Methyl 3-aminocrotonate
- CAS No.
- 14205-39-1
- Chemical Name:
- Methyl 3-aminocrotonate
- Synonyms
- (Z)-Methyl 3-aMinobut-2-enoate;Methyl (Z)-3-Aminobut-2-enoate;3-Aminocrotonate;methyl (E)-3-aminobut-2-enoate;3-Amino-but-2-enoic acid methyl ester;2-Butenoic acid, 3-amino-, methyl ester;PALO-012;Nifedipine-4;Methyl 3-aminocroton;Nifedipine Impurity 5
- CBNumber:
- CB2222855
- Molecular Formula:
- C5H9NO2
- Molecular Weight:
- 115.13
- MDL Number:
- MFCD00071534
- MOL File:
- 14205-39-1.mol
- MSDS File:
- SDS
- TDS File:
- TDS
| Melting point | 81-83 °C(lit.) |
|---|---|
| Boiling point | 112°C 42mm |
| Density | 1.1808 (rough estimate) |
| vapor pressure | 2.79-2.853hPa at 25℃ |
| refractive index | 1.4538 (estimate) |
| Flash point | 91 °C |
| storage temp. | Keep in dark place,Inert atmosphere,2-8°C |
| solubility | 18g/l |
| form | Crystalline Powder |
| pka | 5.27±0.70(Predicted) |
| color | White to slightly yellow |
| PH | 8-9 (18g/l, H2O, 20℃) |
| Water Solubility | insoluble |
| Sensitive | Hygroscopic |
| BRN | 956592 |
| InChI | 1S/C5H9NO2/c1-4(6)3-5(7)8-2/h3H,6H2,1-2H3/b4-3+ |
| InChIKey | XKORCTIIRYKLLG-ONEGZZNKSA-N |
| SMILES | COC(=O)\C=C(\C)N |
| LogP | -0.27 at 25℃ |
| CAS DataBase Reference | 14205-39-1(CAS DataBase Reference) |
| EWG's Food Scores | 1 |
| FDA UNII | D0M0GH0040 |
| EPA Substance Registry System | 2-Butenoic acid, 3-amino-, methyl ester (14205-39-1) |
| UNSPSC Code | 12352100 |
| NACRES | NA.22 |
SAFETY
Risk and Safety Statements
| Symbol(GHS) |   GHS05,GHS07 |
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|---|---|---|---|---|---|---|---|---|---|---|
| Signal word | Danger | |||||||||
| Hazard statements | H302-H317-H318 | |||||||||
| Precautionary statements | P280-P301+P312+P330-P302+P352-P305+P351+P338+P310 | |||||||||
| PPE | dust mask type N95 (US), Eyeshields, Faceshields, Gloves | |||||||||
| Hazard Codes | Xn | |||||||||
| Risk Statements | 22-36/37/38 | |||||||||
| Safety Statements | 37/39-26-24/25 | |||||||||
| WGK Germany | 3 | |||||||||
| RTECS | EM9092500 | |||||||||
| TSCA | TSCA listed | |||||||||
| HS Code | 29224995 | |||||||||
| Storage Class | 11 - Combustible Solids | |||||||||
| Hazard Classifications | Acute Tox. 4 Oral Eye Dam. 1 Skin Sens. 1 |
|||||||||
| REACH Registrations | Active | |||||||||
| NFPA 704 |
|
Methyl 3-aminocrotonate price More Price(70)
| Manufacturer | Product number | Product description | CAS number | Packaging | Price | Updated | Buy |
|---|---|---|---|---|---|---|---|
| Sigma-Aldrich | S613886 | METHYL 3-AMINO-2-BUTENOATE AldrichCPR | 14205-39-1 | 1 unit | $32.7 | 2026-04-30 | Buy |
| Sigma-Aldrich | 129712 | Methyl 3-aminocrotonate 97% | 14205-39-1 | 100g | $49.9 | 2026-04-30 | Buy |
| Sigma-Aldrich | 129712 | Methyl 3-aminocrotonate 97% | 14205-39-1 | 500g | $126 | 2026-04-30 | Buy |
| TCI Chemical | A1001 | Methyl 3-Aminocrotonate >98.0%(T) | 14205-39-1 | 25g | $55 | 2026-04-30 | Buy |
| TCI Chemical | A1001 | Methyl 3-Aminocrotonate >98.0%(T) | 14205-39-1 | 500g | $311 | 2026-04-30 | Buy |
Methyl 3-aminocrotonate Chemical Properties,Uses,Production
Chemical Properties
Crystals, yellowish-white
Uses
Methyl 3-aminocrotonate is used as intermediate for the syntheses of pharmaceuticals (e.g. 1,4-dihydropyridine derivatives) as well as for the manufacture of stabilizers and plastics. Product Data Sheet
Uses
Nitrendipine (N490150) metabolite. The pharmacokinetics of Nitrendipine was studied in the rat and 6 major metabolites were identified.
Uses
Methyl 3-aminocrotonate (Methyl 3-amino-2-butenoate) was used to synthesize 4-aryl-1,4-dihydropyridines possessing potential calcium channel blocking activity.
Preparation
3-Aminocrotonate Esters, e.g., methyl 3- aminocrotonate [14205-39-1] (3-amino-2-butenoic acid, methyl ester) can be prepared by treatment of acetoacetates with aqueous ammonia. They are mainly used in the production of a series of the dihydropyridine-type calcium antagonists.
Application
Methyl 3-aminocrotonate reacts with benzene to form the corresponding E-2-phenyliodonio tosylate in good yield. This new alkenyl iodonium salt upon reaction with various nucleophiles offers an easy access to substituted enamine derivatives of crotonic acid. The reaction can be also extended to N-substituted crotonates[1].
General Description
Methyl 3-aminocrotonate undergoes waste-free solid-state cascade reaction with crystalline ninhydrin.
Flammability and Explosibility
Not classified
Synthesis
105-45-3
14205-39-1
The general procedure for the synthesis of methyl 3-aminocrotonate from methyl acetoacetate was as follows: 25 kg of methyl acetoacetate and 20 kg of methanol were pumped into an ammoniation reactor. The temperature of the reaction system was controlled in the range of 0-10°C using an ice-water bath with continuous stirring, and the ammonia was slowly introduced until white crystals were precipitated, and then the introduction of ammonia was stopped. The reaction mixture was allowed to stand under refrigeration overnight and then centrifuged to collect the white crystals. The resulting white crystals were transferred to an ammonia refining kettle and purified by adding 15 kg of methanol, heating the mixture until complete dissolution, followed by cryocrystallization. The mixture was centrifuged again and filtered to collect the filter cake. The filter cake was placed in a hot air circulating oven and dried at 50-60 °C for 8 hours to give 18.6 kg of methyl 3-aminocrotonate. The product needs to be stored at 0 to -10°C for 20 to 24 hours. The yield of this process was 21 kg with a weight yield range of 74.4-84.0% and a molar yield range of 75.0-85.0%.
References
[1] IOANNIS PAPOUTSIS; Anastasios V ; Spyros Spyroudis . Reactivity of a new alkenyl phenyliodonium tosylate derived from methyl 3-aminocrotonate[J]. Tetrahedron, 1998. DOI:10.1016/S0040-4020(97)10354-4.
Methyl 3-aminocrotonate Preparation Products And Raw materials
Raw materials
Preparation Products
1of3
| Supplier | Tel | Country | ProdList | Advantage | |
|---|---|---|---|---|---|
| XI'AN VEDA CHEMICAL CO.,LTD | 029-88665278 18392371173 | cordelia@vedachem.com | China | 50 | 58 |
| Shanghai Chengyu Biotechnology Co., Ltd. | 021-51525055 | 309639130@qq.com | China | 42 | 58 |
| Huanggang Saikang Pharmaceutical Co.,Ltd | -- | hgsaikang@163.com | China | 11 | 58 |
| TOSUN PHARM | 020-66392521-118 18922260391 | 3004261881@qq.com | China | 7994 | 58 |
| J & K SCIENTIFIC LTD. | 18210857532 18210857532 | jkinfo@jkchemical.com | China | 96815 | 76 |
| Meryer (Shanghai) Chemical Technology Co., Ltd. | 4006356688 18621169109 | market03@meryer.com | China | 40202 | 62 |
| 3B Pharmachem (Wuhan) International Co.,Ltd. | 18930552037 | 3bsc@sina.com | China | 15813 | 69 |
| Alfa Aesar | 400-6106006 | saleschina@alfa-asia.com | China | 30103 | 84 |
| TCI (Shanghai) Development Co., Ltd. | 021-67121386 | Sales-CN@TCIchemicals.com | China | 24512 | 81 |
| ShangHai DEMO Chemical Co.,Ltd | 400-021-7337 2355568890 | sales@demochem.com | China | 2569 | 57 |
View Lastest Price from Methyl 3-aminocrotonate manufacturers
| Image | Update time | Product | Price | Min. Order | Purity | Supply Ability | Manufacturer | |
|---|---|---|---|---|---|---|---|---|
 |
2026-09-01 | Methyl 3-aminocrotonate
14205-39-1
|
1kg | 99% | 10000kg | Shaanxi TNJONE Pharmaceutical Co., Ltd | ||
 |
2026-07-16 | Methyl 3-aminocrotonate
14205-39-1
|
1kg | 98% | 1000kgs | Shaanxi Dideu New Materials Co. Ltd | ||
 |
2026-03-20 | Methyl 3-aminocrotonate
14205-39-1
|
$10.00 | 1KG | 99% | 10 mt | Hebei Chuanghai Biotechnology Co., Ltd |
-
- Methyl 3-aminocrotonate
14205-39-1
- $0.00
- 99%
- Shaanxi TNJONE Pharmaceutical Co., Ltd
-
- Methyl 3-aminocrotonate
14205-39-1
- $0.00
- 98%
- Shaanxi Dideu New Materials Co. Ltd
-
- Methyl 3-aminocrotonate
14205-39-1
- $10.00
- 99%
- Hebei Chuanghai Biotechnology Co., Ltd
