ChemicalBook > CAS DataBase List > METHYL 3-AMINO-5-METHYLTHIOPHENE-2-CARBOXYLATE

METHYL 3-AMINO-5-METHYLTHIOPHENE-2-CARBOXYLATE

Product Name
METHYL 3-AMINO-5-METHYLTHIOPHENE-2-CARBOXYLATE
CAS No.
76575-71-8
Chemical Name
METHYL 3-AMINO-5-METHYLTHIOPHENE-2-CARBOXYLATE
Synonyms
Methyl 3-aMino-5-Methylthiophen-2-carboxylate;METHYL 3-AMINO-5-METHYLTHIOPHENE-2-CARBOXYLATE;Methyl 3-amino-5-methylthiophene-2-carboxylate 95+%;3-AMINO-5-METHYLTHIOPHENE-2-CARBOXYLIC ACID, MET. ESTER;5-Methyl-3-aMinothiophene-2-carboxylic acid Methyl ester;Methyl 3-amino-5-methylthiophene-2-carboxylic acid ester;3-Amino-5-methyl-2-thiophenecarboxylic acid methyl ester;3-AMINO-5-METHYL-THIOPHENE-2-CARBOXYLIC ACID METHYL ESTER;2-Thiophenecarboxylic acid, 3-amino-5-methyl-, methyl ester;Methyl 3-Amino-5-methylthiophene-2-carboxylate, CAS 76575-71-8
CBNumber
CB6290133
Molecular Formula
C7H9NO2S
Formula Weight
171.22
MOL File
76575-71-8.mol
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METHYL 3-AMINO-5-METHYLTHIOPHENE-2-CARBOXYLATE Property

Melting point:
84-85℃ (methanol )
Boiling point:
319.2±37.0 °C(Predicted)
Density 
1.264±0.06 g/cm3(Predicted)
storage temp. 
under inert gas (nitrogen or Argon) at 2–8 °C
pka
2.08±0.10(Predicted)
form 
Solid
Appearance
Light yellow to light brown Solid
Water Solubility 
Slightly soluble in water.
InChI
InChI=1S/C7H9NO2S/c1-4-3-5(8)6(11-4)7(9)10-2/h3H,8H2,1-2H3
InChIKey
FVKMOPIFLCMZMI-UHFFFAOYSA-N
SMILES
C1(C(OC)=O)SC(C)=CC=1N
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Safety

Hazard Codes 
Xi
HazardClass 
IRRITANT
HS Code 
2921490090
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P405Store locked up.

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N-Bromosuccinimide Price

TRC
Product number
M328535
Product name
Methyl3-amino-5-methylthiophene-2-carboxylate
Packaging
100mg
Price
$75
Updated
2021/12/16
TRC
Product number
M328535
Product name
Methyl3-amino-5-methylthiophene-2-carboxylate
Packaging
500mg
Price
$255
Updated
2021/12/16
TRC
Product number
M328535
Product name
Methyl3-amino-5-methylthiophene-2-carboxylate
Packaging
1g
Price
$385
Updated
2021/12/16
ChemScene
Product number
CS-D0235
Product name
Methyl3-amino-5-methylthiophene-2-carboxylate
Purity
99.38%
Packaging
1g
Price
$36
Updated
2021/12/16
Apolloscientific
Product number
OR318100
Product name
Methyl3-amino-5-methylthiophene-2-carboxylate
Purity
97%
Packaging
1g
Price
$96
Updated
2021/12/16
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METHYL 3-AMINO-5-METHYLTHIOPHENE-2-CARBOXYLATE Chemical Properties,Usage,Production

Uses

Methyl 3-amino-5-methylthiophene-2-carboxylate is employed as a intermediate for pharmaceutical and chemical research.

Synthesis

4786-20-3

2365-48-2

76575-71-8

General procedure for the synthesis of methyl 3-amino-5-methylthiophene-2-carboxylate from 2-butenenitrile and methyl mercaptoacetate: a mixture of cis- and trans-2-butenenitrile (298.00 g, 4.44 mol) was mixed with pyridine (61.49 g, 0.78 mol) and the resulting mixture was cooled to 0 °C. Chlorine gas (314.92 g, 4.44 mol) was passed at a rate of 60-65 g/h while maintaining the internal temperature at 10-13 °C. After addition, the reaction mixture was slowly warmed to room temperature and stirred overnight. The resulting oil was dissolved in dichloromethane (1.5 L) to allow the solution to pass through a silica gel column for initial purification. The filtrate was concentrated under vacuum to give the complex reaction mixture (508.61 g) as a brown oily substance. This oily substance (493.80 g) was mixed with methyl mercaptoacetate (422.77 g, 3.98 mol), and the resulting solution was slowly (1.5 h) added dropwise to a methanol (2.2 L) slurry of potassium carbonate (1651 g, 11.95 mol) at 100 °C. The final slurry was allowed to warm to room temperature and stirred at ambient temperature for 5 hours. The solid salt was filtered out and washed with methanol (2L). Combine the organic solutions and evaporate the solvent. The residue was redissolved in ethyl acetate (3L) and subjected to secondary purification via silica gel column. The silica gel column was washed with additional ethyl acetate (2L). All organic phases were combined and the solvent was evaporated under vacuum to give a brown oil (627 g). The mixture was vacuum distilled at 6 mmHg under reduced pressure. The fraction collected at 138°C was crystallized in a receiving flask (303.07 g). The target product methyl 3-amino-5-methylthiophene-2-carboxylate (179.00 g, 26%) was obtained as white crystals by recrystallization from methanol. The structure of the product was confirmed by 1H NMR (CDCl3, 400 MHz) and 13C NMR (CDCl3, 100 MHz).

References

[1] Patent: WO2007/23382, 2007, A2. Location in patent: Page/Page column 64

METHYL 3-AMINO-5-METHYLTHIOPHENE-2-CARBOXYLATE Preparation Products And Raw materials

Raw materials

Preparation Products

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METHYL 3-AMINO-5-METHYLTHIOPHENE-2-CARBOXYLATE Suppliers

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76575-71-8, METHYL 3-AMINO-5-METHYLTHIOPHENE-2-CARBOXYLATERelated Search:

METHYL 3-AMINO-5-(4-FLUOROPHENYL)THIOPHENE-2-CARBOXYLATE Methyl 3-amino-5-(4-chlorophenyl)thiophene-2-carboxylate Methyl 3-amino-5-phenylthiophene-2-carboxylate METHYL 3-AMINO-4-METHYLTHIOPHENE-2-CARBOXYLATE 5-Methyl-2-thiophenecarboxylic acid METHYL 3-AMINO-5-(TERT-BUTYL)THIOPHENE-2-CARBOXYLATE METHYL 3-AMINO-5-(4-ISOBUTYLPHENYL)THIOPHENE-2-CARBOXYLATE ETHYL 3-AMINO-5-(4-NITROPHENYL)THIOPHEN& METHYL 5-(TERT-BUTYL)-3-[(2-CHLOROACETYL)AMINO]THIOPHENE-2-CARBOXYLATE METHYL 3-AMINO-5-[4-(TERT-BUTYL)PHENYL]THIOPHENE-2-CARBOXYLATE METHYL 3-AMINO-5-METHYLTHIOPHENE-2-CARBOXYLATE 3-AMINO-5-PHENYL-THIOPHENE-2-CARBOXYLIC ACID ETHYL ESTER methyl 3-amino-4-methylthiophene-2-carboxylate hydrochloride Methyl 2-amino-5-methylthiophene-3-carboxylate ETHYL 3-AMINO-5-(4-METHOXYPHENYL)THIOPHENE-2-CARBOXYLATE METHYL 3-[(2,2-DICHLOROACETYL)AMINO]-5-(3-THIENYL)THIOPHENE-2-CARBOXYLATE METHYL 3-[(2-CHLOROACETYL)AMINO]-5-(4-CHLOROPHENYL)THIOPHENE-2-CARBOXYLATE METHYL 3-[(2-CHLOROACETYL)AMINO]-5-PHENYLTHIOPHENE-2-CARBOXYLATE

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  • Methyl 3-Amino-5-methylthiophene-2-carboxylate, CAS 76575-71-8
  • 76575-71-8