4637-24-5

Basic information

• Product Name: N,N-Dimethylformamide dimethyl acetal
• Synonyms: 1,1-dimethoxy-n,n-dimethyl-methanamin;Dimethoxy(dimethylamino)methane;Dimethoxy-N,N-dimethylmethanamine;N-(Dimethoxymethyl)dimethylamine;N,N-Dimethylfirmanmidedimethylacetal;Trimethylamine, 1,1-dimethoxy-;N,N-DIMETHYLDIMETHOXYMETHYLAMINE;N,N-DIMETHYLFORMAMIDE DIMETHYL ACETAL
• CAS NO: 4637-24-5
• Molecular Formula: C₅H₁₃NO₂
• Molecular Weight: 119.16
• EINECS: 225-063-3
• Product Categories: blocks;BuildingBlocks;Aliphatics;(intermediate of zaleplon);Biochemistry;Nucleosides, Nucleotides & Related Reagents;Protecting Agents for Hydroxyl and Amino Groups;Protecting Agents, Phosphorylating Agents & Condensing Agents;Analytical Chemistry;Esterification & Alkylation (GC Derivatizing Reagents);GC Derivatizing Reagents;N,N-Dimethylformamide Dialkylacetals (GC Derivatizing Reagents)
• Mol File: 4637-24-5.mol
• Article Data: 16

Chemical Properties

• Melting Point: -85°C
• Boiling Point: 102-103 °C720 mm Hg(lit.)
• Flash Point: 45 °F
• Appearance: White to off-white/Solid
• Density: 0.897 g/mL at 25 °C(lit.)
• Vapor Pressure: 31.1mmHg at 25°C
• Refractive Index: n20/D 1.396(lit.)
• Storage Temp.: Flammables area
• Solubility: Miscible with most organic solvents.
• PKA: 5.00±0.50(Predicted)
• Explosive Limit: 1.3-17.7%(V)
• Water Solubility: hydrolysis
• Sensitive: Moisture Sensitive
• BRN: 506020
• CAS DataBase Reference: N,N-Dimethylformamide dimethyl acetal(CAS DataBase Reference)
• NIST Chemistry Reference: N,N-Dimethylformamide dimethyl acetal(4637-24-5)
• EPA Substance Registry System: N,N-Dimethylformamide dimethyl acetal(4637-24-5)

Safety Data

• Hazard Codes: F,Xn,Xi
• Statements: 11-22-36/37/38-36/38-20-20/21/22-10-52
• Safety Statements: 16-26-36/37-36/37/39-33-29-7/9
• RIDADR: UN 3271 3/PG 2
• WGK Germany: 1
• F: 21
• TSCA: Yes
• HazardClass: 3
• PackingGroup: II
• Hazardous Substances Data: 4637-24-5(Hazardous Substances Data)

Usage

Chemical Properties

clear colourless liquid

Uses

Different sources of media describe the Uses of 4637-24-5 differently. You can refer to the following data:
1. 1,1-Dimethoxy-N,N-dimethylmethanamine is used as a reagent in the formation of pyridine derivatives that exhibit inhibition against PI3 kinase p110α enzymes.
2. N,N-Dimethylformamide dimethyl acetal is used as an intermediate in the formation of pyridine derivatives, which exhibits inhibition against PI3 kinase p110alfa enzymes. It is utilized for the derivatization of primary sulfonamides and trifluoroacetic acid. It is also used in the preparation of formamidine derivatives. It is used as a reagent for n-dimethylaminomethylene and methyl esters. Further, it is used to catalyze the coupling of epoxides with carbon dioxide to prepare cyclic carbonates.
3. Used to catalyze the coupling of epoxides with carbon dioxide under solvent free conditions leading to cyclic carbonates.

Definition

ChEBI: An acetal obtained by formal condensation of N,N-dimethylformamide with methanol. N,N-dimethylformamide dimethyl acetal is a derivatisation agent used in gas-chromatography applica ions

General Description

Esterate M (N,N-Dimethylformamide dimethyl acetal, DMFDMA) is an methylating reagent. It has been used in methyl esterification of carboxylic acid and also in one-step derivatization of amino acids into N,N-Dimethylaminomethylene methyl esters.

Flammability and Explosibility

Highlyflammable

InChI:InChI=1/C5H13NO2/c1-6(2)5(7-3)8-4/h5H,1-4H3/p+1

Synthetic route

sodium methylate (124-41-4) + N,N-dimethyl-formamide (68-12-2, 33513-42-7) → N,N-dimethyl-formamide dimethyl acetal (4637-24-5)

Conditions	Yield
Stage #1: N,N-dimethyl-formamide With dimethyl sulfate at 20 - 70℃; for 4h; Stage #2: sodium methylate at 25℃; for 2h; Temperature;	85.4%

dimethyl amine (124-40-3) + trimethyl orthoformate (149-73-5) → N,N-dimethyl-formamide dimethyl acetal (4637-24-5)

Conditions	Yield
With acetyl chloride at 20℃; for 12h; Inert atmosphere;	95%

C14H21NO3 (1196967-42-6) + C31H32N4O9S (1196967-61-9) → N,N-dimethyl-formamide dimethyl acetal (4637-24-5)

Conditions	Yield
With sulfuric acid In 1,4-dioxane; water at 0℃; for 6h; Inert atmosphere;	80%

(methoxymethylidene)dimethylammonium methyl sulfate (21511-55-7, 34643-89-5) → N,N-dimethyl-formamide dimethyl acetal (4637-24-5)

Conditions	Yield
With methanol; sodium methylate at 0 - 20℃; for 20h; Inert atmosphere;	59%

chloro-dimethoxy-methane (52117-32-5) + dimethyl amine (124-40-3) → N,N-dimethyl-formamide dimethyl acetal (4637-24-5)

Conditions	Yield
at 140 - 150℃; for 2h; Green chemistry;	86.8%

N,N-dimethyl-formamide (68-12-2, 33513-42-7) + dimethyl sulfate (77-78-1) → N,N-dimethyl-formamide dimethyl acetal (4637-24-5)

Conditions	Yield
With nitrogen at 80℃; for 2h;	100%
With sodium 1.) 3 h, 60-80 degC: 2.) 0 degC, methanol; Yield given. Multistep reaction;
at 60℃; for 3h;

sodium methylate (124-41-4) + (methoxymethylidene)dimethylammonium methyl sulfate (21511-55-7, 34643-89-5) → N,N-dimethyl-formamide dimethyl acetal (4637-24-5)

Conditions	Yield
In Petroleum ether at 0℃; for 2h;

1-(2-furyl)-1-ethanone (1192-62-7) → N,N-dimethyl-formamide dimethyl acetal (4637-24-5) + (2E)-3-(dimethylamino)-1-furan-2-ylprop-2-en-1-one (109482-86-2)

methyl-3-pyridylketone (350-03-8) → (E)-3-(dimethylamino)-1-(pyridin-3-yl)prop-2-en-1-one (55314-16-4, 75415-01-9, 123367-26-0) + N,N-dimethyl-formamide dimethyl acetal (4637-24-5)

N,N-dimethyl-formamide (68-12-2, 33513-42-7) + 2-butyl-2-imidazolin-5-one (154147-42-9) → N,N-dimethyl-formamide dimethyl acetal (4637-24-5)

Conditions	Yield
With trichlorophosphate at 40℃; Condensation;

sodium methylate (124-41-4) + N,N,N',N'-Tetramethylformamidinium chloride (1071-38-1) → bis(dimethylamino)methoxymethane (1186-70-5) + tris(dimethylamino)methane (5762-56-1) + N,N-dimethyl-formamide dimethyl acetal (4637-24-5)

Conditions	Yield
In tetrahydrofuran at 21℃; Title compound not separated from byproducts.;

chloroform (67-66-3) + sodium methylate (124-41-4) → N,N-dimethyl-formamide dimethyl acetal (4637-24-5) + trimethyl orthoformate (149-73-5)

Conditions	Yield
With N,N-dimethyl-formamide In methanol	A 48 % Chromat. B 38 % Chromat.

chloroform (67-66-3) + sodium methylate (124-41-4) + N,N-dimethyl-formamide (68-12-2, 33513-42-7) → N,N-dimethyl-formamide dimethyl acetal (4637-24-5) + trimethyl orthoformate (149-73-5)

Conditions	Yield
	A 91 % Chromat. B 3 % Chromat.

chloroform (67-66-3) + sodium methylate (124-41-4) + N,N-dimethyl-formamide (68-12-2, 33513-42-7) → carbon monoxide (201230-82-2) + N,N-dimethyl-formamide dimethyl acetal (4637-24-5) + trimethyl orthoformate (149-73-5)

Conditions	Yield
for 0.5h; Mechanism; methanol presence;

5-methyl-1,3,4-thiadiazol-2-amine (108-33-8) + N,N-dimethyl-formamide dimethyl acetal (4637-24-5) → 2-(N,N-dimethylaminomethyleneamino)-5-methyl-1,3,4-thiadiazole (41077-44-5)

Conditions	Yield
In toluene for 2h; Heating;	100%
In ethanol Heating;

N,N-dimethyl-formamide dimethyl acetal (4637-24-5) + ethyl isopropylidenecyanoacetate (759-58-0) → 1-carbethoxy-1-cyano-2-methyl-4-dimethylamino-1,4-butadiene (65996-11-4)

Conditions	Yield
In ethanol for 24h; Heating / reflux;	100%
In ethanol for 24h; Reflux;	74%
In ethanol

2-aminopyridine (504-29-0) + N,N-dimethyl-formamide dimethyl acetal (4637-24-5) → N,N-dimethyl-N'-pyridin-2-yl-formamidine (17175-39-2)

Conditions	Yield
at 150℃; for 0.116667h; Microwave;	100%
In methanol at 70℃; for 15h;	81%
for 6h; Reflux;	71%

2-aminopyrimidine (109-12-6) + N,N-dimethyl-formamide dimethyl acetal (4637-24-5) → N,N-dimethyl-N'-pyrimidin-2-ylformamidine (6578-34-3)

Conditions	Yield
In toluene Heating;	100%
for 6h; Reflux;	80%
In toluene for 2h; Heating;

6-chloro-pyridazin-3-ylamine (5469-69-2) + N,N-dimethyl-formamide dimethyl acetal (4637-24-5) → N'-(6-chloropyridazin-3-yl)-N,N-dimethylmethanimidamide (35053-55-5)

Conditions	Yield
at 105℃; for 2h;	100%
for 2h; Reflux;	81%
for 2h; Reflux;	81%

2-methyl-3-nitropyridine (18699-87-1) + N,N-dimethyl-formamide dimethyl acetal (4637-24-5) → 2-(3-nitro-2-pyridinyl)-N,N-dimethyletheneamine (65156-92-5)

Conditions	Yield
	100%
In N,N-dimethyl-formamide at 90℃; for 4h; Inert atmosphere;	73%
In N,N-dimethyl-formamide at 115℃;
In N,N-dimethyl-formamide at 120℃; for 17h;

6-nitrophthalide (610-93-5) + N,N-dimethyl-formamide dimethyl acetal (4637-24-5) → 3-dimethylaminomethylene-6-nitroisobenzofuran-1(3H)-one

Conditions	Yield
With potassium tert-butylate for 0.0833333h; Heating;	100%

isobutylamine (78-81-9) + N,N-dimethyl-formamide dimethyl acetal (4637-24-5) → N2-iso-butyl-N1,N1-dimethylformamidine (67161-18-6)

Conditions	Yield
at 60℃;	100%

ethyl acetoacetate (141-97-9) + N,N-dimethyl-formamide dimethyl acetal (4637-24-5) → ethyl 2-[(dimethylamino)methylene]-3-oxobutanoate (134653-70-6, 51145-57-4)

Conditions	Yield
at 20℃;	100%
at 20℃;	100%
at 20℃;	100%

1,3-cylohexanedione (504-02-9) + N,N-dimethyl-formamide dimethyl acetal (4637-24-5) → 2-(dimethylaminomethylene)cyclohexane-1,3-dione (85302-07-4)

Conditions	Yield
for 1h; Heating;	100%
at 100℃; for 1h;	100%
at 95℃; for 1h;	100%

ethyl 3-oxo-3-phenylpropionate (94-02-0) + N,N-dimethyl-formamide dimethyl acetal (4637-24-5) → ethyl-3-(dimethylamino)-2-(phenylcarbonyl)prop-2-enoate (66129-60-0)

Conditions	Yield
at 110℃; for 0.666667h; Microwave irradiation;	100%
for 1h; Heating;	94%
In toluene at 60℃; for 24h;	92%

cyclohexylamine (108-91-8) + N,N-dimethyl-formamide dimethyl acetal (4637-24-5) → N,N-dimethyl-N'-cyclohexylformamidine (3459-75-4)

Conditions	Yield
at 60℃;	100%
In methanol at 25℃; for 12h;	98%
1.) 50 deg C, 5 h, 2.) room temperature, 12 h;	92%
In benzene for 1h; Heating;	64%

dimedone (126-81-8) + N,N-dimethyl-formamide dimethyl acetal (4637-24-5) → 2-dimethylaminomethylene-5,5-dimethylcyclohexane-1,3-dione (75039-59-7)

Conditions	Yield
for 1h; Heating;	100%
In 5,5-dimethyl-1,3-cyclohexadiene for 3h; Reflux;	100%
at 100℃; for 1h;	100%

propylamine (107-10-8) + N,N-dimethyl-formamide dimethyl acetal (4637-24-5) → N2-n-propyl-N1,N1-dimethylformamidine (32150-25-7)

Conditions	Yield
at 60℃;	100%

5-phenyl-cyclohexane-1,3-dione (493-72-1) + N,N-dimethyl-formamide dimethyl acetal (4637-24-5) → 2-((dimethylamino)methylene)-5-phenyl-cyclohexane-1,3-dione (85302-08-5)

Conditions	Yield
for 2h; Reflux;	100%
at 100℃; for 1h;	100%
for 1h; Heating;	98%

3',5'-O-1,1,3,3-tetraisopropyldisiloxan-1,3-diyl-guanosine (69304-44-5) + N,N-dimethyl-formamide dimethyl acetal (4637-24-5) → 2-N-(Dimethylaminomethylene)-3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)guanosine (120853-22-7)

Conditions	Yield
In N,N-dimethyl-formamide for 20h; Ambient temperature;	100%
In N,N-dimethyl-formamide at 20℃; for 6h;	84%

acetonedicarboxylic acid (542-05-2) + N,N-dimethyl-formamide dimethyl acetal (4637-24-5) → 1,5-bis(dimethylamino)-1,4-pentadien-3-one (25299-40-5)

Conditions	Yield
at 70℃; for 1h;	100%

3-(trifluoromethyl)phenylacetone (21906-39-8) + N,N-dimethyl-formamide dimethyl acetal (4637-24-5) → 1-dimethylamino-2-(m-trifluoromethylphenyl)-1-buten-3-one (67382-34-7, 72833-79-5)

Conditions	Yield
for 12h; Heating;	100%

hexan-1-amine (111-26-2) + N,N-dimethyl-formamide dimethyl acetal (4637-24-5) → N2-n-hexyl-N1,N1-dimethylformamidine (85599-94-6)

Conditions	Yield
at 60℃;	100%

4-methoxyacetoacetic acid methylester (41051-15-4) + N,N-dimethyl-formamide dimethyl acetal (4637-24-5) → methyl 2-[(dimethylamino)methylene]-4-methoxy-3-oxobutanoate (127958-23-0)

Conditions	Yield
at 20℃; for 24h;	100%
at 20℃; for 24h;	100%
In N,N-dimethyl-formamide at 120℃; for 0.5h; Inert atmosphere; microwave irradiation;	97%

diethyl (2-oxobutyl)phosphonate (1067-73-8) + N,N-dimethyl-formamide dimethyl acetal (4637-24-5) → {1-[1-Dimethylamino-meth-(Z)-ylidene]-2-oxo-butyl}-phosphonic acid diethyl ester (98934-29-3)

Conditions	Yield
With calcium chloride for 2h; Heating;	100%

diethyl (2-ethoxycarbonyl)-2-oxoethylphosphonate (66187-85-7) + N,N-dimethyl-formamide dimethyl acetal (4637-24-5) → (Z)-3-(Diethoxy-phosphoryl)-4-dimethylamino-2-oxo-but-3-enoic acid ethyl ester (98934-35-1)

Conditions	Yield
With calcium chloride Ambient temperature;	100%

benzyl acetoacetate (5396-89-4) + N,N-dimethyl-formamide dimethyl acetal (4637-24-5) → benzyl 2-((dimethylamino)methylene)-3-oxobutanoate (93552-75-1)

Conditions	Yield
at 20℃;	100%
at 20℃;	100%
In toluene at 20℃; for 16h;	100%

2,6-dinitrotoluene (606-20-2) + N,N-dimethyl-formamide dimethyl acetal (4637-24-5) → 3-nitro-trans-2-[β-(dimethylamino)vinyl]-nitrobenzene (78283-21-3)

Conditions	Yield
In N,N-dimethyl-formamide for 4h; Heating;	100%
In N,N-dimethyl-formamide at 115℃; for 6h;	96%
With copper(l) iodide; N,N-dimethyl-formamide at 180℃; under 6000.6 - 7500.75 Torr; for 0.166667h; microwave irradiation;	85%

tryptamine hydochloride (343-94-2) + N,N-dimethyl-formamide dimethyl acetal (4637-24-5) → N'-[2-(1H-Indol-3-yl)-ethyl]-N,N-dimethyl-formamidine

Conditions	Yield
for 21h; Heating;	100%

1-methyl-2'-deoxy-5'-O-tritylpseudouridine (78064-64-9) + N,N-dimethyl-formamide dimethyl acetal (4637-24-5) → 1,3-Dimethyl-2'-deoxy-5'-O-tritylpseudouridine (78064-66-1)

Conditions	Yield
at 95 - 100℃; for 2h;	100%

ethyl 3-(2,3,4,5-tetrafkuorophenyl)-3-oxopropanoate (94695-50-8) + N,N-dimethyl-formamide dimethyl acetal (4637-24-5) → ethyl α<(N,N-dimethylamino)methylene>-2,3,4,5-tetrafluoro-β-oxobenzenepropanoate (138998-47-7)

Conditions	Yield
With acetic anhydride for 0.5h;	100%
In toluene at 115 - 120℃; for 1h;	91%

2'-O-methyl-5'-O-(dimethoxytrityl)pseudoisocytidine (133648-45-0) + N,N-dimethyl-formamide dimethyl acetal (4637-24-5) → N2-<(dimethylamino)methylene>-2'-O-methyl-5'-O-(dimethoxytrityl)pseudoisocytidine (141437-72-1)

Conditions	Yield
In N,N-dimethyl-formamide for 5h; Ambient temperature;	100%

Methyl 2-oxo-3-phenylthiopropionate (115413-26-8) + N,N-dimethyl-formamide dimethyl acetal (4637-24-5) → Methyl 4-dimethylamino-2-oxo-3-phenylthio-3-butenoate (115412-99-2)

Conditions	Yield
In toluene for 1.5h; Ambient temperature;	100%

1-Phenylsulfanyl-3-(2,2,2-trichloro-ethoxy)-propan-2-one (115413-21-3) + N,N-dimethyl-formamide dimethyl acetal (4637-24-5) → (Z)-4-Dimethylamino-3-phenylsulfanyl-1-(2,2,2-trichloro-ethoxy)-but-3-en-2-one (115413-30-4)

Conditions	Yield
at 70℃; for 1.5h;	100%

Upstream product

• 67-66-3 chloroform 
• 124-41-4 sodium methylate 
• 68-12-2 N,N-dimethyl-formamide 
• 1196967-42-6 C₁₄H₂₁NO₃ 
• 1196967-61-9 C₃₁H₃₂N₄O₉S 
• 350-03-8 methyl-3-pyridylketone 
• 1192-62-7 1-(2-furyl)-1-ethanone 
• 1071-38-1 N,N,N',N'-Tetramethylformamidinium chloride 
• 154147-42-9 2-butyl-2-imidazolin-5-one 
• 77-78-1 dimethyl sulfate 
• 124-40-3 dimethyl amine 
• 149-73-5 trimethyl orthoformate 
• 21511-55-7 (methoxymethylidene)dimethylammonium methyl sulfate 
• 52117-32-5 chloro-dimethoxy-methane 

Downstream Products

• 18876-89-6 N¹,N¹-dimethyl-N²-(thiazol-2-yl)formamidine 
• 64189-05-5 2-Amino-3-(1',3','-oxadiazolyl-5')pyridin 
• 56951-47-4 N,N-dimethyl-N'-(5-nitro-[1,3,4]thiadiazol-2-yl)-formamidine 
• 63285-46-1 3-(dimethylamino)-1-(10H-phenothiazin-2-yl)prop-2-en-1-one 
• 18805-23-7 N-(Phenyl)imidodithiokohlensaeure-S,S'-dimethylester 
• 19758-78-2 Phenylimino-methylmercapto-N,N-dimethylacetamid 
• 13997-51-8 dimethyl N-phenylimidocarbonate 
• 18805-28-2 O,S-dimethyl phenylcarbonimidothioate 
• 25770-53-0 N-tosyl-N',N'-dimethylformamidine 
• 17059-74-4 3-(Dimethylamino)-1,2-diphenyl-2-propen-1-on 
• 65691-99-8 N,N-dimethyl-N'-(5-phenyl-[1,3,4]selenadiazol-2-yl)-formamidine 
• 6006-65-1 N,N-dimethylformamide dipropyl acetal 
• 51559-52-5 2-dimethylaminomethylene-3-oxo-butyric acid methyl ester 
• 66606-23-3 1-(dimethylamino)-2-phenylpent-1-en-3-one 

Relevant articles and documents

Method for synthesizing 2-amino-5-nitrothiazole

The invention discloses a method for synthesizing 2-amino-5-nitrothiazole, which comprises the following steps: (1) in an inert atmosphere, adding diethylamine, acetyl chloride and triethyl orthoacetate into a reaction container, uniformly mixing, stirring to react for 12-24 hours, and distilling and purifying the reaction product to obtain N, N-dimethylformamide dimethyl acetal, (2) in an inert atmosphere, mixing N, N-dimethylformamide dimethyl acetal with nitromethane, heating the mixture to 80-100 DEG C for reflux reaction, carrying out reduced pressure distillation on the reaction productto remove the solvent, and purifying to obtain N, N-dimethyl nitroethylene, and (3) in an inert atmosphere, putting N, N-dimethyl nitroethylene into a reaction container, sequentially adding ethanol,liquid bromine and thiourea, reacting at room temperature, after the reaction is finished, filtering a reactant, washing with ice ethanol, drying to obtain a white solid, adding water, and filtering to obtain the 2-amino-5-nitrothiazole. According to the method for synthesizing 2-amino-5-nitrothiazole, the raw materials are easy to obtain, the cost is low, and the yield can reach 60%.

Preparation method of azoxystrobin intermediate

The invention relates to a preparation method of an azoxystrobin intermediate. According to the method, a compound shown in a formula (II) serves as a raw material and reacts with a methylating agentunder a basic condition to obtain the azoxystrobin intermediate shown in a formula (I), wherein Z1 represents halogen. The method has the advantages that the reaction time is short, the total yield ishigh, the cost of raw materials is low, and the method is suitable for large-scale production and has very important significance for industrial production of final products of azoxystrobin. The formula (II) and the formula (I) are shown in the description.

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