o-Methoxyacetoacetanilide

Structural formula

• Numbering system
• Physical property data
• Toxicological data
• Ecological data
• Molecular structure data
• Computing chemical data
• More
  • Properties and Stability
  • Storage method
  • Synthesis method
  • Purpose

Numbering system

CAS number:92-15-9

MDL number:MFCD00008781

EINECS number:202-131-0

RTECS number:BZ5600000

BRN number:None

PubChem number:24891363

Physical property data

1. Properties: White powdery crystal.

2. Density (g/mL, 25/4℃): 1.1320

3. Relative vapor density (g/mL, air =1): Undetermined

4. Melting point (ºC): 86.6

5. Boiling point (ºC, normal pressure): Undetermined

6. Boiling point (ºC, 5.2kPa): Undetermined

7. Refractive index: Undetermined

8. Flash point (ºC): 163

9. Specific rotation (º): Undetermined

10 . Autoignition point or ignition temperature (ºC): Not determined

11. Vapor pressure (kPa, 25ºC): Not determined

12 . Saturated vapor pressure (kPa, 60ºC): Undetermined

13. Heat of combustion (KJ/mol): Undetermined

14. Critical temperature (ºC): Undetermined

15. Critical pressure (KPa): Undetermined

16. Oil and water (octanol/water ) Log value of distribution coefficient: Undetermined

17. Explosion upper limit (%, V/V): Undetermined

18. Explosion Lower limit (%, V/V): Undetermined

19. Solubility: Soluble in ethanol, chloroform and benzene, slightly soluble in ether.

Toxicological data

None yet

Ecological data

None yet

Molecular structure data

1. Molar refractive index: 56.49

2. Molar volume (cm³/mol): 176.6

3. Isotonic specific volume (90.2K ): 452.3

4. Surface tension� (dyne/cm): 42.9

5. Polarizability (10^-24cm³): 22.39

Compute chemical data

1. Reference value for hydrophobic parameter calculation (XlogP): None

2. Number of hydrogen bond donors: 1

3. Number of hydrogen bond acceptors: 3

4. Number of rotatable chemical bonds: 4

5. Number of tautomers: 8

6. Topological molecule polar surface area 55.4

7. Number of heavy atoms: 15

8. Surface charge: 0

9. Complexity: 240

10. Number of isotope atoms: 0

11. Determine the number of atomic stereocenters: 0

12. Uncertain number of atomic stereocenters: 0

13. Determine the number of chemical bond stereocenters: 0

14. Number of uncertain chemical bond stereocenters: 0

15. Number of covalent bond units: 1

Properties and stability

Storage method

Stored in sealed and exposed light.

Packed in plastic-coated fiberglass bags, 30kg per bag. Place in a dry, ventilated place, away from sunlight. Handle with care when transporting. Protect from moisture and heat. Store and transport according to flammable and drug regulations.

Synthesis method

The following two process routes can be used. (1) Obtained from the reaction between ethyl acetoacetate and o-methoxyaniline. First, heat the ethanol solution of dry xylene, ethyl acetoacetate and triethanolamine to a slight boil, steam out part of the xylene solution (temperature is between 118-120°C), slowly heat it to 137-140°C, and collect the Cool the mixture of toluene and ethanol to 5-7°C, filter and crystallize, wash with a little xylene to obtain crude product, and then recrystallize with ethanol. (2) Reaction of o-methoxyaniline and diketene: add 500 parts of water to the reaction kettle. Add 0.02 part of triphenylphosphine and 0.1 part of N,N-dimethylaniline under vigorous stirring. Within 45 minutes, 90 parts of diketene (95.6% purity) and 1123 parts of o-methoxyaniline were added through two lines (inserted into the solution) under stirring (both were added at equimolar speeds). Cool sufficiently to keep the reaction temperature at 20°C. After the addition reaction is completed, stir for another 1 hour to obtain a slurry product. Cool it to 10°C, filter and dry to obtain 192 parts of white o-methoxyacetoacetanilide, with a yield of 93% and a purity of 99.5%. In industrial production, o-methoxyaniline and diketene can also be condensed in ethanol medium at 20-25°C.

Purpose

1. Azo dye intermediates. Organic Synthesis.