3302-10-1

Basic information

• Product Name: 3,5,5-Trimethylhexanoic acid
• Synonyms: RARECHEM AL BE 0197;TIMTEC-BB SBB005782;3,5,5-trimethyl-hexanoicaci;Hexanoic acid, 3,5,5-trimethyl-;3,3,5-TRIMETHYLHEXANOIC ACID;3,5,5-TRIMETHYLHEXANOIC ACID;TMHA;3,5,5-Trimethlhexanoic acid
• CAS NO: 3302-10-1
• Molecular Formula: C₉H₁₈O₂
• Molecular Weight: 158.24
• EINECS: 221-975-0
• Product Categories: Organic acids
• Mol File: 3302-10-1.mol
• Article Data: 20

Chemical Properties

• Melting Point: -70°C
• Boiling Point: 121 °C (10 mmHg)
• Flash Point: 125°C
• Appearance: clear liquid
• Density: 0,91 g/cm3
• Vapor Pressure: 0.0107mmHg at 25°C
• Refractive Index: 1.4278-1.4298
• Solubility: Miscible with the usual organic solvents.
• PKA: 4.80±0.10(Predicted)
• Water Solubility: 700mg/L at 20℃
• Stability: Stable. Incompatible with reactive metals, strong oxidizing agents.
• BRN: 1749506
• CAS DataBase Reference: 3,5,5-Trimethylhexanoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 3,5,5-Trimethylhexanoic acid(3302-10-1)
• EPA Substance Registry System: 3,5,5-Trimethylhexanoic acid(3302-10-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 24/25
• RIDADR: 3265
• TSCA: Yes
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 3302-10-1(Hazardous Substances Data)

Usage

Description

3,5,5-Trimethylhexanoic acid, also known as isovaleric acid, is an organic compound with the chemical formula C8H16O2. It is a colorless liquid and serves as an important intermediate in various chemical syntheses.

Uses

Used in Organic Synthesis:
3,5,5-Trimethylhexanoic acid is used as a key intermediate for the synthesis of various organic compounds. Its versatile structure allows for the creation of a wide range of products, making it a valuable component in the chemical industry.
Used in Pharmaceutical Industry:
3,5,5-Trimethylhexanoic acid is utilized as a crucial raw material in the development and production of pharmaceuticals. Its unique properties enable it to be incorporated into the structures of various drugs, contributing to their efficacy and function.
Used in Agrochemicals:
In the agrochemical industry, 3,5,5-Trimethylhexanoic acid is employed as a vital component in the formulation of various products. Its presence in these formulations aids in enhancing their performance and effectiveness in agricultural applications.
Used in Dye Industry:
3,5,5-Trimethylhexanoic acid is also used as a significant raw material in the dye industry. Its incorporation into dye formulations helps to improve their color properties and stability, making it an essential component in the production of various dyes.

Flammability and Explosibility

Nonflammable

InChI:InChI=1/C9H18O2/c1-7(5-8(10)11)6-9(2,3)4/h7H,5-6H2,1-4H3,(H,10,11)/p-1/t7-/m1/s1

Synthetic route

2,4,4-trimethyl-1-pentene (107-39-1) + carbon monoxide (201230-82-2) → 3,5,5-trimethylhexanoic acid (3302-10-1)

Conditions	Yield
With bis(acetylacetonato)palladium(II); 1,1’-ferrocenediyl-bis(tert-butyl(pyridin-2-yl)phosphine); toluene-4-sulfonic acid; acetic acid In water at 120℃; under 30003 Torr; for 20h; Catalytic behavior; Reagent/catalyst; Inert atmosphere; Autoclave;	99%
With palladium(II) acetylacetonate; 1,1’-ferrocenediyl-bis(tert-butyl(pyridin-2-yl)phosphine); toluene-4-sulfonic acid; acetic acid In water at 120℃; under 30003 Torr; for 20h; Reagent/catalyst; Sealed tube; Inert atmosphere; Autoclave;	99%
With bis(acetylacetonato)palladium(II); trifluorormethanesulfonic acid; 1,1’-ferrocenediyl-bis(tert-butyl(pyridin-2-yl)phosphine) In water at 120℃; under 30003 Torr; for 2h; Inert atmosphere; Autoclave;
With sulfuric acid; 1,1’-ferrocenediyl-bis(tert-butyl(pyridin-2-yl)phosphine); water; palladium(II) acetylacetonate; acetic acid at 120℃; under 11251.1 - 18751.9 Torr; for 3h; Koch-Haaf Carboxylation; Autoclave; Inert atmosphere;
With bis(acetylacetonato)palladium(II); sulfuric acid; 1,1’-ferrocenediyl-bis(tert-butyl(pyridin-2-yl)phosphine); acetic acid In water at 120℃; under 11251.1 Torr; for 3h; Inert atmosphere; Autoclave;

3,5,5-trimethyl hexanal (5435-64-3) → 3,5,5-trimethylhexanoic acid (3302-10-1)

Conditions	Yield
With oxygen; valerianate de potassium; iron In water at 60℃; for 6h; Product distribution / selectivity;	98.5%
With oxygen; potassium isononanoate In water at 60℃; for 6h; Product distribution / selectivity;	97.6%
With oxygen; iron at 60℃; for 6h; Product distribution / selectivity;	96.4%

2,4,4-trimethyl-1-pentene (107-39-1) + formic acid (64-18-6) + 2,4,4-trimethylpent-2-ene (107-40-4) → 3,5,5-trimethylhexanoic acid (3302-10-1)

Conditions	Yield
With pyadbpx; palladium diacetate; toluene-4-sulfonic acid In tetrahydrofuran; water at 100℃; for 20h; Inert atmosphere; Schlenk technique; Sealed tube;	95%

isononanol (3452-97-9, 140237-84-9, 140237-85-0) → 3,5,5-trimethylhexanoic acid (3302-10-1)

Conditions	Yield
With sodium tungstate (VI) dihydrate; dihydrogen peroxide; methyl tri-n-octyl ammonium hydrogen sulfate at 90℃; for 4h; pH=1; Reagent/catalyst; Temperature; pH-value;	91%
With chromium(VI) oxide; acetic acid
Multi-step reaction with 2 steps 1: air; silver / 410 - 430 °C 2: air; magnesium acetate; glacial acetic acid / 25 °C View Scheme
With oxygen; palladium diacetate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In water at 100℃; for 48h;	47 %Spectr.

3,5,5-trimethyl hexanal (5435-64-3) → 3,5,5-trimethylhexanamide (90726-43-5) + 3,5,5-trimethylhexanoic acid (3302-10-1)

Conditions	Yield
With H2SO4*2NH2OH; Rh(OH)x/Al2O3 In water for 7h; Heating;	A 81% B 5 % Chromat.

5,5-dimethyl-3-methylenehexanoic acid (90252-84-9) → 3,5,5-trimethylhexanoic acid (3302-10-1)

Conditions	Yield
With hydrogen; platinum(IV) oxide In methanol; water

bis(3,5,5-trimethylhexanoyl) peroxide (3851-87-4) → 2,2,4-trimethylpentane (540-84-1) + 2,4,4-trimethylpentan-1-ol (16325-63-6) + 2,2,4,7,9,9-hexamethyldecane (72493-27-7) + 3,5,5-trimethylhexanoic acid (3302-10-1) + bis(3,5,5-trimethylhexanoic) anhydride (94376-47-3) + 2,4,4-trimethylpentyl 3,5,5-trimethylhexanoate

Conditions	Yield
With pentadecane at 80℃; under 750060 Torr; Product distribution; Rate constant; Thermodynamic data; var. of temp., pressure, solvent, EA, ΔV(excit.);	A 0.625 mol B 0.009 mol C 0.394 mol D 0.038 mol E 0.005 mol F 0.126 mol

bis(3,5,5-trimethylhexanoyl) peroxide (3851-87-4) → 3,5,5-trimethylhexanoic acid (3302-10-1) + 2,4,4-trimethylpentyl 3,5,5-trimethylhexanoate

Conditions	Yield
With 2-methylundecane In acetonitrile at 70℃; under 1500120 Torr; for 16h; Rate constant; Thermodynamic data; Kinetics; var. of solvent, temp., pressure, without additive, EA, ΔV(excit.);

3,5,5-trimethyl-hexanal-dimethylacetal → 3,5,5-trimethylhexanoic acid (3302-10-1)

Conditions	Yield
With formic acid; oxygen; cobalt(II) acetate

3,5,5-trimethyl-hexane-1,1-dithiol (408340-33-0) + nitric acid (7697-37-2) → 3,5,5-trimethylhexanoic acid (3302-10-1) + 2,4,4-trimethylpentanoic acid (3302-09-8)

1-hydroxy-3,5,5-trimethyl-hexyl hydroperoxide (86178-10-1) → 3,5,5-trimethylhexanoic acid (3302-10-1) + water (7732-18-5)

Conditions	Yield
beim Erhitzen;

2,4,4-trimethyl-1-pentene (107-39-1) → 3,5,5-trimethylhexanoic acid (3302-10-1)

Conditions	Yield
Multi-step reaction with 3 steps 1: KCl / liquid sulphur dioxide 2: water / und anschliessenden Erhitzen 3: H2 / PtO2 / methanol; H2O View Scheme

(3-neopentyl-but-3-enoyl)-sulfamoyl chloride (92442-17-6) → 3,5,5-trimethylhexanoic acid (3302-10-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: water / und anschliessenden Erhitzen 2: H2 / PtO2 / methanol; H2O View Scheme

2,4,4-trimethyl-1-pentene (107-39-1) + acetic acid (64-19-7) → 3,5,5-trimethylhexanoic acid (3302-10-1)

Conditions	Yield
With palladium(II) acetylacetonate; carbon monoxide; 1,1’-ferrocenediyl-bis(tert-butyl(pyridin-2-yl)phosphine); toluene-4-sulfonic acid; palladium at 20 - 120℃; under 30003 Torr; for 20h; Inert atmosphere; Autoclave;
With palladium(II) acetylacetonate; carbon monoxide; sulfuric acid; 1,1’-ferrocenediyl-bis(tert-butyl(pyridin-2-yl)phosphine); palladium In water at 20 - 120℃; under 11251.1 - 18751.9 Torr; for 3h; Inert atmosphere; Autoclave;

2,4,4-trimethyl-1-pentene (107-39-1) + 2,4,4-trimethylpent-2-ene (107-40-4) + oct-1-ene (111-66-0) + carbon monoxide (201230-82-2) → 3,5,5-trimethylhexanoic acid (3302-10-1) + nonanoic acid (112-05-0)

Conditions	Yield
With sulfuric acid; 2,2'-bis(tert-butyl(pyridin-2-yl)phosphaneyl)-1,1'-binaphthalene; acetic acid; palladium dichloride at 80℃; under 30003 Torr; for 20h; regioselective reaction;

3,5,5-trimethylhexanoic acid (3302-10-1) + zinc(II) oxide → tetrazinc μ4-oxohexa-mu.-3,5,5-trimethylhexanoate

Conditions	Yield
In toluene mixt. 3,5,5-trimethylhexanoic acid (6 equiv.) and zinc oxide (4 equiv.)and toluene heated with stirring for 3 h (water removed); product filtered, solvent removed from filtrate, purified by distillation; elem. anal.;	99%

3,5,5-trimethylhexanoic acid (3302-10-1) + 2-[(3-hydroxy-2,2-dimethylpropoxy)methyl]-2-methylpentan-1-ol → C30H58O5

Conditions	Yield
With toluene-4-sulfonic acid In toluene at 135℃; for 7h; Inert atmosphere;	99%

3,5,5-trimethylhexanoic acid (3302-10-1) + 3-(3-hydroxy-2,2-dimethylpropoxy)-2,2-dimethylpropan-1-ol (16090-01-0) → bis(3,5,5-trimethylhexanoic acid) 2,2,6,6-tetramethyl-4-oxaheptane-1,7-diyl ester

Conditions	Yield
With toluene-4-sulfonic acid In toluene at 135℃; Inert atmosphere;	96%

3,5,5-trimethylhexanoic acid (3302-10-1) → bis(3,5,5-trimethylhexanoyl) peroxide (3851-87-4)

Conditions	Yield
With dihydrogen peroxide In pentane at 70 - 80℃; for 8h; Solvent; Temperature;	94%
With dmap; dihydrogen peroxide; dicyclohexyl-carbodiimide In dichloromethane at -5 - 0℃; for 2h; Inert atmosphere;	72%
Stage #1: 3,5,5-trimethylhexanoic acid With dmap; dihydrogen peroxide In dichloromethane at -15℃; for 0.166667h; Inert atmosphere; Stage #2: With dicyclohexyl-carbodiimide In dichloromethane at -15 - 10℃; for 1.5h; Inert atmosphere;

3,5,5-trimethylhexanoic acid (3302-10-1) + 2-ethyl-2-(3-hydroxy-2,2-dimethylpropoxymethyl)hexane-1-ol → C32H62O5

Conditions	Yield
With sulfuric acid In toluene at 135℃; for 14h; Inert atmosphere;	93%

3,5,5-trimethylhexanoic acid (3302-10-1) + C6H18N3O3P (1062512-43-9) → N-methoxy-N,3,5,5-tetramethylhexanamide (1186486-23-6)

Conditions	Yield
In toluene at 60℃;	92%

3,5,5-trimethylhexanoic acid (3302-10-1) + 2-ethyl-2-(3-hydroxy-2,2-dimethylpropoxymethyl)-propane-1,3-diol → C38H72O7

Conditions	Yield
With toluene-4-sulfonic acid In toluene at 42℃; Inert atmosphere; Heating;	86%

3,5,5-trimethylhexanoic acid (3302-10-1) + dimethyl amine (124-40-3) → N,N,3,5,5-Pentamethylhexanamide

Conditions	Yield
With sodium phosphinate at 175℃; Inert atmosphere;	86%

3,5,5-trimethylhexanoic acid (3302-10-1) + 1-(2-methyl-propyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole (6649-77-0) → C24H36N2O

Conditions	Yield
With dmap; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide; acetonitrile at 20℃; for 18h;	85.5%

2-aminopyridine (504-29-0) + 3,5,5-trimethylhexanoic acid (3302-10-1) → 2-chloro-3-(4,4-dimethylpentan-2-yl)imidazo[1,2-α]pyridine

Conditions	Yield
Stage #1: 3,5,5-trimethylhexanoic acid With thionyl chloride In chloroform at 90℃; for 2h; Inert atmosphere; Sealed tube; Stage #2: 2-aminopyridine With triethylamine In chloroform at 25 - 90℃; for 6h; Inert atmosphere; Sealed tube;	83%

vinyl acetate (108-05-4) + 3,5,5-trimethylhexanoic acid (3302-10-1) → vinyl 3,5,5-trimethyl-hexanoate (86273-22-5)

Conditions	Yield
With 1,10-Phenanthroline; palladium diacetate at 140℃; under 15001.5 Torr; for 1.25h; Pressure; Reagent/catalyst; Time;	80%
With 1,10-Phenanthroline; palladium diacetate at 140℃; under 15001.5 Torr; for 1.25h;	80%
With sulfuric acid; mercury(II) diacetate at 75℃;

methanol (67-56-1) + 3,5,5-trimethylhexanoic acid (3302-10-1) → methyl 3,5,5-trimethylhexanoate (71500-39-5)

Conditions	Yield
With acetyl chloride for 4h; Inert atmosphere; Reflux;	80%

3,5,5-trimethylhexanoic acid (3302-10-1) + allylmagnesium bromide (1730-25-2) → 7,9,9-trimethyldec-1-en-5-one (84092-29-5)

Conditions	Yield
With copper(l) chloride In tetrahydrofuran for 8h; Ambient temperature;	79%

3,5,5-trimethylhexanoic acid (3302-10-1) + 1-ethyl-1H-indole-3-carbohydrazide (941867-84-1) → C20H27N3O (1442421-79-5)

Conditions	Yield
With trichlorophosphate for 6h; Reflux;	78%

vinyl propionate (105-38-4) + 3,5,5-trimethylhexanoic acid (3302-10-1) → vinyl 3,5,5-trimethyl-hexanoate (86273-22-5)

Conditions	Yield
With 1,10-Phenanthroline; palladium diacetate at 140℃; under 15001.5 Torr; for 1.25h;	77%

3,5,5-trimethylhexanoic acid (3302-10-1) + 1-acetyl-5-(2-(methylthio)ethyl)pyrrolidine-2,4-dione → 1-acetyl-3-(1-hydroxy-3,5,5-trimethylhexylidene)-5-(2-(methylthio)ethyl)pyrrolidine-2,4-dione (1527499-57-5)

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃;	74%

1H-indole-3-carboxylic acid hydrazide (15317-58-5) + 3,5,5-trimethylhexanoic acid (3302-10-1) → C18H23N3O (1442421-70-6)

Conditions	Yield
With trichlorophosphate at 80℃; for 3h;	71%

3,5,5-trimethylhexanoic acid (3302-10-1) + 1,3-diethylbarbituric acid (32479-73-5) → C17H28N2O4

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃;	71%

2-aminopyridine (504-29-0) + 3,5,5-trimethylhexanoic acid (3302-10-1) → 2-(3,5,5-trimethylhexanamido)pyridine 1-oxide

Conditions	Yield
Stage #1: 3,5,5-trimethylhexanoic acid With thionyl chloride; triethylamine In chloroform at 70℃; for 2h; Reflux; Stage #2: 2-aminopyridine With triethylamine In chloroform at 0℃; for 8h; Stage #3: With 3-chloro-benzenecarboperoxoic acid In chloroform at 20℃; for 3h;	70%

1-methyl-2(1H)-quinoxalinone (6479-18-1) + 3,5,5-trimethylhexanoic acid (3302-10-1) → 1-methyl-3-(2,4,4-trimethylpentyl)quinoxalin-2(1H)-one

Conditions	Yield
With tris(bipyridine)ruthenium(II) dichloride hexahydrate In dimethyl sulfoxide at 20℃; for 9h; Schlenk technique; Irradiation; regioselective reaction;	69%

1H-indol-3-acetohydrazide (5448-47-5) + 3,5,5-trimethylhexanoic acid (3302-10-1) → C19H25N3O (1442422-03-8)

Conditions	Yield
With trichlorophosphate at 80℃; for 5h;	66%

3,5,5-trimethylhexanoic acid (3302-10-1) → 3,5,5-trimethylhexylamine (3378-63-0) + 3,5,5-trimethylhexanamide (90726-43-5) + bis(3,5,5-trimethylhexyl)amine (926-75-0)

Conditions	Yield
Stage #1: 3,5,5-trimethylhexanoic 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 6.5h; Cooling with ice; Green chemistry;	A 60% B 21% C 14%

3,5,5-trimethylhexanoic acid (3302-10-1) + C9H14N2O4 → C18H30N2O5

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃;	42%

1-allylbarbituric acid (3685-62-9) + 3,5,5-trimethylhexanoic acid (3302-10-1) → C16H24N2O4

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃;	40%

N,N-dibutyl amino-2 ethanol (102-81-8) + 3,5,5-trimethylhexanoic acid (3302-10-1) → 3,5,5-trimethyl-hexanoic acid-(2-dibutylamino-ethyl ester) (102013-84-3)

Conditions	Yield
at 180 - 200℃;

Upstream product

• 5435-64-3 3,5,5-trimethyl hexanal 
• 107-39-1 2,4,4-trimethyl-1-pentene 
• 107-40-4 2,4,4-trimethylpent-2-ene 
• 111-66-0 oct-1-ene 
• 201230-82-2 carbon monoxide 
• 408340-33-0 3,5,5-trimethyl-hexane-1,1-dithiol 
• 7697-37-2 nitric acid 
• 3851-87-4 bis(3,5,5-trimethylhexanoyl) peroxide 
• 90252-84-9 5,5-dimethyl-3-methylenehexanoic acid 
• 64-19-7 acetic acid 
• 64-18-6 formic acid 
• 86178-10-1 1-hydroxy-3,5,5-trimethyl-hexyl hydroperoxide 
• 92442-17-6 (3-neopentyl-but-3-enoyl)-sulfamoyl chloride 
• 3452-97-9 isononanol 

Downstream Products

• 3378-63-0 3,5,5-trimethylhexylamine 
• 90726-43-5 3,5,5-trimethylhexanamide 
• 926-75-0 bis(3,5,5-trimethylhexyl)amine 
• 3851-87-4 bis(3,5,5-trimethylhexanoyl) peroxide 
• 80480-32-6 3,5,5-trimethyl-hexanoic acid N,N-dimethyl amide 
• 67707-75-9 3,5,5-trimethylhexanoic acid monoethyl ester 
• 27976-15-4 Thiosulfuric acid S-[2-(3,5,5-trimethyl-hexylamino)-ethyl] ester 
• 36727-29-4 isononanoyl chloride 

Relevant articles and documents

Method for preparing isononanoic acid from isononyl alcohol through green oxidation

The invention relates to the technical field of biological medicines, and provides a method for preparing isononanoic acid from isononyl alcohol through green oxidation. The method is used for solving the problems of complex flow, long reaction time, fire blast danger in the reaction process, waste gas generation, low product yield and the like in the isononanoic acid preparation process in the prior art. According to the method, isononyl alcohol is used as a raw material, a hydrogen peroxide solution is used as an oxidant, and a co-oxidant and a phase transfer catalyst are added for one-step oxidation under acidic conditions to prepare isononanoic acid. According to the method, isononyl alcohol is used as a raw material, 30% hydrogen peroxide is used as an oxidant, a co-oxidant and a phase transfer catalyst are added, isononanoic acid is prepared through a reaction under an acidic condition, the reaction is rapid, safe, green and environmentally friendly, the highest yield of a reaction product can reach 91%, and the catalyst can be repeatedly used.

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