627-40-7

Basic information

• Product Name: ALLYL METHYL ETHER
• Synonyms: 3-methoxy-1-propen;3-Methoxypropene;3-Methoxy-propene;4-Oxapent-1-ene;CH2=CHCH2OCH3;Ether, allyl methyl;Methyl 2-propenyl ether;Methyl2-propenylether
• CAS NO: 627-40-7
• Molecular Formula: C₄H₈O
• Molecular Weight: 72.11
• EINECS: 210-997-6
• Mol File: 627-40-7.mol
• Article Data: 43

Chemical Properties

• Melting Point: -115.8°C (estimate)
• Boiling Point: 42-43°C
• Flash Point: -23°C
• Appearance: /Liquid
• Density: 0.768 g/mL at 25 °C
• Vapor Pressure: 354mmHg at 25°C
• Refractive Index: 1.3803
• Storage Temp.: Refrigerator
• Water Solubility: Insoluble in water
• CAS DataBase Reference: ALLYL METHYL ETHER(CAS DataBase Reference)
• NIST Chemistry Reference: ALLYL METHYL ETHER(627-40-7)
• EPA Substance Registry System: ALLYL METHYL ETHER(627-40-7)

Safety Data

• Hazard Codes: F+,Xn,F
• Statements: 11-19-36-22-12
• Safety Statements: 3/7-9-16-36/37/39-26
• RIDADR: 3271
• WGK Germany: 3
• TSCA: Yes
• HazardClass: 3
• PackingGroup: II
• Hazardous Substances Data: 627-40-7(Hazardous Substances Data)

Usage

Chemical Properties

colorless liquid

Uses

Allyl methyl ether it used as pharmaceutical intermediate.

InChI:InChI=1/C4H8O/c1-3-4-5-2/h3H,1,4H2,2H3

Synthetic route

1-methoxy-2-propanol (107-98-2) → methylallylether (627-40-7)

Conditions	Yield
With zirconium(IV) oxide at 100℃; for 3h; Temperature; Reagent/catalyst;	96.6%

allyl alcohol (107-18-6) + methyl iodide (74-88-4) → methylallylether (627-40-7)

Conditions	Yield
With dimsylsodium In dimethyl sulfoxide Ambient temperature;	93%
With silver(l) oxide
With sodium hydride In paraffin

3,3-dimethoxyprop-1-ene (6044-68-4) → methylallylether (627-40-7)

Conditions	Yield
With benzo[1,3,2]dioxaborole In benzene Ambient temperature;	88%

sodium methylate (124-41-4) + allyl bromide (106-95-6) → methylallylether (627-40-7)

Conditions	Yield
In methanol	80%

magnesium methanolate (109-88-6, 16436-83-2, 16436-85-4) + allyl bromide (106-95-6) → methylallylether (627-40-7)

Conditions	Yield
for 48h; Heating;	78%

methanol (67-56-1) + 3-chloroprop-1-ene (107-05-1) → methylallylether (627-40-7)

Conditions	Yield
With sodium methylate at 35 - 45℃; for 4h;	74.1%
Stage #1: methanol With sodium Inert atmosphere; Reflux; Stage #2: 3-chloroprop-1-ene for 4h; Inert atmosphere; Reflux;	67%

propargyl alcohol methyl ether (627-41-8) → methyl propyl ether (557-17-5) + methylallylether (627-40-7)

Conditions	Yield
With hydrogen; palladium dichloride In N,N-dimethyl-formamide under 18751.5 Torr; for 0.666667h; Product distribution; Ambient temperature; various time;	A 2% B 68.4%
Stage #1: propargyl alcohol methyl ether With pyridine In toluene for 0.166667h; Glovebox; Stage #2: With hydrogen In toluene at 120℃; under 37503.8 Torr; for 12h; Glovebox;

allyl alcohol (107-18-6) + dimethyl sulfate (77-78-1) → methylallylether (627-40-7)

Conditions	Yield
With sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride In water at 40 - 45℃; for 3h;	65%
With sodium hydride 1. 1 h; 2.overnight; Multistep reaction;
With sodium hydride In xylene Heating;
With sodium hydride In xylene

Dichloromethyl methyl ether (4885-02-3) + (Z)-(3-methoxyprop-1-ene-1,2-diyl)bis(trimethylstannane) (78338-53-1, 85263-66-7) → methylallylether (627-40-7)

Conditions	Yield
With aluminium trichloride	61%

allyl alcohol; aluminium allylate (25439-17-2) + methyl iodide (74-88-4) → methylallylether (627-40-7)

Conditions	Yield
In N,N-dimethyl-formamide at 59 - 70℃; for 48h;	60%

propargyl alcohol methyl ether (627-41-8) → methylallylether (627-40-7)

Conditions	Yield
With piperazine; hydrogen In ethanol at 80℃; under 4500.45 Torr; for 24h;	56%
With piperazine; hydrogen In ethanol at 100℃; under 4500.45 Torr; for 22h; Green chemistry;
With hydrogen In ethanol at 100℃; under 4500.45 Torr; for 24h; chemoselective reaction;	76 %Chromat.

Trimethyl orthoacetate (1445-45-0) + allyl alcohol (107-18-6) → methylallylether (627-40-7) + Allyl ether (557-40-4)

Conditions	Yield
Montmorillonite KSF at 20℃; for 8h;	A 86 % Chromat. B 5%

1,2-epithio-3-methoxypropane (19858-14-1) + triethyl phosphite (122-52-1) → O,O,O-triethyl phosphorothioate (126-68-1) + methylallylether (627-40-7)

methanol (67-56-1) + 3-ethoxyprop-1-ene (557-31-3) → methylallylether (627-40-7)

Conditions	Yield
With sulfuric acid; mercury(II) diacetate

methanol (67-56-1) + Allyl ether (557-40-4) → methylallylether (627-40-7)

Conditions	Yield
With boron fluoride ether; mercury(II) diacetate

allyl iodid (556-56-9) + sodium methylate (124-41-4) → methylallylether (627-40-7)

propylene glycol methyl ether acetate (108-65-6) → methyl (Z)-prop-1-enyl ether (4188-68-5) + (E)-1-Methoxy-1-propen (4188-69-6) + methylallylether (627-40-7)

Conditions	Yield
at 500℃;

propylene glycol methyl ether acetate (108-65-6) → methyl (Z)-prop-1-enyl ether (4188-68-5) + methylallylether (627-40-7)

Conditions	Yield
at 500℃;

propylene glycol methyl ether acetate (108-65-6) → (E)-1-Methoxy-1-propen (4188-69-6) + methylallylether (627-40-7)

Conditions	Yield
at 500℃;

glycerol 1-monomethyl ether (623-39-2, 36887-04-4) + oxalic acid (144-62-7) → methylallylether (627-40-7)

Conditions	Yield
With ammonium sulfate at 180 - 230℃;

methanol (67-56-1) + allyl alcohol (107-18-6) → methylallylether (627-40-7)

Conditions	Yield
With sulfuric acid; mercury(II) diacetate
With sodium aluminium sulfate dodecahydrate at 185 - 190℃;

sodium allyloxide (20907-32-8) + allyl alcohol (107-18-6) + dimethyl sulfate (77-78-1) → methylallylether (627-40-7)

Conditions	Yield
Darstellung;

sodium methylate (124-41-4) + 1,3-dibromo-propane (109-64-8) → methylallylether (627-40-7)

Conditions	Yield
With methanol

oxirane (75-21-8) + methanol (67-56-1) + N-nitroso-N-cyclopropylurea (10575-90-3) → methylallylether (627-40-7) + monoethylene glycol methyl allyl ether (18854-48-3) + cyclopropyl methyl ether (540-47-6) + 3-<2-(2-Methoxyethoxy)ethoxy>propen (13752-97-1) + (2-Methoxyethoxy)cyclopropan

Conditions	Yield
With sodium hydrogencarbonate Product distribution; Ambient temperature; var. conc., further reactions with NaOCH3, oxetane, tetrahydrofuran;	A 31.7 % Chromat. B 49.3 % Chromat. C 2.8 % Chromat. D 13.8 % Chromat. E 2.4 % Chromat.

trimethylene oxide (503-30-0) + diazomethane (186581-53-3, 908094-01-9) + methanol (67-56-1) → 3-methyloxetane (2167-38-6) + tetrahydrofuran (109-99-9) + (+/-)-2-methyloxetane (2167-39-7) + Dimethyl ether (115-10-6) + 1,3-dimethoxy propane (17081-21-9) + methylallylether (627-40-7)

Conditions	Yield
Mechanism; Irradiation;

...Expand

trimethylene oxide (503-30-0) + diazomethane (186581-53-3, 908094-01-9) + methanol (67-56-1) → 3-methyloxetane (2167-38-6) + tetrahydrofuran (109-99-9) + (+/-)-2-methyloxetane (2167-39-7) + methylallylether (627-40-7)

Conditions	Yield
Irradiation; Yield given. Further byproducts given. Yields of byproduct given;

trimethylene oxide (503-30-0) + diazomethane (186581-53-3, 908094-01-9) → 3-methyloxetane (2167-38-6) + tetrahydrofuran (109-99-9) + (+/-)-2-methyloxetane (2167-39-7) + methylallylether (627-40-7)

Conditions	Yield
Irradiation; Yield given. Yields of byproduct given;
Mechanism; Irradiation;

trimethylene oxide (503-30-0) + methanol (67-56-1) + N-nitroso-N-cyclopropylurea (10575-90-3) → methylallylether (627-40-7) + cyclopropyl methyl ether (540-47-6) + 1-methoxy-3-(2-propenyloxy)-propane + (3-Methoxypropoxy)cyclopropan

Conditions	Yield
With sodium hydrogencarbonate Ambient temperature; Further byproducts given;	A 67.1 % Chromat. B 9.2 % Chromat. C 16.9 % Chromat. D 3.7 % Chromat.

trimethylene oxide (503-30-0) + methanol (67-56-1) + N-nitroso-N-cyclopropylurea (10575-90-3) → methylallylether (627-40-7) + cyclopropyl methyl ether (540-47-6) + 1-methoxy-3-(2-propenyloxy)-propane + 3-<3-(3-Methoxypropoxy)propoxy>propen

Conditions	Yield
With sodium hydrogencarbonate Ambient temperature; Further byproducts given;	A 68.2 % Chromat. B 8.8 % Chromat. C 16.8 % Chromat. D 3.3 % Chromat.

trimethylene oxide (503-30-0) + N-nitroso-N-cyclopropylurea (10575-90-3) + sodium methylate (124-41-4) → methylallylether (627-40-7) + cyclopropyl methyl ether (540-47-6) + 1-methoxy-3-(2-propenyloxy)-propane + (3-Methoxypropoxy)cyclopropan

Conditions	Yield
	A 1.7 % Chromat. B 39.5 % Chromat. C 0.4 % Chromat. D 58.4 % Chromat.

methylallylether (627-40-7) + Methanesulfonyl azide (624-90-8, 1516-70-7) → N-[1-Methoxy-prop-(Z)-ylidene]-methanesulfonamide

Conditions	Yield
bis(benzonitrile)palladium(II) dichloride In benzene at 80℃;	100%

methylallylether (627-40-7) → glycidyl methyl ether (930-37-0)

Conditions	Yield
With tetrabutylphosphonium peroxotantalate; dihydrogen peroxide In water; acetonitrile at 0℃; for 5.5h; Schlenk technique; chemoselective reaction;	100%
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 45℃; for 48h;
With peracetic acid IP versus log k (rel); var. electrophiles;

methylallylether (627-40-7) + 3-phenylsulfanyl-propionaldehyde (27098-65-3) → C6H5SC2H4CHOC3H5OCH3 (945037-26-3)

Conditions	Yield
With boron trifluoride diethyl etherate; sec.-butyllithium; (+)-B-methoxydiisocamphenylborane In tetrahydrofuran at -78 - 0℃;	100%

methylallylether (627-40-7) + 1,1,4,4-tetramethoxy-2-butene (5370-08-1) → 1,8-dimethoxy-1,3,6,8-tetramethoxy-2,7-dimethyl-4-octene (90031-29-1)

Conditions	Yield
With SO42-Sc2O3-CoO-TiO2 solid super acid In toluene at 15℃; for 5h; Reagent/catalyst; Temperature;	98.2%
With SO42--TiO2-Fe3O4 solid super acid catalyst In toluene at 30℃; for 0.0263889h; Temperature; Reagent/catalyst; Flow reactor;

methylallylether (627-40-7) → bis(2-bromo-3-methoxypropyl)selenide

Conditions	Yield
With selenium dibromide In chloroform at 20 - 25℃; for 18h; regioselective reaction;	97%

methylallylether (627-40-7) + benzyldimethylsilane (1631-70-5) → benzyl(3-methoxypropyl)dimethylsilane (145675-44-1)

Conditions	Yield
With bis(1,5-cyclooctadiene)diiridium(I) dichloride In dichloromethane at 20℃; Glovebox;	96%

N,N-bis(phosphinoethyl)methoxyethylamine (879129-61-0) + methylallylether (627-40-7) → N-(2-methoxyethyl)-N,N-bis(2-(bis(3-methoxypropyl)phosphino)ethyl)amine hydrochloride

Conditions	Yield
With 2,2'-azobis(isobutyronitrile) In ethanol at 80℃; for 20h;	95%

methylallylether (627-40-7) + di-p-tolylphosphine (1017-60-3) → (3-methoxypropyl)di-4-tolylphosphine (1163249-39-5)

Conditions	Yield
Irradiation;	92%

methylallylether (627-40-7) → methoxypropanol (1589-49-7)

Conditions	Yield
Stage #1: methylallylether With diborane In dimethyl sulfoxide Inert atmosphere; Stage #2: With dihydrogen peroxide; sodium hydroxide In dimethyl sulfoxide Reagent/catalyst; Solvent;	91.2%

methylallylether (627-40-7) → Methoxyallene (13169-00-1)

Conditions	Yield
With potassium tert-butylate for 3h; Heating;	91%

methylallylether (627-40-7) + cyclohexanone (108-94-1) → 2-allylcyclohexan-1-one (94-66-6)

Conditions	Yield
With pyrrolidine; 1,1'-bis-(diphenylphosphino)ferrocene; bis(η3-allyl-μ-chloropalladium(II)) In methanol at 20℃; for 4h; Inert atmosphere; regioselective reaction;	91%

methylallylether (627-40-7) + (2R,3R)-1-benzyloxy-3,4-epoxy-2-butanol (72229-13-1) → (2R,3R)-1-benzyloxy-3,4-epoxy-2-(1'-methoxy-1'-methylaethoxy)-butan (78469-76-8)

Conditions	Yield
With 2,4,6-Trinitrophenol In dichloromethane for 0.5h; Ambient temperature;	90%

methylallylether (627-40-7) + tricarbonyl(1,5,9-triphosphacyclododecane)chromium (177702-90-8) → [Cr(CO)3(C21H45O3P3)] (187665-24-3)

Conditions	Yield
With 2,2'-azobis(isobutyronitrile) In toluene (N2); reflux (80°C, 3 h); filtration (Celite), solvent removal (vac.), extn. (CH2Cl2), chromy. (SiO2; CH2Cl2), evapn. (vac.); elem. anal.;	90%

methylallylether (627-40-7) + (E)-2-methyl-3-(2-methylthiazol-4-yl)acrylaldehyde (184246-38-6) → C12H17NO2S (1174394-71-8)

Conditions	Yield
Stage #1: methylallylether With sec.-butyllithium; (+)-B-methoxydiisocamphenylborane In tetrahydrofuran; cyclohexane at -78℃; asymmetric Brown allylation; Stage #2: (E)-2-methyl-3-(2-methylthiazol-4-yl)acrylaldehyde With boron trifluoride diethyl etherate In tetrahydrofuran; cyclohexane at -78℃; for 12h; asymmetric Brown allylation; optical yield given as %ee;	88%

(-)-(10R)-B-methoxy-10-trimethylsilyl-9-borabicyclo[3.3.2]decane (856675-96-2) + methylallylether (627-40-7) → (10R)-B-[(Z)-γ-methoxyallyl]-10-trimethylsilyl-9-borabicyclo[3.3.2]decane (1161746-10-6)

Conditions	Yield
Stage #1: methylallylether With sec.-butyllithium In tetrahydrofuran; cyclohexane at -78℃; for 0.5h; Inert atmosphere; Stage #2: (-)-(10R)-B-methoxy-10-trimethylsilyl-9-borabicyclo[3.3.2]decane In tetrahydrofuran; cyclohexane at -78℃; for 2h; Inert atmosphere; Stage #3: With chloro-trimethyl-silane In tetrahydrofuran; cyclohexane at -78℃; for 0.5h; Inert atmosphere;	85%

(10R)-(-)-9-methoxy-10-trimethylsilyl-9-borabicyclo[3.3.2.]decane + methylallylether (627-40-7) → (10R)-B-[(Z)-γ-methoxyallyl]-10-trimethylsilyl-9-borabicyclo[3.3.2]decane

Conditions	Yield
Stage #1: methylallylether With sec.-butyllithium In tetrahydrofuran; cyclohexane at -78℃; for 0.5h; Inert atmosphere; Stage #2: (10R)-(-)-9-methoxy-10-trimethylsilyl-9-borabicyclo[3.3.2.]decane In tetrahydrofuran; cyclohexane at -78℃; for 2h; Inert atmosphere; Stage #3: With chloro-trimethyl-silane In tetrahydrofuran; cyclohexane at -78℃; for 0.166667h; Inert atmosphere;	85%

methylallylether (627-40-7) + phenylmethanethiol (100-53-8) → benzyl(3-methoxypropyl)sulfane

Conditions	Yield
With titanium(IV) oxide In acetonitrile at 20℃; for 16h; Sealed tube; Irradiation;	85%

diazoacetic acid ethyl ester (623-73-4) + methylallylether (627-40-7) → (+/-)trans-ethyl-2-(methoxymethyl)cyclopropanecarboxylate

Conditions	Yield
>Cu(OTf) In 1,2-dichloro-ethane for 5h; Ambient temperature;	83%

phthalimide (136918-14-4) + methylallylether (627-40-7) + di(4-tosyl)amine (3695-00-9) → N-(2-(1,3-dioxoisoindolin-2-yl)-3-methoxypropyl)-4-methyl-N-tosylbenzene

Conditions	Yield
With 4-tert-Butylcatechol; bis(tertbutylcarbonyloxy)iodobenzene; diphthalimidato-bis(benzonitrile)palladium(II) In 1,2-dichloro-ethane at 70℃; for 16h; chemoselective reaction;	82%

methylallylether (627-40-7) + C17H19NO5S → C21H25NO5S

Conditions	Yield
With pyridinium p-toluenesulfonate In toluene at 100℃; for 2h; Inert atmosphere;	81%

sodium azide + methylallylether (627-40-7) + mercury(II) diacetate (1600-27-7) → 2-azido-1-chloromercurio-3-methoxypropane

Conditions	Yield
In methanol Kinetics; soln. of alkene quick addn. to soln. of Hg-compd. and azide (about 20°C); mixture pouring to aq. soln. of NaCl, extracting (CHCl3), organic layer washing (water) and drying (MgSO4), solvent removing (reduced pressure);	80%

methylallylether (627-40-7) + 3,4-dimethoxyphenylmagnesium bromide (89980-69-8) → 1,2-dimethoxy-4-(2-propenyl)benzene (93-15-2)

Conditions	Yield
With methylmagnesium bromide; bis(triphenylphosphine)nickel(II) chloride In diethyl ether; benzene Heating;	79%

diazomethane (186581-53-3, 908094-01-9) + methylallylether (627-40-7) → cyclopropylmethyl methyl ether (1003-13-0)

Conditions	Yield
bis(benzonitrile)palladium(II) dichloride In dichloromethane at 0 - 10℃;	78%
bis(benzonitrile)palladium(II) dichloride In diethyl ether; dichloromethane at 0 - 10℃; for 0.5h;	74%
copper dichloride

methylallylether (627-40-7) + p-toluenesulfonyl iodide (1950-78-3) → 2-iodo-1-methoxy-3-tosylpropane

Conditions	Yield
In dichloromethane for 0.25h; Irradiation;	78%

methylallylether (627-40-7) + diphenylsilane (775-12-2) → (3-methoxypropyl)diphenylsilane

Conditions	Yield
With [N,N'-(1,2-dimethyl-1,2-ethanediylidene)bis[3-(diphenylphosphino)-1-propanamine]]Ni In benzene-d6 at 60℃; for 1h; Temperature; Inert atmosphere;	77%

Upstream product

• 67-56-1 methanol 
• 557-40-4 Allyl ether 
• 107-18-6 allyl alcohol 
• 20907-32-8 sodium allyloxide 
• 77-78-1 dimethyl sulfate 
• 74-88-4 methyl iodide 
• 75-21-8 oxirane 
• 10575-90-3 N-nitroso-N-cyclopropylurea 
• 503-30-0 trimethylene oxide 
• 186581-53-3 diazomethane 
• 124-41-4 sodium methylate 
• 109-99-9 tetrahydrofuran 
• 7575-57-7 allyl benzenesulfonate 
• 34557-54-5 methane 

Downstream Products

• 5836-66-8 1,2-dibromo-3-methoxypropane 
• 1003-13-0 cyclopropylmethyl methyl ether 
• 54020-52-9 methyl 2-methoxy-4-pentenoate 
• 64584-02-7 (2-(methoxymethyl)cyclopropyl)benzene 
• 53356-81-3 1-(1-Hydroxycyclohexyl)allylmethylether 
• 22103-90-8 cis-1-Phenyl-2-methoxymethyl-cyclopropan 
• 22103-90-8 (±)-trans-[2-(methoxymethyl)cyclopropyl]benzene 
• 99165-27-2 1-Chloro-1-(3-methoxy-propyl)-silinane 
• 34680-34-7 1,2-Dichlor-3-methoxy-propane 
• 34680-56-3 1-Chlor-2,3-dimethoxy-propane 
• 34680-57-4 2-Chlor-1,3-dimethoxy-propane 
• 187737-37-7 propene 
• 1825-61-2 Trimethylmethoxysilane 
• 762-72-1 allyl-trimethyl-silane 

Relevant articles and documents

Raman spectroscopic study of allyl methyl ether (3-methoxy-1-propene), CH2=CHCH2OCH3, and some isotopically labelled analogues

Fourier-transform Raman spectra of allyl methyl ether, CH2=CHCH2OCH3, three deuterated derivatives and one 13C derivative have been obtained.Comparison of the spectra of the deuterated and protiated compounds in conjunction with polarization data has enabled full vibrational assignments to be made for the carbon-hydrogen modes and the 13C data have identified some skeletal modes of the CO and CC bonds.As a result of the data obtained from the deuterated compounds in particular, some initial suggestions have been revised for tentative literature assignments of molecules of biological interest.In other cases, confirmation of existing assignments have been made.

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