42245-42-1

Basic information

• Product Name: Methyl 3-(4-methoxyphenyl)oxirane-2-carboxylate
• Synonyms: METHYL TRANS-3-(4-METHOXYPHENYL)GLYCIDATE;3-(4-methoxyphenyl)-oxiranecarboxylicacimethylester;3-(-methoxyphenyl)glycidicacidmethylester;methyl 3-(p-methoxyphenyl)oxirane-2-carboxylate;Oxiranecarboxylic acid, 3-(4-methoxyphenyl)-, methyl ester;TRANS-2,3-EPOXY-3(4-METHOXYPHENYL)-PROPIONICACIDMETHYLES.;METHYL 3-(4-METHOXYPHENYL)OXIRANE-2-CARBOXYLATE;3-(4-Methoxyphenyl)-oxiranecarboxylic acid methyl ester
• CAS NO: 42245-42-1
• Molecular Formula: C₁₁H₁₂O₄
• Molecular Weight: 208.21
• EINECS: 255-735-1
• Product Categories: API intermediates;Epoxide Monomers;Monomers;Polymer Science
• Mol File: 42245-42-1.mol
• Article Data: 16

Chemical Properties

• Melting Point: 69-71 °C(lit.)
• Boiling Point: 297.7 °C at 760 mmHg
• Flash Point: 129.2 °C
• Appearance: /
• Density: 1.224 g/cm³
• Vapor Pressure: 0.00133mmHg at 25°C
• Refractive Index: 1.534
• Solubility: Dichloromethane; Chloroform; Ethyl Acetate; DMSO
• CAS DataBase Reference: Methyl 3-(4-methoxyphenyl)oxirane-2-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl 3-(4-methoxyphenyl)oxirane-2-carboxylate(42245-42-1)
• EPA Substance Registry System: Methyl 3-(4-methoxyphenyl)oxirane-2-carboxylate(42245-42-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 3
• Hazardous Substances Data: 42245-42-1(Hazardous Substances Data)

Usage

Description

Methyl 2,3 epoXY-3-(4-methoxyphenyl)propionate is an intermediate product in the synthesis of diltiazem hydrochloride. Contact dermatitis was observed in several laboratory technicians.

Uses

Methyl trans-3-(4-Methoxyphenyl)glycidate is an intermediate used in the synthesis of Clentiazem (C573035), which is a benzothiazepine-like calcium antagonists; Enhances endothelium-dependent coronary artery relaxation.

Contact allergens

Methyl 2,3 epoxy-3-(4-methoxyphenyl)propionate is an intermediate product in the synthesis of diltiazem hydrochloride. Contact dermatitis was observed in several laboratory technicians.

InChI:InChI=1/C11H12O4/c1-13-8-5-3-7(4-6-8)9-10(15-9)11(12)14-2/h3-6,9-10H,1-2H3

Synthetic route

4-methoxy-benzaldehyde (123-11-5) + methyl chloroacetate (96-34-4) → methyl 3-(4-methoxyphenyl)glycidate (42245-42-1)

Conditions	Yield
With sodium methylate In ethanol at 5 - 35℃; for 2h;	88.4%
With sodium methylate In methanol 1) -10 deg C, 1.5 h; 2) -5 deg C, 1 h; 3) room temperature, 3 h;	70%
Stage #1: methyl chloroacetate With sodium methylate In methanol for 0.0833333h; Cooling with ice; Stage #2: 4-methoxy-benzaldehyde In methanol at 0℃;	41%

3-(4-methoxy-phenyl)acrylic acid methyl ester (3901-07-3) → methyl 3-(4-methoxyphenyl)glycidate (42245-42-1) + 3-Chloro-benzoic acid (1S,2S)-2-hydroxy-2-methoxycarbonyl-1-(4-methoxy-phenyl)-ethyl ester

Conditions	Yield
With sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid In dichloromethane; water for 1.5h; Ambient temperature;

3-(4-methoxy-phenyl)acrylic acid methyl ester (3901-07-3) + 3-chloro-benzenecarboperoxoic acid (937-14-4) → methyl 3-(4-methoxyphenyl)glycidate (42245-42-1) + 3-Chloro-benzoic acid (1S,2S)-2-hydroxy-2-methoxycarbonyl-1-(4-methoxy-phenyl)-ethyl ester

Conditions	Yield
In dichloromethane for 1.5h; Ambient temperature;

(E)-3-(4-methoxyphenyl)acrylic acid (943-89-5) → methyl 3-(4-methoxyphenyl)glycidate (42245-42-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: H2SO4 2: m-chloroperbenzoic acid, sodium bicarbonate / CH2Cl2; H2O / 1.5 h / Ambient temperature View Scheme
Multi-step reaction with 2 steps 1: H2SO4 2: CH2Cl2 / 1.5 h / Ambient temperature View Scheme

4-methoxy-benzaldehyde (123-11-5) + (+-)-2-cyano-3-m-tolyl-propionic acid hydrazide → methyl 3-(4-methoxyphenyl)glycidate (42245-42-1)

Conditions	Yield
Multi-step reaction with 3 steps 2: H2SO4 3: m-chloroperbenzoic acid, sodium bicarbonate / CH2Cl2; H2O / 1.5 h / Ambient temperature View Scheme
Multi-step reaction with 3 steps 2: H2SO4 3: CH2Cl2 / 1.5 h / Ambient temperature View Scheme

methyl 3-(4-methoxyphenyl)glycidate (42245-42-1) → Potassium; (2S,3R)-3-(4-methoxy-phenyl)-oxirane-2-carboxylate

Conditions	Yield
With potassium hydroxide In ethanol for 3h; Ambient temperature;	95.4%

methyl 3-(4-methoxyphenyl)glycidate (42245-42-1) + N-methyl-2-(2-(2-(4-phenyl-1-piperidyl)ethoxy)phenyl)thiazolidine-3-carbothioamide oxalate (107336-58-3) → N-methyl-2-{2-[2-(4-phenylpiperidine-1-yl)ethyloxy]phenyl}thiazolidine-3-carboxamide (107335-95-5)

Conditions	Yield
In ethanol	82.3%

methyl 3-(4-methoxyphenyl)glycidate (42245-42-1) → methyl 2,3-dideuterio-3-[(4-methoxy)phenyl]propanoate

Conditions	Yield
Stage #1: methyl 3-(4-methoxyphenyl)glycidate With samarium diiodide In tetrahydrofuran at 20℃; for 2h; Stage #2: With water-d2 In tetrahydrofuran at 20℃; for 12h; Further stages.;	81%

methyl 3-(4-methoxyphenyl)glycidate (42245-42-1) → 3-(4-methoxy-phenyl)acrylic acid methyl ester (3901-07-3)

Conditions	Yield
With samarium diiodide In tetrahydrofuran at 20℃; for 1.5h;	79%

methyl 3-(4-methoxyphenyl)glycidate (42245-42-1) + (N)-methyl-2-(2-(2-(4-phenylpiperazino)ethoxy)phenyl)thiazolidine-3-thiocarboxamide (103074-00-6) → N-methyl-2-{2-[2-(4-phenylpiperazin-1-yl)ethyloxy]phenyl}thiazolidine-3-carboxamide (103072-76-0)

Conditions	Yield
In ethanol	75.7%

2-amino-5-chlorobenzenethiol (23474-98-8) + methyl 3-(4-methoxyphenyl)glycidate (42245-42-1) → (+)-threo-2-hydroxy-3-(2-amino-5-chlorophenylthio)-3-(4-methoxyphenyl)propionic acid methyl ester

Conditions	Yield
In di-isopropyl ether; toluene	68%
In di-isopropyl ether; toluene	68%
In toluene

methyl 3-(4-methoxyphenyl)glycidate (42245-42-1) + 2-amino-5-methoxy-thiophenol (6274-29-9) → threo-2-hydroxy-3-<(2-amino-5-methoxyphenyl)thio>-3-(4-methoxyphenyl)propionic acid methyl ester (100601-17-0, 132618-96-3)

Conditions	Yield
In toluene for 6h; Heating;	63%

methyl 3-(4-methoxyphenyl)glycidate (42245-42-1) + 4-methoxy-phenol (150-76-5) → 2-hydroxy-3-(4-methoxy-phenoxy)-3-(4-methoxy-phenyl)propionic acid methyl ester (1621069-96-2)

Conditions	Yield
With tetrabutyl ammonium fluoride; silver nitrate In isopropyl alcohol at 60 - 80℃; for 8.5h;	61%

methyl 3-(4-methoxyphenyl)glycidate (42245-42-1) + (E)-3-methylpentyl-3-en-1-amine hydrochloride → 2-(4-methoxy-benzyl)-3,4-dimethyl-piperidin-4-ol (18175-34-3)

Conditions	Yield
With hydrogenchloride In water at 85 - 90℃; for 36h;	57.1%

2-butyl ethyl ether (625-54-7) + methyl 3-(4-methoxyphenyl)glycidate (42245-42-1) + 2-nitrothiophenol (4875-10-9) → methyl 2-hydroxy-3-(4-methoxyphenyl)-3-(2-nitrophenylthio)propionate (30067-00-6)

Conditions	Yield
With trifluoroborane diethyl ether	51.3%

methyl 3-(4-methoxyphenyl)glycidate (42245-42-1) → methyl 2-hydroxy-3-(4-methoxyphenyl)-3-(2-nitrophenylthio)propionate (30067-00-6)

Conditions	Yield
In ethyl acetate; benzene	47.1%

methyl 3-(4-methoxyphenyl)glycidate (42245-42-1) + C6H13N*ClH → 2-(4-methoxy-benzyl)-3,4-dimethyl-piperidin-4-ol (18175-34-3)

Conditions	Yield
With water; sodium hydroxide at 90 - 95℃; for 48h; pH=6 - 7;	45%

methyl 3-(4-methoxyphenyl)glycidate (42245-42-1) + β-naphthol (135-19-3) → C20H16O4 (1446468-30-9) + methyl 1-(4-methoxyphenyl)-1,2-dihydronaphtho[2,1-b]furan-2-carboxylate

Conditions	Yield
With aluminum (III) chloride In chloroform at 20℃; for 0.5h; Reagent/catalyst;	A 38% B 32%
With tris(p-bromophenylammoniumyl) hexachloroantimonate In dichloromethane at 20℃; for 0.5h; Reagent/catalyst; Solvent; chemoselective reaction;	A 20 %Spectr. B 72 %Spectr.

methyl 3-(4-methoxyphenyl)glycidate (42245-42-1) + triphenylborane (1095-03-0) → (2RS,3RS)-methyl 3-(4-methoxyphenyl)-3-phenoxy-2-hydroxy-propanoate + (2SR,3RS)-methyl 3-(4-methoxyphenyl)-3-phenoxy-2-hydroxy-propanoate

Conditions	Yield
In tetrahydrofuran; N,N-dimethyl-formamide at 20℃; for 2h;	A n/a B 20%

methyl 3-(4-methoxyphenyl)glycidate (42245-42-1) + 2-(cyclopent-1-en-1-yl) ethan-1-amine (3197-72-6) → 1-(4-methoxy-benzyl)-octahydro-[2]pyrindin-4a-ol (143207-89-0)

Conditions	Yield
With hydrogenchloride

methyl 3-(4-methoxyphenyl)glycidate (42245-42-1) + 2-(cyclohept-1-en-1-yl)ethan-1-amine (4431-14-5) → 1-(4-methoxy-benzyl)-decahydro-cyclohepta[c]pyridin-4a-ol (109569-42-8)

Conditions	Yield
With hydrogenchloride

methyl 3-(4-methoxyphenyl)glycidate (42245-42-1) + 2-(1-cyclohexenyl)ethylamine (3399-73-3) → 1-(4-methoxy-benzyl)-octahydro-isoquinolin-4a-ol (63477-92-9)

Conditions	Yield
With hydrogenchloride

methyl 3-(4-methoxyphenyl)glycidate (42245-42-1) + 2-(methylamino)benzenethiol (21749-63-3) → 2-Hydroxy-3-(4-methoxy-phenyl)-3-(2-methylamino-phenylsulfanyl)-propionic acid methyl ester (31966-75-3)

methyl 3-(4-methoxyphenyl)glycidate (42245-42-1) + 2-(2-diethylamino-ethylamino)-benzenethiol (31964-34-8) → 4-(2-diethylamino-ethyl)-4H-benzo[1,4]thiazin-3-one (46874-56-0)

Conditions	Yield
at 130 - 140℃; for 3h;

methyl 3-(4-methoxyphenyl)glycidate (42245-42-1) + 2-(2-diethylamino-ethylamino)-benzenethiol (31964-34-8) → 3-[2-(2-Diethylamino-ethylamino)-phenylsulfanyl]-2-hydroxy-3-(4-methoxy-phenyl)-propionic acid methyl ester (31964-35-9)

methyl 3-(4-methoxyphenyl)glycidate (42245-42-1) → 4-Methoxyphenylacetaldehyde (5703-26-4)

Conditions	Yield
With sodium methylate; acetic acid 1.) CH3OH, benzene, 0-5 deg C, 2.) reflux, 3 h; Multistep reaction;
With sodium methylate; acetic acid 1) methanol, ether, water, 5 deg C, 3 h; 2) benzene, reflux, 3 h; Yield given. Multistep reaction;
Multi-step reaction with 2 steps 1: potassium hydroxide / water / 5 h / 15 - 20 °C 2: potassium dihydrogenphosphate / water; dichloromethane / 5 h View Scheme
Multi-step reaction with 2 steps 1: potassium hydroxide / ethanol / 8 h / 0 - 15 °C 2: potassium dihydrogenphosphate / dichloromethane; water / 4 h / 20 °C View Scheme

methyl 3-(4-methoxyphenyl)glycidate (42245-42-1) → methyl (2R,3S)-3-(4-methoxyphenyl)glycidate (105560-93-8) + (2S,3R)-trans-(4-methoxyphenyl)glycidic acid (106003-21-8)

Conditions	Yield
With water In acetone at 25℃; Rhizopus arrhizus mycelium lipase, pH 7;

methyl 3-(4-methoxyphenyl)glycidate (42245-42-1) → methyl (2R,3S)-3-(4-methoxyphenyl)glycidate (105560-93-8)

methyl 3-(4-methoxyphenyl)glycidate (42245-42-1) + 2-nitrothiophenol (4875-10-9) → methyl 2-hydroxy-3-(4-methoxyphenyl)-3-(2-nitrophenylthio)propionate (30067-00-6)

Conditions	Yield
In acetonitrile

methyl 3-(4-methoxyphenyl)glycidate (42245-42-1) + 4-chloro-2-nitro-thiophenol (36776-27-9) → 3-(4-Chloro-2-nitro-phenylsulfanyl)-2-hydroxy-3-(4-methoxy-phenyl)-propionic acid methyl ester (30067-02-8)

Conditions	Yield
In acetonitrile

methyl 3-(4-methoxyphenyl)glycidate (42245-42-1) + 2-amino-benzenethiol (137-07-5) → (2RS,3RS)-3-(2'-aminophenylthio)-2-hydroxy-3-(4''-methoxyphenyl)-propionic acid methyl ester (30193-56-7)

methyl 3-(4-methoxyphenyl)glycidate (42245-42-1) → methyl 2-hydroxy-3-(4-methoxyphenyl)acrylate (103988-43-8)

Conditions	Yield
zinc(II) perchlorate In toluene Heating;

Upstream product

• 123-11-5 4-methoxy-benzaldehyde 
• 96-34-4 methyl chloroacetate 
• 67-56-1 methanol 
• 81860-68-6 3-(4-methoxyphenyl)-oxiranecarbonitrile 
• 943-89-5 (E)-3-(4-methoxyphenyl)acrylic acid 
• 3901-07-3 3-(4-methoxy-phenyl)acrylic acid methyl ester 
• 937-14-4 3-chloro-benzenecarboperoxoic acid 

Downstream Products

• 23515-44-8 5-(2-dimethylamino-ethyl)-3c-hydroxy-2r-(4-methoxy-phenyl)-2,3-dihydro-5H-benzo[b][1,4]thiazepin-4-one 
• 195616-20-7 (2S,3S)-3-(2-aminophenylthio)-2-hydroxy-3-(4-methoxyphenyl)propionamide 
• 222292-12-8 (2S,3R)-3-(2-Amino-phenylsulfanyl)-2-hydroxy-3-(4-methoxy-phenyl)-propionic acid methyl ester 
• 42399-49-5 (2S,3S)-3-hydroxy-2-(4-methoxyphenyl)-2,3-dihydro-1,5-benzothiazepin-4(5H)-one 
• 3901-07-3 3-(4-methoxy-phenyl)acrylic acid methyl ester 
• 134931-64-9 methyl (-)-(2R,3S)-3-(4-methoxyphenyl)glycidate 
• 103988-43-8 methyl 2-hydroxy-3-(4-methoxyphenyl)acrylate 
• 27068-88-8 3c-hydroxy-2r-(4-methoxy-phenyl)-2,3-dihydro-5H-benzo[b][1,4]thiazepin-4-one 
• 30193-56-7 (2RS,3RS)-3-(2'-aminophenylthio)-2-hydroxy-3-(4''-methoxyphenyl)-propionic acid methyl ester 
• 30067-02-8 3-(4-Chloro-2-nitro-phenylsulfanyl)-2-hydroxy-3-(4-methoxy-phenyl)-propionic acid methyl ester 
• 30067-00-6 methyl 2-hydroxy-3-(4-methoxyphenyl)-3-(2-nitrophenylthio)propionate 
• 30193-56-7 3-(2-Amino-phenylsulfanyl)-2-hydroxy-3-(4-methoxy-phenyl)-propionic acid methyl ester 
• 30193-56-7 methyl threo-2-hydroxy-3-(4-methoxyphenyl)-3-(2-aminophenylthio)propionate 

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