[ CAS No. 5437-67-2 ]

Name: 5437-67-2|Dimethyl 2-nitromalonate|98%
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Quality Control of [ 5437-67-2 ]

COA NMR CNMR HPLC LC-MS

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Alternatived Products of [ 5437-67-2 ]

Product Details of [ 5437-67-2 ]

CAS No. :	5437-67-2	MDL No. :	MFCD00010228
Formula :	C₅H₇NO₆	Boiling Point :	282.2°C at 760 mmHg
Linear Structure Formula :	-	InChI Key :	N/A
M.W :	177.11	Pubchem ID :	-
Synonyms :

Computed Properties of [ 5437-67-2 ]

TPSA :Topological Polar Surface Area	-	H-Bond Acceptor Count :	-
XLogP3 :	-	H-Bond Donor Count :	-
SP3 :	-	Rotatable Bond Count :	-

Safety of [ 5437-67-2 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 5437-67-2 ]

Upstream synthesis route of [ 5437-67-2 ]
Downstream synthetic route of [ 5437-67-2 ]

[ 5437-67-2 ] Synthesis Path-Upstream 1~1

1
[ 5437-67-2 ]
[ 536-74-3 ]
[ 51677-09-9 ]

Reference： [1] Bulletin of the Chemical Society of Japan, 1985, vol. 58, # 9, p. 2519 - 2522

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Yield	Reaction Conditions	Operation in experiment
76.5%	With nitric acid at 5 - 10℃; for 6h; Industrial scale;	1 Example 1 A 50 L glass reactor was charged with 10.0 kg (75.69 mol) of dimethyl malonate,Turn on stirringUnder the ice water bath control temperature about 10 ,Slowly add fuming nitric acid 9.54kg.After the addition was completed, the reaction was continued at a temperature of 5-10 ° C for 6 hours.Add salt water 20L, release the solution and move to 100L reactor,Ethyl acetate 20L was added, stirred for 10 minutes and allowed to stand for delamination.The ethyl acetate layer was washed twice with 10% sodium carbonate 20 and then with distilled water until the pH was 7,The ethyl acetate layer was dried over anhydrous sodium sulfate and the ethyl acetate was evaporated.A 98-102 ° C fraction (1 mmHg) was collected,10.26 kg of dimethyl 2-nitromalonate was obtained,Moore yield 76.5%.
	With nitric acid Darst_.;
	With nitric acid

Yield	Reaction Conditions	Operation in experiment
34.1%	In toluene at 170℃; for 2.5h; Microwave irradiation;	3.3-A Example 3; l-(4-(5-(4-Butyl-5-phenylisoxazol-3-yl)-l,2,4-oxadiazol-3-yl)benzyl)-azetidine-3- carboxylic acid; 3-A. Methyl 4-butyl-5-phenylisoxazole-3-carboxylate; [00151] A solution of hex-1-ynylbenzene (0.274 mL, 1.56 mmol), dimethyl 2- nitromalonate (0.421 mL, 3.12 mmol), 1 -butyl-3 - methylimidazoliumhexafluorophosphate (0.032 mL, 0.156 mmol) in toluene (6 mL) was subjected to the microwave at 170 0C for 150 min. The reaction mixture was concentrated under reduced pressure, and the residue was purified by flash silica gel chromatography using 5% ethyl acetate in hexane to give methyl 4-butyl-5- phenylisoxazole-3-carboxylate (0.142 g, 0.531 mmol, 34.1 % yield) as a clear, colorless oil. The product was 97% pure by HPLC with a ret. time = 3.11 min. - Column: CHROMOLITH SpeedROD 4.6 x 50 mm (4 min.); Solvent A = 10% MeOH, 90% H2O, 0.1% TFA; Solvent B = 90% MeOH, 10% H2O, 0.1% TFA.LC/MS M+1 = 260.2.
34%	With 3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate In toluene at 170℃; for 2.5h; Microwave irradiation; Inert atmosphere;

Yield	Reaction Conditions	Operation in experiment
30.2%	In toluene at 170℃; for 8.83333h; Microwave irradiation;	4.4-A Example 4; l-(4-(5-(4-Isobutyl-5-phenylisoxazol-3-yl)-l,2,4-oxadiazol-3-yl)benzyl)-azetidine-3- carboxylic acid; 4-A. Methyl 4-isobutyl-5-phenylisoxazole-3-carboxylate; [00155] A solution of (4-methylpent-l-ynyl)benzene (0.247 g, 1.56 mmol), dimethyl 2-nitromalonate (0.421 mL, 3.12 mmol), l-butyl-3- methylimidazoliumhexafluorophosphate (0.032 mL, 0.156 mmol) in toluene (5 mL) was subjected to the microwave at 1700C for 150 min. By HPLC, the reaction was-40-50% complete and resubjected to the microwave conditions for 360 min.(1700C). The toluene was decanted off leaving a dark gum which was triturated several times with ethyl acetate. The combined organic layers were concentrated under reduced pressure. The residue was purified by flash silica gel chromatography using 5% ethyl acetate in hexane to give methyl 4-isobutyl-5-phenylisoxazole-3- carboxylate (0.122 g, 0.470 mmol, 30.2 % yield) as a clear, colorless oil. The compound had an HPLC ret. time = 2.96 min. - Column: CHROMOLITHSpeedROD 4.6 x 50 mm (4 min.); Solvent A = 10% MeOH, 90% H2O, 0.1% TFA;Solvent B = 90% MeOH, 10% H2O, 0.1% TFA. LC/MS M+1 = 259.9. 1H NMR (500 MHz, chloroform-d) δ ppm 0.88 (s, 3H), 0.89 (s, 3H), 1.89 (dt, J=13.75, 6.87 Hz,IH), 2.80 (d, J=7.15 Hz, 2 H), 4.00 (s, 3H), 7.45 - 7.53 (m, 3H), 7.73 (d, J=6.60 Hz,2H).
30%	With 3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate In toluene at 170℃; Microwave irradiation; Inert atmosphere;

Yield	Reaction Conditions	Operation in experiment
	Stage #1: dimethyl 2-nitromalonate; 2-methyl-4-octyne In toluene at 170℃; for 1h; Microwave irradiation; Stage #2: With lithium hydroxide monohydrate; water In methanol at 20℃; Stage #3: With hydrogenchloride In water	18.18-B; 18.18C 18-B. Methyl 5-isobutyl-4-propylisoxazole-3-carboxylate and methyl 4-isobutyl-5- propylisoxazole-3-carboxylate; [00227] A mixture of 6-methylhept-3-yne (220 mg, 2 mmol), dimethyl 2- nitromalonate (567 mg, 3.20 mmol) and l-butyl-3-methylimidazolium hexafluorophosphate (0.04 ml, 0.2 mmol) in toluene (4 mL) was heated to 170°C in the microwave for 1 hr. After cooling to rt, the reaction mixture was partitioned between EtOAc (50 ml) and water (50 ml). The organic layer was washed with brine, dried (MgSO4) and concentrated to afford an orange oil that was chromatographed on a 12 gm Isco silica gel cartridge, eluting with a 0-5%EtO Ac/Hex gradient. The fractions which contained product were concentrated to afford 228 mg, 54. % yield of a mixture of methyl 4-ethyl-5-isobutylisoxazole-3-carboxylate and methyl 5-ethyl-4- isobutylisoxazole-3-carboxylate as light yellow oil. HPLC retention time = 1.86 minutes (YMC Combi 4.6 x 30 mm S-5 ODS column) eluting with 10-90% aqueous methanol + 0.1 TFA a 2minute gradient. MS:(M+H)= 226.22. 1H NMR indicates a ~1 : 1 mixture of regioisomers. These isomers were not readily separable by normal or reverse phase chromatography and this material was used without further purification in the next step.; 18.C 5-Isobutyl-4-propylisoxazole-3-carboxylic acid and 4-isobutyl-5- propylisoxazole-3 -carboxylic acid; [00228] To a mixture of methyl 5-isobutyl-4-propylisoxazole-3-carboxylate and methyl 4-isobutyl-5-propylisoxazole-3-carboxylate (164 mg, 0.728 mmol) in MeOH- I l l - (8 mL) and water (2 mL) was added LiOH, hydrate (15.28 mg, 0.364 mmol) and the mixture was allowed to stir overnight at rt. An additional amount of LiOH, hydrate (15.28 mg, 0.364 mmol) was added and the reaction mixture was stirred at rt for 2 hr. The MeOH was removed in vacuo and the remaining aqueous was acidified to pH ~1 with IN HCl. The mixture was extracted with EtOAc (20 mL). The organic layer was washed with brine (20 mL), dried (MgSO4) and concentrated to afford (144 mg, 0.682 mmol, 94 % yield) of product which was approximately a 1 : 1 mixture of 5- isobutyl-4-propylisoxazole-3-carboxylic acid and 4-isobutyl-5-propylisoxazole-3- carboxylic acid as a light yellow oil. HPLC retention time = 1.72 minutes (YMC Combi 4.6 x 30 mm S-5 ODS column) eluting with 10-90% aqueous methanol + 0.1 TFA a 2minute gradient. MS :(M+H)= 212.20.[00229] 1H NMR indicates a ~1 : 1 mixture of regioisomers as shown in the schematic above. These isomers were not readily separable by normal or reverse phase chromatography and this material was used without further purification in the next step.
	Stage #1: dimethyl 2-nitromalonate; 2-methyl-4-octyne With 3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate In toluene at 170℃; for 1h; Microwave irradiation; Inert atmosphere; Stage #2: With lithium hydroxide monohydrate; water In methanol at 20℃; Overall yield = 144 mg;

[ CAS No. 5437-67-2 ]

Quality Control of [ 5437-67-2 ]

Related Doc. of [ 5437-67-2 ]

Product Details of [ 5437-67-2 ]

Computed Properties of [ 5437-67-2 ]

Safety of [ 5437-67-2 ]

Application In Synthesis of [ 5437-67-2 ]

[ 5437-67-2 ] Synthesis Path-Upstream 1~1

[ 5437-67-2 ] Synthesis Path-Downstream 1~7