89-91-8

Basic information

• Product Name: Methyl dimethoxyacetate
• Synonyms: Methyl dimethoxyacetate, 97+%;Methyl Dimethoxylacetate;Methyl dimethoxyacet;Methy1 2,2-dimethoxyacetate;Methyl diMethoxyacetate, 98% 25GR;Methyl diMethoxyacetate, 98% 5GR;Acetic acid,2,2-diMethoxy-, Methyl este;TwoMethoxy acetic acidMethyl ester
• CAS NO: 89-91-8
• Molecular Formula: C₅H₁₀O₄
• Molecular Weight: 134.13
• EINECS: 201-950-0
• Mol File: 89-91-8.mol
• Article Data: 21

Chemical Properties

• Boiling Point: 67 °C18 mm Hg(lit.)
• Flash Point: 146 °F
• Appearance: Clear colorless to very slightly yellow/Liquid
• Density: 1.096 g/mL at 25 °C(lit.)
• Vapor Pressure: 1.57mmHg at 25°C
• Refractive Index: n20/D 1.405(lit.)
• Storage Temp.: 0-6°C
• Solubility: Chloroform (Sparingly), Methanol (Slightly)
• Sensitive: Moisture Sensitive
• BRN: 1757582
• CAS DataBase Reference: Methyl dimethoxyacetate(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl dimethoxyacetate(89-91-8)
• EPA Substance Registry System: Methyl dimethoxyacetate(89-91-8)

Safety Data

• Safety Statements: 23-24/25
• WGK Germany: 3
• TSCA: Yes
• Hazardous Substances Data: 89-91-8(Hazardous Substances Data)

Usage

Chemical Properties

CLEAR COLOURLESS TO VERY SLIGHTLY YELLOW LIQUID

Uses

Methyl dimethoxyacetate has been used:in Claisen acylation of active hydrogen compoundsin preparation of 3, 9-disubstituted 2,4,8,10-tetroxaspiro [5.5] undecaneas Lithium enolate precursor as acylating reagent for cycloalkanone enolates and amino alcohols

InChI:InChI=1/C5H10O4/c1-7-4(6)5(8-2)9-3/h5H,1-3H3

Synthetic route

Glyoxilic acid (298-12-4) + trimethyl orthoformate (149-73-5) → Methyl dimethoxyacetate (89-91-8)

Conditions	Yield
With toluene-4-sulfonic acid at 20℃; for 72h; Inert atmosphere;	97%
With hydrogenchloride In methanol for 48h; Heating;	85%
With toluene-4-sulfonic acid for 3h;	79%
With sulfuric acid In methanol for 18h; Time; Reflux;	59.8%
With toluene-4-sulfonic acid Inert atmosphere;

Trimethyl borate (121-43-7) + N,N-diphenylaminobenzene (603-34-9) → Methyl dimethoxyacetate (89-91-8)

Conditions	Yield
With lithium iodide In diphenylether

glycolic acid methyl ester (96-35-5) + chloromethyl methyl ether (107-30-2) → Methyl dimethoxyacetate (89-91-8)

Conditions	Yield
With triethylamine In dichloromethane

trimethyl orthoformate (149-73-5) + 2,2-dihydroxyacetic acid (563-96-2) → Methyl dimethoxyacetate (89-91-8)

Conditions	Yield
With sulfuric acid In methanol for 18h; Heating;	46%

methanol (67-56-1) + sodium dimethoxy acetate → Methyl dimethoxyacetate (89-91-8)

Conditions	Yield
With hydrogenchloride

1,1,2,2-tetramethoxyethylene (1069-12-1) → methanol (67-56-1) + Methyl dimethoxyacetate (89-91-8)

Conditions	Yield
With water; perchloric acid In tetrahydrofuran at 25℃; Rate constant; Mechanism; isotope effect;
With water; cyanoacetic acid In tetrahydrofuran at 25℃; Rate constant; Mechanism;
With water; ClH2COOH In tetrahydrofuran at 25℃; Rate constant; Mechanism;

1-methylindole (603-76-9) + methyl 2-chloro-2-methoxyacetate (13157-96-5) → Methyl dimethoxyacetate (89-91-8) + methyl 2,2-bis(1-methyl-1H-indol-3-yl)acetate (138197-76-9) + 1,1'-dimethyl-2',3'-dihydro-1H,1'H-2,3'-biindolyl (6637-11-2)

Conditions	Yield
With zinc(II) chloride In tetrahydrofuran for 2h; Ambient temperature;	A 19% B 68% C 32%

methanol (67-56-1) + 2,2-dihydroxyacetic acid (563-96-2) → Methyl dimethoxyacetate (89-91-8)

Conditions	Yield
sulfuric acid for 5h; Heating;	58%

methanol (67-56-1) + Glyoxilic acid (298-12-4) → Methyl dimethoxyacetate (89-91-8) + 2-hydroxy-2-methoxyacetic acid (39140-61-9)

Conditions	Yield
In chloroform-d1 at 20℃;	A 6 %Spectr. B 37 %Spectr.

methanol (67-56-1) + methyl ethylsulfenylacetate (20600-64-0) → Methyl dimethoxyacetate (89-91-8)

Conditions	Yield
With thallium(III) nitrate

methanol (67-56-1) + 2,2-dimethoxyacetic acid (73569-40-1) → Methyl dimethoxyacetate (89-91-8)

Conditions	Yield
With hydrogenchloride

methanol (67-56-1) + Glyoxilic acid (298-12-4) → Methyl dimethoxyacetate (89-91-8)

Conditions	Yield
With hydrogenchloride

methanol (67-56-1) + methyl glyoxylate methyl hemi-acetal (109745-70-2, 19757-97-2) → Methyl dimethoxyacetate (89-91-8)

Conditions	Yield
With toluene-4-sulfonic acid

dichloroacetic acid methyl ester (116-54-1) + sodium methylate (124-41-4) → Methyl dimethoxyacetate (89-91-8)

Conditions	Yield
In methanol

Upstream product

• 67-56-1 methanol 
• 73569-40-1 2,2-dimethoxyacetic acid 
• 298-12-4 Glyoxilic acid 
• 79-43-6 dichloro-acetic acid 
• 124-41-4 sodium methylate 
• 17994-23-9 dichlorovinylene carbonate 
• 53175-28-3 2-chloro-2-butenal 
• 1116-86-5 1,1,5,5-tetramethoxy-pent-2-ene 
• 41527-39-3 dimethyl (2E)-pent-2-enedioate 
• 683-51-2 2-chloro-2-propenal 
• 109745-70-2 methyl glyoxylate methyl hemi-acetal 
• 1069-12-1 1,1,2,2-tetramethoxyethylene 
• 359-21-7 (E/Z)-1,2-dibromo-1,2-difluoroethylene 
• 116-54-1 dichloroacetic acid methyl ester 

Downstream Products

• 3058-09-1 2,4,8,10-tetraoxa-spiro[5.5]undecane-3,9-dicarboxylic acid dimethyl ester 
• 60705-25-1 4,4-dimethoxy-3-oxo-butyric acid methyl ester 
• 112047-43-5 2-dimethoxyacetyl-cyclohexanone 
• 55578-64-8 1,1-dimethoxy-2,4-pentanedione 
• 6956-50-9 ethyl 4,4-dimethoxy-3-oxo-butyrate 
• 65499-34-5 3-Hydroxy-2,2-dimethoxy-3-phenyl-butyric acid methyl ester 
• 65499-00-5 3-Hydroxy-2,2-dimethoxy-3-(3-methoxy-phenyl)-propionic acid methyl ester 
• 82206-55-1 Methyl glyoxylate (Z)-4-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)semicarbazone 
• 60432-13-5 Methyl glyoxylate (E)-4-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)semicarbazone 
• 144147-79-5 2-(2,2-Dimethoxy-acetyl)-6-ethyl-cyclohexanone 
• 144147-81-9 2-(2,2-Dimethoxy-acetyl)-6-propyl-cyclohexanone 
• 144147-87-5 2-sec-Butyl-6-(2,2-dimethoxy-acetyl)-cyclohexanone 
• 144147-78-4 3-(2,2-Dimethoxy-acetyl)-bicyclohexyl-2-one 
• 144147-83-1 2-Benzyl-6-(2,2-dimethoxy-acetyl)-cyclohexanone 

Relevant articles and documents

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