Methyl 3-aminocrotonate

Iupac Name：methyl (E)-3-aminobut-2-enoate

Molecular Weight：115.13

Modify Date.: 2023-03-06 12:08

Introduction: 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 View more+

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1. Names and Identifiers

1.1 Name: Methyl 3-aminocrotonate
1.2 Synonyms: 2-Butenoic acid, 3-amino-, methyl ester 3-AMINO-2-BUTENOIC ACID METHYL ESTER 3-Aminobut-2-enoic acid methyl ester 3-AMINOCROTONATE METHYL ESTER 3-AMINOCROTONIC ACID METHYL ESTER AMINOCROTONIC ACID METHYL ESTER Butanoic acid, 3-imino-, methyl ester, (3E)- Crotonic acid, 3-amino-, methyl ester Methyl (3E)-3-iminobutanoate Methyl 3-amino-2-butenenoate METHYL 3-AMINO-2-BUTENOATE Methyl 3-aminobut-2-enoate Methyl 3-aminocrotonoate METHYL 4-AMINOCROTONATE Methyl β-aminocrotonate METHYL-BETA-AMINOCROTONATE β-Aminocrotonic acid methyl ester

1.3 CAS No.: 14205-39-1

1.4 CID: 643918

1.5 EINECS(EC#): 238-056-5

1.6 Molecular Formula: C5H9NO2 (isomer)

1.7 Inchi: InChI=1S/C5H9NO2/c1-4(6)3-5(7)8-2/h3H,6H2,1-2H3/b4-3-

1.8 InChkey: XKORCTIIRYKLLG-ARJAWSKDSA-N

1.9 Canonical Smiles: CC(=CC(=O)OC)N

1.10 Isomers Smiles: C/C(=C/C(=O)OC)/N

2. Properties

2.1 Density: 1.1808 (rough estimate)

2.1 Melting point: 81-83 °C(lit.)

2.1 Boiling point: 112°C 42mm

2.1 Refractive index: 1.4538 (estimate)

2.1 Flash Point: 91 °C

2.1 Precise Quality: 115.06300

2.1 PSA: 52.32000

2.1 logP: 0.72220

2.1 Solubility: 18g/l

2.2 Appearance: White to slightly yellow Crystalline Powder

2.3 Storage: Hygroscopic. Ambient temperatures.

2.4 Chemical Properties: Crystals, yellowish-white

2.5 Color/Form: White to slightly yellow

2.6 PH: 8-9 (18g/l, H2O, 20℃)

2.7 pKa: 5.27±0.70(Predicted)

2.8 Water Solubility: H2O: insoluble

2.9 Stability: Stable at room temperature in closed containers under normal storage and handling conditions.

2.10 StorageTemp: Keep container closed when not in use. Store in a cool, dry, well-ventilated area away from incompatible substances. Keep containers tightly closed.

3. Use and Manufacturing

3.1 GHS Classification: Signal: Danger
GHS Hazard Statements
Aggregated GHS information provided by 48 companies from 10 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

H302 (93.75%): Harmful if swallowed [Warning Acute toxicity, oral]
H317 (37.5%): May cause an allergic skin reaction [Warning Sensitization, Skin]
H318 (35.42%): Causes serious eye damage [Danger Serious eye damage/eye irritation]
H319 (10.42%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
H330 (52.08%): Fatal if inhaled [Danger Acute toxicity, inhalation]

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

Precautionary Statement Codes
P260, P261, P264, P270, P271, P272, P280, P284, P301+P312, P302+P352, P304+P340, P305+P351+P338, P310, P320, P321, P330, P333+P313, P337+P313, P363, P403+P233, P405, and P501

3.2 Methods of Manufacturing: 25kg of methyl acetoacetate and 20kg of methanol were pumped into the ammoniation reaction tank.The internal temperature was controlled to 0 to 10 ° C with iced water, stirred, and ammonia gas was introduced, and white crystals were precipitated, and the ammonia was stopped after 4 hours.After freezing overnight, the mixture was centrifuged to obtain white crystals, which was placed in an ammoniated refining tank, and 15 kg of methanol for purification was added thereto, and the mixture was heated to dissolve, and then freeze-crystallized at 0 to -10 ° C for 20 to 24 hours.The mixture was centrifuged and filtered, and the filter cake was dried in a hot air circulating oven at 50 to 60 ° C for 8 hours to obtain methyl 3-aminocrotonate of 18.6 to 21 kg, and the weight yield range was 74.4 to 84.0percent, and the molar yield range was 75.0 to 85.0percent.

3.3 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

4. Safety and Handling

4.1 Hazard Codes: Xn

4.1 Risk Statements: 22-36/37/38

4.1 Safety Statements: 37/39-26-24/25

4.1 Hazard Declaration: H302 + H332

4.1 RIDADR: 200kgs

4.1 Caution Statement: P261-P301 + P312 + P330

4.1 WGK Germany: 3

4.1 RTECS: EM9092500

4.1 Sensitive: Hygroscopic

5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Acute toxicity - Oral, Category 4

Skin sensitization, Category 1

Serious eye damage, Category 1

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word	Danger
Hazard statement(s)	H302 Harmful if swallowed H317 May cause an allergic skin reaction H318 Causes serious eye damage
Precautionary statement(s)
Prevention	P264 Wash ... thoroughly after handling. P270 Do not eat, drink or smoke when using this product. P261 Avoid breathing dust/fume/gas/mist/vapours/spray. P272 Contaminated work clothing should not be allowed out of the workplace. P280 Wear protective gloves/protective clothing/eye protection/face protection.
Response	P301+P312 IF SWALLOWED: Call a POISON CENTER/doctor/\u2026if you feel unwell. P330 Rinse mouth. P302+P352 IF ON SKIN: Wash with plenty of water/... P333+P313 If skin irritation or rash occurs: Get medical advice/attention. P321 Specific treatment (see ... on this label). P362+P364 Take off contaminated clothing and wash it before reuse. P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. P310 Immediately call a POISON CENTER/doctor/\u2026
Storage	none
Disposal	P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

View all

6. NMR Spectrum

13C NMR : in CDCl3

13C NMR : Predict

1H NMR : 400 MHz in CDCl3

1H NMR : 90 MHz in CDCl3

7. Synthesis Route

14205-39-1Total: 4 Synthesis Route

105-45-3 237 Suppliers

14205-39-1 261 Suppliers

Literatures:
Cho; Ueda; Mizuno; Ishihara; Aisaka; Noguchi Chemical and Pharmaceutical Bulletin, 1989 , vol. 37, # 8 p. 2117 - 2121
Yield: ~97%

105-45-3 237 Suppliers

5977-14-0 40 Suppliers

14205-39-1 261 Suppliers

Literatures:
Monatshefte fuer Chemie, , vol. 28, p. 4 Atti della Accademia Nazionale dei Lincei, Classe di Scienze Fisiche, Matematiche e Naturali, Rendiconti, , vol. <5> 14 I, p. 395 Chem. Zentralbl., , vol. 76, # I p. 1559 Chemische Berichte, , vol. 38, p. 1127 Atti della Accademia Nazionale dei Lincei, Classe di Scienze Fisiche, Matematiche e Naturali, Rendiconti, , vol. <5> 14 I, p. 394 Chem. Zentralbl., , vol. 76, # I p. 1559
Yield: null

6372-01-6

14205-39-1 261 Suppliers

Literatures:
Bulletin de la Societe Chimique de France, , vol. <3> 13, p. 71
Yield: null

View all

8. Precursor and Product

precursor:

7664-41-7

105-45-3

6372-01-6

product :

80307-08-0

36745-93-4

34785-00-7

43114-35-8

21881-77-6

73257-47-3

40801-09-0

59225-86-4

121497-22-1

104713-75-9

67035-22-7

55315-50-9

65719-09-7

121497-05-0

121497-07-2

95838-55-4

22260-83-9

40016-70-4

21731-17-9

121497-18-5

223788-08-7

27525-74-2

73257-48-4

64603-74-3

View all

9. Other Information

9.0 Storage Conditions: 25kg of methyl acetoacetate and 20kg of methanol were pumped into the ammoniation reaction tank.The internal temperature was controlled to 0 to 10 ° C with iced water, stirred, and ammonia gas was introduced, and white crystals were precipitated, and the ammonia was stopped after 4 hours.After freezing overnight, the mixture was centrifuged to obtain white crystals, which was placed in an ammoniated refining tank, and 15 kg of methanol for purification was added thereto, and the mixture was heated to dissolve, and then freeze-crystallized at 0 to -10 ° C for 20 to 24 hours.The mixture was centrifuged and filtered, and the filter cake was dried in a hot air circulating oven at 50 to 60 ° C for 8 hours to obtain methyl 3-aminocrotonate of 18.6 to 21 kg, and the weight yield range was 74.4 to 84.0percent, and the molar yield range was 75.0 to 85.0percent.

9.1 Manufacturing Info: 2-Butenoic acid, 3-amino-, methyl ester: ACTIVE

9.2 BRN: 956592

9.3 Chemical Properties: Crystals, yellowish-white

9.4 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

9.5 Uses: Nitrendipine (N490150) metabolite. The pharmacokinetics of Nitrendipine was studied in the rat and 6 major metabolites were identified.

10. Computational chemical data

Molecular Weight: 115.13g/mol
Molecular Formula: C₅H₉NO₂
Compound Is Canonicalized: True
XLogP3-AA: 0.6
Exact Mass: 115.063328530
Monoisotopic Mass: 115.063328530
Complexity: 118
Rotatable Bond Count: 2
Hydrogen Bond Donor Count: 1
Hydrogen Bond Acceptor Count: 3
Topological Polar Surface Area: 52.3
Heavy Atom Count: 8
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 1
Undefined Bond Stereocenter Count: 0
Isotope Atom Count: 0
Covalently-Bonded Unit Count: 1
CACTVS Substructure Key Fingerprint: AAADccBiMAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAHgAQAAAACAiBgAICCABABACIACTSSAAAAAAAAgAACAAAAEAABAAAIQAAEAAAEAAAIUAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA==

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