-
Name
Methyl 3-amino-4-methylthiophene-2-carboxylate
- EINECS 285-060-8
- CAS No. 85006-31-1
- Article Data4
- CAS DataBase
- Density 1.264 g/cm3
- Solubility 1g/L at 35℃
- Melting Point 85-88 °C(lit.)
- Formula C7H9NO2S
- Boiling Point 318.6 °C at 760 mmHg
- Molecular Weight 171.22
- Flash Point 146.5 °C
- Transport Information
- Appearance white to light yellow crystal powder
- Safety 26-36-24/25-22
- Risk Codes 36/37/38
-
Molecular Structure
-
Hazard Symbols
Xi
- 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;
- PSA 80.56000
- LogP 2.00650
Synthetic route
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2689-70-5
4-methyl-3-oxotetrahydro-2-thiophencarboxylic acid methyl ester
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-
85006-31-1
3-amino-4-methyl-2-thiophenecarboxylic acid methyl ester
| Conditions | Yield |
|---|---|
| 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 |
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125089-02-3
3-amino-2-carbomethoxy-4-methyl-4,5-dihydrothiophene
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-
85006-31-1
3-amino-4-methyl-2-thiophenecarboxylic acid methyl ester
| Conditions | Yield |
|---|---|
| With dihydrogen peroxide In ethyl acetate; isopropyl alcohol |
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-
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 | Yield |
|---|---|
| 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 | Yield |
|---|---|
| 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 | Yield |
|---|---|
| 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 | Yield |
|---|---|
| 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% |
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-
85006-31-1
3-amino-4-methyl-2-thiophenecarboxylic acid methyl ester
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87685-15-2
2,4-dimethyl-3-amino-thiophene
| Conditions | Yield |
|---|---|
| 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 |
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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 | Yield |
|---|---|
| In toluene for 3h; Heating; | 94% |
-
-
18063-02-0
2,6-difluorobenzoylchloride
-
-
85006-31-1
3-amino-4-methyl-2-thiophenecarboxylic acid methyl ester
| Conditions | Yield |
|---|---|
| With pyridine at 20℃; for 168h; | 94% |
-
-
57-13-6
urea
-
-
85006-31-1
3-amino-4-methyl-2-thiophenecarboxylic acid methyl ester
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-
35265-81-7
7-methylthieno<3,2-d>pyrimidine-2,4-dione
| Conditions | Yield |
|---|---|
| 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
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-
35265-81-7
7-methylthieno<3,2-d>pyrimidine-2,4-dione
| Conditions | Yield |
|---|---|
| With urea In (2S)-N-methyl-1-phenylpropan-2-amine hydrate; N,N-dimethyl-formamide | 93.7% |
| With potassium cyanate; sodium hydroxide; acetic acid In water | 84% |
| 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 |
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-
401-78-5
3-bromo-1-trifluoromethylbenzene
-
-
85006-31-1
3-amino-4-methyl-2-thiophenecarboxylic acid methyl ester
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-
1246226-63-0
methyl 3-amino-4-methyl-5-(3-trifluoromethylphenyl)-thiophene-2-carboxylate
| Conditions | Yield |
|---|---|
| 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% |
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696-59-3
cis,trans-2,5-dimethoxytetrahydrofuran
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-
7379-35-3
4-chlorpyridine hydrochloride
-
-
85006-31-1
3-amino-4-methyl-2-thiophenecarboxylic acid methyl ester
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-
179751-31-6
methyl 4-methyl-3-(pyrrol-1-yl)thiophene-2-carboxylate
| Conditions | Yield |
|---|---|
| In 1,4-dioxane; water | 91% |
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77287-34-4, 77287-35-5, 60100-09-6
formamide
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-
85006-31-1
3-amino-4-methyl-2-thiophenecarboxylic acid methyl ester
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-
175137-13-0
7-methyl-3,4-dihydrothieno[3,2-d]pyrimidin-4-one
| Conditions | Yield |
|---|---|
| at 200℃; for 24h; | 91% |
| at 200℃; for 24h; | 91% |
| at 20℃; | 60% |
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-
2042-37-7
o-cyanobromobenzene
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-
85006-31-1
3-amino-4-methyl-2-thiophenecarboxylic acid methyl ester
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-
1246226-66-3
methyl 3-amino-5-(2-cyanophenyl)-4-methylthiophene-2-carboxylate
| Conditions | Yield |
|---|---|
| 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% |
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-
6952-59-6
3-cyanobromobenzene
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-
85006-31-1
3-amino-4-methyl-2-thiophenecarboxylic acid methyl ester
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-
1393718-85-8
methyl 3-amino-5-(3-cyanophenyl)-4-methylthiophene-2-carboxylate
| Conditions | Yield |
|---|---|
| With PdCl(C3H5)(dppb); potassium acetate In N,N-dimethyl acetamide at 120℃; for 20h; Inert atmosphere; | 90% |
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99-90-1
para-bromoacetophenone
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-
85006-31-1
3-amino-4-methyl-2-thiophenecarboxylic acid methyl ester
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-
1393718-78-9
methyl 5-(4-acetylphenyl)-3-amino-4-methylthiophene-2-carboxylate
| Conditions | Yield |
|---|---|
| With PdCl(C3H5)(dppb); potassium acetate In N,N-dimethyl acetamide at 120℃; for 20h; Inert atmosphere; | 90% |
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-
19524-06-2
4-bromopyridine hydrochloride
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-
85006-31-1
3-amino-4-methyl-2-thiophenecarboxylic acid methyl ester
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-
1246226-68-5
methyl 3-amino-4-methyl-5-pyridin-4-ylthiophene-2-carboxylate
| Conditions | Yield |
|---|---|
| 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% |
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-
460-00-4
1-Bromo-4-fluorobenzene
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-
85006-31-1
3-amino-4-methyl-2-thiophenecarboxylic acid methyl ester
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-
691394-01-1
methyl 3-amino-5-(4-fluorophenyl)-4-methyl-thiophene-2-carboxylate
| Conditions | Yield |
|---|---|
| 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% |
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-
392-83-6
o-trifluoromethylphenyl bromide
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-
85006-31-1
3-amino-4-methyl-2-thiophenecarboxylic acid methyl ester
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-
1393718-90-5
methyl 3-amino-4-methyl-5-(2-trifluoromethylphenyl)-thiophene-2-carboxylate
| Conditions | Yield |
|---|---|
| With PdCl(C3H5)(dppb); potassium acetate In N,N-dimethyl acetamide at 120℃; for 20h; Inert atmosphere; | 88% |
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-
610-94-6
2-bromobenzoic acid methyl ester
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-
85006-31-1
3-amino-4-methyl-2-thiophenecarboxylic acid methyl ester
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-
1246226-65-2
methyl 3-amino-5-(2-methoxycarbonylphenyl)-4-methylthiophene-2-carboxylate
| Conditions | Yield |
|---|---|
| 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% |
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-
623-00-7
4-bromobenzenecarbonitrile
-
-
85006-31-1
3-amino-4-methyl-2-thiophenecarboxylic acid methyl ester
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-
1246226-62-9
methyl 3-amino-5-(4-cyanophenyl)-4-methylthiophene-2-carboxylate
| Conditions | Yield |
|---|---|
| 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% |
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-
1122-91-4
4-bromo-benzaldehyde
-
-
85006-31-1
3-amino-4-methyl-2-thiophenecarboxylic acid methyl ester
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-
1246226-60-7
methyl 3-amino-5-(4-formylphenyl)-4-methylthiophene-2-carboxylate
| Conditions | Yield |
|---|---|
| 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% |
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-
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 | Yield |
|---|---|
| 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
| Conditions | Yield |
|---|---|
| In tetrahydrofuran at 20℃; for 0.25h; | 84% |
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-
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 | Yield |
|---|---|
| With PdCl(C3H5)(dppb); potassium acetate In N,N-dimethyl acetamide at 120℃; for 20h; Inert atmosphere; | 84% |
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-
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 | Yield |
|---|---|
| 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
| Conditions | Yield |
|---|---|
| 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 | Yield |
|---|---|
| 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 | Yield |
|---|---|
| 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 | Yield |
|---|---|
| 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% |
Methyl 3-amino-4-methylthiophene-2-carboxylate 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.
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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.
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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
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