2144-08-3

Basic information

• Product Name: 2,3,4-Trihydroxybenzaldehyde
• Synonyms: 2,3,4-TRIHYDROXYBENZALDEHYDE;PYROGALLOLALDEHYDE;PYROGALLOL-4-CARBOXALDEHYDE;2,3,4-Trihydroxybenazldehyde;2,3,4-THB;Pyrogallolcarboxaldehyde;2,3,4-TRIHYDROXYBENZALDEHYDE 98%;2,3,4-Trihydroxybenzaldehyde,98%
• CAS NO: 2144-08-3
• Molecular Formula: C₇H₆O₄
• Molecular Weight: 154.12
• EINECS: 218-404-2
• Product Categories: Aromatic Aldehydes & Derivatives (substituted);Benzaldehyde
• Mol File: 2144-08-3.mol
• Article Data: 4

Chemical Properties

• Melting Point: 159-161 °C(lit.)
• Boiling Point: 237.46°C (rough estimate)
• Flash Point: 150.6 °C
• Appearance: Light brown to beige-brown/Powder
• Density: 1.3725 (rough estimate)
• Vapor Pressure: 0.000573mmHg at 25°C
• Refractive Index: 1.6400 (estimate)
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility: DMSO, Methanol
• PKA: 7.41±0.23(Predicted)
• Water Solubility: 1.541g/L at 25℃
• Sensitive: Air Sensitive
• BRN: 2328658
• CAS DataBase Reference: 2,3,4-Trihydroxybenzaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3,4-Trihydroxybenzaldehyde(2144-08-3)
• EPA Substance Registry System: 2,3,4-Trihydroxybenzaldehyde(2144-08-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39-36
• WGK Germany: 2
• RTECS: CU8439800
• TSCA: Yes
• Hazardous Substances Data: 2144-08-3(Hazardous Substances Data)

Usage

Chemical Properties

light brown to beige-brown powder

Uses

Different sources of media describe the Uses of 2144-08-3 differently. You can refer to the following data:
1. 2,3,4-Trihydroxybenzaldehyde is a phenolic benzaldehyde with antibacterial activity.
2. 2,3,4-Trihydroxybenzaldehyde has been used in the preparation of 1,5-dimethyl-2-phenyl-4-[(1E)-(2,3,4-trihydroxybenzylidene)amino]-1H-pyrazol-3(2H)-one.

General Description

Antimicrobial activity of carbohydrazone derived from 2,3,4-trihydroxybenzaldehyde against bacteria and fungi has been investigated. 2,3,4-trihydroxybenzaldehyde forms Schiff bases via [1+1] condensation with anthranilic acid.

InChI:InChI=1/C7H6O4/c8-3-4-1-2-5(9)7(11)6(4)10/h1-3,9-11H

Synthetic route

C8H4O5 → 2,3,4-trihydroxybenzylaldehyde (2144-08-3)

Conditions	Yield
With water Reflux;	94.6%

N,N'-diphenylformamidine (864131-95-3) + 2-hydroxyresorcinol (87-66-1) → 2,3,4-trihydroxybenzylaldehyde (2144-08-3)

Conditions	Yield
at 110℃; und Kochen des Reaktionsprodukts mit Natronlauge;

Formanilid (103-70-8) + 2-hydroxyresorcinol (87-66-1) → 2,3,4-trihydroxybenzylaldehyde (2144-08-3)

Conditions	Yield
With diethyl ether; trichlorophosphate Zerlegen des ausgeschiedenen salzsauren Pyrogallolaldehydanilins durch Erwaeemen mit verd. Natronlauge;

hydrogen cyanide (74-90-8) + 2-hydroxyresorcinol (87-66-1) → 2,3,4-trihydroxybenzylaldehyde (2144-08-3)

Conditions	Yield
With hydrogenchloride; aluminium trichloride; benzene at 40℃; Zersetzung mit Eiswasser;
With hydrogenchloride; diethyl ether; zinc(II) chloride Zersetzung des sich ausscheidenden salzsauren Aldimids mit siedendem Wasser;
With hydrogenchloride

mercury fulminate (92114-96-0) + 2-hydroxyresorcinol (87-66-1) → 2,3,4-trihydroxybenzylaldehyde (2144-08-3)

Conditions	Yield
With hydrogenchloride; diethyl ether; mercury(II) fulminate Zerlegen des dabei erhaltenen Oxims durch Kochen mit verd. Schwefelsaeure;
With hydrogenchloride; diethyl ether; mercury(II) fulminate Zerlegen des dabei erhaltenen Oxims durch Kochen mit verd. Schwefelsaeure;

orthoformic acid triethyl ester (122-51-0) + 2-hydroxyresorcinol (87-66-1) → 2,3,4-trihydroxybenzylaldehyde (2144-08-3)

2,4-dihydroxy-3-O-α-L-rhamnopyranosylbenzaldehyde → L-rhamnose (6014-42-2) + 2,3,4-trihydroxybenzylaldehyde (2144-08-3)

Conditions	Yield
With hydrogenchloride; methanol for 4h; Reflux;

2,3,4-Trihydroxy-benzaldehyd-p-tolylimin (109103-74-4) → 2,3,4-trihydroxybenzylaldehyde (2144-08-3) + p-toluidine (106-49-0)

Conditions	Yield
With methanol; sodium tetrahydroborate
Multi-step reaction with 2 steps 1: [bis(acetoxy)iodo]benzene 2: sodium tetrahydroborate; methanol View Scheme

C14H11NO3 → 2,3,4-trihydroxybenzylaldehyde (2144-08-3) + p-toluidine (106-49-0)

Conditions	Yield
With methanol; sodium tetrahydroborate

bis(phenyl) carbonate (102-09-0) → 2,3,4-trihydroxybenzylaldehyde (2144-08-3)

Conditions	Yield
Multi-step reaction with 3 steps 1: triethylamine / tert-butyl methyl ether / Reflux 2: aluminum (III) chloride / tert-butyl methyl ether / 0 - 5 °C 3: water / Reflux View Scheme

2,3,4-trihydroxybenzylaldehyde (2144-08-3) + 11-(triisopropylsiloxy)undecyl bromide → TIPS3-CHO

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 85℃; for 4h;	100%

2,3,4-trihydroxybenzylaldehyde (2144-08-3) + benzyl bromide (100-39-0) → 2,3,4-tris(benzyloxy)benzaldehyde (27916-67-2)

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 80℃; for 16h; Inert atmosphere;	99%
With caesium carbonate In N,N-dimethyl-formamide at 80℃; for 16h; Inert atmosphere;	99%
With potassium carbonate; potassium iodide In N,N-dimethyl-formamide at 25℃; for 24h;	85%

(E)-3-(4-(hydrazinecarbonyl)phenyl)-N-hydroxyacrylamide (1223593-76-7) + 2,3,4-trihydroxybenzylaldehyde (2144-08-3) → Pandacostat (1224158-00-2)

Conditions	Yield
In dimethyl sulfoxide at 70℃; for 16h;	98%

2,3,4-trihydroxybenzylaldehyde (2144-08-3) + orthoformic acid triethyl ester (122-51-0) → C10H10O5 (952527-23-0)

Conditions	Yield
Stage #1: orthoformic acid triethyl ester With toluene-4-sulfonic acid In toluene for 0.5h; Dean-Stark; Molecular sieve; Reflux; Stage #2: 2,3,4-trihydroxybenzylaldehyde In toluene for 19h; Inert atmosphere; Reflux;	98%

2,3,4-trihydroxybenzylaldehyde (2144-08-3) + 5-amino-1-(4-hydroxyphenyl)-1H-imidazole-4-carbonitrile (849110-27-6) → C17H12N4O4 (1610624-80-0)

Conditions	Yield
With trifluoroacetic acid In ethanol at 20℃;	98%

2,3,4-trihydroxybenzylaldehyde (2144-08-3) + methyl iodide (74-88-4) → 2,3,4-trimethoxybenzaldehyde (2103-57-3)

Conditions	Yield
With potassium carbonate In acetone at 60℃; for 24h;	97.2%
With potassium carbonate In acetone at 80℃; for 12h; Inert atmosphere; Schlenk technique;	89%
With potassium carbonate In acetone

2,3,4-trihydroxybenzylaldehyde (2144-08-3) + 5-amino-1-(4-fluorophenyl)-1H-imidazole-4-carbonitrile → C17H11FN4O3 (1610624-94-6)

Conditions	Yield
With trifluoroacetic acid In ethanol at 20℃;	97%

4-nitrobenzeneacetic acid (104-03-0) + 2,3,4-trihydroxybenzylaldehyde (2144-08-3) → 7,8-diacetoxy-3-(4-nitrophenyl)coumarin

Conditions	Yield
Stage #1: 4-nitrobenzeneacetic acid; 2,3,4-trihydroxybenzylaldehyde With acetic anhydride; triethylamine at 90℃; Stage #2: In diethyl ether at 20℃;	97%

3.5-diaminobenzoic acid (535-87-5) + 2,3,4-trihydroxybenzylaldehyde (2144-08-3) → C21H16N2O8

Conditions	Yield
In methanol at 85℃; for 3h;	96%

2,3,4-trihydroxybenzylaldehyde (2144-08-3) + 1-dodecylbromide (143-15-7) → 2,3,4-tris(dodecyloxy)benzaldehyde (145533-22-8)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 3h;	95%
With potassium carbonate In N,N-dimethyl-formamide at 85℃; for 12h; Inert atmosphere;	92.76%
With potassium carbonate; potassium iodide In N,N-dimethyl-formamide at 80℃; for 12h;	80%

2,3,4-trihydroxybenzylaldehyde (2144-08-3) + terephthalohydrazide (136-64-1) → C22H18N4O8 (1622386-29-1)

Conditions	Yield
With acetic acid In methanol Reflux;	95%

cycl-isopropylidene malonate (2033-24-1) + 2,3,4-trihydroxybenzylaldehyde (2144-08-3) → 7,8-Dihydroxy-2-oxo-2H-1-benzopyran-3-carboxylic acid (19484-74-3)

Conditions	Yield
In water for 1h; Reflux;	95%
With ammonium acetate In water at 20℃; for 4h;	83%
With ammonium acetate In water at 20℃; for 4h;	83%

2-(2,5-dimethylthiazol-4-yl)acetohydrazide + 2,3,4-trihydroxybenzylaldehyde (2144-08-3) → (E)-2-(2,5-dimethyl-1,3-thiazol-4-yl)-N-(2,3,4-trihydroxybenzylidene)acetohydrazide

Conditions	Yield
With acetic acid In ethanol	95%

2,3,4-trihydroxybenzylaldehyde (2144-08-3) + N-tert.-Butoxycarbonyl-serinhydrazid (2766-42-9, 16882-36-3, 32988-38-8) → C15H21N3O7

Conditions	Yield
In isopropyl alcohol at 20℃; for 20h;	95%
In isopropyl alcohol at 50℃; for 2h; Inert atmosphere;	90.1%

2,3,4-trihydroxybenzylaldehyde (2144-08-3) + ethyl 2-cyanoacetate (105-56-6) → (E)-ethyl 2-cyano-3-(2,3,4-trihydroxyphenyl)acrylate

Conditions	Yield
With N-(propylcarbamoyl)sulfamic acid bonded on silica at 100℃; for 0.25h;	95%

2,3,4-trihydroxybenzylaldehyde (2144-08-3) → 2,3,4-trihydroxy benzonitrile

Conditions	Yield
With hydroxylamine hydrochloride In dimethyl sulfoxide at 90℃; for 2h;	95%

2,3,4-trihydroxybenzylaldehyde (2144-08-3) + chloromethyl methyl ether (107-30-2) → 2,3,4-tris(methoxymethoxy)benzaldehyde

Conditions	Yield
With sodium hydride In dichloromethane at 0℃; for 24h;	94%
With potassium carbonate In acetone for 0.5h;
With potassium carbonate In acetone at 0℃; for 4.5h; Inert atmosphere;

7,7,8,8,9,9,10,10,10-nonafluorodecyl bromide (457603-91-7) + 2,3,4-trihydroxybenzylaldehyde (2144-08-3) → 2,3,4-tris-(7,7,8,8,9,9,10,10,10-nonafluoro-decyloxy)-benzaldehyde (886575-45-7)

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

2,3,4-trihydroxybenzylaldehyde (2144-08-3) + 4-Aminosalicylic acid (65-49-6) → (E)-2-hydroxy-4-(2,3,4-trihydroxybenzylidene)aminobenzoic acid

Conditions	Yield
In methanol for 1h; Reflux;	94%
In methanol at 20℃; for 24h;

4-Methoxyphenylacetic acid (104-01-8) + 2,3,4-trihydroxybenzylaldehyde (2144-08-3) → 7,8-dihydroxy-3-(4'-methoxyphenyl)-2H-chromen-2-one (161942-57-0)

Conditions	Yield
With sodium acetate In acetic anhydride at 160℃; for 6h;	94%
With acetic anhydride; triethylamine at 110℃; for 6h; Green chemistry;	58%
Stage #1: 4-Methoxyphenylacetic acid; 2,3,4-trihydroxybenzylaldehyde With acetic anhydride; triethylamine at 112℃; for 1.16667h; Microwave irradiation; Green chemistry; Stage #2: With hydrogenchloride In ethanol; water at 80℃; for 3h; Green chemistry;	49%
Stage #1: 4-Methoxyphenylacetic acid; 2,3,4-trihydroxybenzylaldehyde With sodium acetate; acetic anhydride Stage #2: In methanol Acidic aq. solution;
With acetic anhydride; triethylamine at 112℃;

2,3,4-trihydroxybenzylaldehyde (2144-08-3) + 1,2-diamino-benzene (95-54-5) → 2-(2,3,4-trihydroxyphenyl)-1H-benzimidazole

Conditions	Yield
With sodium hydrogensulfite In ethanol; water at 80℃; for 24h;	94%

2,3,4-trihydroxybenzylaldehyde (2144-08-3) + 2-Amino-3-hydroxy-propionic acid hydrazide; hydrochloride → C10H13N3O5*ClH

Conditions	Yield
In methanol; water at 20℃; for 2h;	93.2%

2,3,4-trihydroxybenzylaldehyde (2144-08-3) + 1-bromo-5,5,6,6,7,7,8,8,9,9,10,10,10-tridecafluorodecane (181997-60-4) → 2,3,4-tris-(5,5,6,6,7,7,8,8,9,9,10,10,10-tridecafluoro-decyloxy)-benzaldehyde

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

4,6-dihydroxy-2-mercaptopyrimidine (504-17-6) + 2,3,4-trihydroxybenzylaldehyde (2144-08-3) → 2-thioxo-5-(2,3,4-trihydroxybenzylidene)dihydro-4,6(1H,5H)-pyrimidinedione (1208534-92-2)

Conditions	Yield
With sodium hydroxide at 20℃; for 12h;	93%
In water Reflux;	61%

(2,4,6-trichlorophenyl)hydrazine (5329-12-4) + 2,3,4-trihydroxybenzylaldehyde (2144-08-3) → 2,3,4-trihydroxybenzaldehyde N-(2,4,6-trichlorophenyl)hydrazone (389595-54-4)

Conditions	Yield
In methanol for 2h; Reflux;	93%

2,3,4-trihydroxybenzylaldehyde (2144-08-3) + isophthalic dihydrazide (2760-98-7) → C22H18N4O8 (1622386-34-8)

Conditions	Yield
With acetic acid In methanol Reflux;	93%

2,3,4-trihydroxybenzylaldehyde (2144-08-3) + 4-(8-{[(furan-2-yl)methyl]amino}-1,3-dimethyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-7-yl)butanehydrazide → 4-(8-((furan-2-ylmethyl)amino)-1,3-dimethyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-7-yl)-N'-(2,3,4-trihydroxybenzylidene)butanehydrazide

Conditions	Yield
With hydrogenchloride In methanol at 20℃; for 72h;	93%

6-Amino-1,3-dimethylbarbituric acid (6642-31-5) + 2,3,4-trihydroxybenzylaldehyde (2144-08-3) → C19H19N5O7

Conditions	Yield
With 1,1'-sulfinyldipyridinium bis (hydrogen sulfate) In ethanol at 20℃; for 1h; Green chemistry;	92%

N,N'-diethyl-2-thiobarbituric acid (5217-47-0) + 2,3,4-trihydroxybenzylaldehyde (2144-08-3) → 1,3-diethyl-2-thioxo-5-(2,3,4-trihydroxybenzylidene) dihydropyrimidine-4,6(1H,5H)-dione

Conditions	Yield
In water for 0.5h; Reflux;	92%
In water for 0.5h; Reflux;
In water for 0.5h; Reflux;

Upstream product

• 864131-95-3 N,N'-diphenylformamidine 
• 87-66-1 2-hydroxyresorcinol 
• 102-09-0 bis(phenyl) carbonate 
• 109103-74-4 2,3,4-Trihydroxy-benzaldehyd-p-tolylimin 
• 122-51-0 orthoformic acid triethyl ester 
• 92114-96-0 mercury fulminate 
• 74-90-8 hydrogen cyanide 
• 103-70-8 Formanilid 

Downstream Products

• 100727-75-1 N-(2,3,4-trihydroxy-benzylidene)-p-hydroxyaniline 
• 19283-70-6 3,4-dimethoxysalicylaldehyde 
• 41273-96-5 2,3,4-trihydroxy-5-morpholin-4-ylmethyl-benzaldehyde 
• 94008-46-5 5-(but-2'-enyl)-2,3,4-trihydroxybenzaldehyde 
• 2103-57-3 2,3,4-trimethoxybenzaldehyde 
• 41273-97-6 2,3,4-trihydroxy-5-piperidin-1-ylmethyl-benzaldehyde 
• 1033037-76-1 2,3,4-trihydroxy-5-(pyrrolidin-1-ylmethyl)benzaldehyde 
• 1292780-65-4 C₁₅H₁₁NO₄ 
• 1255947-93-3 7,8-diacetoxy-3-(3',5'-dimethoxyphenyl)coumarin 
• 1255948-00-5 7,8-dihydroxy-3-(3',5'-dihydroxyphenyl)coumarin 
• 1255947-96-6 7,8-diacetoxy-3-(3',5'-diacetoxyphenyl)coumarin 
• 1033037-98-7 2,3,4-trihydroxy-5-(dimethylaminomethyl)benzaldehyde 
• 1446450-96-9 N,N'-bis(2,3,4-trihydroxybenzylidene)-4,5-dimethyl-1,2-diaminobenzene 
• 5084-31-1 1,3,5,6-tetrahydroxy-xanthen-9-one 

Relevant articles and documents

Synthesis method of 2,3,4-trihydroxyl benzaldehyde

The invention provides a synthesis method of 2,3,4-trihydroxyl benzaldehyde, which is characterized in that pyrogallol is used as an initial raw material, and the synthesis of 2,3,4-trihydroxyl benzaldehyde comprises three steps of phenolic hydroxyl protection, formylation and de-protection. The method has the advantages of cheap and easily available raw materials, simple operation, high product yield and purity, and small amount of three wastes, and has excellent economic and environmental benefits.

Benzyl and benzaldehyde-derived metabolites from desert actinomycetes Sp. CDS

Chromatographic purification of the culture broth of Actinomycetes CDS1 provided five new (1-5) and three known (6-8) metabolites. The new compounds 1, 4 and 5 were elucidated due to 1D-, 2D-NMR techniques, FABMS and HR-FABMS analyses. The nature of glycosidic part in 4 was confirmed through optical rotation value and comparison of the Rf value of hydrolyzed sugar with that of standard sample. Compounds 2 and 3 were tentatively identified due to 1H NMR and +ve FAB-MS analysis as mixture in one of the polar minor fractions. Structures of the known compounds 6-8 were determined due to 1H NMR and FABMS analysis.