56539-66-3

Basic information

• Product Name: 3-Methyl-3-methoxybutanol
• Synonyms: 3-methoxy-3-methyl-1-butano;MMB;3-METHOXY-3-METHYL-1-BUTANOL;3-METHOXY-3-METHYLBUTANOL;3-METHYL-3-METHOXYBUTANOL;3-methoxy-3-methylbutan-1-ol;3-METHOXY-3-METHYL-1-BUTANOL, 98+%;3-Methoxyisobutanol
• CAS NO: 56539-66-3
• Molecular Formula: C₆H₁₄O₂
• Molecular Weight: 118.17416
• EINECS: 260-252-4
• Product Categories: Alcohols;C2 to C6;Oxygen Compounds
• Mol File: 56539-66-3.mol
• Article Data: 5

Chemical Properties

• Melting Point: -50 °C
• Boiling Point: 173-175 °C(lit.)
• Flash Point: 160 °F
• Appearance: Clear colorless/Liquid
• Density: 0.926 g/mL at 20 °C(lit.)
• Vapor Pressure: 0.675mmHg at 25°C
• Refractive Index: n20/D 1.428(lit.)
• PKA: 15.19±0.10(Predicted)
• Water Solubility: Soluble in water.
• BRN: 1732882
• CAS DataBase Reference: 3-Methyl-3-methoxybutanol(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Methyl-3-methoxybutanol(56539-66-3)
• EPA Substance Registry System: 3-Methyl-3-methoxybutanol(56539-66-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36
• Safety Statements: 23-24/25-36/37/39-26
• WGK Germany: 3
• TSCA: Yes
• Hazardous Substances Data: 56539-66-3(Hazardous Substances Data)

Usage

Chemical Properties

clear colourless liquid

Uses

Different sources of media describe the Uses of 56539-66-3 differently. You can refer to the following data:
1. 3-Methoxy-3-methyl-1-butanol is a solvent that compares favorably with its isomer ethylene glycol monobutyl ether. It is employed as raw material for the production of industrial detergents. It is also used as solvent for paints, inks, and fragrances.
2. 3-Methoxy-3-methyl-1-butanol may be employed as raw material for the production of industrial detergents.

General Description

3-Methoxy-3-methyl-1-butanol is widely used as solvent for paints, inks, and fragrances. Kinetics of the reaction of 3-methoxy-3-methyl-1-butanol with OH radicals using a relative rate method has been reported. It has been identified as oxidation products of dyes such as methyl yellow, methyl red and methyl orange.

Flammability and Explosibility

Nonflammable

InChI:InChI=1/C6H14O2/c1-6(2,8-3)4-5-7/h7H,4-5H2,1-3H3

Synthetic route

4,4-dimethyl-1,3-dioxane (766-15-4) → solfit (56539-66-3)

Conditions	Yield
With diisobutylaluminium hydride In benzene for 2h; Heating;	90%

2-methyl-1-buten-4-ol (763-32-6) + methanol (67-56-1) → solfit (56539-66-3)

Conditions	Yield
With sodium iodide at 40 - 50℃; Green chemistry;	51%
With Na34[{MoVI6O21(H2O)6}12{(MoV2O4)30(OAc)22(H2O)16}] In water-d2 at 65℃; for 65h;

4,4-dimethyl-1,3-dioxane (766-15-4) + methanol (67-56-1) → solfit (56539-66-3)

Conditions	Yield
With sulfuric acid
With sulfuric acid at 40 - 90℃;

4,4-dimethyl-1,3-dioxane (766-15-4) → 3-methyl-butane-1,3-diol (2568-33-4) + solfit (56539-66-3)

Conditions	Yield
With porous sulfonic acid type strongly acidic ion exchange resin In methanol at 55℃; for 1h;

solfit (56539-66-3) + p-toluenesulfonyl chloride (98-59-9) → 3-methoxy-3-methylbutyl 4-methylbenzenesulfonate (869370-01-4)

Conditions	Yield
With dmap; triethylamine In dichloromethane at 20℃; for 16h;	95.5%
With pyridine at 0 - 20℃; for 16h; Inert atmosphere;	78%
With triethylamine In dichloromethane at 20℃; for 3h;	49%
With pyridine at 0 - 20℃;
With triethylamine In dichloromethane at 20℃; for 21h;

solfit (56539-66-3) + ethylaluminum dichloride (563-43-9) → [Cl2Al(OCH2CH2C(CH3)2OCH3)]2 (463966-53-2)

Conditions	Yield
In hexane (Ar); slow addn. of a soln. of alcohol in hexane to a soln. of aluminiumcompd. in hexane at 0°C, stirring for 0.5 h, slow warming to roo m temp.; evapn., drying in vac. crystn. (toluene, 5°C, 3 d); elem. anal.;	91%

trimethylaluminium dimer + solfit (56539-66-3) → [(CH3)2Al(μ-O-CH2CH2C(CH3)2-OCH3)]2

Conditions	Yield
In pentane byproducts: CH4; Ar-atmosphere; dropwise addn. of ligand to AlMe3 at -78°C, stirring for 2 h, then at room temp. for 12 h; solvent removal (vac.), dissoln. in PhMe, crystn. (-30°C); elem. anal.;	91%

solfit (56539-66-3) + p-toluenesulfonyl chloride (98-59-9) → methoxy-3-methylbutyl 4-methylbenzenesulfonate

Conditions	Yield
With dmap; triethylamine In dichloromethane at 20℃;	91%

solfit (56539-66-3) → 3-methoxy-3-methylbutanal (181134-54-3)

Conditions	Yield
Swern oxidation;	89%
With pyridine; oxalyl dichloride; dimethyl sulfoxide; triethylamine In dichloromethane at -78 - 4℃; for 1.25h; Swern oxidation;	89%
With oxalyl dichloride; dimethyl sulfoxide; triethylamine In dichloromethane at -60 - 20℃; Swern oxidation;	41%
Swern oxidation;
With Dess-Martin periodane In chloroform at 20℃; for 5h; Cooling with ice;

solfit (56539-66-3) + trimethyl gallium (1445-79-0) → [(CH3)2Ga(μ-O-CH2CH2C(CH3)2-OCH3)]2

Conditions	Yield
In pentane byproducts: CH4; Ar-atmosphere; dropwise addn. of ligand to GaMe3 at room temp., stirringovernight; distn. off of solvent, sublimation (74°C/0.1 mbar), then distn. (67°C/0.1 mbar) and crystn. on standing at -30°C for 1 h; elem. anal.;	89%

solfit (56539-66-3) + triethylsilyl formate (18296-01-0) → 3-methoxy-3-methyl-1-(triethylsiloxy)butane (80920-24-7)

Conditions	Yield
With [Ru(κ1-OAc)(κ2-OAc)(κ3-1,1,1-tris(diphenylphosphinomethyl)ethane)] In acetonitrile at 70℃; for 1h; Inert atmosphere; Schlenk technique;	88%
With tris(2-diphenylphosphinoethyl)phosphine; iron(II) acetate In dichloromethane Glovebox; Inert atmosphere; Heating;	87%

solfit (56539-66-3) + 1-chloro-4-(trifluoromethyl)-2-vinylbenzene → 1-chloro-2-(2-(3-methoxy-3-methylbutoxy)ethyl)-4-(trifluoromethyl)benzene

Conditions	Yield
With phosphazene base-P4-tert-butyl In hexane; m-xylene at 70℃; for 24h; Inert atmosphere;	82%

solfit (56539-66-3) + 2-trifluoromethylbenzenesulfonyl chloride (776-04-5) → 3-methoxy-3-methylbutyl 2-(trifluoromethyl)benzenesulfonate

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 4h;	81%

solfit (56539-66-3) + 2,6-dichlorostyrene (28469-92-3) → 1,3-dichloro-2-(2-(3-methoxy-3-methylbutoxy)ethyl)benzene

Conditions	Yield
With phosphazene base-P4-tert-butyl In hexane; m-xylene at 100℃; for 24h; Inert atmosphere;	81%

solfit (56539-66-3) + propionyl chloride (79-03-8) → 3-methoxy-3-methylbutyl propanoate (1080673-42-2)

Conditions	Yield
In tetrahydrofuran for 2.25h; Inert atmosphere;	80.1%

solfit (56539-66-3) + methyl chloroformate (79-22-1) → 3-methoxy-3-methylbutyl methoxyformate (1203544-43-7)

Conditions	Yield
With pyridine In tetrahydrofuran Inert atmosphere;	80%

solfit (56539-66-3) + 4-((6-chloro-1-ethyl-1H-pyrazolo[3,4-d]pyrimidin-4-yl)aminomethyl)benzenesulfonamide → 4-((1-ethyl-6-(3-methoxy-3-methylbutoxy)-1H-pyrazolo[3,4-d]pyrimidin-4-yl)aminomethyl)benzenesulfonamide

Conditions	Yield
Stage #1: solfit With potassium tert-butylate at 20℃; for 0.333333h; Stage #2: 4-((6-chloro-1-ethyl-1H-pyrazolo[3,4-d]pyrimidin-4-yl)aminomethyl)benzenesulfonamide at 70℃; for 10h;	76%

oxalyl dichloride (79-37-8) + solfit (56539-66-3) → bis(3-methoxy-3-methylbutylethane)-1,2-dioate (1203544-56-2)

Conditions	Yield
In dichloromethane at 0℃;	73.3%

solfit (56539-66-3) + 3-methoxy-3-methylbutyl 4-methylbenzenesulfonate (869370-01-4) → 1-methoxy-3-(3-methoxy-3-methylbutoxy)-1,1-dimethylpropane (1203544-39-1)

Conditions	Yield
Stage #1: solfit With sodium hydride In tetrahydrofuran at 40 - 70℃; Inert atmosphere; Stage #2: 3-methoxy-3-methylbutyl 4-methylbenzenesulfonate In tetrahydrofuran	71.7%

solfit (56539-66-3) + 3-oxapentanoic acid (627-03-2) → 3-methoxy-3-methylbutyl 2-ethoxyacetate (1203544-47-1)

Conditions	Yield
With toluene-4-sulfonic acid at 40℃; for 5h;	71.2%

solfit (56539-66-3) + 3-chloro-isonicotinonitrile (68325-15-5) → 3-(3-methoxy-3-methylbutoxy)pyridine-4-carbonitrile

Conditions	Yield
Stage #1: solfit With sodium hydride In tetrahydrofuran; mineral oil at 0 - 20℃; for 1h; Inert atmosphere; Stage #2: 3-chloro-isonicotinonitrile In tetrahydrofuran; mineral oil at 20℃; Inert atmosphere;	67%
Stage #1: solfit With sodium hydride In tetrahydrofuran at 0 - 20℃; for 0.65h; Stage #2: 3-chloro-isonicotinonitrile In tetrahydrofuran at 20℃;	67%

1-bromo-2,2-dimethoxyethane (7252-83-7) + solfit (56539-66-3) → 3-(2,2-dimethoxyethoxy)-1-methoxy-1,1-dimethylpropane (1203544-32-4)

Conditions	Yield
Stage #1: solfit With sodium hydride In tetrahydrofuran at 40 - 70℃; Inert atmosphere; Stage #2: 1-bromo-2,2-dimethoxyethane In tetrahydrofuran at 70℃; for 16.5h; Inert atmosphere;	65.5%

carbon disulfide (75-15-0) + solfit (56539-66-3) → potassium 3-methoxy-3-methyl-1-butylxanthate

Conditions	Yield
Stage #1: solfit With potassium hydroxide at 20℃; for 2h; Stage #2: carbon disulfide	62.8%

solfit (56539-66-3) + 2-methoxyacetic acid (625-45-6) → 3-methoxy-3-methylbutyl 2-methoxyacetate (1203544-46-0)

Conditions	Yield
Stage #1: 2-methoxyacetic acid With oxalyl dichloride In dichloromethane; N,N-dimethyl-formamide at 20 - 40℃; Stage #2: solfit With pyridine In dichloromethane; N,N-dimethyl-formamide at 0℃; Inert atmosphere;	61.1%

solfit (56539-66-3) + 3-Chloro-2-methylpropene (563-47-3) → 1-methoxy-1,1-dimethyl-3-(2-methylprop-2-enyloxy)propane (1093653-61-2)

Conditions	Yield
With sodium hydroxide; tetra(n-butyl)ammonium hydroxide In water at 70℃; for 10h;	61%

solfit (56539-66-3) + 2-methyl-8-(6-(naphthalen-1-yl)pyridin-2-yl)-1,2,3,4-tetrahydroquinoline + hafnium tetrachloride (13499-05-3) → C27H26HfN2

Conditions	Yield
In toluene at 20℃; for 4h; Glovebox; Cooling with ice;	57.1%

formic acid (64-18-6) + solfit (56539-66-3) → 3-methoxy-3-methylbutyl formate (1203544-40-4)

Conditions	Yield
at 20℃; for 6h;	56.3%

solfit (56539-66-3) + acrolein (107-02-8) → 3-(3-methoxy-3-methylbutoxy)propanal (1203544-54-0)

Conditions	Yield
With hydrogenchloride In water at 40℃; for 72h; Subdued light;	55.9%

solfit (56539-66-3) + pentafluorobenzenesulonyl chloride (832-53-1) → 3-methoxy-3-methylbutyl 2,3,4,5,6-pentafluorobenzenesulfonate

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 2h;	51%

solfit (56539-66-3) → N-[5-chloro-2-(3-methoxy-3-methylbutoxy)phenyl]-N'-(5-cyano-2-pyrazinyl)urea (660851-16-1)

Conditions	Yield
	46%

solfit (56539-66-3) + N-{(3E)-5-tert-butyl-1-methyl-2-[(2R)-tetrahydrofuran-2-ylmethyl]-1,2-dihydro-3H-pyrazol-3-ylidene}-2-fluoro-5-(trifluoromethyl)benzamide (1140917-51-6) → N-{(3E)-5-tert-butyl-1-methyl-2-[(2R)-tetrahydrofuran-2-ylmethyl]-1,2-dihydro-3H-pyrazol-3-ylidene}-2-(3-methoxy-3-methylbutoxy)-5-(trifluoromethyl)benzamide (1140917-56-1)

Conditions	Yield
Stage #1: solfit With potassium tert-butylate In tetrahydrofuran for 0.166667h; Stage #2: N-{(3E)-5-tert-butyl-1-methyl-2-[(2R)-tetrahydrofuran-2-ylmethyl]-1,2-dihydro-3H-pyrazol-3-ylidene}-2-fluoro-5-(trifluoromethyl)benzamide In tetrahydrofuran for 3h;	41%
Stage #1: solfit With potassium tert-butylate In tetrahydrofuran for 0.166667h; Stage #2: N-{(3E)-5-tert-butyl-1-methyl-2-[(2R)-tetrahydrofuran-2-ylmethyl]-1,2-dihydro-3H-pyrazol-3-ylidene}-2-fluoro-5-(trifluoromethyl)benzamide In tetrahydrofuran for 3h;	41%

Upstream product

• 766-15-4 4,4-dimethyl-1,3-dioxane 
• 763-32-6 2-methyl-1-buten-4-ol 
• 67-56-1 methanol 

Downstream Products

• 72326-18-2 (E)-4-[4-(4-Trifluoromethyl-phenoxy)-phenoxy]-pent-2-enoic acid 3-methoxy-3-methyl-butyl ester 
• 1268153-93-0 3-methoxy-3-methylbutan-1-amine 
• 1570496-03-5 5-(1-{[3-(3-methoxy-3-methylbutoxy)phenyl]methyl}-5-methyl-1H-1,2,4-triazol-3-yl)-3-[4-(trifluoromethoxy)phenyl]-1,2,4-oxadiazole 
• 1246921-13-0 8-Fluoro-3-[2-fluoro-3-(trifluoromethyl)phenyl]-1-(3-methoxy-3-methylbutyl)cinnolin-4(1H)-one 
• 869370-01-4 3-methoxy-3-methylbutyl 4-methylbenzenesulfonate 
• 1140917-56-1 N-{(3E)-5-tert-butyl-1-methyl-2-[(2R)-tetrahydrofuran-2-ylmethyl]-1,2-dihydro-3H-pyrazol-3-ylidene}-2-(3-methoxy-3-methylbutoxy)-5-(trifluoromethyl)benzamide 
• 660851-16-1 N-[5-chloro-2-(3-methoxy-3-methylbutoxy)phenyl]-N'-(5-cyano-2-pyrazinyl)urea 
• 282735-71-1 (2'S,3S,4'R,5'R)-1,2-dihydro-2'-(2-methoxy-2-methylpropyl)-2-oxo-5'-[[(2R)-2-[(phenylmethoxy)carbonyl]-1-pyrrolidinyl]carbonyl]spiro[3H-indole-3,3'-pyrrolidine]-4'-carboxylic acid ethyl ester 
• 282735-67-5 (3S,3'S,4'R,6'S,8'R,8'aR)-1,2,3',4',8',8a'-hexahydro-6'-(2-methoxy-2-methylpropyl)-1',2-dioxo-3',4'-diphenylspiro[3H-indole-3,7'(6'H)-[1H]pyrrolo[2,1-c][1,4]oxazine]-8'-carboxylic acid ethyl ester 
• 282735-80-2 (2'R,3R,4'S,5'S)-1,2-dihydro-2'-(2-methoxy-2-methylpropyl)-2-oxo-5'-[[(2R)-2-[(phenylmethoxy)carbonyl]-1-pyrrolidinyl]carbonyl]spiro[3H-indole-3,3'-pyrrolidine]-4'-carboxylic acid ethyl ester 
• 282735-75-5 (2'R,3R,4'S,5'S)-1,2-dihydro-2'-(2-methoxy-2-methylpropyl)-2-oxo-5'-[[(2S)-2-[(phenylmethoxy)carbonyl]-1-pyrrolidinyl]carbonyl]spiro[3H-indole-3,3'-pyrrolidine]-4'-carboxylic acid ethyl ester 
• 282735-73-3 (3R,3'R,4'S,6'R,8'S,8'aS)-1,2,3',4',8',8a'-hexahydro-6'-(2-methoxy-2-methylpropyl)-1',2-dioxo-3',4'-diphenylspiro[3H-indole-3,7'(6'H)-[1H]pyrrolo[2,1-c][1,4]oxazine]-8'-carboxylic acid ethyl ester 

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