butynedioic acid

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:142-45-0

MDL number:MFCD00004362

EINECS number:205-536-0

RTECS number:None

BRN number:878357

PubChem number:24886837

Physical property data

None yet

Toxicological data

None yet

Ecological data

None yet

Molecular structure data

1. Molar refractive index: 21.71

2. Molar volume (cm³/mol): 67.1

3. Isotonic specific volume (90.2K ): 213.0

4. Surface tension (dyne/cm): 101.4

5. Polarizability (10^-24cm³): 8.60

Compute chemical data

1. Reference value for hydrophobic parameter calculation (XlogP): 0.1

2. Number of hydrogen bond donors: 2

3. Number of hydrogen bond acceptors: 4

4. Number of rotatable chemical bonds: 0

5. Number of tautomers: none

6. Topological molecule polar surface area 74.6

7. Number of heavy atoms: 8

8. Surface charge: 0

9. Complexity: 161

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

None

Synthesis method

1. Using α,β-dibromosuccinic acid as raw material, remove HBr in an alkaline solution to obtain sodium butyndioic acid. Preparation process of sodium butyndioic acid: Prepare sodium hydroxide solution, cool it, and add α,β-dibromosuccinic acid one by one. After the addition is completed, raise the temperature to 40°C and keep warm for 3 hours. Cool the crystallization to below 10°C, filter, and dry the crystal to obtain sodium butynioate. The yield is 75-87%.

2. Preparation method:

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Into a 2L reaction bottle equipped with a stirrer and reflux condenser, add 122g (2.2mol) of potassium hydroxide and 700mL of 95% methanol, and stir to dissolve. Slowly add 100g (0.36mol) of a,β-dibromosuccinic acid (2)^①, and heat to reflux for 1.5h. After cooling and suction filtration, the filter cake is fully washed with methanol and dried to obtain 144-150g of mixed salt. Dissolve the mixed salt in 270 mL of water, add dilute acid composed of 30 mL of water and 8 mL of concentrated sulfuric acid, and the monopotassium salt of butynodiic acid precipitates, and leave it overnight. Filter with suction, dissolve the acid salt in dilute acid made of 60 mL concentrated sulfuric acid and 240 mL water, and extract with ether (100 mL × 5). Combine the ether extracts and evaporate the ether to obtain butynedioic acid hydrate. Vacuum dry in a desiccator filled with concentrated sulfuric acid to obtain 30-36g of butynedioic acid (1), yield 73%-88%, mp 175-177.�. Note: ① The reaction is exothermic and cannot be added at once. ^[1]

Purpose

Pharmaceutical intermediates, used in the production of antidote sodium dimercaptosuccinate.