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142-45-0

Basic Information
CAS No.: 142-45-0
Name: Acetylenedicarboxylic acid
Article Data: 29
Molecular Structure:
Molecular Structure of 142-45-0 (Acetylenedicarboxylic acid)
Formula: C4H2O4
Molecular Weight: 114.057
Synonyms: Acetylenedicarboxylate;but-2-ynedioate;but-2-ynedioic acid;Butynedioic acid;Acetylenedicarboxylicacid;2-Butynedioic acid;Acetylenedicarboxylic acid;
EINECS: 205-536-0
Density: 1.699 g/cm3
Melting Point: 180-187 °C
Boiling Point: 362.4 °C at 760 mmHg
Flash Point: 187.2 °C
Solubility: soluble in water
Appearance: cream coloured to beige crystalline powder
Hazard Symbols: ToxicT,IrritantXi
Risk Codes: 25-36/37/38
Safety: 26-45-37/39
Transport Information: UN 2811 6.1/PG 3
PSA: 74.60000
LogP: -0.84100
Synthetic route
75-20-7

calcium carbide

142-45-0

Acetylenedicarboxylic acid

Conditions
ConditionsYield
With sodium carbonate; silver nitrate; triphenylphosphine In acetonitrile at 60℃; under 15001.5 Torr; for 20h; Temperature; Pressure; Reagent/catalyst; Solvent; Sealed tube;98%
142-45-0

Acetylenedicarboxylic acid

Conditions
ConditionsYield
With potassium hydroxide In methanol at 90℃;87%
110-65-6

1,4-dihydroxybut-2-yne

142-45-0

Acetylenedicarboxylic acid

Conditions
ConditionsYield
With sodium hydroxide; sodium hypochlorite; 4-acetylamino-2,2,6,6-tetramethyl-1-piperidinoxy In water at 5 - 10℃; pH=8.5 - 10;71%
at 20℃; for 3h; electrolysis: nickel net anode, cylindrical stainless steel cathode; electrolyte: 1M NaOH/H2O;55%
With chromium(III) oxide; sulfuric acid; acetone
With sulfuric acid bei der Oxydation an einer Blei(IV)-Anode;
593-60-2

Vinyl bromide

124-38-9

carbon dioxide

142-45-0

Acetylenedicarboxylic acid

Conditions
ConditionsYield
Stage #1: Vinyl bromide With n-butyllithium In diethyl ether at 0℃;
Stage #2: carbon dioxide In diethyl ether Further stages.;
34%
4301-15-9

ethynyldimagnesium dibromide

142-45-0

Acetylenedicarboxylic acid

109-72-8, 29786-93-4

n-butyllithium

593-60-2

Vinyl bromide

142-45-0

Acetylenedicarboxylic acid

Conditions
ConditionsYield
With diethyl ether at 0℃; und anschliessend mit festem CO2;
3917-15-5

allyl vinyl ether

1822-71-5

n-pentylsodium

142-45-0

Acetylenedicarboxylic acid

Conditions
ConditionsYield
bei der Umsetzung anschliessend mit festem Kohlendioxid;
17096-37-6

chlorofumaryl chloride

142-45-0

Acetylenedicarboxylic acid

Conditions
ConditionsYield
With potassium hydroxide; ethanol das Kaliumsalz entsteht;
584-99-6

trans-2-bromobutenedioic acid

142-45-0

Acetylenedicarboxylic acid

Conditions
ConditionsYield
With alkali
644-80-4

cis-2-bromobutenedioic acid

142-45-0

Acetylenedicarboxylic acid

Conditions
ConditionsYield
With alkali
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Chemistry

Molecule structure of Acetylenedicarboxylic acid (CAS NO.142-45-0): 

IUPAC Name: But-2-ynedioic acid 
Molecular Weight: 114.05628 g/mol
Molecular Formula: C4H2O4 
Density: 1.699 g/cm3 
Melting Point: 180-187 °C (dec.)(lit.)
Boiling Point: 362.4 °C at 760 mmHg
Flash Point: 187.2 °C
Index of Refraction: 1.56
Molar Refractivity: 21.71 cm3
Molar Volume: 67.1 cm3
Surface Tension: 101.4 dyne/cm 
Enthalpy of Vaporization: 66.82 kJ/mol 
Vapour Pressure: 3.08E-06 mmHg at 25 °C 
Storage Temp.: 2-8 °C
Water Solubility: soluble
XLogP3-AA: 0.1
H-Bond Donor: 2
H-Bond Acceptor: 4
Exact Mass: 113.995309
MonoIsotopic Mass: 113.995309
Topological Polar Surface Area: 74.6
Heavy Atom Count: 8
Canonical SMILES: C(#CC(=O)O)C(=O)O
InChI: InChI=1S/C4H2O4/c5-3(6)1-2-4(7)8/h(H,5,6)(H,7,8)
InChIKey: YTIVTFGABIZHHX-UHFFFAOYSA-N
EINECS: 205-536-0
Product Categories: Pharmaceutical Intermediates; Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts; Acetylenic Carboxylic Acids & Their Derivatives; Acetylenes

History

 Acetylenedicarboxylic acid was first described in 1877 by Polish chemist Ernest Bandrowski.

Uses

 Both Acetylenedicarboxylic acid (CAS NO.142-45-0) and the monobasic salt potassium hydrogenacetylenedicarboxylate KC4HO4 are commonly traded as laboratory chemicals. Acetylenedicarboxylic acid is an important laboratory reagent. It is also used in the synthesis of dimethyl acetylenedicarboxylate.

Production

 Acetylenedicarboxylic acid can be made by treating α,β-dibromosuccinic acid with potassium hydroxide KOH in methanol or ethanol. This reaction yields potassium bromide and potassium acetylenedicarboxylate. The salts are separated and the latter is treated with sulfuric acid.

Safety Profile

Hazard Codes: ToxicT, IrritantXi
Risk Statements: 25-36/37/38 
R25 :Toxic if swallowed. 
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 26-45-37/39 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) 
S37/39:Wear suitable gloves and eye/face protection.
RIDADR: UN 2811 6.1/PG 3
WGK Germany: 3
HazardClass: 6.1
PackingGroup: II
HS Code: 29171990

Specification

 Acetylenedicarboxylic acid (CAS NO.142-45-0) is also named as Butynedioic acid ; NSC 1903 ; NSC 631597 ; 2-Butynedioic acid ; Butynedioic acid . Acetylenedicarboxylic acid (CAS NO.142-45-0) is cream coloured to beige crystalline powder that soluble in ether.

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