ChemicalBook > CAS DataBase List > Methyl 4,5-dichlorothiophene-2-carboxylate

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

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: 1g
Price: $253
Updated: 2021/12/16

AK Scientific

Product number: 4736AC
Product name: Methyl4,5-dichlorothiophene-2-carboxylate
Packaging: 10g
Price: $1400
Updated: 2021/12/16

Chemenu

Product number: CM199246
Product name: Methyl4,5-dichlorothiophene-2-carboxylate
Purity: 95%
Packaging: 25g
Price: $1851
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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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