Product Name

  • Name

    Enbucrilate

  • EINECS 229-552-2
  • CAS No. 6606-65-1
  • Article Data14
  • CAS DataBase
  • Density 1.005 g/cm3
  • Solubility
  • Melting Point
  • Formula C8H11NO2
  • Boiling Point 232.8 °C at 760 mmHg
  • Molecular Weight 153.181
  • Flash Point 100.6 °C
  • Transport Information
  • Appearance
  • Safety
  • Risk Codes
  • Molecular Structure Molecular Structure of 6606-65-1 (Enbucrilate)
  • Hazard Symbols
  • 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;
  • PSA 50.09000
  • LogP 1.40948

Synthetic route

formaldehyd
50-00-0

formaldehyd

cyanoacetic acid butyl ester
5459-58-5

cyanoacetic acid butyl ester

n-butyl cyanoacrylate
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;
cyanoacetic acid butyl ester
5459-58-5

cyanoacetic acid butyl ester

n-butyl cyanoacrylate
6606-65-1

n-butyl cyanoacrylate

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

di-n-butyloxymethane

cyanoacetic acid butyl ester
5459-58-5

cyanoacetic acid butyl ester

n-butyl cyanoacrylate
6606-65-1

n-butyl cyanoacrylate

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

diacetoxymethane

cyanoacetic acid butyl ester
5459-58-5

cyanoacetic acid butyl ester

n-butyl cyanoacrylate
6606-65-1

n-butyl cyanoacrylate

Conditions
ConditionsYield
With piperazine; toluene-4-sulfonic acid at 120 - 130℃; for 1h; Reagent/catalyst; Time;
ethyl 2-cyanoacrylate
7085-85-0

ethyl 2-cyanoacrylate

butan-1-ol
71-36-3

butan-1-ol

n-butyl cyanoacrylate
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
ethyl 2-cyanoacetate
105-56-6

ethyl 2-cyanoacetate

n-butyl cyanoacrylate
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
n-butyl cyanoacrylate
6606-65-1

n-butyl cyanoacrylate

ethyl 3-(butylamino)but-2-enoate
5065-81-6, 21759-72-8, 21759-73-9

ethyl 3-(butylamino)but-2-enoate

2-[1-Butylamino-eth-(E)-ylidene]-4-cyano-pentanedioic acid 5-butyl ester 1-ethyl ester
71188-28-8

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

Conditions
ConditionsYield
In benzene
n-butyl cyanoacrylate
6606-65-1

n-butyl cyanoacrylate

methyl 3-(benzylamino)but-2-enoate
72002-24-5, 36244-63-0

methyl 3-(benzylamino)but-2-enoate

2-[1-Benzylamino-eth-(E)-ylidene]-4-cyano-pentanedioic acid 5-butyl ester 1-methyl ester
71160-96-8

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

Conditions
ConditionsYield
In benzene
n-butyl cyanoacrylate
6606-65-1

n-butyl cyanoacrylate

benzyl 3-benzylaminobut-2-enoate
71161-03-0

benzyl 3-benzylaminobut-2-enoate

2-[1-Benzylamino-eth-(E)-ylidene]-4-cyano-pentanedioic acid 1-benzyl ester 5-butyl ester
71161-00-7

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

Conditions
ConditionsYield
In benzene
n-butyl cyanoacrylate
6606-65-1

n-butyl cyanoacrylate

ethyl 3-(n-propylamino)but-2-enoate
5091-92-9

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

2-Cyano-4-[1-propylamino-eth-(E)-ylidene]-pentanedioic acid 1-butyl ester 5-ethyl ester
71160-93-5

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

Conditions
ConditionsYield
In benzene
n-butyl cyanoacrylate
6606-65-1

n-butyl cyanoacrylate

ethyl aminocrotonate
626-34-6, 7318-00-5, 41867-20-3

ethyl aminocrotonate

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

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

Conditions
ConditionsYield
In benzene
n-butyl cyanoacrylate
6606-65-1

n-butyl cyanoacrylate

ethyl 3-methylaminocrotonate
870-85-9

ethyl 3-methylaminocrotonate

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

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

Conditions
ConditionsYield
In benzene
n-butyl cyanoacrylate
6606-65-1

n-butyl cyanoacrylate

ethyl 3-ethylamino-2-butenoate
13070-53-6

ethyl 3-ethylamino-2-butenoate

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

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

Conditions
ConditionsYield
In benzene
n-butyl cyanoacrylate
6606-65-1

n-butyl cyanoacrylate

ethyl 3-anilinocrotonate
6287-35-0

ethyl 3-anilinocrotonate

2-Cyano-4-[1-phenylamino-eth-(E)-ylidene]-pentanedioic acid 1-butyl ester 5-ethyl ester
71161-02-9

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

Conditions
ConditionsYield
In benzene
n-butyl cyanoacrylate
6606-65-1

n-butyl cyanoacrylate

ethyl 3-(benzylamino)crotonate
1020-67-3

ethyl 3-(benzylamino)crotonate

2-[1-Benzylamino-eth-(E)-ylidene]-4-cyano-pentanedioic acid 5-butyl ester 1-ethyl ester
71160-98-0

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

Conditions
ConditionsYield
In benzene
n-butyl cyanoacrylate
6606-65-1

n-butyl cyanoacrylate

benzyl-β-aminocrotonate
43107-11-5

benzyl-β-aminocrotonate

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

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

Conditions
ConditionsYield
In benzene
n-butyl cyanoacrylate
6606-65-1

n-butyl cyanoacrylate

methyl 3-aminocrotonate
14205-39-1

methyl 3-aminocrotonate

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

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

Conditions
ConditionsYield
In benzene
n-butyl cyanoacrylate
6606-65-1

n-butyl cyanoacrylate

polybutylcyanoacrylate, nanoparticles: size 290.4, polydispersity index 0.015; Monomer(s): butylcyanoacrylate

polybutylcyanoacrylate, nanoparticles: size 290.4, polydispersity index 0.015; Monomer(s): butylcyanoacrylate

Conditions
ConditionsYield
With D-glucose; citric acid; dextran pH=3;
n-butyl cyanoacrylate
6606-65-1

n-butyl cyanoacrylate

poly(n-butyl cyanoacrylate), anionic emulsion polymerization; monomer(s): n-butyl cyanoacrylate

poly(n-butyl cyanoacrylate), anionic emulsion polymerization; monomer(s): n-butyl cyanoacrylate

Conditions
ConditionsYield
With dodecylbenzene-sulphonic acid In water at 25℃; pH=2;
n-butyl cyanoacrylate
6606-65-1

n-butyl cyanoacrylate

dextran, Mw = 71 kDa

dextran, Mw = 71 kDa

poly(n-butyl 2-cyanoacrylate)-dextran block copolymer

poly(n-butyl 2-cyanoacrylate)-dextran block copolymer

Conditions
ConditionsYield
With ammonium cerium(IV) nitrate; nitric acid at 40℃; pH=1;
n-butyl cyanoacrylate
6606-65-1

n-butyl cyanoacrylate

poly(methyl methacrylate)

poly(methyl methacrylate)

poly(methyl methacrylate); poly(n-butyl cyanoacrylate); mixture of

poly(methyl methacrylate); poly(n-butyl cyanoacrylate); mixture of

Conditions
ConditionsYield
With sulfur dioxide; hydroquinone at 20℃;
n-butyl cyanoacrylate
6606-65-1

n-butyl cyanoacrylate

Reaxys ID: 15739938

Reaxys ID: 15739938

Conditions
ConditionsYield
With hydrogenchloride; sodium hydroxide; sodium dodecyl-sulfate; polysorbate 80 In Hexadecane; water at 0℃; for 0.116667h; pH=7; Product distribution / selectivity; ultrasonication;
With hydrogenchloride; sodium hydroxide; sodium dodecyl-sulfate In Hexadecane; water at 0℃; for 0.116667h; pH=7; ultrasonication;
2-octyl α-cyanoacrylate

2-octyl α-cyanoacrylate

n-butyl cyanoacrylate
6606-65-1

n-butyl cyanoacrylate

poly[(n-butyl cyanoacrylate)-co-(2-octyl cyanoacrylate)]

poly[(n-butyl cyanoacrylate)-co-(2-octyl cyanoacrylate)]

Conditions
ConditionsYield
With hydrogenchloride; poly(ethylene oxide)-poly(propylene oxide)-poly(ethylene oxide) In water at 25℃; for 18h;
n-butyl cyanoacrylate
6606-65-1

n-butyl cyanoacrylate

poly(n-butyl cyanoacrylate)

poly(n-butyl cyanoacrylate)

Conditions
ConditionsYield
at 60℃; for 5h;
With hydrogenchloride; dextran 70 In water for 4h;
n-butyl cyanoacrylate
6606-65-1

n-butyl cyanoacrylate

doxorubicin hydrochloride
25316-40-9

doxorubicin hydrochloride

doxorubicin nanoparticles

doxorubicin nanoparticles

Conditions
ConditionsYield
Stage #1: n-butyl cyanoacrylate With hydrogenchloride; dextran 70 In water for 0.666667h;
Stage #2: doxorubicin hydrochloride In water for 4h;
n-butyl cyanoacrylate
6606-65-1

n-butyl cyanoacrylate

poly(butylcyanoacrylate) nanoparticles

poly(butylcyanoacrylate) nanoparticles

Conditions
ConditionsYield
With hydrogenchloride; fluoresceine isothiocyanate-dextran 70.000; dextran 70 In water at 20℃; for 4h;
formaldehyd
50-00-0

formaldehyd

n-butyl cyanoacrylate
6606-65-1

n-butyl cyanoacrylate

1,4-diammoniocyclohexane di-p-toluenesulfonate
16115-57-4

1,4-diammoniocyclohexane di-p-toluenesulfonate

Conditions
ConditionsYield
With acetic anhydride at 120 - 130℃; for 2h; Reagent/catalyst;

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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