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123-15-9

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123-15-9 Usage

Description

2-Methylpentanal has an ethereal, fruity odor. This may be prepared from 2-methylpentanol by catalytic oxidation.

Chemical Properties

Colorless liquid. Soluble in water 0.42% by wt, flash p68F (20C) (OC).

Occurrence

Reported found in onion, leek, garlic, milk, roasted peanuts, wheat bread, cooked beef, cured pork, coffee, beer, tea, trassi, rice and mango.

Uses

Different sources of media describe the Uses of 123-15-9 differently. You can refer to the following data:
1. 2-Methylvaleraldehyde is used as an intermediate to manufacture organic compounds (pharmaceuticals, odorants and flavorings)
2. Intermediates for dyes, resins, pharmaceuticals.

Preparation

From 2-methylpentanol by catalytic oxidation.

Aroma threshold values

Detection: 1.6 to 3.2 ppb

Taste threshold values

Taste characteristics at 5.0 ppm: vegetative and green with a fruity, grape-like nuance.

Synthesis Reference(s)

Synthesis, p. 717, 1985 DOI: 10.1055/s-1985-31327

General Description

A colorless liquid. Less dense than water. Flash point near 50°F. Used to make rubber and artificial flavorings.

Air & Water Reactions

Highly flammable. Slightly soluble in water.

Reactivity Profile

Methyl valeraldehyde 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

Flammable, dangerous fire risk. Strong irri-tant to skin and mucous membranes.

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.

Flammability and Explosibility

Highlyflammable

Check Digit Verification of cas no

The CAS Registry Mumber 123-15-9 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,2 and 3 respectively; the second part has 2 digits, 1 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 123-15:
(5*1)+(4*2)+(3*3)+(2*1)+(1*5)=29
29 % 10 = 9
So 123-15-9 is a valid CAS Registry Number.
InChI:InChI=1/C6H12O/c1-3-4-6(2)5-7/h5-6H,3-4H2,1-2H3/t6-/m0/s1

123-15-9 Well-known Company Product Price

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  • CAS number
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  • Alfa Aesar

  • (B24199)  2-Methylvaleraldehyde, 98%   

  • 123-15-9

  • 100g

  • 397.0CNY

  • Detail
  • Alfa Aesar

  • (B24199)  2-Methylvaleraldehyde, 98%   

  • 123-15-9

  • 500g

  • 1103.0CNY

  • Detail

123-15-9SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name Methyl Valeraldehyde

1.2 Other means of identification

Product number -
Other names Pentanal, 2-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:123-15-9 SDS

123-15-9Synthetic route

2-methylpentan-1-ol
105-30-6

2-methylpentan-1-ol

2-methylvaleraldehyde
123-15-9

2-methylvaleraldehyde

Conditions
ConditionsYield
With 1-methyl-1H-imidazole; [2,2]bipyridinyl; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; tetrakis(acetonitrile)copper(I)tetrafluoroborate; oxygen In acetonitrile at 20℃; for 11h;98%
With 1-methyl-1H-imidazole; [2,2]bipyridinyl; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; tetrakisacetonitrile copper(I) trifluoromethanesulfonate; oxygen In acetonitrile at 20℃; for 11h;98%
With manganese(II) nitrate; C70H128N16O4; oxygen; cobalt(II) nitrate In acetic acid at 25℃; for 1h; Mechanism;97%
1-penten
109-67-1

1-penten

carbon monoxide
201230-82-2

carbon monoxide

A

2-methylvaleraldehyde
123-15-9

2-methylvaleraldehyde

B

hexanal
66-25-1

hexanal

Conditions
ConditionsYield
With acetylacetonatodicarbonylrhodium(l); hydrogen; triphenylphosphine In neat (no solvent) at 80℃; under 7500.75 Torr; for 1h; Catalytic behavior; Time; Autoclave;A 11.1%
B 83.7%
With hydrogen; (polymer-PPh2)2Ru(CO)3 In benzene at 140℃; under 51714.8 Torr; for 20h; Product distribution; further temperature, pressure; other catalysts;
With water; dodecacarbonyltetrairidium In methanol at 150℃; under 41371.8 Torr; for 0.5h; Product distribution; other group 8 transition-metal catalysts;
1-Methoxy-2-methyl-pentan-2-ol
35155-59-0

1-Methoxy-2-methyl-pentan-2-ol

2-methylvaleraldehyde
123-15-9

2-methylvaleraldehyde

Conditions
ConditionsYield
With phosphoric acid at 100℃; for 3h;83%
(E)-2-methylpent-2-enal
623-36-9

(E)-2-methylpent-2-enal

A

2-methylpent-2-enoic acid
16957-70-3

2-methylpent-2-enoic acid

B

2-methylvaleraldehyde
123-15-9

2-methylvaleraldehyde

C

(S)-2-methylpentanoic acid
1187-82-2

(S)-2-methylpentanoic acid

Conditions
ConditionsYield
With aldehyde dehydrogenase from E.coli; ene-reductase from Saccharomyces cerevisiae; NADH In aq. phosphate buffer at 30℃; for 0.75h; pH=7; Enzymatic reaction; stereoselective reaction;A 13%
B 6%
C 77%
propionaldehyde
123-38-6

propionaldehyde

A

propan-1-ol
71-23-8

propan-1-ol

B

2-methylpentan-1-ol
105-30-6

2-methylpentan-1-ol

C

2-methyl-2-pentenal
14250-96-5, 16958-22-8, 623-36-9

2-methyl-2-pentenal

D

2-methylvaleraldehyde
123-15-9

2-methylvaleraldehyde

Conditions
ConditionsYield
With hydrogen; aluminum oxide; nickel; molybdenum at 180℃; under 51714.8 Torr; Product distribution; Further Variations:; Catalysts; Temperatures;A 69.1%
B 12.3%
C 1%
D 7.9%
2-Methylpentanoic acid
97-61-0, 22160-39-0

2-Methylpentanoic acid

2-methylvaleraldehyde
123-15-9

2-methylvaleraldehyde

Conditions
ConditionsYield
With isobutylmagnesium bromide; bis(cyclopentadienyl)titanium dichloride In diethyl ether for 4h; Ambient temperature;65%
With hydrogen; 2,2-dimethylpropanoic anhydride; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran at 80℃; under 22501.8 Torr; for 24h;64 % Spectr.
With hydrogen; 2,2-dimethylpropanoic anhydride; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran at 80℃; under 22501.8 Torr; for 24h;64 % Spectr.
2,2,6,6-tetramethyl-1-(pent-1-enyl)piperidine

2,2,6,6-tetramethyl-1-(pent-1-enyl)piperidine

methyl iodide
74-88-4

methyl iodide

2-methylvaleraldehyde
123-15-9

2-methylvaleraldehyde

Conditions
ConditionsYield
Stage #1: 2,2,6,6-tetramethyl-1-(pent-1-enyl)piperidine; methyl iodide In [D3]acetonitrile for 3h;
Stage #2: With water; sodium acetate; acetic acid
30%
(E)-2-methylpent-2-enal
623-36-9

(E)-2-methylpent-2-enal

A

2-methylpent-2-enoic acid
16957-70-3

2-methylpent-2-enoic acid

B

2-Methylpentanoic acid
97-61-0, 22160-39-0

2-Methylpentanoic acid

C

2-methylvaleraldehyde
123-15-9

2-methylvaleraldehyde

Conditions
ConditionsYield
With aldehyde dehydrogenase from E.coli; ene-reductase from Saccharomyces cerevisiae; NADH In aq. phosphate buffer at 30℃; for 0.5h; pH=7; Time; Enzymatic reaction;A 11%
B 29%
C 8%
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%
2-bromopentane
107-81-3

2-bromopentane

2-methylvaleraldehyde
123-15-9

2-methylvaleraldehyde

Conditions
ConditionsYield
In acetonitrile Ambient temperature; electrochemical synthesis: divided cell, Pt plate electrodes, -2.30 V vs Ag/Ag(+), Br as supporting electrolyte;5%
propan-1-ol
71-23-8

propan-1-ol

2-methylvaleraldehyde
123-15-9

2-methylvaleraldehyde

Conditions
ConditionsYield
With aluminum oxide; silver at 250℃;
3-methyl-3-propyl-oxiranecarboxylic acid ethyl ester
66520-51-2

3-methyl-3-propyl-oxiranecarboxylic acid ethyl ester

2-methylvaleraldehyde
123-15-9

2-methylvaleraldehyde

Conditions
ConditionsYield
With sodium hydroxide Versetzen der Reaktionsloesung mit Schwefelsaeure und Erhitzen des Reaktionsprodukts bis auf 200grad;
(i) NaOH, (ii) H+, (iii) (decarboxylation); Multistep reaction;
2-methylpentan-1-ol
105-30-6

2-methylpentan-1-ol

A

2-methylvaleraldehyde
123-15-9

2-methylvaleraldehyde

B

2-methylpentyl 2-methylpentanoate
90397-38-9

2-methylpentyl 2-methylpentanoate

Conditions
ConditionsYield
With sodium dichromate; sulfuric acid

A

2-methylpentan-1-ol
105-30-6

2-methylpentan-1-ol

B

2-methylvaleraldehyde
123-15-9

2-methylvaleraldehyde

Conditions
ConditionsYield
at 200℃; Druckhydrierung an Nickel-Kieselgur;

A

2-methyl-pent-2-en-1-ol
1610-29-3

2-methyl-pent-2-en-1-ol

B

2-methylvaleraldehyde
123-15-9

2-methylvaleraldehyde

Conditions
ConditionsYield
With ethanol; hydrogen; palladium
2-methylvaleraldehyde
123-15-9

2-methylvaleraldehyde

Conditions
ConditionsYield
With acetic acid
With ethanol; palladium Hydrogenation;
With nickel In diethyl ether
1-ethoxy-2-methyl-pentan-2-ol

1-ethoxy-2-methyl-pentan-2-ol

oxalic acid
144-62-7

oxalic acid

2-methylvaleraldehyde
123-15-9

2-methylvaleraldehyde

(E)-2-methylpent-2-enal
623-36-9

(E)-2-methylpent-2-enal

2-methylvaleraldehyde
123-15-9

2-methylvaleraldehyde

Conditions
ConditionsYield
With nickel Hydrogenation;
With hydrogen; palladium on activated charcoal In diethyl ether for 24h;
With glucose dehydrogenase; β-D-glucose; ene-reductase from Enterobacter cloacae; NADH In aq. phosphate buffer at 30℃; for 1h; pH=7; Reagent/catalyst; Enzymatic reaction;
allyl alcohol
107-18-6

allyl alcohol

A

2-methylvaleraldehyde
123-15-9

2-methylvaleraldehyde

B

(E)-2-methylpent-2-enal
623-36-9

(E)-2-methylpent-2-enal

Conditions
ConditionsYield
With sodium hydroxide; pentacarbonyl iron
diethylborinic acid (E)-2-methyl-pent-1-enyl ester
58495-79-7

diethylborinic acid (E)-2-methyl-pent-1-enyl ester

2-methylvaleraldehyde
123-15-9

2-methylvaleraldehyde

Conditions
ConditionsYield
In methanol
1-iodo-propane
107-08-4

1-iodo-propane

N-cyclohexylpropionaldimine
1195-49-9

N-cyclohexylpropionaldimine

2-methylvaleraldehyde
123-15-9

2-methylvaleraldehyde

Conditions
ConditionsYield
(i) EtMgBr, THF, (ii) /BRN= 505937/; Multistep reaction;
ethyl-phenyl-borinic acid (E)-2-methyl-pent-1-enyl ester
60218-03-3

ethyl-phenyl-borinic acid (E)-2-methyl-pent-1-enyl ester

2-methylvaleraldehyde
123-15-9

2-methylvaleraldehyde

Conditions
ConditionsYield
With acetylacetone at 80℃;
2-Methylpentanoic acid
97-61-0, 22160-39-0

2-Methylpentanoic acid

formic acid ethyl ester
109-94-4

formic acid ethyl ester

2-methylvaleraldehyde
123-15-9

2-methylvaleraldehyde

Conditions
ConditionsYield
(i) LDA, (ii) /BRN= 906769/, aq. HCl; Multistep reaction;
pentanal
110-62-3

pentanal

methyl iodide
74-88-4

methyl iodide

2-methylvaleraldehyde
123-15-9

2-methylvaleraldehyde

Conditions
ConditionsYield
(i) iBu2NH, benzene, (ii) /BRN= 969135/, MeCN; Multistep reaction;
diisobutyl-pent-1-enyl-amine
42298-81-7

diisobutyl-pent-1-enyl-amine

methyl iodide
74-88-4

methyl iodide

2-methylvaleraldehyde
123-15-9

2-methylvaleraldehyde

Conditions
ConditionsYield
(i) benzene, (ii) aq. NaOAc, AcOH; Multistep reaction;
butyl-isobutyl-pent-1-enyl-amine
53516-60-2

butyl-isobutyl-pent-1-enyl-amine

methyl iodide
74-88-4

methyl iodide

2-methylvaleraldehyde
123-15-9

2-methylvaleraldehyde

Conditions
ConditionsYield
In acetonitrile
formic acid
64-18-6

formic acid

sec-amyl magnesium bromide
57325-22-1

sec-amyl magnesium bromide

2-methylvaleraldehyde
123-15-9

2-methylvaleraldehyde

Conditions
ConditionsYield
With ethylmagnesium bromide 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;
1-penten
109-67-1

1-penten

A

2-methylpentan-1-ol
105-30-6

2-methylpentan-1-ol

B

2-methylvaleraldehyde
123-15-9

2-methylvaleraldehyde

C

hexanal
66-25-1

hexanal

D

hexan-1-ol
111-27-3

hexan-1-ol

Conditions
ConditionsYield
With carbon monoxide; hydrogen; 3*Co(CO)8 In octane at 180℃; under 24823.1 - 26374.6 Torr; for 14h; Product distribution; n-Pentadecane;
2-methylvaleraldehyde
123-15-9

2-methylvaleraldehyde

di-isopropyl azodicarboxylate
2446-83-5

di-isopropyl azodicarboxylate

diisopropyl 1-(2-methylpentanoyl) hydrazine-1,2-dicarboxylate

diisopropyl 1-(2-methylpentanoyl) hydrazine-1,2-dicarboxylate

Conditions
ConditionsYield
With Graphite In acetonitrile at 20℃; for 2h; Irradiation;100%
With Benzoylformic acid In Petroleum ether at 20℃; Irradiation; Green chemistry;
2-methylvaleraldehyde
123-15-9

2-methylvaleraldehyde

2-Methylpentanoic acid
97-61-0, 22160-39-0

2-Methylpentanoic acid

Conditions
ConditionsYield
With C4H11FeMo6NO24(3-)*3C16H36N(1+); water; oxygen; sodium carbonate at 50℃; under 760.051 Torr; for 8h; Green chemistry;99%
With 4H3N*4H(1+)*CuMo6O18(OH)6(4-); water; oxygen; sodium carbonate at 50℃; under 760.051 Torr; for 12h;99%
With 2-mesityl-6,7-dihydro-5H-pyrrolo[2,1-c][1,2,4]triazol-2-ium tetrafluoroborate; 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine In acetonitrile at 20℃;80%
2-methylvaleraldehyde
123-15-9

2-methylvaleraldehyde

S-<1-(3,6,9-trioxadecyl)benzimidazol-2-yl>hexanethioate
75177-82-1

S-<1-(3,6,9-trioxadecyl)benzimidazol-2-yl>hexanethioate

A

Hexanoic acid (Z)-2-methyl-pent-1-enyl ester
344400-74-4

Hexanoic acid (Z)-2-methyl-pent-1-enyl ester

B

1-{2-[2-(2-Methoxy-ethoxy)-ethoxy]-ethyl}-1,3-dihydro-benzoimidazole-2-thione

1-{2-[2-(2-Methoxy-ethoxy)-ethoxy]-ethyl}-1,3-dihydro-benzoimidazole-2-thione

Conditions
ConditionsYield
With cesium fluoride In N,N-dimethyl-formamide; benzene for 48h; Ambient temperature;A 97%
B n/a
1-hydroxy-pyrrolidine-2,5-dione
6066-82-6

1-hydroxy-pyrrolidine-2,5-dione

2-methylvaleraldehyde
123-15-9

2-methylvaleraldehyde

2,5-dioxopyrrolidin-1-yl 2-methylpentanoate

2,5-dioxopyrrolidin-1-yl 2-methylpentanoate

Conditions
ConditionsYield
With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In ethyl acetate for 2h; Heating;97%
2-methylvaleraldehyde
123-15-9

2-methylvaleraldehyde

trimethylsilylacetylene
1066-54-2

trimethylsilylacetylene

dibenzylamine
103-49-1

dibenzylamine

C25H35NSi

C25H35NSi

Conditions
ConditionsYield
With (S)-1-(2-(diphenylphosphanyl)naphthalen-1-yl)isoquinoline; copper(I) bromide In toluene at 20℃; for 43h; Schlenk technique; Inert atmosphere; Molecular sieve; enantioselective reaction;97%
2-methylvaleraldehyde
123-15-9

2-methylvaleraldehyde

benzo[1,3,2]dioxaborole
274-07-7

benzo[1,3,2]dioxaborole

C12H17BO3

C12H17BO3

Conditions
ConditionsYield
With [[{(2,6-iPr2C6H3N)P(Ph2)}2N]AlH]+[HB(C6F5)3]- In toluene at 20℃; for 3h; Schlenk technique; Glovebox;97%
N-methylmaleimide
930-88-1

N-methylmaleimide

2-methylvaleraldehyde
123-15-9

2-methylvaleraldehyde

2-methyl-2-(1-methyl-2,5-dioxopyrrolidin-3-yl)pentanal

2-methyl-2-(1-methyl-2,5-dioxopyrrolidin-3-yl)pentanal

Conditions
ConditionsYield
With L-isoleucine; potassium hydroxide In chloroform at 25℃; for 14h; Michael Addition; stereoselective reaction;96%
nitromethane
75-52-5

nitromethane

2-methylvaleraldehyde
123-15-9

2-methylvaleraldehyde

3-methyl-1-nitro-2-hexanol
1035694-84-8

3-methyl-1-nitro-2-hexanol

Conditions
ConditionsYield
Stage #1: nitromethane; 2-methylvaleraldehyde With sodium hydroxide In ethanol; water at 4 - 20℃;
Stage #2: With hydrogenchloride In water pH=~ 7;
94.2%
With potassium fluoride In isopropyl alcohol at 20℃; for 14h;62%
2-methylvaleraldehyde
123-15-9

2-methylvaleraldehyde

n-butyl magnesium chloride

n-butyl magnesium chloride

(+/-)-4-Methyl-5-nonanol

(+/-)-4-Methyl-5-nonanol

Conditions
ConditionsYield
With hydrogenchloride In tetrahydrofuran; water93.3%
2-methylvaleraldehyde
123-15-9

2-methylvaleraldehyde

((E)-2-Methyl-pent-1-enyl)-[2-methyl-pent-(E)-ylidene]-amine

((E)-2-Methyl-pent-1-enyl)-[2-methyl-pent-(E)-ylidene]-amine

Conditions
ConditionsYield
With 1,1,1,3,3,3-hexamethyl-disilazane; cobalt(II) bromide at 110℃; for 6h;93%
C6H4NCH2CHCCH2
491-35-0

C6H4NCH2CHCCH2

2-methylvaleraldehyde
123-15-9

2-methylvaleraldehyde

4-methyl-2-(pentan-2-yl)quinoline
93845-95-5

4-methyl-2-(pentan-2-yl)quinoline

Conditions
ConditionsYield
With toluene-4-sulfonic acid; sodium bromide In water; 1,2-dichloro-ethane at 20℃; for 18h; Irradiation; Green chemistry;93%
With trifluorormethanesulfonic acid; [4,4’-bis(1,1-dimethylethyl)-2,2’-bipyridine-N1,N1‘]bis [3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-N]phenyl-C]iridium(III) hexafluorophosphate; ammonium bromide In toluene at 60℃; for 22h; Irradiation; Inert atmosphere;32%
2-methylvaleraldehyde
123-15-9

2-methylvaleraldehyde

S-tert-butylsulfinimide
146374-27-8

S-tert-butylsulfinimide

2-methyl-N-(2-methylpentylidene)propane-2-sulfinamide

2-methyl-N-(2-methylpentylidene)propane-2-sulfinamide

Conditions
ConditionsYield
With benzyl bromide; zinc In tetrahydrofuran at 20℃;91%
N-cyclohexylmaleimide
1631-25-0

N-cyclohexylmaleimide

2-methylvaleraldehyde
123-15-9

2-methylvaleraldehyde

2-(1-cyclohexyl-2,5-dioxopyrrolidin-3-yl)-2-methylpentanal

2-(1-cyclohexyl-2,5-dioxopyrrolidin-3-yl)-2-methylpentanal

Conditions
ConditionsYield
With L-isoleucine; potassium hydroxide In chloroform at 25℃; for 40h; Michael Addition; stereoselective reaction;91%
2-methylvaleraldehyde
123-15-9

2-methylvaleraldehyde

2,4,6-Tris-(1-methyl-butyl)-[1,3,5]trioxane

2,4,6-Tris-(1-methyl-butyl)-[1,3,5]trioxane

Conditions
ConditionsYield
methyltrioxorhenium(VII) for 144h;90%
2-methylvaleraldehyde
123-15-9

2-methylvaleraldehyde

[((4-methoxy-2-methylbutan-2-yl)oxy)diphenylsilyl]methyl phenyl sulfone

[((4-methoxy-2-methylbutan-2-yl)oxy)diphenylsilyl]methyl phenyl sulfone

(Z)-1-(phenylsulfonyl)-3-methylhex-1-ene

(Z)-1-(phenylsulfonyl)-3-methylhex-1-ene

Conditions
ConditionsYield
Stage #1: [((4-methoxy-2-methylbutan-2-yl)oxy)diphenylsilyl]methyl phenyl sulfone With lithium hexamethyldisilazane at 0℃; for 0.25h; Peterson Olefination; Inert atmosphere;
Stage #2: 2-methylvaleraldehyde at 0℃; for 2h; Peterson Olefination; Inert atmosphere; stereoselective reaction;
90%
2-methylvaleraldehyde
123-15-9

2-methylvaleraldehyde

2-methylpentyl 2-methylpentanoate
90397-38-9

2-methylpentyl 2-methylpentanoate

Conditions
ConditionsYield
With trimethylaluminum; benzene-1,2-diol; isopropyl alcohol In dichloromethane at 20℃; for 2h;89%
N-Ethylmaleimide
128-53-0

N-Ethylmaleimide

2-methylvaleraldehyde
123-15-9

2-methylvaleraldehyde

2-(1-ethyl-2,5-dioxopyrrolidin-3-yl)-2-methylpentanal

2-(1-ethyl-2,5-dioxopyrrolidin-3-yl)-2-methylpentanal

Conditions
ConditionsYield
With L-isoleucine; potassium hydroxide In chloroform at 25℃; for 35h; Michael Addition; stereoselective reaction;89%
2-methylvaleraldehyde
123-15-9

2-methylvaleraldehyde

ethyl acrylate
140-88-5

ethyl acrylate

4-(2-pentyl)butyrolactone

4-(2-pentyl)butyrolactone

Conditions
ConditionsYield
With borax; disodium hydrogenphosphate; ethylenediaminetetraacetic acid; bis(dibutylethyl)hexamethylenediammonium hydroxide; triethylamine In water at 25℃; pH=10; Electrochemical reaction;88.4%
2-methylvaleraldehyde
123-15-9

2-methylvaleraldehyde

di-isopropyl azodicarboxylate
2446-83-5

di-isopropyl azodicarboxylate

(+)-2-[N,N'-bis(isopropanoxycarbonyl)hydrazino]-2-(n-propyl)-propionaldehyde
1256965-86-2

(+)-2-[N,N'-bis(isopropanoxycarbonyl)hydrazino]-2-(n-propyl)-propionaldehyde

Conditions
ConditionsYield
With L-3-(naphthalen-1-yl)alanine hydrochloride In tetrahydrofuran at 0℃; for 15h;88%
With (S)-N-((1R,2R)-2-(3-(3,5-bis(trifluoromethyl)phenyl)thioureido)cyclohexyl)pyrrolidine-2-carboxamide; salicylic acid In dichloromethane at 0℃; for 45h; enantioselective reaction;
2-methylvaleraldehyde
123-15-9

2-methylvaleraldehyde

2-methylpentanamide
6941-49-7

2-methylpentanamide

Conditions
ConditionsYield
Stage #1: 2-methylvaleraldehyde With hydroxylamine hydrochloride In dimethyl sulfoxide at 100℃;
Stage #2: With water; dihydrogen peroxide; sodium hydroxide In dimethyl sulfoxide
87%
With trimethylsilylazide; tetrabutylammomium bromide; iron(II) bromide In neat (no solvent) at 60℃; for 4h; Irradiation;70%
2-methylvaleraldehyde
123-15-9

2-methylvaleraldehyde

Diethyl phosphonate
762-04-9, 123-22-8

Diethyl phosphonate

(1-Hydroxy-2-methyl-pentyl)-phosphonic acid diethyl ester
145459-48-9

(1-Hydroxy-2-methyl-pentyl)-phosphonic acid diethyl ester

Conditions
ConditionsYield
triethylamine Ambient temperature;86.1%
isoquinoline
119-65-3

isoquinoline

2-methylvaleraldehyde
123-15-9

2-methylvaleraldehyde

1-(pentan-2-yl)isoquinoline

1-(pentan-2-yl)isoquinoline

Conditions
ConditionsYield
With di-tert-butyl peroxide In 1,2-dichloro-benzene at 130℃; for 12h; Minisci Aromatic Substitution; Sealed tube; regioselective reaction;86%
Stage #1: isoquinoline With trifluoroacetic acid In 1,2-dichloro-ethane at 20℃; for 0.0833333h;
Stage #2: 2-methylvaleraldehyde With oxygen In 1,2-dichloro-ethane at 0 - 115℃; under 760.051 Torr; for 16h;
60%
pyrid-2-ylhydrazine
4930-98-7

pyrid-2-ylhydrazine

2-methylvaleraldehyde
123-15-9

2-methylvaleraldehyde

3-(pentan-2-yl)-[1,2,4]triazolo[4,3-a]pyridine

3-(pentan-2-yl)-[1,2,4]triazolo[4,3-a]pyridine

Conditions
ConditionsYield
Stage #1: pyrid-2-ylhydrazine; 2-methylvaleraldehyde In acetic acid at 20℃; for 0.0833333h;
Stage #2: With chromium(VI) oxide In acetic acid at 110℃; for 0.25h;
86%
Multi-step reaction with 2 steps
1: acetonitrile / 20 °C / Green chemistry
2: tetrabutylammonium tetrafluoroborate / acetonitrile; water / 4 h / 70 °C / Electrolysis; Green chemistry
View Scheme
2-methylvaleraldehyde
123-15-9

2-methylvaleraldehyde

5-nitro-2-pentanone
22020-87-7

5-nitro-2-pentanone

5-nitro-6-hydroxy-7-methyldecan-2-one

5-nitro-6-hydroxy-7-methyldecan-2-one

Conditions
ConditionsYield
With sodium hydroxide; cetyltrimethylammonium chloride for 2h; Ambient temperature;85%
2-methylvaleraldehyde
123-15-9

2-methylvaleraldehyde

2-methyl-Pentanenitrile
6339-13-5

2-methyl-Pentanenitrile

Conditions
ConditionsYield
With hydroxylamine hydrochloride; sodium iodide In acetonitrile for 1.5h; Heating;85%
With hydroxylamine hydrochloride In dimethyl sulfoxide at 100℃; for 1h;71%
2-methylvaleraldehyde
123-15-9

2-methylvaleraldehyde

1-nitro-4-(2-nitrovinyl)benzene
3156-41-0

1-nitro-4-(2-nitrovinyl)benzene

C14H18N2O5

C14H18N2O5

Conditions
ConditionsYield
With 1-((1R,2R)-2-aminocyclohexyl)-3-(((1R,4aS,10ar)-7-isopropyl-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octahydrophenanthren-1-yl)methyl)thiourea In dichloromethane at 25℃; for 48h; Michael Addition; stereoselective reaction;85%
8-methyl-2-phenylimidazo[1,2-a]pyridine
885-89-2

8-methyl-2-phenylimidazo[1,2-a]pyridine

2-methylvaleraldehyde
123-15-9

2-methylvaleraldehyde

8-methyl-5-(pentan-2-yl)-2-phenylimidazo[1,2-a]pyridine

8-methyl-5-(pentan-2-yl)-2-phenylimidazo[1,2-a]pyridine

Conditions
ConditionsYield
With di-tert-butyl peroxide; manganese(II) acetate In 1,2-dichloro-benzene at 130℃; for 6h; Inert atmosphere; Sealed tube;84%

123-15-9Relevant articles and documents

-

Jardine,Wilkinson

, p. 270 (1967)

-

Modification of rhodium catalyst with stibines for hydroformylation of 1-pentene

Sharma, Pankaj,Arias, Jose Luis,Vasquez, Jaime,Gomez, Valente,Guiterrez, Rene

, p. 681 - 684 (2007)

Homogeneous hydroformylation of 1-pentene under synthesis gas experimental conditions was studied using RhClCO(PPh3)2 complex with different triarylstibines. Three different stibine ligands SbR3 [where R = 2,4,6-mesityl (TMS), 2-furyl (TFS), 2-N,N-dimethylbenzylamine (TDMBAS)], have been tested. It is interesting to note that 2:1 addition of these stibine ligands to the RhClCO(PPh3)2 complex catalyst increases the aldehydes yields with an appreciable n:iso ratio. The catalytic activity of the system shows a TDMBAS > TMS > TFS pattern which indicates that not only basicity of the ligand alone is playing a role in the activity but the steric effect is also very important, and it is combination of these two factors that contributes to the resulting catalytical activity. The maximum yield of aldehydes obtained were 98.7% with n/iso = 1.4 when RhClCO(PPh3)2 + TFS system was used and 93.7% with n/iso = 2.43 when TDMBAS ligand was studied.

1-Pentene Hydroformylation Catalyzed by Polymer-Bound Ruthenium Complexes

Pittman, Charles U.,Wilemon, Gary M.

, p. 1901 - 1905 (1981)

Polymer-bound ruthenium hydroformylation catalysts were prepared by reacting diphenylphosphinated styrene-1percent divinylbenzene resins with Ru(CO)3(PPh3)2 under a carbon monoxide atmosphere.Resins with 29percent and 5percent ring-substitution loading levels of phosphine were prepared, and resins with P/Ru ratios of 3.1, 6.7, and 11.3 were made with the 29percent phosphine loading.These resins functioned as 1-pentene hydroformylation catalysts and were compared to the homogeneous use of Ru(CO)3(PPh3)2 as the catalyst.No olefin isomerization occured.The resin catalysts with P/Ru ratios of 3.1 and 6.7 at 29percent loading gave higher n/b aldehyde selectivities (3.5-3.8) than the homogeneous catalyst when employed at P/Ru ratios of 20 but not as high as was achieved by using Ru(CO)3(PPh3)2 in molten PPh3 (5.1).The n/b selectivity was discussed in terms of the equilibrium between (polymer-PPh2)2RuH2(alkene)(CO) and polymer-PPh2RuH2(alkene)(CO)2 within the resin matrix where phosphine loading, P/Ru, ligand mobility, and swelling play contributing roles.The novel 1,1'-bis(diphenylphosphino)ferrocene ligand induced higher n/b selectivities than PPh3 in homogeneous Ru-catalyzed reactions.

Recycling of two molecular catalysts in the hydroformylation/aldol condensation tandem reaction using one multiphase system

Leitner, Walter,Strohmann, Marc,Vorholt, Andreas J.,Vossen, Jeroen T.

, p. 8444 - 8451 (2020)

Tandem reactions are of great importance to efficiently execute multiple conversions in one synthesis step. Herein we present a multiphase system for the hydroformylation/aldol condensation, which is able to recycle both optimized catalysts multiple times. The system consists of an organometallic rhodium/sulfoXantphos hydroformylation catalyst and basic NaOH as aldol condensation initiator, which are both immobilized in a polyethylene glycol phase. Under reaction conditions, NaOH is converted to sodium formate, which is still able to catalyse the aldol condensation. The reaction and recycling are demonstrated by the conversion of 1-pentene to the corresponding aldol product in a recycling experiment. During nine consecutive runs, no significant loss of activity is found with an overall TON of 8700 in regard to the rhodium catalyst and an average rhodium leaching of only of 0.07% per run is observed.

Synthesis of novel rhodium phosphite catalysts for efficient and selective isomerization-hydroformylation reactions

Piras, Irene,Jennerjahn, Reiko,Jackstell, Ralf,Baumann, Wolfgang,Spannenberg, Anke,Franke, Robert,Wiese, Klaus-Diether,Beller, Matthias

, p. 479 - 486 (2010)

New modular H8-BINOL-based phosphite ligands have been synthesized. High activity and regioselectivity has been achieved in the rhodium-catalyzed isomerization-hydroformylation of internal olefins. The active catalysts have been characterized by in situ NMR studies.

n-pentane carbonylation with CO on sulfated zirconia: An in situ solid-state 13C NMR study

Luzgin,Stepanov,Shmachkova,Kotsarenko

, p. 23 - 25 (2001)

Using 13C CP/MAS NMR, the first evidence has been obtained for n-pentane carbonylation with carbon monoxide into C6 aldehydes, ketones and carboxylic acids on a sulfated zirconia catalyst.

Synthesis of Chiral Amines via a Bi-Enzymatic Cascade Using an Ene-Reductase and Amine Dehydrogenase

Fossey-Jouenne, Aurélie,Jongkind, Ewald P. J.,Mayol, Ombeline,Paul, Caroline E.,Vergne-Vaxelaire, Carine,Zaparucha, Anne

, (2021/12/23)

Access to chiral amines with more than one stereocentre remains challenging, although an increasing number of methods are emerging. Here we developed a proof-of-concept bi-enzymatic cascade, consisting of an ene reductase and amine dehydrogenase (AmDH), to afford chiral diastereomerically enriched amines in one pot. The asymmetric reduction of unsaturated ketones and aldehydes by ene reductases from the Old Yellow Enzyme family (OYE) was adapted to reaction conditions for the reductive amination by amine dehydrogenases. By studying the substrate profiles of both reported biocatalysts, thirteen unsaturated carbonyl substrates were assayed against the best duo OYE/AmDH. Low (5 %) to high (97 %) conversion rates were obtained with enantiomeric and diastereomeric excess of up to 99 %. We expect our established bi-enzymatic cascade to allow access to chiral amines with both high enantiomeric and diastereomeric excess from varying alkene substrates depending on the combination of enzymes.

Heterogeneous catalytic condensation of propanal

Afaunov, A. A.,Bruk, L. G.,Flid, V. R.,Martsinkevich, E. M.

, p. 2031 - 2033 (2021/11/04)

The aldol homocondensation of propanal was studied in the presence of a heterogeneous titanium oxide catalyst modified with amino acid (AA) l-norleucine. The effects of the temperature and l-norleucine content on the conversion of propanal and selectivity of the process were studied. The reaction products were identified, and possible mechanisms are considered. A new catalyst (5% AA on titanium dioxide) was developed for the synthesis of 2-methyl-2-pentenal with the selectivity >90%.

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