Product Name

  • Name

    3-Nitro-4,5-dihydroxybenzaldehyde

  • EINECS 441-810-8
  • CAS No. 116313-85-0
  • Article Data27
  • CAS DataBase
  • Density 1.667 g/cm3
  • Solubility soluble in methanol
  • Melting Point 147 °C
  • Formula C7H5NO5
  • Boiling Point 310.9 °C at 760 mmHg
  • Molecular Weight 183.12
  • Flash Point 141.1 °C
  • Transport Information
  • Appearance yellow color crystalline powder.
  • Safety 26-36/37-45
  • Risk Codes 25-36-43
  • Molecular Structure Molecular Structure of 116313-85-0 (3-Nitro-4,5-dihydroxybenzaldehyde)
  • Hazard Symbols T
  • Synonyms 3,4-Dihydroxy-5-nitrobenzaldehyde;Benzaldehyde, 3,4-dihydroxy-5-nitro-;BRN 3283877;
  • PSA 103.35000
  • LogP 1.34170

Synthetic route

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%
vanillin
121-33-5

vanillin

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

3,4-dihydroxy-5-nitrobenzaldehyde

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: diethyl ether; mixture of gaseous nitrogen oxides
2: fuming hydrochloric acid / 140 °C
View Scheme
Multi-step reaction with 2 steps
1: nitric acid; acetic acid / 0 - 20 °C
2: hydrogen bromide / water / 4 h / Reflux
View Scheme
Multi-step reaction with 2 steps
1.1: acetic acid; nitric acid / water / 4 h / 15 - 30 °C
2.1: tetrabutylammomium bromide; aluminum (III) chloride / dichloromethane / 0.5 h / 0 - 10 °C / Reflux
2.2: 25 h / 0 - 10 °C / Reflux
View Scheme
isonitrovanillin
6635-20-7

isonitrovanillin

pyrographite
7440-44-0

pyrographite

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

3,4-dihydroxy-5-nitrobenzaldehyde

Conditions
ConditionsYield
With acetic acid In conc. hydrobromic acid; water5.66 kg (80%)
isovanillin
621-59-0

isovanillin

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

3,4-dihydroxy-5-nitrobenzaldehyde

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: nitric acid / acetic acid
2: aluminum (III) chloride; pyridine / chloroform / Reflux
View Scheme
3-hydroxy-4-methoxy-5-nitrobenzaldehyde
80547-69-9

3-hydroxy-4-methoxy-5-nitrobenzaldehyde

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

3,4-dihydroxy-5-nitrobenzaldehyde

Conditions
ConditionsYield
With pyridine; aluminum (III) chloride In chloroform Reflux;
N-(3-chlorophenyl)-2-cyanoacetamide
17722-12-2

N-(3-chlorophenyl)-2-cyanoacetamide

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

3,4-dihydroxy-5-nitrobenzaldehyde

C16H10ClN3O5
1150310-12-5

C16H10ClN3O5

Conditions
ConditionsYield
With piperidine; acetic acid In toluene Knoevenagel condensation; Reflux;98%
2-cyano-N-(4-methoxyphenyl)acetamide
5382-38-7

2-cyano-N-(4-methoxyphenyl)acetamide

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

3,4-dihydroxy-5-nitrobenzaldehyde

C17H13N3O6
1150310-11-4

C17H13N3O6

Conditions
ConditionsYield
With piperidine; acetic acid In toluene Knoevenagel condensation; Reflux;95%
3,4-dihydroxy-5-nitrobenzaldehyde
116313-85-0

3,4-dihydroxy-5-nitrobenzaldehyde

3,4-dihydroxy-5-nitrobenzoic acid
84211-30-3

3,4-dihydroxy-5-nitrobenzoic acid

Conditions
ConditionsYield
With sodium chlorite; sodium dihydrogenphosphate dihydrate In water; dimethyl sulfoxide at 50℃; for 16.8333h;94%
With xanthin for 20h; pH=7.4; Enzymatic reaction;
3,4-dihydroxy-5-nitrobenzaldehyde
116313-85-0

3,4-dihydroxy-5-nitrobenzaldehyde

benzyl bromide
100-39-0

benzyl bromide

3-benzyloxy-4-hydroxy-5-nitro-benzaldehyde
312327-13-2

3-benzyloxy-4-hydroxy-5-nitro-benzaldehyde

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 140℃; for 48h; Alkylation;93%
With sodium hydride In N,N-dimethyl-formamide85%
Stage #1: 3,4-dihydroxy-5-nitrobenzaldehyde With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; Inert atmosphere;
Stage #2: benzyl bromide In N,N-dimethyl-formamide; mineral oil at 0℃; for 1h; Inert atmosphere;
Stage #3: With acetic acid In N,N-dimethyl-formamide; mineral oil at 20℃; Inert atmosphere;		81%
3,4-dihydroxy-5-nitrobenzaldehyde
116313-85-0

3,4-dihydroxy-5-nitrobenzaldehyde

2-cyano-N-[3-(2-cyanoacetylamino)propyl]acetamide
111233-69-3

2-cyano-N-[3-(2-cyanoacetylamino)propyl]acetamide

(E)-2-Cyano-N-{3-[(E)-2-cyano-3-(3,4-dihydroxy-5-nitro-phenyl)-acryloylamino]-propyl}-3-(3,4-dihydroxy-5-nitro-phenyl)-acrylamide

(E)-2-Cyano-N-{3-[(E)-2-cyano-3-(3,4-dihydroxy-5-nitro-phenyl)-acryloylamino]-propyl}-3-(3,4-dihydroxy-5-nitro-phenyl)-acrylamide

Conditions
ConditionsYield
With 3-amino propanoic acid In ethanol for 4.5h; Heating;92%
2-cyano-N-m-tolylacetamide
54153-19-4

2-cyano-N-m-tolylacetamide

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

3,4-dihydroxy-5-nitrobenzaldehyde

C17H13N3O5
1150310-10-3

C17H13N3O5

Conditions
ConditionsYield
With piperidine; acetic acid In toluene Knoevenagel condensation; Reflux;89%
2-(pyrimidin-4-yl)acetonitrile
794522-90-0

2-(pyrimidin-4-yl)acetonitrile

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

3,4-dihydroxy-5-nitrobenzaldehyde

3-(3,4-dihydroxy-5-nitrophenyl)-2-(pyrimidin-4-yl)acrylonitrile

3-(3,4-dihydroxy-5-nitrophenyl)-2-(pyrimidin-4-yl)acrylonitrile

Conditions
ConditionsYield
With ammonium acetate In methanol at 80℃; for 4h;89%
3-(N,N-diphenylamino)-3-oxopropanenitrile
51838-06-3

3-(N,N-diphenylamino)-3-oxopropanenitrile

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

3,4-dihydroxy-5-nitrobenzaldehyde

C22H15N3O5
1150310-09-0

C22H15N3O5

Conditions
ConditionsYield
With piperidine; acetic acid In toluene Knoevenagel condensation; Reflux;88%
2-(pyrimidin-2-yl)acetonitrile
59566-45-9

2-(pyrimidin-2-yl)acetonitrile

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

3,4-dihydroxy-5-nitrobenzaldehyde

(E)-3-(3,4-dihydroxy-5-nitrophenyl)-2-(pyrimidin-2-yl)acrylonitrile

(E)-3-(3,4-dihydroxy-5-nitrophenyl)-2-(pyrimidin-2-yl)acrylonitrile

Conditions
ConditionsYield
With ammonium acetate In methanol for 5h; Reflux;88%
3,4-dihydroxy-5-nitrobenzaldehyde
116313-85-0

3,4-dihydroxy-5-nitrobenzaldehyde

ethylene dibromide
106-93-4

ethylene dibromide

8-nitro-2,3-dihydro-benzo[1,4]dioxine-6-carbonitrilebenzonitrile
698986-32-2

8-nitro-2,3-dihydro-benzo[1,4]dioxine-6-carbonitrilebenzonitrile

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 5h;87%
5-chlorobenzofuran-3(2H)-one
3261-05-0

5-chlorobenzofuran-3(2H)-one

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

3,4-dihydroxy-5-nitrobenzaldehyde

(2Z)-5-chloro-2-[(3,4-dihydroxy-5-nitrophenyl)methylidene]benzofuran-3-one

(2Z)-5-chloro-2-[(3,4-dihydroxy-5-nitrophenyl)methylidene]benzofuran-3-one

Conditions
ConditionsYield
With hydrogenchloride In water; isopropyl alcohol at 80℃;86%
malonic acid
141-82-2

malonic acid

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

3,4-dihydroxy-5-nitrobenzaldehyde

(E)-3-(3,4-dihydroxy-5-nitrophenyl)acrylic acid

(E)-3-(3,4-dihydroxy-5-nitrophenyl)acrylic acid

Conditions
ConditionsYield
With pyridine; aniline In toluene for 2h; Reflux;84.6%
With piperidine; pyridine at 60℃; for 48h; Knoevenagel Condensation;40%
piperidine
110-89-4

piperidine

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

2-cyano-N,N-diethylacetamide

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

3,4-dihydroxy-5-nitrobenzaldehyde

entacapone; piperidine salt
1047659-01-7

entacapone; piperidine salt

Conditions
ConditionsYield
With acetic acid In isopropyl alcohol for 3h; Product distribution / selectivity; Heating / reflux;79.7%
...Expand
4-cyanoacetylmorpholine
15029-32-0

4-cyanoacetylmorpholine

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

3,4-dihydroxy-5-nitrobenzaldehyde

C14H13N3O6
1150310-16-9

C14H13N3O6

Conditions
ConditionsYield
With piperidine; acetic acid In toluene Knoevenagel condensation; Reflux;78%
With ammonium acetate In methanol for 5h; Reflux;19%
3,4-dihydroxy-5-nitrobenzaldehyde
116313-85-0

3,4-dihydroxy-5-nitrobenzaldehyde

cyclopentanone
120-92-3

cyclopentanone

2,5-bis(3,4-dihydroxy-5-nitrobenzylidene)cyclopentanone
116313-82-7

2,5-bis(3,4-dihydroxy-5-nitrobenzylidene)cyclopentanone

Conditions
ConditionsYield
With hydrogenchloride In methanol at 5℃;77%
4.4 g (78%)
3-(3-methoxyisoxazol-5-yl)-3-oxopropanenitrile

3-(3-methoxyisoxazol-5-yl)-3-oxopropanenitrile

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

3,4-dihydroxy-5-nitrobenzaldehyde

(E)-3-(3,4-dihydroxy-5-nitrophenyl)-2-(3-methoxyisoxazole-5-carbonyl)acrylonitrile

(E)-3-(3,4-dihydroxy-5-nitrophenyl)-2-(3-methoxyisoxazole-5-carbonyl)acrylonitrile

Conditions
ConditionsYield
With ammonium acetate In methanol for 3h; Reflux;76%
2-cyano-N,N-diethylacetamide
26391-06-0

2-cyano-N,N-diethylacetamide

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

3,4-dihydroxy-5-nitrobenzaldehyde

entacapone
130929-57-6

entacapone

Conditions
ConditionsYield
Stage #1: 2-cyano-N,N-diethylacetamide; 3,4-dihydroxy-5-nitrobenzaldehyde With piperidine In 1,2-dimethoxyethane; n-heptane for 15 - 25h; Heating / reflux;
Stage #2: In dichloromethane at 25 - 35℃; for 24h; Product distribution / selectivity;		75%
With piperidine In isopropyl alcohol for 12 - 15h; Heating / reflux;75.5%
Stage #1: 2-cyano-N,N-diethylacetamide; 3,4-dihydroxy-5-nitrobenzaldehyde With acetic acid; diethylamine In toluene Knoevenagel Condensation;
Stage #2: With hydrogen bromide In acetic acid; toluene at 20℃;		73.8%
2-cyano-N,N-diethylacetamide
26391-06-0

2-cyano-N,N-diethylacetamide

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

3,4-dihydroxy-5-nitrobenzaldehyde

A

entacapone
130929-57-6

entacapone

B

(2Z)-2-cyano-3-(3,4-dihydroxy-5-nitrophenyl)-N,N-diethyl-2-propenamide
145195-63-7

(2Z)-2-cyano-3-(3,4-dihydroxy-5-nitrophenyl)-N,N-diethyl-2-propenamide

Conditions
ConditionsYield
Stage #1: 2-cyano-N,N-diethylacetamide; 3,4-dihydroxy-5-nitrobenzaldehyde With piperidine In isopropyl alcohol for 12 - 15h; Heating / reflux;
Stage #2: With acetic acid In isopropyl alcohol at 20℃;		A 75.5%
B n/a
piperidine; methylamine hydrochloride In butan-1-ol at 82℃; for 4 - 5h; Product distribution / selectivity;
piperidine; methylamine hydrochloride In i-Amyl alcohol at 89 - 90℃; for 3h; Product distribution / selectivity;
...Expand
3,4-dihydroxy-5-nitrobenzaldehyde
116313-85-0

3,4-dihydroxy-5-nitrobenzaldehyde

6-nitrobenzene-1,2,4-triol

6-nitrobenzene-1,2,4-triol

Conditions
ConditionsYield
With dihydrogen peroxide; sodium hydroxide In methanol; water at 60℃; for 3h;75%
3,4-dihydroxy-5-nitrobenzaldehyde
116313-85-0

3,4-dihydroxy-5-nitrobenzaldehyde

2-(pyridazin-3-yl)acetonitrile
27349-80-0

2-(pyridazin-3-yl)acetonitrile

(E)-3-(3,4-dihydroxy-5-nitrophenyl)-2-(pyridazin-3-yl)acrylonitrile

(E)-3-(3,4-dihydroxy-5-nitrophenyl)-2-(pyridazin-3-yl)acrylonitrile

Conditions
ConditionsYield
With ammonium acetate In methanol at 80℃; for 4h;75%
3,4-dihydroxy-5-nitrobenzaldehyde
116313-85-0

3,4-dihydroxy-5-nitrobenzaldehyde

diethyl malonate
105-53-3

diethyl malonate

diethyl 2-(3,4-dihydroxy-5-nitrobenzylidene)malonate

diethyl 2-(3,4-dihydroxy-5-nitrobenzylidene)malonate

Conditions
ConditionsYield
With piperidine; pyridine at 60℃; for 7h; Knoevenagel Condensation;69.01%
2-(1,2,4-thiadiazol-5-yl)acetonitrile

2-(1,2,4-thiadiazol-5-yl)acetonitrile

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

3,4-dihydroxy-5-nitrobenzaldehyde

(E)-3-(3,4-dihydroxy-5-nitrophenyl)-2-(1,2,4-thiadiazol-5-yl)acrylonitrile

(E)-3-(3,4-dihydroxy-5-nitrophenyl)-2-(1,2,4-thiadiazol-5-yl)acrylonitrile

Conditions
ConditionsYield
With ammonium acetate In methanol for 5h; Reflux;69%
3,4-dihydroxy-5-nitrobenzaldehyde
116313-85-0

3,4-dihydroxy-5-nitrobenzaldehyde

acetophenone
98-86-2

acetophenone

3-(3,4-dihydroxy-5-nitrophenyl)-1-phenylprop-2-en-1-one
116313-76-9

3-(3,4-dihydroxy-5-nitrophenyl)-1-phenylprop-2-en-1-one

Conditions
ConditionsYield
With hydrogenchloride In methanol68%
hydrogen ethyl malonate
1071-46-1

hydrogen ethyl malonate

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

3,4-dihydroxy-5-nitrobenzaldehyde

ethyl (E)-3-(3,4-dihydroxy-5-nitrophenyl)acrylate

ethyl (E)-3-(3,4-dihydroxy-5-nitrophenyl)acrylate

Conditions
ConditionsYield
With piperidine; pyridine at 60℃; for 24h; Knoevenagel Condensation;67.44%
neopentyl α-cyanoacetate
88107-40-8

neopentyl α-cyanoacetate

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

3,4-dihydroxy-5-nitrobenzaldehyde

Neopentyl 2-cyano-3-(3,4-dihydroxy-5-nitrophenyl)acrylate

Neopentyl 2-cyano-3-(3,4-dihydroxy-5-nitrophenyl)acrylate

Conditions
ConditionsYield
67%
1-cyanoacetylpiperidine
15029-30-8

1-cyanoacetylpiperidine

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

3,4-dihydroxy-5-nitrobenzaldehyde

(2E)-3-(3,4-dihydroxy-5-nitrophenyl)-2-(piperidin-yl-1-carbonyl)prop-2-ennitrile
1150310-15-8

(2E)-3-(3,4-dihydroxy-5-nitrophenyl)-2-(piperidin-yl-1-carbonyl)prop-2-ennitrile

Conditions
ConditionsYield
With piperidine; acetic acid In toluene Knoevenagel condensation; Reflux;67%
With ammonium acetate In methanol for 3h; Reflux;13%

3-Nitro-4,5-dihydroxybenzaldehyde Chemical Properties

Product Name: 3-Nitro-4,5-dihydroxybenzaldehyde (CAS NO.116313-85-0)

Molecular Formula: C7H5NO5
Molecular Weight: 183.12g/mol
Mol File: 116313-85-0.mol
Melting Point: 147 °C
Boiling point: 310.9 °C at 760 mmHg
Flash Point: 141.1 °C
Density: 1.667 g/cm3
Index of Refraction: 1.718 
Molar Refractivity: 43.31 cm3 
Molar Volume: 109.8 cm3 
Surface Tension: 89.6 dyne/cm
Enthalpy of Vaporization: 57.38 kJ/mol
Vapour Pressure: 0.000319 mmHg at 25°C
XLogP3-AA: 1.1
H-Bond Donor: 2
H-Bond Acceptor: 5
Structure Descriptors of 3-Nitro-4,5-dihydroxybenzaldehyde (CAS NO.116313-85-0):
  IUPAC Name: 3,4-dihydroxy-5-nitrobenzaldehyde
  Canonical SMILES: C1=C(C=C(C(=C1[N+](=O)[O-])O)O)C=O
  InChI: InChI=1S/C7H5NO5/c9-3-4-1-5(8(12)13)7(11)6(10)2-4/h1-3,10-11H 
  InChIKey: BBFJODMCHICIAA-UHFFFAOYSA-N
Product Categories: Aromatic Aldehydes & Derivatives (substituted); Benzaldehyde; pharmaceutical intermediates

3-Nitro-4,5-dihydroxybenzaldehyde Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LDLo oral 312mg/kg (312mg/kg)   Helvetica Chimica Acta. Vol. 72, Pg. 952, 1989.

3-Nitro-4,5-dihydroxybenzaldehyde Safety Profile

Combustion Products: These products include toxic carbon oxides (CO,CO 2), nitrogen oxides (NOx).
SMALL FIRE: Use DRY chemical powder.
LARGE FIRE: Use water spray, fog or foam. DO NOT use water jet.
RTECS:  CU5665000

3-Nitro-4,5-dihydroxybenzaldehyde Specification

 3-Nitro-4,5-dihydroxybenzaldehyde , its CAS NO. is 116313-85-0, the synonyms are 3,4-Dihydroxy-5-nitrobenzaldehyde ;  Benzaldehyde, 3,4-dihydroxy-5-nitro- .

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