the peroxo complex 3. This provides the first direct evidence for cerium-catalyzed oxidation of alcohols under an O2 atmosphere. Cerium-catalyzed alcohol oxidation: A new CeIV complex [Ce{NH(CH2CH2N=CHC6H2-3,5-(tBu)2-2-O)2}(NO3)2] (1) has been shown to serve as a catalyst for the oxidation of arylmethanols using dioxygen as an oxidant in the presence of TEMPO and molecular sieves MS4 A (see scheme). CeIII complex 2, obtained by reduction of 1 with 2,5-dimethyl-1,4-bis(trimethylsilyl)-1,4-diazacyclohexadiene, reacted with O2 to give the peroxo complex 3. This provides the first direct evidence for operation of the peroxo mechanism in the cerium-catalyzed oxidation of alcohols under O2 atmosphere.

Synthetic utility of iodic acid in the oxidation of benzylic alcohols to aromatic aldehydes and ketones

Imai, Sho,Togo, Hideo

, p. 6948 - 6954 (2016)

Various primary and secondary benzylic alcohols were efficiently oxidized to aromatic aldehydes and aromatic ketones with iodic acid in DMF at 60?°C for 2?h and with iodic acid in the presence of TEMPO (5?mol?%) in DMF at room temperature, respectively. The former method was effective for the oxidation of sterically hindered alcohols at 60?°C and the latter method was effective for the oxidation of less sterically hindered alcohols at room temperature.

Oxidations with IBX: Benzyl halides to carbonyl compounds, and the one-pot conversion of olefins to 1,2-diketones

Moorthy, Jarugu Narasimha,Singhal, Nidhi,Senapati, Kalyan

, p. 1757 - 1761 (2006)

A variety of benzyl halides were converted to the corresponding aldehydes/ketones in respectable yields by IBX in DMSO at 65°C. The bromohydrin reaction of olefins using NBS-H2O in DMSO can be nicely adapted to IBX-mediated oxidation of benzyl halides in such a way that olefins are converted to the corresponding 1,2-diketones in good isolated yields in one-pot.

gem-Difluorination of 2,2-diaryl-1,3-dithiolanes by Selectfluor and pyridinium polyhydrogen fluoride

Reddy, V. Prakash,Alleti, Ramesh,Perambuduru, Meher K.,Welz-Biermann, Urs,Buchholz, Herwig,Prakash, G. K. Surya

, p. 654 - 656 (2005)

2,2-Diaryl-1,3-dithiolanes, readily obtainable from diaryl ketones, were transformed into the corresponding gem-difluoro compounds using a novel reagent combination involving Selectfluor and pyridinium polyhydrogen fluoride (PPHF) under mild conditions in moderate to good yields. The Royal Society of Chemistry 2005.

"Click Chemistry" Mediated Functional Microporous Organic Nanotube Networks for Heterogeneous Catalysis

Yu, Wei,Zhou, Minghong,Wang, Tianqi,He, Zidong,Shi, Buyin,Xu, Yang,Huang, Kun

, p. 5776 - 5779 (2017)

The synthesis of azide functional microporous organic nanotube networks (N3-MONNs) via a Friedel-Crafts hyper-cross-linking reaction is reported. Subsequently, a general method for obtaining heterogeneous catalysts through a Cu-catalyzed alkyne-azide reaction is presented. The small-molecule catalysts such as 2,2,6,6,-tetramethylpiperidine-1-oyl and 4-(N,N-dimethylamino)pyridine can be anchored into the MONNs. Owing to the hierarchically porous structure and high surface area, these catalysts show high activity in selective oxidation of alcohols and acylation reaction, respectively.

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