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Chemical Structure| 5952-93-2 Chemical Structure| 5952-93-2

Structure of 5952-93-2

Chemical Structure| 5952-93-2

Methyl 1-methyl-1H-pyrazole-4-carboxylate

CAS No.: 5952-93-2

4.5 *For Research Use Only !

Cat. No.: A184464 Purity: 98%

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Product Details of [ 5952-93-2 ]

CAS No. :5952-93-2
Formula : C6H8N2O2
M.W : 140.14
SMILES Code : O=C(C1=CN(C)N=C1)OC
MDL No. :MFCD11053755
InChI Key :HGQQQXMARFJNCP-UHFFFAOYSA-N
Pubchem ID :10130004

Safety of [ 5952-93-2 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H332-H335
Precautionary Statements:P261-P280-P305+P351+P338

Application In Synthesis of [ 5952-93-2 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 5952-93-2 ]

[ 5952-93-2 ] Synthesis Path-Downstream   1~31

  • 1
  • [ 110860-60-1 ]
  • [ 88398-85-0 ]
  • [ 5952-93-2 ]
  • 3
  • [ 5952-93-2 ]
  • [ 39806-90-1 ]
  • [ 34091-53-7 ]
  • [ 34091-52-6 ]
  • methyl ester of 3,5-diiodo-1-methylpyrazole-4-carboxylic acid [ No CAS ]
  • 4
  • [ 5952-93-2 ]
  • [ 88398-85-0 ]
  • [ 109056-69-1 ]
  • 5
  • methyl 3-amino-1-methylpyrazole-4-carboxylate [ No CAS ]
  • [ 5952-93-2 ]
  • [ 148934-66-1 ]
  • 6
  • [ 624-49-7 ]
  • [ 256658-45-4 ]
  • [ 78607-37-1 ]
  • [ 22050-80-2 ]
  • [ 5952-93-2 ]
YieldReaction ConditionsOperation in experiment
EXAMPLE 4 Methyl-1-methyl-4-pyrazole-carboxylate A stirred mixture of 1.12 g DI-water, 5.92 g concentrated aqueous HCl and 2.08 g NH2 -NHCH3 was cooled to 15 C. and 10.00 g 3,3-dimethoxy-2-dimethoxymethyl-propionate were fed within 5 minutes. The mixture was stirred at 15 C. to 20 C. for 2.0 hours and, afterwards, approximately two-thirds of the solvent was removed in vacuo. The precipitated crystalline product was removed by suction-filtration, washed with a small amount of ice water and subsequently dried in vacuo. By this means, 4.00 g (63% of theory based on 3,3-dimethoxy-2-dimethoxymethyl-propionate) methyl-1-methyl4-pyrazole-carboxylate could be isolated. Identification of the product was based on 1 H-NMR-, 13 C- and IR-spectra. The mother liquor still contained methyl-1-methyl-4-pyrazole-carboxylate.
With caesium carbonate; In acetonitrile; at 20℃;Cooling with ice; General procedure: To a mixture of 1H-pyrrole-3-carboxylic acid (1.0 g, 9.00 mmol) and cesium carbonate (1.58 mL, 19.80 mmol) in ACN (20 mL) colled in an ice bath, was added iodomethane (1.68 mL, 27.0 mmol). The resulting mixture was stirred at RT. The mixture was then filtered, and the solid was washed with EtOAc. The filtrate was concentrated and dried under reduced pressure to give methyl 1-methyl-1H-pyrrole-3-carboxylate (577 mg). LCMS- ESI (pos.): 140.1 (M+H)+.
  • 8
  • [ 5952-93-2 ]
  • [ 109056-69-1 ]
YieldReaction ConditionsOperation in experiment
94% With sulfuryl dichloride; In dichloromethane; at 20℃; for 12h; Sulphuryl chloride (14.4 mL,178.35 mmol) was added to a solution of compound 1 (5 g, 35.68 mmol) in dichloromethane (100 mL) and the resulting mixture was stirred at room temperature for 12 h. The reaction mixture was poured into saturated aqueous solution of sodium bicarbonate (40 mL) and extracted with dichloromethane (2 × 20 mL). The combined extracts were washed with brine solution (3 × 25 mL), dried over sodium sulphate (22 g), filtered and evaporated in vacuo to obtain the crude product. The crude compound was crystallized using cyclohexane (30 mL) to afford compound 1. White powder; Yield: 7 g, 94 %; m.p.: 58-59 C. 1H NMR (300 MHz, CDCl3): delta 3.85 (s, 3H, -OMe),3.82 (s, 3H, -NMe); ESI-MS: m/z, 209 (M+1)+.
  • 12
  • [ 5952-92-1 ]
  • [ 18107-18-1 ]
  • [ 5952-93-2 ]
YieldReaction ConditionsOperation in experiment
76% With methanol; In hexanes; at 0℃; for 0.333333h; [00263] Step A: (Trimethylsilyl)diazomethane (12.0 niL, 24 mmol, 2.0M solution in hexanes) was added dropwise via an addition funnel to a cold (O0C) solution of 1 -methyl- IH- pyrazole-4-carboxylic acid (0.59 g, 4.7 mmol) in MeOH (20 mL). The reaction mixture was stirred for 20 minutes and then concentrated. The crude product was partitioned between ethyl acetate (100 mL) and water (50 mL). The organics were dried, filtered and concentrated. The crude product was purified by flash chromatography, eluting with hexanes/ethyl acetate (4:1) to give methyl 1 -methyl- lH-pyrazole-4-carboxylate (0.50 g, 3.6 mmol, 76% yield) as a solid, m/z (APCI-pos) M+l = 141.1.
  • 14
  • [ 5952-93-2 ]
  • [ 170020-91-4 ]
YieldReaction ConditionsOperation in experiment
With hydrazine; In methanol; at 20℃; for 24h; General procedure: To a solution of methyl 1-(methylcarbamoyl)-1H-pyrazole-3- carboxylate, Example 395.1 (0.943 g, 5.15 mmol) in MeOH (10 mL, 247 mmol), was added hydrazine (0.236 mL, 10.30 mmol) at RT. The resulting mixture was stirred at RT for 24 h. The mixture was then concentrated in vacuo and the residue was dissolved in water (100 mL). The aqueous solution was lyophilized to give the title compound (943 mg). LCMS-ESI (pos.): 184.1 (M+H)+.
  • 18
  • [ 5952-93-2 ]
  • C18H18N6OS [ No CAS ]
  • 20
  • [ 39971-65-8 ]
  • [ 5952-93-2 ]
  • methyl 1-methyl-5-(trifluoromethyl)-1H-pyrazole-4-carboxylate [ No CAS ]
  • 21
  • 1-[bis(difluoroacetoxy)iodo]-3,5-di-tert-butylbenzene [ No CAS ]
  • [ 5952-93-2 ]
  • methyl-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylate [ No CAS ]
  • 22
  • [ 5952-93-2 ]
  • methyl 3-chloro-5-(chlorosulfonyl)-1-methyl-1H-pyrazole-4-carboxylate [ No CAS ]
  • 23
  • [ 5952-93-2 ]
  • (S)-benzyl-3-(((4-(methoxycarbonyl)-1-methyl-1H-pyrazol-5-yl)methyl)amino)-piperidine-1-carboxylate [ No CAS ]
  • 24
  • [ 5952-93-2 ]
  • (S)-5-(((1-((benzyloxy)carbonyl)piperidin-3-yl)amino)methyl)-1-methyl-1H-pyrazole-4-carboxylic acid [ No CAS ]
  • 25
  • [ 5952-93-2 ]
  • (S)-benzyl-3-(1-methyl-4-oxopyrrolo[3,4-c]pyrazol-5(1H,4H,6H)-yl)piperidine-1-carboxylate [ No CAS ]
  • 26
  • [ 5952-93-2 ]
  • (S)-1-methyl-5-(piperidin-3-yl)-5,6-dihydropyrrolo[3,4-c]pyrazol-4(1H)-one [ No CAS ]
  • 27
  • [ 5952-93-2 ]
  • 5-((S)-1-(((S)-2,3-dihydrobenzo[b][1,4]dioxin-2-yl)methyl)piperidin-3-yl)-1-methyl-5,6-dihydropyrrolo[3,4-c]pyrazol-4(1H)-one [ No CAS ]
  • 28
  • [ 68-12-2 ]
  • [ 5952-93-2 ]
  • methyl-5-formyl-1-methyl-1H-pyrazole-4-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
0.2 g To a stirred solution of LDA (2.0 M in THF) (10.7 mL, 21.42 mmol) in THF (10.0 mL) was added methyl 1-methyl- 1H-pyrazole-4-carboxylate (1.0 g, 7.14 mmol) in THF (10.0 mL) at -78 C slowly and stirred for 2 h. Dimethylformamide (2.5 mL, 32.84 mmol) was added to the reaction mixture at -78C and then allowed to stir at 0 C for 2 h. The reaction mixture was quenched with aqueous 1 M HC1 solution (10 mL) and extracted with EtOAc (3 x 10 mL). The combined organic extracts were dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. Crude product was purified with silica gel chromatography using20% EtOAc / petroleum ether to afford 0.200 g of methyl 5-formyl-i-methyl-1H-pyrazole-4- carboxylate as pale yellow solid.?H NMR (400 MHz, CDC13) oe ppm 3.91 (s, 3H), 4.20 (s, 3H), 7.91 (s, 1H), 10.50 (s, 1H).
  • 29
  • [ 5952-93-2 ]
  • [ 756-79-6 ]
  • dimethyl (2-(1-methyl-1H-pyrazol-4-yl)-2-oxoethyl)phosphonate [ No CAS ]
  • 30
  • [ 5952-93-2 ]
  • 2-(5H-imidazo[5,1-a]isoindol-5-yl)-1-(1-methyl-1H-pyrazol-4-yl)ethan-1-one [ No CAS ]
  • 31
  • [ 5952-93-2 ]
  • 2-(5H-imidazo[5,1-a]isoindol-5-yl)-1-(1-methyl-1H-pyrazol-4-yl)ethan-1-ol [ No CAS ]
 

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