142-45-0

Basic information

• Product Name: Acetylenedicarboxylic acid
• Synonyms: ACETYLENEDICARBOXYLIC ACID FREE ACID;BUTYNEDIOIC ACID ACETYLENE DICARBOXYLIC ACID 99%;Acetylenedicarboxylic acid,98%;Acetylen-dicarbonsαure;But-2-ynedioic acid;2-Butynedioate;NSC-1903;NSC-631597
• CAS NO: 142-45-0
• Molecular Formula: C₄H₂O₄
• Molecular Weight: 114.06
• EINECS: 205-536-0
• Product Categories: Pharmaceutical Intermediates;Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts;Acetylenic Carboxylic Acids & Their Derivatives;Acetylenes
• Mol File: 142-45-0.mol
• Article Data: 6

Chemical Properties

• Melting Point: 180-187 °C (dec.)(lit.)
• Boiling Point: 133.5°C (rough estimate)
• Flash Point: 131 °C
• Appearance: White or cream to beige/Crystalline Powder or Crystals
• Density: 1.1794 (rough estimate)
• Vapor Pressure: 3.08E-06mmHg at 25°C
• Refractive Index: 1.5260 (estimate)
• Storage Temp.: 2-8°C
• PKA: pK1: 1.75; pK2: 4.40 (25°C)
• Water Solubility: soluble
• BRN: 878357
• CAS DataBase Reference: Acetylenedicarboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: Acetylenedicarboxylic acid(142-45-0)
• EPA Substance Registry System: Acetylenedicarboxylic acid(142-45-0)

Safety Data

• Hazard Codes: T,Xi
• 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
• Hazardous Substances Data: 142-45-0(Hazardous Substances Data)

Usage

Chemical Properties

cream coloured to beige crystalline powder or

Uses

Acetylenedicarboxylic acid is employed in the preparation of dimethyl acetylenedicarboxylate and potassium hydrogenacetylenedicarboxylate. It is also used as a laboratory reagent. Further, it is used as a precursor in organic synthesis and also serves as a pharmaceutical intermediate.

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.]

InChI:InChI=1/C4H2O4/c5-3(6)1-2-4(7)8/h(H,5,6)(H,7,8)/p-2

Synthetic route

calcium carbide (75-20-7) → Acetylenedicarboxylic acid (142-45-0)

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

2,3-dibromosuccinic acid (526-78-3, 608-35-5, 608-36-6, 1114-00-7) → Acetylenedicarboxylic acid (142-45-0)

Conditions	Yield
With potassium hydroxide In methanol at 90℃;	87%

1,4-dihydroxybut-2-yne (110-65-6) → Acetylenedicarboxylic acid (142-45-0)

Conditions	Yield
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;

Vinyl bromide (593-60-2) + carbon dioxide (124-38-9) → Acetylenedicarboxylic acid (142-45-0)

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

ethynyldimagnesium dibromide (4301-15-9) → Acetylenedicarboxylic acid (142-45-0)

n-butyllithium (109-72-8, 29786-93-4) + Vinyl bromide (593-60-2) → Acetylenedicarboxylic acid (142-45-0)

Conditions	Yield
With diethyl ether at 0℃; und anschliessend mit festem CO2;

allyl vinyl ether (3917-15-5) + n-pentylsodium (1822-71-5) → Acetylenedicarboxylic acid (142-45-0)

Conditions	Yield
bei der Umsetzung anschliessend mit festem Kohlendioxid;

chlorofumaryl chloride (17096-37-6) → Acetylenedicarboxylic acid (142-45-0)

Conditions	Yield
With potassium hydroxide; ethanol das Kaliumsalz entsteht;

trans-2-bromobutenedioic acid (584-99-6) → Acetylenedicarboxylic acid (142-45-0)

Conditions	Yield
With alkali

cis-2-bromobutenedioic acid (644-80-4) → Acetylenedicarboxylic acid (142-45-0)

Conditions	Yield
With alkali

sodium acetylide (1066-26-8) + methylammonium carbonate (15719-64-9, 15719-76-3, 97762-63-5) → Acetylenedicarboxylic acid (142-45-0)

Conditions	Yield
With seasand

2,2-Dibromo-succinic acid (101349-74-0) → Acetylenedicarboxylic acid (142-45-0)

Conditions	Yield
With barium dihydroxide
With sodium hydroxide
With calcium hydroxide

n-pentylsodium (1822-71-5) + methylammonium carbonate (15719-64-9, 15719-76-3, 97762-63-5) + ethyl vinyl ether (109-92-2) → Acetylenedicarboxylic acid (142-45-0) + α-Ethoxyacrylic acid (32821-76-4)

meso-2,3-dibromosuccinic acid → Acetylenedicarboxylic acid (142-45-0)

Conditions	Yield
With potassium hydroxide In ethanol for 2h; Dehydrobromination; Heating;

methylammonium carbonate (15719-64-9, 15719-76-3, 97762-63-5) + acetylene dimagnesium bromide → Acetylenedicarboxylic acid (142-45-0)

methylammonium carbonate (15719-64-9, 15719-76-3, 97762-63-5) + disodium acetylenide → Acetylenedicarboxylic acid (142-45-0)

Conditions	Yield
With seasand

iso-α.α'-dibromo-succinic acid → Acetylenedicarboxylic acid (142-45-0)

Conditions	Yield
With sodium hydroxide
With calcium hydroxide
With barium dihydroxide

racem.-2,3-dibromo-succinic acid-anhydride → Acetylenedicarboxylic acid (142-45-0)

Conditions	Yield
With potassium hydroxide

ethynyldimagnesium dibromide (4301-15-9) + carbon dioxide (124-38-9) → Acetylenedicarboxylic acid (142-45-0)

n-butyllithium (109-72-8, 29786-93-4) + Vinyl bromide (593-60-2) + diethyl ether (60-29-7) + carbon dioxide (124-38-9) → Acetylenedicarboxylic acid (142-45-0)

Conditions	Yield
at 0℃;

1,4-dihydroxybut-2-yne (110-65-6) + acetone (67-64-1) + Cr2O3-H2SO4 → Acetylenedicarboxylic acid (142-45-0)

n-butyllithium (109-72-8, 29786-93-4) + Vinyl bromide (593-60-2) + carbon dioxide (124-38-9) + petroleum ether → Propiolic acid (471-25-0) + Acetylenedicarboxylic acid (142-45-0)

Conditions	Yield
at 14℃;

meso-2,3-difluorosuccinic acid (392-46-1) + water (7732-18-5) → Acetylenedicarboxylic acid (142-45-0)

meso-2,3-dibromosuccinic acid (608-36-6) + furan-2,3,5(4H)-trione pyridine (1:1) → hydrogen bromide (10035-10-6, 12258-64-9) + Acetylenedicarboxylic acid (142-45-0)

(+-)-2,3-dibromosuccinic acid (1114-00-7) + furan-2,3,5(4H)-trione pyridine (1:1) → hydrogen bromide (10035-10-6, 12258-64-9) + Acetylenedicarboxylic acid (142-45-0)

meso-2,3-dibromosuccinic acid (608-36-6) + barytes → hydrogen bromide (10035-10-6, 12258-64-9) + Acetylenedicarboxylic acid (142-45-0)

meso-2,3-dibromosuccinic acid (608-36-6) + KOH-solution → hydrogen bromide (10035-10-6, 12258-64-9) + Acetylenedicarboxylic acid (142-45-0)

(+-)-2,3-dibromosuccinic acid (1114-00-7) + KOH-solution → hydrogen bromide (10035-10-6, 12258-64-9) + Acetylenedicarboxylic acid (142-45-0)

meso-2,3-dibromosuccinic acid (608-36-6) + lime/chalk/ → hydrogen bromide (10035-10-6, 12258-64-9) + Acetylenedicarboxylic acid (142-45-0)

cyclopenta-1,3-diene (542-92-7) + Acetylenedicarboxylic acid (142-45-0) → bicyclo[2.2.1]hepta-2,5-diene-2,3-dicarboxylic acid (15872-28-3)

Conditions	Yield
In 1,4-dioxane at 20℃; for 12h; Diels-Alder cycloaddition;	100%
In diethyl ether Ambient temperature;	85%
Stage #1: Acetylenedicarboxylic acid With (2-bromophenyl)boronic acid In dichloromethane at 25℃; for 0.166667h; Inert atmosphere; Stage #2: cyclopenta-1,3-diene In dichloromethane at 25℃; for 48h; Diels-Alder cycloaddition; Inert atmosphere;	84%

8-azido-1,1,1,2,2,3,3,4,4,5,5,6,6-tridecafluorooctane (62571-55-5) + Acetylenedicarboxylic acid (142-45-0) → 1-(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluoro-octyl)-1H-[1,2,3]triazole-4,5-dicarboxylic acid

Conditions	Yield
In acetone for 6h; Heating;	100%

6-azido-1,1,1,2,2,3,3,4,4-nonafluorohexane (121177-78-4) + Acetylenedicarboxylic acid (142-45-0) → 1-(3,3,4,4,5,5,6,6,6-nonafluoro-hexyl)-1H-[1,2,3]triazole-4,5-dicarboxylic acid

Conditions	Yield
In acetone for 6h; Heating;	100%

1-azido-1H,1H,2H,2H-perfluorodecane (121177-79-5) + Acetylenedicarboxylic acid (142-45-0) → 1-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluoro-decyl)-1H-[1,2,3]triazole-4,5-dicarboxylic acid

Conditions	Yield
In acetone for 6h; Heating;	100%

Acetylenedicarboxylic acid (142-45-0) → <2H6>γ-Butyrolactone (77568-65-1)

Conditions	Yield
With deuterium; Ru4H4(CO)8(PBu3)4 In tetrahydrofuran at 180℃; for 48h;	100%

tert-butyl 3-(2-(2-(2-aminoethoxyl)ethoxy)ethoxy)propanoate (252881-74-6) + Acetylenedicarboxylic acid (142-45-0) → di-tert-butyl 14,17-dioxo-4,7,10,21,24,27-hexaoxa-13,18-diazatriacont-15-yne-1,30-dioate

Conditions	Yield
With 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride In 1-methyl-pyrrolidin-2-one at 0℃; for 6h;	100%
With 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride In 1-methyl-pyrrolidin-2-one at 0℃; for 6h;
With 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride In 1-methyl-pyrrolidin-2-one at 0℃; for 6h;	2.26 g

N,N-Dimethylselenourea (5117-16-8) + Acetylenedicarboxylic acid (142-45-0) → (Z)-5-(carboxymethylene)-2-(dimethylamino)-4,5-dihydro-1,3-selenazol-4-one

Conditions	Yield
In ethanol at 20℃; for 1h;	99%

Phenyl triflate (17763-67-6) + Acetylenedicarboxylic acid (142-45-0) → diphenyl acetylene (501-65-5)

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; 1,4-di(diphenylphosphino)-butane In dimethyl sulfoxide at 110℃; for 3h;	98%

N-(selenocarbamido)piperidine (61934-60-9) + Acetylenedicarboxylic acid (142-45-0) → Z-5-carboxylmethylene-2-piperidino-4,5-dihydro-1,3-selenazol-4-one

Conditions	Yield
In ethanol at 20℃; for 1h;	97%

(S)-2-Octanol (6169-06-8) + Acetylenedicarboxylic acid (142-45-0) → bis[(1S)-1-methylheptyl] acetylenedicarboxylate (1181217-27-5)

Conditions	Yield
With sulfuric acid In tetrahydrofuran for 14h; Reflux;	97%

bromobenzene (108-86-1) + Acetylenedicarboxylic acid (142-45-0) → diphenyl acetylene (501-65-5)

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; 1,4-di(diphenylphosphino)-butane In dimethyl sulfoxide at 110℃; for 3h;	97%

N,N-diethylselenourea (5117-17-9) + Acetylenedicarboxylic acid (142-45-0) → Z-5-carboxylmethylene-2-diethylamino-4,5-dihydro-1,3-selenazol-4-one

Conditions	Yield
In ethanol at 20℃; for 1h;	96%

Acetylenedicarboxylic acid (142-45-0) → acetylene dicarboxylic acid disodium salt

Conditions	Yield
With sodium hydroxide In methanol at 20℃; for 2h;	96%
With sodium hydroxide In methanol; water

Upstream product

• 110-65-6 1,4-dihydroxybut-2-yne 
• 4301-15-9 ethynyldimagnesium dibromide 
• 3917-15-5 allyl vinyl ether 
• 1822-71-5 n-pentylsodium 
• 17096-37-6 chlorofumaryl chloride 
• 584-99-6 trans-2-bromobutenedioic acid 
• 644-80-4 cis-2-bromobutenedioic acid 
• 1066-26-8 sodium acetylide 
• 15719-64-9 methylammonium carbonate 
• 101349-74-0 2,2-Dibromo-succinic acid 
• 109-92-2 ethyl vinyl ether 
• 124-38-9 carbon dioxide 
• 109-72-8 n-butyllithium 
• 593-60-2 Vinyl bromide 

Downstream Products

• 610-13-9 cyclohexa-1,4-diene-1,2-dicarboxylic acid 
• 95466-59-4 3-phenyl-isoxazole-4,5-dicarboxylic acid 
• 92498-00-5 (1-benzyl-pyrrol-2-yl)-maleic acid anhydride 
• 34354-00-2 7-benzyl-7-aza-bicyclo[2.2.1]hepta-2,5-diene-2,3-dicarboxylic acid 
• 97976-18-6 (1-benzyl-pyrrol-2-yl)-fumaric acid 
• 15872-28-3 bicyclo[2.2.1]hepta-2,5-diene-2,3-dicarboxylic acid 
• 49597-17-3 5-oxo-1-phenyl-2,5-dihydro-1H-pyrazole-3-carboxylic acid 
• 17660-55-8 rac-2,3-bis(acetylthio)succinic acid 
• 4315-35-9 cyclohexa-1,4-diene-1-carboxylic acid 
• 4994-16-5 4-phenylcyclohexene 
• 3642-06-6 Bicyclo<4.4.0>deca-3,8-dien-1,6-dicarbonsaeureanhydrid 
• 91061-82-4 4,5-dimethylcyclohexa-1,4-diene-1,2-dicarboxylic acid 
• 14447-07-5 diprop-2-enyl acetylenedicarboxylate 
• 39489-87-7 p-tolylsulfanyl-fumaric acid 

Related news

Z-scan measurements of single walled carbon nanotube doped Acetylenedicarboxylic acid (cas 142-45-0) polymer under CW laser09/29/2019

Z-scan measurements of single walled carbon nanotube (SWCNT) doped with acetylenedicarboxylic acid (ADC) polymer are performed using a CW diode laser at 635nm wavelength with 17mW power. The nonlinear absorption coefficient (β), nonlinear refractive index (n2), the real and imaginary parts of t...detailed

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