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

Chemical Properties

Yellow powder

Uses

5-Hydroxy-2-nitrobenzaldehyde is an important raw material and intermediate used in organic synthesis, pharmaceuticals, agrochemicals and dyestuff.

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

• 70258-76-3 carbonic acid bis-(3-formyl-4-nitro-phenyl ester) 
• 100-83-4 meta-hydroxybenzaldehyde 
• 59342-81-3 ethyl (3-formyl-4-nitrophenyl) carbonate 
• 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 
• 7697-37-2 nitric acid 

Downstream Products

• 70258-76-3 carbonic acid bis-(3-formyl-4-nitro-phenyl ester) 
• 103569-28-4 naphthalene-2,6-disulfonic acid bis-(3-formyl-4-nitro-phenyl ester) 
• 20357-24-8 5-methoxy-2-nitro-benzaldehyde 
• 7310-94-3 2-chloro-5-hydroxybenzaldehyde 
• 2973-80-0 2-bromo-5-hydroxybenzaldehyde 
• 610-37-7 5-hydroxy-2-nitrobenzoic acid 
• 60463-12-9 3-hydroxymethyl-4-nitrophenol 
• 67175-38-6 2,4-dibromo-3-hydroxy-6-nitrobenzaldehyde 
• 683228-77-5 3-hydroxy-2,4-diiodo-6-nitro-benzaldehyde 
• 76143-12-9 5-acetoxy-2-nitro-benzaldehyde 
• 109134-05-6 5-ethoxy-2-nitrobenzaldehyde 
• 135361-38-5 N-[formamido-(5-hydroxy-2-nitrophenyl)methyl]formamide 
• 142103-84-2 5-(2,2-Dimethyl-[1,3]dioxolan-4-ylmethoxy)-2-nitro-benzaldehyde 
• 225786-60-7 5-(hexyloxy)-2-nitrobenzaldehyde 

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