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555-16-8 Usage

Chemical Properties

YELLOW TO BROWN CRYSTALLINE POWDER

Uses

Different sources of media describe the Uses of 555-16-8 differently. You can refer to the following data:
1. 4-Nitrobenzaldehyde is a benzaldehyde with a nitro group in the para position. It is used as a reagent in decarboxylative aldol reactions that are catalyzed by lipases and proteases in organic co-solvent mixtures.
2. 4-Nitrobenzaldehyde was used in the preparation of homoallylic alcohols. It was also used to develop and evaluate a series of tripeptide organocatalysts.

Definition

ChEBI: 4-nitrobenzaldehyde is a C-nitro compound that is benzaldehyde substituted at the para-position with a nitro group. It is a C-nitro compound and a member of benzaldehydes.

Synthesis Reference(s)

Journal of the American Chemical Society, 78, p. 252, 1956 DOI: 10.1021/ja01582a072Tetrahedron Letters, 28, p. 4285, 1987 DOI: 10.1016/S0040-4039(00)96486-4

Purification Methods

Purify it as for m-nitrobenzaldehyde above. [Beilstein 7 IV 589.]

Check Digit Verification of cas no

The CAS Registry Mumber 555-16-8 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,5 and 5 respectively; the second part has 2 digits, 1 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 555-16:
(5*5)+(4*5)+(3*5)+(2*1)+(1*6)=68
68 % 10 = 8
So 555-16-8 is a valid CAS Registry Number.
InChI:InChI=1/C7H5NO3/c9-5-6-1-3-7(4-2-6)8(10)11/h1-5H

555-16-8 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
  • Price
  • Detail
  • TCI America

  • (N0559)  4-Nitrobenzaldehyde  >98.0%(GC)

  • 555-16-8

  • 25g

  • 220.00CNY

  • Detail
  • TCI America

  • (N0559)  4-Nitrobenzaldehyde  >98.0%(GC)

  • 555-16-8

  • 100g

  • 590.00CNY

  • Detail
  • TCI America

  • (N0559)  4-Nitrobenzaldehyde  >98.0%(GC)

  • 555-16-8

  • 500g

  • 1,990.00CNY

  • Detail
  • Alfa Aesar

  • (A11655)  4-Nitrobenzaldehyde, 99%   

  • 555-16-8

  • 25g

  • 418.0CNY

  • Detail
  • Alfa Aesar

  • (A11655)  4-Nitrobenzaldehyde, 99%   

  • 555-16-8

  • 100g

  • 1058.0CNY

  • Detail
  • Alfa Aesar

  • (A11655)  4-Nitrobenzaldehyde, 99%   

  • 555-16-8

  • 500g

  • 4955.0CNY

  • Detail
  • Sigma-Aldrich

  • (72800)  4-Nitrobenzaldehyde  for spectrophotometric det. of amino sugars, ≥99.0%

  • 555-16-8

  • 72800-10G

  • 274.95CNY

  • Detail
  • Sigma-Aldrich

  • (72800)  4-Nitrobenzaldehyde  for spectrophotometric det. of amino sugars, ≥99.0%

  • 555-16-8

  • 72800-50G

  • 1,091.61CNY

  • Detail

555-16-8SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name 4-nitrobenzaldehyde

1.2 Other means of identification

Product number -
Other names 4-FORMYLNITROBENZENE

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:555-16-8 SDS

555-16-8Synthetic route

4-nitrobenzyl chloride
619-73-8

4-nitrobenzyl chloride

4-nitrobenzaldehdye
555-16-8

4-nitrobenzaldehdye

Conditions
ConditionsYield
With bis(2,2'-bipyridyl) copper(II) permanganate In dichloromethane for 1.5h; Ambient temperature;100%
With pyridine chromium peroxide In benzene for 0.2h; Heating;100%
With tert.-butylhydroperoxide; polystyrene-bound phenylselenic acid In tetrachloromethane for 5h; Heating;100%
4-nitrobenzylidene diacetate
2929-91-1

4-nitrobenzylidene diacetate

4-nitrobenzaldehdye
555-16-8

4-nitrobenzaldehdye

Conditions
ConditionsYield
With [NO(1+)*18-crown-6*H(NO3)2(1-)]; silica gel In dichloromethane at 20℃; for 0.0833333h;100%
With sulphated zirconia In acetonitrile at 60℃; for 0.6h; Microwave irradiation;100%
With beta zeolite modified with chlorosulphonic acid (28 wtpercent) In ethanol at 50℃; for 0.5h;100%
1-bromomethyl-4-nitro-benzene
100-11-8

1-bromomethyl-4-nitro-benzene

4-nitrobenzaldehdye
555-16-8

4-nitrobenzaldehdye

Conditions
ConditionsYield
With dipotassium hydrogenphosphate; dimethyl selenoxide In acetonitrile for 5h; Heating;100%
With 2-dimethylamino-N,N-dimethylaniline N-oxide In acetonitrile at 25℃; for 24h; Oxidation;97%
With potassium hydrogencarbonate; dimethyl sulfoxide for 0.0333333h; Microwave irradiation;97%
4-nitrophenyl-1,3-dithiane
24588-74-7

4-nitrophenyl-1,3-dithiane

4-nitrobenzaldehdye
555-16-8

4-nitrobenzaldehdye

Conditions
ConditionsYield
With silica gel; ferric nitrate In hexane at 50℃; for 0.166667h;100%
With ferric nitrate Ambient temperature;98%
With 1-benzyl-4-aza-1-azoniabicyclo[2.2.2]octane tribromide In methanol; dichloromethane at 20℃; for 0.05h;98%
4-nitrobenzyl trimethylsilyl ether
14856-73-6

4-nitrobenzyl trimethylsilyl ether

4-nitrobenzaldehdye
555-16-8

4-nitrobenzaldehdye

Conditions
ConditionsYield
With dinitrogen tetraoxide; ferric nitrate In dichloromethane at 20℃; for 1h; Oxidation;100%
With nitrogen dioxide at 20℃; for 1h;100%
With n-butyltriphenylphosphonium peroxodisulfate In acetonitrile for 0.5h; Heating;97%
4-nitrobenzaldehyde di-n-butyl acetal
19706-87-7

4-nitrobenzaldehyde di-n-butyl acetal

4-nitrobenzaldehdye
555-16-8

4-nitrobenzaldehdye

Conditions
ConditionsYield
With boron trifluoride diethyl etherate In 1,2-dichloro-ethane 0 deg C to RT;100%
aluminum oxide In gas at 350℃; Yield given;
C15H10N4O4
82820-05-1

C15H10N4O4

A

4-Phenylurazole
15988-11-1

4-Phenylurazole

B

4-nitrobenzaldehdye
555-16-8

4-nitrobenzaldehdye

Conditions
ConditionsYield
With water for 1080h;A 100%
B 100%
Sodium; 6-{[1-(4-nitro-phenyl)-meth-(E)-ylidene]-amino}-hexanoate

Sodium; 6-{[1-(4-nitro-phenyl)-meth-(E)-ylidene]-amino}-hexanoate

4-nitrobenzaldehdye
555-16-8

4-nitrobenzaldehdye

Conditions
ConditionsYield
With hydrogenchloride for 0.0416667h; Product distribution; Ambient temperature; pH = 4-6, regeneration of aldehyde;100%
N,N-Diethyl-4-nitro-selenobenzamide

N,N-Diethyl-4-nitro-selenobenzamide

4-nitrobenzaldehdye
555-16-8

4-nitrobenzaldehdye

Conditions
ConditionsYield
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 0℃; for 3h;100%
tert-butyldimethyl-4-nitrobenzyloxysilane
135605-97-9

tert-butyldimethyl-4-nitrobenzyloxysilane

4-nitrobenzaldehdye
555-16-8

4-nitrobenzaldehdye

Conditions
ConditionsYield
With dinitrogen tetraoxide; ferric nitrate at 20℃; for 0.5h; Oxidation;100%
With tetra-N-butylammonium tribromide In acetonitrile at 20℃; for 6h; Irradiation;98%
With N-hydroxyphthalimide; oxygen; cobalt(II) benzoate In acetonitrile at 20℃; for 5h;91%
4-nitrostyrene
100-13-0

4-nitrostyrene

4-nitrobenzaldehdye
555-16-8

4-nitrobenzaldehdye

Conditions
ConditionsYield
With ozone; 1-[{4-(phenylazo)-phenyl}-azo]-2-naphthalenol In water; acetonitrile at 0℃;100%
Stage #1: 4-nitrostyrene With ozone In acetone at 25℃;
Stage #2: With water In acetone at 25℃;
84%
With ruthenium trichloride; [bis(acetoxy)iodo]benzene In dichloromethane; water at 30℃; for 2.5h;83.5%
4-nitrobenzyl chloride
619-73-8

4-nitrobenzyl chloride

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-nitrobenzaldehdye
555-16-8

4-nitrobenzaldehdye

Conditions
ConditionsYield
With per-rhenic acid In toluene for 17h; Reagent/catalyst; Time; Reflux;A 96%
B 99%
4-nitrobenzyl acetate
619-90-9

4-nitrobenzyl acetate

4-nitrobenzaldehdye
555-16-8

4-nitrobenzaldehdye

Conditions
ConditionsYield
With methanol; potassium permanganate In ethyl acetate at 25℃; for 16h; Solvent;99%
4-nitrobenzaldehyde dimethyl acetal
881-67-4

4-nitrobenzaldehyde dimethyl acetal

4-nitrobenzaldehdye
555-16-8

4-nitrobenzaldehdye

Conditions
ConditionsYield
With water at 20 - 80℃; for 24h; Inert atmosphere;98.1%
With carbon tetrabromide In water; acetonitrile at 80℃; for 2h;97%
indium(III) chloride In methanol; water for 0.833333h; Heating;95%
1-methyl-4-nitrobenzene
99-99-0

1-methyl-4-nitrobenzene

4-nitrobenzaldehdye
555-16-8

4-nitrobenzaldehdye

Conditions
ConditionsYield
With oxygen; 2,2'-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) diammonium salt In tetrahydrofuran Ambient temperature; laccase from Coriolus versicolor;98%
With dihydrogen peroxide In acetonitrile at 50 - 80℃; for 24h; Reagent/catalyst;95%
With nickel-doped graphene carbon nitride nanoparticles; air In ethanol at 25℃; for 8h; Irradiation; Green chemistry;95%
4-nitrobenzyl chloride
100-14-1

4-nitrobenzyl chloride

4-nitrobenzaldehdye
555-16-8

4-nitrobenzaldehdye

Conditions
ConditionsYield
With dipotassium hydrogenphosphate; dimethyl selenoxide; tetrabutylammomium bromide In 1,2-dimethoxyethane for 4h; Heating;98%
With bismuth(III) nitrate; tetrabutyl ammonium fluoride at 100℃; for 2.7h;95%
With 1-dodecyl-3-methylimidazolium iron chloride; periodic acid at 30℃; for 2.5h;90%
2-(4-nitrophenyl)-1,3-dioxolane
2403-53-4

2-(4-nitrophenyl)-1,3-dioxolane

4-nitrobenzaldehdye
555-16-8

4-nitrobenzaldehdye

Conditions
ConditionsYield
With n-butyltriphenylphosphonium peroxodisulfate In acetonitrile for 2h; Heating;98%
With silica-OSO3H; silica gel In toluene at 60 - 70℃; for 1h;98%
With iron(III) p-toluenesulfonate hexahydrate In water for 0.666667h; Reflux;98%
tri-p-tolylphosphine sulfide
6224-65-3

tri-p-tolylphosphine sulfide

A

(E)-N-methyl-1-(4-nitrophenyl)methanimine
59862-73-6

(E)-N-methyl-1-(4-nitrophenyl)methanimine

B

tri(4-methylphenyl)phosphine oxide
797-70-6

tri(4-methylphenyl)phosphine oxide

C

4-nitrobenzaldehdye
555-16-8

4-nitrobenzaldehdye

Conditions
ConditionsYield
In chloroform-d1 at 40℃; for 72h; Rate constant; Product distribution; Mechanism; Irradiation;A 53%
B 98%
C 31%
4-nitrobenzaldehyde oxime
1129-37-9

4-nitrobenzaldehyde oxime

4-nitrobenzaldehdye
555-16-8

4-nitrobenzaldehdye

Conditions
ConditionsYield
With potassium permanganate; 1-n-butyl-3-methylimidazolim bromide at 20℃; for 0.15h; Ionic liquid; chemoselective reaction;98%
With copper(II) choride dihydrate; water In acetonitrile at 75℃; for 2.5h;98%
With bis(1-CH2Ph-3,5,7-3N-1-N(1+)tricyclo[3.3.1.13,7]decaneS2O8 In acetonitrile for 0.5h; Oxidation; Heating;97%
2-(4-nitrophenyl)-1,3-dithiolane
41159-02-8

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

4-nitrobenzaldehdye
555-16-8

4-nitrobenzaldehdye

Conditions
ConditionsYield
With silica gel; copper(II) nitrate In tetrachloromethane for 1h; Ambient temperature;98%
With ferric nitrate for 0.0111111h; Irradiation; microwave;97%
Stage #1: 2-(4-nitrophenyl)-1,3-dithiolane In ethanol at 20℃;
Stage #2: With water In ethanol at 20℃;
96%
p-nitrobenzaldehyde diethyl acetal
2403-62-5

p-nitrobenzaldehyde diethyl acetal

4-nitrobenzaldehdye
555-16-8

4-nitrobenzaldehdye

Conditions
ConditionsYield
With tungsten(VI) chloride In dichloromethane for 7h; Ambient temperature;98%
With tetrachlorosilane In dichloromethane at 20℃; for 0.666667h;88%
perchloric acid In ethanol; water at 25 - 30℃; for 1h;88%
4-nitro-benzaldehyde phenylhydrazone
2829-27-8

4-nitro-benzaldehyde phenylhydrazone

4-nitrobenzaldehdye
555-16-8

4-nitrobenzaldehdye

Conditions
ConditionsYield
With quinolinium dichromate(VI) In acetonitrile for 1.75h; Heating;98%
With potassium permanganate; silica gel In water at 20℃; for 0.416667h;98%
With water; silica gel; bis(trimethylsilyl)chromate In chloroform for 0.416667h; Heating;97%
2-(4-nitrophenyl)-1,3-oxathiolane
22391-06-6

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

4-nitrobenzaldehdye
555-16-8

4-nitrobenzaldehdye

Conditions
ConditionsYield
With bromine; dimethyl sulfoxide In chloroform at 20℃; for 0.0666667h;98%
With bromine; silica gel In dichloromethane at 20℃; for 0.166667h;98%
Stage #1: 2-(4-nitrophenyl)-1,3-oxathiolane In ethanol at 20℃; for 0.166667h;
Stage #2: With water In ethanol at 20℃; for 0.333333h;
98%
((4-nitrophenyl)methylene)bis(ethylsulfane)
7334-55-6

((4-nitrophenyl)methylene)bis(ethylsulfane)

4-nitrobenzaldehdye
555-16-8

4-nitrobenzaldehdye

Conditions
ConditionsYield
With aluminium trichloride; 1-benzyl-1-aza-4-azoniabicyclo<2.2.2>octane periodate at 20℃; for 0.333333h;98%
With dihydrogen peroxide; vanadia; ammonium bromide In dichloromethane; water at 0 - 5℃; for 2h;96%
With cetyl(trimethyl)-ammonium tribromide In dichloromethane at 0 - 5℃; for 0.5h;90%
With ammonium heptamolybdate; dihydrogen peroxide; ammonium bromide; perchloric acid In dichloromethane; water at 0 - 5℃; for 0.333333h;77%
4-nitrobenzaldehyde semicarbazone
5315-87-7

4-nitrobenzaldehyde semicarbazone

4-nitrobenzaldehdye
555-16-8

4-nitrobenzaldehdye

Conditions
ConditionsYield
With bismuth(III) nitrate; silica gel In acetone for 0.5h;98%
With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione; water; silica gel In dichloromethane at 20℃; for 2h;92%
With potassium permanganate; silica gel In water at 20℃; for 0.416667h;90%
C16H17NO4

C16H17NO4

4-nitrobenzaldehdye
555-16-8

4-nitrobenzaldehdye

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 0.75h;95%
With potassium sulfate; potassium hydrogensulfate; potassium peroxomonosulfate; aluminium trichloride In acetonitrile Heating;
4-nitrobenzaldehdye
555-16-8

4-nitrobenzaldehdye

Conditions
ConditionsYield
With 2,6-dimethylpyridine; osmium(VIII) oxide; [bis(acetoxy)iodo]benzene; water In tetrahydrofuran at 25℃; for 9h; Inert atmosphere;98%
6-N-(4'-nitrobenzylidene)aminodeoxyvasicinone
1246451-95-5

6-N-(4'-nitrobenzylidene)aminodeoxyvasicinone

A

4-nitrobenzaldehdye
555-16-8

4-nitrobenzaldehdye

B

7-amino-2,3-dihydropyrrolo[2,1-b]quinazolin-9(1H)-one
55727-53-2

7-amino-2,3-dihydropyrrolo[2,1-b]quinazolin-9(1H)-one

Conditions
ConditionsYield
In ethanol at 80℃; for 1.5h;A 92%
B 98%
C9H11NO

C9H11NO

4-nitrobenzaldehdye
555-16-8

4-nitrobenzaldehdye

Conditions
ConditionsYield
With dihydrogen peroxide In acetonitrile at 80℃; for 18h; Catalytic behavior;98%
nitromethane
75-52-5

nitromethane

4-nitrobenzaldehyde dimethyl acetal
881-67-4

4-nitrobenzaldehyde dimethyl acetal

A

1-nitro-4-[(E)-2-nitroeth-1-enyl]benzene
3156-41-0, 5576-98-7

1-nitro-4-[(E)-2-nitroeth-1-enyl]benzene

B

4-nitrobenzaldehdye
555-16-8

4-nitrobenzaldehdye

Conditions
ConditionsYield
With water at 20 - 80℃; for 24h; Henry reaction; Inert atmosphere;A 97.7%
B 2.3%
2-methyl-1H-indole
95-20-5

2-methyl-1H-indole

4-nitrobenzaldehdye
555-16-8

4-nitrobenzaldehdye

bis-(2-methyl-indol-3-yl)-(4-nitro-phenyl)-methane
6340-89-2

bis-(2-methyl-indol-3-yl)-(4-nitro-phenyl)-methane

Conditions
ConditionsYield
at 100℃; for 2h; Friedel Crafts alkylation; neat (no solvent);100%
With bismuth(III) vanadate In neat (no solvent) at 80℃; for 0.166667h; Biginelli Pyrimidone Synthesis; Green chemistry;98%
In neat (no solvent) at 20℃; for 0.0833333h; Green chemistry; chemoselective reaction;97%
acetic anhydride
108-24-7

acetic anhydride

4-nitrobenzaldehdye
555-16-8

4-nitrobenzaldehdye

4-nitrobenzylidene diacetate
2929-91-1

4-nitrobenzylidene diacetate

Conditions
ConditionsYield
With sulphated zirconia at 0℃; for 5h; regioselective reaction;100%
With poly(4-vinylpyridine)-supported sulfuric acid In dichloromethane at 20℃; for 0.166667h; Green chemistry; chemoselective reaction;100%
With SBA-15-Ph-PrSO3H at 20℃; for 1h; Reagent/catalyst; Green chemistry;100%
ethyl acetoacetate
141-97-9

ethyl acetoacetate

4-nitrobenzaldehdye
555-16-8

4-nitrobenzaldehdye

urea
57-13-6

urea

ethyl 6-methyl-4-(4-nitrophenyl)-2-oxo-1,2,3,4-tetrahydro-5-pyrimidinecarboxylate
123371-45-9

ethyl 6-methyl-4-(4-nitrophenyl)-2-oxo-1,2,3,4-tetrahydro-5-pyrimidinecarboxylate

Conditions
ConditionsYield
With 1-methylimidazole based ionic liquid terminated dendritic moiety prepared from 2,4,6-trichloro-1,3,5-triazine and 1,3-diaminopropane immobilized on 3-aminopropyltriethoxysilane functionalized bentonite In ethanol; water at 50℃; for 3h; Biginelli Pyrimidone Synthesis; Green chemistry;100%
With composite of cross-linked chitosan beads and a cyclodextrin nanosponge In water for 0.25h; Biginelli Pyrimidone Synthesis; Sonication; Green chemistry;100%
With guanidine In neat (no solvent) at 80℃; for 2h; Biginelli Pyrimidone Synthesis;99%
1-amino-naphthalene
134-32-7

1-amino-naphthalene

4-nitrobenzaldehdye
555-16-8

4-nitrobenzaldehdye

N-(napht-1-yl)-N-(p-nitrobenzylidene)amine
967-13-5

N-(napht-1-yl)-N-(p-nitrobenzylidene)amine

Conditions
ConditionsYield
for 24h; Ambient temperature;100%
In ethanol85%
With ethanol
nitromethane
75-52-5

nitromethane

4-nitrobenzaldehdye
555-16-8

4-nitrobenzaldehdye

1-(4-nitrophenyl)-2-nitroethanol
18731-47-0

1-(4-nitrophenyl)-2-nitroethanol

Conditions
ConditionsYield
With C57H78N12; copper(II) acetate monohydrate In methanol; dichloromethane for 72h; Henry reaction; Inert atmosphere;100%
With polymer supported 4-DMAP at 20℃; for 0.333333h; Reagent/catalyst; Henry Nitro Aldol Condensation;100%
With P(i-PrNCH2CH2)3N; magnesium sulfate for 0.0833333h; Ambient temperature;99%
propylene glycol
57-55-6

propylene glycol

4-nitrobenzaldehdye
555-16-8

4-nitrobenzaldehdye

4-methyl-2-(4-nitro-phenyl)-[1,3]dioxolane
65513-22-6

4-methyl-2-(4-nitro-phenyl)-[1,3]dioxolane

Conditions
ConditionsYield
With cyclohexane at 105℃; for 1h; Dean-Stark;100%
With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide In ethyl acetate at 20℃;93%
With toluene-4-sulfonic acid; benzene Unter Entfernen des entstehenden Wassers.;
malonic acid
141-82-2

malonic acid

4-nitrobenzaldehdye
555-16-8

4-nitrobenzaldehdye

4-nitro-trans-cinnamic acid
882-06-4

4-nitro-trans-cinnamic acid

Conditions
ConditionsYield
With pyridine In ethanol for 1.75h; Knoevenagel condensation; Inert atmosphere; Reflux;100%
With ammonium acetate for 0.0666667h; Irradiation;95%
Stage #1: malonic acid; 4-nitrobenzaldehdye With piperidine; pyridine Knoevenagel-Doebner reaction; Reflux;
Stage #2: With hydrogenchloride In water Cooling with ice; optical yield given as %de;
95%
1,2,4-trimethoxy-benzene
135-77-3

1,2,4-trimethoxy-benzene

4-nitrobenzaldehdye
555-16-8

4-nitrobenzaldehdye

1,1'-[(4-nitrophenyl)methanediyl]bis(2,4,5-trimethoxybenzene)
54921-89-0

1,1'-[(4-nitrophenyl)methanediyl]bis(2,4,5-trimethoxybenzene)

Conditions
ConditionsYield
With o-benzenedisulfonimide at 130℃; for 0.25h; Friedel Crafts alkylation;100%
With air; iodine In toluene at 20℃; for 72h; Friedel Crafts alkylation;99%
With niobium pentachloride In dichloromethane at 0 - 20℃; for 24h; Friedel-Crafts Alkylation;98%
N-methylhydroxyamine hydrochloride
4229-44-1

N-methylhydroxyamine hydrochloride

4-nitrobenzaldehdye
555-16-8

4-nitrobenzaldehdye

N-(p-nitrobenzylidene)methylamine N-oxide
16089-71-7, 57414-31-0, 97792-07-9

N-(p-nitrobenzylidene)methylamine N-oxide

Conditions
ConditionsYield
With 3 A molecular sieve at 20℃; for 0.25h;100%
With sodium hydroxide; silica gel at 20℃; for 0.166667h;96%
With sodium hydrogencarbonate In dichloromethane for 0.1h; microwave irradiation;95%
4-nitrobenzaldehdye
555-16-8

4-nitrobenzaldehdye

p-toluidine
106-49-0

p-toluidine

N-(4-nitrobenzylidene)-4-methylaniline
730-39-2, 33442-37-4, 149742-47-2

N-(4-nitrobenzylidene)-4-methylaniline

Conditions
ConditionsYield
for 24h; Ambient temperature;100%
100%
With montmorillonite at 20℃; for 0.0666667h; Neat (no solvent);98%
4-nitrobenzaldehdye
555-16-8

4-nitrobenzaldehdye

4-methoxy-aniline
104-94-9

4-methoxy-aniline

4-methoxy-N-(4-nitrobenzylidene)aniline
5455-87-8

4-methoxy-N-(4-nitrobenzylidene)aniline

Conditions
ConditionsYield
at 50℃; for 24h;100%
for 6h; Molecular sieve; Reflux;100%
In ethanol for 3h; Reflux;95%
4-nitrobenzaldehdye
555-16-8

4-nitrobenzaldehdye

ethylamine
75-04-7

ethylamine

N-(p-nitrobenzylidene)ethylamine
25105-58-2

N-(p-nitrobenzylidene)ethylamine

Conditions
ConditionsYield
at 20℃; under 750.06 Torr; Solid phase reaction; gas-solid reaction;100%
With water
In ethanol at 50℃;
In tetrahydrofuran; ethanol at 20℃; for 12h; Inert atmosphere;
In ethanol at 20℃; for 12h;
4-nitrobenzaldehdye
555-16-8

4-nitrobenzaldehdye

ethylene glycol
107-21-1

ethylene glycol

2-(4-nitrophenyl)-1,3-dioxolane
2403-53-4

2-(4-nitrophenyl)-1,3-dioxolane

Conditions
ConditionsYield
With toluene-4-sulfonic acid In toluene at 143℃; for 2h; Dean-Stark;100%
With cyclohexane at 105℃; for 1h; Dean-Stark;100%
With p-toluenesulfonic acid monohydrate In toluene for 4h; Reflux;100%
4-nitrobenzaldehdye
555-16-8

4-nitrobenzaldehdye

4-nitro-aniline
100-01-6

4-nitro-aniline

N-(4-nitrobenzylidene)-4-nitroaniline
10480-05-4

N-(4-nitrobenzylidene)-4-nitroaniline

Conditions
ConditionsYield
at 60℃; for 2h;100%
at 83 - 85℃;100%
With sulfuric acid In neat (no solvent) Microwave irradiation; Sealed tube; Green chemistry;72%
4-nitrobenzaldehdye
555-16-8

4-nitrobenzaldehdye

phosphonic acid diethyl ester
762-04-9

phosphonic acid diethyl ester

diethyl (hydroxy(4-nitrophenyl)methyl)phosphonate
1776-87-0

diethyl (hydroxy(4-nitrophenyl)methyl)phosphonate

Conditions
ConditionsYield
With magnesium oxide for 0.17h;100%
With {(μ-η5:η1):η1-2-[(2,6-Me2C6H3)NCH2](C4H3N)SmN(SiMe3)2}2 In toluene at 20℃; for 0.166667h; Inert atmosphere;99%
With [(μ-η5:η1):η1:η1-3-(2-C4H3NCH=NCH2CH2)C8H5N]Yb3(μ3-O)-(μ2-Cl)2(THF)2[N(SiMe3)2] In neat (no solvent) at 20℃; for 0.166667h; Inert atmosphere;99%
4-nitrobenzaldehdye
555-16-8

4-nitrobenzaldehdye

acetone
67-64-1

acetone

1-(4-nitrophenyl)-1-hydroxy-3-butanone
88958-64-9, 88958-65-0, 97600-21-0, 57548-40-0

1-(4-nitrophenyl)-1-hydroxy-3-butanone

Conditions
ConditionsYield
With Zn(2+)-(TyrOEt)2 In water at 40℃; for 24h; pH 7;100%
With sodium hydroxide at 25℃; for 0.166667h;100%
With Fe(OH)3/Fe3O4 at 50℃; for 3h;99%
4-nitrobenzaldehdye
555-16-8

4-nitrobenzaldehdye

malononitrile
109-77-3

malononitrile

4-Nitrobenzylidenemalononitrile
2700-23-4

4-Nitrobenzylidenemalononitrile

Conditions
ConditionsYield
at 150℃; for 1h; Knoevenagel condensation;100%
In various solvent(s) at 20℃; for 3h; Knoevenagel condensation;100%
hydrotalcite structure integrating fluoride ions In acetonitrile at 25℃; for 1.5h; Conversion of starting material; Knoevenagel Condensation;100%
4-nitrobenzaldehdye
555-16-8

4-nitrobenzaldehdye

benzene
71-43-2

benzene

1-(diphenylmethyl)-4-nitrobenzene
2945-12-2

1-(diphenylmethyl)-4-nitrobenzene

Conditions
ConditionsYield
With Nafion-H at 150℃; for 0.5h; Microwave irradiation;100%
With boron trifluoride monohydrate at 50℃; for 2h; Sealed tube;98%
With trifluorormethanesulfonic acid at 50℃; for 0.583333h;96%
4-nitrobenzaldehdye
555-16-8

4-nitrobenzaldehdye

4-aminobenzaldehyde
556-18-3

4-aminobenzaldehyde

Conditions
ConditionsYield
With hydrazine hydrate In ethanol; water at 80℃; for 1h; chemoselective reaction;100%
With NiRh3; hydrogen In ethyl acetate at 20℃; for 12h; Mechanism; Reagent/catalyst; Solvent; chemoselective reaction;99%
With hydrogen In ethanol; water at 25℃; under 11251.1 Torr; for 6h; chemoselective reaction;99%
4-nitrobenzaldehdye
555-16-8

4-nitrobenzaldehdye

4-nitrobenzyl chloride
619-73-8

4-nitrobenzyl chloride

Conditions
ConditionsYield
With magnesium(II) perchlorate; 1-(phenyl-2-ethyl)-7-methyl-3,5-N,N-diethylaminocarbonyl-4,7-dihydropyrrolo<2,3-b>pyridine In acetonitrile at 60℃; for 1h; Product distribution; Rate constant; reduction of other benzaldehydes and ketones and carbon carbon double bonds;100%
With magnesium(II) perchlorate; model of NADH grafted on silica matrix In acetonitrile at 65℃; for 120h; Product distribution; also with methyl benzoylformiate; varied lenght of chain, between reagent and surface of the support, reaction time, proportion of reagent/p-NBA;100%
With magnesium(II) perchlorate; polymer-bound NADH (2a) In acetonitrile; benzene at 80℃; for 120h; Further byproducts given;100%
4-nitrobenzaldehdye
555-16-8

4-nitrobenzaldehdye

4-nitrobenzaldehyde oxime
1129-37-9

4-nitrobenzaldehyde oxime

Conditions
ConditionsYield
With pyridine; hydroxylamine hydrochloride In ethanol100%
With N-hydroxyphthalimide In water at 90℃; for 3h; Sealed tube;98%
With perchloric acid; ethyl acetohydroximate In dichloromethane; water at 20℃; for 24h; Inert atmosphere;97%
4-nitrobenzaldehdye
555-16-8

4-nitrobenzaldehdye

4'-(nitrobenzyl) 4-nitrobenzoate
3481-11-6

4'-(nitrobenzyl) 4-nitrobenzoate

Conditions
ConditionsYield
With [(ImDippN)Th{N(SiMe3)2}3] In benzene-d6 at 20℃; for 24h; Reagent/catalyst; Time;100%
With Mg[iPr2NC{N-2,6-Me2-C6H3}2]2 In toluene at 25℃; for 12h; Reagent/catalyst; Tishchenko-Claisen Dismutation; Inert atmosphere;91%
With phenylmethanethiol; phenylmagnesium bromide In tetrahydrofuran; diethyl ether at 65℃; for 18h; Tishchenko reaction; Inert atmosphere;90%
4-nitrobenzaldehdye
555-16-8

4-nitrobenzaldehdye

4-nitro-benzoic acid
62-23-7

4-nitro-benzoic acid

Conditions
ConditionsYield
With sodium perborate In acetic acid for 1.5h; steam bath;100%
With phosphate-buffered silica gel supported KMnO4 In cyclohexane at 65℃;100%
With [Cu2C6H4(CHNCH2CH2N(CH2C5H4N)2)2](2+)*2ClO4(1-)=C36H38Cu2N8(ClO4)2; oxygen In acetone at -90.16℃;100%
trimethylsilyl cyanide
7677-24-9

trimethylsilyl cyanide

4-nitrobenzaldehdye
555-16-8

4-nitrobenzaldehdye

2-(4-nitrophenyl)-2-[(trimethylsilyl)oxy]acetonitrile
71189-80-5

2-(4-nitrophenyl)-2-[(trimethylsilyl)oxy]acetonitrile

Conditions
ConditionsYield
With 2Zn(2+)*10H2O*3C10H8N2*2H(1+)*Co2Mo10H4O38(6-) In neat (no solvent) at 25℃; for 7h; Reagent/catalyst; Inert atmosphere;100%
With C42H50Mg2N4 In benzene-d6 at 25℃; Glovebox; Inert atmosphere;99%
With cobalt incorporated covalent organic framework of 2,3-dihydroxyterephthalohydrazide with triformylphloroglucinol (NUS-51-Co) In dichloromethane at 24.84℃; for 10h; Catalytic behavior;99%
morpholine
110-91-8

morpholine

4-nitrobenzaldehdye
555-16-8

4-nitrobenzaldehdye

4,4'-((4-nitrophenyl)methylene)dimorpholine
6425-11-2

4,4'-((4-nitrophenyl)methylene)dimorpholine

Conditions
ConditionsYield
With copper(II) bis(trifluoromethanesulfonate) In water at 20℃; for 0.0333333h;100%
In benzene for 2h; Heating;97%
In benzene Reflux;90%
With potassium carbonate In dichloromethane at 20℃;82%
pyrrole
109-97-7

pyrrole

4-nitrobenzaldehdye
555-16-8

4-nitrobenzaldehdye

2,2'-[(4-nitrophenyl)methylene]bis(1H-pyrrole)
143859-77-2

2,2'-[(4-nitrophenyl)methylene]bis(1H-pyrrole)

Conditions
ConditionsYield
With hydrogenchloride In water at 20℃; for 2h;100%
With tetramethyl-tetra-3,4-pyridinoporphyrazinato copper(II) methyl sulfate In water at 20℃;98%
With hydrogenchloride In water at 20℃; for 2h;97%

555-16-8Relevant articles and documents

Kinetics and mechanism of oxidation of chloramphenicol - An antibiotic drug by diperiodatocuprate(III) in aqueous alkaline medium

Hosahalli, Rajeshwari V.,Byadagi, Kirthi S.,Nandibewoor, Sharanappa T.,Chimatadar, Shivamurti A.

, p. 79 - 94 (2011)

The kinetics of oxidation of chloramphenicol (CHP) by diperiodatocuprate(III) (DPC) in aqueous alkaline medium at a constant ionic strength of 0.10 mol dm-3 was studied spectrophotometrically. The reaction between DPC and CHP in alkaline medium exhibits 1:2 stoichiometry (CHP: DPC). The main oxidation products were identified by spot test, IR, NMR and GCMS spectral studies. The reaction is of first order in DPC and CHP concentrations. As the alkali concentration increases the rate of reaction increases with fractional order dependence on alkali concentration. Increase in periodate concentration decreases the rate. A suitable mechanism is proposed. The reaction constants involved in the different steps of the mechanism were calculated. The activation parameters with respect to slow step of the mechanism are computed and discussed. Thermodynamic quantities are also determined. by Oldenbourg Wissenschaftsverlag, Munchen.

Selective photocatalytic oxidation of aromatic alcohols in solar-irradiated aqueous suspensions of Pt, Au, Pd and Ag loaded TiO2 catalysts

Yurdakal, Sedat,Tek, Bilge Sina,De?irmenci, ?a?lar,Palmisano, Giovanni

, p. 53 - 59 (2017)

The photocatalytic partial oxidation of 4-methoxybenzyl alcohol (MBA) and 4-nitrobenzyl alcohol (NBA) to corresponding aldehydes or acids was performed in water under simulated solar light at different pH's by using Pt, Au, Pd and Ag loaded Degussa P25 TiO2 catalysts, prepared by photoreduction. Bare Degussa P25 TiO2 was also used as a reference. The metal loaded TiO2 photocatalysts were characterized by XRD, TEM, ESEM and DRS techniques. The best activity and selectivity results were obtained with Pt loaded TiO2. The reactivity results show that metal loading on Degussa P25 sharply promotes the photoactivity and product selectivity towards aldehydes. Moreover, at low pH's very high aldehyde selectivities were determined for both alcohols. MBA oxidation rate was very high at low pH's, whereas an opposite trend was observed for NBA, due to the difference of the substituent group. Only from NBA a significant amount 4-nitrobenzoic acid (ca. 50%) was obtained at high pH values.

Fluoro-tagged osmium and iridium nanoparticles in oxidation reactions

Santacruz, Lynay,Donnici, Silvia,Granados, Albert,Shafir, Alexandr,Vallribera, Adelina

, p. 6890 - 6895 (2018)

Osmium and iridium metal nanoparticles were supported on a fluorous organic-inorganic hybrid material prepared by the sol-gel process. Moreover, we also found that the thermolysis of the Ir4(CO)12 cluster in simply diphenylether also

Zinc chlorochromate nonahydrate [Zn(ClCrO3)2.9H2O] is a useful reagent for the solvent-free and in solution oxidative deprotection of trimethyl- and tert-butyldimethylsilyl ethers

Firouzabadi, Habib,Gholizadeh, Mostafa,Fakourpour, Mahmood

, p. 81 - 87 (1999)

Primary and secondary tert-butyldimethylsilyl and trimethylsilyl ethers are oxidized to their corresponding carbonyl compounds with zinc chlorochromate nonahydrate (ZCCNH) in dichloromethane or under solvent free conditions in good yields. For comparison, we have also studied the reactions with pyridinium chlorochromate (PCC) under similar reaction conditions.

Synthesis of novel oxime functionalized aldol products via Michael addition of oximes onto Baylis-Hillman adducts

Bhuniya, Debnath,Gujjary, Srinivas,Sengupta, Sujata

, p. 151 - 164 (2006)

Triphenylphosphine-catalyzed Michael addition of oximes 2 onto Baylis-Hillman (B-H) adducts 1 led to an easy access to a novel class of oxime functionalized aldol products 3. This demonstrates the first use of an oxygen-centered nucleophile in Michael addition to B-H adducts, without touching any other functional group. Deprotection of oxime in 3 was further demonstrated using molecular hydrogen (1 atm) and 10% Pd/C (cat.) to furnish functionalized 1,3-diols 4 as potentially useful synthons with optional backbone choice (R 3 and EWG). Copyright Taylor & Francis LLC.

-

Moffatt,J.G.

, p. 1909 - 1912 (1971)

-

Nitroamines, XVI: 4-Nitrobenzyl-n-propylnitroamine

Unterhalt,Leiblein

, p. 726 - 728 (1982)

-

Chromium(VI) based oxidants III. Ferric dichromate, polyvinylpyridine supported zinc, and ferric dichromates as new oxidizing agents

Firouzabadi,Tamami,Goudarzian,Hatam,Lakouraj

, p. 2077 - 2088 (1991)

Ferric dichromate, polyvinylpyridine supported zinc and ferric dichromates complexes are prepared and used as stable, mild, and efficient oxidizing reagents for the oxidation of different organic compounds. Ferric dichromate complex is more efficient.

Highly atom efficient synthesis of 2,2,4,5-tetrasubstituted 3(2H)-furanones having both hydroxyl and amino substituents

Antony, Jesna,Mathai, Sindhu,Natarajan, Rakesh,P. Musthafa, Sumi,Rappai, John P.,S. Devaky, Karakkattu

supporting information, (2022/02/25)

We have developed a highly atom efficient synthesis of tetrasubstituted 3(2H)-furanones from easily accessible starting materials such as C,N-diarylaldonitrones and dibenzoylacetylene. Control experiments revealed that reaction of aldonitrones having electron-withdrawing groups on the C-aryl substituent in polar aprotic solvents exhibited high product selectivity while reaction temperature has only a negligible effect on product yield and selectivity.

Microwave Assisted Oxidation of Benzyl Halides to Aldehydes and Ketones with 4-Hydroxypyridinium Nitrate Functionalized Silica Gel in Aqueous Media

Ghalehbandi, Shermineh sadat,Ghazanfari, Dadkhoda,Ahmadi, Sayed Ali,Sheikhhosseini, Enayatollah

, p. 176 - 183 (2021/04/29)

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