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Enbucrilate

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Name

Enbucrilate

EINECS 229-552-2
CAS No. 6606-65-1 Density 1.005 g/cm3
PSA 50.09000 LogP 1.40948
Solubility N/A Melting Point N/A
Formula C8H11NO2 Boiling Point 232.8 °C at 760 mmHg
Molecular Weight 153.181 Flash Point 100.6 °C
Transport Information N/A Appearance N/A
Safety Risk Codes N/A
Molecular Structure Molecular Structure of 6606-65-1 (Enbucrilate) Hazard Symbols N/A
Synonyms

Acrylicacid, 2-cyano-, butyl ester (6CI,7CI,8CI);BK 201 (adhesive);BK 301 (adhesive);Butyl 2-cyanoacrylate;Butyl cyanoacrylate;Butyl a-cyanoacrylate;Histacryl Blue;Indermil;InteguSeal Clear;Integuseal;Integuseal MicrobialSealant;Sicomet 6000;Tisuacryl;n-Butyl 2-cyanoacrylate;

Article Data 14

Enbucrilate Synthetic route

50-00-0

formaldehyd

5459-58-5

cyanoacetic acid butyl ester

6606-65-1

n-butyl cyanoacrylate

Conditions
ConditionsYield
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;
5459-58-5

cyanoacetic acid butyl ester

6606-65-1

n-butyl cyanoacrylate

Conditions
ConditionsYield
With hydroquinone at 20℃; for 0.0833333h; Neat (no solvent);79%
2568-90-3

di-n-butyloxymethane

5459-58-5

cyanoacetic acid butyl ester

6606-65-1

n-butyl cyanoacrylate

Conditions
ConditionsYield
With dodecylbenzenesulfonic acid piperidine salt at 125 - 127℃; Reagent/catalyst; Temperature;68%
628-51-3

diacetoxymethane

5459-58-5

cyanoacetic acid butyl ester

6606-65-1

n-butyl cyanoacrylate

Conditions
ConditionsYield
With piperazine; toluene-4-sulfonic acid at 120 - 130℃; for 1h; Reagent/catalyst; Time;
7085-85-0

ethyl 2-cyanoacrylate

71-36-3

butan-1-ol

6606-65-1

n-butyl cyanoacrylate

Conditions
ConditionsYield
With phosphoric acid; sulfuric acid; toluene-4-sulfonic acid; acetic acid; chloroacetic acid at 100 - 115℃; Reagent/catalyst; Temperature;440 g
105-56-6

ethyl 2-cyanoacetate

6606-65-1

n-butyl cyanoacrylate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: tetrabutyl titanate / 3 h / Reflux
2.1: 3 h / Reflux
2.2: Pyrolysis
View Scheme
6606-65-1

n-butyl cyanoacrylate

5065-81-6, 21759-72-8, 21759-73-9

ethyl 3-(butylamino)but-2-enoate

71188-28-8

2-[1-Butylamino-eth-(E)-ylidene]-4-cyano-pentanedioic acid 5-butyl ester 1-ethyl ester

Conditions
ConditionsYield
In benzene
6606-65-1

n-butyl cyanoacrylate

72002-24-5, 36244-63-0

methyl 3-(benzylamino)but-2-enoate

71160-96-8

2-[1-Benzylamino-eth-(E)-ylidene]-4-cyano-pentanedioic acid 5-butyl ester 1-methyl ester

Conditions
ConditionsYield
In benzene
6606-65-1

n-butyl cyanoacrylate

71161-03-0

benzyl 3-benzylaminobut-2-enoate

71161-00-7

2-[1-Benzylamino-eth-(E)-ylidene]-4-cyano-pentanedioic acid 1-benzyl ester 5-butyl ester

Conditions
ConditionsYield
In benzene
6606-65-1

n-butyl cyanoacrylate

5091-92-9

ethyl 3-(n-propylamino)but-2-enoate

71160-93-5

2-Cyano-4-[1-propylamino-eth-(E)-ylidene]-pentanedioic acid 1-butyl ester 5-ethyl ester

Conditions
ConditionsYield
In benzene

Enbucrilate Chemical Properties

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 Specification

  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 .

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