4-Chloro-2-formylbenzoic acid

Base Information

• Chemical Name: 4-Chloro-2-formylbenzoic acid
• CAS No.: 4657-56-1
• Molecular Formula: C8H5ClO3
• Molecular Weight: 184.579
• Hs Code.: 2918300090
• DSSTox Substance ID: DTXSID70452976
• Nikkaji Number: J60.356B
• Wikidata: Q82273912
• Mol file: 4657-56-1.mol

Synonyms:4-chloro-2-formylbenzoic acid;4657-56-1;2-Formyl-4-chlorobenzoic Acid;4-chloro-2-formylbenzoicacid;Benzoic acid, 4-chloro-2-formyl-;SCHEMBL78586;DTXSID70452976;UAEFASLCDWQSDH-UHFFFAOYSA-N;MFCD18453660;AKOS005209322;BS-16847;CS-0160858;D80343;EN300-150694

Chemical Property of 4-Chloro-2-formylbenzoic acid

Chemical Property:

• Melting Point: 184-186 °C
• Boiling Point: 347.3±27.0 °C(Predicted)
• PKA: 4.34±0.10(Predicted)
• PSA: 54.37000
• Density: 1.469±0.06 g/cm3(Predicted)
• LogP: 1.85070
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 183.9927217
• Heavy Atom Count: 12
• Complexity: 193

Purity/Quality:

98%min ^*data from raw suppliers

4-Chloro-2-formylbenzoicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=C(C=C1Cl)C=O)C(=O)O
• Uses: 4-Chloro-2-formylbenzoic Acid?is a useful reagent to prepare 3-(3-oxoalkyl)isocoumarins by tandem reductive rearrangement of 3-furylphthalides. ?It is also a suitable compound to synthesize 2-substituted-3-(1H-indol-3-yl)isoindolin-1-one derivatives in water without catalyst.

Technology Process of 4-Chloro-2-formylbenzoic acid

There total 7 articles about 4-Chloro-2-formylbenzoic acid 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: 85.0%

methyl 4-chloro-2-formylbenzoate (1001336-16-8) → 4-chloro-2-formylbenzoic acid (4657-56-1)

Guidance literature:

With water; lithium hydroxide; In methanol; at 20 ℃;

Reference yield: 75.0%

2-formyl-4-chloro-N-methylbenzamide (640286-60-8) → 4-chloro-2-formylbenzoic acid (4657-56-1)

Guidance literature:

With hydrogenchloride; water; for 18h; Heating / reflux; Alkaline aqueous solution;

Reference yield:

2-bromo-4-chlorobenzoic acid (936-08-3) + N,N-dimethyl-formamide (68-12-2,33513-42-7) → 4-chloro-2-formylbenzoic acid (4657-56-1)

Guidance literature:

2-bromo-4-chlorobenzoic acid; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 0.5h; Inert atmosphere;

N,N-dimethyl-formamide; In tetrahydrofuran; hexane; at -78 ℃; Inert atmosphere;

DOI:10.1016/j.tetlet.2018.03.024

upstream raw materials:

3-bromo-5-chloroisobenzofuran-1(3H)-one

5-chloro-3H-isobenzofuran-1-one

5-amino-3H-isobenzofuran-1-one

2-formyl-4-chloro-N-methylbenzamide

Downstream raw materials:

5-chloro-2-(morpholine-4-carbonyl)benzaldehyde

C₁₄H₁₀ClNO

methyl 4-chloro-2-formylbenzoate

2-benzyl-5-chloro-3-(1H-indol-3-yl)isoindolin-1-one

Refernces

• 1、 Meng, Jiao-Long,Jiao, Tang-Qian,Chen, Ya-Heng,Fu, Rui,Zhang, Shu-Sheng,Zhao, Qian,Feng, Chen-Guo,Lin, Guo-Qiang. "Synthesis of chiral isoindolinones via asymmetric propargylation/lactamization cascade". supporting information. p. 1564 - 1567. Retrieved 2018/03/23.
• 2、 Fronert, Jeanne,Bisschops, Tom,Cassens-Sasse, Elisa,Atodiresei, Iuliana,Enders, Dieter. "Asymmetric organocatalytic synthesis of trans -3,4-disubstituted isochromanones via an intramolecular aldol reaction". . p. 1708 - 1712. Retrieved 2013/07/19.