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85006-31-1

Basic Information
CAS No.: 85006-31-1
Name: 2-Thiophenecarboxylicacid, 3-amino-4-methyl-, methyl ester
Molecular Structure:
Molecular Structure of 85006-31-1 (2-Thiophenecarboxylicacid, 3-amino-4-methyl-, methyl ester)
Formula: C7H9NO2S
Molecular Weight: 171.21
Synonyms: 2-Methoxycarbonyl-3-amino-4-methylthiophene;3-Amino-4-methylthiophene-2-carboxylic acid methyl ester;3-Amino-4-methyl-2-thiophene carboxylic acid ester;
EINECS: 285-060-8
Density: 1.264 g/cm3
Melting Point: 85-88 °C(lit.)
Boiling Point: 318.6 °C at 760 mmHg
Flash Point: 146.5 °C
Solubility:
Appearance: white to light yellow crystal powder
Hazard Symbols: IrritantXi
Risk Codes: 36/37/38
Safety: 26-36-24/25-22
Transport Information:
PSA: 80.56000
LogP: 2.00650
Synthetic route
2689-70-5

4-methyl-3-oxotetrahydro-2-thiophencarboxylic acid methyl ester

85006-31-1

3-amino-4-methyl-2-thiophenecarboxylic acid methyl ester

Conditions
ConditionsYield
Stage #1: 4-methyl-3-oxotetrahydro-2-thiophencarboxylic acid methyl ester With iron(III) chloride; 1,3,5-trichloro-2,4,6-triazine; hydroxylamine hydrochloride In N,N-dimethyl-formamide at 70 - 90℃; for 4h;
Stage #2: With ammonium hydroxide for 0.5h; Reagent/catalyst; Temperature;
96.5%
With MH2OH*HCl In acetonitrile for 5h; Heating;64%
With hydroxylamine hydrochloride In acetonitrile
125089-02-3

3-amino-2-carbomethoxy-4-methyl-4,5-dihydrothiophene

85006-31-1

3-amino-4-methyl-2-thiophenecarboxylic acid methyl ester

Conditions
ConditionsYield
With dihydrogen peroxide In ethyl acetate; isopropyl alcohol
24424-99-5

di-tert-butyl dicarbonate

85006-31-1

3-amino-4-methyl-2-thiophenecarboxylic acid methyl ester

1097629-78-1

tert‐butyl N‐(4‐methylthiophen‐3‐yl)carbamate

Conditions
ConditionsYield
Stage #1: 3-amino-4-methyl-2-thiophenecarboxylic acid methyl ester With potassium hydroxide In water at 20 - 80℃; for 0.5h;
Stage #2: With hydrogenchloride In water at 50 - 60℃; for 0.25h;
Stage #3: di-tert-butyl dicarbonate With potassium hydroxide In hexane; water; acetone at -10 - 20℃;
100%
Stage #1: 3-amino-4-methyl-2-thiophenecarboxylic acid methyl ester With water; potassium hydroxide at 20 - 80℃; Inert atmosphere;
Stage #2: With hydrogenchloride In water at 50 - 60℃;
Stage #3: di-tert-butyl dicarbonate With potassium hydroxide In water at 5 - 20℃; Inert atmosphere;
81%
15050-24-5

N-(benzyloxycarbonyl)glycyl chloride

85006-31-1

3-amino-4-methyl-2-thiophenecarboxylic acid methyl ester

135429-76-4

3-((benzyloxycarbonyl)glycyl)amino-2-methoxycarbonyl-4-methylthiophene

Conditions
ConditionsYield
In N,N,N,N,N,N-hexamethylphosphoric triamide; acetonitrile Ambient temperature;99.3%
64-18-6

formic acid

85006-31-1

3-amino-4-methyl-2-thiophenecarboxylic acid methyl ester

443762-03-6

methyl 3-formamido-4-methylthiophene-2-carboxylate

Conditions
ConditionsYield
Stage #1: formic acid With acetic anhydride at 0℃;
Stage #2: 3-amino-4-methyl-2-thiophenecarboxylic acid methyl ester at 0 - 20℃; for 4h;
97%
With (1-methyl-3-(3-sulfopropyl)-1H-imidazol-3-ium)3[PW12O403-] In neat (no solvent) at 70℃; for 1h; Green chemistry;88%
Stage #1: formic acid; 3-amino-4-methyl-2-thiophenecarboxylic acid methyl ester In acetic anhydride at 0 - 20℃; for 18h;
Stage #2: for 0.5h;
81%
407-25-0

trifluoroacetic anhydride

85006-31-1

3-amino-4-methyl-2-thiophenecarboxylic acid methyl ester

1000409-43-7

methyl 4-methyl-3-[(trifluoroacetyl)amino]thiophene-2-carboxylate

Conditions
ConditionsYield
With pyridine In acetonitrile at 0 - 20℃;96%
With pyridine In acetonitrile at 0 - 20℃; for 2h;96%
With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 2h;95%
85006-31-1

3-amino-4-methyl-2-thiophenecarboxylic acid methyl ester

87685-15-2

2,4-dimethyl-3-amino-thiophene

Conditions
ConditionsYield
With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 80℃; for 3h; Inert atmosphere;96%
With lithium aluminium tetrahydride In tetrahydrofuran for 3.5h; Cooling with ice; Reflux;60.6%
Stage #1: 3-amino-4-methyl-2-thiophenecarboxylic acid methyl ester With lithium aluminium tetrahydride In tetrahydrofuran for 3.5h; Cooling with ice; Reflux;
Stage #2: With sodium hydroxide In tetrahydrofuran; water at 0℃; for 1h;
60.6%
With sodium bis(2-methoxyethoxy)aluminum dihydride In potassium hydroxide; toluene
With sodium bis(2-methoxyethoxy)aluminum dihydride In potassium hydroxide; toluene
541-41-3

chloroformic acid ethyl ester

85006-31-1

3-amino-4-methyl-2-thiophenecarboxylic acid methyl ester

118252-13-4

3-Ethoxycarbonylamino-4-methyl-thiophene-2-carboxylic acid methyl ester

Conditions
ConditionsYield
In toluene for 3h; Heating;94%
18063-02-0

2,6-difluorobenzoylchloride

85006-31-1

3-amino-4-methyl-2-thiophenecarboxylic acid methyl ester

3-(2,6-difluoro-benzylamino)-4-methyl-thiophene-2-carboxylic acid methyl ester

Conditions
ConditionsYield
With pyridine at 20℃; for 168h;94%
85006-31-1

3-amino-4-methyl-2-thiophenecarboxylic acid methyl ester

35265-81-7

7-methylthieno<3,2-d>pyrimidine-2,4-dione

Conditions
ConditionsYield
In N,N-dimethyl-formamide for 2.5h; Heating / reflux;93.7%
for 1.5h; Heating;90%
In N,N-dimethyl-formamide at 200℃; for 1.5h;77%
at 160 - 200℃;61%
85006-31-1

3-amino-4-methyl-2-thiophenecarboxylic acid methyl ester

35265-81-7

7-methylthieno<3,2-d>pyrimidine-2,4-dione

Conditions
ConditionsYield
With urea In (2S)-N-methyl-1-phenylpropan-2-amine hydrate; N,N-dimethyl-formamide93.7%
With potassium cyanate; sodium hydroxide; acetic acid In water84%
Multi-step reaction with 2 steps
1: H2O / 12 h / Ambient temperature
2: 5percent aq. NaOH / 2 h
View Scheme
Multi-step reaction with 3 steps
1: dichloromethane / 0.37 h / -78 - 20 °C
2: hydrogenchloride; water / 2 h / Heating / reflux
3: methanol; sodium hydroxide; water / 2 h / Heating / reflux
View Scheme
401-78-5

3-bromo-1-trifluoromethylbenzene

85006-31-1

3-amino-4-methyl-2-thiophenecarboxylic acid methyl ester

1246226-63-0

methyl 3-amino-4-methyl-5-(3-trifluoromethylphenyl)-thiophene-2-carboxylate

Conditions
ConditionsYield
With PdCl(C3H5)(dppb); potassium acetate In N,N-dimethyl acetamide at 120℃; for 20h; Inert atmosphere;92%
With PdCl(C3H5)(dppb); potassium acetate In N,N-dimethyl acetamide at 120℃; for 20h; Inert atmosphere;92%
696-59-3

cis,trans-2,5-dimethoxytetrahydrofuran

7379-35-3

4-chlorpyridine hydrochloride

85006-31-1

3-amino-4-methyl-2-thiophenecarboxylic acid methyl ester

179751-31-6

methyl 4-methyl-3-(pyrrol-1-yl)thiophene-2-carboxylate

Conditions
ConditionsYield
In 1,4-dioxane; water91%
85006-31-1

3-amino-4-methyl-2-thiophenecarboxylic acid methyl ester

175137-13-0

7-methyl-3,4-dihydrothieno[3,2-d]pyrimidin-4-one

Conditions
ConditionsYield
at 200℃; for 24h;91%
at 200℃; for 24h;91%
at 20℃;60%
2042-37-7

o-cyanobromobenzene

85006-31-1

3-amino-4-methyl-2-thiophenecarboxylic acid methyl ester

1246226-66-3

methyl 3-amino-5-(2-cyanophenyl)-4-methylthiophene-2-carboxylate

Conditions
ConditionsYield
With PdCl(C3H5)(dppb); potassium acetate In N,N-dimethyl acetamide at 120℃; for 20h; Inert atmosphere;90%
With PdCl(C3H5)(dppb); potassium acetate In N,N-dimethyl acetamide at 120℃; for 20h; Inert atmosphere;90%
6952-59-6

3-cyanobromobenzene

85006-31-1

3-amino-4-methyl-2-thiophenecarboxylic acid methyl ester

1393718-85-8

methyl 3-amino-5-(3-cyanophenyl)-4-methylthiophene-2-carboxylate

Conditions
ConditionsYield
With PdCl(C3H5)(dppb); potassium acetate In N,N-dimethyl acetamide at 120℃; for 20h; Inert atmosphere;90%
99-90-1

para-bromoacetophenone

85006-31-1

3-amino-4-methyl-2-thiophenecarboxylic acid methyl ester

1393718-78-9

methyl 5-(4-acetylphenyl)-3-amino-4-methylthiophene-2-carboxylate

Conditions
ConditionsYield
With PdCl(C3H5)(dppb); potassium acetate In N,N-dimethyl acetamide at 120℃; for 20h; Inert atmosphere;90%
19524-06-2

4-bromopyridine hydrochloride

85006-31-1

3-amino-4-methyl-2-thiophenecarboxylic acid methyl ester

1246226-68-5

methyl 3-amino-4-methyl-5-pyridin-4-ylthiophene-2-carboxylate

Conditions
ConditionsYield
With PdCl(C3H5)(dppb); potassium acetate In N,N-dimethyl acetamide at 120℃; for 20h; Inert atmosphere;89%
With PdCl(C3H5)(dppb); potassium acetate In N,N-dimethyl acetamide at 120℃; for 20h; Inert atmosphere;89%
460-00-4

1-Bromo-4-fluorobenzene

85006-31-1

3-amino-4-methyl-2-thiophenecarboxylic acid methyl ester

691394-01-1

methyl 3-amino-5-(4-fluorophenyl)-4-methyl-thiophene-2-carboxylate

Conditions
ConditionsYield
With PdCl(C3H5)(dppb); potassium acetate In N,N-dimethyl acetamide at 120℃; for 20h; Inert atmosphere;89%
With PdCl(C3H5)(dppb); potassium acetate In N,N-dimethyl acetamide at 120℃; for 20h; Inert atmosphere;89%
392-83-6

o-trifluoromethylphenyl bromide

85006-31-1

3-amino-4-methyl-2-thiophenecarboxylic acid methyl ester

1393718-90-5

methyl 3-amino-4-methyl-5-(2-trifluoromethylphenyl)-thiophene-2-carboxylate

Conditions
ConditionsYield
With PdCl(C3H5)(dppb); potassium acetate In N,N-dimethyl acetamide at 120℃; for 20h; Inert atmosphere;88%
610-94-6

2-bromobenzoic acid methyl ester

85006-31-1

3-amino-4-methyl-2-thiophenecarboxylic acid methyl ester

1246226-65-2

methyl 3-amino-5-(2-methoxycarbonylphenyl)-4-methylthiophene-2-carboxylate

Conditions
ConditionsYield
With PdCl(C3H5)(dppb); potassium acetate In N,N-dimethyl acetamide at 120℃; for 20h; Inert atmosphere;87%
With PdCl(C3H5)(dppb); potassium acetate In N,N-dimethyl acetamide at 120℃; for 20h; Inert atmosphere;87%
623-00-7

4-bromobenzenecarbonitrile

85006-31-1

3-amino-4-methyl-2-thiophenecarboxylic acid methyl ester

1246226-62-9

methyl 3-amino-5-(4-cyanophenyl)-4-methylthiophene-2-carboxylate

Conditions
ConditionsYield
With PdCl(C3H5)(dppb); potassium acetate In N,N-dimethyl acetamide at 120℃; for 20h; Inert atmosphere;87%
With PdCl(C3H5)(dppb); potassium acetate In N,N-dimethyl acetamide at 120℃; for 20h; Inert atmosphere;87%
1122-91-4

4-bromo-benzaldehyde

85006-31-1

3-amino-4-methyl-2-thiophenecarboxylic acid methyl ester

1246226-60-7

methyl 3-amino-5-(4-formylphenyl)-4-methylthiophene-2-carboxylate

Conditions
ConditionsYield
With PdCl(C3H5)(dppb); potassium acetate In N,N-dimethyl acetamide at 120℃; for 20h; Inert atmosphere;87%
With PdCl(C3H5)(dppb); potassium acetate In N,N-dimethyl acetamide at 120℃; for 20h; Inert atmosphere;87%
10342-83-3

4'-Bromopropiophenone

85006-31-1

3-amino-4-methyl-2-thiophenecarboxylic acid methyl ester

1246226-61-8

methyl 3-amino-4-methyl-5-(4-propionylphenyl)-thiophene-2-carboxylate

Conditions
ConditionsYield
With PdCl(C3H5)(dppb); potassium acetate In N,N-dimethyl acetamide at 120℃; for 20h; Inert atmosphere;86%
With PdCl(C3H5)(dppb); potassium acetate In N,N-dimethyl acetamide at 120℃; for 20h; Inert atmosphere;86%
4755-77-5

Ethyl oxalyl chloride

85006-31-1

3-amino-4-methyl-2-thiophenecarboxylic acid methyl ester

3-(ethoxyoxalylamino)-4-methylthiophene-2-carboxylic acid methyl ester

Conditions
ConditionsYield
In tetrahydrofuran at 20℃; for 0.25h;84%
106-39-8

bromochlorobenzene

85006-31-1

3-amino-4-methyl-2-thiophenecarboxylic acid methyl ester

691394-00-0

methyl 3-amino-5-(4-chlorophenyl)-4-methylthiophene-2-carboxylate

Conditions
ConditionsYield
With PdCl(C3H5)(dppb); potassium acetate In N,N-dimethyl acetamide at 120℃; for 20h; Inert atmosphere;84%
108-37-2

1-bromo-3-chlorobenzene

85006-31-1

3-amino-4-methyl-2-thiophenecarboxylic acid methyl ester

1293119-61-5

3-amino-5-(3-chlorophenyl)-4-methyl-thiophene-2-carboxylic acid methyl ester

Conditions
ConditionsYield
With PdCl(C3H5)(dppb); potassium acetate In N,N-dimethyl acetamide at 120℃; for 20h; Inert atmosphere;84%
85006-31-1

3-amino-4-methyl-2-thiophenecarboxylic acid methyl ester

(3-amino-4-methylthiophen-2-yl)methanol

Conditions
ConditionsYield
With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; for 4h; Cooling with ice;83.9%
586-78-7

para-nitrophenyl bromide

85006-31-1

3-amino-4-methyl-2-thiophenecarboxylic acid methyl ester

725234-25-3

methyl 3-amino-4-methyl-5-(4-nitrophenyl)-thiophene-2-carboxylate

Conditions
ConditionsYield
With PdCl(C3H5)(dppb); potassium acetate In N,N-dimethyl acetamide at 120℃; for 20h; Inert atmosphere;83%
With PdCl(C3H5)(dppb); potassium acetate In N,N-dimethyl acetamide at 120℃; for 20h; Inert atmosphere;83%
3132-99-8

m-bromobenzoic aldehyde

85006-31-1

3-amino-4-methyl-2-thiophenecarboxylic acid methyl ester

1393718-83-6

methyl 3-amino-5-(3-formylphenyl)-4-methylthiophene-2-carboxylate

Conditions
ConditionsYield
With PdCl(C3H5)(dppb); potassium acetate In N,N-dimethyl acetamide at 120℃; for 20h; Inert atmosphere;83%
402-43-7

p-trifluoromethylphenyl bromide

85006-31-1

3-amino-4-methyl-2-thiophenecarboxylic acid methyl ester

1246226-56-1

methyl 3-amino-4-methyl-5-(4-trifluoromethylphenyl)-thiophene-2-carboxylate

Conditions
ConditionsYield
With PdCl(C3H5)(dppb); potassium acetate In N,N-dimethyl acetamide at 120℃; for 20h; Inert atmosphere;82%
With PdCl(C3H5)(dppb); potassium acetate In N,N-dimethyl acetamide at 120℃; for 20h; Inert atmosphere;82%
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  • 85006-31-1  2-Thiophenecarboxylicacid, 3-amino-4-methyl-, methyl ester

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    85006-31-1 2-Thiophenecarboxylicacid, 3-amino-4-methyl-, methyl ester

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    3-Amino-4-methyl-2-thiophenecarboxylic acid methyl ester

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    Methyl-3-amino-4-methylthiophene-2-carboxylate

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    Product name Methyl 3-amino-4-methylthiophene-2-carboxylate Synonyms 3-AMINO-4-METHYLTHIOPHENE-2-CARBOXYLIC ACID METHYL ESTER CAS No. 85006-31-1 EINECS No. 28

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    Methyl 3-amino-4-methylthiophene-2-carboxylate

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  • CAS 85006-31-1 Methyl 3-Amino-4-Methylthiophene-2-Carboxylate Liquid

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    85006-31-1

    CAS 85006-31-1 Methyl 3-Amino-4-Methylthiophene-2-Carboxylate Liquid

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Specification

The Methyl 3-amino-4-methylthiophene-2-carboxylate with cas registry number of 85006-31-1 is also known as 3-Amino-4-methylthiophene-2-carboxylic acid methyl ester. It belongs to the following categories: Esters; Thiophenes & Benzothiophenes; Organic acids; API intermediates; Thiophen. It also has an EINECS registry number which is 285-060-8 with appearance of white to light yellow crystal powder. Besides, both its systematic name and IUPAC name are the same which is called methyl 3-amino-4-methylthiophene-2-carboxylate.

The physical properties about this chemical are: (1)ACD/LogP: 2.10; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2.1; (4)ACD/LogD (pH 7.4): 2.1; (5)ACD/BCF (pH 5.5): 23.28; (6)ACD/BCF (pH 7.4): 23.29; (7)ACD/KOC (pH 5.5): 331.21; (8)ACD/KOC (pH 7.4): 331.27; (9)#H bond acceptors: 3; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 3; (12)Index of Refraction: 1.586; (13)Molar Refractivity: 45.47 cm3; (14)Molar Volume: 135.3 cm3; (15)Surface Tension: 49.3 dyne/cm; (16)Density: 1.264 g/cm3; (17)Flash Point: 146.5 °C; (18)Enthalpy of Vaporization: 56.01 kJ/mol; (19)Boiling Point: 318.6 °C at 760 mmHg; (20)Vapour Pressure: 0.000357 mmHg at 25°C.

Preparation: this chemical can be made by 4-methyl-3-oxo-tetrahydro-thiophene-2-carboxylic acid methyl ester together with reagent MH2OH . HCl and solvent acetonitrile. The reaction time is 5 hours.

Uses of 3-amino-4-methylthiophene-2-carboxylate: it can be used to synthetize 7-methyl-1H-thieno[3,2-d]pyrimidine-2,4-dione with urea. The reaction occurs at temperature of 200 ℃ with solvent dimethylformamide. The reaction time is 90 min with 77% yield.

When you are using this chemical, please be cautious about it as the following:
This chemical is irritating to eyes, respiratory system and skin. Hence, wear suitable protective clothing during using it. And avoid contact with skin and eyes. Do not breathe dust. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C(OC)c1scc(c1N)C;
(2)InChI: InChI=1/C7H9NO2S/c1-4-3-11-6(5(4)8)7(9)10-2/h3H,8H2,1-2H3;
(3)InChIKey: YICRPERKKBDRSP-UHFFFAOYAE