52577-09-0

Basic information

• Product Name: 3-(chloromethyl)-p-anisaldehyde
• Synonyms: 3-(chloromethyl)-p-anisaldehyde;Benzaldehyde, 3-(chloromethyl)-4-methoxy-;Einecs 258-015-5;3-(chloromethyl)-4-methoxybenzaldehyde(SALTDATA: FREE)
• CAS NO: 52577-09-0
• Molecular Formula: C₉H₉ClO₂
• Molecular Weight: 184.61956
• EINECS: 258-015-5
• Mol File: 52577-09-0.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 304.1°Cat760mmHg
• Flash Point: 135°C
• Appearance: /
• Density: 1.208g/cm³
• Vapor Pressure: 0.000895mmHg at 25°C
• Refractive Index: 1.56
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• CAS DataBase Reference: 3-(chloromethyl)-p-anisaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(chloromethyl)-p-anisaldehyde(52577-09-0)
• EPA Substance Registry System: 3-(chloromethyl)-p-anisaldehyde(52577-09-0)

Safety Data

• Hazardous Substances Data: 52577-09-0(Hazardous Substances Data)

Usage

Chemical Properties

Off-white Solid

Uses

3-Chloromethyl-4-methoxybenzaldehyde is a reactant in the preparation of inverse agonist for the human thyroid-stimulating hormone receptor.

InChI:InChI=1/C9H9ClO2/c1-12-9-3-2-7(6-11)4-8(9)5-10/h2-4,6H,5H2,1H3

Upstream product

• 123-11-5 4-methoxy-benzaldehyde 
• 7647-01-0 hydrogenchloride 
• 50-00-0 formaldehyd 
• 38870-89-2 Methoxyacetyl chloride 

Downstream Products

• 361187-13-5 2-(3-((2,6-dimethylphenoxy)methyl)-4-methoxyphenyl)-3-(furan-2-ylmethyl)-2,3-dihydroquinazolin-4(1H)-one 
• 1338824-20-6 NCG⁽²²⁹⁾C₀₀₆₀₀ 
• 1338824-21-7 N-(4-(5-(3-(furan-2-ylmethyl)-4-oxo-1,2,3,4-tetrahydroquinazolin-2-yl)-2-methoxybenzyloxy)-3,5-dimethylphenyl)acetamide 
• 1338824-24-0 N-(4-(2-methoxy-5-(4-oxo-3-(pyridin-3-ylmethyl)-1,2,3,4-tetrahydroquinazolin-2-yl)benzyloxy)-3,5-dimethylphenyl)acetamide 
• 1338824-25-1 N-(4-(2-methoxy-5-(3-(2-methoxyethyl)-4-oxo-1,2,3,4-tetrahydroquinazolin-2-yl)benzyloxy)-3,5-dimethylphenyl)acetamide 
• 1338824-22-8 N-(4-(5-formyl-2-methoxybenzyloxy)-3,5-dimethylphenyl)acetamide 
• 1564262-07-2 (E)-2-(chloromethyl)-1-methoxy-4-(3-methylbut-1-enyl)benzene 
• 932893-60-2 4-methoxy-3-[(4-methyl-piperazin-1-yl)methyl]-benzaldehyde 
• 932781-08-3 3-(N-ethylpiperazinyl-1)-methyl-4-methoxybenzaldehyde 
• 1609350-02-8 3-(N-phenylpiperazinyl-1)-methyl-4-methoxybenzaldehyde 

Relevant articles and documents

Alkylation of NH-, OH-, and SH-acids in the presence of potassium carbonate: 1. Functionalization of chloromethyl group of alkoxy-substituted aromatic aldehydes

An easily scalable, economocal, and more safe method for the preparation of 3-chloromethyl-4-methoxybenzaldehyde was developed. The latter was subjected to reactions with NH-, OH-, and SH-acids in the presence of potassium carbonate to obtain new aromatic aldehydes in high yields.

New chalcones containing nucleosides exhibiting in vitro anti-cancer activities

Twenty-one new chalcones 9a-m (excluding 9e, 9j and 9l) and 10a-m (excluding 10j and 10l), containing nucleobases were synthesized from 2'-hydroxyacetophenone (1) by the reactions including chloromethylation, nucleophilic substitution with thymine and uracil, and Claisen-Schmidt reactions. These new chalcones were evaluated for in vitro cytotoxicity against five human cancer cell lines: SK-LU-1, Hep-G2, MCF7, SW480 and P388. The results showed that most of the tested chalcones exhibited inhibitory activity against five cancer cell lines except 10h, and 10i. Among the synthesized chalcones, compound 10c exhibited most potent cytotoxicity against MCF-7, SK-LU-1, SW480, HepG2 and P388 with IC50 values of 4.42, 4.81, 5.27, 3.67 and 4.11μg/mL, respectively.

Synthesis of tetrapyrrole nitrogen mustards with potential anti-tumor activities

Eight porphyrin nitrogen mustards and six meso-tetraphenylporphin nitrogen mustards were synthesized. Most of the compounds possess both the chemotherapeutic and photochemotherapeutic effects on tumor.