2-Carboxybenzaldehyde

Base Information

• Chemical Name: 2-Carboxybenzaldehyde
• CAS No.: 119-67-5
• Molecular Formula: C8H6O3
• Molecular Weight: 150.134
• Hs Code.: 29183000
• European Community (EC) Number: 204-342-3
• NSC Number: 5045
• UNII: OAEGSO7G3Y
• DSSTox Substance ID: DTXSID1059490
• Nikkaji Number: J95.028I
• Wikipedia: 2-Carboxybenzaldehyde
• Wikidata: Q27102472
• Metabolomics Workbench ID: 50972
• ChEMBL ID: CHEMBL234213
• Mol file: 119-67-5.mol

Synonyms:2-Carboxybenzaldehyde;119-67-5;2-Formylbenzoic acid;PHTHALALDEHYDIC ACID;o-Formylbenzoic acid;Benzoic acid, 2-formyl-;o-Carboxybenzaldehyde;MFCD00003336;Benzoic acid, formyl-;OAEGSO7G3Y;NSC 5045;EINECS 204-342-3;BRN 0742381;Benzaldehyde-2-carboxylic Acid;CHEBI:17605;NSC-5045;4-10-00-02748 (Beilstein Handbook Reference);Phthalaldehydsure;formylbenzoic acid;carboxybenzaldehyde;2-formyl benzoic acid;2-formyl-benzoic acid;2- carboxybenzaldehyde;2-carboxy-benzaldehyde;UNII-OAEGSO7G3Y;SCHEMBL78873;2-Carboxybenzaldehyde, 97%;CHEMBL234213;DTXSID1059490;BENZALDEHYDE, 2-CARBOXY-;NSC5045;CS-D1667;HY-Y1771;BBL013693;STK801573;AKOS000120931;AS-14466;BP-11499;SY001395;LS-109067;AM20060492;FT-0611650;FT-0657534;P0281;2-FORMYL BENZOIC ACID [USP IMPURITY];EN300-20473;C03057;AP-065/41884108;Q27102472;F2191-0166;Z104478340

Chemical Property of 2-Carboxybenzaldehyde

Chemical Property:

• Appearance/Colour: white crystal powder
• Vapor Pressure: 0.00012mmHg at 25°C
• Melting Point: 94-96 °C(lit.)
• Refractive Index: 1.4500 (estimate)
• Boiling Point: 321.8 °C at 760 mmHg
• PKA: 4.57±0.10(Predicted)
• Flash Point: 162.6 °C
• PSA: 54.37000
• Density: 1,404 g/cm³
• LogP: 1.19730
• Storage Temp.: Store below +30°C.
• Sensitive.: Air Sensitive
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• Water Solubility.: soluble
• XLogP3: 1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 150.031694049
• Heavy Atom Count: 11
• Complexity: 165

Purity/Quality:

99.9% ^*data from raw suppliers

2-Carboxybenzaldehyde ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi,Xn
• Statements: 36/37/38-20/21/22
• Safety Statements: 26-36-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C(=C1)C=O)C(=O)O
• General Description: 2-Carboxybenzaldehyde (also known as 2-formylbenzoic acid) serves as a key reactant in the Ugi four-component condensation (Ugi-4CC) to form stable primary adducts, which can be further transformed into isocoumarins. Its reactivity with phenacylamine dimethyl acetal and isocyanides under controlled conditions allows for the isolation and characterization of intermediates, demonstrating its utility in synthetic routes toward biologically relevant heterocycles. 2-Carboxybenzaldehyde's stability in solid state and tendency to rearrange in solution highlight its role in facilitating efficient and tunable chemical transformations.

Technology Process of 2-Carboxybenzaldehyde

There total 97 articles about 2-Carboxybenzaldehyde 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: 74.0%

o-xylene (95-47-6) → ortho-methylbenzoic acid (118-90-1) + 2-benzofuran-1(3H)-one (87-41-2) + benzene-1,2-dicarboxylic acid (88-99-3,73607-73-5) + benzoic acid (65-85-0,8013-63-6) + o-carboxybenzaldehyde (119-67-5)

Guidance literature:

With dihydrogen peroxide; In water; at 380 ℃; under 172517 Torr; Product distribution / selectivity; Supercritical conditions;

Reference yield: 73.0%

o-xylene (95-47-6) → ortho-methylbenzoic acid (118-90-1) + 2-(hydroxymethyl)benzoic acid (612-20-4) + benzene-1,2-dicarboxylic acid (88-99-3,73607-73-5) + o-carboxybenzaldehyde (119-67-5)

Guidance literature:

o-xylene; With N-hydroxyphthalimide; air; cobalt(II) acetate; manganese(II) acetate; In acetic acid; at 150 ℃; for 3h; under 22801.5 Torr;

With sodium hydroxide; at 90 ℃; Further stages.;

DOI:10.1002/1615-4169(20010226)343:2<220::aid-adsc220>3.0.co;2-n

Reference yield: 72.0%

o-xylene (95-47-6) → 2-benzofuran-1(3H)-one (87-41-2) + benzene-1,2-dicarboxylic acid (88-99-3,73607-73-5) + benzoic acid (65-85-0,8013-63-6) + o-carboxybenzaldehyde (119-67-5)

Guidance literature:

With dihydrogen peroxide; In water; at 380 ℃; under 172517 Torr; Product distribution / selectivity; Supercritical conditions;

upstream raw materials:

3-Bromophthalide

2-carboxycinnamic acid

phthalonic acid

2-dichloromethyl-benzonitrile

Downstream raw materials:

3-morpholin-4-yl-3H-isobenzofuran-1-one

2-(3-oxo-5,6-dihydro-imidazo[2,1-b]thiazol-2-ylidenemethyl)-benzoic acid

3-(1H-indol-3-yl)isobenzofuran-1(3H)-one

2-Methyl-3-phthalidyl-indol

Refernces

Isolation of Ugi four-component condensation primary adducts: A straightforward route to isocoumarins

10.1021/ol9028622

The research presents a study on the isolation of primary adducts from Ugi four-component condensation (Ugi-4CC), which leads to the formation of isocoumarins. The researchers used 2-formylbenzoic acid, phenacylamine dimethyl acetal, and isocyanides as reactants and successfully isolated the primary adducts, which were stable enough for characterization. They also found that using anilines instead of amines yielded stable isocoumarins. The experiments involved stirring the reactants in methanol, followed by filtration to isolate the yellow solid product. The product's structure was confirmed through analytical and spectral data, as well as X-ray diffraction analysis. The study also explored the rearrangement of these primary adducts to form "normal" Ugi-4CC adducts upon treatment with acid and the deprotected Ugi-4CC adducts when exposed to higher concentrations of hydrochloric acid. The researchers highlighted the importance of controlling reaction conditions to ensure good yields and easy workup of the compounds, which were found to be stable in solid state but tended to rearrange in solution. The study provides a straightforward route to isocoumarins, a class of compounds with various biological activities.