88-09-5

Basic information

• Product Name: 2-Ethylbutyric acid
• Synonyms: (C2H5)2CHCOOH;2-ethyl-butanoicaci;2-Ethylbutansαure;2-Ethylbuttersαure;2-ethylbutyric;2-ethyl-butyricaci;2-Ethylbutyricaicd;3-Pentanecarboxylic acid
• CAS NO: 88-09-5
• Molecular Formula: C₆H₁₂O₂
• Molecular Weight: 116.16
• EINECS: 201-796-4
• Mol File: 88-09-5.mol
• Article Data: 45

Chemical Properties

• Melting Point: -14 °C
• Boiling Point: 99-101 °C18 mm Hg(lit.)
• Flash Point: 190 °F
• Appearance: clear liquid
• Density: 0.92 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.08 mm Hg ( 20 °C)
• Refractive Index: n20/D 1.413(lit.)
• Storage Temp.: Store below +30°C.
• Solubility: 18g/l
• PKA: pKa: 4.751(25°C)
• Explosive Limit: 1.4%(V)
• Water Solubility: 18 g/L (20 ºC)
• Merck: 14,3110
• BRN: 1098634
• CAS DataBase Reference: 2-Ethylbutyric acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Ethylbutyric acid(88-09-5)
• EPA Substance Registry System: 2-Ethylbutyric acid(88-09-5)

Safety Data

• Hazard Codes: C,Xn
• Statements: 21-36/37/38-34
• Safety Statements: 26-36/37/39-45-36
• RIDADR: UN 2810 6.1/PG 3
• WGK Germany: 1
• RTECS: ET1400000
• TSCA: Yes
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 88-09-5(Hazardous Substances Data)

Usage

Chemical Properties

Different sources of media describe the Chemical Properties of 88-09-5 differently. You can refer to the following data:
1. clear colorless to light yellow liquid
2. 2-Ethylbutyric acid has a rancid, oily-fruity, acidulous odor

Occurrence

Reported found in guava fruit, wheaten bread and cheeses (Parmesan, blue, cheddar, provolone, Romano and goat), apple, banana, grape, melon, papaya, peach, pineapple and more.

Uses

Different sources of media describe the Uses of 88-09-5 differently. You can refer to the following data:
1. 2-Ethylbutyric acid is used as the internal standard for determining volatile fatty acids (VFAs) in wastewater from the constructed wetlands. It is used in the determination of both free and fatty acids in milk and milk products by HPLC method with direct derivatisation.
2. 2-Ethylbutyric Acid is a flavoring agent that is a clear liquid, color- less, with a rancid odor. it is miscible in alcohol and ether, sparingly soluble in water, and is obtained by chemical synthesis.
3. Ester formation; intermediate for drugs, dyestuffs, chemicals; flavoring.

Preparation

By catalytic oxidation of diethylacetaldehyde or by decarboxylation of diethylmalonic acid.

Aroma threshold values

Detection: 15 to 600 ppb

Taste threshold values

Taste characteristics at 35 ppm: acidic, fruity, tropical with a creamy aftertaste.

Safety Profile

Moderately toxic by ingestion and skin contact. An irritant to skin and mucous membranes. A severe eye irritant. See also ESTERS. Narcotic in high concentrations. Flammable liquid. To fight fire, use CO2, dry chemical, alcohol foam. When heated to decomposition it emits acrid smoke and fumes.

InChI:InChI=1/C6H12O2/c1-3-5(4-2)6(7)8/h5H,3-4H2,1-2H3,(H,7,8)/p-1

Synthetic route

diethyl malonic acid (510-20-3) → 2-Ethylbutanoic acid (88-09-5)

Conditions	Yield
With poly-4-vinylpyridine In N,N-dimethyl-formamide for 0.05h; microwave irradiation;	93%
In water for 0.25h; Decarboxylation; microwave irradiation;	80%
at 170 - 180℃;

(2-ethyl-1-butyl)boronic acid (140614-19-3) → 2-Ethylbutanoic acid (88-09-5)

Conditions	Yield
With chromium(VI) oxide In dichloromethane; acetic acid at 25℃; for 12h;	92%

2-Ethylbutyraldehyde (97-96-1) → 2-Ethylbutanoic acid (88-09-5)

Conditions	Yield
With N-hydroxyphthalimide; oxygen In acetonitrile at 30℃; for 3h; Schlenk technique;	88%
With N-hydroxyphthalimide; oxygen In acetonitrile at 30℃; under 760.051 Torr; for 3h; Catalytic behavior; Solvent; Schlenk technique;	88%
With calcium hypochlorite; acetic acid In water; acetonitrile Ambient temperature;	75%

2-ethyl-1-butanol (97-95-0) → 2-Ethylbutanoic acid (88-09-5)

Conditions	Yield
at 70℃; for 3.5h; electrolysis: nickel net anode, cylindrical stainless steel cathode; electrolyte: 1M NaOH/H2O;	73%
at 70℃; for 3.5h; Product distribution; electrolysis: nickel net anode, cylindrical stainless steel cathode; electrolyte: 1M NaOH/water; variation of temperature;	73%
Stage #1: 2-ethyl-1-butanol With [RuCl2(p-cymene)(iPr2-imy)]; tricyclohexylphosphine tetrafluoroborate; potassium hydroxide In toluene for 18h; Schlenk technique; Inert atmosphere; Reflux; Stage #2: With hydrogenchloride In water pH=1;	60%
With dichloro(1,5-cyclooctadiene)ruthenium(II); C30H30N3P2(1+)*Cl(1-); potassium hydroxide In toluene at 120℃; for 24h; Inert atmosphere; Schlenk technique;	55%
With permanganate(VII) ion

3,3-diethyl-2-phenylsulphonyl-2-trimethylsilyloxirane (128608-23-1) → 2-Ethylbutanoic acid (88-09-5) + 2-bromo-2-ethylbutanoyltrimethylsilane (128589-01-5) + (E)-2-ethylbut-2-enoyltrimethylsilane (128589-05-9, 139117-12-7) + 2-ethyl-2-phenylsulphonylbutanoyltrimethylsilane (139117-13-8)

Conditions	Yield
With magnesium bromide ethyl etherate In diethyl ether at 0℃; for 2h;	A 19% B 57% C 9% D 0.5%

3-Dibutoxymethyl-pentane (104723-47-9) → 2-Ethylbutanoic acid (88-09-5) + butyl 2-ethylbutyrate (5129-48-6) + butyric acid (107-92-6) + butan-1-ol (71-36-3)

Conditions	Yield
With oxygen; cobalt(II) acetate at 90℃; under 750.06 Torr; Mechanism; Rate constant; other pressure;	A 2% B 6% C 10% D 46%

ethyl 2,2-diethyl-3-oxobutanoate (1619-57-4) → 2-Ethylbutanoic acid (88-09-5) + 3-ethyl-2-pentanone (6137-03-7)

Conditions	Yield
With barium dihydroxide In water for 18h; Heating;	A 10% B 38%

carbon monoxide (201230-82-2) + pentane (109-66-0) → 2-Ethylbutanoic acid (88-09-5) + 2-Methylpentanoic acid (97-61-0, 22160-39-0)

Conditions	Yield
With potassium peroxodisulfate; Cu(1,10-phenanthroline)(1,2-ethanediphosphonic acid); water In acetonitrile at 60℃; under 15201 Torr; for 4h; Autoclave; High pressure; Overall yield = 35.8 %Chromat.;	A 10.6% B 24%
With dipotassium peroxodisulfate; BF4(1-)*C24H51BCu3N3O16(1+)*2H2O; water In acetonitrile at 60℃; under 15201 Torr; for 6h; Autoclave;	A 8.6% B 17%
With dipotassium peroxodisulfate; C26H38Cu3N4O16; water In acetonitrile at 60℃; for 6h; Reagent/catalyst; Autoclave; Green chemistry;	A 7.4% B 17.2%

peracetic acid (79-21-0) + hex-3-yne (928-49-4) → 2-Ethylbutanoic acid (88-09-5) + propionic acid (802294-64-0)

diethyl ether (60-29-7) + allyl 2-ethylbutyrate (7493-69-8) + phenylmagnesium bromide → allylbenzene (300-57-2) + 2-Ethylbutanoic acid (88-09-5) + 2-ethyl-1,1-diphenylbutanol (126328-30-1)

3-pentyl iodide (1809-05-8) + potassium cyanide (151-50-8) → 2-Ethylbutanoic acid (88-09-5)

Conditions	Yield
With ethanol man verseift das erhaltene Nitril durch Kochen mit waessr.-alkoholischer Kalilauge;

hex-3-yne (928-49-4) → 2-Ethylbutanoic acid (88-09-5)

Conditions	Yield
With peracetic acid; acetic acid

4-ethylhexanoic acid (6299-66-7) → 2-Ethylbutanoic acid (88-09-5)

Conditions	Yield
With potassium hydroxide; potassium acetate at 370℃; unter Zutritt von Luft;

2-ethyl-3-bromo-butyric acid (861310-83-0) → 2-Ethylbutanoic acid (88-09-5)

Conditions	Yield
With sodium amalgam; water man haelt die Loesung durch Zugabe von verduennter Schwefelsaeure bei ganz schwach alkalischer Reaktion;

2,2-diethyl-3-hydroxy-butyric acid → 2-Ethylbutanoic acid (88-09-5) + acetaldehyde (75-07-0)

Conditions	Yield
Destillation;

2-ethyl-2-cyano-butyric acid (4386-07-6) → 2-Ethylbutanoic acid (88-09-5)

Conditions	Yield
With hydrogenchloride at 160℃;

2,2-diethyl-acetoacetic acid methyl ester (85153-63-5) → 2-Ethylbutanoic acid (88-09-5) + 3-ethyl-2-pentanone (6137-03-7)

Conditions	Yield
With sodium hydroxide

diethyl malonic acid (510-20-3) → 2-Ethylbutanoic acid (88-09-5) + methylammonium carbonate (15719-64-9, 15719-76-3, 97762-63-5)

Conditions	Yield
at 170 - 180℃;

diethylketene dimer (3898-61-1) + furan-2,3,5(4H)-trione pyridine (1:1) → 2-Ethylbutanoic acid (88-09-5) + 3,5-diethylheptan-4-one (75072-46-7)

Conditions	Yield
at 150℃;

ethyl acetate (141-78-6) → 2-Ethylbutanoic acid (88-09-5) + ethyl 2-ethylbutanoate (2983-38-2)

Conditions	Yield
With sodium Man erhitzt den erhaltenen Natriumacetessigester mit Aethyljodid auf 100grad , destilliert das Reaktionsprodukt, behandelt den 151grad siedende Aethylester mit siedendem Barytwasser, diesen verseift man durch alkoh.Kalilauge;
With sodium Erhitzen des Reaktionsprodukts mit Aethyljodid auf 100grad, Destillieren;

ethene (74-85-1) + potassium acetate (127-08-2) → 2-Ethylbutanoic acid (88-09-5)

Conditions	Yield
With sodium amide In n-heptane at 240 - 250℃;

pentan-1-ol (71-41-0) + carbon monoxide (201230-82-2) → 2-Ethylbutanoic acid (88-09-5)

Conditions	Yield
With phosphoric acid

ethyl 2-ethyl-2-cyanobutyrate (1619-56-3) → 2-Ethylbutanoic acid (88-09-5) + ethyl 2-ethylbutanoate (2983-38-2)

Conditions	Yield
With potassium In N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether at 0℃;

2-ethyl-1-butene (760-21-4) → 2-Ethylbutanoic acid (88-09-5)

Conditions	Yield
Yield given. Multistep reaction;

hexane (110-54-3) + carbon monoxide (201230-82-2) → 2-Ethylbutanoic acid (88-09-5) + 2-Methylpentanoic acid (97-61-0, 22160-39-0) + hexanoic acid (142-62-1)

Conditions	Yield
With dipotassium peroxodisulfate; palladium diacetate In methanol; trifluoroacetic acid at 80℃; under 22800 Torr; for 20h; Yield given. Yields of byproduct given;

1-penten (109-67-1) + carbon monoxide (201230-82-2) → 2-Ethylbutanoic acid (88-09-5) + 2,2-dimethylbutyric acid (595-37-9) + Trimethylacetic acid (75-98-9)

Conditions	Yield
With sulfuric acid; silver(l) oxide at 30℃; under 760 Torr; for 4h; Product distribution;	A 9 % Turnov. B 74 % Turnov. C 7 % Turnov.

carbon monoxide (201230-82-2) + 2-pentene (109-68-2) → 2-Ethylbutanoic acid (88-09-5) + 2-Methylpentanoic acid (97-61-0, 22160-39-0) + hexanoic acid (142-62-1)

Conditions	Yield
With water; bis-triphenylphosphine-palladium(II) chloride; triphenylphosphine In 1,4-dioxane at 95℃; under 15200 Torr; for 4h; Product distribution; Rate constant; other catalyst, time;

diethylketene (24264-08-2) → 2-Ethylbutanoic acid (88-09-5)

Conditions	Yield
With water In acetonitrile at 20℃; Rate constant; var. H2O conc.;

2-methyl-3-furancarboxylic acid (6947-94-0) + acetic acid (64-19-7) + colloidal platinum → 2-Ethylbutanoic acid (88-09-5)

Conditions	Yield
Hydrogenation;

diethylbarbituric acid (57-44-3) + potassium hydroxide → 2-Ethylbutanoic acid (88-09-5) + ammonia (7664-41-7) + methylammonium carbonate (15719-64-9, 15719-76-3, 97762-63-5)

2-Ethylbutanoic acid (88-09-5) + zinc(II) oxide → tetrazinc μ4-oxohexa-mu.-2-ethylbutanoate

Conditions	Yield
In toluene mixt. 2-ethylbutanoic acid (6 equiv.) and zinc oxide (4 equiv.) and toluene heated with stirring for 3 h (water removed); product filtered, solvent removed from filtrate; elem. anal.;	99%

2-Ethylbutanoic acid (88-09-5) → 2-ethylbutyric anhydride (54502-37-3)

Conditions	Yield
With triethylamine; chlorophosphoric acid diphenyl ester In dichloromethane at 20℃; for 0.25h;	98.2%
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20 - 25℃;	78%
With sulfuric acid; acetic anhydride

2-Ethylbutanoic acid (88-09-5) + benzyl alcohol (100-51-6) → benzyl 2-ethylbutanoate

Conditions	Yield
tetrachlorobis(tetrahydrofuran)hafnium(IV) In toluene for 60h; Heating;	98%
With molecualar sevies 4A; tetrachlorobis(tetrahydrofuran)hafnium(IV) In toluene at 120℃; for 60h;	98%

2-Ethylbutanoic acid (88-09-5) + octanol (111-87-5) → octyl 2-ethylbutanoate

Conditions	Yield
With tetra-N-butylammonium tribromide for 3h; Inert atmosphere; Reflux;	98%
With dimesitylammonium pentafluorobenzenesulfonate In n-heptane at 80℃; for 24h;	94%
With N-butyl-2,4-dinitroanilinium p-toluenesulfonate In 2,2,4-trimethylpentane for 22h; Reflux;	54%
With 2-oleamido-5-nitro-pyridinium p-toluenesulfonate In 2,2,4-trimethylpentane for 48h; Reflux;	50%

2-Ethylbutanoic acid (88-09-5) + (3aRS,4RS,6aSR)-2-(3-(trifluoromethyl)benzyl)octahydrocyclopenta[c]pyrrol-4-amine → 2-ethyl-N-{(3aRS,4RS,6aSR)-2-[3-(trifluoromethyl)benzyl]octahydrocyclopenta[c]pyrrol-4-yl}butanamide

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 20h; Inert atmosphere;	98%

2-Ethylbutanoic acid (88-09-5) + N,O-dimethylhydroxylamine*hydrochloride (6638-79-5) → 2-ethyl-N-methoxy-N-methylbutanamide

Conditions	Yield
Stage #1: 2-Ethylbutanoic acid With N,N'-carbonyl diimidazole In tetrahydrofuran at 20℃; for 0.5h; Stage #2: N,O-dimethylhydroxylamine*hydrochloride With triethylamine In tetrahydrofuran at 20℃; for 6h; Reflux;	98%
With 1,1'-carbonyldiimidazole In dichloromethane at 0 - 20℃;

methanol (67-56-1) + 2-Ethylbutanoic acid (88-09-5) → 2-ethyl-butyric acid methyl ester (816-11-5)

Conditions	Yield
With sulfuric acid	95%
With sulfuric acid for 10h;	10%
With sulfuric acid
With thionyl chloride at 80℃;
With thionyl chloride at 80℃;

2-Ethylbutanoic acid (88-09-5) + benzylamine (100-46-9) → N-benzyl-2-ethylbutanamide

Conditions	Yield
With 4,5,6,7-tetrachlorobenzo[d][1,3,2]dioxaborole In toluene for 24h; Heating;	93%
With ammonium chloride

2-Ethylbutanoic acid (88-09-5) + C14H26O7 (1313484-36-4) → C20H36O8

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 19h; Inert atmosphere;	93%

2-Ethylbutanoic acid (88-09-5) + 2',3',5'-tri-O-acetylnebularine (15981-63-2) → (2R,3R,4R,5R)-2-(acetoxymethyl)-5-(6-(pentan-3-yl)-9H-purin-9-yl)tetrahydrofuran-3,4-diyl diacetate (1512860-57-9)

Conditions	Yield
With ammonium peroxydisulfate; silver nitrate In dichloromethane; water at 20℃; for 6h; Minisci Aromatic Substitution; regioselective reaction;	92%

2-Ethylbutanoic acid (88-09-5) + (S)-dibenzyl 2-(2-(2-(benzyloxy)-2-oxoethoxy)-4-(5-((((R)-2-((R)-1-(N-hydroxyformamido)propyl)heptanamido)methyl)carbamoyl)furan-2-yl)benzamido)succinate → (S)-dibenzyl 2-(2-(2-(benzyloxy)-2-oxoethoxy)-4-(5-((((R)-2-((R)-1-(N-((2-ethylbutanoyl)oxy)formamido)propyl)heptanamido)methyl)carbamoyl)furan-2-yl)benzamido)succinate

Conditions	Yield
With 4-methyl-morpholine; HATU for 1h;	92%

2-Ethylbutanoic acid (88-09-5) + 1,3-dihydro-1-(1-methylethenyl)-2H-benzimidazol-2-one (52099-72-6) → 1-(2-ethylbutanoyl)-3-(prop-1-en-2-yl)-1H-benzo[d]imidazol-2(3H)-one (1207377-19-2)

Conditions	Yield
Stage #1: 2-Ethylbutanoic acid; 1,3-dihydro-1-(1-methylethenyl)-2H-benzimidazol-2-one With triethylamine In dichloromethane for 0.0833333h; Inert atmosphere; Cooling with ice; Stage #2: With bis(trichloromethyl) carbonate In dichloromethane at 20℃; Inert atmosphere;	91%

2-Ethylbutanoic acid (88-09-5) + benzo[e][1,2,3]oxathiazine 2,2-dioxide (71730-46-6) → 4-(pentan-3-yl)benzo[e][1,2,3]oxathiazine 2,2-dioxide

Conditions	Yield
With dipotassium peroxodisulfate; silver nitrate In water; acetonitrile at 60℃; for 48h;	91%

2-Ethylbutanoic acid (88-09-5) + 2-methyl-1-(2-phenyl-1H-benzo[d]imidazol-1-yl)prop-2-en-1-one → C21H22N2O

Conditions	Yield
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In ethanol at 20 - 25℃; for 24h; Irradiation;	90%

2-Ethylbutanoic acid (88-09-5) + o-chlorocinnamic acid (3752-25-8) → C13H17Cl

Conditions	Yield
With dipotassium peroxodisulfate; copper; silver nitrate In water; acetonitrile at 90℃; for 12h;	89%

2-Ethylbutanoic acid (88-09-5) → 2-ethyl-butyryl fluoride (654-43-3)

Conditions	Yield
With diethylamino-sulfur trifluoride In dichloromethane at 0℃; for 0.25h; Fluorination;	88%

2-Ethylbutanoic acid (88-09-5) + C6H4NCH2CHCCH2 (491-35-0) → 4-methyl-2-(pentan-3-yl)quinoline

Conditions	Yield
With bis-[(trifluoroacetoxy)iodo]benzene In acetonitrile at 20℃; for 12h; Inert atmosphere; Irradiation; Schlenk technique;	88%

2-Ethylbutanoic acid (88-09-5) + 5-chloro-2-isocyano-1,1’-biphenyl (1428264-92-9) → 2-chloro-6-(pentan-3-yl)phenanthridine

Conditions	Yield
With potassium phosphate; dipotassium peroxodisulfate; silver carbonate In water; acetonitrile at 70℃; for 3h; Inert atmosphere;	87%

2-Ethylbutanoic acid (88-09-5) + dodecacarbonyl-triangulo-triruthenium (15243-33-1) → {Ru2(O2CCH(C2H5)CH2CH3)2(CO)4(P(C6H5)3)2} (125665-82-9)

Conditions	Yield
With triphenylphosphine In tetrahydrofuran under N2; Ru-compd. and excess of acid heated at reflux for 4h, addn. of PPh3, mixt. heated for a further 20 min; recrystd. (CH2Cl2/EtOH, open conditions); elem. anal.;	86%

2-Ethylbutanoic acid (88-09-5) + 1-(3,4-diamino-5-(3-fluorophenyl)pyridin-2-yl)piperidine-3-carboxamide (1600524-53-5) → 1-(7-(3-fluorophenyl)-2-(pentan-3-yl)-1H-imidazo[4,5-c]pyridin-4-yl)piperidine-3-carbonitrile

Conditions	Yield
With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide at 180℃; for 0.2h; Inert atmosphere; Sealed tube; Microwave irradiation;	86%

2-Ethylbutanoic acid (88-09-5) → chlorure d'acide ethyl-2 butyrique (2736-40-5)

Conditions	Yield
With thionyl chloride	85%
With phosphorus trichloride
With thionyl chloride

2-Ethylbutanoic acid (88-09-5) + testosterone (58-22-0) → testosterone-17β-2'-ethylbutanoate (69510-14-1)

Conditions	Yield
With benzenesulfonyl chloride	85%
With pyridine; benzenesulfonyl chloride Ambient temperature;	72%

1,3-Benzothiazole (95-16-9) + 2-Ethylbutanoic acid (88-09-5) → 2-(pentan-3-yl)benzo[d]thiazole (93194-82-2)

Conditions	Yield
With dipotassium peroxodisulfate; silver nitrate In dichloromethane; water at 20℃; for 8h;	85%
With ammonium peroxydisulfate; anthocyanin In dichloromethane; water at 20℃; Minisci Aromatic Substitution; Irradiation; Green chemistry;	59%

2-Ethylbutanoic acid (88-09-5) → 2-ethyl-N-butylamine (617-79-8) + bis(2-ethylbutyl)amine (54774-85-5) + 2-ethylbutanamide (1114-38-1)

Conditions	Yield
Stage #1: 2-Ethylbutanoic acid With cyclopentyl methyl ether; ammonia at 200℃; under 4500.45 Torr; Sealed tube; Green chemistry; Stage #2: With cyclopentyl methyl ether; ammonia; hydrogen at 200℃; under 42004.2 Torr; for 48h; Cooling with ice; Green chemistry;	A 85% B 3% C 9%

2-Ethylbutanoic acid (88-09-5) + methyl 2-isocyano-3,3-diphenyl acrylate (76203-05-9) → methyl 4-phenyl-1-(pentan-3-yl)isoquinoline-3-carboxylate

Conditions	Yield
With potassium phosphate; dipotassium peroxodisulfate; silver carbonate In water; acetonitrile at 70℃; for 4h; Inert atmosphere;	84%

2-Ethylbutanoic acid (88-09-5) + (E)-3-phenylacrylic acid (140-10-3) → 3-Aethyl-1-phenyl-penten-(1) (15314-18-8)

Conditions	Yield
With dipotassium peroxodisulfate; copper; silver nitrate In water; acetonitrile at 90℃; for 12h;	82%

2-Ethylbutanoic acid (88-09-5) + 2-phenyl-1,2,3,4-tetrahydroisoquinoline (3340-78-1) + [(p-methylphenyl)sulfonylmethyl]isonitrile (38622-91-2, 36635-61-7) → N-(2-ethylbutanoyl)-2-phenyl-N-(tosylmethyl)-1,2,3,4-tetrahydroisoquinoline-1-carboxamide

Conditions	Yield
With diethylazodicarboxylate In dichloromethane at 20℃; for 4h; Ugi Condensation;	82%

Upstream product

• 79-21-0 peracetic acid 
• 928-49-4 hex-3-yne 
• 97-96-1 2-Ethylbutyraldehyde 
• 60-29-7 diethyl ether 
• 7493-69-8 allyl 2-ethylbutyrate 
• 1809-05-8 3-pentyl iodide 
• 151-50-8 potassium cyanide 
• 4386-07-6 2-ethyl-2-cyano-butyric acid 
• 85153-63-5 2,2-diethyl-acetoacetic acid methyl ester 
• 510-20-3 diethyl malonic acid 
• 3898-61-1 diethylketene dimer 
• 141-78-6 ethyl acetate 
• 760-21-4 2-ethyl-1-butene 
• 1619-57-4 ethyl 2,2-diethyl-3-oxobutanoate 

Downstream Products

• 5451-22-9 2-ethyl-butyric acid-(3-tetrahydro[2]furyl-propyl ester) 
• 816-11-5 2-ethyl-butyric acid methyl ester 
• 97-95-0 2-ethyl-1-butanol 
• 2736-40-5 chlorure d'acide ethyl-2 butyrique 
• 26464-06-2 2-ethyl-butyryl bromide 
• 26074-53-3 2-bromo-2-ethylbutyryl bromide 
• 5456-23-5 2-ethyl-2-bromo-butyric acid 
• 54502-37-3 2-ethylbutyric anhydride 
• 107-87-9 2-Pentanone 
• 5429-31-2 8-(1-ethyl-propyl)-1,3-dimethyl-3,7-dihydro-purine-2,6-dione 
• 6137-03-7 3-ethyl-2-pentanone 
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Relevant articles and documents

Ruthenium-catalysed hydroxycarbonylation of olefins

State-of-the-art catalyst systems for hydroxy- and alkoxycarbonylations of olefins make use of palladium complexes. In this work, we report a complementary ruthenium-catalysed hydroxycarbonylation of olefins applying an inexpensive Ru-precursor (Ru3(CO)12) and PCy3as a ligand. Crucial for the success of this transformation is the use of hexafluoroisopropanol (HFIP) as the solvent in the presence of an acid co-catalyst (PTSA). Overall, moderate to good yields are obtained using aliphatic olefins including the industrially relevant substrate di-isobutene. This atom-efficient catalytic transformation provides straightforward access to various carboxylic acids from unfunctionalized olefins.

Dehydrogenation of Alcohols to Carboxylic Acid Catalyzed by in Situ-Generated Facial Ruthenium- CPP Complex

A selective catalytic system for the dehydrogenation of primary alcohols to carboxylic acids using a facial ruthenium complex generated in situ from the [Ru(COD)Cl2]n and a hybrid N-heterocyclic carbene (NHC)-phosphine-phosphine ligand (CPP) has been first reported. The facial coordination model was unveiled by NMR analysis of the reaction mixture. Such a fac-ruthenium catalyst system exhibited high catalytic activity and stability, and a high turnover number of 20 000 could be achieved with catalyst loading as low as 0.002 mol %. The exceedingly high catalyst stability was tentatively attributed to both the anchoring role of NHC and the hemi-lability of phosphines. The catalytic system also features a wide substrate scope. In particular, the facial coordination of CPP ligands was found to be beneficial for sterically hindered alcohols, and ortho-substituted benzylic alcohols and bulky adamantanyl methanol as well as cholesterol were all found to be viable dehydrogenation substrates.

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The invention relates to novel compounds (I), the use of compounds in eliciting a pro-Th17 immune response and related aspects. Further provided are methods of production of said compounds (I).