Methyl 3-aminocrotonate

Base Information

• Chemical Name: Methyl 3-aminocrotonate
• CAS No.: 21731-17-9
• Deprecated CAS: 916520-50-8
• Molecular Formula: C5H9NO2
• Molecular Weight: 115.132
• European Community (EC) Number: 238-056-5,244-549-6
• NSC Number: 65444
• UNII: LWO4Y3WLG7
• Nikkaji Number: J284.541E
• Mol file: 21731-17-9.mol

Synonyms:Methyl 3-aminocrotonate;14205-39-1;methyl (E)-3-aminobut-2-enoate;(E)-methyl 3-aminobut-2-enoate;methyl 3-aminobut-2-enoate;80012-11-9;methyl (2E)-3-aminobut-2-enoate;LWO4Y3WLG7;2-Butenoic acid, 3-amino-, methyl ester;(E)-Methyl 3-aminocrotonate;Methyl 3-amino-2-butenoate;2-butenoic acid, 3-amino-, methyl ester, (2E)-;Methyl 3-amino-2-butenoate, (2E)-;EC 238-056-5;2-Butenoic acid, 3-amino-, methyl ester, (E)-;EINECS 238-056-5;Methyl3-aminocrotonate;Crotonic acid, beta-amino-, methyl ester;NSC-65444;UNII-LWO4Y3WLG7;Methyl-.beta.-aminocrotonate;SCHEMBL62213;SCHEMBL822962;UNII-D0M0GH0040;Methyl 3-aminocrotonate, 97%;methyl(E)-3-aminobut-2-enoate;D0M0GH0040;NSC65444;3-Aminoisocrotonic acid methyl ester;MFCD00008072;STK802360;AKOS000120083;Methyl (2E)-3-amino-2-butenoate #;AS-13006;NIFEDIPINE IMPURITY D [EP IMPURITY];Crotonic acid, .beta.-amino-, methyl ester;Methyl |A-aminobutenate Methyl 3-aminocrotonate;SR-01000944878;Q-102738;SR-01000944878-1;F0001-0502;Methyl 3-aminocrotonate, Lonza quality, 98.0-100.3% (w/w) (GC)

Chemical Property of Methyl 3-aminocrotonate

Chemical Property:

• Vapor Pressure: 0.166mmHg at 25°C
• Melting Point: 81-83oC
• 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
• 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:

98%,99%, ^*data from raw suppliers

Safty Information:

• Pictogram(s): R22:; R36/37/38:
• Hazard Codes: Xn:Harmful
• Statements: R22:; R36/37/38:
• Safety Statements: S26:; S37/39:

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=CC(=O)OC)N
• Isomeric SMILES: C/C(=C\C(=O)OC)/N

Technology Process of Methyl 3-aminocrotonate

There total 7 articles about Methyl 3-aminocrotonate 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: 94.0%

acetoacetic acid methyl ester (105-45-3) → methyl 3-aminocrotonate (21731-17-9)

Guidance literature:

With ammonium hydroxide; at 20 ℃; for 0.333333h;

DOI:10.1016/S0040-4020(01)01127-9

Reference yield: 85.0%

methyl (Z)-3-acetamido-2-butenoate (72569-97-2,136744-85-9,67654-56-2) + benzylamine (100-46-9) → methyl 3-aminocrotonate (21731-17-9) + 3-benzyl-2,6-dimethyl-3H-pyrimidin-4-one (69912-32-9)

Guidance literature:

With trimethylaluminum; In n-heptane; dichloromethane; at 20 ℃; for 7h;

DOI:10.1021/ol049921v

Reference yield: 84.0%

methyl (Z)-3-acetamido-2-butenoate (72569-97-2,136744-85-9,67654-56-2) + aniline (62-53-3) → methyl 3-aminocrotonate (21731-17-9) + 2,6-dimethyl-3-phenyl-4(3H)-pyrimidinone (32363-53-4)

Guidance literature:

With trimethylaluminum; In n-heptane; dichloromethane; at 20 ℃; for 5h;

DOI:10.1021/ol049921v

upstream raw materials:

acetoacetic acid methyl ester

methyl (Z)-3-acetamido-2-butenoate

aniline

benzylamine

Downstream raw materials:

4-Methoxycarbonyl-5-methyl-2-oxo-4-pyrrolin-3-essigsaeure

3-[3,5-Dioxo-1-phenyl-pyrazolidin-(4Z)-ylidene]-butyric acid methyl ester

antipyrine

dimethyl 2,6-dimethylpyridine-3,5-dicarboxylate

Refernces

• 1、 Chen, Chunhui,Zhan, Ensheng,Li, Yong,Shen, Wenjie. "Enantioselective hydrogenation of β-dehydroamino acids on a cinchonidine-modified palladium catalyst". . p. 117 - 121. Retrieved 2013/09/23.
• 2、 Jacobs, Jan,Kesteleyn, Bart,De Kimpe, Norbert. "First straightforward synthesis of 2,4-disubstituted benz[g]isoquinoline-3,5,10(2H)-triones, 1,2,3,5-substituted naphtho[3,2,1-de]isoquinoline-4,7-diones, and 6-substituted benzo[h]pyrido[3,4,5-kl]-1,2,3,4-tetrahydroacridine-5,8-diones". . p. 7545 - 7554. Retrieved 2008/12/20.