Phthalide

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:87-41-2

MDL number:MFCD00005906

EINECS number:201-744-0

RTECS number:TI3520000

BRN number:114632

PubChem number:24887500

Physical property data

1. Character: needle crystal

2. Density (g/mL, 25/4℃): 1.636

3. Relative density (20℃, 4℃) : 1.1636⁹⁹

4. Melting point (ºC): 75

5. Boiling point (ºC, normal pressure): 290

6. Refractive index at room temperature (n²⁵): 1.536⁹⁹

7. Refractive index: 1.536

8. Flash point (ºC): 152

9. Specific optical rotation (º): Uncertain

10. Autoignition point or ignition temperature (ºC): Uncertain

11. Vapor pressure (kPa, 25ºC): Uncertain

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

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

14. Critical temperature (ºC): Uncertain

15. Critical pressure (KPa): Uncertain

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

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

18. Explosion lower limit (%, V/V): Uncertain

19. Solubility: Soluble in ethanol, ether and hot water, very slightly soluble in water.

Toxicological data

1. Acute toxicity

Rat abdominal LD: >500mg/kg;

Ecological data

None yet

Molecular structure data

1. Molar refractive index: 35.55

2. Molar volume (cm³/mol): 106.0

3. Isotonic specific volume (90.2K): 277.9

4. Surface tension (dyne/cm): 47.1

5. Polarizability (10^-24cm³): 14.09

Compute chemical data

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

2. Number of hydrogen bond donors: 0

3. Number of hydrogen bond acceptors: 2

4. Number of rotatable chemical bonds: 0

5. Number of tautomers: none

6. Topological molecule polar surface area 26.3

7. Number of heavy atoms: 10

8. Surface charge: 0

9. Complexity: 153

10. Number of isotope atoms: 0

11. Determine the number of atomic stereocenters: 0

12. Uncertain atomic stereocenterNumber of stereocenters: 0

13. Determined number of stereocenters of chemical bonds: 0

14. Uncertain number of stereocenters of chemical bonds: 0

15. Total Number of price key units: 1

Properties and stability

1. Exist in flue-cured tobacco leaves, burley tobacco leaves, oriental tobacco leaves, and smoke.

2. Stable in air.

Storage method

None yet

Synthesis method

1. Tobacco: BU, 14; FC, 9; FC, OR, BU, 18.

2. Preparation method:

In a reaction bottle equipped with a stirrer, reflux condenser, and thermometer, add 130 mL of water and 160 mL of concentrated sulfuric acid. Heat to 145~150℃ with stirring. Slowly add 153g (1mol) of o-cyanobenzyl chloride (2) and hydrogen chloride escapes during the reaction. After addition, react at 160°C for 2 hours. After cooling slightly, pour it into a beaker, let it cool naturally, and solid will precipitate. Filter with suction, fully soak in water to remove inorganic salts, then filter with suction, wash with water, and dry to obtain 120g of phthalide (1). Recrystallize from ethanol to obtain 83g of pure product (1), mp73~75℃, yield 71%. ^[1]

Purpose

Organic Synthesis.