Acetylenedicarboxylic acid

Details:

Melting point     180-187 °C (dec.) (lit.)
Boiling point     133.5°C (rough estimate)
density     1.1794 (rough estimate)
refractive index     1.5260 (estimate)
Fp     131 °C
storage temp.     2-8°C
pka    pK1: 1.75; pK2: 4.40 (25°C)
form     Crystalline Powder or Crystals
color     White or cream to beige
Water Solubility     soluble
BRN     878357
InChIKey    YTIVTFGABIZHHX-UHFFFAOYSA-N
CAS DataBase Reference    142-45-0(CAS DataBase Reference)
NIST Chemistry Reference    2-Butynedioic acid(142-45-0)
EPA Substance Registry System    2-Butynedioic acid (142-45-0)
Safety Information
Hazard Codes     T,Xi
Risk Statements     25-36/37/38
Safety Statements     26-45-37/39
RIDADR     UN 2811 6.1/PG 3
WGK Germany     3
TSCA     Yes
HazardClass     6.1
PackingGroup     II
HS Code     29171990
MSDS Information
Provider    Language
Acetylenedicarboxylic acid    English
SigmaAldrich    English
ACROS    English
ALFA    English
Acetylenedicarboxylic acid Usage And Synthesis
Chemical Properties    cream coloured to beige crystalline powder or
Definition    ChEBI: An acetylenic compound that is acetylene in which the hydrogens are replaced by carboxy groups.
Purification Methods    The acid is soluble in Et2O and crystallises from Et2O/pet ether (m 183-183.5o), or H2O as the dihydrate which dehydrates in a desiccator over conc H2SO4 in a vacuum. The dipicrate crystallises from aqueous ether. For the mono K salt see entry in “Metal-organic Compounds”, Chapter 5. [Abbott et al. Org Synth Coll Vol II 10 1943, Huntress et al. Org Synth Coll Vol IV 329 1963, Beilstein 2 H 801, 2 I 317, 2 II 670, 2 III 1991, 2 IV 2290.]
Acetylenedicarboxylic acid Preparation Products And Raw materials
Raw materials    meso-2,3-Dibromosuccinic acid-->(Z)-Bromofumaric acid-->cis-2-chloro-2-butenedioyl dichloride-->acetylene-bis-magnesium bromide, Fandachem-->Butanedioic acid, 2,2-dibromo--->bromomaleic acid-->2-Butyne-1,4-diol-->Vinyl bromide-->CARBON DIOXIDE-->SODIUM ACETYLIDE-->Calcium carbide
Preparation Products    Dimercaptosuccinic acid-->Acetaldehyde-->4,4'-DIFLUORODIPHENYLACETYLENE-->DI-P-TOLYLACETYLENE-->DI-TERT-BUTYL ACETYLENEDICARBOXYLATE