4433-79-8

Basic information

• Product Name: 4'-Chloro-2',5'-dimethoxyacetoacetanilide
• Synonyms: 4′-Chlor-2′,5′-dimethoxyacetoacetanilid;ACETOACET-2,5-DIMETHOXY-4-CHLORO ANILINE;chinizol;Sanatol IRG;Yellow Base GC.;As-Irg4-Chloro-2.5-DimethoxyCetoacetoANilide;Acetoaceto-4-chloro-2, 5-dimethoxyanilide;N-(4-chloro-2,5-dimethoxy-phenyl)-3-keto-butyramide
• CAS NO: 4433-79-8
• Molecular Formula: C₁₂H₁₄ClNO₄
• Molecular Weight: 271.7
• EINECS: 224-638-6
• Product Categories: Intermediates of Dyes and Pigments;Aromatic amine products
• Mol File: 4433-79-8.mol
• Article Data: 5

Chemical Properties

• Melting Point: 102-104°C
• Boiling Point: 432.7 °C at 760 mmHg
• Flash Point: 215.5 °C
• Appearance: off-white powder
• Density: 1.277
• Vapor Pressure: 0-0.001Pa at 20-50℃
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 10.75±0.46(Predicted)
• CAS DataBase Reference: 4'-Chloro-2',5'-dimethoxyacetoacetanilide(CAS DataBase Reference)
• NIST Chemistry Reference: 4'-Chloro-2',5'-dimethoxyacetoacetanilide(4433-79-8)
• EPA Substance Registry System: 4'-Chloro-2',5'-dimethoxyacetoacetanilide(4433-79-8)

Safety Data

• TSCA: Y
• Hazardous Substances Data: 4433-79-8(Hazardous Substances Data)

Usage

Description

4'-Chloro-2',5'-dimethoxyacetoacetanilide is an organic compound with the chemical formula C11H12ClNO4. It is an off-white powder that serves as an intermediate in the synthesis of various organic pigments. 4'-Chloro-2',5'-dimethoxyacetoacetanilide is known for its fastness and is particularly suitable for use in the dyeing and printing of cotton fabrics.

Uses

Used in Textile Industry:
4'-Chloro-2',5'-dimethoxyacetoacetanilide is used as a dyeing agent for cotton fabric, specifically for dyeing and printing processes. It is not suitable for cotton yarn dyeing due to its low affinity for cotton. 4'-Chloro-2',5'-dimethoxyacetoacetanilide is ideal for cotton products that require higher fastness and is generally not used for contaminated materials.
Used in Organic Pigments Industry:
4'-Chloro-2',5'-dimethoxyacetoacetanilide is used as an intermediate in the manufacture of organic pigments. Its role in the production process is crucial for creating pigments with desired properties and characteristics.

Preparation

4-Chloro-2,5-dimethoxybenzenamine and Ethyl 3-oxobutanoate or 4-Methyleneoxetan2-onecondensation.

Synthetic route

4-methyleneoxetan-2-one (674-82-8) + 4-chloro-2,5-dimethoxy-aniline (6358-64-1) → 1-acetoacetylamino-4-chloro-2,5-dimethoxy-benzene (4433-79-8)

Conditions	Yield
In ethanol at 30 - 60℃; for 6h; Temperature;	98.6%

sodium aceto-acetate (623-58-5) + 4-chloro-2,5-dimethoxy-aniline (6358-64-1) → 1-acetoacetylamino-4-chloro-2,5-dimethoxy-benzene (4433-79-8)

Conditions	Yield
In chlorobenzene for 6h;	92%

ethyl acetoacetate (141-97-9) + 4-chloro-2,5-dimethoxy-aniline (6358-64-1) → 1-acetoacetylamino-4-chloro-2,5-dimethoxy-benzene (4433-79-8)

Conditions	Yield
With potassium tert-butylate at 120℃; for 2h; Microwave irradiation;

acetylketene (691-45-2) + 4-chloro-2,5-dimethoxy-aniline (6358-64-1) → 1-acetoacetylamino-4-chloro-2,5-dimethoxy-benzene (4433-79-8)

Conditions	Yield
at 25℃; for 2h; Temperature;

1-acetoacetylamino-4-chloro-2,5-dimethoxy-benzene (4433-79-8) → C12H17ClN2O3

Conditions	Yield
With ammonia; hydrogen In tetrahydrofuran at 120℃; for 24h;	85%

[bis(acetoxy)iodo]benzene (3240-34-4) + 1-acetoacetylamino-4-chloro-2,5-dimethoxy-benzene (4433-79-8) → 1-(4-chloro-2,5-dimethoxyphenylcarbamoyl)-2-oxopropyl acetate (1353648-04-0)

Conditions	Yield
In 1,2-dichloro-ethane at 20℃; for 2h;	80%

1-acetoacetylamino-4-chloro-2,5-dimethoxy-benzene (4433-79-8) → 2,2-dichloro-N-(4-chloro-2,5-dimethoxyphenyl)acetamide (42276-58-4)

Conditions	Yield
With [bis(acetoxy)iodo]benzene; zinc(II) chloride In 1,4-dioxane at 20℃; for 1h;	80%
With iodine trichloride In 1,2-dichloro-ethane at 20℃; for 3h; Schlenk technique;	69%

1-acetoacetylamino-4-chloro-2,5-dimethoxy-benzene (4433-79-8) → 2-(4-chloro-2,5-dimethoxyphenyl)-5-methylisoxazole-3(2H)-one (1417647-05-2)

Conditions	Yield
With [bis(acetoxy)iodo]benzene; zinc(II) oxide In 1,4-dioxane at 100℃; for 5h; Schlenk technique;	79%

C14H14N3O4S(1+)*Cl(1-) + 1-acetoacetylamino-4-chloro-2,5-dimethoxy-benzene (4433-79-8) → Pigment Yellow 97

Conditions	Yield
With sodium acetate In water pH=4.5 - 6.5;

4-sulfonatophenyldiazonium salt + 1-acetoacetylamino-4-chloro-2,5-dimethoxy-benzene (4433-79-8) → C18H17ClN3O7S(1-)*Na(1+)

Conditions	Yield
With sodium hydroxide; sodium acetate at 0℃; pH=5 - 6;

sodium hydroxide (1310-73-2) + m-acetoacetoxylidide (97-36-9) + 1-acetoacetylamino-4-chloro-2,5-dimethoxy-benzene (4433-79-8) → 3,3'-dichlorobenzidine (91-94-1)

Conditions	Yield
With acetic acid In water

3,3'-dichlorobenzidine (91-94-1) + m-acetoacetoxylidide (97-36-9) + 1-acetoacetylamino-4-chloro-2,5-dimethoxy-benzene (4433-79-8) → C36H33Cl3N6O6 (124236-34-6)

Conditions	Yield
Stage #1: 3,3'-dichlorobenzidine With hydrogenchloride; sodium nitrite In water at -4 - 0℃; for 3h; Cooling with ice; Stage #2: m-acetoacetoxylidide; 1-acetoacetylamino-4-chloro-2,5-dimethoxy-benzene With hydrogenchloride; 1-octadecylguanidinium; acetic acid; 1-aminooctadecane; sodium hydroxide In water at 0℃; Cooling with ice; Stage #3: With sodium hydroxide In water pH=4.5;

3-(4-aminophenylimino)-1-oxo-4,5,6,7-tetrachloroisoindoline + 1-acetoacetylamino-4-chloro-2,5-dimethoxy-benzene (4433-79-8) → C26H18Cl5N5O5

Conditions	Yield
Stage #1: 3-(4-aminophenylimino)-1-oxo-4,5,6,7-tetrachloroisoindoline With hydrogenchloride In N,N-dimethyl acetamide; water at 5 - 10℃; for 1h; Stage #2: With sodium nitrate In N,N-dimethyl acetamide; water at 5 - 10℃; for 1h; Stage #3: 1-acetoacetylamino-4-chloro-2,5-dimethoxy-benzene With sodium hydroxide In N,N-dimethyl acetamide; water at 20 - 150℃; Solvent; Temperature;

Upstream product

• 674-82-8 4-methyleneoxetan-2-one 
• 6358-64-1 4-chloro-2,5-dimethoxy-aniline 
• 691-45-2 acetylketene 
• 623-58-5 sodium aceto-acetate 
• 141-97-9 ethyl acetoacetate 

Downstream Products

• 80357-52-4 1-(4-Chloro-2,5-dimethoxy-phenyl)-2,6-dimethyl-4-oxo-1,4-dihydro-pyridine-3-carboxylic acid (4-chloro-2,5-dimethoxy-phenyl)-amide 
• 124236-34-6 C₃₆H₃₃Cl₃N₆O₆ 
• 1417647-05-2 2-(4-chloro-2,5-dimethoxyphenyl)-5-methylisoxazole-3(2H)-one 
• 1419183-17-7 (2,5-dimethoxy-4-chlorophenylcarbamoyl)methyl diacetate 
• 1374773-79-1 2,2-dibromo-N-(4-chloro-2,5-dimethoxyphenyl)acetamide 
• 42276-58-4 2,2-dichloro-N-(4-chloro-2,5-dimethoxyphenyl)acetamide 
• 1353648-04-0 1-(4-chloro-2,5-dimethoxyphenylcarbamoyl)-2-oxopropyl acetate 
• 91-94-1 3,3'-dichlorobenzidine 
• 12225-18-2 Pigment Yellow 97 

Relevant articles and documents

A 4 - chloro - 2, 5 - dimethoxy acetoacetanilide preparation method (by machine translation)

The invention relates to a 4 - chloro - 2, 5 - dimethoxy acetoacetanilide preparation method, its implementation are as follows: in a reaction container adding organic solvent and 4 - chloro - 2, 5 - two-anisidine, at a temperature of 10 - 100 °C lower, instillment pair ketene, about 0.5 - 5 hours after adding, canada finishes, thermal insulation reaction 0.5 - 4 hours, the reaction is finished, cooled to 0 - 10 °C, discharging the filter press, the crystalline substance is 4 - chloro - 2, 5 - dimethoxy acetoacetanilide, the filtrate is recycled. The method of the invention the resulting product quality is good, high yield, low cost, realizes the zero discharge of waste water or micro-discharge, accord with the green production requirement of environmental protection, the operation is simple, convenient for industrialization. (by machine translation)

Preparation technology of novel naphthol AS-IRG (2,5-Dimethoxy-4-chloroacetoacetanilide)

The invention relates to a preparation technology of novel naphthol AS-IRG (2,5-Dimethoxy-4-chloroacetoacetanilide). The preparation technology is characterized in that a novel separated reaction kettle is firstly designed, a three-blade sweepback axial flow stirrer is arranged in a reaction kettle body, a material inlet is formed in the upper part of the reaction kettle body, a material outlet is formed in the lower part of the reaction kettle body, and the bottom part of the reaction kettle body is provided with a water gathering pipe and a water separating valve; reactions of esterification, hydrolysis, amidation and the like are carried out in the reaction kettle. The preparation technology disclosed by the invention is novel, green and high-yield, water which is produced in a reaction process is effectively separated, amidation reaction equilibrium is promoted to continuously move rightwards, and the product yield of the naphthol AS-IRG is greatly increased through optimizing reaction conditions.

Process for improving the application properties of disazo pigments

Process for improving the application properties of disazo pigments obtained by coupling bis-diazotized chlorine-substituted 4,4'-diaminobiphenyls with acetoacetylaminobenzenes, which includes adding sulfite ions to the pigment suspension obtained in the coupling and then heating for one half to two hours at 50° to 100° C. The process produces, above all in large scale industrial batches, a product of uniform quality and having acceptable fastness to solvents, overlacquering, migration and bleeding.