35773-43-4

Basic information

• Product Name: Disperse Yellow 232
• Synonyms: 3-(5-chloro-2-benzoxazolyl)-7-(diethylamino)-2h-1-benzopyran-2-on;3-(5-Chlorobenzoxazol-2-yl)-7-diethylaminocoumarin;SOLVENT YELLOW 160:1;Yellow 10G;c.i. 55165;Disperse Yellow 232;ELBAPLAST FLUORESCENT YELLOW GN;3-(5-chloro-2-benzoxazolyl)-7-(diethylamino)-2h-1-benzopyran-2-one
• CAS NO: 35773-43-4
• Molecular Formula: C₂₀H₁₇ClN₂O₃
• Molecular Weight: 368.81
• EINECS: 252-722-2
• Mol File: 35773-43-4.mol

Chemical Properties

• Melting Point: 195-196 °C(Solv: N,N-dimethylformamide (68-12-2))
• Boiling Point: 575.4 °C at 760 mmHg
• Flash Point: 301.8 °C
• Appearance: /
• Density: 1.354
• Vapor Pressure: 0Pa at 20℃
• PKA: 2.88±0.20(Predicted)
• CAS DataBase Reference: Disperse Yellow 232(CAS DataBase Reference)
• NIST Chemistry Reference: Disperse Yellow 232(35773-43-4)
• EPA Substance Registry System: Disperse Yellow 232(35773-43-4)

Safety Data

• Hazardous Substances Data: 35773-43-4(Hazardous Substances Data)

Usage

Flammability and Explosibility

Notclassified

InChI:InChI=1/C20H17ClN2O3/c1-3-23(4-2)14-7-5-12-9-15(20(24)26-18(12)11-14)19-22-16-10-13(21)6-8-17(16)25-19/h5-11H,3-4H2,1-2H3

Synthetic route

4-(Diethylamino)salicylaldehyde (17754-90-4) + ethyl 2-cyanoacetate (105-56-6) + 2-hydroxy-5-chloro-aniline (95-85-2) → 3-(5-chloro-1,3-benzoxazol-2-yl)-7-(diethylamino)-2H-chromen-2-one (35773-43-4)

Conditions	Yield
With benzoic acid In pentan-1-ol at 110℃; for 0.05h; Microwave irradiation;	92%
With oxalic acid; L-proline In ethanol at 85℃; for 12h; Schlenk technique;	83%
With acetic acid In glycerol at 80℃; for 14h; Schlenk technique; Green chemistry;	75%
In butan-1-ol for 7h; Reflux;	73%

4-(Diethylamino)salicylaldehyde (17754-90-4) + diethyl malonate (105-53-3) + 2-hydroxy-5-chloro-aniline (95-85-2) → 3-(5-chloro-1,3-benzoxazol-2-yl)-7-(diethylamino)-2H-chromen-2-one (35773-43-4)

Conditions	Yield
With pyrophosphoric acid at 100℃; for 0.1h; Microwave irradiation;	70%

Upstream product

• 17754-90-4 4-(Diethylamino)salicylaldehyde 
• 105-56-6 ethyl 2-cyanoacetate 
• 95-85-2 2-hydroxy-5-chloro-aniline 
• 105-53-3 diethyl malonate 

Relevant articles and documents

Glycerol and acetic acid assisted mild strategy for facile synthesis of 3-heteroarylcoumarins via three-component reaction

A feasible and inexpensive reaction system for synthesis of 3-benzoxazol-2-yl-chromen-2-one as a kind of 3-heteroarylcoumarins has been developed. Both acetic acid and glycerol are simple, cheap and common chemicals, the combination of them could smoothly accelerate the three-component one-pot reaction of salicylaldehyde, o-aminophenol and ethyl cyanoacetate to yield 3-heteroarylcoumarins. This process not only offers the products in good to excellent yields but also avoids the problems associated with catalyst cost, handling, safety and pollution. Compared with the literature, the reaction temperature successfully reduced to 80?°C. As an application, disperse yellow 232 was furnished with a satisfactory yield under optimum reaction conditions. In addition, all synthesized 3-heteroarylcoumarins were preliminary evaluated the inhibitory effect against human carboxylesterase 1. This protocol offers an expedient strategy for efficient synthesis of 3-heteroarylcoumarins that are widely present in biologically active compounds and fluorescent paints.

Mild and efficient prepare disperse yellow 184, disperse yellow 232 and their analogues via LTTM promoted three-component reaction

A convenient protocol for the synthesis of disperse yellow 184, disperse yellow 232 and their analogues via a three-component one-pot reaction of salicylaldehyde, o-aminophenol and ethyl cyanoacetate has been established. Cheap and eco-friendly ethanol was employed as solvent. One drop of low-transition-temperature mixture (LTTM) which formed from l(?)-Proline and oxalic acid could smoothly promote the reaction of 0.5 mmol raw materials. Compared to the classical methodologies, the present pathway has broad reaction scope and affords all products in good to excellent yields. Furthermore, this process could reduce the reaction temperature from 135 to 85 °C and avoid the problems associated with catalyst cost, handling, safety and pollution. On the basis of comparative experiments and DFT calculation, possible mechanism of this strategy is discussed in detail.

One-pot catalyst-free synthesis of 3-heterocyclic coumarins

3-Heterocyclic coumarins were prepared in one-pot three-component reaction without catalyst. The mixture of salicylaldehydes, ethyl cyanoacetate, and o-aminophenols or o-phenylenediamines in refluxing n-butanol gave title compounds with good yields and hi

Microwave-promoted one-pot syntheses of coumarin dyes

To one pot synthesis of coumarins with benzimidazol or benzoxazol moieties, three different microwave irradiations based procedures are reported here which take place within a few minutes. In spite of fairly well yield of the products using solvent free procedures, 25-30% further yields were achieved within 3 minutes at 110C using 2mL n-pentanol as solvent.