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5-Nitrovanillin

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Name

5-Nitrovanillin

EINECS 229-633-2
CAS No. 6635-20-7 Density 1.456 g/cm3
PSA 92.35000 LogP 1.64470
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 N/A Appearance yellow-green fine crystalline powder
Safety 26-36-24/25 Risk Codes 36/37/38
Molecular Structure Molecular Structure of 6635-20-7 (5-Nitrovanillin) Hazard Symbols IrritantXi
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;

Article Data 35

5-Nitrovanillin Synthetic route

121-33-5

vanillin

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%
51673-97-3

C8H8N2O5

6635-20-7

isonitrovanillin

Conditions
ConditionsYield
With C2H5NO2*C9H7NO*6H2O*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
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)

6635-20-7

isonitrovanillin

Conditions
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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

60-29-7

diethyl ether

7782-77-6

cis-nitrous acid

121-33-5

vanillin

67-64-1

acetone

6635-20-7

isonitrovanillin

Conditions
ConditionsYield
at 0℃; zeitlicher Verlauf der Reaktion;

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

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