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78-84-2 Usage

Reactivity Profile

Isobutyraldehyde can react vigorously with reducing agents, with oxidizing agents, strong bases and mineral acids. Can undergo exothermic self-condensation or polymerization reactions that are often catalyzed by acid. Generates flammable and/or toxic gases in combination with azo, diazo compounds, dithiocarbamates, nitrides, and strong reducing agents. Reacts slowly when exposed to air with air to give peroxides and other products. These reactions are activated by light, catalyzed by salts of transition metals, and are autocatalytic (catalyzed by their products). The addition of stabilizers (antioxidants) retards autoxidation.

General Description

A clear colorless liquid with a pungent odor. Flash point of -40°F. Less dense than water and insoluble in water. Hence floats on water. Vapors are heavier than air. Used to make other chemicals.

References

https://pubchem.ncbi.nlm.nih.gov/compound/isobutyraldehyde#section=Top
http://chemindustry.ru/Isobutyraldehyde.php
http://product-finder.basf.com/group/corporate/product-finder/en/brand/ISOBUTYRALDEHYDE
https://en.wikipedia.org/wiki/Isobutyraldehyde

Air & Water Reactions

Highly flammable. Oxidizes slowly on exposure to air. Stable (less than 10% decomposition) for four hours when exposed to light and air in a closed system. Stable for two weeks when stored under nitrogen at temperatures up to 77°F. Insoluble in water.

Chemical Properties

colourless liquid with an extremely unpleasant smell

Purification Methods

Dry isobutyraldehyde with CaSO4 and use it immediately after distillation under nitrogen because of the great difficulty in preventing oxidation. It can be purified through its acid bisulfite derivative. [Beilstein 1 IV 3262.]

Description

Isobutyraldehyde, also known as 2-Methylpropanal, is an organic compound belonging to the family of aldehydes, which can be found in alcoholic beverages, tea, breads, cooked pork, spearmint oil as well as fresh fruits, such as apple, banana, cherry, etc. It is manufactured by the hydroformylation of propene, usually obtained as a side-product. It can be applied as a source for producing other chemicals, including isobutyl alcohol, neopentyl glycol as well as isobutanoic acid production and used to produce amino acids such as valine and leucine. Besides, isobutyraldehyde commonly serves as an intermediate in the field of chemical industry for manufacture of pharmaceuticals (such as Vitamin B5), crop protection products, pesticides, synthetic resins, antioxidants, vulcanisation accelerators, textile auxiliaries, perfumery and flavors.

Fire Hazard

Behavior in Fire: Vapors are heavier than air and may travel considerable distance to a source of ignition and flash back. Fires are difficult to control due to ease of reignition.

Health Hazard

Vapor is irritating to the eyes and mucous membranes.

Uses

In the synthesis of pantothenic acid, valine, leucine, cellulose esters, perfumes, flavors, plasticizers, resins, gasoline additives.

Definition

ChEBI: A member of the class of propanals that is propanal substituted by a methyl group at position 2.
InChI:InChI=1/C4H8O/c1-4(2)3-5/h3-4H,1-2H3

78-84-2 Well-known Company Product Price

Brand (Code)Product description CAS number Packaging Price Detail
Alfa Aesar (A12106)  Isobutyraldehyde, 98%    78-84-2 2500ml 1211.0CNY Detail
Alfa Aesar (A12106)  Isobutyraldehyde, 98%    78-84-2 500ml 284.0CNY Detail
TCI America (I0101)  Isobutyraldehyde  >98.0%(GC) 78-84-2 500mL 240.00CNY Detail
TCI America (I0101)  Isobutyraldehyde  >98.0%(GC) 78-84-2 25mL 110.00CNY Detail

78-84-2SDS

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 isobutyraldehyde

1.2 Other means of identification

Product number -
Other names Isobutaldehyde

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:78-84-2 SDS

78-84-2Synthetic route

2-benzoyl-N-benzyl-2-methylpropanimine
105361-41-9

2-benzoyl-N-benzyl-2-methylpropanimine

A

phenylmethanaminium benzoate
34243-68-0

phenylmethanaminium benzoate

B

isobutyraldehyde
78-84-2

isobutyraldehyde

Conditions
ConditionsYield
With water In diethyl ether Ambient temperature;A 100%
B 100%
2-methyl-propan-1-ol
78-83-1

2-methyl-propan-1-ol

isobutyraldehyde
78-84-2

isobutyraldehyde

Conditions
ConditionsYield
Stage #1: 2-methyl-propan-1-ol With cobalt ferrite In water for 0.0333333h;
Stage #2: With oxone(R) In water at 20℃; for 4h;
99.5%
With triethylammonium fluorochromate(VI) In dichloromethane for 1.16667h; Heating;92%
With trimethylammonium fluorochromate In dichloromethane for 1.06667h; Heating;92%
isobutyric Acid
79-31-2

isobutyric Acid

isobutyraldehyde
78-84-2

isobutyraldehyde

Conditions
ConditionsYield
With thexylbromoborane dimethyl sulfide complex In carbon disulfide; dichloromethane at -20 - 20℃; for 1h;99%
With 9-borabicyclo[3.3.1]nonane dimer; lithium dihydrido borata-bicyclo[3.3.0]nonane In tetrahydrofuran for 1h; Ambient temperature;94%
With iron(II) oxide at 430 - 490℃;
lithium dimethylacetate
25179-23-1

lithium dimethylacetate

isobutyraldehyde
78-84-2

isobutyraldehyde

Conditions
ConditionsYield
With 9-borabicyclo[3.3.1]nonane dimer In tetrahydrofuran for 1h; Ambient temperature;99%
2-methylpropenal
78-85-3

2-methylpropenal

isobutyraldehyde
78-84-2

isobutyraldehyde

Conditions
ConditionsYield
With hydrogen In acetone at 20℃; under 760.051 Torr; for 0.25h; chemoselective reaction;99%
With hydrogen; sodium triethylborohydride In tetrahydrofuran at 23℃; under 30402 Torr; for 72h; Catalytic behavior; Inert atmosphere; Schlenk technique;76%
With hydrogen In ethyl acetate at 20℃; under 760.051 Torr; for 0.25h; chemoselective reaction;
(2RS,4RS)-2-isopropyl-5,5-dimethylthiazolidine-4-carbocyclic acid

(2RS,4RS)-2-isopropyl-5,5-dimethylthiazolidine-4-carbocyclic acid

A

2-amino-3-mercapto-4-methylpentanoic acid
98278-26-3

2-amino-3-mercapto-4-methylpentanoic acid

B

isobutyraldehyde
78-84-2

isobutyraldehyde

Conditions
ConditionsYield
With water at 90℃; Column which a strongly acidic cation exchanger in the H+ form;A 98.8%
B 96.9%
isobutyraldehyde dimethyl acetal
41632-89-7

isobutyraldehyde dimethyl acetal

A

1-methoxy-2-methylprop-1-ene
17574-84-4

1-methoxy-2-methylprop-1-ene

B

isobutyraldehyde
78-84-2

isobutyraldehyde

Conditions
ConditionsYield
With water; toluene-4-sulfonic acid; triethylamine at 90℃; under 760.051 Torr; Product distribution / selectivity;A 98.5%
B n/a
2-methyl-1,2-epoxypropane
558-30-5

2-methyl-1,2-epoxypropane

A

2-methyl-propan-1-ol
78-83-1

2-methyl-propan-1-ol

B

isobutyraldehyde
78-84-2

isobutyraldehyde

Conditions
ConditionsYield
With hydrogen; chromium(III) oxide; copper at 140℃; under 26252.1 Torr; for 0.666667h;A 98.1%
B 1.9%
1-(1-Butylsulfanyl-2-methyl-propylsulfanyl)-butane
95915-86-9

1-(1-Butylsulfanyl-2-methyl-propylsulfanyl)-butane

isobutyraldehyde
78-84-2

isobutyraldehyde

Conditions
ConditionsYield
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In acetonitrile at 20 - 25℃; for 2h; Irradiation;96%
nitrous acid isobutyl ester
542-56-3

nitrous acid isobutyl ester

isobutyraldehyde
78-84-2

isobutyraldehyde

Conditions
ConditionsYield
With dimethyl sulfoxide at 70℃; for 6h;95.95%
With boron trifluoride diethyl etherate In diethyl ether for 4h; Ambient temperature;92%
isobutyryl chloride
79-30-1

isobutyryl chloride

isobutyraldehyde
78-84-2

isobutyraldehyde

Conditions
ConditionsYield
With tri-n-butyl-tin hydride; trans benzyl(chloro)bis(triphenylphosphine)palladium(II) In diethyl ether for 0.166667h; Ambient temperature;95%
With ammonium hydroxide; formic acid In diethyl ether; chloroform for 0.416667h; Ambient temperature;86%
With diethylene glycol dimethyl ether; lithium tri-t-butoxyaluminum hydride at -78℃;
3-hydroxy-2-methyl-1-propene
513-42-8

3-hydroxy-2-methyl-1-propene

A

2-methyl-2-propen-1-ol
56640-70-1

2-methyl-2-propen-1-ol

B

isobutyraldehyde
78-84-2

isobutyraldehyde

Conditions
ConditionsYield
ClO4 at 0℃; for 1h; Title compound not separated from byproducts;A 95%
B 5%
ClO4 at 0℃; for 1h;A 95 % Spectr.
B 5 % Spectr.
ClO4 at 27℃; Mechanism; other solvents;A 95 % Spectr.
B 5 % Spectr.
propene
187737-37-7

propene

carbon monoxide
201230-82-2

carbon monoxide

A

butyraldehyde
123-72-8

butyraldehyde

B

isobutyraldehyde
78-84-2

isobutyraldehyde

Conditions
ConditionsYield
With dicarbonylacetylacetonato rhodium (I); C41H30O8P2; hydrogen In toluene at 90℃; under 3750.38 - 7500.75 Torr; for 3h; Reagent/catalyst; regioselective reaction;A 93.9%
B n/a
With tributylphosphine; hydrogen; cobalt(II) acetate In methanol at 85℃; under 60004.8 Torr; for 24h; Irradiation; Yield given. Yields of byproduct given;
With hydrogen; Dioctadecylamine; Rh-distearylamine-1,3-bis-disulfonatophenyl phosphinopropane; rhodium at 125℃; under 202516 Torr; for 2h; Yield given. Yields of byproduct given;
{PPN}{HCr(CO)5}
78362-94-4

{PPN}{HCr(CO)5}

isobutyryl chloride
79-30-1

isobutyryl chloride

A

bis(triphenylphosphine)nitrogen{Cr(CO)5Cl}
65650-76-2

bis(triphenylphosphine)nitrogen{Cr(CO)5Cl}

B

isobutyraldehyde
78-84-2

isobutyraldehyde

Conditions
ConditionsYield
In tetrahydrofuran 1:1 molar ratio, THF, 25°C;; detected by NMR and IR spectra; and GC analysis,;A n/a
B 93%
isobutyraldehyde oxime
151-00-8

isobutyraldehyde oxime

isobutyraldehyde
78-84-2

isobutyraldehyde

Conditions
ConditionsYield
With N-bromosaccharin In acetone for 0.0416667h; Heating; microwave irradiation;92%
With N-bromosaccharin In water; acetone at 20℃; for 2h;92%
With N,N'-dibromo-N,N'-1,3-propylene-bis[(4-methylphenyl)sulfonamide] In dichloromethane; water for 0.02h; Heating; microwave irradiation;92%
3-isopropyl-6,6-dimethyl-5-(o-toluidino)-1,2,4-trioxan
122346-61-6

3-isopropyl-6,6-dimethyl-5-(o-toluidino)-1,2,4-trioxan

A

2'-methylformanilide
94-69-9

2'-methylformanilide

B

isobutyraldehyde
78-84-2

isobutyraldehyde

C

acetone
67-64-1

acetone

Conditions
ConditionsYield
at 110℃; for 0.25h;A 84%
B 91%
C 68%
isobutyric acid sodium salt
996-30-5

isobutyric acid sodium salt

isobutyraldehyde
78-84-2

isobutyraldehyde

Conditions
ConditionsYield
With 9-borabicyclo[3.3.1]nonane dimer In tetrahydrofuran for 1h; Ambient temperature;91%
N-(Benzylidene)-2-methyl-1-propenylamine
68003-61-2

N-(Benzylidene)-2-methyl-1-propenylamine

A

benzaldehyde
100-52-7

benzaldehyde

B

isobutyraldehyde
78-84-2

isobutyraldehyde

Conditions
ConditionsYield
With hydrogenchloride In dichloromethane for 1h; Heating;A 83%
B 90%
2-methylpropane-1,1-diyl diacetate
6283-77-8

2-methylpropane-1,1-diyl diacetate

isobutyraldehyde
78-84-2

isobutyraldehyde

Conditions
ConditionsYield
With N,N'-dibromo-N,N'-(1,2-ethanediyl)bis(p-toluenesulfonamide); water at 20℃; for 0.0333333h; solid-phase reaction;90%
With silica phosphoric acid In methanol at 20℃; for 3.5h;87%
With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione; water; silica gel at 20℃; for 0.0666667h; neat (no solvent); chemoselective reaction;86%
With water at 20℃; for 0.333333h; Green chemistry;90 %Chromat.
isobutylamine
78-81-9

isobutylamine

isobutyraldehyde
78-84-2

isobutyraldehyde

Conditions
ConditionsYield
With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene In dichloromethane at 0 - 20℃; for 0.333333h; Inert atmosphere; Green chemistry;89%
With potassium permanganate; iron(II) sulfate In dichloromethane for 6h; Heating;80%
With dipotassium peroxodisulfate; sodium carbonate In water for 0.333333h; Rate constant; Irradiation; pH: 11.5, rate constant (k M-1s-1);
2-methylpropyl(methyl)amine
625-43-4

2-methylpropyl(methyl)amine

isobutyraldehyde
78-84-2

isobutyraldehyde

Conditions
ConditionsYield
With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene In dichloromethane at 0 - 20℃; for 0.333333h; Inert atmosphere; Green chemistry;89%
2-methyl-1,2-epoxypropane
558-30-5

2-methyl-1,2-epoxypropane

A

isobutyraldehyde
78-84-2

isobutyraldehyde

B

3-hydroxy-2-methyl-1-propene
513-42-8

3-hydroxy-2-methyl-1-propene

Conditions
ConditionsYield
lithium phosphate at 210℃; for 3h; Kinetics; Thermodynamic data; 110 - 180 degC , ΔG, ΔH, E(activ.);A 5.79%
B 85.1%
With hydrogen; lithium phosphate at 210℃; for 3h;A 5.79%
B 85.1%
With 3-chlorobenzoate; methanesulfonic acid In dichloromethane-d2 at 26.5℃; Product distribution; various conc. of methanesulfonic acid in the presence and absence of 3-chlorobenzoic acid;A 10%
B 20%
With 3-chlorobenzoate; methanesulfonic acid In dichloromethane-d2 at 26.5℃;A 10%
B 20%
trans-[Ir(PPh3)2]CO(OCH2CHMe2)
357276-13-2

trans-[Ir(PPh3)2]CO(OCH2CHMe2)

triphenylphosphine-d15
24762-44-5

triphenylphosphine-d15

A

(P(C6H5)3)2P(C6(2)H5)3(CO)IrH

(P(C6H5)3)2P(C6(2)H5)3(CO)IrH

B

isobutyraldehyde
78-84-2

isobutyraldehyde

Conditions
ConditionsYield
In (2)H8-toluene Kinetics; toluene-d7, PPh3, 95°C; not sepd., detected by (1)H-NMR and mass-spectra;A n/a
B 81%
lithium formate
556-63-8

lithium formate

isopropylmagnesium chloride
1068-55-9

isopropylmagnesium chloride

isobutyraldehyde
78-84-2

isobutyraldehyde

Conditions
ConditionsYield
In tetrahydrofuran for 2h; Heating;80%
1-(N-Methyl-N-phenylamino)-2-methyl-1-propene
25076-84-0

1-(N-Methyl-N-phenylamino)-2-methyl-1-propene

isobutyraldehyde
78-84-2

isobutyraldehyde

Conditions
ConditionsYield
With hydrogenchloride In tetrahydrofuran for 5h; Ambient temperature;78%
2-methyl-propan-1-ol
78-83-1

2-methyl-propan-1-ol

A

2-chloro-2-methyl-1-propanol
558-38-3

2-chloro-2-methyl-1-propanol

B

2-chloroisobutyraldehyde
917-93-1

2-chloroisobutyraldehyde

C

isobutyraldehyde
78-84-2

isobutyraldehyde

Conditions
ConditionsYield
With chlorine dioxide In n-heptane at 30℃; Kinetics;A 10%
B 5%
C 77%
isobutyraldehyde oxime
151-00-8

isobutyraldehyde oxime

A

isobutyraldehyde
78-84-2

isobutyraldehyde

B

isobutyric Acid
79-31-2

isobutyric Acid

Conditions
ConditionsYield
With hydrogenchloride; sodium chlorite; water at 20℃; for 0.0833333h;A 76%
B 8%
isopropylmagnesium chloride
1068-55-9

isopropylmagnesium chloride

sodium formate
141-53-7

sodium formate

isobutyraldehyde
78-84-2

isobutyraldehyde

Conditions
ConditionsYield
In tetrahydrofuran for 2h; Heating;75%
3-hydroxy-2-methyl-1-propene
513-42-8

3-hydroxy-2-methyl-1-propene

isobutyraldehyde
78-84-2

isobutyraldehyde

Conditions
ConditionsYield
(sulphos)Rh(CO)2 In octane; water at 100℃; for 1h; Product distribution; Further Variations:; Solvents; autoclave;73%
With [Ru(η3:η3-C10H16)Cl2(benzimidazole)] In glycerol at 75℃; for 16h; Sealed tube; Inert atmosphere; Green chemistry;36%
With sulfuric acid at 105℃; unter Druck;
Pentaerythritol
115-77-5

Pentaerythritol

isobutyraldehyde
78-84-2

isobutyraldehyde

3,9-diisopropyl-2,4,8,10-tetraoxaspiro<5.5>undecane
69695-04-1

3,9-diisopropyl-2,4,8,10-tetraoxaspiro<5.5>undecane

Conditions
ConditionsYield
With sulfuric acid at 80℃;100%
With indium(III) chloride at 120℃; for 3h;89%
With hydrogenchloride
isobutyraldehyde
78-84-2

isobutyraldehyde

benzylamine
100-46-9

benzylamine

isobutylidenebenzylamine
22483-21-2

isobutylidenebenzylamine

Conditions
ConditionsYield
With magnesium sulfate In dichloromethane at 20℃; Inert atmosphere;100%
With aluminum oxide at 20℃; for 7h;90%
In water Condensation;65.12%
isobutyraldehyde
78-84-2

isobutyraldehyde

2,4,6-triisopropyl-1,3,5-trioxane
7580-12-3

2,4,6-triisopropyl-1,3,5-trioxane

Conditions
ConditionsYield
With beryllium iodide In chloroform-d1 at 20℃; Schlenk technique; Glovebox; Inert atmosphere; Sealed tube;100%
With dodecatungstosilic acid for 1h; Ambient temperature;99.9%
With N,N,N',N'',N''-pentamethyl-N,N''-bis(3-sulfopropyl)diethylenetriaminium tris(trifluoromethanesulfonate) In neat (no solvent) at 20℃; for 1.5h; Catalytic behavior; Reagent/catalyst; Inert atmosphere; Green chemistry;97.6%
isobutyraldehyde
78-84-2

isobutyraldehyde

isobutyl isobutanoate
97-85-8

isobutyl isobutanoate

Conditions
ConditionsYield
With [(ImDippN)Th{N(SiMe3)2}3] In benzene-d6 at 20℃; for 24h; Reagent/catalyst;100%
With [{(PhN)MeC(Nt-Bu)}AlMe(μ-OMe)]2 at 20℃; for 0.5h; Reagent/catalyst; Tishchenko-Claisen Dismutation; Inert atmosphere; Schlenk technique; Green chemistry;99%
tris(bis(trimethylsilyl)amido)lanthanum(III) In benzene-d6 at 21℃; for 24h; Tishchenko reaction;84%
isobutyraldehyde
78-84-2

isobutyraldehyde

aniline
62-53-3

aniline

N-isobutylaniline
588-47-6

N-isobutylaniline

Conditions
ConditionsYield
With ammonium formate; palladium on activated charcoal In water; isopropyl alcohol at 20℃; for 0.5h;100%
With N,N,N,N,N,N-hexamethylphosphoric triamide; dibutyltin chloride In tetrahydrofuran at 0℃; for 1h; Reduction; Amination;99%
With nickel; hydrogen In neat (no solvent) at 200℃; under 760.051 Torr; Flow reactor;95.7%
pyrrolidine
123-75-1

pyrrolidine

cycl-isopropylidene malonate
2033-24-1

cycl-isopropylidene malonate

isobutyraldehyde
78-84-2

isobutyraldehyde

2,2-Dimethyl-5-(2-methyl-1-pyrrolidin-1-yl-propyl)-[1,3]dioxane-4,6-dione
93498-09-0

2,2-Dimethyl-5-(2-methyl-1-pyrrolidin-1-yl-propyl)-[1,3]dioxane-4,6-dione

Conditions
ConditionsYield
In diethyl ether for 0.166667h;100%
1,2,3-Benzotriazole
95-14-7

1,2,3-Benzotriazole

isobutyraldehyde
78-84-2

isobutyraldehyde

1-Benzotriazol-1-yl-2-methyl-propan-1-ol
111507-81-4

1-Benzotriazol-1-yl-2-methyl-propan-1-ol

Conditions
ConditionsYield
at 25℃;100%
nitrobenzene
98-95-3

nitrobenzene

isobutyraldehyde
78-84-2

isobutyraldehyde

N-isobutylaniline
588-47-6

N-isobutylaniline

Conditions
ConditionsYield
With ammonium formate; palladium on activated charcoal In water; isopropyl alcohol at 20℃; for 0.166667h;100%
With hydrogen In ethanol at 20℃; for 6h; Green chemistry;98%
With hydrogen In methanol at 20℃; under 760.051 Torr; for 4h;96%
1.3-propanedithiol
109-80-8

1.3-propanedithiol

isobutyraldehyde
78-84-2

isobutyraldehyde

2-isopropyl-1,3-dithiane
6007-25-6

2-isopropyl-1,3-dithiane

Conditions
ConditionsYield
With boron trifluoride diethyl etherate In dichloromethane at 0 - 20℃; for 1h;100%
With lithium tetrafluoroborate at 25℃; for 15h;98%
With boron trifluoride diethyl etherate In dichloromethane at 0 - 20℃; for 22h; Inert atmosphere; Molecular sieve;96%
Propiolaldehyde diethyl acetal
10160-87-9

Propiolaldehyde diethyl acetal

isobutyraldehyde
78-84-2

isobutyraldehyde

6,6-Diethoxy-2-methyl-hex-4-yn-3-ol
86517-10-4

6,6-Diethoxy-2-methyl-hex-4-yn-3-ol

Conditions
ConditionsYield
Stage #1: Propiolaldehyde diethyl acetal With n-butyllithium In tetrahydrofuran; cyclohexane at -78℃; for 0.5h; Inert atmosphere;
Stage #2: isobutyraldehyde In tetrahydrofuran; cyclohexane at -78℃; for 3h;
Stage #3: With hydrogenchloride In tetrahydrofuran; cyclohexane; water
100%
With n-butyllithium In diethyl ether; hexane for 2h; Ambient temperature;55%
methylene bis phosphonate de diethyle
63366-56-3

methylene bis phosphonate de diethyle

isobutyraldehyde
78-84-2

isobutyraldehyde

methylenebis(2,2-diethoxy-3,5-diisopropyl-1,4,2-dioxaphospholane)
111105-89-6

methylenebis(2,2-diethoxy-3,5-diisopropyl-1,4,2-dioxaphospholane)

Conditions
ConditionsYield
In neat (no solvent) 1) 20 deg C, 48h, 2) 0.5 mm Hg, 20 deg C, 30 min.;100%
5,5-dimethyl-2-(2-methyl)propylidenecyclohexane-1,3-dione
83814-58-8

5,5-dimethyl-2-(2-methyl)propylidenecyclohexane-1,3-dione

isobutyraldehyde
78-84-2

isobutyraldehyde

2,4-diisopropyl-7,7-dimethyl-7,8-dihydro-4H-1,3-benzodioxin-5(6H)-one
83814-62-4

2,4-diisopropyl-7,7-dimethyl-7,8-dihydro-4H-1,3-benzodioxin-5(6H)-one

Conditions
ConditionsYield
With boron trifluoride diethyl etherate In diethyl ether; dichloromethane for 5h;100%
difluoromethyl phenyl sulfone
1535-65-5

difluoromethyl phenyl sulfone

isobutyraldehyde
78-84-2

isobutyraldehyde

1,1-difluoro-3-methyl-1-(phenylsulfonyl)butan-2-ol
122590-91-4

1,1-difluoro-3-methyl-1-(phenylsulfonyl)butan-2-ol

Conditions
ConditionsYield
With sodium hydroxide In dichloromethane100%
With lithium hexamethyldisilazane In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide at -78℃; for 4h;97%
With sodium hydroxide; Aliquat 336 In dichloromethane73%
2,6-di-tert-butyl-4-methylphenyl propionate
72959-50-3

2,6-di-tert-butyl-4-methylphenyl propionate

isobutyraldehyde
78-84-2

isobutyraldehyde

2',6'-bis(1
81818-92-0, 103514-50-7

2',6'-bis(1",1"-dimethylethyl)-4'-methylphenyl (2SR,3SR)-2,4-dimethyl-3-hydroxypentanoate

Conditions
ConditionsYield
With lithium diisopropyl amide In tetrahydrofuran at 70℃; for 0.833333h;100%
Stage #1: 2,6-di-tert-butyl-4-methylphenyl propionate With n-butyllithium; polymer-bound N-isopropyl-5-(4-vinylphenyl)pentylamine In tetrahydrofuran; hexane at -78℃; for 0.25h;
Stage #2: isobutyraldehyde In tetrahydrofuran; hexane at -78℃; for 1.5h; Further stages.;
79%
isobutyraldehyde
78-84-2

isobutyraldehyde

allyl-trimethyl-silane
762-72-1

allyl-trimethyl-silane

threo-3-(trimethylsilyl)-4-hydroxy-5-methyl-1-hexene
88916-15-8

threo-3-(trimethylsilyl)-4-hydroxy-5-methyl-1-hexene

Conditions
ConditionsYield
With N,N,N,N,N,N-hexamethylphosphoric triamide; dicyclopentylboron chloride; tert.-butyl lithium In tetrahydrofuran -78 deg C to r.t.;100%
isobutyraldehyde
78-84-2

isobutyraldehyde

1-[(R)-1-((E)-2-Iodo-vinyl)-hexyloxymethyl]-4-methoxy-benzene
164524-05-4

1-[(R)-1-((E)-2-Iodo-vinyl)-hexyloxymethyl]-4-methoxy-benzene

(E)-(R)-6-(4-Methoxy-benzyloxy)-2-methyl-undec-4-en-3-ol

(E)-(R)-6-(4-Methoxy-benzyloxy)-2-methyl-undec-4-en-3-ol

Conditions
ConditionsYield
With chromium dichloride; nickel dichloride In dimethyl sulfoxide Ambient temperature;100%
With chromium chloride; nickel dichloride In dimethyl sulfoxide for 2h; Ambient temperature;100%
isobutyraldehyde
78-84-2

isobutyraldehyde

tert-Butyl-[(R)-1-((E)-2-iodo-vinyl)-hexyloxy]-diphenyl-silane
164524-06-5

tert-Butyl-[(R)-1-((E)-2-iodo-vinyl)-hexyloxy]-diphenyl-silane

(E)-(R)-6-(tert-Butyl-diphenyl-silanyloxy)-2-methyl-undec-4-en-3-ol

(E)-(R)-6-(tert-Butyl-diphenyl-silanyloxy)-2-methyl-undec-4-en-3-ol

Conditions
ConditionsYield
With chromium dichloride; nickel dichloride In dimethyl sulfoxide Ambient temperature;100%
With chromium chloride; nickel dichloride In dimethyl sulfoxide; N,N-dimethyl-formamide for 1h; Ambient temperature;100%
3-(tetrahydropyran-2'-yloxy)propyne
6089-04-9

3-(tetrahydropyran-2'-yloxy)propyne

isobutyraldehyde
78-84-2

isobutyraldehyde

1-isopropyl-4-(tetrahydro-2-pyranyloxy)-2-butyn-1-ol
41056-46-6

1-isopropyl-4-(tetrahydro-2-pyranyloxy)-2-butyn-1-ol

Conditions
ConditionsYield
Stage #1: 3-(tetrahydropyran-2'-yloxy)propyne With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 2h;
Stage #2: isobutyraldehyde In tetrahydrofuran; hexane at -78℃; for 1h; Further stages.;
100%
Stage #1: 3-(tetrahydropyran-2'-yloxy)propyne With n-butyllithium In tetrahydrofuran; hexane at -30℃; for 0.5h;
Stage #2: isobutyraldehyde In tetrahydrofuran; hexane at -30℃; for 1h; Further stages.;
89%
With n-butyllithium 1.) THF, hexane, -78 deg C, 2 h, 2.) THF, hexane, -78 deg C, 2 h; Yield given. Multistep reaction;
Stage #1: 3-(tetrahydropyran-2'-yloxy)propyne With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h;
Stage #2: isobutyraldehyde In tetrahydrofuran; hexane at -78℃;
t-butoxycarbonylhydrazine
870-46-2

t-butoxycarbonylhydrazine

isobutyraldehyde
78-84-2

isobutyraldehyde

N'-(2-methylpropylidene)hydrazinecarboxylic acid tert-butyl ester
57699-46-4

N'-(2-methylpropylidene)hydrazinecarboxylic acid tert-butyl ester

Conditions
ConditionsYield
In toluene at 50℃; for 1h;100%
In methanol at 20℃; for 1h;100%
In methanol at 20℃; for 1h; Inert atmosphere;100%
In ethanol for 3h; Heating;99%
diethoxyphosphoryl-acetic acid ethyl ester
867-13-0

diethoxyphosphoryl-acetic acid ethyl ester

isobutyraldehyde
78-84-2

isobutyraldehyde

(E)-2-(Diethoxy-phosphoryl)-4-methyl-pent-2-enoic acid ethyl ester
173724-80-6

(E)-2-(Diethoxy-phosphoryl)-4-methyl-pent-2-enoic acid ethyl ester

Conditions
ConditionsYield
With piperidine; acetic acid In benzene for 48h; Heating;100%
With piperidine; acetic acid for 62h; Condensation; Knoevenagel condensation;80%
Stage #1: diethoxyphosphoryl-acetic acid ethyl ester With triethylamine; titanium tetrachloride In dichloromethane at 0 - 5℃;
Stage #2: isobutyraldehyde In dichloromethane at 0 - 5℃; Horner-Wadsworth-Emmos reaction;
(1S,2R,4R)-(-)-10-mercaptoisoboneol
71242-58-5

(1S,2R,4R)-(-)-10-mercaptoisoboneol

isobutyraldehyde
78-84-2

isobutyraldehyde

(1S,4R,6R,8R)-4-Isopropyl-11,11-dimethyl-5-oxa-3-thia-tricyclo[6.2.1.01,6]undecane

(1S,4R,6R,8R)-4-Isopropyl-11,11-dimethyl-5-oxa-3-thia-tricyclo[6.2.1.01,6]undecane

Conditions
ConditionsYield
With boron trifluoride diethyl etherate In dichloromethane100%
isobutyraldehyde
78-84-2

isobutyraldehyde

1,4,4-trimethyl-1,2,3,4-tetrahydrophosphinoline 1-oxide
311806-49-2

1,4,4-trimethyl-1,2,3,4-tetrahydrophosphinoline 1-oxide

1-(2-Hydroxy-3-methylbutyl)-4,4-dimethyl-1,2,3,4-tetrahydrophosphinoline oxide
311806-50-5

1-(2-Hydroxy-3-methylbutyl)-4,4-dimethyl-1,2,3,4-tetrahydrophosphinoline oxide

Conditions
ConditionsYield
Stage #1: 1,4,4-trimethyl-1,2,3,4-tetrahydrophosphinoline-1-oxide With n-butyllithium In tetrahydrofuran; hexane for 0.666667h; Metallation;
Stage #2: isobutyraldehyde In tetrahydrofuran; hexane at 20℃; for 1h; Alkylation; Further stages.;
100%
isobutyraldehyde
78-84-2

isobutyraldehyde

trifluoroacetic acid
76-05-1

trifluoroacetic acid

Ac-(L)Ala-(L)Phe-NH(CH2)3NH-CPh2-p-C6H4-polystyrene

Ac-(L)Ala-(L)Phe-NH(CH2)3NH-CPh2-p-C6H4-polystyrene

N3,6,9-triisobutyl-12-amino-(4S)-methyl-(7S)-benzyl-3,6,9-triazadodecane, tetrakis(trifluoroacetic acid) salt

N3,6,9-triisobutyl-12-amino-(4S)-methyl-(7S)-benzyl-3,6,9-triazadodecane, tetrakis(trifluoroacetic acid) salt

Conditions
ConditionsYield
Multistep reaction.;100%
isobutyraldehyde
78-84-2

isobutyraldehyde

(E)-3,4-Dimethyl-1-piperidin-1-yl-5-tributylstannanyl-pent-3-en-1-one
303053-83-0

(E)-3,4-Dimethyl-1-piperidin-1-yl-5-tributylstannanyl-pent-3-en-1-one

(E)-N-(6-hydroxy-3,4,7-trimethyl-3-octenoyl)piperidine

(E)-N-(6-hydroxy-3,4,7-trimethyl-3-octenoyl)piperidine

Conditions
ConditionsYield
With dibutyltin chloride; isobutyraldehyde at 20℃; for 1h;100%
isobutyraldehyde
78-84-2

isobutyraldehyde

(8β)-De-A,B-23,23-dibromo-8-(tert-butyldimethylsilyloxy)-24-norchol-22-ene
214777-06-7

(8β)-De-A,B-23,23-dibromo-8-(tert-butyldimethylsilyloxy)-24-norchol-22-ene

(8β)-De-A,B-8-(tert-butyldimethylsilyloxy)-22-cholestyne-24-ol
263712-12-5

(8β)-De-A,B-8-(tert-butyldimethylsilyloxy)-22-cholestyne-24-ol

Conditions
ConditionsYield
Stage #1: (8β)-De-A,B-23,23-dibromo-8-(tert-butyldimethylsilyloxy)-24-norchol-22-ene With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃; for 1.5h;
Stage #2: isobutyraldehyde In tetrahydrofuran; hexane at -78℃; for 0.333333h;
100%
chloromethyl phenyl sulfone
7205-98-3

chloromethyl phenyl sulfone

isobutyraldehyde
78-84-2

isobutyraldehyde

(1RS,2SR)-1,2-epoxy-3-methylbutyl phenyl sulfone

(1RS,2SR)-1,2-epoxy-3-methylbutyl phenyl sulfone

Conditions
ConditionsYield
With potassium hydroxide In toluene at 20℃; for 3h; Darzens reaction;100%
2-amino-5-chloro-α-(2'-chlorophenyl)benzyl alcohol
74067-45-1

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

isobutyraldehyde
78-84-2

isobutyraldehyde

5-chloro-α-(2-chlorophenyl)-2-(isobutylamino)benzyl alcohol
152906-75-7

5-chloro-α-(2-chlorophenyl)-2-(isobutylamino)benzyl alcohol

Conditions
ConditionsYield
With sodium cyanoborohydride; acetic acid In methanol at 20℃;100%
acetoacetic acid methyl ester
105-45-3

acetoacetic acid methyl ester

isobutyraldehyde
78-84-2

isobutyraldehyde

5-hydroxy-6-methyl-3-oxo-heptanoic acid methyl ester
55848-84-5

5-hydroxy-6-methyl-3-oxo-heptanoic acid methyl ester

Conditions
ConditionsYield
Stage #1: acetoacetic acid methyl ester With sodium hydride In tetrahydrofuran at 0℃; for 0.166667h;
Stage #2: With n-butyllithium In tetrahydrofuran; hexane at 20℃; for 0.333333h;
Stage #3: isobutyraldehyde In tetrahydrofuran; hexane at -78 - 20℃; for 1.08333h;
100%
Stage #1: acetoacetic acid methyl ester With lithium diisopropyl amide In tetrahydrofuran; hexane at -60 - 20℃; for 0.416667h; Weiler method; Inert atmosphere;
Stage #2: isobutyraldehyde In tetrahydrofuran; hexane at -60 - 20℃; for 4h; Weiler method; Inert atmosphere;
Stage #3: With water; ammonium chloride In tetrahydrofuran; hexane Inert atmosphere;
95%
Stage #1: acetoacetic acid methyl ester With sodium hydride In tetrahydrofuran at 0℃;
Stage #2: With n-butyllithium In tetrahydrofuran at -78℃;
Stage #3: isobutyraldehyde In tetrahydrofuran Further stages.;
isobutyraldehyde
78-84-2

isobutyraldehyde

(1-phenyl-2-propen-1-yl)pentamethyl phosphoric triamide
560095-49-0

(1-phenyl-2-propen-1-yl)pentamethyl phosphoric triamide

(4-hydroxy-5-methyl-1-phenyl-1-hexen-1-yl)pentamethyl phosphoric triamide

(4-hydroxy-5-methyl-1-phenyl-1-hexen-1-yl)pentamethyl phosphoric triamide

Conditions
ConditionsYield
Stage #1: (1-phenyl-2-propen-1-yl)pentamethyl phosphoric triamide With n-butyllithium In tetrahydrofuran; hexane at -50℃; for 0.166667h;
Stage #2: isobutyraldehyde In tetrahydrofuran; hexane at -50 - 20℃; for 1h;
100%

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