42454-06-8

Basic information

• Product Name: 5-Hydroxy-2-nitrobenzaldehyde
• Synonyms: LABOTEST-BB LT00233113;2-NITRO-5-HYDROXYBENZALDEHYDE;6-NITRO-3-HYDROXYBENZALDEHYDE;6-NITRO-3-HYDROXY BENZALDHYDE;5-HYDROXY-2-NITROBENZALDEHYDE;3-HYDROXY-6-NITROBENZALDEHYDE;3-Formyl-4-nitrophenol;5-hydroxy-2-nitro-benzaldehyd
• CAS NO: 42454-06-8
• Molecular Formula: C₇H₅NO₄
• Molecular Weight: 167.12
• EINECS: 255-832-9
• Product Categories: Aromatic Aldehydes & Derivatives (substituted);Benzaldehyde;Aldehydes;C7;Carbonyl Compounds;Building Blocks;Carbonyl Compounds;Chemical Synthesis;Organic Building Blocks
• Mol File: 42454-06-8.mol
• Article Data: 11

Chemical Properties

• Melting Point: 165-169 °C(lit.)
• Boiling Point: 373 °C at 760 mmHg
• Flash Point: 173.2 °C
• Appearance: /
• Density: 1.5 g/cm³
• Vapor Pressure: 4.3E-06mmHg at 25°C
• Refractive Index: 1.666
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility: Soluble in methanol.
• PKA: 6.34±0.10(Predicted)
• Sensitive: Air Sensitive
• Stability: Air Sensitive
• BRN: 1910196
• CAS DataBase Reference: 5-Hydroxy-2-nitrobenzaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Hydroxy-2-nitrobenzaldehyde(42454-06-8)
• EPA Substance Registry System: 5-Hydroxy-2-nitrobenzaldehyde(42454-06-8)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• RTECS: CU6700000
• Hazardous Substances Data: 42454-06-8(Hazardous Substances Data)

Usage

Description

5-Hydroxy-2-nitrobenzaldehyde is an organic compound that serves as a crucial raw material and intermediate in various chemical processes. It is characterized by the presence of a hydroxyl group and a nitro group attached to a benzene ring, which endows it with unique chemical properties and reactivity.

Uses

Used in Organic Synthesis:
5-Hydroxy-2-nitrobenzaldehyde is used as a key intermediate in organic synthesis for the production of various complex organic molecules. Its reactivity allows for the formation of diverse chemical bonds, making it a versatile building block in the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 5-Hydroxy-2-nitrobenzaldehyde is utilized as a starting material for the synthesis of drug candidates and active pharmaceutical ingredients. Its unique functional groups enable the development of novel drug molecules with potential therapeutic applications.
Used in Agrochemical Industry:
5-Hydroxy-2-nitrobenzaldehyde is employed as a precursor in the synthesis of agrochemicals, such as pesticides and herbicides. Its chemical properties allow for the creation of effective compounds that can protect crops and enhance agricultural productivity.
Used in Dye Industry:
In the dye industry, 5-Hydroxy-2-nitrobenzaldehyde is used as a raw material for the production of various dyes and pigments. Its ability to form colored compounds makes it a valuable component in the development of a wide range of colorants for textiles, plastics, and other applications.

Synthesis Reference(s)

The Journal of Organic Chemistry, 44, p. 409, 1979 DOI: 10.1021/jo01317a021

InChI:InChI=1/C7H5NO4/c9-4-5-3-6(10)1-2-7(5)8(11)12/h1-4,10H

Synthetic route

ethyl (3-formyl-4-nitrophenyl) carbonate (59342-81-3) → 2-nitro-5-hydroxybenzaldehyde (42454-06-8)

Conditions	Yield
With sodium hydroxide In water at 20℃; for 2h; Inert atmosphere;	95%
With sodium hydroxide In water at 20℃; for 2h;	80%
With sodium hydroxide

3-formyl-4-nitrophenyl methyl carbonate (454466-61-6) → 2-nitro-5-hydroxybenzaldehyde (42454-06-8)

Conditions	Yield
With sodium hydroxide In water	92%
With sodium hydroxide In water at 20℃; for 1h;	70%

meta-hydroxybenzaldehyde (100-83-4) → 2-nitro-5-hydroxybenzaldehyde (42454-06-8) + 3-hydroxy-2-nitrobenzaldehyde (42123-33-1)

Conditions	Yield
With perchloric acid; montmorillonite K10 supported ammonium nitrate at 60℃; for 1.66667h;	A 69% B 8%

bis(3-formylphenyl) oxalate (99306-51-1) → 2-nitro-5-hydroxybenzaldehyde (42454-06-8)

Conditions	Yield
With sulfuric acid; nitric acid In methanol; (2S)-N-methyl-1-phenylpropan-2-amine hydrate; water	66.5%
Stage #1: bis(3-formylphenyl) oxalate With sulfuric acid; nitric acid at -20 - -10℃; for 0.5h; Inert atmosphere; Stage #2: In water at -10 - 5℃; for 0.5h; Inert atmosphere; Stage #3: In methanol; water for 48h; Inert atmosphere;	63%

meta-hydroxybenzaldehyde (100-83-4) → 2-nitro-5-hydroxybenzaldehyde (42454-06-8)

Conditions	Yield
With nitric acid	25%
With nitric acid In benzene	25%
With nitric acid Inert atmosphere; regioselective reaction;	25%

carbonic acid bis-(3-formyl-4-nitro-phenyl ester) (70258-76-3) + furan-2,3,5(4H)-trione pyridine (1:1) → 2-nitro-5-hydroxybenzaldehyde (42454-06-8)

meta-hydroxybenzaldehyde (100-83-4) → 2-nitro-5-hydroxybenzaldehyde (42454-06-8) + 5-formyl-2-nitrophenol (704-13-2)

Conditions	Yield
With nitric acid
With nitric acid

nitric acid (7697-37-2) + meta-hydroxybenzaldehyde (100-83-4) → 2-nitro-5-hydroxybenzaldehyde (42454-06-8) + 4-nitro-3-oxy-benzaldehyde

nitric acid (7697-37-2) + meta-hydroxybenzaldehyde (100-83-4) → 2-nitro-5-hydroxybenzaldehyde (42454-06-8) + 4-nitro-3-oxy-benzaldehyde + 2-nitro-3-oxy-benzaldehyde

Conditions	Yield
at 35 - 60℃;

6-nitro-3-ethoxycarbonyloxy-benzaldehyde → 2-nitro-5-hydroxybenzaldehyde (42454-06-8)

Conditions	Yield
With sodium hydroxide

bis-<4-nitro-3-formyl-phenyl>-carbonate → 2-nitro-5-hydroxybenzaldehyde (42454-06-8)

Conditions	Yield
With sodium hydroxide

meta-hydroxybenzaldehyde (100-83-4) → 2-nitro-5-hydroxybenzaldehyde (42454-06-8) + 4-nitro-3-oxy-benzaldehyde

Conditions	Yield
With nitric acid
With nitric acid

ethyl (3-formyl-4-nitrophenyl) carbonate (59342-81-3) + diluted NaOH-solution → 2-nitro-5-hydroxybenzaldehyde (42454-06-8)

isopropyl alcohol (67-63-0) + 3-(3-formyl-4-nitrophenoxymethyl)-5-methoxy-1,2-dimethylindole-4,7-dione → 2-nitro-5-hydroxybenzaldehyde (42454-06-8) + 3-(hydroxymethyl)-5-methoxy-1,2-dimethyl-1H-indole-4,7-dione (161518-24-7) + 3-(isopropoxy)methyl-5-methoxy-1,2-dimethylindole-4,7-dione

Conditions	Yield
With dinitrogen monoxide In water Kinetics; γ-Irradiation;

3-formylphenyl methyl carbonate (454466-57-0) → 2-nitro-5-hydroxybenzaldehyde (42454-06-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: 95 percent / fuming HNO3; conc. H2SO4 2: 92 percent / NaOH / H2O View Scheme
Multi-step reaction with 2 steps 1: sulfuric acid; nitric acid / 0 °C 2: sodium hydroxide / water / 1 h / 20 °C View Scheme

ethyl (3-formylphenyl) carbonate (68423-35-8) → 2-nitro-5-hydroxybenzaldehyde (42454-06-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: H2SO4, HNO3 2: aq. NaOH View Scheme
Multi-step reaction with 2 steps 1: nitric acid; sulfuric acid / 4.5 h / 0 °C / Inert atmosphere 2: sodium hydroxide / water / 2 h / 20 °C / Inert atmosphere View Scheme
Multi-step reaction with 2 steps 1: sulfuric acid; nitric acid / 4 h / 0 °C 2: sodium hydroxide / water / 2 h / 20 °C View Scheme

2-nitro-5-hydroxybenzaldehyde (42454-06-8) + benzyl chloride (100-44-7) → 5-benzyloxy-2-nitrobenzaldehyde (58662-54-7)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 110℃; for 4h;	100%
Stage #1: 2-nitro-5-hydroxybenzaldehyde; benzyl chloride With potassium carbonate In DMF (N,N-dimethyl-formamide) at 20℃; Stage #2: at 60℃; for 20h;	95%
Stage #1: 2-nitro-5-hydroxybenzaldehyde; benzyl chloride With potassium carbonate In DMF (N,N-dimethyl-formamide) at 20℃; Stage #2: at 60℃; for 1 - 20h;	94%

2-nitro-5-hydroxybenzaldehyde (42454-06-8) + methyl iodide (74-88-4) → 5-methoxy-2-nitro-benzaldehyde (20357-24-8)

Conditions	Yield
With potassium carbonate In DMF (N,N-dimethyl-formamide) at 20℃; for 16h;	100%
With potassium carbonate In N,N-dimethyl-formamide at 23℃; for 10h; Inert atmosphere;	100%
With potassium carbonate In N,N-dimethyl-formamide at 20℃;	100%

3,4-dihydro-2H-pyran (110-87-2) + 2-nitro-5-hydroxybenzaldehyde (42454-06-8) → 2-nitro-5-((tetrahydro-2H-pyran-2-yl)oxy)benzaldehyde (272789-37-4)

Conditions	Yield
With pyridine; toluene-4-sulfonic acid In hexane; dichloromethane for 12h;	100%
With pyridine; toluene-4-sulfonic acid In hexane; dichloromethane for 12h;	100%
With toluene-4-sulfonic acid In diethyl ether; dichloromethane at 20℃; for 4h; Etherification;	90%
With pyridinium p-toluenesulfonate In dichloromethane at 20℃; for 12h;	84%
With pyridinium p-toluenesulfonate In dichloromethane at 20℃; for 16h; Etherification;	60%

2-nitro-5-hydroxybenzaldehyde (42454-06-8) + propargyl bromide (106-96-7) → 2-nitro-5-(prop-2-yn-1-yloxy)benzaldehyde (478964-96-4)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20℃;	100%
Stage #1: 2-nitro-5-hydroxybenzaldehyde With caesium carbonate In N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: propargyl bromide In N,N-dimethyl-formamide at 20℃; for 12h;	97%
Stage #1: 2-nitro-5-hydroxybenzaldehyde With potassium carbonate In N,N-dimethyl-formamide Stage #2: propargyl bromide In N,N-dimethyl-formamide for 16h;	86%

2-nitro-5-hydroxybenzaldehyde (42454-06-8) + allyl bromide (106-95-6) → 5-(allyloxy)-2-nitrobenzaldehyde (717105-25-4)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20℃;	100%
With N-ethyl-N,N-diisopropylamine; sodium iodide In acetone at 20℃; for 18h;
With N-ethyl-N,N-diisopropylamine at 80℃;

2-nitro-5-hydroxybenzaldehyde (42454-06-8) + pivaloyl chloride (3282-30-2) → 2,2-dimethyl-propionic acid 3-formyl-4-nitro-phenyl ester (663607-25-8)

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 0.5h;	99.5%
With N-ethyl-N,N-diisopropylamine In acetonitrile at 20 - 25℃; for 1h;	75%

2-nitro-5-hydroxybenzaldehyde (42454-06-8) + dimethyl sulfate (77-78-1) → 5-methoxy-2-nitro-benzaldehyde (20357-24-8)

Conditions	Yield
With sodium hydroxide In water at 40℃; for 5h; pH=9 - 10;	99%
With potassium hydroxide	98%
With alkaline solution at 40℃;
With alkaline solution at 60℃;

2-nitro-5-hydroxybenzaldehyde (42454-06-8) + acetyl chloride (75-36-5) → 5-acetoxy-2-nitro-benzaldehyde (76143-12-9)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 0 - 20℃;	99%
With triethylamine In acetonitrile for 1h; Ambient temperature;

2-nitro-5-hydroxybenzaldehyde (42454-06-8) + benzyl bromide (100-39-0) → 5-benzyloxy-2-nitrobenzaldehyde (58662-54-7)

Conditions	Yield
With potassium carbonate	99%
With potassium carbonate In N,N-dimethyl-formamide at 20 - 80℃; for 2h;	99%
With potassium carbonate In N,N-dimethyl-formamide at 20℃;	99%

5-bromovaleric acid methyl ester (5454-83-1) + 2-nitro-5-hydroxybenzaldehyde (42454-06-8) → 5-(3-Formyl-4-nitro-phenoxy)-pentanoic acid methyl ester (105728-03-8)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide	98%

2-nitro-5-hydroxybenzaldehyde (42454-06-8) + chloromethyl methyl ether (107-30-2) → 2-formyl-4-(methoxymethoxy)-1-nitrobenzene (170991-12-5)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; dmap In dichloromethane at 20℃;	98%
With N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃; for 1h;	93%
With N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃; for 1.5h; Inert atmosphere;	85%
With triethylamine In dichloromethane; N,N-dimethyl acetamide; toluene at 20℃;	73%
With sodium hydride In tetrahydrofuran at 20℃; for 1.33333h;

2-nitro-5-hydroxybenzaldehyde (42454-06-8) + 2-iodo-1-methoxyethane (4296-15-5) → 5-(2-methoxyethoxy)-2-nitrobenzaldehyde (927891-86-9)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 75℃; for 12h;	98%

2-nitro-5-hydroxybenzaldehyde (42454-06-8) + 1-bromo-2-(2-methoxyethoxy)ethane (54149-17-6) → 5-(2-(2-methoxyethoxy)ethoxy)-2-nitrobenzaldehyde

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 90℃; Inert atmosphere;	98%

2-nitro-5-hydroxybenzaldehyde (42454-06-8) → 3-hydroxymethyl-4-nitrophenol (60463-12-9)

Conditions	Yield
With sodium tetrahydroborate In methanol at 0 - 20℃;	97%
With sodium tetrahydroborate In methanol at 0 - 20℃; for 1h;	97%
With methanol; sodium tetrahydroborate at 0 - 20℃; for 3h; Inert atmosphere;	94%

2-Methoxyethoxymethyl chloride (3970-21-6) + 2-nitro-5-hydroxybenzaldehyde (42454-06-8) → 5-((2-methoxy)ethoxymethoxy)-2-nitrobenzaldehyde (654644-18-5)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 4h;	97%

2-nitro-5-hydroxybenzaldehyde (42454-06-8) + diethyl malonate (105-53-3) → diethyl 2-(5-hydroxy-2-nitrobenzylidene)malonate

Conditions	Yield
With iron(III) chloride; N-fluorobis(benzenesulfon)imide In neat (no solvent) at 60℃; for 24h; Knoevenagel Condensation; Inert atmosphere; Green chemistry;	97%

4-bromoethylbutanoate (2969-81-5) + 2-nitro-5-hydroxybenzaldehyde (42454-06-8) → ethyl 4-((3-formyl-4-nitrophenyl)oxy)butyrate (94193-35-8)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 1h;	95%
With potassium carbonate In N,N-dimethyl-formamide at 90 - 105℃; for 1.5h;	86%
With potassium carbonate In N,N-dimethyl-formamide for 12h; Inert atmosphere;	83%

2-nitro-5-hydroxybenzaldehyde (42454-06-8) + 1-dodecylbromide (143-15-7) → 2-nitro-5-dodecyloxybenzaldehyde

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide for 8h; Etherification; Heating;	95%
With potassium carbonate In N,N-dimethyl-formamide at 90℃; for 12h; Inert atmosphere;

2-nitro-5-hydroxybenzaldehyde (42454-06-8) + N-chloroethylpiperidine hydrochloride (2008-75-5) → 2-nitro-5-(2-piperidin-1-ylethoxy)benzaldehyde (485844-02-8)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 4h;	95%
With potassium carbonate In N,N-dimethyl-formamide at 45℃; for 16h;	85%

2-nitro-5-hydroxybenzaldehyde (42454-06-8) + 4-(2-chloroethyl)morpholine hydrochride (3647-69-6) → 5-(2-morpholinoethoxy)-2-nitrobenzaldehyde hydrochloride (904895-36-9)

Conditions	Yield
Stage #1: 2-nitro-5-hydroxybenzaldehyde; 4-(2-chloroethyl)morpholine hydrochride With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 0.666667h; Stage #2: With hydrogenchloride In methanol; ethyl acetate at 0℃;	95%

2-nitro-5-hydroxybenzaldehyde (42454-06-8) + p-toluic hydrazide (3619-22-5) → N'-(5-hydroxy-2-nitrobenzylidene)-4-methylbenzohydrazide

Conditions	Yield
In methanol at 20℃; for 1h;	95%

6-bromo-hexanoic acid ethyl ester (25542-62-5) + 2-nitro-5-hydroxybenzaldehyde (42454-06-8) → 6-(3-Formyl-4-nitro-phenoxy)-hexanoic acid ethyl ester (105728-04-9)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide	94%

ethyl 7-bromoheptanoate (29823-18-5) + 2-nitro-5-hydroxybenzaldehyde (42454-06-8) → 7-(3-Formyl-4-nitro-phenoxy)-heptanoic acid ethyl ester (105728-05-0)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide	94%

allyl iodid (556-56-9) + 2-nitro-5-hydroxybenzaldehyde (42454-06-8) → 4-hydroxy-2-(1-hydroxy-3-butenyl)-1-nitrobenzene

Conditions	Yield
With stannous fluoride In N,N-dimethyl-formamide	94%

{2-[(pyridin-2-ylmethyl)amino]ethyl}carbamic acid tert-butyl ester (294646-09-6) + 2-nitro-5-hydroxybenzaldehyde (42454-06-8) → (2-[(5-hydroxy-2-nitro-benzyl)-pyridin-2-ylmethyl-amino]-ethyl)-carbamic acid tert-butyl ester (1037826-16-6)

Conditions	Yield
With sodium tris(acetoxy)borohydride In 1,2-dichloro-ethane at 40℃; Inert atmosphere; Molecular sieve;	94%

2-nitro-5-hydroxybenzaldehyde (42454-06-8) + formamide (77287-34-4, 77287-35-5, 60100-09-6) → N-[formamido-(5-hydroxy-2-nitrophenyl)methyl]formamide (135361-38-5)

Conditions	Yield
With hydrogenchloride In 1,4-dioxane at 25℃; for 16h;	93.4%
With hydrogenchloride for 12h; Ambient temperature;	84%
With hydrogenchloride at 20 - 90℃; Inert atmosphere;	73%
With hydrogenchloride

2-nitro-5-hydroxybenzaldehyde (42454-06-8) + 2-chloroethyl tosylate (80-41-1) → 5-(2-chloroethoxy)-2-nitrobenzaldehyde (116005-59-5)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 80℃;	93%

2-nitro-5-hydroxybenzaldehyde (42454-06-8) + 4-<(3-chloropropyl)sulfonyl>piperazine-1-carboxaldehyde (149399-87-1) → 4-<<3-(3-formyl-4-nitrophenoxy)propyl>sulfonyl>-1-piperazinecarboxaldehyde

Conditions	Yield
With potassium carbonate; potassium iodide In N,N-dimethyl-formamide at 105℃; for 1.25h;	93%

1-undecen-11-ylbromide (7766-50-9) + 2-nitro-5-hydroxybenzaldehyde (42454-06-8) → C18H25NO4 (1290639-26-7)

Conditions	Yield
With potassium carbonate; potassium iodide In N,N-dimethyl-formamide at 20℃;	93%

Upstream product

• 100-83-4 meta-hydroxybenzaldehyde 
• 99306-51-1 bis(3-formylphenyl) oxalate 
• 68423-35-8 ethyl (3-formylphenyl) carbonate 
• 454466-57-0 methyl 3-formylphenyl carbonate 
• 454466-61-6 methyl 3-formyl-4-nitrophenyl carbonate 
• 67-63-0 isopropyl alcohol 
• 59342-81-3 ethyl (3-formyl-4-nitrophenyl) carbonate 
• 7697-37-2 nitric acid 
• 70258-76-3 carbonic acid bis-(3-formyl-4-nitro-phenyl ester) 

Downstream Products

• 76143-12-9 5-acetoxy-2-nitro-benzaldehyde 
• 72576-10-4 terephthalic acid bis-(3-formyl-4-nitro-phenyl ester) 
• 107558-43-0 3-formyl-4-nitrophenyl-4-methylbenzenesulfonate 
• 38711-10-3 2-Nitro-5-phenethyloxy-benzaldehyde 
• 112859-60-6 ethyl 5-(3-formyl-4-nitrophenyl)oxypentanoate 
• 151979-06-5 α-(3-formyl-4-nitrophenoxy)-p-tolunitrile 
• 485844-02-8 2-nitro-5-(2-piperidin-1-ylethoxy)benzaldehyde 
• 929268-93-9 5-{2-[(2-methoxyethyl)-methylamino]-ethoxy}-2-nitrobenzaldehyde 
• 1027818-09-2 C₁₂H₁₃NO₆ 
• 754961-03-0 3-hydroxy-2,6-dinitro-benzaldehyde 
• 60463-12-9 3-hydroxymethyl-4-nitrophenol 
• 32947-28-7 4-(5-hydroxy-2-nitrophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylic acid diethyl ester 
• 205034-11-3 Octadecanoic acid 3-formyl-4-nitro-phenyl ester 
• 205034-12-4 Icosanoic acid 3-formyl-4-nitro-phenyl ester 

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