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Isovaleraldehyde, also known as 3-methylbutyraldehyde, is a colorless liquid with a weak suffocating odor and a pungent odor similar to that of apples. It is a methylbutanal that is butanal substituted by a methyl group at position 3 and occurs as a volatile constituent in various natural sources, including plants and fruits.

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  • 590-86-3 Structure
  • Basic information

    1. Product Name: Isovaleraldehyde
    2. Synonyms: 3-METHYLBUTANAL;3-METHYLBUTYRALDEHYDE;ISOAMYLALDEHYDE;ISOVALERIC ALDEHYDE;ISOVALERALDEHYDE;ISOPENTALDEHYDE;ISO-PENTANAL;FEMA 2692
    3. CAS NO:590-86-3
    4. Molecular Formula: C5H10O
    5. Molecular Weight: 86.13
    6. EINECS: 209-691-5
    7. Product Categories: N/A
    8. Mol File: 590-86-3.mol
    9. Article Data: 226
  • Chemical Properties

    1. Melting Point: -60 °C
    2. Boiling Point: 90 °C(lit.)
    3. Flash Point: 29 °F
    4. Appearance: Clear colorless to light yellow/Liquid
    5. Density: 0.803 g/mL at 25 °C(lit.)
    6. Vapor Density: 2.96 (vs air)
    7. Vapor Pressure: 30 mm Hg ( 20 °C)
    8. Refractive Index: n20/D 1.388(lit.)
    9. Storage Temp.: Refrigerator (+4°C) + Flammables area
    10. Solubility: alcohol: miscible
    11. Explosive Limit: 1.7-6.8%(V)
    12. Water Solubility: 15 g/L (20 ºC)
    13. Stability: Stable, but light and air sensitive. Highly flammable. Readily forms explosive mixtures with air. Incompatible with strong oxidi
    14. Merck: 14,5229
    15. BRN: 773692
    16. CAS DataBase Reference: Isovaleraldehyde(CAS DataBase Reference)
    17. NIST Chemistry Reference: Isovaleraldehyde(590-86-3)
    18. EPA Substance Registry System: Isovaleraldehyde(590-86-3)
  • Safety Data

    1. Hazard Codes: F,Xi
    2. Statements: 11-36-36/37/38-43-36/37
    3. Safety Statements: 7-16-26-36-37/39-37-24-9
    4. RIDADR: UN 1989 3/PG 2
    5. WGK Germany: 1
    6. RTECS: ES3450000
    7. F: 13
    8. TSCA: Yes
    9. HazardClass: 3
    10. PackingGroup: II
    11. Hazardous Substances Data: 590-86-3(Hazardous Substances Data)

590-86-3 Usage

Uses

Used in Artificial Flavors and Perfumes:
Isovaleraldehyde is used as an artificial flavor additive and in perfumes due to its fruity, fatty, animal, and almond-like odor.
Used in the Pharmaceutical Industry:
Isovaleraldehyde acts as a reagent in the preparation of active pharmaceutical ingredient (API) products.
Used in the Food Industry:
Isovaleraldehyde is employed to enhance the taste and odor of food, contributing to its overall quality.
Used in the Wine Industry:
It serves as an internal standard for the determination of wine aroma carbonyl compounds with 5-8 carbon atoms.
Used in the Olive Oil Industry:
Isovaleraldehyde is utilized as a standard to evaluate the quality of olive oils by headspace solid-phase microextraction-gas chromatography using flame ionization detection and multivariate analysis.
Occurrence:
Isovaleraldehyde is found in over 180 natural sources, including apple, banana, berries, grapes, peach, papaya, kohlrabi, carrot, celery, leek, peas, potato, bell pepper, tomato, ginger, peppermint and spearmint oil, vinegar, breads, many cheeses, butter, milk, egg, fatty and lean fish, meats, hop oil, beer, cognac, sherry, rum, grape wines, cocoa, coffee, tea, filberts, peanuts, pecans, peanut butter, barley, oats, soybean, honey, avocado, mace, plum, beans, mushrooms, starfruit, mango, beetroot, cardamom, coriander seed, rice, lovage leaf, pumpkin, buckwheat, laurel, malt, clary sage, wort, elderberry, clam, scallops, crab, crayfish, okra, sapodilla, truffles, and kiwifruit.

Preparation

By oxidation of isoamyl alcohol.

Air & Water Reactions

Highly flammable.

Reactivity Profile

Isovaleraldehyde 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.

Health Hazard

Inhalation causes chest discomfort, nausea, vomiting, and headache. Contact of liquid with eyes or skin causes irritation. Ingestion causes irritation of mouth and stomach.

Check Digit Verification of cas no

The CAS Registry Mumber 590-86-3 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,9 and 0 respectively; the second part has 2 digits, 8 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 590-86:
(5*5)+(4*9)+(3*0)+(2*8)+(1*6)=83
83 % 10 = 3
So 590-86-3 is a valid CAS Registry Number.
InChI:InChI=1/C5H10O/c1-5(2)3-4-6/h4-5H,3H2,1-2H3

590-86-3 Well-known Company Product Price

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  • Alfa Aesar

  • (A19640)  Isovaleraldehyde, 98%   

  • 590-86-3

  • 100ml

  • 355.0CNY

  • Detail
  • Alfa Aesar

  • (A19640)  Isovaleraldehyde, 98%   

  • 590-86-3

  • 250ml

  • 471.0CNY

  • Detail
  • Alfa Aesar

  • (A19640)  Isovaleraldehyde, 98%   

  • 590-86-3

  • 500ml

  • 705.0CNY

  • Detail
  • Alfa Aesar

  • (A19640)  Isovaleraldehyde, 98%   

  • 590-86-3

  • 1000ml

  • 1270.0CNY

  • Detail

590-86-3SDS

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 3-methylbutanal

1.2 Other means of identification

Product number -
Other names Butanal, 3-methyl-

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:590-86-3 SDS

590-86-3Synthetic route

3-methyl-2-buten-1-ol
556-82-1

3-methyl-2-buten-1-ol

isovaleraldehyde
590-86-3

isovaleraldehyde

Conditions
ConditionsYield
With (1,5-cyclooctadiene)(pyridine)(tricyclohexylphosphine)iridium(I) tetrakis[3,5-bis(trifluoromethyl)phenyl]borate; hydrogen In tetrahydrofuran at 23℃; for 0.5h;100%
With [Os(η(5)-C5,κ-N-Cp(N))(CH3CN)2]PF6 In tetrahydrofuran-d8 at 60℃; for 1.33333h; Inert atmosphere;93%
With {(η6-p-cymene)RuCl2}{[3-(3,5-diaza-1-azonia-7-phosphatricyclo[3.3.1.13,7]decan-1-yl)propyl]silanetriyltrioxy} supported on silica-coated ferrite nanoparticles In water at 150℃; under 5171.62 - 6205.94 Torr; for 14h; Inert atmosphere; Microwave irradiation;87%
isopentyl nitrite
110-46-3

isopentyl nitrite

isovaleraldehyde
590-86-3

isovaleraldehyde

Conditions
ConditionsYield
With iron(III) chloride; 1,1,1,3',3',3'-hexafluoro-propanol at 20℃; for 20h; Catalytic behavior; Time; Inert atmosphere;99%
With boron trifluoride diethyl etherate In diethyl ether for 4h; Ambient temperature;91%
With dimethyl sulfoxide at 70℃; for 6h;90.78%
carbon monoxide
201230-82-2

carbon monoxide

isobutene
115-11-7

isobutene

isovaleraldehyde
590-86-3

isovaleraldehyde

Conditions
ConditionsYield
With hydrogen; HSA-Rh(I) In water; pentane at 60℃; under 60800 Torr; for 24h; Hydroformylation;99%
With hydrogen; acetylacetonatodicarbonylrhodium(l); bis-2,6-(2,4-dimethylphenyl)-4-phenylphosphabenzene In toluene at 80℃; under 22501.8 Torr; for 4h;85%
With hydrogen at 100℃; under 18751.9 Torr; for 2h; Inert atmosphere; Autoclave;70%
2-(2-methylpropyl)-1,3-dioxolane
6135-52-0

2-(2-methylpropyl)-1,3-dioxolane

isovaleraldehyde
590-86-3

isovaleraldehyde

Conditions
ConditionsYield
With chloral hydrate In hexane at 25℃; for 1.5h; Inert atmosphere;98%
With tellurium; sodium tetrahydroborate; water 1.) EtOH, 25 deg C, 30 min; Multistep reaction;
i-Amyl alcohol
123-51-3

i-Amyl alcohol

isovaleraldehyde
590-86-3

isovaleraldehyde

Conditions
ConditionsYield
With chromium(VI) oxide; silica gel for 0.05h; microwave irradiation;96%
With diethylammonium chlorochromate; acetic acid In water at 24.84℃; Kinetics; Darkness;96%
In neat (no solvent) at 20℃; for 0.0666667h; Microwave irradiation;94%
3,3-dimethyl acrylaldehyde
107-86-8

3,3-dimethyl acrylaldehyde

isovaleraldehyde
590-86-3

isovaleraldehyde

Conditions
ConditionsYield
96%
With hydrogen; tetra-(n-butyl)ammonium iodide In water at 110℃; under 15001.5 Torr; for 24h; chemoselective reaction;61%
With palladium; isopentanoyl chloride at 190 - 200℃; Hydrogenation;
2-Isobutyl-[1,3]dithiolane

2-Isobutyl-[1,3]dithiolane

isovaleraldehyde
590-86-3

isovaleraldehyde

Conditions
ConditionsYield
With silica gel; copper(II) nitrate In tetrachloromethane for 0.25h; Ambient temperature;96%
isovaleraldoxime
626-90-4

isovaleraldoxime

isovaleraldehyde
590-86-3

isovaleraldehyde

Conditions
ConditionsYield
With N,N'-dichlorobis(2,4,6-trichlorodiphenyl)urea; water In acetonitrile at 20℃; for 0.416667h;96%
C19H24S2

C19H24S2

isovaleraldehyde
590-86-3

isovaleraldehyde

Conditions
ConditionsYield
With 1-benzyl-4-aza-1-azoniabicyclo[2.2.2]octane tribromide In methanol; dichloromethane at 20℃; for 0.133333h;95%
i-Amyl alcohol
123-51-3

i-Amyl alcohol

A

3-methyltetrahydrofuran
13423-15-9

3-methyltetrahydrofuran

B

Isobutyl iodide
513-38-2

Isobutyl iodide

C

isovaleraldehyde
590-86-3

isovaleraldehyde

Conditions
ConditionsYield
With N-iodo-succinimide In chlorobenzene for 2h; Irradiation;A 94%
B 5%
C 1%
i-pentyl bromide
107-82-4

i-pentyl bromide

isovaleraldehyde
590-86-3

isovaleraldehyde

Conditions
ConditionsYield
With dimethyl sulfoxide for 0.0347222h; Kornblum oxidation; Microwave irradiation;93%
With air; water; vanadia at 370 - 400℃; Reagens 4: Bimsstein;
2-(2-methylpropyl)-1,3-dithiane
69824-23-3

2-(2-methylpropyl)-1,3-dithiane

isovaleraldehyde
590-86-3

isovaleraldehyde

Conditions
ConditionsYield
With silica gel; copper(II) nitrate In tetrachloromethane for 0.416667h; Ambient temperature;93%
isopentanoic acid Li-salt

isopentanoic acid Li-salt

isovaleraldehyde
590-86-3

isovaleraldehyde

Conditions
ConditionsYield
With 9-borabicyclo[3.3.1]nonane dimer In tetrahydrofuran for 1h; Ambient temperature;92%
3-Methylbutenoic acid
541-47-9

3-Methylbutenoic acid

isovaleraldehyde
590-86-3

isovaleraldehyde

Conditions
ConditionsYield
Stage #1: 3-Methylbutenoic acid With triethylsilane; decacarbonyldirhenium(0) In diethyl ether at 20℃; for 9h; Inert atmosphere; Schlenk technique; UV-irradiation;
Stage #2: With hydrogenchloride; water In diethyl ether at 20℃; for 3h; Inert atmosphere; Schlenk technique;
91%
isobutyraldehyde oxime
151-00-8

isobutyraldehyde oxime

isovaleraldehyde
590-86-3

isovaleraldehyde

Conditions
ConditionsYield
With water; N-bromobis(p-toluenesulfonyl)amine for 0.0416667h; Microwave irradiation;90%
3-methylbutyric acid
503-74-2

3-methylbutyric acid

isovaleraldehyde
590-86-3

isovaleraldehyde

Conditions
ConditionsYield
With 9-borabicyclo[3.3.1]nonane dimer; lithium dihydrido borata-bicyclo[3.3.0]nonane In tetrahydrofuran for 1h; Ambient temperature;89%
With zinc at 250℃;
With calcium carbonate at 450 - 500℃;
sodium isovalerate
539-66-2

sodium isovalerate

isovaleraldehyde
590-86-3

isovaleraldehyde

Conditions
ConditionsYield
With 9-borabicyclo[3.3.1]nonane dimer In tetrahydrofuran for 1h; Ambient temperature;88%
N-Formylpiperidine
2591-86-8

N-Formylpiperidine

(2-methylpropyl)lithium
920-36-5, 90269-51-5

(2-methylpropyl)lithium

isovaleraldehyde
590-86-3

isovaleraldehyde

Conditions
ConditionsYield
In hexane for 0.166667h; Ambient temperature;77%
isovaleraldehyde phenylhydrazone
18804-59-6

isovaleraldehyde phenylhydrazone

isovaleraldehyde
590-86-3

isovaleraldehyde

Conditions
ConditionsYield
With phosphoric acid for 0.00333333h; microwave irradiation;74%
LEUCINE
328-39-2

LEUCINE

isovaleraldehyde
590-86-3

isovaleraldehyde

Conditions
ConditionsYield
In water pH=7; Neutral conditions; Photolysis; Inert atmosphere; Cooling with ice;73%
With sodium hydroxide; N-bromoacetamide at 35℃; Rate constant;43%
With dipotassium peroxodisulfate; silver nitrate In water at 33℃; Rate constant; Thermodynamic data; Mechanism; ΔE(activ.); ΔH(activ.); ΔS(activ.);
3-Methyl-butanal-

3-Methyl-butanal-

isovaleraldehyde
590-86-3

isovaleraldehyde

Conditions
ConditionsYield
With phosphoric acid for 0.00416667h; microwave irradiation;70%
C6H13N3O

C6H13N3O

isovaleraldehyde
590-86-3

isovaleraldehyde

Conditions
ConditionsYield
With phosphoric acid for 0.00277778h; microwave irradiation;69%
Ethyl isovalerate
108-64-5

Ethyl isovalerate

isovaleraldehyde
590-86-3

isovaleraldehyde

Conditions
ConditionsYield
With lithium-tris(diethylamino)hydridoaluminate In tetrahydrofuran at -78℃; for 3h; Reduction;64%
With sodium tris(diethylamino)aluminum hydride In tetrahydrofuran; dodecane at -78℃; for 8h;62%
2-isopropyloxirane
1438-14-8

2-isopropyloxirane

trimethylsilylmethyllithium
1822-00-0

trimethylsilylmethyllithium

A

4-methyl-(1-trimethylsilanyl)pentan-3-ol

4-methyl-(1-trimethylsilanyl)pentan-3-ol

C

trans-(4-Methyl-2-pentenyl)trimethylsilane
104108-01-2

trans-(4-Methyl-2-pentenyl)trimethylsilane

D

isovaleraldehyde
590-86-3

isovaleraldehyde

Conditions
ConditionsYield
With 2,2,6,6-tetramethylpiperidinyl-lithium In diethyl ether; hexane at 0 - 20℃; for 2h; Product distribution; Further Variations:; Solvents;A 9%
B 5%
C 63%
D 13%
isobutene
115-11-7

isobutene

A

i-Amyl alcohol
123-51-3

i-Amyl alcohol

B

isovaleraldehyde
590-86-3

isovaleraldehyde

Conditions
ConditionsYield
In tolueneA 60%
B n/a
formaldehyd
50-00-0

formaldehyd

isobutene
115-11-7

isobutene

A

4-methyl-3,6-dihydro-2H-pyran
16302-35-5

4-methyl-3,6-dihydro-2H-pyran

B

4-methyl-3,4-dihydro-2H-pyran
2270-61-3

4-methyl-3,4-dihydro-2H-pyran

C

3-methyl-butane-1,3-diol
2568-33-4

3-methyl-butane-1,3-diol

D

methylcyclopentadiene
96-39-9

methylcyclopentadiene

E

3,4,4-trimethylcyclohexene
219811-94-6

3,4,4-trimethylcyclohexene

F

isovaleraldehyde
590-86-3

isovaleraldehyde

G

isoprene
78-79-5

isoprene

Conditions
ConditionsYield
With niobium phosphate at 299.84℃; for 3.33333h; Temperature;A n/a
B n/a
C n/a
D n/a
E n/a
F n/a
G 57%
2-methyl-propan-1-ol
78-83-1

2-methyl-propan-1-ol

isovaleraldehyde
590-86-3

isovaleraldehyde

Conditions
ConditionsYield
Stage #1: With dimethyl sulfoxide In tetrahydrofuran at -30℃; for 0.5h; Swern oxidation;
Stage #2: 2-methyl-propan-1-ol With triethylamine In tetrahydrofuran at -30 - 20℃; Swern oxidation;
40%
propene
187737-37-7

propene

carbon monoxide
201230-82-2

carbon monoxide

A

pentanal
110-62-3

pentanal

B

isovaleraldehyde
590-86-3

isovaleraldehyde

Conditions
ConditionsYield
With rhodium(III) iodide; hydrogen In tetrahydrofuran at 150℃; under 45004.5 Torr; for 3h; Autoclave; Inert atmosphere;A 40%
B 29%
With 2-iodo-propane; rhodium(III) iodide; hydrogen In tetrahydrofuran at 150℃; under 45004.5 Torr; for 3h; Reagent/catalyst; Autoclave; Inert atmosphere;A 24%
B 36%
1-butylene
106-98-9

1-butylene

(Z)-2-Butene
590-18-1

(Z)-2-Butene

trans-2-Butene
624-64-6

trans-2-Butene

Isobutane
75-28-5

Isobutane

carbon monoxide
201230-82-2

carbon monoxide

n-butane
106-97-8

n-butane

A

pentanal
110-62-3

pentanal

B

isovaleraldehyde
590-86-3

isovaleraldehyde

Conditions
ConditionsYield
Stage #1: carbon monoxide With hydrogen; acetylacetonatodicarbonylrhodium(l); C56H44N4O2P2 In toluene at 90℃; under 7500.75 Torr; for 1h;
Stage #2: 1-butylene; (Z)-2-Butene; trans-2-Butene; Isobutane; n-butane In toluene at 90℃; under 12751.3 Torr; for 4h; Product distribution / selectivity;
A 34%
B n/a
Stage #1: carbon monoxide With hydrogen; acetylacetonatodicarbonylrhodium(l); C54H52N4O2P2 In toluene at 90℃; under 7500.75 Torr; for 1h;
Stage #2: 1-butylene; (Z)-2-Butene; trans-2-Butene; Isobutane; n-butane In toluene at 90℃; under 12751.3 Torr; for 4h; Product distribution / selectivity;
A 28%
B n/a
Stage #1: carbon monoxide With hydrogen; acetylacetonatodicarbonylrhodium(l); [5-bis(3-methylindol-1-yl)phosphanyloxy-2,7-di-tert-butyl-9,9-dimethyl-xanthen-4-yl]oxy-bis(3-methylindol-1-yl)phosphane In toluene at 90℃; under 7500.75 Torr; for 1h;
Stage #2: 1-butylene; (Z)-2-Butene; trans-2-Butene; Isobutane; n-butane In toluene at 90℃; under 12751.3 Torr; for 4h; Product distribution / selectivity;
A 37 %Chromat.
B n/a
3-methyl-2-buten-1-ol
556-82-1

3-methyl-2-buten-1-ol

A

2-methyl-1-buten-4-ol
763-32-6

2-methyl-1-buten-4-ol

B

isovaleraldehyde
590-86-3

isovaleraldehyde

Conditions
ConditionsYield
With [Ru(η(5)-C5,κ-N-Cp(N))(CH3CN)2]PF6 In tetrahydrofuran-d8 at 60℃; for 5.33333h; Inert atmosphere;A 31%
B 16%
isovaleraldehyde
590-86-3

isovaleraldehyde

malonic acid dimethyl ester
108-59-8

malonic acid dimethyl ester

dimethyl 2-(3-methylbutylidene)malonate
53618-21-6

dimethyl 2-(3-methylbutylidene)malonate

Conditions
ConditionsYield
With chromatorex NH In toluene at 70℃; Reagent/catalyst; Temperature; Knoevenagel Condensation; Flow reactor; Molecular sieve;100%
With L-proline In dimethyl sulfoxide at 20℃; Reagent/catalyst; Knoevenagel Condensation;97%
With rac-Pro-OH In dimethyl sulfoxide at 20℃; for 16h; Knoevenagel condensation;92%
diethoxyphosphoryl-acetic acid ethyl ester
867-13-0

diethoxyphosphoryl-acetic acid ethyl ester

isovaleraldehyde
590-86-3

isovaleraldehyde

ethyl (E)-5-methylhex-2-enoate
34993-63-0

ethyl (E)-5-methylhex-2-enoate

Conditions
ConditionsYield
Stage #1: diethoxyphosphoryl-acetic acid ethyl ester With sodium hydride In 1,2-dimethoxyethane at 0℃; for 0.416667h;
Stage #2: isovaleraldehyde In 1,2-dimethoxyethane for 16h; Horner-Emmons homologation; Heating;
100%
With n-butyllithium In tetrahydrofuran; hexane at 0℃; for 6h; Wadsworth-Honer-Emmons olefination;95%
With sodium hydride In tetrahydrofuran90%
N-(1-benzylpropyl)-2<(tributylstannyl)methyl>propenamide
101629-94-1

N-(1-benzylpropyl)-2<(tributylstannyl)methyl>propenamide

isovaleraldehyde
590-86-3

isovaleraldehyde

4-Hydroxy-6-methyl-2-methylene-heptanoic acid ((S)-1-benzyl-propyl)-amide
101629-95-2

4-Hydroxy-6-methyl-2-methylene-heptanoic acid ((S)-1-benzyl-propyl)-amide

Conditions
ConditionsYield
With titanium tetrachloride In dichloromethane at -78 - 0℃; for 6h;100%
t-butoxycarbonylhydrazine
870-46-2

t-butoxycarbonylhydrazine

isovaleraldehyde
590-86-3

isovaleraldehyde

N'-(3-methylbutylidene)hydrazinecarboxylic acid tert-butyl ester

N'-(3-methylbutylidene)hydrazinecarboxylic acid tert-butyl ester

Conditions
ConditionsYield
In toluene at 50℃; for 1h;100%
In ethanol for 3h; Heating;81%
5-Trimethylsilanyl-4-trimethylsilanylmethyl-pent-3-enylamine
176848-87-6

5-Trimethylsilanyl-4-trimethylsilanylmethyl-pent-3-enylamine

isovaleraldehyde
590-86-3

isovaleraldehyde

[3-Methyl-but-(E)-ylidene]-(5-trimethylsilanyl-4-trimethylsilanylmethyl-pent-3-enyl)-amine
176848-89-8

[3-Methyl-but-(E)-ylidene]-(5-trimethylsilanyl-4-trimethylsilanylmethyl-pent-3-enyl)-amine

Conditions
ConditionsYield
With 4 A molecular sieve In tetrahydrofuran Ambient temperature;100%
(S)-1-amino-2-(methoxymethyl)pyrrolidine
59983-39-0

(S)-1-amino-2-(methoxymethyl)pyrrolidine

isovaleraldehyde
590-86-3

isovaleraldehyde

((S)-2-Methoxymethyl-pyrrolidin-1-yl)-[3-methyl-but-(E)-ylidene]-amine
72203-95-3

((S)-2-Methoxymethyl-pyrrolidin-1-yl)-[3-methyl-but-(E)-ylidene]-amine

Conditions
ConditionsYield
at 20℃;100%
isovaleraldehyde
590-86-3

isovaleraldehyde

3,6-dibromo-8-methoxyimidazo[1,2-a]pyrazine

3,6-dibromo-8-methoxyimidazo[1,2-a]pyrazine

1-(6-Bromo-8-methoxy-imidazo[1,2-a]pyrazin-3-yl)-3-methyl-butan-1-ol

1-(6-Bromo-8-methoxy-imidazo[1,2-a]pyrazin-3-yl)-3-methyl-butan-1-ol

Conditions
ConditionsYield
Stage #1: 3,6-dibromo-8-methoxyimidazo[1,2-a]pyrazine In tetrahydrofuran; hexane at -75℃; for 0.25h; Metallation;
Stage #2: isovaleraldehyde In tetrahydrofuran; hexane at -75℃; for 0.25h; Addition;
100%
isovaleraldehyde
590-86-3

isovaleraldehyde

(3S)-1-(2-methylpropyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylic acid methyl ester hydrochloride

(3S)-1-(2-methylpropyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylic acid methyl ester hydrochloride

Conditions
ConditionsYield
In toluene for 15h; Pictet-Spengler reaction; Heating;100%
isovaleraldehyde
590-86-3

isovaleraldehyde

(3R)-1-(2-methylpropyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylic acid methyl ester hydrochloride

(3R)-1-(2-methylpropyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylic acid methyl ester hydrochloride

Conditions
ConditionsYield
In toluene for 15h; Pictet-Spengler reaction; Heating;100%
3-Methylbutenoic acid
541-47-9

3-Methylbutenoic acid

tert-butylisonitrile
119072-55-8, 7188-38-7

tert-butylisonitrile

isovaleraldehyde
590-86-3

isovaleraldehyde

1-(tert-butylamino)-4-methyl-1-oxopentan-2-yl 3-methylbut-2-enoate

1-(tert-butylamino)-4-methyl-1-oxopentan-2-yl 3-methylbut-2-enoate

Conditions
ConditionsYield
In water for 0.5h; Passerini reaction; Sonication; Cooling with ice;100%
In water at 25℃; Kinetics; Further Variations:; Solvents; Reagents; Passerini reaction;95%
In water at 20℃; Passerini reaction;86%
In dichloromethane at 25℃; for 18h; Kinetics; Product distribution; Further Variations:; Solvents; Passerini reaction;45%
Pent-4-en-2-ol
111957-98-3, 625-31-0

Pent-4-en-2-ol

isovaleraldehyde
590-86-3

isovaleraldehyde

6-methyl-hept-1-en-4-ol
75863-15-9

6-methyl-hept-1-en-4-ol

Conditions
ConditionsYield
With iron(III) chloride100%
lithium triisopropylsilyl acetylide

lithium triisopropylsilyl acetylide

isovaleraldehyde
590-86-3

isovaleraldehyde

5-methyl-1-triisopropylsilanyl-hex-1-yn-3-ol
913618-91-4

5-methyl-1-triisopropylsilanyl-hex-1-yn-3-ol

Conditions
ConditionsYield
With n-butyllithium In tetrahydrofuran at -78℃;100%
(1S)-1-(2-naphthyl)ethylamine
3082-62-0

(1S)-1-(2-naphthyl)ethylamine

isovaleraldehyde
590-86-3

isovaleraldehyde

(S,E)-N-(3-methylbutylidene)-1-(naphthalen-2-yl)ethanamine

(S,E)-N-(3-methylbutylidene)-1-(naphthalen-2-yl)ethanamine

Conditions
ConditionsYield
With magnesium sulfate In benzene at 0℃; for 2h;100%
nitrobenzene
98-95-3

nitrobenzene

isovaleraldehyde
590-86-3

isovaleraldehyde

N-isopentylaniline
2051-84-5

N-isopentylaniline

Conditions
ConditionsYield
With ammonium formate; palladium on activated charcoal In water; isopropyl alcohol at 20℃; for 0.166667h;100%
With formic acid; Au/TiO2-R In water at 80℃; under 760.051 Torr; for 9h; Inert atmosphere; Green chemistry; chemoselective reaction;85%
Stage #1: nitrobenzene With borane-ammonia complex; Pd/Fe3O4/Pt(111) In methanol at 20℃; under 2068.65 Torr; Flow reactor;
Stage #2: isovaleraldehyde With acetic acid In methanol Flow reactor;
Stage #3: With borane-ammonia complex In methanol Catalytic behavior; Flow reactor;
85%
Stage #1: nitrobenzene With hydrogen In methanol at 20℃; under 760.051 Torr; for 5.5h;
Stage #2: isovaleraldehyde With hydrogen In methanol at 20℃; under 760.051 Torr; for 5h;
75%
With 5% Au/Fe2O3; hydrogen In toluene at 120℃; under 15001.5 Torr; for 6h; Autoclave;58%
O-benzylhydoxylamine hydrochloride
2687-43-6

O-benzylhydoxylamine hydrochloride

isovaleraldehyde
590-86-3

isovaleraldehyde

3-methylbutyraldehyde O-benzyl-oxime
72399-25-8

3-methylbutyraldehyde O-benzyl-oxime

Conditions
ConditionsYield
With pyridine at 80℃; for 2h; Inert atmosphere;100%
With pyridine In ethanol at 20℃; for 4h;86%
In pyridine at 80℃; for 2h;
With sodium acetate In methanol; water at 21 - 24℃; for 2h;
tributyltin methoxide
1067-52-3

tributyltin methoxide

isovaleraldehyde
590-86-3

isovaleraldehyde

(C4H9)3SnOCH(C4H9)OCH3

(C4H9)3SnOCH(C4H9)OCH3

Conditions
ConditionsYield
addn. of tributyltin alkoxide to aldehyde;100%
addn. of tributyltin alkoxide to aldehyde;100%
nitrostyrene
5153-67-3

nitrostyrene

isovaleraldehyde
590-86-3

isovaleraldehyde

(2S,3R)-2-isopropyl-4-nitro-3-phenylbutanal

(2S,3R)-2-isopropyl-4-nitro-3-phenylbutanal

Conditions
ConditionsYield
With : H-D-Pro-Pro-Glu supported on polyethyleneglycol-polystyrene (TentaGel resin) In chloroform; isopropyl alcohol at -15℃; for 72h; optical yield given as %ee; enantioselective reaction;100%
With 4-methyl-morpholine; C16H26N4O5 In neat (no solvent) at 20℃; for 72h; stereoselective reaction;96%
With 4-methyl-morpholine; H-D-Pro-L-Pro-L-Glu-NH2*TFA In chloroform; isopropyl alcohol at 20℃; for 48h; optical yield given as %ee; stereoselective reaction;93%
phlorisobutyrophenone
35458-21-0

phlorisobutyrophenone

5-hydroxy-2,2,6,6-tetramethyl-cyclohex-4-ene-1,3-dione
77744-52-6

5-hydroxy-2,2,6,6-tetramethyl-cyclohex-4-ene-1,3-dione

isovaleraldehyde
590-86-3

isovaleraldehyde

5-hydroxy-2,2,6,6-tetramethyl-4-(3-methyl-1-(2,4,6-trihydroxy-3-isobutyrylphenyl)butyl)cyclohex-4-ene-1,3-dione
1083197-75-4

5-hydroxy-2,2,6,6-tetramethyl-4-(3-methyl-1-(2,4,6-trihydroxy-3-isobutyrylphenyl)butyl)cyclohex-4-ene-1,3-dione

Conditions
ConditionsYield
Stage #1: 5-hydroxy-2,2,6,6-tetramethyl-cyclohex-4-ene-1,3-dione; isovaleraldehyde With piperidine In dichloromethane at 20℃; for 0.25h; Mannich reaction;
Stage #2: With hydrogenchloride; ammonium chloride In water
Stage #3: phlorisobutyrophenone With sodium hydride In tetrahydrofuran at 20℃; for 3h; Friedel Crafts alkylation;
100%
3-Methylbutenoic acid
541-47-9

3-Methylbutenoic acid

p-chlorobenzylisocyanide
39546-47-9

p-chlorobenzylisocyanide

isovaleraldehyde
590-86-3

isovaleraldehyde

C18H25ClN2O2
1262749-10-9

C18H25ClN2O2

Conditions
ConditionsYield
With ammonia In methanol; water at 130℃; for 1.5h; Ugi reaction; Microwave irradiation; microwave tube;100%
4-(difluoromethyl)bicyclo[2.2.2]octan-1-amine
1245643-16-6

4-(difluoromethyl)bicyclo[2.2.2]octan-1-amine

isovaleraldehyde
590-86-3

isovaleraldehyde

4-(difluoromethyl)-N-isopentylbicyclo[2.2.2]octan-1-amine
1257397-61-7

4-(difluoromethyl)-N-isopentylbicyclo[2.2.2]octan-1-amine

Conditions
ConditionsYield
With sodium tris(acetoxy)borohydride In 1,2-dichloro-ethane for 2h;100%
benzylamine
100-46-9

benzylamine

isovaleraldehyde
590-86-3

isovaleraldehyde

E-2-methylpropanal N-benzylimine
22483-21-2

E-2-methylpropanal N-benzylimine

Conditions
ConditionsYield
With magnesium sulfate In dichloromethane at 20℃; Inert atmosphere;100%
2,2-dimethyl-3-butyne
917-92-0

2,2-dimethyl-3-butyne

isovaleraldehyde
590-86-3

isovaleraldehyde

(±)-2,7,7-trimethyloct-5-yn-4-ol
1226968-85-9

(±)-2,7,7-trimethyloct-5-yn-4-ol

Conditions
ConditionsYield
Stage #1: 3,3-Dimethylbut-1-yne With n-butyllithium In tetrahydrofuran at -78℃; for 0.5h; Inert atmosphere;
Stage #2: isovaleraldehyde In tetrahydrofuran at -78 - 20℃; for 1.5h; Inert atmosphere;
100%
Stage #1: 3,3-Dimethylbut-1-yne With n-butyllithium In tetrahydrofuran at -78 - 0℃; for 0.583333h; Inert atmosphere;
Stage #2: isovaleraldehyde In tetrahydrofuran at -78 - 0℃; Inert atmosphere;
(2S)-2-{diphenyl[(trimethylsilyl)oxy]methyl}pyrrolidine
848821-58-9

(2S)-2-{diphenyl[(trimethylsilyl)oxy]methyl}pyrrolidine

(2-nitroethenyl)benzene
102-96-5

(2-nitroethenyl)benzene

isovaleraldehyde
590-86-3

isovaleraldehyde

C31H38N2O3Si

C31H38N2O3Si

Conditions
ConditionsYield
With acetic acid In toluene at 25℃;100%
isovaleraldehyde
590-86-3

isovaleraldehyde

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
25015-63-8

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane

2-(isopentyloxy)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
94845-30-4

2-(isopentyloxy)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Conditions
ConditionsYield
With [HC(CMeN(2,6-(isopropyl)2C6H3)2)]Al(hydride)(triflate) In benzene-d6 at 20℃; for 1h; Inert atmosphere; Sealed tube;100%
With catalyst:C4H9Mg(2,6-iPr2C6H3NCCH3)CH In benzene-d6 pinacolborane reacted with aldehyde in C6D6 at 25°C catalized by nBuMg(2,6-iPrC6H3NCCH3)2CH 0.1-0.5 mol% for <0.5 h;
With 2-H-1,3-di-tert-butyl-2,3-dihydro-1H-1,3,2-diazaphosphole In [D3]acetonitrile at 20℃; for 9h; Catalytic behavior; Inert atmosphere; Sealed tube;88 %Spectr.
1,4-diaminobutane
110-60-1

1,4-diaminobutane

isovaleraldehyde
590-86-3

isovaleraldehyde

N,N-diisopentylbutane-1,4-diamine
1432473-26-1

N,N-diisopentylbutane-1,4-diamine

Conditions
ConditionsYield
With sodium tetrahydroborate In ethanol for 24h;100%
1,5-diaminopentane
462-94-2

1,5-diaminopentane

isovaleraldehyde
590-86-3

isovaleraldehyde

C15H34N2
1432473-25-0

C15H34N2

Conditions
ConditionsYield
With sodium tetrahydroborate In ethanol for 24h;100%
1,6-Hexanediamine
124-09-4

1,6-Hexanediamine

isovaleraldehyde
590-86-3

isovaleraldehyde

C16H36N2
78987-59-4

C16H36N2

Conditions
ConditionsYield
With sodium tetrahydroborate In ethanol for 24h;100%
heptane-1,7-diamine
646-19-5

heptane-1,7-diamine

isovaleraldehyde
590-86-3

isovaleraldehyde

C17H38N2
1432473-24-9

C17H38N2

Conditions
ConditionsYield
With sodium tetrahydroborate In ethanol for 24h;100%
1,8-diaminooctan
373-44-4

1,8-diaminooctan

isovaleraldehyde
590-86-3

isovaleraldehyde

C18H40N2
1432473-23-8

C18H40N2

Conditions
ConditionsYield
With sodium tetrahydroborate In ethanol for 24h;100%

590-86-3Relevant articles and documents

Effective oxidation of alcohols with H5IO6 catalyzed by nickel(II) schiff base complexes

Ramakrishna, Dileep,Bhat, Badekai Ramachandra

, p. 516 - 520 (2010)

Nickel(II)-Schiff base-triphenylphosphine complexes catalyze oxidation of alcohols to carbonyls in presence of minimum amount of periodic acid. The catalytic oxidation was developed in mild conditions and showed good yields. The effects of temperature, time, and concentrations of catalyst and co-oxidant were studied. Higher catalytic activity has been observed for NiL1 compared to the other complexes.Copyright Taylor & Francis Group, LLC.

Effect of CTAB micelle on the oxidation of L-Leucine by N-Bromophthalimide: A kinetic study

Katre, Yokraj,Goyal, Namita,Kumar Singh, Ajaya

, p. 107 - 124 (2011)

The effect of cationic surfactant cetyltrimethylammonium bromide (CTAB) on the oxidation of L-leucine by N-bromophthalimide (NBP) has been studied at 308 K. The reaction exhibits first order dependence on NBP and L-leucine and negative and fractional order dependence on HClO4. The effects of KCl, KBr, phthalimide and mercuric acetate have also been studied and summarized. The rate of reaction increased with an increase in dielectric constant of the medium. CTAB strongly catalyzes the reaction and typical k obs and CTAB profile was observed, i.e., with a progressive increase in CTAB, the reaction rate increased and after achieving a peak kobs decreased at higher concentrations of CTAB. The results are treated quantitatively in terms of "Piszkiewicz" and "Raghvan and Srinivasan's" models. The various activation parameters in presence and absence of CTAB have been also evaluated. A suitable mechanism consistent with the experimental findings has been proposed. The rate constant in micellar phase kM, cooperativity index (n), binding constant (K1 and K2) have been computed. by Oldenbourg Wissenschaftsverlag, Mu?nchen.

Mixed anionic-nonionic micelle catalysed oxidation of aliphatic alcohol in aqueous medium

Acharjee, Animesh,Ali, Md. Ansar,Chowdhury, Suman,Rakshit, Atanu,Saha, Bidyut,Singh, Bula

, (2020)

Oxidation of isoamyl alcohol was carried out under pseudo 1st order reaction condition in aqueous medium by chromic acid. In addition to single micelle, mixed anionic-nonionic micelle (SDS-TX 100) was found to be effective catalyst. Promoters in presence of micelle catalyst showed almost million fold rate acceleration. The product was confirmed by IR and NMR study. UV and NMR analysis were carried out to establish the formation of mixed micelle. Formation of active oxidant was confirmed by fluorescence measurement. Interactions between surfactant and substrate were analysed by NMR spectra. In addition to SDS catalysed Bpy promoted reaction combination of mixed micelle with Bpy promoter was found to show higher rate of oxidation. For single micelle catalysed path the observed rate constants follow the order kobs (SDS) > kobs (TX 100) and kobs (Phen) > kobs (Bpy) > kobs (PA) was observed for promoted reactions. In SDS micelle and mixed micelle kobs (Bpy) > kobs (Phen) > kobs (PA) was observed while in TX 100 micelle kobs (Phen) > kobs (Bpy) > kobs (PA) was found.

Catalytic oxidation of alcohols by nickel(II) Schiff base complexes containing triphenylphosphine in ionic liquid: An attempt towards green oxidation process

Ramakrishna, Dileep,Bhat, Badekai Ramachandra,Karvembu, Ramasamy

, p. 498 - 501 (2010)

A series of square planar nickel(II) complexes containing N,O donor Schiff base ligand, i.e. N-(2-pyridyl)-N′-(5-substituted-salicylidene)hydrazine and triphenylphosphine, have been synthesized and characterized by analytical and spectral methods. Catalytic activities of all the complexes have been studied for the oxidation of alcohols in ionic liquid media using NaOCl as oxidant.

Effective oxidation of alcohols by Iron(III)-Schiff base-triphenylphosphine complexes

Rani, Sandya,Bhat, Badekai Ramachandra

, p. 6403 - 6405 (2010)

Iron(III)-Schiff base-triphenylphosphine complexes catalyze the oxidation of alcohols to their corresponding carbonyl compounds in presence of hydrogen peroxide in good yields.

Isobutene hydroformylation in catalytic systems based on rhodium compounds and polyelectrolytes

Sharikova,Kolesnichenko,Markova,Slivinskii

, p. 701 - 703 (1999)

The catalytic properties of water-soluble systems based on rhodium complexes and polyelectrolytes in isobutene hydroformylation were studied. All of the catalytic systems exhibited an unexpectedly high activity under the conditions where homogeneous hydroformylation virtually did not occur in the presence of conventional rhodium catalysts. A stable catalytic system based on acacRh(CO)2 - PEG complex was proposed, allowing isobutene hydroformylation to be performed with a high activity under mild conditions.

Hydroformylation of olefins in the presence of rhodium carbonyl catalysts immobilized on polymeric pyrrolidinopyridines

Terekhova,Kolesnichenko,Alieva,Markova,Trukhmanova,Slivinsky,Plate

, p. 1583 - 1585 (1996)

The hydroformylation of olefins in the presence of catalytic systems based on RhCl3 and polymeric pyrrolidinopyridines was studied. It was shown that the catalytic system has high activity in the hydroformylation of isobutylene under conditions when the activity of conventional homogeneous catalysts is low. The polymeric catalysts are also thermostable. The effect of solvents on the catalytic properties of the system was studied.

Purification and characterization of isoamyl alcohol oxidase ("Mureka"-forming enzyme)

Yamashita, Nobuo,Motoyoshi, Toru,Nishimura, Akira

, p. 1216 - 1222 (1999)

Isoamyl alcohol oxidase (IAAOD) was purified to apparent homogeneity on SDS-PAGE from ultrafiltration (UF) concentrated sake. IAAOD was a glycoprotein, a monomeric protein with an apparent molecular mass of 73 and 87 kDa, by SDS-PAGE and gel filtration on HPLC, respectively. IAAOD showed high substrate specificity toward C5 branched-chain alkyl alcohol (isoamyl alcohol), and no activity toward shorter (C1-C4) or longer (C7-C10) alkyl alcohols tested. IAAOD was stable between pH 3.0-6.0 at 25°C. The optimum pH was 4.5 at 35°C. Heavy metal ions, p-chloromercuribenzoate (PCMB), hydrazine, and hydroxylamine strongly inhibited the enzyme activity, and an anti-oxidant like L-ascorbate did also. Isovaleraldehyde was produced markedly in pasteurized sake by adding purified IAAOD, therefore, we concluded that it was the enzyme that causes formation of mureka, an off-flavor of sake, the main component of which is isovaleraldehyde.

Aerobic oxidation of alcohols with ruthenium catalysts in ionic liquids

Wolfson, Adi,Wuyts, Stijn,De Vos, Dirk E.,Vankelecom, Ivo F.J.,Jacobs, Pierre A.

, p. 8107 - 8110 (2002)

The aerobic oxidations of aliphatic and aromatic alcohols into the corresponding aldehydes and ketones have been efficiently performed with several ruthenium catalysts in various ammonium salts under low oxygen pressure and without any co-catalyst.

Mechanistic study of [RuCl3(H2O)2OH]- catalyzed oxidation of L-leucine by acidic N-bromophthalimide

Jain, Bhawana,Singh, Ajaya Kumar,Negi, Reena

, p. 1717 - 1728 (2015)

Kinetic studies in homogenous Ru(III) catalyzed oxidation of L-leucine (Leu), by N-bromophthalimide (NBP) in the presence of perchloric acid have been made at 303 K using mercuric acetate as Br- ion scavenger. The reaction follows first-order kinetics with respect to [NBP]. In the lower concentration range of Leu and Ru(III) chloride, the reaction follows first-order kinetics but tends to zero at higher concentration. A positive effect of [Cl-] was observed in the oxidation of Leu. An increase in the rate of reaction with the decrease in dielectric constant of the medium was observed while negative effect was observed for [H+]. The rate of oxidation is unaffected by the change in [phthalimide (NHP)]. Rate of reaction decreased with increase in ionic strength of the medium. The main oxidation products of the reactions were identified as aldehyde, ammonia and CO2 for the oxidation of Leu. From the effect of temperature (298-318 K) on the reaction rate, various activation parameters have been calculated and on the basis of these parameters, a suitable explanation for the reaction mechanism has been given.

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