2517-43-3

Basic information

• Product Name: 3-Methoxy-1-butanol
• Synonyms: 3-METHOXY-1-BUTANOL;1-Butanol,3-methoxy-;3-methoxy-1-butano;3-Methoxybutanol;Methoxybutanol;3-methoxybutan-1-ol;1,3-butyleneglycol monomethyl ether;3-METHOXY-N-BUTANOL
• CAS NO: 2517-43-3
• Molecular Formula: C₅H₁₂O₂
• Molecular Weight: 104.15
• EINECS: 219-741-8
• Product Categories: Alcohols;C2 to C6;Oxygen Compounds
• Mol File: 2517-43-3.mol
• Article Data: 3

Chemical Properties

• Melting Point: -85 °C
• Boiling Point: 161 °C
• Flash Point: 116 °F
• Appearance: Clear colorless/Liquid
• Density: 0.928 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.738mmHg at 25°C
• Refractive Index: n20/D 1.416(lit.)
• Storage Temp.: Flammables area
• PKA: 14.90±0.10(Predicted)
• Water Solubility: SOLUBLE
• CAS DataBase Reference: 3-Methoxy-1-butanol(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Methoxy-1-butanol(2517-43-3)
• EPA Substance Registry System: 3-Methoxy-1-butanol(2517-43-3)

Safety Data

• Statements: 10
• Safety Statements: 16
• RIDADR: UN 1987 3/PG 3
• WGK Germany: 1
• HazardClass: 3.2
• PackingGroup: III
• Hazardous Substances Data: 2517-43-3(Hazardous Substances Data)

Usage

Chemical Properties

CLEAR COLOURLESS LIQUID

Uses

Different sources of media describe the Uses of 2517-43-3 differently. You can refer to the following data:
1. High-boiling lacquer solvent, coupling agent for brake fluids, intermediate for plasticizers, herbicides, film-forming additive in PVA emulsions, solvent for pharmaceuticals.
2. 3-Methoxy-1-butanol can be used as: A solvent in the synthesis of potassium 3-methoxy-1-butylxanthate, an intermediate used in the preparation of xanthate complexes. A model compound in the study of dehydration of alcohols using CeO2?as a catalyst. An intermediate to synthesize perylene diimide-based dyes applicable as the colorant of the black matrix.

Hazard

Toxic by ingestion.

InChI:InChI=1/C5H12O2/c1-5(7-2)3-4-6/h5-6H,3-4H2,1-2H3/t5-/m1/s1

Synthetic route

1-acetoxy-3-(chloromethoxy)butane (93185-29-6) → 3-methoxy butanol (2517-43-3)

Conditions	Yield
With lithium aluminium tetrahydride In diethyl ether for 2h; Ambient temperature;	80%

3-methoxybutanal (5281-76-5) → 3-methoxy butanol (2517-43-3)

Conditions	Yield
With nickel; copper at 150 - 180℃; Hydrogenation;
With methanol; nickel pumice stone at 90 - 100℃; under 18387.7 Torr; Hydrogenation;
With nickel at 150 - 180℃; Hydrogenation;

(+-)-3-methoxy-butyric acid methyl ester → 3-methoxy butanol (2517-43-3)

Conditions	Yield
With lithium aluminium tetrahydride; diethyl ether

4-methyl-1,3-dioxane (1120-97-4) → 3-methoxy butanol (2517-43-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: 86 percent / ZnCl2 / pentane / 1 h 2: 80 percent / LiAlH4 / diethyl ether / 2 h / Ambient temperature View Scheme

2-Methoxypropene (116-11-0) + carbon monoxide (201230-82-2) → 3-methoxy butanol (2517-43-3)

Conditions	Yield
With dicobalt octacarbonyl; triisobutylphosphane; hydrogen; zinc dibromide In tert-butyl methyl ether at 150℃; under 7500.75 - 97509.8 Torr; for 4h; Solvent; Reagent/catalyst; Temperature; Glovebox; Autoclave;

methanol (67-56-1) + methyloxirane (75-56-9, 16033-71-9) → 3-methoxy butanol (2517-43-3) + propylene glycol methyl ether (41223-27-2)

Conditions	Yield
With silica-P123-templated Ce doped Mg/Al-double oxide at 120℃; for 8h; Reagent/catalyst; Temperature; Concentration;

3-methoxy butanol (2517-43-3) + recorcinol (108-46-3) → 4-hydroxysalicylic acid (89-86-1)

Conditions	Yield
With hydrogenchloride; sodium hydroxide; CO2 In water	95.4%
With CO2; potassium carbonate In water	87.4%

3-methoxy butanol (2517-43-3) → (+)-3-methoxy-1-butanol

Conditions	Yield
With phosphate buffer; propanoic acid methyl ester for 20h; Ambient temperature;	93%

3-methoxy butanol (2517-43-3) + cyanoacetic acid (372-09-8) → 3-methoxybutyl 2-cyanoacetate

Conditions	Yield
Stage #1: cyanoacetic acid With trifluoroacetic anhydride In acetonitrile at 22℃; for 3h; Inert atmosphere; Stage #2: 3-methoxy butanol In acetonitrile at 22℃; for 3h;	91%
toluene-4-sulfonic acid In toluene Reflux;

3-methoxy butanol (2517-43-3) + propanoic acid methyl ester (554-12-1) → (-)-3-methoxy-1-butyl propionate

Conditions	Yield
With phosphate buffer for 20h; Ambient temperature; hog liver carboxylesterase catalyzed transesterification;	88%

3-methoxy butanol (2517-43-3) + methanesulfonyl chloride (124-63-0) → 3-Methoxybutyl methanesulfonate (428870-98-8)

Conditions	Yield
With triethylamine In ethyl acetate at 2 - 20℃; for 3.5h;	88%
With triethylamine In dichloromethane at 20℃; for 0.5h; Cooling with ice bath;

3-methoxy butanol (2517-43-3) + ethylaluminum dichloride (563-43-9) → 0.76[Cl2Al(OCH2CH2CHCH3OCH3)]2*0.24[Cl2Al(OCH2CH2CHCH3OCH3)]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; evapn., drying in vac., crystn. (C6H6, 10°C, 1 wk); elem. anal.;	87%

3-methoxy butanol (2517-43-3) + ethyl 2-diazo-3-(hydroxy(methyl)amino)-3-oxopropanoate (1441119-58-9) → ethyl 2-diazo-3-[(3-methoxybutoxy)(methyl)amino]-3-oxopropanoate

Conditions	Yield
With di-tert-butyl-diazodicarboxylate; triphenylphosphine In dichloromethane at 20℃; for 25h; Mitsunobu Displacement; Inert atmosphere;	86%

3-methoxy butanol (2517-43-3) + dichloro{bis[2-(diphenylphosphino)ethyl]amine}ruthenium(II) dimer → [carbonylchlorohydrido{bis[2-(diphenylphosphinomethyl)ethyl]amino}ethylamino] ruthenium(II) (1295649-40-9)

Conditions	Yield
With sodium methylate for 1h; Reagent/catalyst; Inert atmosphere; Reflux;	84.6%

but-3-enoic acid (625-38-7) + 3-methoxy butanol (2517-43-3) → 3-methoxy-1-butyl-3-butenoate

Conditions	Yield
With toluene-4-sulfonic acid In toluene at 130℃; for 4h; Dean-Stark; Inert atmosphere;	80%

3-methoxy butanol (2517-43-3) + 1-(bromomethyl)-4-(1,1-dimethylethyl)benzene (18880-00-7) → 4-tert-Butylbenzyl alcohol (877-65-6) + bis(4-tert-butyl)benzyl ether (56428-01-4) + 4-tert-butylbenzyl 3-methoxybutyl ether

Conditions	Yield
With sodium hydroxide; 5,11,17,23-tetramethoxy-25,26,27,28-tetrakis(trimethylammoniomethyl)calix<4>arene tetrachloride at 60℃; for 3h;	A 6% B 4% C 78%

3-methoxy butanol (2517-43-3) + carbon monoxide (201230-82-2) + hex-1-yne (693-02-7) → C12H22O3

Conditions	Yield
With methanesulfonic acid; C29H33N2P; palladium dichloride In acetonitrile Glovebox; Sealed tube; Inert atmosphere; Autoclave; regioselective reaction;	78%

[ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2 (52462-29-0) + 3-methoxy butanol (2517-43-3) + bis(2-(dicyclohexylphosphanyl)ethyl)amine (550373-32-5) → carbonyl chlorohydride{bis[2-(dicyclohexylphosphino)ethyl]amine}ruthenium(II) (1421060-11-8)

Conditions	Yield
Stage #1: [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; 3-methoxy butanol; bis[2-(dicyclohexylphosphanyl)ethyl]amine for 1h; Inert atmosphere; Reflux; Stage #2: With sodium ethanolate for 1h; Inert atmosphere; Reflux;	77.8%

3-methoxy butanol (2517-43-3) + cyclohexane (110-82-7) + carbon monoxide (201230-82-2) → C12H22O3

Conditions	Yield
With 1,10-Phenanthroline; di-tert-butyl peroxide; copper dichloride at 120℃; under 15001.5 Torr; for 24h; Autoclave; Inert atmosphere;	77%

[ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2 (52462-29-0) + 3-methoxy butanol (2517-43-3) + bis(2-(diphenylphosphino)ethyl)amine hydrochloride (66534-97-2) → [carbonylchlorohydrido{bis[2-(diphenylphosphinomethyl)ethyl]amino}ethylamino] ruthenium(II) (1295649-40-9)

Conditions	Yield
Stage #1: 3-methoxy butanol; bis(2-(diphenylphosphino)ethyl)amine hydrochloride With sodium methylate at 20℃; for 0.5h; Inert atmosphere; Stage #2: [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2 for 1h; Reagent/catalyst; Reflux; Inert atmosphere;	76.6%

3-methoxy butanol (2517-43-3) + 4-amino-5-chloro-N-[2-(diethylamino)ethyl]-2-hydroxybenzamide (38339-95-6) → 4-Amino-5-chloro-N-[2-(diethylamino)ethyl]-2-(3-methoxybut-1-yl)oxybenzamid (114614-51-6)

Conditions	Yield
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran	76%

3-methoxy butanol (2517-43-3) → 3-methoxybutanal (5281-76-5)

Conditions	Yield
With Dess-Martin periodane In dichloromethane at 20℃; for 0.5h; Inert atmosphere;	71%
With perchloric acid; N-bromoacetamide In water; acetic acid at 303℃; Thermodynamic data; Kinetics; Rate constant; other temperatures; ΔH(excit.), ΔS(excit.), ΔF(excit.);
With pyridinium chlorochromate In dimethyl sulfoxide for 6h; Kinetics; Mechanism; Thermodynamic data; Εa, log A, ΔS(excit.), ΔG(excit.);

carbon disulfide (75-15-0) + 3-methoxy butanol (2517-43-3) → potassium 3-methoxy-1-butylxanthate

Conditions	Yield
Stage #1: 3-methoxy butanol With potassium hydroxide at 20℃; for 2h; Stage #2: carbon disulfide	70.3%

3-methoxy butanol (2517-43-3) + n-octyne (629-05-0) + carbon monoxide (201230-82-2) → C14H26O3

Conditions	Yield
With methanesulfonic acid; C29H33N2P; palladium dichloride In acetonitrile Glovebox; Sealed tube; Inert atmosphere; Autoclave; regioselective reaction;	70%

(RS)-2-phenylcyclohexanone (1444-65-1) + 3-methoxy butanol (2517-43-3) → 3-methoxybutyl 6-oxo-6-phenylhexanoate

Conditions	Yield
With sulfuric acid; aurin; oxygen In toluene at 20℃; for 24h; Schlenk technique; Irradiation;	63%

indole (120-72-9) + 3-methoxy butanol (2517-43-3) + hexaketocyclohexane (527-31-1) → 3-methoxybutyl 2-(1H-indol-3-yl)-2-oxoacetate

Conditions	Yield
With 1,10-Phenanthroline; copper(I) bromide dimethylsulfide complex; silver carbonate; trifluoroacetic acid In acetonitrile at 80℃; for 20h; Sealed tube;	61%

3-methoxy butanol (2517-43-3) + 2-trifluoromethylbenzenesulfonyl chloride (776-04-5) → 3-methoxybutyl 2-(trifluoromethyl)benzenesulfonate

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 2h;	50%
With triethanolamine In dichloromethane

3-methoxy butanol (2517-43-3) + 4-(3-pyrazolyl)phenol → 3-[4-(3-methoxybutoxy)phenyl]pyrazole

Conditions	Yield
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 20℃; for 16h; Mitsunobu reaction;	47%

3-methoxy butanol (2517-43-3) + 4-trifluorophenylsulfonyl chloride (2991-42-6) → 3-methoxybutyl 4-(trifluoromethyl)benzenesulfonate

Conditions	Yield
With pyridine at 20℃; for 3.5h;	40%
In pyridine	40%

3-methoxy butanol (2517-43-3) + pentafluorobenzenesulonyl chloride (832-53-1) → 3-methoxybutyl 2,3,4,5,6-pentafluorobenzenesulfonate

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 4h;	36%

3-methoxy butanol (2517-43-3) + pentafluorobenzenesulonyl chloride (832-53-1) + sodium hydrogencarbonate (144-55-8) → 3-methoxybutyl 2,3,4,5,6-pentafluorobenzenesulfonate

Conditions	Yield
With triethanolamine In dichloromethane; ethyl acetate	36%

3-methoxy butanol (2517-43-3) + 1,7-dibromo-N,N'-bis(2,6-diisopropylphenyl)perylene-3,4:9,10-tetracarboxylic acid diimide (331861-94-0) → N,N′-bis(2,6-diisopropylphenyl)-1-bromo-7-(3-methoxybutoxy)perylene-3,4,9,10-tetracarboxylic diimide

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 3h; Inert atmosphere;	19%

Adipic acid (124-04-9) + 3-methoxy butanol (2517-43-3) → adipic acid bis-(3-methoxy-butyl ester) (59089-92-8)

Conditions	Yield
With toluene-4-sulfonic acid

3-methoxy butanol (2517-43-3) → 1-chloro-3-methoxy-butane (4446-87-1)

Conditions	Yield
With pyridine; thionyl chloride

Upstream product

• 5281-76-5 3-methoxybutanal 
• 67-56-1 methanol 
• 75-56-9 methyloxirane 
• 116-11-0 2-Methoxypropene 
• 201230-82-2 carbon monoxide 
• 1120-97-4 4-methyl-1,3-dioxane 
• 93185-29-6 1-acetoxy-3-(chloromethoxy)butane 

Downstream Products

• 65633-57-0 2-[4'-(2,4-dichlorophenoxy)-phenoxy]-propionic acid 3-methoxy-n-butyl ester 
• 4842-02-8 3-Jod-phthalsaeure-bis-(3-methoxy-butylester) 
• 4889-19-4 5-Jod-isophthalsaeure-bis-<3-methoxy-butylester> 
• 65633-36-5 2-[4-(4-Chloro-phenoxy)-phenoxy]-propionic acid 3-methoxy-butyl ester 
• 72325-99-6 (E)-4-[4-(4-Bromo-2-chloro-phenoxy)-phenoxy]-pent-2-enoic acid 3-methoxy-butyl ester 
• 28248-58-0 Thiophosphoric acid O-(3-methoxy-butyl) ester O'-methyl ester O''-(4-methylsulfanyl-phenyl) ester 
• 28248-69-3 Thiophosphoric acid O-ethyl ester O'-(3-methoxy-butyl) ester O''-(4-methylsulfanyl-phenyl) ester 
• 28239-66-9 Thiophosphoric acid O-(4-methanesulfinyl-phenyl) ester O'-(3-methoxy-butyl) ester O''-methyl ester 
• 28372-36-3 Thiophosphoric acid O-(3-methoxy-butyl) ester O'-methyl ester O''-(4-nitro-phenyl) ester 
• 28239-76-1 Thiophosphoric acid O-ethyl ester O'-(4-methanesulfinyl-phenyl) ester O''-(3-methoxy-butyl) ester 
• 28372-48-7 Thiophosphoric acid O-ethyl ester O'-(3-methoxy-butyl) ester O''-(4-nitro-phenyl) ester 
• 3540-60-1 <3-(4-Jod-benzoyloxy)-propionsaeure>-<3-methoxy-butylester> 
• 89-86-1 4-hydroxysalicylic acid 
• 1421060-11-8 carbonyl chlorohydride{bis[2-(dicyclohexylphosphino)ethyl]amine}ruthenium(II) 

Relevant articles and documents

Method for synthesizing gamma-alkoxy alcohol

The invention provides a synthesis method of gamma-alkoxy alcohol. The method comprises the following steps: in a synthesis gas atmosphere, sequentially carrying out hydroformylation and a hydrogenation reaction on an enol ether substrate under the action of a catalyst to obtain the gamma-alkoxy alcohol by a one-pot method. The method has the main advantages that a synthesis route is novel, the enol ether is creatively used as the raw material to prepare the gamma-alkoxy alcohol in one step, and compared with other synthesis methods used at present, the method of the invention has obvious advantages; and cobalt and alkyl phosphine with high hydrogenation activity are selected as catalyst ligands, and Lewis acid is selected as a carbonyl activation reagent, so the hydrogenation reaction activity of the system is further improved, the gamma-alkoxy alcohol is obtained by the one-pot method, the separation and purification of an unstable intermediate gamma-alkoxy aldehyde are avoided, andoperation is simpler, more convenient and safer.