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2-Thiopheneglyoxylic acid

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2-Thiopheneglyoxylic acid Basic information

Product Name:
2-Thiopheneglyoxylic acid
Synonyms:
  • Oxo(thien-2-yl)acetic acid 96%
  • 2-oxo-2-thiophen-2-ylacetate
  • ALPHA-OXO-2-THIOPHENEACETIC ACID
  • 2-THIENYLGLYOXYLIC ACID
  • 2-THIOPHENEGLYOXYLIC ACID
  • 2-OXO-2-(2-THIENYL)ACETIC ACID
  • alpha-oxothiophen-2-acetic acid
  • α-oxo-2-thiopheneacetic acid
CAS:
4075-59-6
MF:
C6H4O3S
MW:
156.16
EINECS:
223-794-2
Product Categories:
  • Building Blocks
  • C4 to C6
  • Chemical Synthesis
  • Heterocyclic Building Blocks
  • Thiophenes
  • Sulphur Derivatives
  • Thiophene&Benzothiophene
  • Organic acids
  • Heterocyclic Compounds
Mol File:
4075-59-6.mol
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2-Thiopheneglyoxylic acid Chemical Properties

Melting point:
88-91 °C (lit.)
Boiling point:
250.38°C (rough estimate)
Density 
1.404 (estimate)
refractive index 
1.5151 (estimate)
storage temp. 
under inert gas (nitrogen or Argon) at 2–8 °C
form 
solid
pka
2.09±0.54(Predicted)
Sensitive 
Hygroscopic
BRN 
115791
CAS DataBase Reference
4075-59-6(CAS DataBase Reference)
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Safety Information

Hazard Codes 
C,Xi
Risk Statements 
34
Safety Statements 
26-27-28-36/37/39-45
RIDADR 
UN 3261 8/PG 2
WGK Germany 
3
Hazard Note 
Irritant
HazardClass 
8
PackingGroup 
III
HS Code 
29349990

MSDS

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2-Thiopheneglyoxylic acid Usage And Synthesis

Chemical Properties

white to light yellow crystal powder

Uses

2-Thiopheneglyoxylic acid was used in the synthesis of europium complexes.

Synthesis

4075-58-5

4075-59-6

The general procedure for the synthesis of 2-thiophene glyoxalate from ethyl thiophene-2-glyoxalate was as follows: to a solution of ethyl thiophene-2-glyoxalate (4 mL, 27.17 mmol) in ethanol (60 mL) was added an aqueous 4N sodium hydroxide solution (10.2 mL, 40.76 mmol). The reaction mixture was stirred at room temperature for 18 hours. Upon completion of the reaction, the reaction solution was acidified with 2N aqueous hydrochloric acid to pH 2. Subsequently, the solvent was removed by vacuum distillation to afford 2-thiophene glyoxalic acid as a yellow solid product (quantitative yield). The resulting residue was used directly in the subsequent reaction without further purification.LCMS analysis (Method 2): [MH-] = 155 with a retention time of 0.71 min.

References

[1] Patent: WO2016/193244, 2016, A1. Location in patent: Page/Page column 80
[2] Chemical Communications, 2014, vol. 50, # 34, p. 4489 - 4491
[3] Patent: WO2016/177849, 2016, A1. Location in patent: Page/Page column 60
[4] Advanced Synthesis and Catalysis, 2018, vol. 360, # 21, p. 4184 - 4190

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