56962-11-9

Basic information

• Product Name: 2-Chloro-4-hydroxybenzaldehyde
• Synonyms: Benzaldehyde, 2-chloro-4-hydroxy-;TIMTEC-BB SBB004014;2-CHLORO-4-HYDROXYBENZALDEHYDE;2-CHLORO-4-HYDROXYBENZALDEHYDE 99% &
• CAS NO: 56962-11-9
• Molecular Formula: C₇H₅ClO₂
• Molecular Weight: 156.57
• Product Categories: Aromatic Aldehydes & Derivatives (substituted);Aromatic Phenylacetic Acids and Derivatives;Benzaldehyde;Aldehydes;C7;Carbonyl Compounds;Building Blocks;Carbonyl Compounds;Chemical Synthesis;Organic Building Blocks
• Mol File: 56962-11-9.mol
• Article Data: 8

Chemical Properties

• Melting Point: 145-147 °C(lit.)
• Boiling Point: 272.492 °C at 760 mmHg
• Flash Point: 118.599 °C
• Appearance: /
• Density: 1.404 g/cm³
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility: Soluble in organic solvents.
• PKA: 6.81±0.18(Predicted)
• Sensitive: Air Sensitive
• CAS DataBase Reference: 2-Chloro-4-hydroxybenzaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Chloro-4-hydroxybenzaldehyde(56962-11-9)
• EPA Substance Registry System: 2-Chloro-4-hydroxybenzaldehyde(56962-11-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 3
• Hazardous Substances Data: 56962-11-9(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 56962-11-9 differently. You can refer to the following data:
1. 2-Chloro-4-hydroxybenzaldehyde, is used as an important raw material and intermediate used in organic Synthesis, pharmaceuticals, agrochemicals and dyestuff.
2. 2-Chloro-4-hydroxybenzaldehyde may be used in chemical synthesis.

General Description

N-Thioamide thiosemicarbazone derivatives of 2-chloro-4-hydroxy-benzaldehyde have been prepared. pK values for acid dissociation of 2-chloro-4-hydroxybenzaldehyde has been evaluated.

Synthetic route

2-chloro-4-hydroxybenzonitrile (3336-16-1) → 2-chloro-4-hydroxybenzaldehyde (56962-11-9)

Conditions	Yield
Stage #1: 2-chloro-4-hydroxybenzonitrile With diisobutylaluminium hydride In tetrahydrofuran; hexane at -78 - 20℃; for 19h; Stage #2: With hydrogenchloride In tetrahydrofuran; hexane; water at 0℃;	84%
With diisobutylaluminium hydride In tetrahydrofuran; hexane at -78 - 20℃; for 3h;
Stage #1: 2-chloro-4-hydroxybenzonitrile With diisobutylaluminium hydride In hexane; chloroform at -50℃; for 1.5h; Stage #2: With hydrogenchloride In methanol; water

3-monochlorophenol (108-43-0) + chloroform (67-66-3) → 2-chloro-4-hydroxybenzaldehyde (56962-11-9)

Conditions	Yield
Stage #1: 3-monochlorophenol; chloroform With calcium hydroxide; water; sodium carbonate for 4.33333h; Heating / reflux; Stage #2: With hydrogenchloride In chloroform; water	16%
With water; sodium carbonate; calcium hydroxide for 4.33333h; Inert atmosphere; Reflux;	15.3%
With sodium carbonate; calcium hydroxide In water for 3h; Reflux; Inert atmosphere;	15.3%

3-monochlorophenol (108-43-0) + hydrogen cyanide (74-90-8) → 2-chloro-4-hydroxybenzaldehyde (56962-11-9)

Conditions	Yield
With hydrogenchloride; aluminium trichloride; benzene at 30℃; Durch Erhitzen des Reaktionsproduktes mit verd. Salzsaeure;

2-chloro-4-nitrotoluene (121-86-8) → 2-chloro-4-hydroxybenzaldehyde (56962-11-9)

Conditions	Yield
With sodium hydroxide; sulfur Diazotieren des Reaktionsproduktes und nachfolgendes Kochen mit 40prozentiger Schwefelsaeure;

2,4-dichlorobenzaldeyhde (874-42-0) → 2-chloro-4-hydroxybenzaldehyde (56962-11-9)

Conditions	Yield
With potassium carbonate at 220℃; unter Druck;

3-monochlorophenol (108-43-0) + trichloroacetic acid (76-03-9) → 4-chlorosalicylaldehyde (2420-26-0) + 2-chloro-4-hydroxybenzaldehyde (56962-11-9)

Conditions	Yield
With potassium hydroxide; water

3-monochlorophenol (108-43-0) + chloroform (67-66-3) → 2-chloro-4-hydroxybenzaldehyde (56962-11-9) + 4-chloro-2-oxy-benzaldehyde

Conditions	Yield
With sodium hydroxide Mengenverhaeltnis zwischen den Produkten;
With extinguished lime; sodium carbonate; calcium carbonate

3-monochlorophenol (108-43-0) + Bromoform (75-25-2) → 2-chloro-4-hydroxybenzaldehyde (56962-11-9) + 4-chloro-2-oxy-benzaldehyde

Conditions	Yield
With sodium hydroxide Mengenverhaeltnis zwischen den Produkten;

3-monochlorophenol (108-43-0) + trichloroacetic acid (76-03-9) + aqueous KOH → 4-chlorosalicylaldehyde (2420-26-0) + 2-chloro-4-hydroxybenzaldehyde (56962-11-9)

2-chloro-4-hydroxybenzaldehyde (56962-11-9) + Glyoxal (131543-46-9) → 3-chloro-4-(1H-imidazol-2-yl)phenol

Conditions	Yield
With ammonium hydroxide In methanol; water at 0 - 20℃; for 28h; Inert atmosphere;	100%

2-chloro-4-hydroxybenzaldehyde (56962-11-9) + 2-amino-4,6-dimethoxybenzamide (63920-73-0) → 2-(2-chloro-4-hydroxyphenyl)-5,7-dimethoxyquinazolin-4(3H)-one

Conditions	Yield
With iodine In ethanol for 4h; Inert atmosphere; Reflux;	100%

2-chloro-4-hydroxybenzaldehyde (56962-11-9) + tert-butyldimethylsilyl chloride (18162-48-6) → 4-{[tert-butyl(dimethyl)silyl]oxy}-2-chlorobenzaldehyde (550377-89-4)

Conditions	Yield
With 1H-imidazole In N,N-dimethyl-formamide	99%
With 1H-imidazole; dmap In DMF (N,N-dimethyl-formamide) at 20℃; for 16h;	75%
With 1H-imidazole; dmap In N,N-dimethyl-formamide at 20℃; for 65h;	39%

1-bromo-4-butene (5162-44-7) + 2-chloro-4-hydroxybenzaldehyde (56962-11-9) → 4-(but-3-enyloxy)-2-chlorobenzaldehyde (1196879-38-5)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 12h; Inert atmosphere;	98%

2-chloro-4-hydroxybenzaldehyde (56962-11-9) → 4-acetoxy-2-chlorobenzaldehyde (114416-77-2)

Conditions	Yield
With pyridine; acetic anhydride In dichloromethane	96%

2,4-thiazolidinedion (2295-31-0) + 2-chloro-4-hydroxybenzaldehyde (56962-11-9) → (5-(2-chloro-4-hydroxybenzylidene)thiazolidine-2,4-dione)

Conditions	Yield
With piperidine; acetic acid In toluene at 80℃; Dean-Stark;	95%

2-chloro-4-hydroxybenzaldehyde (56962-11-9) + C13H14BrNO (1374961-75-7) → 2-chloro-4-[(5-isopropyl-3-phenylisoxazol-4-yl)methoxy]benzaldehyde (1374961-77-9)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 3h;	94%

4-(hydroxymethyl)-5-cyclopropyl-3-(2,6-dichlorophenyl)isoxazole (946426-89-7) + 2-chloro-4-hydroxybenzaldehyde (56962-11-9) → 2-chloro-4-[[5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazol-4-yl]methoxy]benzaldehyde (1268246-55-4)

Conditions	Yield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 20℃; for 2h; Inert atmosphere;	94%

2-chloro-4-hydroxybenzaldehyde (56962-11-9) + ethyl iodide (75-03-6) → 4-ethoxy-2-chloro-benzaldehyde

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 2.5h;	93%

2-chloro-4-hydroxybenzaldehyde (56962-11-9) + 6-(Butylamino)-3-methyluracil (5759-64-8) → 10-Butyl-8-hydroxy-3-methyl-10H-pyrimido[4,5-b]quinoline-2,4-dione (84459-40-5)

Conditions	Yield
In N,N-dimethyl-formamide for 5h; Heating;	92%

2-chloro-4-hydroxybenzaldehyde (56962-11-9) + 4-(chloromethyl)-5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazole (1268245-50-6) → 2-chloro-4-[[5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazol-4-yl]methoxy]benzaldehyde (1268246-55-4)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 60℃;	90%

2-chloro-4-hydroxybenzaldehyde (56962-11-9) + 1-bromo-hexane (111-25-1) → 2-chloro-4-n-hexyloxybenzaldehyde

Conditions	Yield
With tetra-(n-butyl)ammonium iodide; potassium carbonate In butanone for 5h; Reflux;	89%

6-methoxy-3-coumaranone (15832-09-4) + 2-chloro-4-hydroxybenzaldehyde (56962-11-9) → C16H11ClO4

Conditions	Yield
With hydrogenchloride In water; acetic acid at 20℃; for 2h;	88.9%

2-chloro-4-hydroxybenzaldehyde (56962-11-9) + benzyl bromide (100-39-0) → 4-(benzyloxy)-2-chlorobenzaldehyde (117490-57-0)

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 20℃; for 72h; Product distribution / selectivity;	87%
With caesium carbonate In N,N-dimethyl-formamide at 20℃; for 72h; Product distribution / selectivity;	87%
With potassium carbonate In acetone for 2h; Heating;	80%
With caesium carbonate In acetonitrile at 20℃; for 2h;	59%

2-chloro-4-hydroxybenzaldehyde (56962-11-9) + cyclohexylethan-1-ol (4442-79-9) → 2-chloro-4-(2-cyclohexylethoxy)benzaldehyde (1234323-04-6)

Conditions	Yield
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran; toluene at 0 - 20℃; Mitsunobu Displacement;	87%

2-chloro-4-hydroxybenzaldehyde (56962-11-9) + 1-chloro-3-hydroxypropane (627-30-5) → 2-chloro-4-(3-hydroxypropoxy)benzaldehyde

Conditions	Yield
With potassium carbonate; potassium iodide In N,N-dimethyl-formamide at 5 - 70℃; for 16h; Inert atmosphere;	86.6%

2-chloro-4-hydroxybenzaldehyde (56962-11-9) + acetyl chloride (75-36-5) → 4-acetoxy-2-chlorobenzaldehyde (114416-77-2)

Conditions	Yield
With triethylamine In tetrahydrofuran at 0 - 20℃; for 1h;	86%

2-chloro-4-hydroxybenzaldehyde (56962-11-9) + 2-oxa-6-azaspiro[3.3]heptane 0.5 oxalic acid salt → 3-chloro-4-(2-oxa-6-azaspiro[3.3]heptan-6-ylmethyl)phenol (1254035-91-0)

Conditions	Yield
With sodium tris(acetoxy)borohydride In dichloromethane	85%

2-chloro-4-hydroxybenzaldehyde (56962-11-9) + 2-oxa-6-azaspiro[3.3]heptane (174-78-7) → 3-chloro-4-(2-oxa-6-azaspiro[3.3]heptan-6-ylmethyl)phenol (1254035-91-0)

Conditions	Yield
Stage #1: 2-chloro-4-hydroxybenzaldehyde; 2-oxa-6-azaspiro[3.3]heptane In dichloromethane for 0.333333h; Stage #2: With sodium tris(acetoxy)borohydride In dichloromethane at 20℃;	85%

2-chloro-4-hydroxybenzaldehyde (56962-11-9) + 6-methylamino-3-methyluracil (5759-63-7) → 3,10-Dimethyl-8-hydroxy-2,4(3H,10H)-pyrimido<4,5-b>chinolindion (75427-52-0)

Conditions	Yield
In N,N-dimethyl-formamide for 5h; Heating;	83%

2-chloro-4-hydroxybenzaldehyde (56962-11-9) + 4-bromoethylbutanoate (2969-81-5) → ethyl 4-[3-chloro-4-formylphenoxy]butanoate

Conditions	Yield
Stage #1: 2-chloro-4-hydroxybenzaldehyde With potassium carbonate; potassium iodide In 1-methyl-pyrrolidin-2-one at 20℃; for 0.5h; Inert atmosphere; Stage #2: Ethyl 4-bromobutyrate In 1-methyl-pyrrolidin-2-one at 60℃; for 7h; Inert atmosphere;	82%

2-chloro-4-hydroxybenzaldehyde (56962-11-9) → 5-bromo-2-chloro-4-hydroxybenzaldehyde (957774-27-5)

Conditions	Yield
With pyridinium hydrobromide perbromide In methanol at 0℃; for 4h; Inert atmosphere;	81.27%
With pyridinium hydrobromide perbromide In methanol at 0℃; for 5h;	73%
With pyridinium tribromide In methanol at 0℃; for 4h;
With Pyridine hydrobromide In dichloromethane at 0℃; for 5h;

2-chloro-4-hydroxybenzaldehyde (56962-11-9) + 2,4-bis(trifluoromethyl)benzyl bromide (140690-56-8) → 4-{[2,4-bis(trifluoromethyl)benzyl]oxy}-2-chlorobenzaldehyde (1264753-63-0)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 3.5h;	81%

3-(1-methylpiperidine-4-yl)propane-1-ol (7037-30-1) + 2-chloro-4-hydroxybenzaldehyde (56962-11-9) → 2-chloro-4-[3-(1-methyl-piperidin-4-yl)-propoxy]-benzaldehyde (848847-25-6)

Conditions	Yield
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 0 - 20℃; for 16h;	80%

2-chloro-4-hydroxybenzaldehyde (56962-11-9) + 6-anilinouracil (7269-15-0) → 8-Hydroxy-10-phenyl-10H-pyrimido[4,5-b]quinoline-2,4-dione (84459-38-1)

Conditions	Yield
In N,N-dimethyl-formamide for 5h; Heating;	79%

2-chloro-4-hydroxybenzaldehyde (56962-11-9) + [3-(2,6-dichlorophenyl)-5-(propan-2-yl)-1,2-oxazol-4-yl]methanol (278597-30-1) → 3-(2,6-dichlorophenyl)-4-(3'-chloro-4'-formylphenoxy)-methyl-5-isopropyl-isoxazole (278597-32-3)

Conditions	Yield
With di-isopropyl azodicarboxylate; triphenylphosphine In dichloromethane at 20℃; for 4h; Mitsunobu Displacement; Inert atmosphere;	78%
With di-isopropyl azodicarboxylate; thiamine diphosphate In dichloromethane at 20℃; for 4h; Mitsunobu reaction;	63%
With di-isopropyl azodicarboxylate; triphenylphosphine In dichloromethane at 20℃; for 4h; Mitsunobu reaction;	63%
With di-isopropyl azodicarboxylate; triphenylphosphine In dichloromethane at 0 - 20℃;

2-benzofuran-1(3H)-one (87-41-2) + 2-chloro-4-hydroxybenzaldehyde (56962-11-9) → N'-(2-chloro-4-hydroxybenzylidene)-2-(hydroxymethyl)benzohydrazide

Conditions	Yield
With hydrazine hydrate In ethanol at 78℃; for 8h; Green chemistry;	78%

4-(bromomethyl)-3-(2,6-dichlorophenyl)-5-isopropyl-isoxazole (898253-47-9) + 2-chloro-4-hydroxybenzaldehyde (56962-11-9) → 3-(2,6-dichlorophenyl)-4-(3'-chloro-4'-formylphenoxy)-methyl-5-isopropyl-isoxazole (278597-32-3)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 3h;	77%

2-chloro-4-hydroxybenzaldehyde (56962-11-9) + C15H18BrNO (1374961-76-8) → 2-chloro-4-{[3-(2,6-dimethylphenyl)-5-isopropylisoxazol-4-yl]methoxy}benzaldehyde (1374961-79-1)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 3h;	77%

Upstream product

• 108-43-0 3-monochlorophenol 
• 74-90-8 hydrogen cyanide 
• 3336-16-1 2-chloro-4-hydroxybenzonitrile 
• 76-03-9 trichloroacetic acid 
• 75-25-2 Bromoform 
• 67-66-3 chloroform 
• 874-42-0 2,4-dichlorobenzaldeyhde 
• 121-86-8 2-chloro-4-nitrotoluene 

Downstream Products

• 177275-02-4 2-chloro-4-(2-quinolylmethoxy)benzaldehyde 
• 179754-00-8 trifluoromethanesulfonic acid 3-chloro-4-formylphenyl ester 
• 933799-38-3 2-chloro-4-(5-isopropyl-3-naphthalen-2-ylisoxazol-4-ylmethoxy)benzaldehyde 
• 933799-42-9 4-[5-tert-butyl-3-(2,6-dichlorophenyl)isoxazol-4-ylmethoxy]-2-chlorobenzaldehyde 
• 933799-40-7 4-(3-biphenyl-4-yl-5-isopropylisoxazol-4-ylmethoxy)-2-chlorobenzaldehyde 
• 933799-44-1 4-[3-(2,6-dichlorophenyl)-5-phenylisoxazol-4-ylmethoxy]-2-chlorobenzaldehyde 
• 933799-46-3 2-chloro-4-[3-(2,6-dichlorophenyl)-5-naphthalen-2-ylisoxazol-4-ylmethoxy]benzaldehyde 
• 933799-48-5 4-[5-biphenyl-4-yl-3-(2,6-dichlorophenyl)isoxazol-4-ylmethoxy]-2-chlorobenzaldehyde 
• 638215-00-6 2-chloro-4-[((1R)-1-{6-[4-(trifluoromethyl)phenyl]-2-pyridinyl}pentyl)oxy]benzaldehyde 
• 638215-02-8 2-chloro-4-[((1S)-1-{6-[4-(trifluoromethyl)phenyl]-2-pyridinyl}pentyl)oxy]benzaldehyde 
• 845743-90-0 4-[((2S)-oxiran-2-yl) methoxy]-2-chlorobenzaldehyde 
• 114416-77-2 4-acetoxy-2-chlorobenzaldehyde 
• 1196879-38-5 4-(but-3-enyloxy)-2-chlorobenzaldehyde 
• 75427-52-0 3,10-Dimethyl-8-hydroxy-2,4(3H,10H)-pyrimido<4,5-b>chinolindion 

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