2,4-Dihydroxybenzaldehyde

Base Information

• Chemical Name: 2,4-Dihydroxybenzaldehyde
• CAS No.: 95-01-2
• Deprecated CAS: 1060789-59-4,2295913-47-0
• Molecular Formula: C7H6O3
• Molecular Weight: 138.123
• Hs Code.: 29124900
• European Community (EC) Number: 202-383-1
• NSC Number: 8690
• UNII: 772JOF6LZS
• DSSTox Substance ID: DTXSID8021806
• Nikkaji Number: J4.706F
• Wikidata: Q27121977
• Metabolomics Workbench ID: 57363
• ChEMBL ID: CHEMBL243587
• Mol file: 95-01-2.mol

Synonyms:2,4-DIHYDROXYBENZALDEHYDE;95-01-2;beta-Resorcylaldehyde;4-Hydroxysalicylaldehyde;4-Formylresorcinol;Benzaldehyde, 2,4-dihydroxy-;beta-Resorcaldehyde;beta-Resorcinaldehyde;beta-Resorcylic aldehyde;2,4-Dihydroxybenzenecarbonal;Salicylaldehyde, 4-hydroxy-;4-Hydroxysalicyladehyde;.beta.-Resorcylaldehyde;2,4-Dihydroxybenzaldehyd;beta-Rosorcaldehyde;NSC 8690;MFCD00011686;.beta.-Resorcaldehyde;CHEBI:50198;.beta.-Resorcinaldehyde;EINECS 202-383-1;.beta.-Resorcylic aldehyde;UNII-772JOF6LZS;BRN 0878548;772JOF6LZS;AI3-24367;CHEMBL243587;NSC8690;NSC-8690;b-resorcylaldehyde;4-08-00-01753 (Beilstein Handbook Reference);2,4-dihydroxy-benzaldehyde;Resorcinal;b-Resorcaldehyde;b-Resorcinaldehyde;A-Resorcylaldehyde;b-Resorcylic aldehyde;Beta-resorcyl aldehyde;2,4dihydroxybenzaldehyde;24-Dihydroxybenzaldehyde;2,4-Dihyroxybenzaldehyde;2,4 dihydroxybenzaldehyde;2,4-dihydoxy-benzaldehyde;2,4-dihydroxylbenzaldehyde;2,4,-dihydroxybenzaldehyde;2,4-dihydroxy benzaldehyde;2,4-dihydroxyl benzaldehyde;SCHEMBL93513;MLS001076174;2,4-bis(oxidanyl)benzaldehyde;DTXSID8021806;2,4-Dihydroxybenzaldehyde, 98%;HMS2270K22;AMY25823;STR01512;DIHYDROXYBENZALDEHYDE, 2,4-;BBL012171;BDBM50140239;STK299744;.BETA.-RESORCYLALDEHYDE [MI];AKOS000118990;CS-W007539;HY-W007539;NCGC00247446-01;AC-24172;SMR000639137;SY007063;LS-143426;D0564;FT-0610123;EN300-21460;F11148;A845149;A934060;AP-065/40195541;W-100175;Q27121977;F1995-0226;Z104497974;2,4-Dihydroxybenzaldehyde, Vetec(TM) reagent grade, 98%

Chemical Property of 2,4-Dihydroxybenzaldehyde

Chemical Property:

• Appearance/Colour: cream to light brown solid
• Vapor Pressure: 2.13E-05mmHg at 25°C
• Melting Point: 135-137 °C(lit.)
• Refractive Index: 1.674
• Boiling Point: 350.7 °C at 760 mmHg
• PKA: 7.56±0.18(Predicted)
• Flash Point: 165.9 °C
• PSA: 57.53000
• Density: 1.409 g/cm³
• LogP: 0.91030
• Storage Temp.: -20?C Freezer
• Sensitive.: Air Sensitive
• Solubility.: DMSO (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)
• Water Solubility.: soluble
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 138.031694049
• Heavy Atom Count: 10
• Complexity: 124

Purity/Quality:

99% ^*data from raw suppliers

2,4-Dihydroxybenzaldehyde ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,Xi
• Hazard Codes: Xn,Xi
• Statements: 22-36/37/38
• Safety Statements: 26-36-37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC(=C(C=C1O)O)C=O
• General Description: 2,4-Dihydroxybenzaldehyde, also known as b-Resorcylaldehyde, is a chemical compound used in the synthesis of chiral liquid crystal dimers, where it contributes to the formation of optically active mesophases with unique properties such as re-entrant phases and biaxial smectic structures. Additionally, it serves as a reactant in Co(III)-catalyzed asymmetric ring-opening reactions, where its phenolic groups participate in the reaction, and its structural features influence enantioselectivity and reaction kinetics. The compound's versatility in forming complex structures highlights its utility in materials science and asymmetric synthesis.

Technology Process of 2,4-Dihydroxybenzaldehyde

There total 49 articles about 2,4-Dihydroxybenzaldehyde which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 96.0%

chloroform (67-66-3,8013-54-5) + recorcinol (108-46-3) → 2,4-Dihydroxybenzaldehyde (95-01-2)

Guidance literature:

With sodium hydroxide; β‐cyclodextrin; In water; at 60 ℃; for 8h;

DOI:10.1021/ja00345a058

Reference yield: 93.0%

N,N-dimethyl-formamide (68-12-2,33513-42-7) + recorcinol (108-46-3) → 2,4-Dihydroxybenzaldehyde (95-01-2)

Guidance literature:

With trichlorophosphate; at 0 - 60 ℃; for 8h; Inert atmosphere;

Reference yield: 92.0%

2,4-diacetoxybenzaldehyde (41777-08-6) → 2,4-Dihydroxybenzaldehyde (95-01-2)

Guidance literature:

With water; sodium acetate; In ethanol; for 5h; Reflux;

DOI:10.1080/00397910802621731

upstream raw materials:

3-formyl-2,6-dihydroxy-benzoic acid

salicylaldehyde

formamide

recorcinol

Downstream raw materials:

2-Hydroxy-4-methoxybenzaldehyde

2,4-Dimethoxybenzaldehyde

7-hydroxy-3-(phenylcarbonyl)-2H-chromen-2-one

7-hydroxy-2H-chromen-2-one

Refernces

2-Hydroxybenzaldehyde (2-phenylquinazolin-4-yl)hydrazones and their Zn ^II complexes: Synthesis and photophysical properties

10.1007/s11172-011-0360-z

The research focuses on the synthesis and photophysical properties of 2-hydroxybenzaldehyde (2-phenylquinazolin-4-yl)hydrazones and their ZnII complexes. The purpose of this study was to extend the synthesis of fluorine-containing quinazoline derivatives and to investigate their potential as luminescent materials, given that nitrogen heterocyclic derivatives with a phenolic OH group are known as effective ligands and many complexes based on o-hydroxy azomethines exhibit luminescent properties. The researchers synthesized a series of new quinazoline derivatives and their zinc(II) complexes, examining their structures and luminescent properties. The chemicals used in this process included 2-aminobenzonitrile, salicylaldehyde, 2-hydroxy-5-nitrobenzaldehyde, 4-hydroxysalicylaldehyde, 3,5-dibromosalicylaldehyde, and various substituted hydrazines. The study concluded that the synthesized hydrazones and their ZnII complexes exhibited interesting photophysical properties, with the complexation process leading to a bathochromic shift in the absorption spectra and blue shifts in the emission peaks. The researchers also noted that the complexation considerably lowered the Stokes shift and increased the quantum yield, suggesting that these quinazoline-containing hydrazones are promising ligand systems for the design of complexes with other metals, potentially useful in electroluminescent materials and organic light-emitting diodes (OLEDs).

Optically Biaxial, Re-entrant and Frustrated Mesophases in Chiral, Non-symmetric Liquid Crystal Dimers and Binary Mixtures

10.1002/asia.201600918

The research focuses on the synthesis and characterization of sixteen optically active, non-symmetric liquid crystal dimers and their binary mixtures. The dimers were created by interlinking cyanobiphenyl and salicylaldimine mesogens with a flexible spacer, varying the number of methylene units from 3 to 10 to form eight pairs of (R & S) enantiomers. Key chemicals involved in the synthesis include 4-hydroxy-4-cyanobiphenyl, a,w-dibromoalkanes, 2,4-dihydroxybenzaldehyde, (R)- and (S)-2-octanol, and 4-nitrophenol. The study utilized various techniques such as polarizing optical microscopy (POM), differential scanning calorimetry (DSC), and X-ray powder diffraction (XRD) to investigate the thermal properties and phase transitions of these dimers. The research revealed a variety of mesophases, including chiral nematic (N*), twist grain boundary (TGB), blue phases (BPs), and biaxial smectic A (SmAb) phases, with notable occurrences of re-entrant phases and interdigitated or intercalated smectic structures. The findings provide insights into the structure–property correlations in chiral liquid crystal systems and contribute to the development of novel materials with unique optical and structural properties.

Co(III) catalysed asymmetric ring-opening of epichlorohydrin by salicylaldehyde derivatives: Reversal of enantioselectivity and rate acceleration on addition of AlCl₃

10.3906/kim-1005-607

The research investigates the asymmetric ring-opening of epichlorohydrin by salicylaldehyde derivatives using Co(III) salen catalysts. The study found that the ring-opening occurred at the phenolic groups most distant from the aldehydic group. Notably, switching catalysts led to a reversal in enantioselectivity. The addition of AlCl3 to the reaction mixture significantly accelerated the reaction rate without compromising product enantiopurity. Key chemicals involved in the research include epichlorohydrin, 2,3-dihydroxybenzaldehyde, 2,4-dihydroxybenzaldehyde, salicylaldehyde, Co(III) salen catalysts (1a and 1b), and AlCl3. The study also involved the synthesis of oximes and benzisoxazoles as part of the product characterization process.