625-23-0

Basic information

• Product Name: 2-METHYL-2-HEXANOL
• Synonyms: 2-methyl-2-hexanoI;2-Methyl-2-hydroxyhexane;Butyldimethylcarbinol;Methyl-2 hexanol-2;N-BUTYLDIMETHYLCARBINOL;1,1-DIMETHYL-1-PENTANOL;2-METHYL-2-HEXANOL;2-methylhexan-2-ol
• CAS NO: 625-23-0
• Molecular Formula: C₇H₁₆O
• Molecular Weight: 116.2
• EINECS: 210-881-5
• Product Categories: Alcohols;C7 to C8;Oxygen Compounds
• Mol File: 625-23-0.mol
• Article Data: 16

Chemical Properties

• Melting Point: -30.45°C (estimate)
• Boiling Point: 141-142 °C(lit.)
• Flash Point: 105 °F
• Appearance: /
• Density: 0.812 g/mL at 25 °C(lit.)
• Vapor Pressure: 2.2mmHg at 25°C
• Refractive Index: n20/D 1.417(lit.)
• Storage Temp.: Flammables area
• PKA: 15.38±0.29(Predicted)
• Water Solubility: 9.61g/L(25 oC)
• CAS DataBase Reference: 2-METHYL-2-HEXANOL(CAS DataBase Reference)
• NIST Chemistry Reference: 2-METHYL-2-HEXANOL(625-23-0)
• EPA Substance Registry System: 2-METHYL-2-HEXANOL(625-23-0)

Safety Data

• Statements: 10
• Safety Statements: 16
• RIDADR: UN 1987 3/PG 3
• WGK Germany: 3
• HazardClass: 3.2
• PackingGroup: III
• Hazardous Substances Data: 625-23-0(Hazardous Substances Data)

Usage

Chemical Properties

CLEAR COLOURLESS TO LIGHT YELLOW LIQUID

Uses

2-Methyl-2-hexanol was used in the preparation of esterified phenol. It is used to study the effect of organic solvent on the equillibrium of lipase-catalyzed esterification of glycerol and decanoic acid.

InChI:InChI=1/C7H16O/c1-4-5-6-7(2,3)8/h8H,4-6H2,1-3H3

Synthetic route

n-hexan-2-one (591-78-6) + MeTiCl3 → 2-methylhexan-2-ol (625-23-0) + rac-octan-2-ol (4128-31-8)

Conditions	Yield
With heptanal; 1,2-bis-(diphenylphosphino)ethane In dichloromethane at 0℃; for 6h;	A 95% B 27%

butyl magnesium bromide (693-04-9) + 2,3,3-trimethyl-2-butyl peroxybenzoate (99051-01-1) → 2-methylhexan-2-ol (625-23-0) + phenyl butyl ketone (1009-14-9) + 5-phenylnonan-5-ol (1855-13-6) + 2-Butoxy-2,3,3-trimethyl-butane

Conditions	Yield
In diethyl ether at 0℃; for 2h;	A 14% B 2% C 9% D 86%

heptanal (111-71-7) + methyltrichlorotitanium (2747-38-8) → 2-methylhexan-2-ol (625-23-0) + rac-octan-2-ol (4128-31-8)

Conditions	Yield
With n-hexan-2-one In dichloromethane at -25℃; for 6h;	A 3% B 74%
With n-hexan-2-one; Methyltitantrichlorid,Triphenylphosphin In dichloromethane at -25℃; for 6h; Product distribution; other phosphane-complexes and reagents;	A 67% B 10%

n-hexan-2-one (591-78-6) + methyl iodide (74-88-4) → 2-methylhexan-2-ol (625-23-0) + 5,6-Dimethyl-decane-5,6-diol (97795-56-7)

Conditions	Yield
With Pr 1.) THF, 20 deg C, 2.) -20 deg C;	A 70% B 7%

1-bromo-butane (109-65-9) + acetone (67-64-1) → 2-methylhexan-2-ol (625-23-0)

Conditions	Yield
Stage #1: 1-bromo-butane With magnesium In tetrahydrofuran Inert atmosphere; Schlenk technique; Stage #2: acetone In tetrahydrofuran at 0℃; Inert atmosphere; Schlenk technique; Stage #3: With hydrogenchloride; water In tetrahydrofuran at 0℃; Inert atmosphere; Schlenk technique;	67%
With magnesium	62%
(i) Mg, (ii) /BRN= 635680/; Multistep reaction;

n-hexan-2-one (591-78-6) + methyltrichlorotitanium (2747-38-8) → 2-methylhexan-2-ol (625-23-0) + rac-octan-2-ol (4128-31-8)

Conditions	Yield
With heptanal; Methyltitantrichlorid,Triphenylphosphin In dichloromethane at -25℃; for 6h; Product distribution; other phosphane-complexes and reagents;	A 67% B 10%

n-butyllithium (109-72-8, 29786-93-4) + 2,3,3-trimethyl-2-butyl peroxybenzoate (99051-01-1) → 2-methylhexan-2-ol (625-23-0) + phenyl butyl ketone (1009-14-9) + 5-phenylnonan-5-ol (1855-13-6) + 2-Butoxy-2,3,3-trimethyl-butane

Conditions	Yield
In hexane at 0℃; for 2h;	A 30% B 36% C 26% D 22%

n-butyllithium (109-72-8, 29786-93-4) + 2,3,3-trimethyl-2-butyl peroxybenzoate (99051-01-1) → 2-methylhexan-2-ol (625-23-0) + 2,3,3-trimethyl-2-butanol (594-83-2) + 5-phenylnonan-5-ol (1855-13-6) + 2-Butoxy-2,3,3-trimethyl-butane

Conditions	Yield
In hexane at 0℃; for 2h;	A 30% B 30% C 26% D 22%

β,β-dibromovinyl methyl ether (85371-47-7) + acetone (67-64-1) → 2-methylhexan-2-ol (625-23-0) + 4-Methoxy-2-methylbut-3-yne-2-ol (36677-85-7) + (E)-3-Bromo-4-methoxy-2-methyl-3-buten-2-ol (85371-42-2) + (Z)-3-Bromo-4-methoxy-2-methyl-3-buten-2-ol (85371-43-3)

Conditions	Yield
With n-butyllithium In tetrahydrofuran at -80℃;	A n/a B 15% C n/a D n/a

2-methyl-1,2-epoxypropane (558-30-5) + di-n-propylmagnesium (4907-44-2) → 2-methylhexan-2-ol (625-23-0)

Conditions	Yield
With diethyl ether

ethyl n-valerate (539-82-2) + methylmagnesium bromide (75-16-1) → 2-methylhexan-2-ol (625-23-0)

bis-(1,1-dimethyl-pentyl)-peroxide (106422-41-7) → 2,2,5-Trimethyl-tetrahydro-furan (82004-72-6) + 2-methylhexan-2-ol (625-23-0) + methane (34557-54-5) + acetone (67-64-1)

Conditions	Yield
at 120℃; under 30 Torr; Produkt5: 2,3-Epoxy-2-methyl-hexan, Produkt6: 4-Aethyl-2,2-dimethyl-oxetan;

ethene (74-85-1) + isopropyl alcohol (67-63-0) → 2-methylhexan-2-ol (625-23-0)

Conditions	Yield
With di-tert-butyl peroxide

n-butyl magnesium bromide (693-03-8) + acetone (67-64-1) → 2-methylhexan-2-ol (625-23-0)

Conditions	Yield
In diethyl ether at 20℃; Rate constant;
With diethyl ether

2-methyl-3,5-hexadiyn-2-ol (763-12-2) → 2-methylhexan-2-ol (625-23-0)

Conditions	Yield
With hydrogen; palladium In ethyl acetate

2-chloro-2-methylhexane (4398-65-6) → 2-methylhexan-2-ol (625-23-0)

Conditions	Yield
With silver carbonate In pentane at 20℃; for 20h;

dimethyl(vinylethynyl)carbinol (690-94-8) → 2-methylhexan-2-ol (625-23-0)

Conditions	Yield
With hydrogen; Lindlar's catalyst In methanol

1,1-dimethylpentyl hydroperoxide (14474-79-4) → 2-methylhexan-2-ol (625-23-0)

Conditions	Yield
With sulfuric acid; iron(II) sulfate
With (thermolysis) In benzene at 135.2 - 161℃; Kinetics;

5-hydroxy-5-methyl-hex-3-en-2-one (5369-61-9) → 2-methylhexan-2-ol (625-23-0)

Conditions	Yield
With hydrogenchloride; mercury; zinc

n-butyllithium (109-72-8, 29786-93-4) + acetone (67-64-1) → 2-methylhexan-2-ol (625-23-0)

Conditions	Yield
In diethyl ether
(i) 3,3,3-trifluoro-propene, (ii) /BRN= 635680/; Multistep reaction;
In hexane at -78℃;
In hexane at -5 - 25℃; for 0.5h;

n-butyllithium (109-72-8, 29786-93-4) + butyl magnesium bromide (693-04-9) + 2,3,3-trimethyl-2-butyl peroxybenzoate (99051-01-1) → 2-methylhexan-2-ol (625-23-0) + phenyl butyl ketone (1009-14-9) + 2-Butoxy-2,3,3-trimethyl-butane + (1,1,2,2-Tetramethyl-propoxy)-benzene + benzoic acid (65-85-0)

Conditions	Yield
In hexane at 0℃; Mechanism; Product distribution; various organometallic compounds, various products by a SET mechanism;

2-methyl-2-hexene (2738-19-4) → 2-methylhexan-2-ol (625-23-0) + (±)-2-methylhex-1-en-3-ol (1838-82-0) + rac-5-methylhex-4-en-3-ol (53555-59-2) + trans-2-Methylhex-3-en-2-ol (69514-49-4) + isopropyl alcohol (67-63-0) + butan-1-ol (71-36-3)

Conditions	Yield
With lithium aluminium tetrahydride; oxygen Product distribution; multistep reaction: 1) 70 deg C, 101,3 kPa, 15 h;	A 36 % Chromat. B n/a C n/a D 21 % Chromat. E 4 % Chromat. F 3 % Chromat.

2-methyl-1-hexene (6094-02-6) → 2-methylhexan-2-ol (625-23-0)

Conditions	Yield
With oxygen; CoSMDPT Product distribution; var. reag.: H2O2, CH3COOH or K2O/18-crown-6; var. solv.;

2-methyl-1-hexene (6094-02-6) → 2-methylhexan-2-ol (625-23-0) + 2-methylenehexan-1-ol (50965-90-7) + (±)-2-methylhex-1-en-3-ol (1838-82-0) + n-hexan-2-ol (626-93-7) + (-)S-2-methyl-hexane-1,2-diol (56255-50-6) + 2-methyl-2-hexen-1-ol Z isomer (62594-06-3)

Conditions	Yield
With lithium aluminium tetrahydride; oxygen Product distribution; multistep reaction: 1) 70 deg C, 101,3 kPa, 85 h;	A 37 % Chromat. B n/a C 13 % Chromat. D 22 % Chromat. E 15 % Chromat. F n/a

n-hexan-2-one (591-78-6) + methylmagnesium bromide (75-16-1) → 2-methylhexan-2-ol (625-23-0)

Conditions	Yield
bis(cyclopentadienyl)titanium dichloride In diethyl ether for 0.333333h; Yield given;
bis(cyclopentadienyl)titanium dichloride In diethyl ether Mechanism; var. of ketones, var. aldehydes and var. Grignards as reactants;

n-hexan-2-one (591-78-6) + dimethylmagnesium (2999-74-8) → 2-methylhexan-2-ol (625-23-0)

Conditions	Yield
In tetrahydrofuran-d8 at -70℃; Rate constant;

2-Methylhexane (591-76-4) → 2-methylhexan-2-ol (625-23-0)

Conditions	Yield
With 3,3-dimethyldioxirane In acetone Rate constant; Ambient temperature;
With oxalic acid; Mn2(IV) complex with 1,4,7-trimethyl-1,4,7-triazacyclononane In acetonitrile at 50℃;
Stage #1: 2-Methylhexane With dihydrogen peroxide In water; acetonitrile at 20℃; Irradiation; Stage #2: With triphenylphosphine In water; acetonitrile

acetone (67-64-1) + 1-halo-butane → 2-methylhexan-2-ol (625-23-0)

Conditions	Yield
With magnesium

valeric acid (109-52-4) + methyl magnesium halide → 2-methylhexan-2-ol (625-23-0)

Conditions	Yield
With benzene bei 2-stdg.Kochen;

2-methylhexan-2-ol (625-23-0) → 2-chloro-2-methylhexane (4398-65-6)

Conditions	Yield
With gallium(III) trichloride; dimethylmonochlorosilane In dichloromethane; pentane at 20℃; for 1.5h; Inert atmosphere;	99%
With hydrogenchloride	95%
With hydrogenchloride; sulfuric acid

Isopropenyl acetate (108-22-5) + 2-methylhexan-2-ol (625-23-0) → 2-methylhexan-2-yl acetate (34650-24-3)

Conditions	Yield
With Cp*2Sm(THF)2; cyclohexanone oxime acetate In toluene at 25℃; for 15h; Product distribution; Mechanism; various alcohols under different reaction conditions;	99%
With Cp*2Sm(THF)2; cyclohexanone oxime acetate In toluene at 25℃; for 15h;	99%
With Cp*2Sm(THF)2 In toluene Ambient temperature;	51%

2-methylhexan-2-ol (625-23-0) + acetic anhydride (108-24-7) → 2-methylhexan-2-yl acetate (34650-24-3)

Conditions	Yield
zinc(II) perchlorate at 20℃; for 0.333333h;	99%
With pyridine; dmap at 70℃; for 16h;

2-methylhexan-2-ol (625-23-0) + recorcinol (108-46-3) → 4-tert-heptylresorcinol (131941-94-1) + 4,6-di-tert-heptylresorcinol (131941-96-3)

Conditions	Yield
With sulfuric acid at 70℃;	A 1.6% B 95.1%

2-methylhexan-2-ol (625-23-0) + 1,1,1,3,3,3-hexamethyl-disilazane (999-97-3) → 2-Methylhexyl-2-oxy(trimethyl)silan (81588-99-0)

Conditions	Yield
With (toluene-4-sulfonyl)-amidophosphoric acid bis-(4-nitro-phenyl ester) at 140℃; for 0.25h;	92%
With dimesylamine at 140℃; for 0.5h;	92%

2-methylhexan-2-ol (625-23-0) + t-butyldimethylsiyl triflate (69739-34-0) → tert-butyldimethyl((2-methylhexan-2-yl)oxy)silane (1612763-83-3)

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃;	90%

2-methylhexan-2-ol (625-23-0) + methyl selenide (6486-05-1) → 2-Methyl-2-methylselanyl-hexane (92976-65-3)

Conditions	Yield
With zinc(II) chloride In 1,2-dichloro-ethane at 80℃; for 1h;	88%

2-methylhexan-2-ol (625-23-0) → 2-bromo-2-methylhexane (70351-82-5)

Conditions	Yield
With hydrogen bromide; lithium bromide In diethyl ether; water at 0℃; Inert atmosphere; Schlenk technique;	87%
With hydrogen bromide; calcium chloride
With hydrogen bromide
With hydrogen bromide; lithium bromide In water at 20℃; Inert atmosphere;
With hydrogen bromide; lithium bromide In dichloromethane; water at 0 - 20℃; Inert atmosphere;

2-methylhexan-2-ol (625-23-0) + trimethylsilyldimesylamine (30488-04-1) → 2-Methylhexyl-2-oxy(trimethyl)silan (81588-99-0)

Conditions	Yield
In chloroform Heating;	86%

2-methylhexan-2-ol (625-23-0) + 3-Thiophene carboxylic acid (88-13-1) → 2-methyl-2-hexyl thiophene-3-carboxylate

Conditions	Yield
With dmap; diisopropyl-carbodiimide In dichloromethane	85%
With 2-chloro-3,5-dinitropyridine In pyridine at 115℃; for 0.75h;	47%

2-methylhexan-2-ol (625-23-0) + triisopropylsilyl trifluoromethanesulfonate (80522-42-5) → triisopropyl((2-methylhexan-2-yl)oxy)silane (1612763-84-4)

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃;	84%

2-bromothiophene-4-carboxylic acid (100523-84-0) + 2-methylhexan-2-ol (625-23-0) → C12H17BrO2S (1248336-06-2)

Conditions	Yield
With dmap; diisopropyl-carbodiimide In dichloromethane	77%

2-methylhexan-2-ol (625-23-0) + 3,3,4-trichloro-3-butenoyl chloride (484067-66-5) → 3,4,4-trichloro-but-3-enoic acid 1,1-dimethyl-pentyl ester

Conditions	Yield
With pyridine In diethyl ether at 20 - 23℃; for 22h;	73%

2-methylhexan-2-ol (625-23-0) + trimethylsilylazide (4648-54-8) → 2-azido-2-methylhexane (76613-34-8)

Conditions	Yield
With boron trifluoride diethyl etherate In benzene at 20℃; for 24h; Inert atmosphere;	67%

2-methylhexan-2-ol (625-23-0) → 2-methyl-5-chloro-2-hexanol (82004-70-4)

Conditions	Yield
With lead(IV) acetate; lithium chloride In benzene at 80℃;	64%
Multi-step reaction with 2 steps 1: acetic acid, calcium hypochlorite / CCl4; H2O / 0 °C / in dark 2: 48 percent / FeSO4*7H2O, NaHCO3 / CCl4 / Ambient temperature; protected from the light View Scheme
Multi-step reaction with 2 steps 1: aq. H2SO4, aq. H2O2 2: FeSO4*7H2O, CuCl2*4H2O, aq. HCl / CCl4 View Scheme
Multi-step reaction with 5 steps 1: boron trifluoride diethyl etherate / dichloromethane / 1 h / 0 - 20 °C 2: hydrazine hydrate / ethanol / 5 h / 20 °C 3: acetic acid / ethanol / 12 h 4: lithium hydroxide monohydrate / water; methanol / 20 °C 5: caesium carbonate; (4s,6s)-2,4,5,6-tetra(9H-carbazol-9-yl)isophthalonitrile; Ethyl trichloroacetate / acetonitrile / 18 h / 40 °C / Inert atmosphere; Irradiation View Scheme

2-methylhexan-2-ol (625-23-0) + benzene-1,2-diol (120-80-9) → 4-(1,1-Dimethylpentyl)-1,2-benzenediol (100186-17-2)

Conditions	Yield
With Wofatit OK 80 In xylene at 140 - 145℃;	63%
With sulfuric acid In trifluoroacetic acid at 40℃; for 16h;	36%

Thiophene-2-thiol (7774-74-5) + 2-methylhexan-2-ol (625-23-0) → 2-[(2-methylhex-2-yl)thio]thiophene

Conditions	Yield
With boron trifluoride diethyl etherate In diethyl ether; dichloromethane at -10℃; for 2h; Inert atmosphere;	62%

2-methylhexan-2-ol (625-23-0) + methyl isoquinoline-3-carboxylate (27104-73-0) → C18H23NO3

Conditions	Yield
With tris(2,2'-bipyridyl)ruthenium dichloride; 4,5,6,7-tetrafluoro-1-hydroxybenzo[d][1,2]iodaoxol-3(1H)-one at 30℃; Minisci Aromatic Substitution; Inert atmosphere; Irradiation; chemoselective reaction;	60%

C6H4NCH2CHCCH2 (491-35-0) + 2-methylhexan-2-ol (625-23-0) → C17H23NO

Conditions	Yield
With dipotassium peroxodisulfate; sulfuric acid; silver nitrate In water at 50℃; for 24h; Inert atmosphere; Sealed tube; regioselective reaction;	47%

2,5-dibromothiophene-3-carboxylic acid (7311-70-8) + 2-methylhexan-2-ol (625-23-0) → 2-methyl-2-hexyl 2,5-dibromothiophene-3-carboxylate

Conditions	Yield
With pyridine; 2-chloro-3,5-dinitropyridine at 115℃; for 0.5h;	46%

2-methylhexan-2-ol (625-23-0) + Triethylsilyl trifluoromethanesulfonate (79271-56-0) → triethyl((2-methylhexan-2-yl)oxy)silane (1612763-82-2)

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃;	46%

2-methylhexan-2-ol (625-23-0) + urea (57-13-6) → (1,1-dimethylpent-1-yl)urea (108302-62-1)

Conditions	Yield
With sulfuric acid at 20 - 25℃;	45%
With sulfuric acid

2-methylhexan-2-ol (625-23-0) + cyclohexane (110-82-7) + carbon monoxide (201230-82-2) → 2-methylhexan-2-yl cyclohexanecarboxylate

Conditions	Yield
With di-tert-butyl peroxide; triphenylphosphine; palladium dichloride In 1,2-dichloro-ethane at 110℃; under 3800.26 Torr; for 24h; Autoclave;	40%

Upstream product

• 558-30-5 2-methyl-1,2-epoxypropane 
• 4907-44-2 di-n-propylmagnesium 
• 74-85-1 ethene 
• 67-63-0 isopropyl alcohol 
• 4398-65-6 2-chloro-2-methylhexane 
• 14474-79-4 1,1-dimethylpentyl hydroperoxide 
• 5369-61-9 5-hydroxy-5-methyl-hex-3-en-2-one 
• 109-65-9 1-bromo-butane 
• 67-64-1 acetone 
• 109-72-8 n-butyllithium 
• 6094-02-6 2-methyl-1-hexene 
• 591-78-6 n-hexan-2-one 
• 2747-38-8 methyltrichlorotitanium 
• 75-16-1 methylmagnesium bromide 

Downstream Products

• 4398-65-6 2-chloro-2-methylhexane 
• 19219-89-7 2-Methyl-2-phenylhexane 
• 14474-79-4 1,1-dimethylpentyl hydroperoxide 
• 100859-79-8 2,3-dibromo-2-methyl-hexane 
• 106522-91-2 4-(1,1-dimethyl-pentyl)-anisole 
• 1636888-31-7 (1,1-dimethylpentyl)trichlorosilane 
• 6496-48-6 2,2,5-trimethylpyrrolidine 
• 1812-50-6 2-methylhexane-2-thiol 
• 1612763-84-4 triisopropyl((2-methylhexan-2-yl)oxy)silane 
• 1248336-06-2 C₁₂H₁₇BrO₂S 
• 95493-79-1 4-Nitro-perbenzoesaeure-<1.1-dimethyl-pentylester> 
• 108618-85-5 (2,2-dimethyl-hexyl)-benzene 
• 107918-26-3 1-cyclohexyl-2,2-dimethyl-hexane 
• 2626-64-4 2-Amino-2-methyl-hexan 

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