Welcome to LookChem.com Sign In|Join Free

CAS

  • or

5459-58-5

Post Buying Request

5459-58-5 Suppliers

Recommended suppliersmore

  • Product
  • FOB Price
  • Min.Order
  • Supply Ability
  • Supplier
  • Contact Supplier

5459-58-5 Usage

Chemical Properties

Clear liquid

Uses

Butyl cyanoacetate is used as intermediate for numerous organic syntheses, e.g. alpha-cyanoacrylic adhesives. Product Data Sheet

General Description

tert-Butyl cyanoacetate undergoes alkylation with many substituted benzyl and heteroalyl alcohols to form the corressponding alpha-alkylated products.

Check Digit Verification of cas no

The CAS Registry Mumber 5459-58-5 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 5,4,5 and 9 respectively; the second part has 2 digits, 5 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 5459-58:
(6*5)+(5*4)+(4*5)+(3*9)+(2*5)+(1*8)=115
115 % 10 = 5
So 5459-58-5 is a valid CAS Registry Number.
InChI:InChI=1/C7H11NO2/c1-2-3-6-10-7(9)4-5-8/h2-4,6H2,1H3

5459-58-5SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name n-Butyl cyanoacetate

1.2 Other means of identification

Product number -
Other names Acetic acid, cyano-, butyl ester

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:5459-58-5 SDS

5459-58-5Synthetic route

cyanoacetic acid
372-09-8

cyanoacetic acid

butan-1-ol
71-36-3

butan-1-ol

cyanoacetic acid butyl ester
5459-58-5

cyanoacetic acid butyl ester

Conditions
ConditionsYield
With sulfuric acid; acetonitrile at 80 - 85℃; for 16 - 18h;95%
With sulfuric acid unter Entfernen des entstehenden Wassers;
With potassium hydroxide
cyanoacetic acid
372-09-8

cyanoacetic acid

cyanoacetic acid butyl ester
5459-58-5

cyanoacetic acid butyl ester

Conditions
ConditionsYield
With zinc perchlorate; magnesium sulfate In butan-1-ol at 80℃;77%
malononitrile
109-77-3

malononitrile

butan-1-ol
71-36-3

butan-1-ol

A

cyanoacetic acid butyl ester
5459-58-5

cyanoacetic acid butyl ester

B

di-n-butyl malonate
1190-39-2

di-n-butyl malonate

Conditions
ConditionsYield
With boron trifluoride diethyl etherate for 21h; Heating;A 75%
B 20%
butyl chloroacetate
590-02-3

butyl chloroacetate

sodium cyanide
143-33-9

sodium cyanide

cyanoacetic acid butyl ester
5459-58-5

cyanoacetic acid butyl ester

Conditions
ConditionsYield
With water; acetic acid at 95 - 100℃;
ethyl 2-cyanoacetate
105-56-6

ethyl 2-cyanoacetate

butan-1-ol
71-36-3

butan-1-ol

cyanoacetic acid butyl ester
5459-58-5

cyanoacetic acid butyl ester

Conditions
ConditionsYield
With potassium fluoride
Stage #1: ethyl 2-cyanoacetate; butan-1-ol In nitromethane at 105℃; for 0.5h;
Stage #2: With ytterbium(III) triflate In nitromethane; acetonitrile
With ytterbium(III) triflate at 100℃; for 8.5h;
With tetrabutyl titanate for 3h; Reflux;
1-bromo-butane
109-65-9

1-bromo-butane

cyanoacetic acid
372-09-8

cyanoacetic acid

cyanoacetic acid butyl ester
5459-58-5

cyanoacetic acid butyl ester

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In benzene
cyanoacetic acid butyl ester
5459-58-5

cyanoacetic acid butyl ester

5-Nitrosalicylaldehyde
97-51-8

5-Nitrosalicylaldehyde

2-amino-4-(butoxycarbonyl-cyano-methyl)-6-nitro-4H-chromene-3-carboxylic acid butyl ester

2-amino-4-(butoxycarbonyl-cyano-methyl)-6-nitro-4H-chromene-3-carboxylic acid butyl ester

Conditions
ConditionsYield
potassium-exchanged zirconium hydrogen phosphate at 40℃; for 1h;98%
cyanoacetic acid butyl ester
5459-58-5

cyanoacetic acid butyl ester

ortho-anisaldehyde
135-02-4

ortho-anisaldehyde

(E)-2-Cyano-3-(2-methoxy-phenyl)-acrylic acid butyl ester

(E)-2-Cyano-3-(2-methoxy-phenyl)-acrylic acid butyl ester

Conditions
ConditionsYield
With Merrifields's resin-bound piperazine In ethanol for 2h; Condensation; Heating;96%
cyanoacetic acid butyl ester
5459-58-5

cyanoacetic acid butyl ester

2-hydroxy-5-methylbenzaldehyde
613-84-3

2-hydroxy-5-methylbenzaldehyde

2-amino-4-(butoxycarbonyl-cyano-methyl)-6-methyl-4H-chromene-3-carboxylic acid butyl ester

2-amino-4-(butoxycarbonyl-cyano-methyl)-6-methyl-4H-chromene-3-carboxylic acid butyl ester

Conditions
ConditionsYield
potassium-exchanged zirconium hydrogen phosphate at 40℃; for 2h;96%
cyanoacetic acid butyl ester
5459-58-5

cyanoacetic acid butyl ester

butan-1-ol
71-36-3

butan-1-ol

butyl 2-cyanohexanoate

butyl 2-cyanohexanoate

Conditions
ConditionsYield
With triphenylphosphine; [IrCl(coe)2]2 In para-xylene at 130℃; for 15h;96%
cyanoacetic acid butyl ester
5459-58-5

cyanoacetic acid butyl ester

(E)-1-phenyl-3-(2-(phenylethynyl)phenyl)prop-2-en-1-one
1307781-72-1

(E)-1-phenyl-3-(2-(phenylethynyl)phenyl)prop-2-en-1-one

(Z)-butyl 1-benzylidene-2-cyano-3-(2-oxo-2-phenylethyl)-2,3-dihydro-1H-indene-2-carboxylate

(Z)-butyl 1-benzylidene-2-cyano-3-(2-oxo-2-phenylethyl)-2,3-dihydro-1H-indene-2-carboxylate

Conditions
ConditionsYield
With caesium carbonate In acetonitrile at 20℃; for 3h; stereoselective reaction;96%
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

2-(2-bromo-5-chloro-phenyl)-1H-benzoimidazole
14225-85-5

2-(2-bromo-5-chloro-phenyl)-1H-benzoimidazole

C20H18ClN3O2
1301148-87-7

C20H18ClN3O2

Conditions
ConditionsYield
With copper(l) iodide; potassium carbonate; pipecolic Acid In dimethyl sulfoxide at 80℃; for 12h; Inert atmosphere;95%
cyanoacetic acid butyl ester
5459-58-5

cyanoacetic acid butyl ester

3-(N-methyl-N-benzylamino)prop-2-enal
63271-09-0

3-(N-methyl-N-benzylamino)prop-2-enal

n-butyl 2-chloronicotinate
256444-57-2

n-butyl 2-chloronicotinate

Conditions
ConditionsYield
Stage #1: cyanoacetic acid butyl ester; 3-(N-methyl-N-benzylamino)prop-2-enal With 1-hexyl-3-methylimidazol-1-ium chloride at 160℃; for 1h; Microwave irradiation;
Stage #2: With hydrogenchloride
94.1%
Stage #1: cyanoacetic acid butyl ester; 3-(N-methyl-N-benzylamino)prop-2-enal With sodium ethanolate at 100℃; Sonication;
Stage #2: With hydrogenchloride at 100℃; for 0.583333h; Sonication;
91.1%
n-heptan1ol
111-70-6

n-heptan1ol

cyanoacetic acid butyl ester
5459-58-5

cyanoacetic acid butyl ester

butyl 2-cyanonanoate

butyl 2-cyanonanoate

Conditions
ConditionsYield
With triphenylphosphine; bis(1,5-cyclooctadiene)diiridium(I) dichloride In para-xylene at 130℃; for 15h;94%
cyanoacetic acid butyl ester
5459-58-5

cyanoacetic acid butyl ester

3-(N,N-diethylamino)propenal
13070-22-9

3-(N,N-diethylamino)propenal

5-(N,N-diethyl)amino-2-cyano-2,4-pentadienoic acid butyl ester

5-(N,N-diethyl)amino-2-cyano-2,4-pentadienoic acid butyl ester

Conditions
ConditionsYield
With N-butyl-N-ethylpiperidinium chloride at 65℃; for 10h;93.1%
With sodium ethanolate at 100℃; Microwave irradiation;92.2%
With sodium ethanolate at 100℃; Sonication;90.7%
cyanoacetic acid butyl ester
5459-58-5

cyanoacetic acid butyl ester

meta-hydroxybenzaldehyde
100-83-4

meta-hydroxybenzaldehyde

(E)-2-Cyano-3-(3-hydroxy-phenyl)-acrylic acid butyl ester

(E)-2-Cyano-3-(3-hydroxy-phenyl)-acrylic acid butyl ester

Conditions
ConditionsYield
With Merrifields's resin-bound piperazine In ethanol for 2h; Condensation; Heating;93%
cyanoacetic acid butyl ester
5459-58-5

cyanoacetic acid butyl ester

2-Benzyloxyethanol
622-08-2

2-Benzyloxyethanol

C16H21NO3

C16H21NO3

Conditions
ConditionsYield
With triphenylphosphine; [IrCl(coe)2]2 In para-xylene at 130℃; for 15h;93%
RuH*C2H4*2P(C6H5)3*P(C6H5)2(C6H4)=RuH(C2H4)(P(C6H5)3)2(P(C6H5)2C6H4)

RuH*C2H4*2P(C6H5)3*P(C6H5)2(C6H4)=RuH(C2H4)(P(C6H5)3)2(P(C6H5)2C6H4)

cyanoacetic acid butyl ester
5459-58-5

cyanoacetic acid butyl ester

mer-hydrido[[(butoxycarbonyl)methyl]cyano](butyl cyanoacetate)tris(triphenylphosphine)ruthenium(II)
173593-97-0

mer-hydrido[[(butoxycarbonyl)methyl]cyano](butyl cyanoacetate)tris(triphenylphosphine)ruthenium(II)

Conditions
ConditionsYield
In tetrahydrofuran byproducts: C2H4; room temp., 6 h; washing (hexane), recrystallization (THF/hexane); elem. anal.;93%
cyanoacetic acid butyl ester
5459-58-5

cyanoacetic acid butyl ester

5-bromo-3-methoxysalicylaldehyde
5034-74-2

5-bromo-3-methoxysalicylaldehyde

2-amino-6-bromo-4-(butoxycarbonyl-cyano-methyl)-8-methoxy-4H-chromene-3-carboxylic acid butyl ester

2-amino-6-bromo-4-(butoxycarbonyl-cyano-methyl)-8-methoxy-4H-chromene-3-carboxylic acid butyl ester

Conditions
ConditionsYield
potassium-exchanged zirconium hydrogen phosphate at 40℃; for 3h;91%
cyanoacetic acid butyl ester
5459-58-5

cyanoacetic acid butyl ester

5-bromosalicyclaldehyde
1761-61-1

5-bromosalicyclaldehyde

2-amino-6-bromo-4-(butoxycarbonyl-cyano-methyl)-4H-chromene-3-carboxylic acid butyl ester

2-amino-6-bromo-4-(butoxycarbonyl-cyano-methyl)-4H-chromene-3-carboxylic acid butyl ester

Conditions
ConditionsYield
potassium-exchanged zirconium hydrogen phosphate at 40℃; for 3h;91%
cyanoacetic acid butyl ester
5459-58-5

cyanoacetic acid butyl ester

2-phenylethanol
60-12-8

2-phenylethanol

C15H19NO2

C15H19NO2

Conditions
ConditionsYield
With triphenylphosphine; bis(1,5-cyclooctadiene)diiridium(I) dichloride In para-xylene at 130℃; for 15h;91%
2-methoxy-ethanol
109-86-4

2-methoxy-ethanol

cyanoacetic acid butyl ester
5459-58-5

cyanoacetic acid butyl ester

butyl 2-cyano-4-methoxybutanoate

butyl 2-cyano-4-methoxybutanoate

Conditions
ConditionsYield
With triphenylphosphine; bis(1,5-cyclooctadiene)diiridium(I) dichloride In para-xylene at 130℃; for 15h;91%
cyanoacetic acid butyl ester
5459-58-5

cyanoacetic acid butyl ester

butan-1-ol
71-36-3

butan-1-ol

cyanoacetic acid amide
107-91-5

cyanoacetic acid amide

Conditions
ConditionsYield
With sodium methylate In methanol91%
cyanoacetic acid butyl ester
5459-58-5

cyanoacetic acid butyl ester

propionaldehyde
123-38-6

propionaldehyde

butyl α-cyano-α-pentenoate
184765-51-3

butyl α-cyano-α-pentenoate

Conditions
ConditionsYield
With zinc(II) acetate dihydrate In methanol at 70℃; for 2h; Temperature; Reflux;90.9%
cyanoacetic acid butyl ester
5459-58-5

cyanoacetic acid butyl ester

5-nitro-2-(1-pyrrolidinyl)-benzaldehyde
30742-59-7

5-nitro-2-(1-pyrrolidinyl)-benzaldehyde

(E)-2-Cyano-3-(5-nitro-2-pyrrolidin-1-yl-phenyl)-acrylic acid butyl ester
135097-64-2

(E)-2-Cyano-3-(5-nitro-2-pyrrolidin-1-yl-phenyl)-acrylic acid butyl ester

Conditions
ConditionsYield
In toluene for 2h; Ambient temperature;90%
cyanoacetic acid butyl ester
5459-58-5

cyanoacetic acid butyl ester

6-nitro-1,3-benzodioxole-5-carbaldehyde
712-97-0

6-nitro-1,3-benzodioxole-5-carbaldehyde

(E)-2-Cyano-3-(6-nitro-benzo[1,3]dioxol-5-yl)-acrylic acid butyl ester

(E)-2-Cyano-3-(6-nitro-benzo[1,3]dioxol-5-yl)-acrylic acid butyl ester

Conditions
ConditionsYield
With potassium fluoride on basic alumina In ethanol at 30℃;90%
2-Hydroxy-4-methoxybenzaldehyde
673-22-3

2-Hydroxy-4-methoxybenzaldehyde

cyanoacetic acid butyl ester
5459-58-5

cyanoacetic acid butyl ester

2-amino-4-(butoxycarbonyl-cyano-methyl)-7-methoxy-4H-chromene-3-carboxylic acid butyl ester

2-amino-4-(butoxycarbonyl-cyano-methyl)-7-methoxy-4H-chromene-3-carboxylic acid butyl ester

Conditions
ConditionsYield
potassium-exchanged zirconium hydrogen phosphate at 40℃; for 6h;89%
cyanoacetic acid butyl ester
5459-58-5

cyanoacetic acid butyl ester

C8H7BrN4
1252046-09-5

C8H7BrN4

butyl 1,3-diamino-6-methylisoquinoline-4-carboxylate
1452837-91-0

butyl 1,3-diamino-6-methylisoquinoline-4-carboxylate

Conditions
ConditionsYield
With copper(l) iodide; water; potassium carbonate; pipecolic Acid In N,N-dimethyl-formamide at 80℃; for 24h; Inert atmosphere;89%
cyanoacetic acid butyl ester
5459-58-5

cyanoacetic acid butyl ester

butyraldehyde
123-72-8

butyraldehyde

butyl α-cyano-α-hexenoate
184765-62-6

butyl α-cyano-α-hexenoate

Conditions
ConditionsYield
With zinc(II) acetate dihydrate In methanol at 70℃; for 2h; Temperature;88.1%
cyanoacetic acid butyl ester
5459-58-5

cyanoacetic acid butyl ester

3-methoxy-2-hydroxybenzaldehyde
148-53-8

3-methoxy-2-hydroxybenzaldehyde

2-amino-4-(butoxycarbonyl-cyano-methyl)-8-methoxy-4H-chromene-3-carboxylic acid butyl ester

2-amino-4-(butoxycarbonyl-cyano-methyl)-8-methoxy-4H-chromene-3-carboxylic acid butyl ester

Conditions
ConditionsYield
potassium-exchanged zirconium hydrogen phosphate at 40℃; for 2h;87%
cyanoacetic acid butyl ester
5459-58-5

cyanoacetic acid butyl ester

2-bromo-N-(2-bromophenyl)-benzamide

2-bromo-N-(2-bromophenyl)-benzamide

C20H18N2O3
1236814-01-9

C20H18N2O3

Conditions
ConditionsYield
With sodium carbonate; copper(l) chloride In dimethyl sulfoxide at 60℃; for 12h; Ullmann type coupling; Inert atmosphere;87%
cyanoacetic acid butyl ester
5459-58-5

cyanoacetic acid butyl ester

2-nitro-benzaldehyde
552-89-6

2-nitro-benzaldehyde

(E)-2-Cyano-3-(2-nitro-phenyl)-acrylic acid butyl ester

(E)-2-Cyano-3-(2-nitro-phenyl)-acrylic acid butyl ester

Conditions
ConditionsYield
With potassium fluoride on basic alumina In ethanol at 30℃;86%
cyanoacetic acid butyl ester
5459-58-5

cyanoacetic acid butyl ester

C14H9BrCl2N2
1301148-94-6

C14H9BrCl2N2

C21H19Cl2N3O2
1301148-91-3

C21H19Cl2N3O2

Conditions
ConditionsYield
With copper(l) iodide; potassium carbonate; pipecolic Acid In dimethyl sulfoxide at 60℃; for 12h; Inert atmosphere;86%
cyanoacetic acid butyl ester
5459-58-5

cyanoacetic acid butyl ester

2-(2-bromophenyl)-1H-perimidine

2-(2-bromophenyl)-1H-perimidine

n-butyl 13-aminoisoquinolino[2,1-a]perimidine-12-carboxylate

n-butyl 13-aminoisoquinolino[2,1-a]perimidine-12-carboxylate

Conditions
ConditionsYield
With copper(l) iodide; sodium hydrogencarbonate; L-proline In N,N-dimethyl-formamide at 60℃; Inert atmosphere; chemoselective reaction;86%

5459-58-5Relevant articles and documents

Insight into the isoelectronic character of azomethines and vinylenes using representative models: A spectroscopic and electrochemical study

Bolduc, Andreanne,Al Ouahabi, Abelaziz,Mallet, Charlotte,Skene

, p. 9258 - 9269 (2013)

A series of azomethine and vinylene dyad and triad analogues were prepared. Their absorbance, fluorescence, and redox properties were examined experimentally and theoretically using density functional theory (DFT) calculations. These measurements were done to determine the effect of the heteroatom of the azomethine relative to its all-carbon counterpart and to assess the isoelectronic character of the two bonds. The orientation of the azomethine was found to have little effect on the absorbance, fluorescence, and electrochemical properties. In contrast, the spectral and electrochemical properties were highly contingent on the electronic groups and degree of conjugation. The spectral properties could be tuned 200 nm across the visible region. More importantly, the heteroatom in the conjugated bond was found to give rise to only a 20 nm bathochromic shift in the absorbance and fluorescence spectra. The fluorescence quantum yield (ΦFl) of the vinylene derivatives varied between 5% and 20% with fluorescence quenching occurring by photoisomerization from the E to Z isomers. In contrast, the fluorescence of the analogous azomethine derivatives was completely quenched. The collective spectroscopic and electrochemical ab initio DFT data additionally confirmed that the azomethine and its analogous vinylene are isoelectronic. It was also found that a conjugated thiophene vinylene dyad with primary amines in the α,α′-positions could be prepared and isolated. The compound was stable under aerobic conditions providing electron withdrawing (either ester or nitrile) groups were located in the adjacent positions.

PROCESS FOR PREPARING ELECTRON DEFICIENT OLEFIN PRECURSORS

-

Paragraph 0045, (2018/07/29)

This invention relates to a process for producing electron deficient olefin precursors, such as 2-cyanoacetates, using an acid catalyzed transesterification reaction.

Magnetically recoverable AlFe/Te nanocomposite as a new catalyst for the facile esterification reaction under neat conditions

Alavi, Seyed Jamal,Sadeghian, Hamid,Seyedi, Seyed Mohammad,Eshghi, Hossein,Salimi, Alireza

, (2017/11/23)

In this work, a new Fe3O4/AlFe/Te nanocomposite was synthesized by a one-step sol–gel method. The Fe3O4 magnetic nanoparticles (MNPs) were prepared and then mixed with aluminum telluride (Al2Te3) in an alkali medium to produce the desired catalyst. After characterization of the Fe3O4/AlFe/Te nanocomposite by SEM, TEM, EDS, XRD, and ICP analyses, it was used in the esterification reaction. This heterogeneous catalyst showed high catalytic activity in the esterification of commercially available carboxylic acids with various alcohols to produce the desired esters at high conversions under neat conditions. The Fe3O4/AlFe/Te nanocomposites were separated from the reaction mixture via an external magnet and re-used 8 times without significant loss of catalytic activity.

Post a RFQ

Enter 15 to 2000 letters.Word count: 0 letters

Attach files(File Format: Jpeg, Jpg, Gif, Png, PDF, PPT, Zip, Rar,Word or Excel Maximum File Size: 3MB)

1

What can I do for you?
Get Best Price

Get Best Price for 5459-58-5