56718-70-8

Basic information

• Product Name: [[p-(2-methoxyethyl)phenoxy]methyl]oxirane
• Synonyms: [[p-(2-methoxyethyl)phenoxy]methyl]oxirane;[[4-(2-Methoxyethyl)phenoxy]methyl]-oxirane;2-[[4-(2-Methoxyethyl)phenoxy]methyl-oxirane;3-[4-(2-Methoxyethyl)phenoxy]-1,2-epoxypropane;MEEPB;1-(2-Methoxyethyl)-4-(2,3-epoxypropanoxy)benzene;1-(2-Methoxyethyl)-4-(oxiranylmethoxy)benzene;2,3-epoxypropyl 4-(2-methoxyethyl)phenyl ether
• CAS NO: 56718-70-8
• Molecular Formula: C₁₂H₁₆O₃
• Molecular Weight: 208.25364
• EINECS: 260-353-3
• Product Categories: Various Metabolites and Impurities;Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals
• Mol File: 56718-70-8.mol
• Article Data: 26

Chemical Properties

• Melting Point: 67-68℃ (ligroine )
• Boiling Point: 300.6 °C at 760 mmHg
• Flash Point: 100.1 °C
• Appearance: Pale-yellow oil
• Density: 1.099 g/cm³
• Vapor Pressure: 0.00199mmHg at 25°C
• Refractive Index: 1.519 (25℃)
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)
• CAS DataBase Reference: [[p-(2-methoxyethyl)phenoxy]methyl]oxirane(CAS DataBase Reference)
• NIST Chemistry Reference: [[p-(2-methoxyethyl)phenoxy]methyl]oxirane(56718-70-8)
• EPA Substance Registry System: [[p-(2-methoxyethyl)phenoxy]methyl]oxirane(56718-70-8)

Safety Data

• Hazardous Substances Data: 56718-70-8(Hazardous Substances Data)

Usage

Chemical Properties

Pale-Yellow Oil

InChI:InChI=1/C12H16O3/c1-13-7-6-10-2-4-11(5-3-10)14-8-12-9-15-12/h2-5,12H,6-9H2,1H3

Synthetic route

4-(2-methoxyethyl)phenol (56718-71-9) + epichlorohydrin (106-89-8) → 2-[4-(2'-methoxyethyl)phenoxymethyl]oxirane (56718-70-8)

Conditions	Yield
With sodium hydroxide at 85 - 90℃; pH=8; Temperature; pH-value; Flow reactor;	95.2%
With sodium hydroxide at 90 - 115℃; under 1500.15 - 2250.23 Torr; pH=9; Flow reactor;	95.2%
With sodium hydroxide In water at 40 - 45℃; for 3 - 5h;	93%

4-(2-methoxyethyl)phenol (56718-71-9) + epichlorohydrin (106-89-8) → 2-[4-(2'-methoxyethyl)phenoxymethyl]oxirane (56718-70-8) + (+/-)-1-[4-(2-methoxyethyl)phenoxy]-3-chloro-2-propanol (56718-76-4)

Conditions	Yield
With sodium hydroxide	A 90% B 10%
Stage #1: 4-(2-methoxyethyl)phenol With potassium hydroxide In methanol at 40 - 45℃; for 1h; Stage #2: epichlorohydrin at 40℃; for 24h;
With sodium hydroxide In water at 30 - 40℃; for 5h; Temperature;

Toluene-4-sulfonic acid 2-hydroxy-3-[4-(2-methoxy-ethyl)-phenoxy]-propyl ester (74254-83-4) → 2-[4-(2'-methoxyethyl)phenoxymethyl]oxirane (56718-70-8)

Conditions	Yield
With sodium methylate In methanol at 50 - 60℃; for 0.5h;	0.50 g

4-(2-methoxyethyl)phenol (56718-71-9) + 1,2-Epoxy-3-bromopropane (3132-64-7) → 2-[4-(2'-methoxyethyl)phenoxymethyl]oxirane (56718-70-8)

Conditions	Yield
With base

2-bromo-1-(4'-hydroxyphenyl)-1-ethanone (2491-38-5) → 2-[4-(2'-methoxyethyl)phenoxymethyl]oxirane (56718-70-8)

Conditions	Yield
Multi-step reaction with 3 steps 1: methanol 2: H2; AcOH / Pd/C 3: 90 percent / aq. NaOH View Scheme

alpha-methoxy-4-hydroxyacetophenone (32136-81-5) → 2-[4-(2'-methoxyethyl)phenoxymethyl]oxirane (56718-70-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: H2; AcOH / Pd/C 2: 90 percent / aq. NaOH View Scheme
Multi-step reaction with 5 steps 1: 96 percent / H2 / 10percent Pd/C / ethanol / 4 h / 2327.2 Torr 2: 85 percent / K2CO3 / acetone / 7 h / Heating 3: 80 percent / OsO4, N-methylmorpholine-N-oxide / H2O; acetone / 15 h 4: pyridine / 24 h / Ambient temperature 5: 0.50 g / NaOCH3 / methanol / 0.5 h / 50 - 60 °C View Scheme

4-Hydroxyacetophenone (99-93-4) → 2-[4-(2'-methoxyethyl)phenoxymethyl]oxirane (56718-70-8)

Conditions	Yield
Multi-step reaction with 4 steps 1: CuBr2 / ethyl acetate 2: methanol 3: H2; AcOH / Pd/C 4: 90 percent / aq. NaOH View Scheme

p-hydroxyphenacyl chloride (6305-04-0) → 2-[4-(2'-methoxyethyl)phenoxymethyl]oxirane (56718-70-8)

Conditions	Yield
Multi-step reaction with 6 steps 1: 90 percent / methanol / 24 h / Ambient temperature 2: 96 percent / H2 / 10percent Pd/C / ethanol / 4 h / 2327.2 Torr 3: 85 percent / K2CO3 / acetone / 7 h / Heating 4: 80 percent / OsO4, N-methylmorpholine-N-oxide / H2O; acetone / 15 h 5: pyridine / 24 h / Ambient temperature 6: 0.50 g / NaOCH3 / methanol / 0.5 h / 50 - 60 °C View Scheme

4-(2-methoxyethyl)phenol (56718-71-9) → 2-[4-(2'-methoxyethyl)phenoxymethyl]oxirane (56718-70-8)

Conditions	Yield
Multi-step reaction with 4 steps 1: 85 percent / K2CO3 / acetone / 7 h / Heating 2: 80 percent / OsO4, N-methylmorpholine-N-oxide / H2O; acetone / 15 h 3: pyridine / 24 h / Ambient temperature 4: 0.50 g / NaOCH3 / methanol / 0.5 h / 50 - 60 °C View Scheme

3-[4-(2-methoxyethyl)phenoxy]propylene (80448-05-1) → 2-[4-(2'-methoxyethyl)phenoxymethyl]oxirane (56718-70-8)

Conditions	Yield
Multi-step reaction with 3 steps 1: 80 percent / OsO4, N-methylmorpholine-N-oxide / H2O; acetone / 15 h 2: pyridine / 24 h / Ambient temperature 3: 0.50 g / NaOCH3 / methanol / 0.5 h / 50 - 60 °C View Scheme

3-<4-(2-methoxyethyl)phenoxy>-1,2-propanediol (62572-90-1) → 2-[4-(2'-methoxyethyl)phenoxymethyl]oxirane (56718-70-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: pyridine / 24 h / Ambient temperature 2: 0.50 g / NaOCH3 / methanol / 0.5 h / 50 - 60 °C View Scheme

phenol (108-95-2) → 2-[4-(2'-methoxyethyl)phenoxymethyl]oxirane (56718-70-8)

Conditions

Yield

Multi-step reaction with 7 steps 1: 50 percent / AlCl3 / various solvent(s) / 5 h / 70 °C 2: 90 percent / methanol / 24 h / Ambient temperature 3: 96 percent / H2 / 10percent Pd/C / ethanol / 4 h / 2327.2 Torr 4: 85 percent / K2CO3 / acetone / 7 h / Heating 5: 80 percent / OsO4, N-methylmorpholine-N-oxide / H2O; acetone / 15 h 6: pyridine / 24 h / Ambient temperature 7: 0.50 g / NaOCH3 / methanol / 0.5 h / 50 - 60 °C View Scheme

4-(2-methoxyethyl)phenol (56718-71-9) + epichlorohydrin (106-89-8) → C21H28O5 + 2-[4-(2'-methoxyethyl)phenoxymethyl]oxirane (56718-70-8) + (+/-)-1-[4-(2-methoxyethyl)phenoxy]-3-chloro-2-propanol (56718-76-4)

Conditions	Yield
With tetrabutyl-ammonium chloride at 110℃; under 2100.21 Torr; for 0.95h; Flow reactor;

(S)-epichlorohydrin (67843-74-7) + 4-(2-methoxyethyl)phenol (56718-71-9) → 2-[4-(2'-methoxyethyl)phenoxymethyl]oxirane (56718-70-8)

Conditions	Yield
With potassium carbonate In acetone Reflux;

isopropylamine (75-31-0) + 2-[4-(2'-methoxyethyl)phenoxymethyl]oxirane (56718-70-8) → (RS)-metoprolol (51384-51-1)

Conditions	Yield
In ethanol at 50 - 92℃; Temperature; Flow reactor;	99.58%
Stage #1: isopropylamine; 2-[4-(2'-methoxyethyl)phenoxymethyl]oxirane In N,N-dimethyl-formamide at 60℃; for 12h; Sealed tube; Stage #2: With water In N,N-dimethyl-formamide at 60℃; for 12h; Solvent; Temperature; Sealed tube; regioselective reaction;	95%
In water at 80℃; Flow reactor;	93.1%

2-[4-(2'-methoxyethyl)phenoxymethyl]oxirane (56718-70-8) → (+/-)-1-[4-(2-methoxyethyl)phenoxy]-3-chloro-2-propanol (56718-76-4)

Conditions	Yield
With morpholine; 1,3,5-trichloro-2,4,6-triazine In water at 20℃; for 0.5h;	98%
Stage #1: 2-[4-(2'-methoxyethyl)phenoxymethyl]oxirane With β‐cyclodextrin In water; acetone at 60℃; Stage #2: With thionyl chloride In water; acetone at 20℃; for 10h;	91%
With zirconyl chloride In acetonitrile at 20℃; for 1.16667h;	80%
With water; acetyl chloride In dichloromethane for 12h;

2-[4-(2'-methoxyethyl)phenoxymethyl]oxirane (56718-70-8) → (RS)-1-bromo-3-[4-(2-methoxy-ethyl)-phenoxy]-propan-2-ol

Conditions	Yield
With dimethylbromosulphonium bromide In acetonitrile at 20℃; for 0.333333h;	98%
With acetic acid; lithium bromide In tetrahydrofuran at 20℃; for 12h;

acetic anhydride (108-24-7) + 2-[4-(2'-methoxyethyl)phenoxymethyl]oxirane (56718-70-8) → acetic acid 1-acetoxymethyl-2-[4-(2-methoxy-ethyl)-phenoxy]-ethyl ester

Conditions	Yield
With ammonium molybdophosphate at 20℃; for 1h;	96%

pivaloyl chloride (3282-30-2) + 2-[4-(2'-methoxyethyl)phenoxymethyl]oxirane (56718-70-8) → C17H25ClO4

Conditions	Yield
With iron(III) chloride In neat (no solvent) at 20℃; for 0.0833333h; regiospecific reaction;	96%

succinic acid (110-15-6) + isopropylamine (75-31-0) + 2-[4-(2'-methoxyethyl)phenoxymethyl]oxirane (56718-70-8) → metoprolol Succinate

Conditions	Yield
Stage #1: isopropylamine; 2-[4-(2'-methoxyethyl)phenoxymethyl]oxirane In ethanol at 50 - 92℃; Flow reactor; Stage #2: succinic acid In ethanol Reflux;	95.6%

2-[4-(2'-methoxyethyl)phenoxymethyl]oxirane (56718-70-8) → 2-[4-(2-methoxyethyl)phenoxymethyl]thiirane (750614-73-4)

Conditions	Yield
With thiourea; β‐cyclodextrin In water; acetone at 20℃; for 3.5h;	94%
With potassium thioacyanate; β‐cyclodextrin In water; acetone at 20℃; for 4h;	92%
With potassium thioacyanate In various solvent(s) at 20℃; for 0.75h;	89%

thiobenzoic acid (98-91-9) + 2-[4-(2'-methoxyethyl)phenoxymethyl]oxirane (56718-70-8) → thiobenzoic acid S-{2-hydroxy-3-[4-(2-methoxy-ethyl)-phenoxy]-propyl} ester

Conditions	Yield
With β‐cyclodextrin In water; acetone at 20℃; for 8h;	94%

thiophenol (108-98-5) + 2-[4-(2'-methoxyethyl)phenoxymethyl]oxirane (56718-70-8) → C18H22O3S (934538-08-6)

Conditions	Yield
With magnesium oxide; copper at 20℃; for 0.333333h; chemoselective reaction;	94%

sodium phenoxide (139-02-6) + 2-[4-(2'-methoxyethyl)phenoxymethyl]oxirane (56718-70-8) → 1-[4-(2-methoxyethyl)phenoxy]-3-phenoxy-2-propanol

Conditions	Yield
With β‐cyclodextrin In water; acetone at 60℃; for 8h;	92%
With PEG-400 at 20℃; for 2.5h;	88%

p-Chlorothiophenol (106-54-7) + 2-[4-(2'-methoxyethyl)phenoxymethyl]oxirane (56718-70-8) → C18H21ClO3S (934538-09-7)

Conditions	Yield
With magnesium oxide; copper at 20℃; for 0.333333h; chemoselective reaction;	92%

thiophenol (108-98-5) + 2-[4-(2'-methoxyethyl)phenoxymethyl]oxirane (56718-70-8) → C18H22O4S (1236110-91-0)

Conditions	Yield
Stage #1: thiophenol; 2-[4-(2'-methoxyethyl)phenoxymethyl]oxirane With magnesium oxide; copper at 20℃; Stage #2: With dihydrogen peroxide In water at 20℃; for 1.25h; chemoselective reaction;	91%

para-thiocresol (106-45-6) + 2-[4-(2'-methoxyethyl)phenoxymethyl]oxirane (56718-70-8) → C19H24O3S (1236110-89-6)

Conditions	Yield
With magnesium oxide; copper at 20℃; for 0.333333h; chemoselective reaction;	91%

2-[4-(2'-methoxyethyl)phenoxymethyl]oxirane (56718-70-8) + sodium 4-chlorophenolate (1193-00-6) → 1-(4-chlorophenoxy)-3-[4-(2-methoxyethyl)phenoxy]-2-propanol

Conditions	Yield
With β‐cyclodextrin In water; acetone at 60℃; for 8h;	90%
With PEG-400 at 20℃; for 3h;	85%

2-[4-(2'-methoxyethyl)phenoxymethyl]oxirane (56718-70-8) + thioacetic acid (507-09-5) → thioacetic acid S-{2-hydroxy-3-[4-(2-methoxy-ethyl)-phenoxy]-propyl} ester

Conditions	Yield
With β‐cyclodextrin In water; acetone at 20℃; for 8h;	90%

p-Chlorothiophenol (106-54-7) + 2-[4-(2'-methoxyethyl)phenoxymethyl]oxirane (56718-70-8) → C18H21ClO4S (1236110-93-2)

Conditions	Yield
Stage #1: p-Chlorothiophenol; 2-[4-(2'-methoxyethyl)phenoxymethyl]oxirane With magnesium oxide; copper at 20℃; Stage #2: With dihydrogen peroxide In water at 20℃; for 1.25h; chemoselective reaction;	90%

4-methoxy-aniline (104-94-9) + 2-[4-(2'-methoxyethyl)phenoxymethyl]oxirane (56718-70-8) → 1-[4-(2-methoxy-ethyl)-phenoxy]-3-(4-methoxy-phenylamino)-propan-2-ol

Conditions	Yield
With β‐cyclodextrin In water; acetone at 20℃;	89%

2-[4-(2'-methoxyethyl)phenoxymethyl]oxirane (56718-70-8) → 1-[4-(2-methoxy-ethyl)-phenoxy]-3-nitrooxy-propan-2-ol

Conditions	Yield
With bismuth(III) nitrate In acetonitrile at 20℃; for 1.5h;	89%
With zirconyl nitrate In acetonitrile at 20℃; for 5h;	85%

para-thiocresol (106-45-6) + 2-[4-(2'-methoxyethyl)phenoxymethyl]oxirane (56718-70-8) → C19H24O4S (1236110-92-1)

Conditions	Yield
Stage #1: para-thiocresol; 2-[4-(2'-methoxyethyl)phenoxymethyl]oxirane With magnesium oxide; copper at 20℃; Stage #2: With dihydrogen peroxide In water at 20℃; for 1.25h; chemoselective reaction;	89%

sodium 4-methoxyphenolate (1122-95-8) + 2-[4-(2'-methoxyethyl)phenoxymethyl]oxirane (56718-70-8) → 1-[4-(2-methoxyethyl)phenoxy]-3-(4-methoxyphenoxy)-2-propanol

Conditions	Yield
With β‐cyclodextrin In water; acetone at 60℃; for 8h;	88%

2-[4-(2'-methoxyethyl)phenoxymethyl]oxirane (56718-70-8) → 3-<4-(2-methoxyethyl)phenoxy>-1,2-propanediol (62572-90-1)

Conditions	Yield
With β‐cyclodextrin In methanol; water at 40℃; for 6h;	85%

2-[4-(2'-methoxyethyl)phenoxymethyl]oxirane (56718-70-8) + 2-hydroxyethanethiol (60-24-2) → C14H22O4S (1236110-90-9)

Conditions	Yield
With magnesium oxide; copper at 20℃; for 0.5h; chemoselective reaction;	85%

benzoic acid (65-85-0) + 2-[4-(2'-methoxyethyl)phenoxymethyl]oxirane (56718-70-8) → C19H22O5

Conditions	Yield
With sodium hydrogencarbonate In acetonitrile at 50℃; for 6h; Reagent/catalyst; Solvent;	83%

Benzeneselenol (645-96-5) + 2-[4-(2'-methoxyethyl)phenoxymethyl]oxirane (56718-70-8) → 1-[4-(2-methoxy-ethyl)-phenoxy]-3-phenylselanyl-propan-2-ol

Conditions	Yield
Stage #1: 2-[4-(2'-methoxyethyl)phenoxymethyl]oxirane With β‐cyclodextrin In water; acetone Stage #2: Benzeneselenol In water; acetone at 20℃; for 0.583333h;	82%

2-[4-(2'-methoxyethyl)phenoxymethyl]oxirane (56718-70-8) → (R)-1-[4-(2-methoxyethyl)]phenyl glycerol + (2S)-2-{[4-(2-Methoxyethyl)phenoxy]methyl}oxirane (105780-38-9) + (R)-2-{[4-(2-methoxyethyl)phenoxy]methyl}oxirane (133397-54-3)

Conditions	Yield
With Salen-Co(III)OAc In water Ambient temperature;	A 49% B 45% C n/a

(S)-2-aminobutan-1-ol (5856-62-2) + 2-[4-(2'-methoxyethyl)phenoxymethyl]oxirane (56718-70-8) → (2S)-2-[[(2R)-2-hydroxy-3-[4-(2-methoxyethyl)phenoxy]propyl]amino]-1-butanol + (2S)-2-[[(2S)-2-hydroxy-3-[4-(2-methoxyethyl)phenoxy]propyl]amino]-1-butanol

Conditions	Yield
In water at 20℃; for 24h;	A 25% B 43%

(2,3-dihydrobenzo[1,4]dioxin-2-ylmethyl)amine (4442-59-5) + 2-[4-(2'-methoxyethyl)phenoxymethyl]oxirane (56718-70-8) → 1-[(2,3-Dihydro-benzo[1,4]dioxin-2-ylmethyl)-amino]-3-[4-(2-methoxy-ethyl)-phenoxy]-propan-2-ol; hydrochloride

Conditions	Yield
In methanol for 2h; Heating;	26%

N-(2-aminoethyl)-4-(1H-imidazol-1-yl)benzamide hydrochloride (120690-14-4) + 2-[4-(2'-methoxyethyl)phenoxymethyl]oxirane (56718-70-8) → N-[2-[[2-Hydroxy-3-(4-(2-methoxyethyl)phenoxy)propyl]amino]ethyl]-4-(1H-imidazol-1-yl)benzamide (128263-89-8)

Conditions	Yield
With sodium hydroxide In methanol; water at 60℃; for 17h;	11%

Upstream product

• 56718-71-9 4-(2-methoxyethyl)phenol 
• 3132-64-7 1,2-Epoxy-3-bromopropane 
• 67843-74-7 (S)-epichlorohydrin 
• 106-89-8 epichlorohydrin 
• 108-95-2 phenol 
• 62572-90-1 3-<4-(2-methoxyethyl)phenoxy>-1,2-propanediol 
• 80448-05-1 3-[4-(2-methoxyethyl)phenoxy]propylene 
• 6305-04-0 p-hydroxyphenacyl chloride 
• 99-93-4 4-Hydroxyacetophenone 
• 32136-81-5 alpha-methoxy-4-hydroxyacetophenone 
• 2491-38-5 2-bromo-1-(4'-hydroxyphenyl)-1-ethanone 
• 74254-83-4 Toluene-4-sulfonic acid 2-hydroxy-3-[4-(2-methoxy-ethyl)-phenoxy]-propyl ester 

Downstream Products

• 105780-38-9 (2S)-2-{[4-(2-Methoxyethyl)phenoxy]methyl}oxirane 
• 133397-54-3 (R)-2-{[4-(2-methoxyethyl)phenoxy]methyl}oxirane 
• 934538-08-6 C₁₈H₂₂O₃S 
• 1236110-91-0 C₁₈H₂₂O₄S 
• 1236110-89-6 C₁₉H₂₄O₃S 
• 1236110-92-1 C₁₉H₂₄O₄S 
• 934538-09-7 C₁₈H₂₁ClO₃S 
• 1236110-93-2 C₁₈H₂₁ClO₄S 
• 1236110-90-9 C₁₄H₂₂O₄S 
• 1339949-16-4 (S)-1-bromo-3-[4-(2-methoxy-ethyl)-phenoxy]-propan-2-ol 
• 113798-79-1 (R)-1-bromo-3-[4-(2-methoxy-ethyl)-phenoxy]-propan-2-yl acetate 
• 56718-76-4 (+/-)-1-[4-(2-methoxyethyl)phenoxy]-3-chloro-2-propanol 
• 691841-17-5 1-benzylamino-3-[4-(2-methoxy-ethyl)-phenoxy]-propan-2-ol 

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