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

Chemical Properties

Off-white powder

Uses

4'-Chloro-2',5'-dimethoxyacetoacetanilide is used as intermediate for the manufacture of organic pigments.

Preparation

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

Properties and Applications

white powder. Mainly used for cotton fabric and glue the cotton fabric dyeing and printing, general is not used for cotton yarn dyeing. The affinity of cotton is low, is not suitable for contaminated. This product is suitable for the fastness to demand higher cotton products, and can be used as organic pigments intermediate.

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

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

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

Relevant articles and documents

Preparation method of 4-Chloro-2,5-dimethoxyacetoace tanilide

The invention discloses a preparation method of 4-Chloro-2,5-dimethoxyacetoace tanilide. The preparation method particularly comprises the following steps: adding an alcohols solvent or an acetic acid solvent into a reactor, meanwhile, adding 2,5-dimethoxy-4-chloroaniline, controlling the temperature to be 10-100 DEG C, dripping acetyl ketene, and finishing adding after 0.5-4 h, wherein the molar ratio of 2,5-dimethoxy-4-chloroaniline to acetyl ketene is 1:1-1:1.2; and after finish of dripping, preserving the temperature for 0.5-4 h, keeping the material in a fully-dissolved state after finish of reaction, adjusting the pH to be 0.5-5.0, quickly cooling with a refrigerating fluid, quickly stirring, controlling the cooling speed to be 5-40 DEG C/min, enabling 4-Chloro-2,5-dimethoxyacetoace tanilide to be quickly separated out as powder, cooling to -10 DEG C to 20 DEG C, filtering and drying obtain 4-Chloro-2,5-dimethoxyacetoace tanilide. The preparation method is simple, and the enolic isomer content in obtained 4-Chloro-2,5-dimethoxyacetoace tanilide can be controlled to be 50 ppm or below.

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.