7492-38-8

Basic information

• Product Name: 2-METHYL-4-OCTANONE
• Synonyms: 2-METHYL-4-OCTANONE;n-Butyl isobutyl ketone;2-Methyl-4-octanone,99%;2-Ethyl-4-octanone;2-Methyloctan-4-one
• CAS NO: 7492-38-8
• Molecular Formula: C₉H₁₈O
• Molecular Weight: 142.24
• Mol File: 7492-38-8.mol
• Article Data: 4

Chemical Properties

• Melting Point: -18.52°C (estimate)
• Boiling Point: 180℃
• Flash Point: 57.565 °C
• Appearance: /
• Density: 0.8258 (estimate)
• Vapor Pressure: 0.913mmHg at 25°C
• Refractive Index: 1.4150
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 2-METHYL-4-OCTANONE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-METHYL-4-OCTANONE(7492-38-8)
• EPA Substance Registry System: 2-METHYL-4-OCTANONE(7492-38-8)

Safety Data

• Statements: 52
• Hazardous Substances Data: 7492-38-8(Hazardous Substances Data)

Usage

Chemical Properties

Colorless clear liquid

Uses

2-Methyl-4-octanone is a building block ketone for proteomics research. It is also used as pharmaceutical intermediates.

InChI:InChI=1/C9H18O/c1-4-5-6-9(10)7-8(2)3/h8H,4-7H2,1-3H3

Synthetic route

2-methyloctan-4-ol (40575-41-5) → 2-methyloctan-4-one (7492-38-8)

Conditions	Yield
With jones' reagent Oxidation;	86%
With chromium(VI) oxide; acetic acid

2-methyloctan-4-ol (40575-41-5) → 2-methyloctan-4-one (7492-38-8)

Conditions	Yield
With jones' reagent Oxidation;	86%
With chromium(VI) oxide; acetic acid

oxalyl dichloride (79-37-8) + 2-methyloctan-4-ol (40575-41-5) + dimethyl sulfoxide (67-68-5) → 2-methyloctan-4-one (7492-38-8)

Conditions	Yield
With triethylamine In water; 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran	79%

tributyl borane (122-56-5) + isopentanoyl chloride (108-12-3) → 2-methyloctan-4-one (7492-38-8)

Conditions	Yield
With potassium acetate; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran at 65℃; for 3h; Substitution;	56%

2-methyl-oct-5-en-4-one (17577-93-4) → 2-methyloctan-4-one (7492-38-8)

Conditions	Yield
With nickel Hydrogenation;

di-n-butylcadmium (3431-67-2) + isopentanoyl chloride (108-12-3) → 2-methyloctan-4-one (7492-38-8)

Conditions	Yield
With benzene

di-n-butylcadmium (3431-67-2) + isopentanoyl chloride (108-12-3) → 2-methyloctan-4-one (7492-38-8)

Conditions	Yield
With benzene

pentanal (110-62-3) + isobutylmagnesium bromide (926-62-5) → 2-methyloctan-4-one (7492-38-8)

Conditions	Yield
(i) ether, (ii) Na2Cr2O7, H2SO4; Multistep reaction;

pentanal (110-62-3) + isobutylmagnesium bromide (926-62-5) → 2-methyloctan-4-one (7492-38-8)

Conditions	Yield
(i) ether, (ii) Na2Cr2O7, H2SO4; Multistep reaction;

2-methyl-3-octyne (55402-15-8) → 2-methyloctan-4-one (7492-38-8)

Conditions	Yield
(i) bis-(2,3-dimethyl-propyl)-borane, THF, (ii) aq. H2O2, aq. NaOH; Multistep reaction;

2-methyl-3-octyne (55402-15-8) → 2-methyloctan-4-one (7492-38-8)

Conditions	Yield
(i) bis-(2,3-dimethyl-propyl)-borane, THF, (ii) aq. H2O2, aq. NaOH; Multistep reaction;

4-methyl-pent-3-en-2-one (141-79-7) + propionaldehyde (123-38-6) → 2-methyloctan-4-one (7492-38-8)

Conditions	Yield
(i) MgO, (heating), (ii) H2, Raney-Ni, EtOH; Multistep reaction;

1-(trans-2-methyl-cyclopropyl)-pentan-1-one → 2-methyloctan-4-one (7492-38-8)

Conditions	Yield
(i) Li, liq. NH3, (ii) aq. Na2Cr2O7, aq. H2SO4; Multistep reaction;

1-(trans-2-methyl-cyclopropyl)-pentan-1-one → 2-methyloctan-4-one (7492-38-8)

Conditions	Yield
(i) Li, liq. NH3, (ii) aq. Na2Cr2O7, aq. H2SO4; Multistep reaction;

4-methyl-pent-3-en-2-one (141-79-7) + acrolein (107-02-8) → 2-methyloctan-4-one (7492-38-8)

Conditions	Yield
(i) MgO, (heating), (ii) TsOH, (iii) H2, Raney-Ni, EtOH; Multistep reaction;

(1-Benzenesulfinyl-1-isobutyl-pentyl)-trimethyl-silane → 2-methyloctan-4-one (7492-38-8)

Conditions	Yield
With mercury(II) diacetate 1.) THF, reflux, 4 h, 2.) THF, water, 17 h, room temperature; Yield given. Multistep reaction;

(1-Benzenesulfinyl-1-isobutyl-pentyl)-trimethyl-silane → 2-methyloctan-4-one (7492-38-8)

Conditions	Yield
With mercury(II) diacetate 1.) THF, reflux, 4 h, 2.) THF, water, 17 h, room temperature; Yield given. Multistep reaction;

isovaleraldehyde (590-86-3) + hydro chloride of 1-<α-amino-isopentyl>-naphthol-(2) → 2-methyloctan-4-one (7492-38-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: 87 percent / diethyl ether / 20 °C 2: 86 percent / Jones' reagent View Scheme

(1-Isobutyl-1-phenylsulfanyl-pentyl)-trimethyl-silane (105494-91-5) → 2-methyloctan-4-one (7492-38-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: 85percent m-chloroperbenzoic acid / CH2Cl2 / 1.5 h / -23 °C 2: 2.) 1 M mercury(II) acetate / 1.) THF, reflux, 4 h, 2.) THF, water, 17 h, room temperature View Scheme

(1-Isobutyl-1-phenylsulfanyl-pentyl)-trimethyl-silane (105494-91-5) → 2-methyloctan-4-one (7492-38-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: 85percent m-chloroperbenzoic acid / CH2Cl2 / 1.5 h / -23 °C 2: 2.) 1 M mercury(II) acetate / 1.) THF, reflux, 4 h, 2.) THF, water, 17 h, room temperature View Scheme

(E)-2-octen-4-one (22286-99-3) → 2-methyloctan-4-one (7492-38-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: (i) NaH, DMSO, (ii) /BRN= 1700900/ 2: (i) Li, liq. NH3, (ii) aq. Na2Cr2O7, aq. H2SO4 View Scheme

(E)-2-octen-4-one (22286-99-3) → 2-methyloctan-4-one (7492-38-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: (i) NaH, DMSO, (ii) /BRN= 1700900/ 2: (i) Li, liq. NH3, (ii) aq. Na2Cr2O7, aq. H2SO4 View Scheme

(C4H9)3SnOCH(C4H9)C3H4CH3 → diisobutyl ketone (108-83-8) + 2-methyloctan-4-one (7492-38-8) + tributyltin butoxide (3882-70-0) + Isobutyl-(2-methylcyclopropyl)-keton

Conditions	Yield
With t-C4H9OOC4H9-t at 130-140°C; proportion of c-C3H4(CH3)COCH3, i-C4H9COC4H9-i, n-C4H9COC4H9-i = 86:4:10;
With t-C4H9OOC4H9-t at 130-140°C; proportion of c-C3H4(CH3)COCH3, i-C4H9COC4H9-i, n-C4H9COC4H9-i = 86:4:10;

(C4H9)3SnOCH(C4H9)C3H4CH3 → diisobutyl ketone (108-83-8) + 2-methyloctan-4-one (7492-38-8) + tributyltin butoxide (3882-70-0) + Isobutyl-(2-methylcyclopropyl)-keton

Conditions	Yield
With t-C4H9OOC4H9-t at 130-140°C; proportion of c-C3H4(CH3)COCH3, i-C4H9COC4H9-i, n-C4H9COC4H9-i = 86:4:10;
With t-C4H9OOC4H9-t at 130-140°C; proportion of c-C3H4(CH3)COCH3, i-C4H9COC4H9-i, n-C4H9COC4H9-i = 86:4:10;

2-methyloctan-4-one (7492-38-8) → C9H17IO

Conditions	Yield
With sulfuric acid; iodine; silica gel; sodium nitrite In acetonitrile at 22℃; for 2h;	85%

2-methyloctan-4-one (7492-38-8) → C9H17IO

Conditions	Yield
With sulfuric acid; iodine; silica gel; sodium nitrite In acetonitrile at 22℃; for 2h;	85%

2-methyloctan-4-one (7492-38-8) → (R)-(-)-2-methyl-4-octanol + (4S)-2-methyloctan-4-ol

Conditions	Yield
With methanesulfonic acid; (R,R)-dihydroborate In hexane at 0℃; for 24h; Title compound not separated from byproducts;	A 72% B n/a

2-methyloctan-4-one (7492-38-8) → (R)-(-)-2-methyl-4-octanol + (4S)-2-methyloctan-4-ol

Conditions	Yield
With methanesulfonic acid; (R,R)-dihydroborate In hexane at 0℃; for 24h; Title compound not separated from byproducts;	A 72% B n/a

Å molecular sieves + 2-methyloctan-4-one (7492-38-8) + benzylamine (100-46-9) → N-benzyl-2-methyl-4-aminooctane (142121-46-8)

Conditions	Yield
With sodium cyanoborohydride; triethylamine In methanol; hexane; ethyl acetate	46%

Å molecular sieves + 2-methyloctan-4-one (7492-38-8) + benzylamine (100-46-9) → N-benzyl-2-methyl-4-aminooctane (142121-46-8)

Conditions	Yield
With sodium cyanoborohydride; triethylamine In methanol; hexane; ethyl acetate	46%

Å molecular sieves + 2-methyloctan-4-one (7492-38-8) → 2-methyl-4-aminooctane (33788-04-4)

Conditions	Yield
With ammonium acetate; sodium cyanoborohydride In methanol; chloroform	25%

Å molecular sieves + 2-methyloctan-4-one (7492-38-8) → 2-methyl-4-aminooctane (33788-04-4)

Conditions	Yield
With ammonium acetate; sodium cyanoborohydride In methanol; chloroform	25%

2-methyloctan-4-one (7492-38-8) → 2-methyloctan-4-ol (40575-41-5)

Conditions	Yield
With lithium aluminium tetrahydride; diethyl ether
With nickel Hydrogenation;

2-methyloctan-4-one (7492-38-8) + indole-2,3-dione (91-56-5) → 2-isobutyl-3-propyl-quinoline-4-carboxylic acid

Conditions	Yield
With potassium hydroxide

2-methyloctan-4-one (7492-38-8) + indole-2,3-dione (91-56-5) → 2-isobutyl-3-propyl-quinoline-4-carboxylic acid

Conditions	Yield
With potassium hydroxide

2-methyloctan-4-one (7492-38-8) → [2-(1-isobutyl-pentyloxy)-ethyl]-dimethyl-amine

Conditions	Yield
Multi-step reaction with 2 steps 1: lithium alanate; diethyl ether 2: sodium amide; benzene / 100 °C View Scheme

2-methyloctan-4-one (7492-38-8) + 2-(aminooxy)-2-methylpropanoic acid hydrochloride → (E)-2-methyl-2-(((2-methyloctan-4-ylidene)amino)oxy)propanoic acid + (Z)-2-methyl-2-(((2-methyloctan-4-ylidene)amino)oxy)propanoic acid

Conditions	Yield
With pyridine at 100℃; for 2h;	A n/a B n/a

2-methyloctan-4-one (7492-38-8) + 2-(aminooxy)-2-methylpropanoic acid hydrochloride → (E)-2-methyl-2-(((2-methyloctan-4-ylidene)amino)oxy)propanoic acid + (Z)-2-methyl-2-(((2-methyloctan-4-ylidene)amino)oxy)propanoic acid

Conditions	Yield
With pyridine at 100℃; for 2h;	A n/a B n/a

Upstream product

• 40575-41-5 2-methyloctan-4-ol 
• 17577-93-4 2-methyl-oct-5-en-4-one 
• 3431-67-2 di-n-butylcadmium 
• 108-12-3 isopentanoyl chloride 
• 110-62-3 pentanal 
• 926-62-5 isobutylmagnesium bromide 
• 55402-15-8 2-methyl-3-octyne 
• 141-79-7 4-methyl-pent-3-en-2-one 
• 123-38-6 propionaldehyde 
• 107-02-8 acrolein 
• 122-56-5 tributyl borane 
• 590-86-3 isovaleraldehyde 
• 105494-91-5 (1-Isobutyl-1-phenylsulfanyl-pentyl)-trimethyl-silane 
• 22286-99-3 (E)-2-octen-4-one 

Downstream Products

• 40575-41-5 2-methyloctan-4-ol 
• 142121-46-8 N-benzyl-2-methyl-4-aminooctane 

Relevant articles and documents

Preparation of ketones via the palladium-catalyzed cross-coupling of acid chlorides with trialkylboranes

Trialkylboranes react with acid chlorides in the presence of palladium to generate alkyl and aryl ketones in good yields. (C) 2000 Elsevier Science Ltd.

Certain sulfonamide heterobicyclic platelet activating factor antagonists

Compounds of general formula I; STR1 wherein: A1 is =N--, =CH-- or =CR1 --; A2 is =N--, =CH-- or =CR2 --; provided that, when one of A1 and A2 is a nitrogen atom, the other of A1 and A2 is other than a nitrogen atom; wherein the other variables are as defined in the specification and their pharmaceutically and veterinarily acceptable acid addition salts and hydrates are antagonists of platelet activating factor (PAF) and as such are useful in the treatment or amelioration of various diseases or disorders mediated by PAF.