10304-09-3

Basic information

• Product Name: methoxy(oxo)acetic acid
• CAS NO: 10304-09-3
• Molecular Formula: C₃H₃O₄*K
• Molecular Weight: 104.0615
• Mol File: 10304-09-3.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 192.9°C at 760 mmHg
• Flash Point: 88.9°C
• Density: 1.366g/cm³
• Vapor Pressure: 0.209mmHg at 25°C
• Refractive Index: 1.42
• CAS DataBase Reference: methoxy(oxo)acetic acid(CAS DataBase Reference)
• NIST Chemistry Reference: methoxy(oxo)acetic acid(10304-09-3)
• EPA Substance Registry System: methoxy(oxo)acetic acid(10304-09-3)

Safety Data

• Hazardous Substances Data: 10304-09-3(Hazardous Substances Data)

Usage

General Description

Methoxy(oxo)acetic acid, also known as methoxyacetic acid or MAA, is a chemical compound with the formula CH3OCH2COOH. It is a colorless liquid with a pungent odor and is soluble in water. MAA is commonly used in the production of various industrial and consumer products such as herbicides, dyes, and pharmaceuticals. It is also used as a solvent and in the manufacturing of polymers and plastics. MAA can be toxic if inhaled, ingested, or absorbed through the skin, and exposure to high levels of the compound can cause irritation to the skin, eyes, and respiratory system. Additionally, it has been associated with reproductive and developmental toxicity in animal studies, leading to its classification as a possible human reproductive hazard. Therefore, proper safety precautions and handling protocols should be followed when working with or around this chemical.

Synthetic route

Dimethyl oxalate (553-90-2) → potassium oxalate monomethyl ester (10304-09-3)

Conditions	Yield
With potassium acetate In methanol; water at 80℃; for 3h;	100%
With potassium acetate In methanol; water at 80℃; for 3h;	91%
With potassium acetate In methanol; water at 60℃; for 1h;	80%
With potassium acetate In methanol; water at 90℃; for 2h; Reflux;

potassium oxalate monomethyl ester (10304-09-3) + (2R)-2,3-diaminopropanoic acid monohydrochloride (1482-97-9, 6018-55-9, 6018-56-0, 19777-68-5, 19777-69-6, 28843-13-2, 54897-59-5, 69531-11-9, 125767-61-5) → β-N-oxalyl-D-α,β-diaminopropionic acid

Conditions	Yield
Stage #1: (2R)-2,3-diaminopropanoic acid monohydrochloride With lithium hydroxide monohydrate In methanol; water for 1h; Cooling with ice; Stage #2: potassium oxalate monomethyl ester In methanol; water at 20℃; for 18h; Concentration;	77%

potassium oxalate monomethyl ester (10304-09-3) + 4-bromo-<2,3,5,6-2H4>anisole (152404-45-0) → C9H6(2)H4O3

Conditions	Yield
With 1,3-bis-(diphenylphosphino)propane; palladium dichloride In 1-methyl-pyrrolidin-2-one at 150℃; for 24h; Inert atmosphere; Schlenk technique;	75%

triphenylplumbyl hydroxide (894-08-6) + potassium oxalate monomethyl ester (10304-09-3) → (C6H5)3PbO2CCO2CH3 (107399-19-9)

Conditions	Yield
With methanol In methanol HO2CCO2CH3 prepared in situ from potassium salt in methanol, pptd. at room temp. by equimolar amount of R3MOH; suspn. in CH3OH warmed, solvent vol. reduced; elem. anal.;	74%

potassium oxalate monomethyl ester (10304-09-3) + Trimethylbleimonohydroxyd (17546-98-4) → (CH3)3PbO2CCO2CH3 (107399-17-7)

Conditions	Yield
With methanol In methanol HO2CCO2CH3 prepared in situ from potassium salt in methanol, pptd. at room temp. by equimolar amount of R3MOH; suspn. in CH3OH warmed, solvent vol. reduced; elem. anal.;	70%

triphenyltin(IV) hydroxide (76-87-9) + potassium oxalate monomethyl ester (10304-09-3) → (C6H5)3SnO2CCO2CH3 (107399-18-8)

Conditions	Yield
With methanol In methanol HO2CCO2CH3 prepared in situ from potassium salt in methanol, pptd. at room temp. by equimolar amount of R3MOH; suspn. in CH3OH warmed, solvent vol. reduced; elem. anal.;	65%

potassium oxalate monomethyl ester (10304-09-3) + trimethyltin(IV) hydroxide (56-24-6) → (CH3)3SnO2CCO2CH3 (107399-16-6)

Conditions	Yield
With methanol In methanol HO2CCO2CH3 prepared in situ from potassium salt and methanol, pptd. at room temp. by equimolar amount R3MOH; suspn. in CH3OH warmed, solvent vol. reduced; elem. anal.;	56%

para-bromotoluene (106-38-7) + potassium oxalate monomethyl ester (10304-09-3) → 4-methyl-benzoic acid methyl ester (99-75-2)

Conditions	Yield
With palladium(II) trifluoroacetate; 1,3-bis-(diphenylphosphino)propane In 1-methyl-pyrrolidin-2-one at 150℃; for 24h; Inert atmosphere;	52%

Ethyl 2-bromohexanoate (615-96-3) + potassium oxalate monomethyl ester (10304-09-3) → 1-ethoxy-1-oxohexan-2-yl methyl oxalate

Conditions	Yield
In dimethyl sulfoxide at 20℃; for 48h; Inert atmosphere;	49%

monomethyl oxalyl chloride (5781-53-3) + potassium oxalate monomethyl ester (10304-09-3) → methoxalic anhydride (5781-55-5)

Conditions	Yield
(i) aq. KOAc, MeOH, (ii) /BRN= 1071541/, benzene,; Multistep reaction;

menadione (58-27-5) + potassium oxalate monomethyl ester (10304-09-3) → 2,3-dimethyl[1,4]naphthoquinone (2197-57-1)

Conditions	Yield
With ammonium peroxydisulfate; silver nitrate In acetonitrile

menadione (58-27-5) + potassium oxalate monomethyl ester (10304-09-3) → 3-methyl-1,4-dioxo-1,4-dihydronaphthalene-2-carboxylic acid methyl ester (68749-80-4)

Conditions	Yield
With ammonium peroxydisulfate; silver nitrate In acetonitrile

menadione (58-27-5) + potassium oxalate monomethyl ester (10304-09-3) → 2-Methyl-1,4-dioxo-1,2,3,4-tetrahydro-naphthalene-2,3-dicarboxylic acid dimethyl ester (68749-81-5)

Conditions	Yield
With ammonium peroxydisulfate; silver nitrate In acetonitrile

3-Bromojuglone (52431-65-9) + potassium oxalate monomethyl ester (10304-09-3) → 2-Methoxycarbonyl-3-bromjuglon (68749-89-3)

Conditions	Yield
With ammonium peroxydisulfate; silver nitrate In acetonitrile

2-benzyl-1,4-naphthoquinone (33440-68-5) + potassium oxalate monomethyl ester (10304-09-3) → 2‐benzyl‐3‐methylnaphthalene‐1,4‐dione (52711-59-8)

Conditions	Yield
With ammonium peroxydisulfate; silver nitrate In acetonitrile

2-benzyl-1,4-naphthoquinone (33440-68-5) + potassium oxalate monomethyl ester (10304-09-3) → 2-Benzyl-3-methoxycarbonyl-1.4-naphthochinon

Conditions	Yield
With ammonium peroxydisulfate; silver nitrate In acetonitrile

potassium oxalate monomethyl ester (10304-09-3) + [1,4]naphthoquinone (130-15-4) → 2,3-dimethoxycarbonyl-1,4-naphthoquinone (68749-78-0)

Conditions	Yield
With ammonium peroxydisulfate; silver nitrate In acetonitrile

1H-imidazole (288-32-4) + potassium oxalate monomethyl ester (10304-09-3) → α-oxo-1H-imidazole-1-acetic acid, methyl ester (72030-76-3)

Conditions	Yield
With oxalyl dichloride; methanesulfonic acid 1.) acetonitrile, RT, 5 min, 2.) acetonitrile, RT, 20 min; Yield given. Multistep reaction;

potassium oxalate monomethyl ester (10304-09-3) + (R)-2-tert-butoxycarbonyl-3-aminopropionic acid (73259-81-1, 113625-76-6, 76387-70-7) → β-N-oxalyl-D-α,β-diaminopropionic acid

Conditions	Yield
Stage #1: (R)-2-tert-butoxycarbonyl-3-aminopropionic acid With water; lithium hydroxide In methanol at 0 - 5℃; for 0.666667h; pH=Ca. 8; Stage #2: potassium oxalate monomethyl ester In methanol; water at 0 - 20℃; for 20h;	930 g

Upstream product

• 553-90-2 Dimethyl oxalate 

Downstream Products

• 99-75-2 4-methyl-benzoic acid methyl ester 
• 107399-18-8 (C₆H₅)3SnO₂CCO₂CH₃ 
• 107399-19-9 (C₆H₅)3PbO₂CCO₂CH₃ 
• 52711-59-8 2‐benzyl‐3‐methylnaphthalene‐1,4‐dione 
• 5781-55-5 methoxalic anhydride 

Relevant articles and documents

Preparation and plant growth-regulatory activity of N'-substituted N- furfuryloxamides

N'-Substituted N-furfuryloxamides (4) were prepared via condensation of potassium methyl oxalate (8) with furfurylamine (5f) using 1,1'- oxalyldiimidazole (6), followed by hydrolysis of the resulting amide-ester (10), and finally condensation with aliphatic or aromatic amines (5). The prepared compounds (4) were examined for activity as plant growth regulators using two kinds of plant seeds, namely, those of rape, Brassica campestris L. (Dicotyledoneae) and leek, Allium tuberosum ROTTLER (Monocotyledoneae). N'- Benzyl- and N'-phenyl-N-furfuryloxamides (4b and 4c) and N,N'- difurfuryloxamide (4f) inhibited root growth in seedlings of both species.

Synthesis of aromatic esters via Pd-catalyzed decarboxylative coupling of potassium oxalate monoesters with aryl bromides and chlorides

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