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97-96-1

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97-96-1 Usage

Description

2-Ethylbutyraldehyde is a colorless liquid with a pungent odor. It is less dense than water, insoluble in water, and has a flash point of 70°F. This organic compound is known for its green, fruity, and cocoa-like taste with sweet and fresh nuances, which can be detected at a threshold value of 20 ppm. It is found naturally in various food items such as melon, French fried potatoes, wheaten bread, scallops, citrus fruits, white bread, and maize.

Uses

Used in Chemical Synthesis:
2-Ethylbutyraldehyde is used as an intermediate in organic synthesis for the production of various chemicals and pharmaceuticals. Its reactivity and unique structure make it a valuable component in the synthesis of complex organic molecules.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2-Ethylbutyraldehyde is used as a building block for the synthesis of drugs. Its ability to form aldoximes using aqueous hydroxylamine makes it a key precursor in the preparation of certain pharmaceutical compounds.
Used in Rubber Industry:
2-Ethylbutyraldehyde is used as a rubber accelerator, enhancing the rate of vulcanization and improving the overall properties of rubber products. This application is crucial for the manufacturing of tires, automotive parts, and other rubber-based items.
Used in Synthetic Resins:
In the production of synthetic resins, 2-Ethylbutyraldehyde serves as a vital component. These resins are used in a wide range of applications, including coatings, adhesives, and composite materials.
Used in Flavor and Fragrance Industry:
Due to its distinct green, fruity, cocoa, sweet, and fresh taste characteristics, 2-Ethylbutyraldehyde is used in the flavor and fragrance industry to create and enhance various scents and flavors in food, beverages, and cosmetics.

Air & Water Reactions

Highly flammable. With air slowly form peroxides. Insoluble in water.

Reactivity Profile

2-ETHYLBUTYRALDEHYDE is an aldehyde. Aldehydes are frequently involved in self-condensation or polymerization reactions. These reactions are exothermic; they are often catalyzed by acid. Aldehydes are readily oxidized to give carboxylic acids. Flammable and/or toxic gases are generated by the combination of aldehydes with azo, diazo compounds, dithiocarbamates, nitrides, and strong reducing agents. Aldehydes can react with air to give first peroxo acids, and ultimately carboxylic acids. These autoxidation reactions are activated by light, catalyzed by salts of transition metals, and are autocatalytic (catalyzed by the products of the reaction). The addition of stabilizers (antioxidants) to shipments of aldehydes retards autoxidation.

Hazard

Irritant to eyes and skin. Flammable, dangerous fire risk.

Health Hazard

May cause toxic effects if inhaled or absorbed through skin. Inhalation or contact with material may irritate or burn skin and eyes. Fire will produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or suffocation. Runoff from fire control or dilution water may cause pollution.

Fire Hazard

HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. Vapors may form explosive mixtures with air. Vapors may travel to source of ignition and flash back. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapor explosion hazard indoors, outdoors or in sewers. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids are lighter than water.

Safety Profile

Moderately toxic by ingestion. Mildly toxic by inhalation. A skin irritant. Flammable liquid. Can react vigorously with oxidizing materials. To fight fire, use alcohol foam, Co2, dry chemical. When heated to decomposition it emits acrid smoke and fumes. See also ALDEHYDES.

Synthesis

From diethyl carbinol and anhydrous oxalic acid or with sulfuric acid; a more recent synthetic route (Xeisel–Neuwirth method) calls for the reduction of α-vinylcrotonaldehyde using iron dust and acetic acid

Potential Exposure

Used in organic synthesis of pharmaceuticals and rubber chemicals.

Shipping

UN1178 2-Ethyl butyraldehyde, Hazard Class: 3; Labels: 3-Flammable liquid

Incompatibilities

Vapors may form explosive mixture with air. Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, epoxides, and reducing agents. Aldehydes are frequently involved in self-condensation or polymerization reactions. These reactions are exothermic; they are often catalyzed by acid. Aldehydes are readily oxidized to give carboxylic acids. Flammable and/or toxic gases are generated by the combination of aldehydes with azo, diazo compounds, dithiocarbamates, nitrides, and strong reducing agents. Aldehydes can react with air to give first peroxo acids, and ultimately carboxylic acids. These autoxidation reactions are activated by light, catalyzed by salts of transition metals, and are autocatalytic (catalyzed by the products of the reaction). The addition of stabilizers (antioxidants) to shipments of aldehydes retards autoxidation

Check Digit Verification of cas no

The CAS Registry Mumber 97-96-1 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 9 and 7 respectively; the second part has 2 digits, 9 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 97-96:
(4*9)+(3*7)+(2*9)+(1*6)=81
81 % 10 = 1
So 97-96-1 is a valid CAS Registry Number.
InChI:InChI=1/C6H12O/c1-3-6(4-2)5-7/h5-6H,3-4H2,1-2H3

97-96-1 Well-known Company Product Price

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  • Alfa Aesar

  • (B23465)  2-Ethylbutyraldehyde, 98%   

  • 97-96-1

  • 250ml

  • 1138.0CNY

  • Detail
  • Alfa Aesar

  • (B23465)  2-Ethylbutyraldehyde, 98%   

  • 97-96-1

  • 1000ml

  • 3221.0CNY

  • Detail

97-96-1SDS

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 2-Ethylbutyraldehyde

1.2 Other means of identification

Product number -
Other names 2-ethylbutanal

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Food additives -> Flavoring Agents
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:97-96-1 SDS

97-96-1Synthetic route

1,1-diacetoxy-2-ethyl-butane
845791-28-8

1,1-diacetoxy-2-ethyl-butane

2-Ethylbutyraldehyde
97-96-1

2-Ethylbutyraldehyde

Conditions
ConditionsYield
With 2,6-dicarboxypyridinium chlorochromate In acetonitrile at 20℃; for 0.25h;96%
N-(Benzylidene)-2-ethyl-1-butenylamine
74947-34-5

N-(Benzylidene)-2-ethyl-1-butenylamine

A

2-Ethylbutyraldehyde
97-96-1

2-Ethylbutyraldehyde

B

benzaldehyde
100-52-7

benzaldehyde

Conditions
ConditionsYield
With hydrogenchloride In dichloromethane for 1h; Heating;A 93%
B n/a
N-(4-Chlorobenzylidene)-2-ethyl-1-butenylamine
143399-67-1

N-(4-Chlorobenzylidene)-2-ethyl-1-butenylamine

A

2-Ethylbutyraldehyde
97-96-1

2-Ethylbutyraldehyde

B

4-chlorobenzaldehyde
104-88-1

4-chlorobenzaldehyde

Conditions
ConditionsYield
With hydrogenchloride In dichloromethane for 1h; Heating;A 87%
B n/a
HOCEt2CH2OMe
3587-67-5

HOCEt2CH2OMe

2-Ethylbutyraldehyde
97-96-1

2-Ethylbutyraldehyde

Conditions
ConditionsYield
With phosphoric acid at 100℃; for 3h;78%
carbon monoxide
201230-82-2

carbon monoxide

2-pentene
109-68-2

2-pentene

A

2-Ethylbutyraldehyde
97-96-1

2-Ethylbutyraldehyde

B

2-methylvaleraldehyde
123-15-9

2-methylvaleraldehyde

C

hexanal
66-25-1

hexanal

Conditions
ConditionsYield
With hydrogen In methoxybenzene at 120℃; under 37503 Torr; for 6h; Product distribution; Further Variations:; Reagents; Pressures; Temperatures;A n/a
B n/a
C 20%
5,5-diethyl-3-nitroso-oxazolidin-2-one
64468-90-2

5,5-diethyl-3-nitroso-oxazolidin-2-one

2-Ethylbutyraldehyde
97-96-1

2-Ethylbutyraldehyde

Conditions
ConditionsYield
With potassium hydroxide
(E)-2-ethyl-2-butenal
63883-69-2

(E)-2-ethyl-2-butenal

2-Ethylbutyraldehyde
97-96-1

2-Ethylbutyraldehyde

Conditions
ConditionsYield
With ethanol; palladium Hydrogenation;
2-ethyl-1-butanol
97-95-0

2-ethyl-1-butanol

A

2-Ethylbutyraldehyde
97-96-1

2-Ethylbutyraldehyde

B

2-ethylbutyl 2-ethylbutanoate
55145-34-1

2-ethylbutyl 2-ethylbutanoate

Conditions
ConditionsYield
With copper chromite at 260℃;
2-ethyl-2-hydroxy-1-butanol
66553-16-0

2-ethyl-2-hydroxy-1-butanol

2-Ethylbutyraldehyde
97-96-1

2-Ethylbutyraldehyde

Conditions
ConditionsYield
With sulfuric acid
3-ethoxymethyl-pentan-3-ol
155950-22-4

3-ethoxymethyl-pentan-3-ol

2-Ethylbutyraldehyde
97-96-1

2-Ethylbutyraldehyde

Conditions
ConditionsYield
With sulfuric acid
2-vinyl-crotonaldehyde
20521-42-0

2-vinyl-crotonaldehyde

2-Ethylbutyraldehyde
97-96-1

2-Ethylbutyraldehyde

Conditions
ConditionsYield
With nickel diacetate; iron; acetic acid
2-ethylcrotonaldehyde
19780-25-7

2-ethylcrotonaldehyde

2-Ethylbutyraldehyde
97-96-1

2-Ethylbutyraldehyde

Conditions
ConditionsYield
With palladium 10% on activated carbon; hydrogen at 60℃; for 5h;
With nickel Hydrogenation;
3-ethoxymethyl-pentan-3-ol
155950-22-4

3-ethoxymethyl-pentan-3-ol

oxalic acid
144-62-7

oxalic acid

2-Ethylbutyraldehyde
97-96-1

2-Ethylbutyraldehyde

Conditions
ConditionsYield
at 110 - 115℃;
at 110 - 115℃;
1-phenoxy-2-ethyl-butanol-(2)
3587-63-1

1-phenoxy-2-ethyl-butanol-(2)

oxalic acid
144-62-7

oxalic acid

2-Ethylbutyraldehyde
97-96-1

2-Ethylbutyraldehyde

Conditions
ConditionsYield
at 110 - 115℃;
ethylmagnesium bromide
925-90-6

ethylmagnesium bromide

2-Chloro-N,N-diethylacetamide
2315-36-8

2-Chloro-N,N-diethylacetamide

A

2-Ethylbutyraldehyde
97-96-1

2-Ethylbutyraldehyde

B

3-diethylaminomethyl-pentan-3-ol
23590-25-2

3-diethylaminomethyl-pentan-3-ol

C

diethyl-(2-ethyl-but-2-enyl)-amine

diethyl-(2-ethyl-but-2-enyl)-amine

D

N,N-diethyl-2-diethylaminoacetamide
27794-54-3

N,N-diethyl-2-diethylaminoacetamide

ethyl bromide
74-96-4

ethyl bromide

α-bromobutyraldehyde diethyl acetal
3400-56-4

α-bromobutyraldehyde diethyl acetal

2-Ethylbutyraldehyde
97-96-1

2-Ethylbutyraldehyde

Conditions
ConditionsYield
(i) Mg, BrCH2CH2Br, Et2O, (ii) /BRN= 1209224/, (iii) aq. HCl, Et2O; Multistep reaction;
3-(methoxymethylene)pentane
1733-17-1

3-(methoxymethylene)pentane

2-Ethylbutyraldehyde
97-96-1

2-Ethylbutyraldehyde

Conditions
ConditionsYield
With perchloric acid In benzene
With hydrogen cation
With water; sodium chloride; hydrogenchloride at 25℃; Rate constant; isotope effects investigated;
2-ethyl-N,N-dimethyl-butyramide
31499-97-5

2-ethyl-N,N-dimethyl-butyramide

2-Ethylbutyraldehyde
97-96-1

2-Ethylbutyraldehyde

Conditions
ConditionsYield
With lithium diethoxyaluminum hydride In diethyl ether
but-1-enyl-butyl-isobutyl-amine
53516-59-9

but-1-enyl-butyl-isobutyl-amine

ethyl iodide
75-03-6

ethyl iodide

2-Ethylbutyraldehyde
97-96-1

2-Ethylbutyraldehyde

Conditions
ConditionsYield
In acetonitrile
(i) MeCN, (ii) aq. NaOAc, AcOH; Multistep reaction;
tris(ethylenedioxyboryl)methane
59278-44-3

tris(ethylenedioxyboryl)methane

pentan-3-one
96-22-0

pentan-3-one

2-Ethylbutyraldehyde
97-96-1

2-Ethylbutyraldehyde

Conditions
ConditionsYield
(i) MeLi, Et2O, THF, CH2Cl2, (ii) /BRN= 635749/, (iii) NaBO3*4H2O; Multistep reaction;
Yield given. Multistep reaction;
(E)-pent-2-ene
646-04-8

(E)-pent-2-ene

carbon monoxide
201230-82-2

carbon monoxide

A

2-Ethylbutyraldehyde
97-96-1

2-Ethylbutyraldehyde

B

2-methylvaleraldehyde
123-15-9

2-methylvaleraldehyde

Conditions
ConditionsYield
With hydrogen; cobaltcluster at 150℃; under 51154.1 - 57829.6 Torr; for 22.5h; Mechanism; Product distribution; determination of selectivity, velocity and decomposition of cluster; also with phosphanes; other temperatures, pressures and times;
With hydrogen; acetylacetonatodicarbonylrhodium(l) In dichloromethane at 120℃; under 15514.9 Torr; for 16h;
C13H17N2O3

C13H17N2O3

A

2-Ethylbutyraldehyde
97-96-1

2-Ethylbutyraldehyde

B

4-Nitrobenzonitrile radical anion
12402-47-0

4-Nitrobenzonitrile radical anion

Conditions
ConditionsYield
In water at 20℃; Rate constant; Thermodynamic data; ΔH++, ΔS++;
In water at 19.9℃; Rate constant; pH = 4 - 5;
2-chloro-2-ethylbutyraldehyde
57240-62-7

2-chloro-2-ethylbutyraldehyde

benzylamine
100-46-9

benzylamine

A

2-Ethylbutyraldehyde
97-96-1

2-Ethylbutyraldehyde

B

benzaldehyde
100-52-7

benzaldehyde

Conditions
ConditionsYield
multistep reaction; other substrates;
1-butylene
106-98-9

1-butylene

carbon monoxide
201230-82-2

carbon monoxide

A

2-Ethylbutyraldehyde
97-96-1

2-Ethylbutyraldehyde

B

pentanal
110-62-3

pentanal

Conditions
ConditionsYield
With acetylacetonatodicarbonylrhodium(l); hydrogen; (R,S)-binaphos In benzene at 60℃; under 76000 Torr; for 40h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
With acetylacetonatodicarbonylrhodium(l); hydrogen; (R,S)-binaphos In benzene at 60℃; under 76000 Torr; for 40h; Yields of byproduct given;
2-ethyl-1-butanol
97-95-0

2-ethyl-1-butanol

2-Ethylbutyraldehyde
97-96-1

2-Ethylbutyraldehyde

Conditions
ConditionsYield
With acetic acid; quinolinium chlorochromate(VI) at 19.85℃; Kinetics; Further Variations:; Temperatures; Oxidation;
hexanal
66-25-1

hexanal

A

2-Ethylbutyraldehyde
97-96-1

2-Ethylbutyraldehyde

B

2-methylvaleraldehyde
123-15-9

2-methylvaleraldehyde

Conditions
ConditionsYield
With 1-penten; η5-pentamethylcyclopentadienylbis(η2-propene)rhodium(I) In benzene at 80℃; for 5h; Isomerization;
oxalic acid
144-62-7

oxalic acid

-diethylcarbinol

-diethylcarbinol

2-Ethylbutyraldehyde
97-96-1

2-Ethylbutyraldehyde

Conditions
ConditionsYield
at 110 - 115℃;
diethyl ether
60-29-7

diethyl ether

2-pentene
109-68-2

2-pentene

carbon monoxide

carbon monoxide

hydrogen

hydrogen

CO2(CO)8-kieselguhr

CO2(CO)8-kieselguhr

A

2-Ethylbutyraldehyde
97-96-1

2-Ethylbutyraldehyde

B

2-methylvaleraldehyde
123-15-9

2-methylvaleraldehyde

Conditions
ConditionsYield
at 125℃; under 220652 Torr;
2-pentene
109-68-2

2-pentene

benzene
71-43-2

benzene

carbon monoxide

carbon monoxide

hydrogen

hydrogen

CO2(CO)8-kieselguhr

CO2(CO)8-kieselguhr

A

2-Ethylbutyraldehyde
97-96-1

2-Ethylbutyraldehyde

B

2-methylvaleraldehyde
123-15-9

2-methylvaleraldehyde

Conditions
ConditionsYield
at 125℃; under 220652 Torr;
2-Ethylbutyraldehyde
97-96-1

2-Ethylbutyraldehyde

3,6-diethyl-octane-4,5-diol

3,6-diethyl-octane-4,5-diol

Conditions
ConditionsYield
With phenyldimethylsilyl chloride; zinc; bis(cyclopentadienyl)vanadium dichloride In tetrahydrofuran at 20℃; for 13h; Reduction;100%
2-Ethylbutyraldehyde
97-96-1

2-Ethylbutyraldehyde

2-amino-5-chloro-α-(2'-chlorophenyl)benzyl alcohol
74067-45-1

2-amino-5-chloro-α-(2'-chlorophenyl)benzyl alcohol

[5-chloro-2-(2-ethyl-butylamino)-phenyl]-(2-chloro-phenyl)-methanol
152906-78-0

[5-chloro-2-(2-ethyl-butylamino)-phenyl]-(2-chloro-phenyl)-methanol

Conditions
ConditionsYield
With sodium cyanoborohydride; acetic acid In methanol at 20℃;100%
2-Ethylbutyraldehyde
97-96-1

2-Ethylbutyraldehyde

diethylzinc
557-20-0

diethylzinc

acetic anhydride
108-24-7

acetic anhydride

(+)-4-ethyl-3-hexyl acetate

(+)-4-ethyl-3-hexyl acetate

Conditions
ConditionsYield
Stage #1: 2-Ethylbutyraldehyde; diethylzinc With (Sp,S)-5-[C6H11-CH(Me)-N=C(Me)]-4-OH-[2.2]paracyclophane In hexane at 0℃; for 14h;
Stage #2: acetic anhydride In hexane at 20℃; for 24h; Further stages.;
100%
2-Ethylbutyraldehyde
97-96-1

2-Ethylbutyraldehyde

4-Phenyl-1-butyne
16520-62-0

4-Phenyl-1-butyne

3-ethyl-8-phenyl-oct-5-yn-4-ol

3-ethyl-8-phenyl-oct-5-yn-4-ol

Conditions
ConditionsYield
Stage #1: 4-Phenyl-1-butyne With zinc trifluoromethanesulfonate; triethylamine; (1S,2S)-2-N,N-dimethylamino-1-(p-nitrophenyl)-3-(tert-butyldimethylsilyloxy)propan-1-ol In toluene for 0.25h;
Stage #2: 2-Ethylbutyraldehyde In toluene at 25℃; for 2h; Further stages.;
99%
With (difluoromethanesulfonyloxy)zincio difluoromethanesulfonate; triethylamine; (1S,2S)-2-N,N-dimethylamino-1-(p-nitrophenyl)-3-(tert-butyldimethylsilyloxy)propan-1-ol In toluene at 25℃; for 2h;83%
2-Ethylbutyraldehyde
97-96-1

2-Ethylbutyraldehyde

phenylacetylene
536-74-3

phenylacetylene

4-ethyl-1-phenyl-hex-1-yn-3-ol

4-ethyl-1-phenyl-hex-1-yn-3-ol

Conditions
ConditionsYield
Stage #1: phenylacetylene With zinc trifluoromethanesulfonate; triethylamine; (1S,2S)-2-N,N-dimethylamino-1-(p-nitrophenyl)-3-(tert-butyldimethylsilyloxy)propan-1-ol In toluene for 0.25h;
Stage #2: 2-Ethylbutyraldehyde In toluene at 25℃; for 2h; Further stages.;
99%
With (difluoromethanesulfonyloxy)zincio difluoromethanesulfonate; triethylamine; (1S,2S)-2-N,N-dimethylamino-1-(p-nitrophenyl)-3-(tert-butyldimethylsilyloxy)propan-1-ol In toluene at 25℃; for 2h;89%
2-Ethylbutyraldehyde
97-96-1

2-Ethylbutyraldehyde

trimethylsilylacetylene
1066-54-2

trimethylsilylacetylene

dibenzylamine
103-49-1

dibenzylamine

(-)-N,N-dibenzyl-4-ethyl-1-(trimethylsilyl)hex-1-yn-3-amine
654678-64-5

(-)-N,N-dibenzyl-4-ethyl-1-(trimethylsilyl)hex-1-yn-3-amine

Conditions
ConditionsYield
With (R)-1-(2-(diphenylphosphanyl)naphthalen-1-yl)isoquinoline; 4 A molecular sieve; copper(I) bromide In toluene at 20℃;99%
With (R)-1-(2-(diphenylphosphanyl)naphthalen-1-yl)isoquinoline; 4 A molecular sieve; copper(I) bromide In decane; toluene at 20℃; for 144h;99%
With (R)-1-(2-(diphenylphosphanyl)naphthalen-1-yl)isoquinoline; copper(I) bromide In toluene at 20℃;95%
2-Ethylbutyraldehyde
97-96-1

2-Ethylbutyraldehyde

trimethylsilylacetylene
1066-54-2

trimethylsilylacetylene

dibenzylamine
103-49-1

dibenzylamine

(+/-)-N,N-dibenzyl-4-ethyl-1-(trimethylsilyl)hex-1-yn-3-amine
780782-31-2

(+/-)-N,N-dibenzyl-4-ethyl-1-(trimethylsilyl)hex-1-yn-3-amine

Conditions
ConditionsYield
With 4 A molecular sieve; copper(I) bromide In decane; toluene at 20℃;99%
With 4 A molecular sieve; copper(I) bromide In toluene at 20℃;99%
With decane; 4 A molecular sieve; copper(I) bromide In toluene at 20℃;86%
2-Ethylbutyraldehyde
97-96-1

2-Ethylbutyraldehyde

aniline
62-53-3

aniline

N-(2-ethylbutyl)aniline
6668-36-6

N-(2-ethylbutyl)aniline

Conditions
ConditionsYield
With phenylsilane; pyridine N-oxide; dibutyltin chloride In tetrahydrofuran at 20℃; for 20h;99%
2-Ethylbutyraldehyde
97-96-1

2-Ethylbutyraldehyde

aniline
62-53-3

aniline

C6H5NC6H12

C6H5NC6H12

Conditions
ConditionsYield
With silica gel In ethanol at 20℃; Ultrasound irradiation;99%
2-Ethylbutyraldehyde
97-96-1

2-Ethylbutyraldehyde

N-phenyl-maleimide
941-69-5

N-phenyl-maleimide

(R)-2-(2,5-dioxo-1-phenylpyrrolidin-3-yl)-2-ethylbutanal
1322611-71-1

(R)-2-(2,5-dioxo-1-phenylpyrrolidin-3-yl)-2-ethylbutanal

Conditions
ConditionsYield
With 1-[(1R,2R)-2-aminocyclohexyl]-3-[4-(n-perfluorooctyl)phenyl]-thiourea; benzoic acid In dichloromethane at 20℃; for 168h; asymmetric Michael addition; optical yield given as %ee; enantioselective reaction;99%
With 1-((1R,2R)-2-aminocyclohexyl)-3-(3,5-bis(trifluoromethyl)phenyl)thiourea; benzoic acid In dichloromethane at 20℃; for 3h; asymmetric Michael addition; optical yield given as %ee; enantioselective reaction;95%
With 1H-imidazole; 1-[(1S,2S)-2-aminocyclohexyl]-2,3-diisopropylguanidine In water; N,N-dimethyl-formamide at 0℃; for 96h; Michael Addition; enantioselective reaction;85%
2-Ethylbutyraldehyde
97-96-1

2-Ethylbutyraldehyde

trimethylsilyl cyanide
7677-24-9

trimethylsilyl cyanide

(S)-2-trimethylsilyloxy-2-(1-ethylpropyl)acetonitrile

(S)-2-trimethylsilyloxy-2-(1-ethylpropyl)acetonitrile

Conditions
ConditionsYield
With tetrabutoxytitanium; water; 2,4-di-tert-butyl-6-({[(1S)-1-(hydroxymethyl)-2-methylpropyl]imino}methyl)phenol In dichloromethane at 20℃; Inert atmosphere;99%
2-Ethylbutyraldehyde
97-96-1

2-Ethylbutyraldehyde

tetraphenylethane-1,2-diol
464-72-2

tetraphenylethane-1,2-diol

A

benzophenone
119-61-9

benzophenone

B

3-ethyl-1,1-diphenylpentane-1,2-diol

3-ethyl-1,1-diphenylpentane-1,2-diol

Conditions
ConditionsYield
With titanium(IV) tetrabutoxide; triethylsilyl chloride In dichloromethane at 20℃;A n/a
B 99%
2-Ethylbutyraldehyde
97-96-1

2-Ethylbutyraldehyde

2-bromo-3,3,3-trifluoropropene
1514-82-5

2-bromo-3,3,3-trifluoropropene

5-ethyl-1,1,1-trifluoro-2-heptyn-4-ol
1147879-99-9

5-ethyl-1,1,1-trifluoro-2-heptyn-4-ol

Conditions
ConditionsYield
Stage #1: 2-bromo-3,3,3-trifluoropropene With n-butyllithium; N-ethyl-N,N-diisopropylamine In tetrahydrofuran; hexane at -78℃; for 0.333333h; Inert atmosphere;
Stage #2: 2-Ethylbutyraldehyde In tetrahydrofuran; hexane at -78℃; for 1h; Inert atmosphere;
99%
2-Ethylbutyraldehyde
97-96-1

2-Ethylbutyraldehyde

pentan-3-yl formate
58368-67-5

pentan-3-yl formate

Conditions
ConditionsYield
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 20℃; for 1h;99%
2-Ethylbutyraldehyde
97-96-1

2-Ethylbutyraldehyde

2-ethylbutyl 2-ethylbutanoate
55145-34-1

2-ethylbutyl 2-ethylbutanoate

Conditions
ConditionsYield
With C18BF16(1-)*C34H53F2NiOP2(1+) In toluene at 20℃; for 1h; Glovebox; Inert atmosphere;98%
With aluminum ethoxide
With aluminum isopropoxide
2-Ethylbutyraldehyde
97-96-1

2-Ethylbutyraldehyde

1-(diethylphosphono)decan-2-one
131721-21-6

1-(diethylphosphono)decan-2-one

(E)-3-Ethyl-tetradec-4-en-6-one

(E)-3-Ethyl-tetradec-4-en-6-one

Conditions
ConditionsYield
With sodium hydride In tetrahydrofuran at 50℃; for 1h;98%
With sodium hydride In tetrahydrofuran at 50℃; for 1h; other aldehydes and β-ketophosphonates; variation of conditions;
2-Ethylbutyraldehyde
97-96-1

2-Ethylbutyraldehyde

C19H24NO8P(2-)*2K(1+)

C19H24NO8P(2-)*2K(1+)

1-(2,5-Dimethoxy-benzyl)-3-((E)-4-ethyl-hex-2-enoyl)-4-hydroxy-1,5-dihydro-pyrrol-2-one

1-(2,5-Dimethoxy-benzyl)-3-((E)-4-ethyl-hex-2-enoyl)-4-hydroxy-1,5-dihydro-pyrrol-2-one

Conditions
ConditionsYield
In tetrahydrofuran at 0℃; for 12h;98%
2-Ethylbutyraldehyde
97-96-1

2-Ethylbutyraldehyde

diethyl [1-amine(4-methoxyphenyl)methyl]phosphonate
110470-34-3, 110548-53-3, 110548-54-4, 112564-56-4

diethyl [1-amine(4-methoxyphenyl)methyl]phosphonate

diethyl {[(E)-2-ethyl-1-butylidene]amino}(4-methoxyphenyl)methylphosphonate
699000-76-5

diethyl {[(E)-2-ethyl-1-butylidene]amino}(4-methoxyphenyl)methylphosphonate

Conditions
ConditionsYield
With magnesium sulfate In dichloromethane for 3h; Heating;98%
2-Ethylbutyraldehyde
97-96-1

2-Ethylbutyraldehyde

[Amino-(4-bromo-phenyl)-methyl]-phosphonic acid diethyl ester
189180-13-0

[Amino-(4-bromo-phenyl)-methyl]-phosphonic acid diethyl ester

diethyl (4-bromophenyl){[(E)-2-ethyl-1-butylidene]amino}methylphosphonate
699000-79-8

diethyl (4-bromophenyl){[(E)-2-ethyl-1-butylidene]amino}methylphosphonate

Conditions
ConditionsYield
With magnesium sulfate In dichloromethane for 3h; Heating;98%
2-Ethylbutyraldehyde
97-96-1

2-Ethylbutyraldehyde

(S)-1-phenyl-ethylamine
2627-86-3

(S)-1-phenyl-ethylamine

potassium cyanide
151-50-8

potassium cyanide

(2S)-3-ethyl-2-{[(1S)-1-phenylethyl]amino}pentanenitrile
443991-10-4

(2S)-3-ethyl-2-{[(1S)-1-phenylethyl]amino}pentanenitrile

Conditions
ConditionsYield
With hydrogenchloride In methanol; water at 20℃; for 72h; Strecker reaction;98%
(E)-1-(4-tolylthio)-3,3,3-trifluoroprop-1-ene
940881-02-7

(E)-1-(4-tolylthio)-3,3,3-trifluoroprop-1-ene

2-Ethylbutyraldehyde
97-96-1

2-Ethylbutyraldehyde

(E)-5-ethyl-1,1,1-trifluoro-3-(p-tolylthio)hept-2-en-4-ol

(E)-5-ethyl-1,1,1-trifluoro-3-(p-tolylthio)hept-2-en-4-ol

Conditions
ConditionsYield
Stage #1: (E)-1-(4-tolylthio)-3,3,3-trifluoroprop-1-ene With n-butyllithium; N,N,N,N,-tetramethylethylenediamine In tetrahydrofuran; hexane at -78℃;
Stage #2: 2-Ethylbutyraldehyde In tetrahydrofuran; hexane at -78℃; for 0.25h; Further stages.;
98%
Stage #1: (E)-1-(4-tolylthio)-3,3,3-trifluoroprop-1-ene With N,N,N,N,-tetramethylethylenediamine In tetrahydrofuran at -78 - 20℃; Inert atmosphere;
Stage #2: With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.166667h; Inert atmosphere;
Stage #3: 2-Ethylbutyraldehyde Further stages;
98%
2-Ethylbutyraldehyde
97-96-1

2-Ethylbutyraldehyde

methyl hexanoate
106-70-7

methyl hexanoate

C13H26O3

C13H26O3

Conditions
ConditionsYield
With di-n-butylboryl trifluoromethanesulfonate; N-ethyl-N,N-diisopropylamine In dichloromethane at -78℃; optical yield given as %de; stereoselective reaction;98%
2-Ethylbutyraldehyde
97-96-1

2-Ethylbutyraldehyde

N-phenyl-maleimide
941-69-5

N-phenyl-maleimide

(S)-2-(2,5-dioxo-1-phenylpyrrolidin-3-yl)-2-ethylbutanal
1350897-04-9

(S)-2-(2,5-dioxo-1-phenylpyrrolidin-3-yl)-2-ethylbutanal

Conditions
ConditionsYield
With (S)-3-amino-3-phenylpropanoic acid; caesium carbonate In dichloromethane at 20℃; for 48h; Michael Addition; enantioselective reaction;98%
Stage #1: 2-Ethylbutyraldehyde With tert-butyl (2S,3R)-2-amino-3-hydroxybutanoate; potassium hydroxide In dichloromethane at 23℃; for 0.0333333h; Michael addition;
Stage #2: N-phenyl-maleimide In dichloromethane at 23℃; for 6h; Michael addition; optical yield given as %ee; enantioselective reaction;
96%
With NH2-Phg-(D-Pro)-Gly-Leu-OH In acetonitrile at 20℃; for 72h; Michael Addition; enantioselective reaction;95%
With (R)-3-phenyl-3-aminopropionic acid; potassium hydroxide In dichloromethane at 20℃; for 48h; Michael Addition; enantioselective reaction;
2-Ethylbutyraldehyde
97-96-1

2-Ethylbutyraldehyde

trimethylsilyl cyanide
7677-24-9

trimethylsilyl cyanide

3-ethyl-2-(trimethylsilyloxy)pentanenitrile
100020-20-0

3-ethyl-2-(trimethylsilyloxy)pentanenitrile

Conditions
ConditionsYield
With rasta resin-PPh3BnCl In chloroform at 50℃; for 0.5h; Inert atmosphere;97%
zinc(II) iodide at 90 - 100℃; for 3h;82%
With zinc(II) iodide
With potassium carbonate In diethyl ether at 20℃; for 6h; Inert atmosphere;
2-Ethylbutyraldehyde
97-96-1

2-Ethylbutyraldehyde

5-(1-Ethyl-propyl)-4-methyl-4-phenyl-4,5-dihydro-oxazole

5-(1-Ethyl-propyl)-4-methyl-4-phenyl-4,5-dihydro-oxazole

Conditions
ConditionsYield
With sodium hydroxide; tetrabutylammomium bromide In benzene for 2h; Ambient temperature;97%
2-Ethylbutyraldehyde
97-96-1

2-Ethylbutyraldehyde

3-bromopropylamine hydrochloride
5003-71-4

3-bromopropylamine hydrochloride

N-(2-ethyl-1-butylidene)-3-bromopropylamine

N-(2-ethyl-1-butylidene)-3-bromopropylamine

Conditions
ConditionsYield
With magnesium sulfate; triethylamine In dichloromethane for 1h; Ambient temperature;97%
2-Ethylbutyraldehyde
97-96-1

2-Ethylbutyraldehyde

aminomethylphosphonic acid diethyl ester
50917-72-1

aminomethylphosphonic acid diethyl ester

diethyl {[(E)-2-ethyl-1-butylidene]amino}methylphosphonate
699000-70-9

diethyl {[(E)-2-ethyl-1-butylidene]amino}methylphosphonate

Conditions
ConditionsYield
With magnesium sulfate In dichloromethane for 3h; Heating;97%
With magnesium sulfate In dichloromethane Yield given;
2-Ethylbutyraldehyde
97-96-1

2-Ethylbutyraldehyde

diethyl 1-aminophenylmethylphosphonate
16814-08-7, 42077-95-2, 42077-97-4

diethyl 1-aminophenylmethylphosphonate

diethyl {[(E)-2-ethyl-1-butylidene]amino}(phenyl)methylphosphonate
699000-73-2

diethyl {[(E)-2-ethyl-1-butylidene]amino}(phenyl)methylphosphonate

Conditions
ConditionsYield
With magnesium sulfate In dichloromethane for 3h; Heating;97%
2-Ethylbutyraldehyde
97-96-1

2-Ethylbutyraldehyde

trimethylsilylacetylene
1066-54-2

trimethylsilylacetylene

dibenzylamine
103-49-1

dibenzylamine

N,N-dibenzyl-4-ethyl-1-(trimethylsilyl)-1-heptyn-3-amine
872357-79-4

N,N-dibenzyl-4-ethyl-1-(trimethylsilyl)-1-heptyn-3-amine

Conditions
ConditionsYield
With (R)-1-(2-(diphenylphosphanyl)naphthalen-1-yl)isoquinoline; 4 A molecular sieve; copper(I) bromide In decane; toluene at 20℃;97%
2-Ethylbutyraldehyde
97-96-1

2-Ethylbutyraldehyde

nitromethane
75-52-5

nitromethane

(R)-(-)-3-ethyl-1-nitro-2-pentanol

(R)-(-)-3-ethyl-1-nitro-2-pentanol

Conditions
ConditionsYield
With C36H44N4O4S2; copper(I) bromide In methanol at 20℃; for 36h; Henry reaction; Inert atmosphere; optical yield given as %ee; enantioselective reaction;97%
With 4-methyl-N-[(1R)-2-{[(1S,2S)-2-{[(2R)-2-(4-methylbenzenesulfonamido)-2-phenylethyl]amino}-1,2-diphenylethy]amino}-1-phenylethyl]benzene-1-sulfonamido; copper(II) acetate monohydrate In ethanol at 20℃; for 48h; Henry reaction; Inert atmosphere; optical yield given as %ee; enantioselective reaction;89%
With C32H20N4O2 In methanol at 20℃; for 8h; Reagent/catalyst; Henry Nitro Aldol Condensation; enantioselective reaction;89%

97-96-1Relevant articles and documents

HIGHLY EFFICIENT METHOD FOR PRODUCING SATURATED HOMOETHER FROM UNSATURATED CARBONYL COMPOUND

-

Paragraph 0049; 0051-0052, (2020/07/16)

PROBLEM TO BE SOLVED: To provide a method for efficiently producing a saturated homoether from an unsaturated carbonyl compound. SOLUTION: The method for producing an unsaturated homoether uses an unsaturated carbonyl compound and hydrogen as a raw material, uses a catalyst comprising a metal supported on an acidic catalyst carrier and performs at least once a pressure reduction operation so that a differential pressure from a reaction pressure is 0.01 MPa or more. In the method, the metal of the catalyst is, for example, palladium and the carrier of the catalyst is alumina, silica, silica-alumina or the like. The unsaturated carbonyl compound serving as a raw material is 2-butenal, 2-ethyl-2-hexenal, 2-ethyl-2-butenal, 2-hexenal or the like and the produced saturated homoether is dibutyl ether, bis(2-ethylhexyl)ether, bis(2-ethylbutyl)ether, dihexyl ether or the like. SELECTED DRAWING: None COPYRIGHT: (C)2020,JPOandINPIT

Utilization of hexabromoacetone for protection of alcohols and aldehydes and deprotection of acetals, ketals, and oximes under UV irradiation

Chaiseeda, Kittichai,Chantharadet, Ladawan,Chavasiri, Warinthorn

, p. 1305 - 1323 (2017/10/30)

Hexabromoacetone (HBA) was efficiently used for the protection of alcohols and aldehydes and deprotection of benzaldehyde dimethyl acetal, solketal, and other acetals and ketals. In only 10?min, the protection of glycerol yielded 90% of solketal and protection of benzaldehyde gave 95% of benzaldehyde dimethyl acetal. The deprotection of benzaldehyde dimethyl acetal under UV irradiation gave over 90% yield of benzaldehyde within 15?s using only 2.5?mol% of HBA. HBA was also successfully used for deoximation. Solvent was found to play an important role in the efficiency of HBA for these reactions.

Preparation method of key intermediate 2-ethyl butyraldehyde of 2-ethyl butyric acid

-

Paragraph 0011-0012, (2017/07/19)

The invention provides a preparation method of a key intermediate, 2-ethyl butyraldehyde, of 2-ethyl butyric acid, wherein the preparation method includes the steps of: adding an ethyl magnesium halide Grignard reagent to a protected alpha-halogenated aldehyde (I) solution, and performing a stirring reaction for 1-10 h at a certain temperature; performing post-treatment and de-protecting the product to obtain the 2-ethyl butyraldehyde. A route in the process in represented as follows. The method has short route and high usage ratio, is low in cost and easy to industrialize, and avoids defects in conventional methods.

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