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Methyl 4,5-dichlorothiophene-2-carboxylate

Product Name
Methyl 4,5-dichlorothiophene-2-carboxylate
CAS No.
89281-29-8
Chemical Name
Methyl 4,5-dichlorothiophene-2-carboxylate
Synonyms
Rivaroxaban Impurity 155;Methyl 4,5-dichlorothiophene-2-carboxylate;Methyl 4,5-dichloro-2-thiophenecarboxylate;2,3-dichlorothiophene-5-carboxylic acid methyl ester;4,5-Dichloro-2-thiophenecarboxylic acid methyl ester;2-Thiophenecarboxylic acid, 4,5-dichloro-, methyl ester;Methyl 4,5-dichlorothiophene-2-carboxylate (Rivaroxaban Impurity)
CBNumber
CB92666380
Molecular Formula
C6H4Cl2O2S
Formula Weight
211.07
MOL File
89281-29-8.mol
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Methyl 4,5-dichlorothiophene-2-carboxylate Property

Boiling point:
281.3±35.0 °C(Predicted)
Density 
1.500±0.06 g/cm3(Predicted)
storage temp. 
under inert gas (nitrogen or Argon) at 2–8 °C
Appearance
Yellow to brown Solid
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Hazard and Precautionary Statements (GHS)

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N-Bromosuccinimide Price

AK Scientific
Product number
4736AC
Product name
Methyl4,5-dichlorothiophene-2-carboxylate
Packaging
100mg
Price
$95
Updated
2021/12/16
AK Scientific
Product number
4736AC
Product name
Methyl4,5-dichlorothiophene-2-carboxylate
Packaging
1g
Price
$253
Updated
2021/12/16
American Custom Chemicals Corporation
Product number
HCH0369367
Product name
METHYL-4,5-DICHLOROTHIOPHENE-2-CARBOXYLATE
Purity
95.00%
Packaging
5MG
Price
$499.33
Updated
2021/12/16
AK Scientific
Product number
4736AC
Product name
Methyl4,5-dichlorothiophene-2-carboxylate
Packaging
10g
Price
$1400
Updated
2021/12/16
Arctom
Product number
AS013567
Product name
Methyl4,5-dichlorothiophene-2-carboxylate
Purity
≥95%
Packaging
100mg
Price
$33
Updated
2021/12/16
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Methyl 4,5-dichlorothiophene-2-carboxylate Chemical Properties,Usage,Production

Uses

Methyl 4,5-dichlorothiophene-2-carboxylate is used as a reactant in the preparation of 2-aryl indole neurokinin NK receptor antagonists in relation to optimization of amide substituent.

Synthesis

5380-42-7

89281-29-8

The general procedure for the synthesis of methyl 4,5-dichlorothiophene-2-carboxylate from methyl thiophene-2-carboxylate was as follows: methyl thiophene-2-carboxylate (3,142.2 g, 1 mol) was added to a mixed solution of trifluoroacetic acid (TFA, 720 mL) and concentrated sulfuric acid (H2SO4, 180 mL). After cooling the reaction mixture to 0°C, N-chlorosuccinimide (NCS, 333.8 g, 2.5 mol) was added in batches. After addition, the reaction mixture was continued to be stirred for 10 minutes. Subsequently, the reaction solution was quenched by pouring it into cold water. The precipitated solid was collected by filtration, washed with water and dried under vacuum to afford methyl 4,5-dichlorothiophene-2-carboxylate (190 g, 90% yield) as a light yellow solid with a melting point of 58-59°C (literature value 55-56°C). The product was confirmed by infrared spectroscopy (KBr) showing the carbonyl absorption peak located at 1702 cm-1. Nuclear magnetic resonance hydrogen spectrum (1H NMR, CDCl3) showed: δ 7.56 (s, 1H, H-3), 3.89 (s, 3H, -OCH3). Nuclear magnetic resonance carbon spectra (13C NMR, CDCl3) showed: δ 160.8, 132.5, 131.7, 129.6, 125.1, 52.6. Elemental analysis results (C6H4Cl2O2S) Calculated values: C, 34.14; H, 1.91; Measured values: C, 34.01; H, 2.08%. Mass spectrometry (ESI) showed a molecular ion peak m/z 212.1 [M + H]+.

References

[1] Journal of Chemical Research, 2014, vol. 38, # 10, p. 622 - 624

Methyl 4,5-dichlorothiophene-2-carboxylate Preparation Products And Raw materials

Raw materials

Preparation Products

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Methyl 4,5-dichlorothiophene-2-carboxylate Suppliers

China 37 India 1 United States 1 Global 39
Adamas Reagent, Ltd.
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89281-29-8, Methyl 4,5-dichlorothiophene-2-carboxylateRelated Search:

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  • Methyl 4,5-dichlorothiophene-2-carboxylate
  • 4,5-Dichloro-2-thiophenecarboxylic acid methyl ester
  • 2,3-dichlorothiophene-5-carboxylic acid methyl ester
  • 2-Thiophenecarboxylic acid, 4,5-dichloro-, methyl ester
  • Rivaroxaban Impurity 155
  • Methyl 4,5-dichlorothiophene-2-carboxylate (Rivaroxaban Impurity)
  • Methyl 4,5-dichloro-2-thiophenecarboxylate
  • 89281-29-8