106675-70-1

Basic information

• Product Name: N,N'-Dimethoxy-N,N'-dimethyloxamide
• Synonyms: N,N'-DIMETHOXY-N,N'-DIMETHYLOXAMIDE;N,N'-OXALYLBIS[METHOXY(METHYL)AMINE];N-N'-DiMethoxy-N-N'-diMethyloxaldiaMide;N1,N2-DiMethoxy-N1,N2-diMethyloxalaMide;N1,N2-Dimethoxy-N1,N2-dimethyloxalamid;N,N'-Dimethoxy-N,N'-dimethyloxamide
• CAS NO: 106675-70-1
• Molecular Formula: C₆H₁₂N₂O₄
• Molecular Weight: 176.17
• Product Categories: Hydroxylamines;Hydroxylamines (N-Substituted);Hydroxylamines (O-Substituted);Amides;Carbonyl Compounds;Organic Building Blocks
• Mol File: 106675-70-1.mol

Chemical Properties

• Melting Point: 89-95 °C
• Boiling Point: 192.2 °C at 760 mmHg
• Flash Point: 70.1 °C
• Appearance: /
• Density: 1.181 g/cm³
• Storage Temp.: Sealed in dry,Room Temperature
• Water Solubility: Soluble in water
• BRN: 5330464
• CAS DataBase Reference: N,N'-Dimethoxy-N,N'-dimethyloxamide(CAS DataBase Reference)
• NIST Chemistry Reference: N,N'-Dimethoxy-N,N'-dimethyloxamide(106675-70-1)
• EPA Substance Registry System: N,N'-Dimethoxy-N,N'-dimethyloxamide(106675-70-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 106675-70-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
N,N'-Dimethoxy-N,N'-dimethyloxamide is used as a synthetic intermediate for the preparation of N-aryl and heteroarylamide compounds. These compounds are known to act as modulators of store-operated calcium (SOC) channels, which play a significant role in various cellular processes, including signal transduction, gene expression, and cell migration. By modulating the activity of SOC channels, N-aryl and heteroarylamide compounds have the potential to be developed into therapeutic agents for the treatment of various diseases and conditions.
Used in Chemical Synthesis:
In the field of chemical synthesis, N,N'-Dimethoxy-N,N'-dimethyloxamide is utilized as a versatile building block for the creation of a wide range of chemical compounds. Its unique structure allows for various chemical reactions, such as substitution, condensation, and rearrangement, which can lead to the formation of novel molecules with diverse properties and applications. This makes it a valuable asset in the development of new materials, catalysts, and other specialty chemicals.

Upstream product

• 79-37-8 oxalyl dichloride 
• 6638-79-5 N,O-dimethylhydroxylamine*hydrochloride 
• 95-92-1 oxalic acid diethyl ester 
• 3155-16-6 diphenyl oxalate 
• 2050-60-4 di-n-butyl oxalate 
• 553-90-2 Dimethyl oxalate 
• 615-81-6 diisopropyl oxalate 
• 1634-04-4 tert-butyl methyl ether 
• 144-62-7 oxalic acid 
• 1117-97-1 N,0-dimethylhydroxylamine 

Downstream Products

• 3457-46-3 4,4'-dichlorobenzil 
• 141694-36-2 2-(4-chlorophenyl)-N-methyl-2-oxoacetamide 
• 141694-27-1 N-Methoxy-N-methyl-α-oxo-4'-chlorobenzeneacetamide 
• 1226-42-2 1,2-bis(4-methoxyphenyl)-1,2-ethanedione 
• 244264-57-1 2-(4-methoxyphenyl)-N-methyl-2-oxoacetamide 
• 141694-26-0 N-Methyl-α-oxo-3-phenylpropanamide 
• 141694-29-3 N-Methoxy-N-methyl-α-oxobenzenepropanamide 
• 141694-33-9 N-Methyl-α-oxocyclohexaneacetamide 
• 141694-30-6 N-Methoxy-N-methyl-α-oxocyclohexaneacetamide 
• 141694-25-9 N-methoxy-N-methyl-α-oxo-benzeneacetamide 
• 83490-71-5 N?methyl?2?oxo?2?phenylacetamide 
• 134-81-6 benzil 
• 3457-48-5 1,2-di(4-methylphenyl)-1,2-ethanedione 
• 141694-35-1 N-methyl-2-oxo-2-(p-tolyl)acetamide 

Relevant articles and documents

Asymmetric Transfer Hydrogenation of α-Keto Amides; Highly Enantioselective Formation of Malic Acid Diamides and α-Hydroxyamides

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Weinreb amides were prepared directly from carboxylic acids, N,O-dimethylhydroxylamine, and phosphorus trichloride in one pot at 60 °C in toluene in high yields, thus avoiding the separation of the moisture and air sensitive intermediate P[NMe(OMe)]3 in advance. Sterically hindered carboxylic acids also give the corresponding Weinreb amides in excellent yields. Various functional groups are tolerated on the carboxylic acid. The method, which is a simple process and gives high yields, is suitable for large-scale production. Georg Thieme Verlag KG Stuttgart · New York.

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METHOD FOR PRODUCING N,N -DIALKOXY-N,N -DIALKYL OXAMIDE

The present invention provides a process for preparing an N,N'-dialkoxy-N,N'-dialkyl oxamide represented by the formula (3) : wherein R2 and R3 may be the same or different from each other, and each represent an alkyl group having 1 to 4 carbon atoms, which comprises reacting an oxalic acid diester represented by the formula (1): wherein R1 and R1' may be the same or different from each other, and each represent a hydrocarbon group, and an N-alkyl-O-alkylhydroxylamine represented by the formula (2): ????????R2O-NHR3?????(2) wherein R2 and R3 have the same meanings as defined above, or an acid salt thereof in the presence of a base.

Synthesis of leprapinic acid, calycine and analogues by sequential "[3+2] cyclization/suzuki/lactonization" reactions

Calycine and analogues were prepared on the basis of Suzuki cross-coupling reactions of γ-alkylidene-α-hydroxybutenolides - readily available by cyclization of 1,3-dicarbonyl dianions or 1,3-bis(silyl enol ether)s with oxalyl derivatives - and subsequent boron tribromide-mediated lactonization. Leprapinic acid was prepared by chemoselective boron tribromide-mediated deprotection of permethylated leprapinic acid. Wiley-VCH Verlag GmbH & Co. KGaA, 2005.

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α-Keto Amides and 1,2-Diketones from N,N'-Dimethoxy-N,N'-dimethylethanediamide. A Synthetic and Mechanistic Investigation

N,N'-Dimethoxy-N,N'-dimethylethanediamide (1), a 1,2-dicarbonyl synthon prepared from oxalyl chloride, undergoes nucleophilic displacements with Grignard reagents to provide α-keto amides 2-12 in 28-90percent yields.The synthon also undergoes double nucleophilic displacements with organolithium reagents to furnish symmetrical 1,2-diketones 15-23 in 15-84percent yields.A mechanism accounting for all the products from the reaction of 1 with nucleophiles has been proposed.Several control experiments were carried out to support the proposed mechanism.