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Conditions | Yield |
---|---|
Stage #1: formaldehyd; cyanoacetic acid butyl ester With 1,5,7-triazabicyclo[5.5.0]dec-5-ene; triphenylphosphine at 20 - 85℃; under 30 Torr; for 1h; Green chemistry; Stage #2: With phosphorus pentoxide; hydroquinone at 20 - 220℃; under 3 Torr; for 1h; Reagent/catalyst; Green chemistry; | 95.3% |
Stage #1: formaldehyd; cyanoacetic acid butyl ester With piperidine; sodium hydrogencarbonate; sodium carbonate; sodium 4-dodecylbenzenesulfonate In water at 80 - 90℃; for 1h; Stage #2: With phosphoric acid In water Reagent/catalyst; | 81.3% |
Stage #1: formaldehyd; cyanoacetic acid butyl ester With piperidine hydrochloride In toluene at 90 - 200℃; for 0.4h; Dean-Stark; Microwave irradiation; Stage #2: With phosphorus pentoxide; toluene-4-sulfonic acid; hydroquinone In toluene at 200℃; under 17 Torr; for 0.25h; Microwave irradiation; | 72% |
With nitromethane In acetonitrile at 90℃; for 6.5h; Temperature; Knoevenagel Condensation; | |
Stage #1: formaldehyd; cyanoacetic acid butyl ester for 3h; Reflux; Stage #2: Pyrolysis; |
Conditions | Yield |
---|---|
With hydroquinone at 20℃; for 0.0833333h; Neat (no solvent); | 79% |
Conditions | Yield |
---|---|
With dodecylbenzenesulfonic acid piperidine salt at 125 - 127℃; Reagent/catalyst; Temperature; | 68% |
Conditions | Yield |
---|---|
With piperazine; toluene-4-sulfonic acid at 120 - 130℃; for 1h; Reagent/catalyst; Time; |
Conditions | Yield |
---|---|
With phosphoric acid; sulfuric acid; toluene-4-sulfonic acid; acetic acid; chloroacetic acid at 100 - 115℃; Reagent/catalyst; Temperature; | 440 g |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: tetrabutyl titanate / 3 h / Reflux 2.1: 3 h / Reflux 2.2: Pyrolysis View Scheme |
n-butyl cyanoacrylate
ethyl 3-(butylamino)but-2-enoate
2-[1-Butylamino-eth-(E)-ylidene]-4-cyano-pentanedioic acid 5-butyl ester 1-ethyl ester
Conditions | Yield |
---|---|
In benzene |
n-butyl cyanoacrylate
methyl 3-(benzylamino)but-2-enoate
2-[1-Benzylamino-eth-(E)-ylidene]-4-cyano-pentanedioic acid 5-butyl ester 1-methyl ester
Conditions | Yield |
---|---|
In benzene |
n-butyl cyanoacrylate
benzyl 3-benzylaminobut-2-enoate
2-[1-Benzylamino-eth-(E)-ylidene]-4-cyano-pentanedioic acid 1-benzyl ester 5-butyl ester
Conditions | Yield |
---|---|
In benzene |
n-butyl cyanoacrylate
ethyl 3-(n-propylamino)but-2-enoate
2-Cyano-4-[1-propylamino-eth-(E)-ylidene]-pentanedioic acid 1-butyl ester 5-ethyl ester
Conditions | Yield |
---|---|
In benzene |
Molecular Structure of Enbucrilate (CAS NO.6606-65-1):
IUPAC Name: butyl 2-cyanoprop-2-enoate
Empirical Formula: C8H11NO2
Molecular Weight: 153.1784
EINECS: 229-552-2
H bond acceptors: 3
H bond donors: 0
Freely Rotating Bonds: 5
Polar Surface Area: 50.09 Å2
Index of Refraction: 1.442
Molar Refractivity: 40.36 cm3
Molar Volume: 152.3 cm3
Surface Tension: 34.2 dyne/cm
Density: 1.005 g/cm3
Flash Point: 100.6 °C
Enthalpy of Vaporization: 46.95 kJ/mol
Boiling Point: 232.8 °C at 760 mmHg
Vapour Pressure: 0.0578 mmHg at 25°C
InChI
InChI=1/C8H11NO2/c1-3-4-5-11-8(10)7(2)6-9/h2-5H2,1H3
Smiles
C(OCCCC)(C(C#N)=C)=O
Enbucrilate , with CAS number is 6606-65-1, can be called Butyl 2-cyano-2-propenoate ; n-Butyl 2-cyanoacrylate ; Integuseal MicrobialSealant ; InteguSeal Clear ; Histacryl Blue ; Butyl a-cyanoacrylate ; Butyl cyanoacrylate ; Butyl 2-cyanoacrylate .