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6635-20-7

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6635-20-7 Usage

Uses

5-Nitrovanillin is a reagent used in the synthesis of feruloyl and caffeoyl which have antitumor properties.

Definition

ChEBI: A member of the class of benzaldehydes that is vanillin in which the hydrogen ortho- to the hydroxy group is substituted by a nitro group.

Flammability and Explosibility

Nonflammable

Purification Methods

It forms yellow plates from AcOH and needles from EtOH [Slotta & Szyszke Chem Ber 68 184 1935]. With diazomethane, 5-nitro-3,4-dimethoxyacetophenone is formed [Brady & Manjunath J Chem Soc 125 1067 1924]. The methyl ether crystallises from EtOAc or AcOH, m 88o, 90-91o, and the phenylhydrazone has m 108-110o (from aqueous EtOH). [Finger & Schott J Prakt Chem [2] 115 288 1927.] The oxime has m 216o (from EtOH or AcOH), and the oxime acetate has m 147o (from aqueous EtOH) [Vogel Monatsh Chem 20 384 1899, Brady & Dunn J Chem Soc 107 1861 1915]. [Beilstein 8 III 2064.]

Check Digit Verification of cas no

The CAS Registry Mumber 6635-20-7 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 6,6,3 and 5 respectively; the second part has 2 digits, 2 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 6635-20:
(6*6)+(5*6)+(4*3)+(3*5)+(2*2)+(1*0)=97
97 % 10 = 7
So 6635-20-7 is a valid CAS Registry Number.
InChI:InChI=1/C8H7NO5/c1-14-7-3-5(4-10)2-6(8(7)11)9(12)13/h2-4,11H,1H3

6635-20-7 Well-known Company Product Price

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  • Alfa Aesar

  • (A14296)  5-Nitrovanillin, 97%   

  • 6635-20-7

  • 5g

  • 262.0CNY

  • Detail
  • Alfa Aesar

  • (A14296)  5-Nitrovanillin, 97%   

  • 6635-20-7

  • 25g

  • 589.0CNY

  • Detail
  • Alfa Aesar

  • (A14296)  5-Nitrovanillin, 97%   

  • 6635-20-7

  • 100g

  • 1886.0CNY

  • Detail

6635-20-7SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name 5-nitrovanillin

1.2 Other means of identification

Product number -
Other names 5-Nitrovanillin

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:6635-20-7 SDS

6635-20-7Synthetic route

vanillin
121-33-5

vanillin

isonitrovanillin
6635-20-7

isonitrovanillin

Conditions
ConditionsYield
With nitric acid In acetic acid Nitration;98%
With nitric acid; acetic acid at 20℃; regioselective reaction;97%
With zirconyl nitrate In acetone at 20℃; for 3h;94%
C8H8N2O5
51673-97-3

C8H8N2O5

isonitrovanillin
6635-20-7

isonitrovanillin

Conditions
ConditionsYield
With C2H5NO2*C9H7NO*6H2O*Cl2Co; dihydrogen peroxide In methanol for 2h; Reflux;85%
vanillin
121-33-5

vanillin

A

6-nitrovanillin
2454-72-0

6-nitrovanillin

B

isonitrovanillin
6635-20-7

isonitrovanillin

C

2-nitrovanillin
2450-26-2

2-nitrovanillin

Conditions
ConditionsYield
With Nitrogen dioxide under 225.02 Torr; for 12h;A 6%
B 81%
C 10%
copper(II) bis(2-methoxy-6-nitroso-4-formylphenolato)

copper(II) bis(2-methoxy-6-nitroso-4-formylphenolato)

isonitrovanillin
6635-20-7

isonitrovanillin

Conditions
ConditionsYield
With polymer-supported thiourea In acetone at 20℃; for 24h; Molecular sieve; Inert atmosphere;21%
5-formyl-2-hydroxy-3-methoxy-benzenesulfonic acid
859932-59-5

5-formyl-2-hydroxy-3-methoxy-benzenesulfonic acid

isonitrovanillin
6635-20-7

isonitrovanillin

Conditions
ConditionsYield
With water; nitric acid
4-hydroxymethyl-2-methoxyphenol
498-00-0

4-hydroxymethyl-2-methoxyphenol

A

2-methoxy-4-nitrophenol
3251-56-7

2-methoxy-4-nitrophenol

B

isonitrovanillin
6635-20-7

isonitrovanillin

Conditions
ConditionsYield
With sulfuric acid; nitric acid; cis-nitrous acid at 25℃; Product distribution; Mechanism;A 25 % Spectr.
B 50 % Spectr.
vanillin
121-33-5

vanillin

A

2-methoxy-4-nitrophenol
3251-56-7

2-methoxy-4-nitrophenol

B

isonitrovanillin
6635-20-7

isonitrovanillin

Conditions
ConditionsYield
With sulfuric acid; nitric acid; cis-nitrous acid at 25℃; Product distribution; Mechanism;A 25 % Spectr.
B 70 % Spectr.
4-(hydroxymethyl)-2-methoxy-6-nitrophenol
37987-22-7

4-(hydroxymethyl)-2-methoxy-6-nitrophenol

isonitrovanillin
6635-20-7

isonitrovanillin

Conditions
ConditionsYield
With sodium hydroxide; potassium hexacyanoferrate(III) In 2-methoxy-ethanol
nitric acid
7697-37-2

nitric acid

vanillin
121-33-5

vanillin

acetic acid
64-19-7

acetic acid

isonitrovanillin
6635-20-7

isonitrovanillin

diethyl ether
60-29-7

diethyl ether

cis-nitrous acid
7782-77-6

cis-nitrous acid

vanillin
121-33-5

vanillin

acetone
67-64-1

acetone

isonitrovanillin
6635-20-7

isonitrovanillin

Conditions
ConditionsYield
at 0℃; zeitlicher Verlauf der Reaktion;
vanillin
121-33-5

vanillin

isonitrovanillin
6635-20-7

isonitrovanillin

Conditions
ConditionsYield
With nitric acid In acetic acid Nitration;98%
With nitric acid; acetic acid at 20℃; regioselective reaction;97%
With zirconyl nitrate In acetone at 20℃; for 3h;94%
C8H8N2O5
51673-97-3

C8H8N2O5

isonitrovanillin
6635-20-7

isonitrovanillin

Conditions
ConditionsYield
With C2H5NO2*C9H7NO*6H2O*Cl2Co; dihydrogen peroxide In methanol for 2h; Reflux;85%
vanillin
121-33-5

vanillin

A

6-nitrovanillin
2454-72-0

6-nitrovanillin

B

isonitrovanillin
6635-20-7

isonitrovanillin

C

2-nitrovanillin
2450-26-2

2-nitrovanillin

Conditions
ConditionsYield
With Nitrogen dioxide under 225.02 Torr; for 12h;A 6%
B 81%
C 10%
copper(II) bis(2-methoxy-6-nitroso-4-formylphenolato)

copper(II) bis(2-methoxy-6-nitroso-4-formylphenolato)

isonitrovanillin
6635-20-7

isonitrovanillin

Conditions
ConditionsYield
With polymer-supported thiourea In acetone at 20℃; for 24h; Molecular sieve; Inert atmosphere;21%
5-formyl-2-hydroxy-3-methoxy-benzenesulfonic acid
859932-59-5

5-formyl-2-hydroxy-3-methoxy-benzenesulfonic acid

isonitrovanillin
6635-20-7

isonitrovanillin

Conditions
ConditionsYield
With water; nitric acid
4-hydroxymethyl-2-methoxyphenol
498-00-0

4-hydroxymethyl-2-methoxyphenol

A

2-methoxy-4-nitrophenol
3251-56-7

2-methoxy-4-nitrophenol

B

isonitrovanillin
6635-20-7

isonitrovanillin

Conditions
ConditionsYield
With sulfuric acid; nitric acid; cis-nitrous acid at 25℃; Product distribution; Mechanism;A 25 % Spectr.
B 50 % Spectr.
vanillin
121-33-5

vanillin

A

2-methoxy-4-nitrophenol
3251-56-7

2-methoxy-4-nitrophenol

B

isonitrovanillin
6635-20-7

isonitrovanillin

Conditions
ConditionsYield
With sulfuric acid; nitric acid; cis-nitrous acid at 25℃; Product distribution; Mechanism;A 25 % Spectr.
B 70 % Spectr.
4-(hydroxymethyl)-2-methoxy-6-nitrophenol
37987-22-7

4-(hydroxymethyl)-2-methoxy-6-nitrophenol

isonitrovanillin
6635-20-7

isonitrovanillin

Conditions
ConditionsYield
With sodium hydroxide; potassium hexacyanoferrate(III) In 2-methoxy-ethanol
nitric acid
7697-37-2

nitric acid

vanillin
121-33-5

vanillin

acetic acid
64-19-7

acetic acid

isonitrovanillin
6635-20-7

isonitrovanillin

diethyl ether
60-29-7

diethyl ether

cis-nitrous acid
7782-77-6

cis-nitrous acid

vanillin
121-33-5

vanillin

acetone
67-64-1

acetone

isonitrovanillin
6635-20-7

isonitrovanillin

Conditions
ConditionsYield
at 0℃; zeitlicher Verlauf der Reaktion;
tetrachloromethane
56-23-5

tetrachloromethane

vanillin
121-33-5

vanillin

benzoyl nitrate

benzoyl nitrate

isonitrovanillin
6635-20-7

isonitrovanillin

diethyl ether
60-29-7

diethyl ether

vanillin
121-33-5

vanillin

concentrated , with nitros gases saturated nitric acid

concentrated , with nitros gases saturated nitric acid

isonitrovanillin
6635-20-7

isonitrovanillin

vanillin
121-33-5

vanillin

nitros gases

nitros gases

isonitrovanillin
6635-20-7

isonitrovanillin

nitric acid
7697-37-2

nitric acid

vanillin
121-33-5

vanillin

A

2-methoxy-4,6-dinitrophenol
4097-63-6

2-methoxy-4,6-dinitrophenol

B

isonitrovanillin
6635-20-7

isonitrovanillin

C

6,6'-dihydroxy-5,5'-dimethoxy-biphenyl-3,3'-dicarbaldehyde
2092-49-1

6,6'-dihydroxy-5,5'-dimethoxy-biphenyl-3,3'-dicarbaldehyde

Conditions
ConditionsYield
bei maessiger Waerme;
vanillin
121-33-5

vanillin

benzoyl nitrate

benzoyl nitrate

isonitrovanillin
6635-20-7

isonitrovanillin

Conditions
ConditionsYield
With tetrachloromethane
5-formyl-2-hydroxy-3-methoxy-benzenesulfonic acid
859932-59-5

5-formyl-2-hydroxy-3-methoxy-benzenesulfonic acid

water
7732-18-5

water

nitric acid
7697-37-2

nitric acid

isonitrovanillin
6635-20-7

isonitrovanillin

3,4-dimethoxy-benzaldehyde
120-14-9

3,4-dimethoxy-benzaldehyde

isonitrovanillin
6635-20-7

isonitrovanillin

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: nitric acid / acetic acid
2: aluminum (III) chloride; pyridine / chloroform / Reflux
View Scheme
5-nitroveratral
22027-96-9

5-nitroveratral

isonitrovanillin
6635-20-7

isonitrovanillin

Conditions
ConditionsYield
With pyridine; aluminum (III) chloride In chloroform Reflux;
isonitrovanillin
6635-20-7

isonitrovanillin

3,4-dihydroxy-5-nitrobenzaldehyde
116313-85-0

3,4-dihydroxy-5-nitrobenzaldehyde

Conditions
ConditionsYield
With hydrogen bromide; acetic acid In water at 110℃; for 39h;100%
With pyridine; aluminium trichloride In chloroform for 24h; ether cleavage; Heating;98%
With hydrogen bromide; acetic acid In water for 8h; Heating;96%
isonitrovanillin
6635-20-7

isonitrovanillin

4-(hydroxymethyl)-2-methoxy-6-nitrophenol
37987-22-7

4-(hydroxymethyl)-2-methoxy-6-nitrophenol

Conditions
ConditionsYield
With sodium tetrahydroborate In methanol at 0 - 20℃; for 1h;100%
With sodium hydroxide; sodium tetrahydroborate
isonitrovanillin
6635-20-7

isonitrovanillin

C9H6F3NO7S
1021493-52-6

C9H6F3NO7S

Conditions
ConditionsYield
With pyridine; trifluoromethylsulfonic anhydride In dichloromethane at 0 - 20℃; for 2.5h; Inert atmosphere;99%
isonitrovanillin
6635-20-7

isonitrovanillin

2-(1,3,7-trimethyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-ylthio)propanehydrazide

2-(1,3,7-trimethyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-ylthio)propanehydrazide

N'-(4-hydroxy-3-methoxy-5-nitrobenzylidene)-2-(1,3,7-trimethyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin -8-ylthio)propanehydrazide

N'-(4-hydroxy-3-methoxy-5-nitrobenzylidene)-2-(1,3,7-trimethyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin -8-ylthio)propanehydrazide

Conditions
ConditionsYield
In ethanol for 2h; Reflux;98%
isonitrovanillin
6635-20-7

isonitrovanillin

cyanoacetic acid
372-09-8

cyanoacetic acid

2-cyano-3-(3-methoxy 4-hydroxy-5-nitrophenyl)acrylic acid

2-cyano-3-(3-methoxy 4-hydroxy-5-nitrophenyl)acrylic acid

Conditions
ConditionsYield
With piperidine; acetic acid In ethanol for 3h; Reflux;96.2%
isonitrovanillin
6635-20-7

isonitrovanillin

2-hydroxy-5-chloro-aniline
95-85-2

2-hydroxy-5-chloro-aniline

C14H11ClN2O5
1372174-37-2

C14H11ClN2O5

Conditions
ConditionsYield
In ethanol for 3h; Reflux;96%
isonitrovanillin
6635-20-7

isonitrovanillin

5-nitroveratral
22027-96-9

5-nitroveratral

Conditions
ConditionsYield
In tetrahydrofuran; diethyl ether Ambient temperature;95%
In methanol; diethyl ether for 96h;
isonitrovanillin
6635-20-7

isonitrovanillin

2-cyano-N,N-diethylacetamide
26391-06-0

2-cyano-N,N-diethylacetamide

(2E)-2-cyano-3-(3-methoxy-4-hydroxy-5-nitro-phenyl)-N,Ndiethylprop-2-enamide
857629-78-8

(2E)-2-cyano-3-(3-methoxy-4-hydroxy-5-nitro-phenyl)-N,Ndiethylprop-2-enamide

Conditions
ConditionsYield
With sodium hydroxide In methanol at 20℃; for 16h;95%
With sodium hydroxide In methanol for 16h;95%
ammonium acetate In ethanol Knoevenagel Condensation; Heating / reflux;70%
trifluoromethylsulfonic anhydride
358-23-6

trifluoromethylsulfonic anhydride

isonitrovanillin
6635-20-7

isonitrovanillin

C9H6F3NO7S
1021493-52-6

C9H6F3NO7S

Conditions
ConditionsYield
In dichloromethane at 0℃;95%
isonitrovanillin
6635-20-7

isonitrovanillin

2-cyano-N,N-diethylacetamide
26391-06-0

2-cyano-N,N-diethylacetamide

2-cyano-N,N-diethyl-3-(4-hydroxy-3-methoxy-5-nitrophenyl)prop-2-enamide
146698-91-1

2-cyano-N,N-diethyl-3-(4-hydroxy-3-methoxy-5-nitrophenyl)prop-2-enamide

Conditions
ConditionsYield
acetic acid; glycine In toluene for 12 - 15h; Knoevenagel Condensation; Heating / reflux;94.2%
isonitrovanillin
6635-20-7

isonitrovanillin

[5-(1-methyl-5-nitro-1H-imidazol-2-yl)-[1,3,4]thiadiazol-2-yl]-hydrazine
823200-60-8

[5-(1-methyl-5-nitro-1H-imidazol-2-yl)-[1,3,4]thiadiazol-2-yl]-hydrazine

C14H12N8O6S

C14H12N8O6S

Conditions
ConditionsYield
With hydrogenchloride In ethanol at 20℃; for 0.5h;93%
BARBITURIC ACID
67-52-7

BARBITURIC ACID

isonitrovanillin
6635-20-7

isonitrovanillin

malononitrile
109-77-3

malononitrile

7-amino-5-(4-hydroxy-3-methoxy-5-nitrophenyl)-2,4-dioxo-1,3,4,5-tetrahydro-2H-pyrano[2,3-d]pyrimidine-6-carbonitrile

7-amino-5-(4-hydroxy-3-methoxy-5-nitrophenyl)-2,4-dioxo-1,3,4,5-tetrahydro-2H-pyrano[2,3-d]pyrimidine-6-carbonitrile

Conditions
ConditionsYield
With choline chloride; thiourea; urea In water for 0.25h; Reflux;93%
isonitrovanillin
6635-20-7

isonitrovanillin

benzyl bromide
100-39-0

benzyl bromide

4-benzyloxy-3-methoxy-5-nitrobenzaldehyde
127027-58-1

4-benzyloxy-3-methoxy-5-nitrobenzaldehyde

Conditions
ConditionsYield
With potassium hydroxide; N-benzyl-N,N,N-triethylammonium chloride In dichloromethane at 20℃; for 24h; Alkylation;92%
malonic acid
141-82-2

malonic acid

isonitrovanillin
6635-20-7

isonitrovanillin

(2E)-3-(4-hydroxy-3-methoxy-5-nitrophenyl)acrylic acid
5438-42-6, 86981-09-1

(2E)-3-(4-hydroxy-3-methoxy-5-nitrophenyl)acrylic acid

Conditions
ConditionsYield
With piperidine; pyridine for 1h; Knoevenagel-Doebner reaction; Reflux;90%
With pyridine; aniline In toluene for 2h; Reflux;84.6%
at 20 - 100℃; for 148h; Condensation; elimination;75%
With piperidine; pyridine
isonitrovanillin
6635-20-7

isonitrovanillin

(E)-3-phenylacryloylhydrazide
3538-69-0

(E)-3-phenylacryloylhydrazide

(E)-N'-(4-hydroxy-3-methoxy-5-nitrobenzylidene)cinnamohydrazide

(E)-N'-(4-hydroxy-3-methoxy-5-nitrobenzylidene)cinnamohydrazide

Conditions
ConditionsYield
With hydrogenchloride In ethanol; water for 1h; Reflux;90%
4-hydroxy-1-methyl-2(1H)-quinolone
1677-46-9

4-hydroxy-1-methyl-2(1H)-quinolone

isonitrovanillin
6635-20-7

isonitrovanillin

malononitrile
109-77-3

malononitrile

2-amino-4-(4-hydroxy-3-methoxy-5-nitrophenyl)-6-methyl-5-oxo-5,6-dihydro-4H-pyrano[3,2-c]quinoline-3-carbonitrile
1019060-09-3

2-amino-4-(4-hydroxy-3-methoxy-5-nitrophenyl)-6-methyl-5-oxo-5,6-dihydro-4H-pyrano[3,2-c]quinoline-3-carbonitrile

Conditions
ConditionsYield
With triethylamine In ethanol for 0.833333h; Heating;89%
isonitrovanillin
6635-20-7

isonitrovanillin

acetoacetic acid methyl ester
105-45-3

acetoacetic acid methyl ester

urea
57-13-6

urea

methyl 4-(4-hydroxy-3-methoxy-5-nitrophenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate

methyl 4-(4-hydroxy-3-methoxy-5-nitrophenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate

Conditions
ConditionsYield
With strontium trifluoromethanesulfonate at 70℃; for 4h; Biginelli reaction;88%
isonitrovanillin
6635-20-7

isonitrovanillin

1,2-diamino-benzene
95-54-5

1,2-diamino-benzene

2-(4-hydroxy-5-methoxy-3-nitrophenyl)benzimidazole
134610-91-6

2-(4-hydroxy-5-methoxy-3-nitrophenyl)benzimidazole

Conditions
ConditionsYield
With boric acid In water at 20 - 40℃; for 0.0833333h;88%
In methanol; nitrobenzene
isonitrovanillin
6635-20-7

isonitrovanillin

1-bromomethyl-4-nitro-benzene
100-11-8

1-bromomethyl-4-nitro-benzene

3-methoxy-5-nitro-4-[(4-nitrophenyl)methoxy]benzaldehyde
1261736-55-3

3-methoxy-5-nitro-4-[(4-nitrophenyl)methoxy]benzaldehyde

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20 - 65℃; for 14h;88%
2-naphthohydrazide
39627-84-4

2-naphthohydrazide

isonitrovanillin
6635-20-7

isonitrovanillin

N'-[(1E)-4-hydroxy-3-methoxy-5-nitrobenzylidene]-2-naphthohydrazide
1394115-39-9

N'-[(1E)-4-hydroxy-3-methoxy-5-nitrobenzylidene]-2-naphthohydrazide

Conditions
ConditionsYield
With hydrogenchloride In ethanol; water for 1h; Reflux;88%
isonitrovanillin
6635-20-7

isonitrovanillin

3-phenylpropanehydrazide
3538-68-9

3-phenylpropanehydrazide

N'-[(1E)-4-hydroxy-3-methoxy-5-nitrobenzylidene]-3-phenylpropanohydrazide
1394115-37-7

N'-[(1E)-4-hydroxy-3-methoxy-5-nitrobenzylidene]-3-phenylpropanohydrazide

Conditions
ConditionsYield
With hydrogenchloride In ethanol; water for 1h; Reflux;88%
2,3-dihydrophthalazine-1,4-dione
1445-69-8

2,3-dihydrophthalazine-1,4-dione

isonitrovanillin
6635-20-7

isonitrovanillin

dimedone
126-81-8

dimedone

3,4‑dihydro‑3,3‑dimethyl‑13‑(4‑hydroxy‑3‑methoxy‑5‑nitrophenyl)‑2H‑indazolo[2,1‑b]phthalazine‑1,6,11(13H)‑trione

3,4‑dihydro‑3,3‑dimethyl‑13‑(4‑hydroxy‑3‑methoxy‑5‑nitrophenyl)‑2H‑indazolo[2,1‑b]phthalazine‑1,6,11(13H)‑trione

Conditions
ConditionsYield
With polymer-supported sulfonic acid (PSSA) In glycerol at 80℃; for 0.916667h;88%
With [4-(1,10-phenanthrolin-1-ium-1-yl)butane-1-sulfonate]3PW12O40 In water for 0.25h; Reflux; Green chemistry;80%
4-hydroxy[1]benzopyran-2-one
1076-38-6

4-hydroxy[1]benzopyran-2-one

isonitrovanillin
6635-20-7

isonitrovanillin

3,3'-[(4-hydroxy-3-methoxy-5-nitrophenyl)methylene]-bis(4-hydroxy-2H-1-benzopyran-2-one)

3,3'-[(4-hydroxy-3-methoxy-5-nitrophenyl)methylene]-bis(4-hydroxy-2H-1-benzopyran-2-one)

Conditions
ConditionsYield
With acetic acid for 5.5h; Heating;87%
With acetic acid for 5.5h; Heating;87%
In ethanol for 24h; Reflux;70%
isonitrovanillin
6635-20-7

isonitrovanillin

(2E)-3-(3,4-dimethoxy-5-nitrophenyl)acrylohydrazide
1394115-40-2

(2E)-3-(3,4-dimethoxy-5-nitrophenyl)acrylohydrazide

(2E)-3-(3,4-dimethoxy-5-nitrophenyl)-N'-[(1E)-(4-hydroxy-3-methoxy-5-nitrobenzylidene)]acrylohydrazide
1394115-32-2

(2E)-3-(3,4-dimethoxy-5-nitrophenyl)-N'-[(1E)-(4-hydroxy-3-methoxy-5-nitrobenzylidene)]acrylohydrazide

Conditions
ConditionsYield
With hydrogenchloride In ethanol; water for 1h; Reflux;87%
isonitrovanillin
6635-20-7

isonitrovanillin

4-hydroxy-3-methoxy-5-nitrobenzonitrile
79743-73-0

4-hydroxy-3-methoxy-5-nitrobenzonitrile

Conditions
ConditionsYield
With hydroxylamine hydrochloride In dimethyl sulfoxide at 100℃; for 2h;87%
isonitrovanillin
6635-20-7

isonitrovanillin

(2E)-3-(3,4-dimethoxyphenyl)acrylohydrazide
88368-69-8

(2E)-3-(3,4-dimethoxyphenyl)acrylohydrazide

(2E)-3-(3,4-dimethoxyphenyl)-N'-[(1E)-(4-hydroxy-3-methoxy-5-nitrobenzylidene)]acrylohydrazide
1394115-34-4

(2E)-3-(3,4-dimethoxyphenyl)-N'-[(1E)-(4-hydroxy-3-methoxy-5-nitrobenzylidene)]acrylohydrazide

Conditions
ConditionsYield
With hydrogenchloride In ethanol; water for 1h; Reflux;85%
isonitrovanillin
6635-20-7

isonitrovanillin

p-aminoiodobenzene
540-37-4

p-aminoiodobenzene

C14H11IN2O4

C14H11IN2O4

Conditions
ConditionsYield
With fly-ash:PTS In neat (no solvent) Microwave irradiation; Sealed tube;85%
isonitrovanillin
6635-20-7

isonitrovanillin

dimethyl sulfate
77-78-1

dimethyl sulfate

5-nitroveratral
22027-96-9

5-nitroveratral

Conditions
ConditionsYield
With sodium hydroxide; tetrabutylammomium bromide In dichloromethane; water for 24h;84%
With sodium hydroxide; benzyl tri-n-butylammonium bromide In dichloromethane for 24h;81%
With tetrabutylammomium bromide; sodium hydroxide In dichloromethane; water at 20℃; for 24h;76%
(i) aq. KOH, (ii) /BRN= 635994/; Multistep reaction;
(i) aq. KOH, (ii) /BRN= 635994/, xylene; Multistep reaction;

6635-20-7Relevant articles and documents

Method for producing entacapone

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Paragraph 0041-0049, (2021/04/10)

The present invention relates to an entacapone production method, which comprises a nitration reaction, a de-methylation reaction and a condensation reaction. The nitration reaction is completed by glacial acetic acid, vanillin and 65% nitric acid within 3-5 hours; the de-methylation reaction is completed by reaction among nitrovanillin, dichloromethane, tetrabutyl ammonium bromide, anhydrous aluminum chloride and pyridine; and the condensation reaction is completed by reaction among isopropanol, 3,4-dihydroxyl-5-nitro benzaldehyde, N,N-diethyl cyanoacetamide and piperidine. The entacapone production method provided by the invention is high in yield, high in purity and stable in quality.

Copper-mediated nitrosation: 2-nitrosophenolato complexes and their use in the synthesis of heterocycles

Nicholls, Alexander J.,Batsanov, Andrei S.,Baxendale, Ian R.

, (2019/11/28)

A simple protocol yielding ortho-substituted nitrosophenols from phenols is demonstrated, in the form of copper(II) bis(nitrosophenolato) complexes. The developed methodology was applied to a range of substrates, confirming the role of the copper in both the formation and protection of the challenging 1, 2-substitution pattern. Using polymer supported thiourea, the Cu could be stripped from the complexes and thus enabled the isolation or identification of the uncoordinated ligands and their decomposition products, in yields generally low in line with the intrinsic high reactivity of 2-nitrosophenols. The product complexes are useful intermediates as demonstrated in revisiting a formal [4 + 2] cycloaddition with dimethylacetylene dicarboxylate to synthesise bicyclic products in variable yields, revealing the product has a novel structure different from those previously reported in the literature.

a naked-eye colorimetric receptor for anions based on nitro group featuring with benzimidazole unit

Rahmawati,Purwono,Matsjeh

, p. 1933 - 1936 (2018/08/09)

A novel receptor based on nitro group featuring with benzimidazole unit (S2) was successfully synthesized and applied to the anion (CN–, F–and H2PO4–) recognition. The S2 changed its colour for light yellow to dark yellow on addition of the anions in DMSO solvent. The LOD and Kass values determined by UV-visible titration was 2.8 × 10–6 M and 1.2 (± 0.25) × 106 M–1 for CN– ion; 1.14 × 10–6 M and 2.5 (± 0.25) × 106 M–1 for F– ion; and 1.23 × 10–5 M and 6.25 (± 0.177) × 106 M–1 for H2PO4– ion, respectively.

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