Basic information
- Standard SMILES
COC(=O)C=C(C)N- InChIKey
XKORCTIIRYKLLG-UHFFFAOYSA-N- Molecular formula
- C5H9NO2
- Average molar mass
- 115.13 g/mol
- Monoisotopic mass
- 115.06332853
Names & identifiers
- Preferred name
- Methyl 3-aminobut-2-enoate
- IUPAC
- methyl 3-aminobut-2-enoate
- English name
- Methyl 3-aminocrotonate
- Molecular formula
- C5H9NO2
- Molecular weight
- 115.13
Names & synonyms
14205-39-1methyl 3-aminobut-2-enoate2-Butenoic acid, 3-amino-, methyl esterNifedipine EP Impurity DMethyl 3-amino-2-butenoateSCHEMBL62213CHEMBL3560468SCHEMBL10559216MFCD00071534AKOS0252436533-amino-but-2-enoic acid methyl esterAB00926
Show more names
(Z)-Methyl 3-aMinobut-2-enoateMethyl (Z)-3-Aminobut-2-enoate3-Aminocrotonatemethyl (E)-3-aminobut-2-enoatePALO-012Nifedipine-4Methyl 3-aminocrotonNifedipine Impurity 5
SY005584DB-042603Benidipine Impurity E; Nifedipine EP Impurity D
Database identifiers
- CAS
14205-39-1- PubChem CID
- 84253
- DTXSID
DTXSID7051715- ChEMBL
CHEMBL3560468
Properties
Computed structural properties
- XLogP
- 0.6
- Topological polar surface area
- 52.3 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 2
- Heavy atoms
- 8
- Formal charge
- 0
- Complexity
- 118
Physicochemical properties
- Melting point
- 81 · 81-83 °C(lit.)
- Boiling point
- 112 °C · 112°C 42mm
- Density
- 1.1808 · 1.1808 (rough estimate)
- vapor pressure
- 2.79 · 2.79-2.853hPa at 25℃
- refractive index
- 1.4538 · 1.4538 (estimate)
- Flash point
- 91 °C · 91 °C
- storage temp.
- 2 · Keep in dark place,Inert atmosphere,2-8°C
- solubility
- 18 g/l · 18g/l
- form
- Crystalline Powder
- pka
- 5.27 · 5.27±0.70(Predicted)
- color
- White to slightly yellow
- PH
- 8 · 8-9 (18g/l, H2O, 20℃)
- Water Solubility
- insoluble
- Sensitive
- Hygroscopic
- BRN
- 956592 · 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 · -0.27 at 25℃
- CAS DataBase Reference
- 14205 · 14205-39-1(CAS DataBase Reference)
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 0 M0GH0040 · D0M0GH0040
- EPA Substance Registry System
- 2 · 2-Butenoic acid, 3-amino-, methyl ester (14205-39-1)
- UNSPSC Code
- 12352100 · 12352100
- NACRES
- 22 · NA.22
- Symbol(GHS)
- 5 · GHS05,GHS07
- Signal word
- Danger
- Hazard statements
- 302 · H302-H317-H318
- Precautionary statements
- 280 · P280-P301+P312+P330-P302+P352-P305+P351+P338+P310
- PPE
- 95 · dust mask type N95 (US), Eyeshields, Faceshields, Gloves
- Hazard Codes
- Xn
- Risk Statements
- 22 · 22-36/37/38
- Safety Statements
- 37 · 37/39-26-24/25
- WGK Germany
- 3 · 3
- RTECS
- 9092500 · EM9092500
- TSCA
- TSCA listed
- HS Code
- 29224995 · 29224995
- Storage Class
- 11 · 11 - Combustible Solids
- Hazard Classifications
- 4 OralEye · Acute Tox. 4 OralEye Dam. 1Skin Sens. 1
- REACH Registrations
- Active
Safety & regulation
Hazard information
Regulatory Information
Chemical: 2-Butenoic acid, 3-amino-, methyl ester
2-Butenoic acid, 3-amino-, methyl ester: Does not have an individual approval but may be used under an appropriate group standard
Regulatory information
Regulatory Information
Chemical: 2-Butenoic acid, 3-amino-, methyl ester
2-Butenoic acid, 3-amino-, methyl ester: Does not have an individual approval but may be used under an appropriate group standard
Safety data
- PPE
- dust mask type N95 (US), Eyeshields, Faceshields, Gloves
- wgk
- 3
- tsca
- TSCA listed
- rtecs
- EM9092500
- hs_code
- 29224995
- risk_code
- 22-36/37/38
- Signal word
- Danger
- Symbol(GHS)
- GHS05,GHS07
- hazard_code
- Xn
- safety_code
- 37/39-26-24/25
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H302-H317-H318
- REACH Registrations
- Active
- Hazard Classifications
- Acute Tox. 4 OralEye Dam. 1Skin Sens. 1
- Precautionary statements
- P280-P301+P312+P330-P302+P352-P305+P351+P338+P310
Chemistry & industry
Uses & manufacturing
General Manufacturing Information2-Butenoic acid, 3-amino-, methyl ester: ACTIVE
Applications
UsesMethyl 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
UsesMethyl 3-aminocrotonate (Methyl 3-amino-2-butenoate) was used to synthesize 4-aryl-1,4-dihydropyridines possessing potential calcium channel blocking activity.
UsesNitrendipine (N490150) metabolite. The pharmacokinetics of Nitrendipine was studied in the rat and 6 major metabolites were identified.
General DescriptionMethyl 3-aminocrotonate undergoes waste-free solid-state cascade reaction with crystalline ninhydrin.
Preparation methods
Preparation3-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.
Upstream & downstream products
Upstream raw materials
Downstream products
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Related reactions
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