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A15207

Acetylenedicarboxylic acid

Name: Acetylenedicarboxylic acid
Brand: ALDRICH

95%

Synonym(s):

2-Butynedioic acid

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About This Item

Linear Formula:

HOOCC≡CCOOH

CAS Number:

142-45-0

Molecular Weight:

114.06

UNSPSC Code:

12352100

NACRES:

NA.22

PubChem Substance ID:

24890553

EC Number:

205-536-0

Beilstein/REAXYS Number:

878357

MDL number:

MFCD00004362

Assay:

95%

Form:

crystals

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Properties

Quality Level

200

assay

95%

form

crystals

mp

180-187 °C (dec.) (lit.)

storage temp.

2-8°C

SMILES string

OC(=O)C#CC(O)=O

InChI

1S/C4H2O4/c5-3(6)1-2-4(7)8/h(H,5,6)(H,7,8)

InChI key

YTIVTFGABIZHHX-UHFFFAOYSA-N

Description

Application

Acetylenedicarboxylic acid is generally used to synthesize its ester derivatives, dimethyl acetylenedicarboxylate (DMAD) and dimethyl acetylenedicarboxylate, which are useful precursors in organic synthesis.
Some of the common applications are listed below:

Acetylenedicarboxylic acid and its ester derivatives can undergo Cu(I)-catalyzed radical addition with acetophenones to yield furan derivatives.
It is one of the shortest linear links used in the preparation of Covalent Organic Frameworks (COFs) and Metal Organic Frameworks (MOFs) like IRMOF-0.
Various hexaarylbenzenes can be built via oxidative cyclodehydrogenation of diaryl alkynes derived from acetylenedicarboxylic acid.
It can be used as a spacer while synthesizing molecular chains or dendrimers such as 2,3,8-trifunctionalized indenoquinoxaline dendrons and bisarylacetylene chromophores.

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pictograms

GHS06

signalword

Danger

hcodes

H301,H315,H319,H335

pcodes

P261 - P264 - P271 - P301 + P310 - P302 + P352 - P305 + P351 + P338

Hazard Classifications

Acute Tox. 3 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk

WGK 3

flash_point_f

267.8 °F

flash_point_c

131 °C

ppe

Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges

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Two-and three-photon absorption properties of fan-shaped dendrons derived from 2, 3, 8-trifunctionalized indenoquinoxaline units: synthesis and characterization.

Lin TC, et al.

Journal of Material Chemistry C, 5(32), 8219-8232 (2017)

Synthesis and multi-photon absorption properties of symmetric bisarylacetylene chromophores using functionalized isomeric pyrazinoindenocarbazole units as the rigid aryl substituents.