5-Nitrovanillin supplier | CasNO.6635-20-7

Name
5-Nitrovanillin
EINECS 229-633-2
CAS No. 6635-20-7
Article Data35
CAS DataBase
Density 1.456 g/cm³
Solubility 700mg/L at 23℃
Melting Point 175-178 °C
Formula C₈H₇NO₅
Boiling Point 320.9 °C at 760 mmHg
Molecular Weight 197.147
Flash Point 147.9 °C
Transport Information
Appearance yellow-green fine crystalline powder
Safety 26-36-24/25
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms Vanillin,5-nitro- (6CI,7CI,8CI);3-Methoxy-4-hydroxy-5-nitrobenzaldehyde;3-Nitro-4-hydroxy-5-methoxybenzaldehyde;4-Hydroxy-3-methoxy-5-nitrobenzaldehyde;4-Hydroxy-5-methoxy-3-nitrobenzaldehyde;5-Nitro-4-hydroxy-3-methoxybenzaldehyde;NSC 16932;NSC 35352;5-nitrovalillin;
PSA 92.35000
LogP 1.64470

Synthetic route

: 121-33-5
vanillin

: 6635-20-7
isonitrovanillin

Conditions

Conditions	Yield
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%

: 51673-97-3
C8H8N2O5

: 6635-20-7
isonitrovanillin

Conditions

Conditions	Yield
With C2H5NO2C9H7NO6H2O*Cl2Co; dihydrogen peroxide In methanol for 2h; Reflux;	85%

: 121-33-5
vanillin

A: 2454-72-0
6-nitrovanillin

B: 6635-20-7
isonitrovanillin

C: 2450-26-2
2-nitrovanillin

Conditions

Conditions	Yield
With Nitrogen dioxide under 225.02 Torr; for 12h;	A 6% B 81% C 10%

...Expand

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

: 6635-20-7
isonitrovanillin

Conditions

Conditions	Yield
With polymer-supported thiourea In acetone at 20℃; for 24h; Molecular sieve; Inert atmosphere;	21%

: 859932-59-5
5-formyl-2-hydroxy-3-methoxy-benzenesulfonic acid

: 6635-20-7
isonitrovanillin

Conditions

Conditions	Yield
With water; nitric acid

: 498-00-0
4-hydroxymethyl-2-methoxyphenol

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

B: 6635-20-7
isonitrovanillin

Conditions

Conditions	Yield
With sulfuric acid; nitric acid; cis-nitrous acid at 25℃; Product distribution; Mechanism;	A 25 % Spectr. B 50 % Spectr.

: 121-33-5
vanillin

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

B: 6635-20-7
isonitrovanillin

Conditions

Conditions	Yield
With sulfuric acid; nitric acid; cis-nitrous acid at 25℃; Product distribution; Mechanism;	A 25 % Spectr. B 70 % Spectr.

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

: 6635-20-7
isonitrovanillin

Conditions

Conditions	Yield
With sodium hydroxide; potassium hexacyanoferrate(III) In 2-methoxy-ethanol

: 7697-37-2
nitric acid

: 121-33-5
vanillin

: 64-19-7
acetic acid

: 6635-20-7
isonitrovanillin

...Expand

: 60-29-7
diethyl ether

: 7782-77-6
cis-nitrous acid

: 121-33-5
vanillin

: 67-64-1
acetone

: 6635-20-7
isonitrovanillin

Conditions

Conditions	Yield
at 0℃; zeitlicher Verlauf der Reaktion;

...Expand

: 121-33-5
vanillin

: 6635-20-7
isonitrovanillin

Conditions

Conditions	Yield
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%

: 51673-97-3
C8H8N2O5

: 6635-20-7
isonitrovanillin

Conditions

Conditions	Yield
With C2H5NO2C9H7NO6H2O*Cl2Co; dihydrogen peroxide In methanol for 2h; Reflux;	85%

: 121-33-5
vanillin

A: 2454-72-0
6-nitrovanillin

B: 6635-20-7
isonitrovanillin

C: 2450-26-2
2-nitrovanillin

Conditions

Conditions	Yield
With Nitrogen dioxide under 225.02 Torr; for 12h;	A 6% B 81% C 10%

...Expand

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

: 6635-20-7
isonitrovanillin

Conditions

Conditions	Yield
With polymer-supported thiourea In acetone at 20℃; for 24h; Molecular sieve; Inert atmosphere;	21%

: 859932-59-5
5-formyl-2-hydroxy-3-methoxy-benzenesulfonic acid

: 6635-20-7
isonitrovanillin

Conditions

Conditions	Yield
With water; nitric acid

: 498-00-0
4-hydroxymethyl-2-methoxyphenol

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

B: 6635-20-7
isonitrovanillin

Conditions

Conditions	Yield
With sulfuric acid; nitric acid; cis-nitrous acid at 25℃; Product distribution; Mechanism;	A 25 % Spectr. B 50 % Spectr.

: 121-33-5
vanillin

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

B: 6635-20-7
isonitrovanillin

Conditions

Conditions	Yield
With sulfuric acid; nitric acid; cis-nitrous acid at 25℃; Product distribution; Mechanism;	A 25 % Spectr. B 70 % Spectr.

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

: 6635-20-7
isonitrovanillin

Conditions

Conditions	Yield
With sodium hydroxide; potassium hexacyanoferrate(III) In 2-methoxy-ethanol

: 7697-37-2
nitric acid

: 121-33-5
vanillin

: 64-19-7
acetic acid

: 6635-20-7
isonitrovanillin

...Expand

: 60-29-7
diethyl ether

: 7782-77-6
cis-nitrous acid

: 121-33-5
vanillin

: 67-64-1
acetone

: 6635-20-7
isonitrovanillin

Conditions

Conditions	Yield
at 0℃; zeitlicher Verlauf der Reaktion;

...Expand

: 56-23-5
tetrachloromethane

: 121-33-5
vanillin

benzoyl nitrate: benzoyl nitrate

: 6635-20-7
isonitrovanillin

...Expand

: 60-29-7
diethyl ether

: 121-33-5
vanillin

concentrated , with nitros gases saturated nitric acid: concentrated , with nitros gases saturated nitric acid

: 6635-20-7
isonitrovanillin

...Expand

: 121-33-5
vanillin

nitros gases: nitros gases

: 6635-20-7
isonitrovanillin

: 7697-37-2
nitric acid

: 121-33-5
vanillin

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

B: 6635-20-7
isonitrovanillin

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

Conditions

Conditions	Yield
bei maessiger Waerme;

...Expand

: 121-33-5
vanillin

benzoyl nitrate: benzoyl nitrate

: 6635-20-7
isonitrovanillin

Conditions

Conditions	Yield
With tetrachloromethane

: 859932-59-5
5-formyl-2-hydroxy-3-methoxy-benzenesulfonic acid

: 7732-18-5
water

: 7697-37-2
nitric acid

: 6635-20-7
isonitrovanillin

...Expand

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

: 6635-20-7
isonitrovanillin

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: nitric acid / acetic acid 2: aluminum (III) chloride; pyridine / chloroform / Reflux View Scheme

: 22027-96-9
5-nitroveratral

: 6635-20-7
isonitrovanillin

Conditions

Conditions	Yield
With pyridine; aluminum (III) chloride In chloroform Reflux;

: 6635-20-7
isonitrovanillin

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

Conditions

Conditions	Yield
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%

: 6635-20-7
isonitrovanillin

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

Conditions

Conditions	Yield
With sodium tetrahydroborate In methanol at 0 - 20℃; for 1h;	100%
With sodium hydroxide; sodium tetrahydroborate

: 6635-20-7
isonitrovanillin

: 1021493-52-6
C9H6F3NO7S

Conditions

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

: 6635-20-7
isonitrovanillin

: 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

Conditions	Yield
In ethanol for 2h; Reflux;	98%

: 6635-20-7
isonitrovanillin

: 372-09-8
cyanoacetic acid

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

Conditions

Conditions	Yield
With piperidine; acetic acid In ethanol for 3h; Reflux;	96.2%

: 6635-20-7
isonitrovanillin

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

: 1372174-37-2
C14H11ClN2O5

Conditions

Conditions	Yield
In ethanol for 3h; Reflux;	96%

: 186581-53-3, 908094-01-9
diazomethane

: 6635-20-7
isonitrovanillin

: 22027-96-9
5-nitroveratral

Conditions

Conditions	Yield
In tetrahydrofuran; diethyl ether Ambient temperature;	95%
In methanol; diethyl ether for 96h;

: 6635-20-7
isonitrovanillin

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

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

Conditions

Conditions	Yield
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%

: 358-23-6
trifluoromethylsulfonic anhydride

: 6635-20-7
isonitrovanillin

: 1021493-52-6
C9H6F3NO7S

Conditions

Conditions	Yield
In dichloromethane at 0℃;	95%

: 6635-20-7
isonitrovanillin

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

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

Conditions

Conditions	Yield
acetic acid; glycine In toluene for 12 - 15h; Knoevenagel Condensation; Heating / reflux;	94.2%

: 6635-20-7
isonitrovanillin

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

: C14H12N8O6S

Conditions

Conditions	Yield
With hydrogenchloride In ethanol at 20℃; for 0.5h;	93%

: 67-52-7
BARBITURIC ACID

: 6635-20-7
isonitrovanillin

: 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

Conditions

Conditions	Yield
With choline chloride; thiourea; urea In water for 0.25h; Reflux;	93%

...Expand

: 6635-20-7
isonitrovanillin

: 100-39-0
benzyl bromide

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

Conditions

Conditions	Yield
With potassium hydroxide; N-benzyl-N,N,N-triethylammonium chloride In dichloromethane at 20℃; for 24h; Alkylation;	92%

: 141-82-2
malonic acid

: 6635-20-7
isonitrovanillin

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

Conditions

Conditions	Yield
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

: 6635-20-7
isonitrovanillin

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

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

Conditions

Conditions	Yield
With hydrogenchloride In ethanol; water for 1h; Reflux;	90%

: 1677-46-9
4-hydroxy-1-methyl-2(1H)-quinolone

: 6635-20-7
isonitrovanillin

: 109-77-3
malononitrile

: 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

Conditions	Yield
With triethylamine In ethanol for 0.833333h; Heating;	89%

...Expand

: 6635-20-7
isonitrovanillin

: 105-45-3
acetoacetic acid methyl ester

: 57-13-6
urea

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

Conditions

Conditions	Yield
With strontium trifluoromethanesulfonate at 70℃; for 4h; Biginelli reaction;	88%

...Expand

: 6635-20-7
isonitrovanillin

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

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

Conditions

Conditions	Yield
With boric acid In water at 20 - 40℃; for 0.0833333h;	88%
In methanol; nitrobenzene

: 6635-20-7
isonitrovanillin

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

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

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20 - 65℃; for 14h;	88%

: 39627-84-4
2-naphthohydrazide

: 6635-20-7
isonitrovanillin

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

Conditions

Conditions	Yield
With hydrogenchloride In ethanol; water for 1h; Reflux;	88%

: 6635-20-7
isonitrovanillin

: 3538-68-9
3-phenylpropanehydrazide

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

Conditions

Conditions	Yield
With hydrogenchloride In ethanol; water for 1h; Reflux;	88%

: 1445-69-8
2,3-dihydrophthalazine-1,4-dione

: 6635-20-7
isonitrovanillin

: 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

Conditions

Conditions	Yield
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%

...Expand

: 1076-38-6
4-hydroxy[1]benzopyran-2-one

: 6635-20-7
isonitrovanillin

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

Conditions

Conditions	Yield
With acetic acid for 5.5h; Heating;	87%
With acetic acid for 5.5h; Heating;	87%
In ethanol for 24h; Reflux;	70%

: 6635-20-7
isonitrovanillin

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

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

Conditions

Conditions	Yield
With hydrogenchloride In ethanol; water for 1h; Reflux;	87%

: 6635-20-7
isonitrovanillin

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

Conditions

Conditions	Yield
With hydroxylamine hydrochloride In dimethyl sulfoxide at 100℃; for 2h;	87%

: 6635-20-7
isonitrovanillin

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

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

Conditions

Conditions	Yield
With hydrogenchloride In ethanol; water for 1h; Reflux;	85%

: 6635-20-7
isonitrovanillin

: 540-37-4
p-aminoiodobenzene

: C14H11IN2O4

Conditions

Conditions	Yield
With fly-ash:PTS In neat (no solvent) Microwave irradiation; Sealed tube;	85%

: 6635-20-7
isonitrovanillin

: 77-78-1
dimethyl sulfate

: 22027-96-9
5-nitroveratral

Conditions

Conditions	Yield
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;

5-Nitrovanillin Specification

The 5-Nitrovanillin, with the CAS registry number 6635-20-7, is also known as Benzaldehyde, 4-hydroxy-3-methoxy-5-nitro-. It belongs to the product categories of Pharmaceutical Raw Materials; Aromatic Aldehydes & Derivatives (substituted); Benzaldehyde. Its EINECS registry number is 229-633-2. This chemical's molecular formula is C₈H₇NO₅ and molecular weight is 197.14488. Its IUPAC name is called 4-hydroxy-3-methoxy-5-nitrobenzaldehyde. This chemcal is yellow-green fine crystalline powder.

Physical properties of 5-Nitrovanillin: (1)ACD/LogP: 2.10; (2)ACD/LogD (pH 5.5): 1.46; (3)ACD/LogD (pH 7.4): -0.26; (4)ACD/BCF (pH 5.5): 5.29; (5)ACD/BCF (pH 7.4): 1; (6)ACD/KOC (pH 5.5): 75.37; (7)ACD/KOC (pH 7.4): 1.45; (8)#H bond acceptors: 6; (9)#H bond donors: 1; (10)#Freely Rotating Bonds: 4; (11)Index of Refraction: 1.629; (12)Molar Refractivity: 48.11 cm³; (13)Molar Volume: 135.3 cm³; (14)Surface Tension: 61.7 dyne/cm; (15)Density: 1.456 g/cm³; (16)Flash Point: 147.9 °C; (17)Enthalpy of Vaporization: 58.5 kJ/mol; (18)Boiling Point: 320.9 °C at 760 mmHg; (19)Vapour Pressure: 0.000164 mmHg at 25°C.

Uses of 5-Nitrovanillin: it can be used to produce 3,4-dihydroxy-5-nitro-benzaldehyde at temperature of 77 °C. This reaction will need reagent AlCl₃, Py and solvent ethyl acetate with reaction time of 2 hours. The yield is about 75%.

When you are using this chemical, please be cautious about it as the following:
This chemical may cause inflammation to the skin or other mucous membranes. It is irritating to eyes, respiratory system and skin. In case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice. Whenever you will contact it, please wear suitable protective clothing.

You can still convert the following datas into molecular structure:
(1)Canonical SMILES: COC1=CC(=CC(=C1O)[N+](=O)[O-])C=O
(2)InChI: InChI=1S/C8H7NO5/c1-14-7-3-5(4-10)2-6(8(7)11)9(12)13/h2-4,11H,1H3
(3)InChIKey: ZEHYRTJBFMZHCY-UHFFFAOYSA-N

Product Name

5-Nitrovanillin

Synthetic route

5-Nitrovanillin Specification

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