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
• Article Data: 17

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

4-Methoxy-1-butanol is used as a chemicals, pharmaceutical intermediates, reagents. 4-Methoxy-1-butanol is used with n-butyl acetate to improve dissolving power, drying time, and flow.

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 
• 110-63-4 Butane-1,4-diol 
• 74-88-4 methyl iodide 
• 77-78-1 dimethyl sulfate 
• 98-01-1 furfural 
• 67-56-1 methanol 
• 29006-01-7 Methyl 4-methoxybutyrate 
• 762-72-1 allyl-trimethyl-silane 
• 74-87-3 methylene chloride 
• 50-00-0 formaldehyd 
• 928-51-8 4-Chloro-1-butanol 
• 124-41-4 sodium methylate 
• 4696-30-4 methoxy-1 butene-3 
• 505-65-7 1,3-dioxepane 

Downstream Products

• 4457-67-4 4-Methoxy-1-bromobutane 
• 21071-24-9 4-methoxybutanal 
• 36865-47-1 1-Ethoxy-4-methoxybutan 
• 16654-44-7 4-Methoxy-butyl-trimethylsilylaether 
• 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 
• 1422064-31-0 methyl 1-[4-(4-methoxybutoxy)benzyl]-5-oxo-L-prolinate 
• 1422064-25-2 [4-(4-methoxybutoxy)phenyl]methanol 

Relevant articles and documents

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

The invention provides a compound which is a diazine of formula (I) or a tautomer thereof, or a pharmaceutically acceptable salt thereof, for use as an antifungal agent: (I) wherein X, N', C', A and E are as defined herein. The invention also provides a compound of Formula (I) as defined herein.

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.

Synthesis of the marine compound (2R,5Z,9Z)-2-methoxyhexacosa-5,9-dienoic acid via a lipase-catalyzed resolution and a novel O-alkylation protocol

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.