111-32-0

Basic information

• Product Name: 4-Methoxy-1-butanol
• Synonyms: 4-methoxy-1-butano;4-Methoxybutanol;4-methoxybutylalcohol;Butylene glycol methyl ether;butyleneglycolmethylether;Dowanol bm;Dowanol BMAT;1,4-BUTANEDIOL MONOMETHYL ETHER
• CAS NO: 111-32-0
• Molecular Formula: C₅H₁₂O₂
• Molecular Weight: 104.15
• EINECS: 203-858-6
• Mol File: 111-32-0.mol

Chemical Properties

• Boiling Point: 66 °C / 7mmHg
• Flash Point: 73°(163°F)
• Appearance: /
• Density: 0.93
• Vapor Pressure: 0.618mmHg at 25°C
• Refractive Index: 1.4190-1.4330
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 15.08±0.10(Predicted)
• Water Solubility: Slightly soluble in water.
• CAS DataBase Reference: 4-Methoxy-1-butanol(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Methoxy-1-butanol(111-32-0)
• EPA Substance Registry System: 4-Methoxy-1-butanol(111-32-0)

Safety Data

• Hazard Codes: F
• Statements: 36/37/38-10
• Safety Statements: 26-36/37/39-35-3/9/49-15
• RIDADR: UN1993
• RTECS: EL4550000
• HazardClass: 3
• PackingGroup: III
• Hazardous Substances Data: 111-32-0(Hazardous Substances Data)

Usage

Uses

Used in Chemical Industry:
4-Methoxy-1-butanol is used as a chemical intermediate for the synthesis of various specialty chemicals, including fragrances, flavors, and other organic compounds. Its ability to form esters and ethers makes it a versatile building block in the chemical industry.
Used in Pharmaceutical Industry:
In the pharmaceutical sector, 4-Methoxy-1-butanol serves as an intermediate in the production of certain drugs and active pharmaceutical ingredients. Its reactivity and solubility properties facilitate its use in the synthesis of complex molecular structures.
Used as a Solvent:
4-Methoxy-1-butanol is used as a solvent in various applications due to its ability to dissolve a wide range of substances. It is particularly useful in the paint and coatings industry, where it helps improve the solubility of resins and other components, leading to better film formation and enhanced performance.
Used with n-Butyl Acetate:
When combined with n-butyl acetate, 4-Methoxy-1-butanol enhances the dissolving power, drying time, and flow properties of the resulting mixture. This combination is beneficial in applications such as the formulation of coatings, inks, and adhesives, where improved performance and processing characteristics are desired.

InChI:InChI=1/C5H12O2/c1-7-5-3-2-4-6/h6H,2-5H2,1H3

Synthetic route

Butane-1,4-diol (110-63-4) + methyl iodide (74-88-4) → 4-methoxybutanol (111-32-0)

Conditions	Yield
With mercury(II) oxide In dichloromethane at 20℃; for 28h;	78%
(i) TlOEt, benzene, (ii) /BRN= 969135/, MeCN; Multistep reaction;
With thallium (I) ethoxide 1) MeCN, r.t., 2) MeCN, 20 deg C, 14 h; Yield given. Multistep reaction;

O-methyltetrahydrofuranium perchlorate → tetrahydrofuran (109-99-9) + methanol (67-56-1) + 4-methoxybutanol (111-32-0)

Conditions	Yield
With perchloric acid; sodium perchlorate; water at 25℃;	A n/a B n/a C 98%

diazomethane (186581-53-3, 908094-01-9) → methanol (67-56-1) + 4-methoxybutanol (111-32-0)

Conditions	Yield
With perchloric acid; sodium perchlorate; water In tetrahydrofuran at 25℃; Product distribution; Kinetics; Rate constant; pH 4.0; reaction with different pH;	A 88% B 12%

1,3-dioxepane (505-65-7) → 4-methoxybutanol (111-32-0)

Conditions	Yield
With diisobutylaluminium hydride In benzene for 2h; Heating;	90%
With lithium aluminium tetrahydride; boron trichloride 1.) CH2Cl2, 0.2 h, 2.) Et2O, 30 min; Yield given. Multistep reaction;

Methyl 4-methoxybutyrate (29006-01-7) + allyl-trimethyl-silane (762-72-1) → 4-methoxybutanol (111-32-0) + 7-methoxy-1-hepten-4-ol (1238320-08-5)

Conditions	Yield
With indium (III) iodide; Dimethylphenylsilane In dichloromethane at 20℃; for 3h; Inert atmosphere; chemoselective reaction;	A 11 %Spectr. B 50%

Butane-1,4-diol (110-63-4) + dimethyl sulfate (77-78-1) → 4-methoxybutanol (111-32-0)

Conditions	Yield
With sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate In hexane; water for 6h;	80%

2-nitroso-3,6-dihydro-2H-[1,2]oxazine (3276-41-3) → 4-methoxybutanol (111-32-0)

Conditions	Yield
With hydrogen; nickel In methanol

furfural (98-01-1) + methanol (67-56-1) → Tetrahydrofurfuryl alcohol (97-99-4) + methyl tetrahydrofurfuryl ether (19354-27-9) + 1,5-dimethoxypentane (111-89-7) + 4-methoxybutanol (111-32-0) + O-methyl-pentamethylene glycol (4799-62-6) + 2-(methoxymethyl)furan (13679-46-4)

Conditions	Yield
With palladium on activated charcoal; hydrogen at 170℃; under 52505.3 Torr; for 2h; Autoclave;	A 44.3% B 8.4% C n/a D n/a E n/a F n/a

4-Chloro-1-butanol (928-51-8) + sodium methylate (124-41-4) → 4-methoxybutanol (111-32-0)

Conditions	Yield
In methanol Heating;	82%

cis,trans-2,5-dimethoxytetrahydrofuran (696-59-3) → 4-methoxybutanol (111-32-0)

Conditions	Yield
With lithium aluminium tetrahydride; aluminium trichloride In tetrahydrofuran

methylene chloride (74-87-3) + C4H9O2(1-) → 4-methoxybutanol (111-32-0)

Conditions	Yield
at 76.84℃; under 3E-07 - 5E-06 Torr; Kinetics;

formaldehyd (50-00-0) + magnesium compound of 3-chloro-1-methoxy-propane → 4-methoxybutanol (111-32-0)

Conditions	Yield
With diethyl ether; zinc(II) chloride
With benzene

3-bromo-2-methoxy-tetrahydrofuran (33691-61-1) → 4-methoxybutanol (111-32-0)

Conditions	Yield
With lithium aluminium tetrahydride; aluminium trichloride for 10h;

methyl iodide (74-88-4) + sodium-<4-hydroxy-butylate> → 4-methoxybutanol (111-32-0)

Conditions	Yield
With Butane-1,4-diol; toluene

methoxy-1 butene-3 (4696-30-4) → propylene glycol methyl ether (41223-27-2) + 4-methoxybutanol (111-32-0)

Conditions	Yield
With sodium hydroxide; sodium tetrahydroborate; mercury(II) diacetate In tetrahydrofuran; water Product distribution; 1) 30 min, 2) ca. 0.5 h;
With sodium hydroxide; sodium tetrahydroborate; mercury(II) diacetate 1) 30 min, 2) aq. NaOH, NaBH4; Yield given. Multistep reaction. Yields of byproduct given;

potassium 4-hydroxy-1-butoxide + methyl iodide (74-88-4) → 4-methoxybutanol (111-32-0)

Upstream product

• 696-59-3 cis,trans-2,5-dimethoxytetrahydrofuran 
• 3276-41-3 2-nitroso-3,6-dihydro-2H-[1,2]oxazine 
• 33691-61-1 3-bromo-2-methoxy-tetrahydrofuran 
• 110-63-4 Butane-1,4-diol 
• 74-88-4 methyl iodide 
• 186581-53-3 diazomethane 
• 505-65-7 1,3-dioxepane 
• 4696-30-4 methoxy-1 butene-3 
• 928-51-8 4-Chloro-1-butanol 
• 124-41-4 sodium methylate 
• 50-00-0 formaldehyd 
• 98-01-1 furfural 
• 67-56-1 methanol 
• 29006-01-7 Methyl 4-methoxybutyrate 

Downstream Products

• 17913-18-7 4-(methoxy)-1-chlorobutane 
• 16654-44-7 4-Methoxy-butyl-trimethylsilylaether 
• 4457-67-4 4-Methoxy-1-bromobutane 
• 21071-24-9 4-methoxybutanal 
• 1143-02-8 4-bromo-benzenesulfonic acid-(4-methoxy-butyl ester) 
• 29006-02-8 4-methoxybutyric acid 
• 1447726-31-9 2-(3,5-bis-(4-fluoro-phenyl)-(1,2,4)triazol-1-yl)-1-(4-(6-(4-methoxy-butoxy)-pyrimidin-4-yl)-piperazin-1-yl)-ethanone 
• 1355077-31-4 4-methoxybutyl 4-nitrophenyl carbonate 
• 1422064-37-6 benzyl 1-[4-(4-methoxybutoxy)benzyl]-5-oxo-L-prolyl-3-trityl-L-histidinate 
• 1422064-34-3 1-[4-(4-methoxybutoxy)benzyl]-5-oxo-L-proline 
• 1422064-40-1 1-[4-(4-methoxybutoxy)benzyl]-5-oxo-L-prolyl-L-histidine 
• 1422064-26-3 1-(bromomethyl)-4-(4-methoxybutoxy)benzene 

Relevant articles and documents

Effect of Ether Oxygen in Isomeric Alcohols on Water Structure Estimated from Ultrasonic Absorption and Velocity Data

4-Methoxy-1-butanol was synthesized form 1,4-butanediol through potassium 4-hydroxy-1-butoxide.The ultrasonic absorption coefficients in the frequency range from 9.5 to 220 MHz and the sound velocity at 2.5 and 1.92 MHz were measured in aqueous solutions as a function of the concentration.A single relaxational absorption was observed, the cause of which was attributed to the perturbation of an equlibrium associated with a solute-solvent interaction.The rate and thermodynamic parameters associated with the interacion were determined from the concentration dependence of the relaxation frequency.The results were compared with those for other isomeric alcohol solutions, and the effect of the alcohols on the water structure was considered in relation to the molecular structures of the solutes.It has been found that the position of the ether oxygen in the alcohol molecules gives rise to a considerable change in the solution properties.

2-AMINO-1,3,4-THIADIAZINE AND 2-AMINO-1,3,4-OXADIAZINE BASED ANTIFUNGAL AGENTS

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Upgrading biomass-derived furans via acid-catalysis/hydrogenation: The remarkable difference between water and methanol as the solvent

In methanol 5-hydroxymethylfurfural (HMF) and furfuryl alcohol (FA) can be selectively converted into methyl levulinate via acidcatalysis, whereas in water polymerization dominates. The hydrogenation of HMF, furan and furfural with the exception of FA is

Indium triiodide catalyzed direct hydroallylation of esters

The InI3-catalyzed hydroallylation of esters by using hydroand allysilanes under mild conditions has been accomplished. Many significant groups such as alkenyl, alkynyl, cyano, and nitro ones survive under these conditions. This reaction system, provided routes to both homoallylic alcohols and ethers, in which either elimination of the alkoxy moiety or of the carbonyl oxygen atom could be freely selected by changing the substituents on the alkoxy moiety and on the hydrosilane. In addition, the hydroallylation of lactones took place without ring cleavage to produce the desired cyclic ethers in high yields.

Hydrogen bonding lowers intrinsic nucleophilicity of solvated nucleophiles

The relationship between nucleophilicity and the structure/environment of the nucleophile is of fundamental importance in organic chemistry. In this work, we have measured nucleophilicities of a series of substituted alkoxides in the gas phase. The functional group substitutions affect the nucleophiles through ion-dipole, ion-induced dipole interactions and through hydrogen bonding whenever structurally possible. This set of alkoxides serves as an ideal model system for studying nucleophiles under microsolvation settings. Marcus theory was applied to analyze the results. Using Marcus theory, we separate nucleophilicity into two independent components, an intrinsic nucleophilicity and a thermodynamic driving force determined solely by the overall reaction exothermicity. It is found that the apparent nucleophilicities of the substituted alkoxides are always much lower than those of the unsubstituted ones. However, ion-dipole, ion-induced dipole interactions, by themselves, do not significantly affect the intrinsic nucleophilicity; the decrease in the apparent nucleophilicity results from a weaker thermodynamic driving force. On the other hand, hydrogen bonding not only stabilizes the nucleophile but also increases the intrinsic barrier height by 3 to ～4 kcal mol-1. In this regard, the hydrogen bond is not acting as a perturbation in the sense of an external dipole but more directly affects the electronic structure and reactivity of the nucleophilic alkoxide. This finding offers a deeper insight into the solvation effect on nucleophilicity, such as the remarkably lower reactivities in nucleophilic substitution reactions in protic solvents than in aprotic solvents.

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The title compound has been synthesized by a facile route starting from 4-pentyn-1-ol. The enantioselectivity was attained by a strategy involving a lipase-catalyzed acetylation of a solid-phase immobilized long chain α-hydroxy acid. Another important feature of the synthesis was the formulation of an efficient HgO-catalyzed O-methylation of the α-hydroxy acids which proceeded without any racemization. The alkylation protocol was also highly efficient for selective mono-methylation/benzylation of symmetrical diols.

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The 13C labeled 1-decanols at positions 1, 5 and 9 have been synthesized their dynamics in (CD3O-CD2CD2)2O, CD3CD2OD, and CD2Cl2 solvents have been studied by 13C-coupled relaxation methods. The expriments were performed oin the temperature range of 245-298 K. The data were fitted using the Redfield theory of nuclear relaxation to yield dipolar spectral densities to which transformed into Cartesian correlation times. The Cartesian correlation times obtained experimentally have a strong bearing on local anisotropic motion and suggest that the size of groups attached to a given carbon and also hydrogen bonding between 1-decanol and the various solvant moleculars have a profund effect on local segmenat motion. The hydrogn bond anchoring effect is apparently strongest near the hydrogen bonding site. The effect of solvant viscoleastic response, hydrogen bonding, and torsional forcs on the motion of Cartesian modes at different locations and end-to-end vectors in l-decanol are analyzed using both generalized (GLE) and ordinary Langevin equations (OLE) simulations. The asymmetry of Cartesian correlation as one moves away from the cahin center aries from the in the torsional potentials of the C-C-C-OH and C-C-C-C linkages at each end from a hydrogen bond anchoring effect at the first (C1). The stronger retardation effect at C1 observed in ethanol is found fom the GLE simulations to be mainly attributable to a large spatial blockage of the motion of the beads near-OH. For a by solute molcules with surrounded by solvent molecules with internal rotation, its motion is closely correlated with the solvent relaxation rate giving significantly reduced friction forces. Conversely, the local Cartesian relaxation for I-decanol in methylene choloride fails to correlate effectively with solvent relaxation and can be described satusfactorily by OLEs with δ-memory kernel. The contributions from overall tumbling and internal motion to the relaxation of local Cartesian modes and to the end-to-end vectors are analyzed by using calculated apparent activation energies.

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