| Identification | More | [Name]
Methyl 3-aminocrotonate | [CAS]
14205-39-1 | [Synonyms]
3-AMINO-2-BUTENOIC ACID METHYL ESTER
3-AMINOCROTONATE METHYL ESTER
3-AMINOCROTONIC ACID METHYL ESTER
AMINOCROTONIC ACID METHYL ESTER
METHYL 3-AMINO-2-BUTENOATE
METHYL 3-AMINOCROTONATE
METHYL 4-AMINOCROTONATE
METHYL-BETA-AMINOCROTONATE
3-amino-2-butenoicacimethylester
3-amino-crotonicacimethylester
beta-aminocrotonicacidmethylester
methyl3-aminocrotonoate
methyl 3-amino-trans-but-2-enoate
2-Butenoic acid, 3-amino-, methyl ester
Methyl β-aminobutenate
beta-Iminomethylbutyrate
Methyl 3-iminobutyrate
Crotonic acid, 3-amino-, methyl ester
(1-Aminoethylidene)acetic acid methyl
3-Amino-2-butenoic acid methyl | [EINECS(EC#)]
238-056-5 | [Molecular Formula]
C5H9NO2 | [MDL Number]
MFCD06659463 | [Molecular Weight]
115.13 | [MOL File]
14205-39-1.mol |
| Chemical Properties | Back Directory | [Appearance]
Crystals, yellowish-white | [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) | [Fp ]
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 | [Usage]
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 | [BRN ]
956592 | [InChIKey]
XKORCTIIRYKLLG-ONEGZZNKSA-N | [LogP]
-0.27 at 25℃ | [CAS DataBase Reference]
14205-39-1(CAS DataBase Reference) | [EPA Substance Registry System]
14205-39-1(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn | [Risk Statements ]
R22:Harmful if swallowed.
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S37/39:Wear suitable gloves and eye/face protection .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice . | [WGK Germany ]
3
| [RTECS ]
EM9092500
| [TSCA ]
Yes | [HS Code ]
29224995 |
| Raw materials And Preparation Products | Back Directory | [Raw materials]
Methyl acetoacetate-->Methanol-->Ammonia | [Preparation Products]
Manidipine-->Amlodipine-->Nitrendipine-->Felodipine-->Benidipine-->Isradipine-->Nisoldipine-->Cilnidipine-->Phthaloyl amlodipine-->Lercanidipine hydrochloride-->2(1H)-PYRIDINONE, 4-HYDROXY-3,6-DIMETHYL--->Methyl 6-chloro-2-Methylnicotinate-->4-(2,3-Dichlorophenyl)-2,6-diMethyl-1,4-dihydropyridine-3,5-dicarboxylic acid-->Felodipine 3,5-DiMethyl Ester-->3,5-Pyridinedicarboxylic acid, 4-(2,3-dichlorophenyl)-1,4-dihydro-2,6-dimethyl-, methyl 3-(3-oxo-1,2-benzisothiazol-2(3H)-yl)propyl ester, S,S-dioxide |
| Hazard Information | Back Directory | [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. | [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]. | [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. | [General Description]
Methyl 3-aminocrotonate undergoes waste-free solid-state cascade reaction with crystalline ninhydrin. | [Flammability and Explosibility]
Notclassified | [Synthesis]
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. |
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