2-Butenoic acid, 3-amino-, methyl ester

Base Information

• Chemical Name: 2-Butenoic acid, 3-amino-, methyl ester
• CAS No.: 14205-39-1
• Molecular Formula: C5H9NO2
• Molecular Weight: 115.132
• Hs Code.: 29224995
• European Community (EC) Number: 238-056-5,244-549-6
• DSSTox Substance ID: DTXSID7051715
• ChEMBL ID: CHEMBL3560468
• Mol file: 14205-39-1.mol

Synonyms:Methyl 3-aminocrotonate;14205-39-1;methyl 3-aminobut-2-enoate;2-Butenoic acid, 3-amino-, methyl ester;EINECS 238-056-5;Crotonic acid, beta-amino-, methyl ester;Methyl 3-amino-2-butenoate;DTXSID7051715;Methyl 3-Aminocrotanate;CHEMBL3560468;BCP15340;MFCD00071534;AKOS025243653;3-amino-but-2-enoic acid methyl ester;AB00926;LS-47087;SY005584;FT-0615038;FT-0628322

Chemical Property of 2-Butenoic acid, 3-amino-, methyl ester

Chemical Property:

• Appearance/Colour: yellowish-white crystals
• Vapor Pressure: 0.166mmHg at 25°C
• Melting Point: 81-83 °C(lit.)
• Refractive Index: 1.439
• Boiling Point: 194.1 °C at 760 mmHg
• PKA: 5.27±0.70(Predicted)
• Flash Point: 65.3 °C
• PSA: 52.32000
• Density: 1.031 g/cm³
• LogP: 0.72220
• Storage Temp.: Store below +30°C.
• Sensitive.: Hygroscopic
• Solubility.: 18g/l
• Water Solubility.: insoluble
• XLogP3: 0.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 115.063328530
• Heavy Atom Count: 8
• Complexity: 118

Purity/Quality:

99% ^*data from raw suppliers

Methyl 3-aminocrotonate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-36/37/38
• Safety Statements: 37/39-26-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(=CC(=O)OC)N
• 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 Nitrendipine (N490150) metabolite. The pharmacokinetics of Nitrendipine was studied in the rat and 6 major metabolites were identified. Methyl 3-aminocrotonate (Methyl 3-amino-2-butenoate) was used to synthesize 4-aryl-1,4-dihydropyridines possessing potential calcium channel blocking activity.

Technology Process of 2-Butenoic acid, 3-amino-, methyl ester

There total 7 articles about 2-Butenoic acid, 3-amino-, methyl ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 97.0%

acetoacetic acid methyl ester (105-45-3) → methyl (E)-3-aminocrotonate (14205-39-1)

Guidance literature:

With ammonium acetate; In methanol;

DOI:10.1016/j.tetlet.2008.04.027

Reference yield: 96.0%

acetoacetic acid methyl ester (105-45-3) → methyl 3-aminocrotonate (14205-39-1)

Guidance literature:

With ammonium hydroxide; In methanol; water; for 16h; Heating;

DOI:10.1248/cpb.37.2117

Reference yield: 72.0%

(-)-methyl (2S,3R)-2-(indol-3-yl)-1-(2-hydroxyethyl)piperidine-3-carboxylate + lithium enolate of methyl acetate (57570-85-1) → (-)-methyl 3-((2S,3R)-1-(2-hydroxyethyl)-2-(indol-3-yl)piperidin-3-yl)-3-oxopropanoate + methyl 3-aminocrotonate (14205-39-1)

Guidance literature:

(-)-methyl (2S,3R)-2-(indol-3-yl)-1-(2-hydroxyethyl)piperidine-3-carboxylate; With lithium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; for 0.333333h;

lithium enolate of methyl acetate; at -78 - 20 ℃; for 20.0833h;

DOI:10.1002/asia.201200575

upstream raw materials:

acetoacetic acid methyl ester

methyl (E)-3-chloro-2-butenoate

ammonia

lithium enolate of methyl acetate

Downstream raw materials:

(Z)-methyl 3-(benzamido)but-2-enoate

methyl (E)-3-benzamido-3-butenoate

4-furan-2-yl-2,6-dimethyl-1,4-dihydro-pyridine-3,5-dicarboxylic acid dimethyl ester

2,5,5,7,7-pentamethyl-4-(3-trifluoromethyl-phenyl)-1,4,5,7-tetrahydro-furo[3,4-b]pyridine-3-carboxylic acid methyl ester

Refernces

• 1、 Suarez, Margarita,De Armas, Merly,Ramirez, Oney,Alvarez, Amaury,Martinez-Alvarez, Roberto,Molero, Dolores,Seoane, Carlos,Liz, Ramon,De Armas, Hector Novoa,Blaton, Norbert M.,Peeters, Oswald M.,Martin, Nazario. "Synthesis and structural study of new highly lipophilic 1,4-dihydropyridines". . p. 1567 - 1576. Retrieved 2005.
• 2、 Filipan-Litvic, Mirela,Litvic, Mladen,Cepanec, Ivica,Vinkovic, Vladimir. "Hantzsch synthesis of 2,6-dimethyl-3,5-dimethoxycarbonyl-4-(o- methoxyphenyl)-1,4-dihydropyridine; a novel cyclisation leading to an unusual formation of 1-amino-2-methoxycarbonyl-3,5-bis(o-methoxyphenyl)-4-oxa- cyclohexan-1-ene". . p. 2546 - 2558. Retrieved 2007.
• 3、 Hariprasad, K. S.,Prakasham, R. S.,Praveena, G.,Raju, B. China,Ramya, S.,Suchitra Rani, K.,Tiwari, A. K.,Zehra, A.. "Synthesis and Biological Activities of Nicotinaldehyde Based 1,4-Dihydropyridinedicarboxylates". . p. 1335 - 1340. Retrieved 2021/12/23.
• 4、 Nejati, Maryam,Sadeghpour, Hossein,Ranjbar, Sara,Javidnia, Katayoun,Edraki, Najmeh,Saso, Luciano,Firuzi, Omidreza,Miri, Ramin. "Unsymmetric dihydropyridines bearing 2-pyridyl methyl carboxylate as modulators of P-glycoprotein; Synthesis and biological evaluation in resistant and non-resistant cancer cells". . p. 603 - 614. Retrieved 2019/08/06.