6606-65-1

Basic information

• Product Name: enbucrilate
• Synonyms: enbucrilate;n-Butyl 2-Cyanoacrylate;BUTYLCYANOACRYLATE;2-cyano-2-propenoic acid butyl ester;2-Propenoic acid, 2-cyano-, butyl ester;2-propenoic,2-cyano-,butyl ester;2-Cyanoacrylic acid butyl ester;butyl 2-cyanoprop-2-enoate
• CAS NO: 6606-65-1
• Molecular Formula: C₈H₁₁NO₂
• Molecular Weight: 153.17844
• EINECS: 229-552-2
• Product Categories: acrylate
• Mol File: 6606-65-1.mol
• Article Data: 12

Chemical Properties

• Boiling Point: bp1.8 68°
• Flash Point: closed cup: >176°F (>80°C)
• Appearance: /
• Density: d20 0.989
• Vapor Pressure: 0.57mmHg at 25°C
• Refractive Index: n20D 1.4424; nD25 1.4410
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• CAS DataBase Reference: enbucrilate(CAS DataBase Reference)
• NIST Chemistry Reference: enbucrilate(6606-65-1)
• EPA Substance Registry System: enbucrilate(6606-65-1)

Safety Data

• Hazardous Substances Data: 6606-65-1(Hazardous Substances Data)

Usage

Description

Enbucrilate is a bacteriostatic agent that is commonly used in the medical field for its painless application. It possesses adhesive properties, making it suitable for various applications in wound care and treatment of bleeding.

Uses

Used in Medical Industry:
Enbucrilate is used as an adhesive for lacerations of the skin, providing a painless and effective means of wound closure. Its bacteriostatic properties help prevent infection and promote healing.
Enbucrilate is also used in the treatment of bleeding from vascular structures, thanks to its ability to form a stable adhesive bond that can effectively control bleeding and facilitate clot formation.

InChI:InChI=1/C7H11NO/c1-2-3-4-7(9)5-6-8/h2-5H2,1H3

Synthetic route

formaldehyd (50-00-0) + cyanoacetic acid butyl ester (5459-58-5) → n-butyl cyanoacrylate (6606-65-1)

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;

cyanoacetic acid butyl ester (5459-58-5) → n-butyl cyanoacrylate (6606-65-1)

Conditions	Yield
With hydroquinone at 20℃; for 0.0833333h; Neat (no solvent);	79%

di-n-butyloxymethane (2568-90-3) + cyanoacetic acid butyl ester (5459-58-5) → n-butyl cyanoacrylate (6606-65-1)

Conditions	Yield
With dodecylbenzenesulfonic acid piperidine salt at 125 - 127℃; Reagent/catalyst; Temperature;	68%

diacetoxymethane (628-51-3) + cyanoacetic acid butyl ester (5459-58-5) → n-butyl cyanoacrylate (6606-65-1)

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

ethyl 2-cyanoacrylate (7085-85-0) + butan-1-ol (71-36-3) → n-butyl cyanoacrylate (6606-65-1)

Conditions	Yield
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) → n-butyl cyanoacrylate (6606-65-1)

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 (6606-65-1) + ethyl 3-(butylamino)but-2-enoate (5065-81-6, 21759-72-8, 21759-73-9) → 2-[1-Butylamino-eth-(E)-ylidene]-4-cyano-pentanedioic acid 5-butyl ester 1-ethyl ester (71188-28-8)

Conditions	Yield
In benzene

n-butyl cyanoacrylate (6606-65-1) + methyl 3-(benzylamino)but-2-enoate (72002-24-5, 36244-63-0) → 2-[1-Benzylamino-eth-(E)-ylidene]-4-cyano-pentanedioic acid 5-butyl ester 1-methyl ester (71160-96-8)

Conditions	Yield
In benzene

n-butyl cyanoacrylate (6606-65-1) + benzyl 3-benzylaminobut-2-enoate (71161-03-0) → 2-[1-Benzylamino-eth-(E)-ylidene]-4-cyano-pentanedioic acid 1-benzyl ester 5-butyl ester (71161-00-7)

Conditions	Yield
In benzene

n-butyl cyanoacrylate (6606-65-1) + ethyl 3-(n-propylamino)but-2-enoate (5091-92-9) → 2-Cyano-4-[1-propylamino-eth-(E)-ylidene]-pentanedioic acid 1-butyl ester 5-ethyl ester (71160-93-5)

Conditions	Yield
In benzene

n-butyl cyanoacrylate (6606-65-1) + ethyl aminocrotonate (626-34-6, 7318-00-5, 41867-20-3) → 2-[1-Amino-eth-(E)-ylidene]-4-cyano-pentanedioic acid 5-butyl ester 1-ethyl ester

Conditions	Yield
In benzene

n-butyl cyanoacrylate (6606-65-1) + ethyl 3-methylaminocrotonate (870-85-9) → 2-Cyano-4-[1-methylamino-eth-(E)-ylidene]-pentanedioic acid 1-butyl ester 5-ethyl ester

Conditions	Yield
In benzene

n-butyl cyanoacrylate (6606-65-1) + ethyl 3-ethylamino-2-butenoate (13070-53-6) → 2-Cyano-4-[1-ethylamino-eth-(E)-ylidene]-pentanedioic acid 1-butyl ester 5-ethyl ester

Conditions	Yield
In benzene

n-butyl cyanoacrylate (6606-65-1) + ethyl 3-anilinocrotonate (6287-35-0) → 2-Cyano-4-[1-phenylamino-eth-(E)-ylidene]-pentanedioic acid 1-butyl ester 5-ethyl ester (71161-02-9)

Conditions	Yield
In benzene

n-butyl cyanoacrylate (6606-65-1) + ethyl 3-(benzylamino)crotonate (1020-67-3) → 2-[1-Benzylamino-eth-(E)-ylidene]-4-cyano-pentanedioic acid 5-butyl ester 1-ethyl ester (71160-98-0)

Conditions	Yield
In benzene

n-butyl cyanoacrylate (6606-65-1) + benzyl-β-aminocrotonate (43107-11-5) → 2-[1-Amino-eth-(E)-ylidene]-4-cyano-pentanedioic acid 1-benzyl ester 5-butyl ester

Conditions	Yield
In benzene

n-butyl cyanoacrylate (6606-65-1) + methyl 3-aminocrotonate (14205-39-1) → 2-[1-Amino-eth-(E)-ylidene]-4-cyano-pentanedioic acid 5-butyl ester 1-methyl ester

Conditions	Yield
In benzene

n-butyl cyanoacrylate (6606-65-1) → polybutylcyanoacrylate, nanoparticles: size 290.4, polydispersity index 0.015; Monomer(s): butylcyanoacrylate

Conditions	Yield
With D-glucose; citric acid; dextran pH=3;

n-butyl cyanoacrylate (6606-65-1) → poly(n-butyl cyanoacrylate), anionic emulsion polymerization; monomer(s): n-butyl cyanoacrylate

Conditions	Yield
With dodecylbenzene-sulphonic acid In water at 25℃; pH=2;

n-butyl cyanoacrylate (6606-65-1) + dextran, Mw = 71 kDa → poly(n-butyl 2-cyanoacrylate)-dextran block copolymer

Conditions	Yield
With ammonium cerium(IV) nitrate; nitric acid at 40℃; pH=1;

n-butyl cyanoacrylate (6606-65-1) + poly(methyl methacrylate) → poly(methyl methacrylate); poly(n-butyl cyanoacrylate); mixture of

Conditions	Yield
With sulfur dioxide; hydroquinone at 20℃;

n-butyl cyanoacrylate (6606-65-1) → Reaxys ID: 15739938

Conditions	Yield
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 + n-butyl cyanoacrylate (6606-65-1) → poly[(n-butyl cyanoacrylate)-co-(2-octyl cyanoacrylate)]

Conditions	Yield
With hydrogenchloride; poly(ethylene oxide)-poly(propylene oxide)-poly(ethylene oxide) In water at 25℃; for 18h;

n-butyl cyanoacrylate (6606-65-1) → poly(n-butyl cyanoacrylate)

Conditions	Yield
at 60℃; for 5h;
With hydrogenchloride; dextran 70 In water for 4h;

n-butyl cyanoacrylate (6606-65-1) + doxorubicin hydrochloride (25316-40-9) → doxorubicin nanoparticles

Conditions	Yield
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) → poly(butylcyanoacrylate) nanoparticles

Conditions	Yield
With hydrogenchloride; fluoresceine isothiocyanate-dextran 70.000; dextran 70 In water at 20℃; for 4h;

formaldehyd (50-00-0) + n-butyl cyanoacrylate (6606-65-1) → 1,4-diammoniocyclohexane di-p-toluenesulfonate (16115-57-4)

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

Upstream product

• 5459-58-5 cyanoacetic acid butyl ester 
• 50-00-0 formaldehyd 
• 628-51-3 diacetoxymethane 
• 2568-90-3 di-n-butyloxymethane 
• 7085-85-0 ethyl-2-cyanoacrilate 
• 71-36-3 butan-1-ol 
• 105-56-6 ethyl 2-cyanoacetate 

Downstream Products

• 71160-96-8 2-[1-Benzylamino-eth-(E)-ylidene]-4-cyano-pentanedioic acid 5-butyl ester 1-methyl ester 
• 71161-00-7 2-[1-Benzylamino-eth-(E)-ylidene]-4-cyano-pentanedioic acid 1-benzyl ester 5-butyl ester 
• 71160-98-0 2-[1-Benzylamino-eth-(E)-ylidene]-4-cyano-pentanedioic acid 5-butyl ester 1-ethyl ester 
• 16115-57-4 1,4-diammoniocyclohexane di-p-toluenesulfonate 

Relevant articles and documents

N-butyl cyanoacrylate synthesis. A new quality step using microwaves

Alkyl cyanoacrylates are interesting products for use in industry because of their properties enabling them to stick together a wide range of substrates. n-Butyl cyanoacrylate is one of the most successfully used tissue adhesives in the field of medicine because it exhibits bacteriostatic and haemostatic characteristics, in addition to its adhesive properties. At present, its synthesis is performed with good yields via Knoevenagel condensation using conventional sources of heating, but this requires a long processing time. The aim of this work was to look for a new way of synthesising n-butyl cyanoacrylate using microwave irradiation as the source of heating. This non-conventional source of heating most likely reduces the process time of the synthesis. In comparison with a conventional heating source, such as an oil bath, the results showed the advantages of this method whereby the n-butyl cyanoacrylate gave the same yield and quality with a reduction in the reaction time by a factor of 3-5-fold.

Synthesis process of alpha-n-butyl cyanoacrylate

The invention provides a synthesis process of alpha-n-butyl cyanoacrylate. The synthesis process comprises the following steps: reacting formaldehyde and n-butyl cyanoacetate under the action of a catalyst and a catalyst assistant to obtain a wet prepolymer; and sequentially carrying out cracking and refining on the wet prepolymer to obtain the alpha-n-butyl cyanoacrylate. By adopting the synergistic effect of a composite additive and a dispersing agent, reaction time is greatly shortened, yield is obviously increased, an oil phase and a water phase are fully mixed under the condition of no solvent reaction, interface contact is expanded, product quality is improved, product purity is greater than or equal to 99.5%, and product yield is greater than or equal to 75%.

Synthesis method of alpha-cyanoacrylate

The invention provides a preparation method of alpha-cyanoacrylate. The method comprises steps as follows: alpha-cyanoacetate and paraformaldehyde or a formaldehyde water solution are subjected to a condensation reaction through programmed temperature and sufficient stirring under the condition of reduced pressure in the presence of a catalyst; water is removed after the condensation reaction ends, a polymerization inhibitor is added for distillation cracking after sufficient dewatering, sufficient stirring, vacuum pumping and temperature increasing are performed, and a cracking reaction is performed. A crude monomer obtained through the steps is rectified, and a refined alpha-cyanoacrylate monomer with higher yield and purity can be obtained. The polycondensation catalyst is a compound catalyst of triphenylphosphine and a guanidine catalyst. The method is high in efficiency and safety, has low side reactions and is environmentally friendly, and the product yield and the product purityare high.