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4-AMINO-THIOPHENE-2-CARBOXYLIC ACID METHYL ESTER

Product Name
4-AMINO-THIOPHENE-2-CARBOXYLIC ACID METHYL ESTER
CAS No.
89499-43-4
Chemical Name
4-AMINO-THIOPHENE-2-CARBOXYLIC ACID METHYL ESTER
Synonyms
METHYL 4-AMINOTHIOPHENE-2-CARBOXYLATE;Methyl 4-amino-2-thiophenecarboxylate;methyl 4-aminothiophene-2;4-AMINO-THIOPHENE-2-CARBOXYLIC ACID METHYL ESTER;2-Thiophenecarboxylicacid, 4-aMino-, Methyl ester;methyl 4-aminothiophene-2-carboxylate hydrochloride;2-Thiophenecarboxylic acid, 4-amino-, methyl ester, hydrochloride
CBNumber
CB7193394
Molecular Formula
C6H7NO2S
Formula Weight
157.19
MOL File
89499-43-4.mol
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4-AMINO-THIOPHENE-2-CARBOXYLIC ACID METHYL ESTER Property

Melting point:
82-84℃
Boiling point:
318.9±22.0 °C(Predicted)
Density 
1.319±0.06 g/cm3 (20 ºC 760 Torr)
storage temp. 
2-8°C(protect from light)
pka
3.11±0.10(Predicted)
Appearance
White to light yellow Solid
InChI
InChI=1S/C6H7NO2S/c1-9-6(8)5-2-4(7)3-10-5/h2-3H,7H2,1H3
InChIKey
HCRQNZWIOUMCOW-UHFFFAOYSA-N
SMILES
C1(C(OC)=O)SC=C(N)C=1
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H302Harmful if swallowed

H312Harmful in contact with skin

H315Causes skin irritation

H319Causes serious eye irritation

H332Harmful if inhaled

H335May cause respiratory irritation

Precautionary statements

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

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P302+P352IF ON SKIN: wash with plenty of soap and water.

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.

P312Call a POISON CENTER or doctor/physician if you feel unwell.

P321Specific treatment (see … on this label).

P322Specific measures (see …on this label).

P330Rinse mouth.

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P362Take off contaminated clothing and wash before reuse.

P363Wash contaminated clothing before reuse.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

TRC
Product number
M286645
Product name
Methyl4-Aminothiophene-2-carboxylate
Packaging
500mg
Price
$130
Updated
2021/12/16
AK Scientific
Product number
W9240
Product name
Methyl4-aminothiophene-2-carboxylate
Packaging
1g
Price
$149
Updated
2021/12/16
Matrix Scientific
Product number
074456
Product name
Methyl 4-aminothiophene-2-carboxylate
Purity
95+%
Packaging
1g
Price
$200
Updated
2021/12/16
Ark Pharm
Product number
P000562128
Product name
Methyl 4-aminothiophene-2-carboxylate
Purity
98%
Packaging
5g
Price
$258
Updated
2021/12/16
Ark Pharm
Product number
P000562128
Product name
Methyl 4-aminothiophene-2-carboxylate
Purity
98%
Packaging
250mg
Price
$29
Updated
2021/12/16
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4-AMINO-THIOPHENE-2-CARBOXYLIC ACID METHYL ESTER Chemical Properties,Usage,Production

Synthesis

67-56-1

527-72-0

14597-58-1

89499-43-4

Example 12: Synthesis of 4-[dimethylamino)diazenyl]thiophene-2-carboxamide (Compound 12);. Step a: Synthesis of 4-nitrothiophene-2-carboxylic acid: Concentrated sulfuric acid (3.0 mL, 5.505 g, 56.17 mmol) was slowly added dropwise to concentrated nitric acid (2.0 mL, 2.98 g, 49.6 mmol) at 0-10 °C in an ice bath. After the dropwise addition was completed, thiophene-2-carboxylic acid (2.8 g, 21.87 mmol) was added to the above nitrification mixture in batches over 15 minutes, maintaining the same temperature, followed by continued stirring of the reaction mixture for 1 hour. After completion of the reaction, the mixture was slowly poured into ice water and stirred for 30 minutes. The precipitated solid was filtered, washed with cold water and dried. The filtrate was extracted with ethyl acetate and the organic phases were combined, washed sequentially with water, saturated brine and dried over anhydrous sodium sulfate. After filtration, the organic phase was concentrated under reduced pressure. The resulting crude product was stirred with hexane (2 x 50 mL) and filtered to give an off-white solid product (2.8 g, 75%) with a melting point of 110-118 °C. HPLC and 1H NMR analyses showed the product to be a mixture of the two compounds, which was used directly in the next step of the reaction. Step b: Synthesis of methyl 4-nitrothiophene-2-carboxylate: Thionyl chloride (6 mL, 78.6 mmol) was added slowly and dropwise to a solution of 4-nitrothiophene-2-carboxylic acid (6.8 g, 39.3 mmol) in methanol (50 mL) with stirring at room temperature. After the dropwise addition, the reaction mixture was heated to reflux for 2 hours and subsequently cooled to room temperature. The reaction mixture was poured into ice water and stirred for 15 minutes. The precipitated solid was filtered, washed with cold water and dried to give an off-white solid product (6.2 g, 85%).1H NMR analysis showed the product to be a mixture of the two compounds and the crude product was used directly in the next step of the reaction. Step c: Synthesis of methyl 4-aminothiophene-2-carboxylate and methyl 5-aminothiophene-2-carboxylate: To a mixed solution of methyl 4-nitrothiophene-2-carboxylate (7 g, 37.43 mmol) in water (150 mL) and methanol (50 mL) was added concentrated hydrochloric acid (4.5 mL). To this solution, iron powder (10.5 g, 188 mmol) and ammonium chloride (10 g, 187 mmol) were added sequentially at room temperature. The reaction mixture was stirred and heated to 70 °C, maintained for 1 h and cooled to room temperature. The reaction mixture was filtered and the filtrate was alkalized with saturated sodium bicarbonate solution and extracted with chloroform (4 x 100 mL). The organic phases were combined, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was separated by silica gel column chromatography using hexane-ethyl acetate (90:10 with a small amount of triethylamine) as eluent to first obtain methyl 4-aminothiophene-2-carboxylate (1.8 g, 31%) with a melting point of 76-78 °C. 1H NMR (400 MHz, CDCl3): δ 7.31 (1H, d, J=1.6 Hz), 6.40 (1H, d, J= 1.6 Hz), 3.85 (3H, s), 3.63 (2H, br s). Continued elution with the same solvent system afforded methyl 5-aminothiophene-2-carboxylate (0.5 g, 8.5%) with a melting point of 70-72 °C.1H NMR (400 MHz, CDCl3): δ 7.45 (1H, d, J=4.0 Hz), 6.09 (1H, d, J=4.0 Hz), 4.29 (2H, br s), 3.81 (3H, s ).

References

[1] Patent: WO2010/29577, 2010, A2. Location in patent: Page/Page column 38-39

4-AMINO-THIOPHENE-2-CARBOXYLIC ACID METHYL ESTER Preparation Products And Raw materials

Raw materials

Preparation Products

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4-AMINO-THIOPHENE-2-CARBOXYLIC ACID METHYL ESTER Suppliers

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View Lastest Price from 4-AMINO-THIOPHENE-2-CARBOXYLIC ACID METHYL ESTER manufacturers

Career Henan Chemical Co
Product
4-AMINO-THIOPHENE-2-CARBOXYLIC ACID METHYL ESTER 89499-43-4
Price
US $1.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
10000KGS
Release date
2019-12-30