[ CAS No. 2493-04-1 ]

Name: 2493-04-1|(5-Nitrofuran-2-yl)methanol|96%
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CAS No. :	2493-04-1	MDL No. :	MFCD00272267
Formula :	C₅H₅NO₄	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	N/A
M.W :	143.10 g/mol	Pubchem ID :	-
Synonyms :

Safety of [ 2493-04-1 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H312-H315-H319-H332-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 2493-04-1 ]

Upstream synthesis route of [ 2493-04-1 ]
Downstream synthetic route of [ 2493-04-1 ]

[ 2493-04-1 ] Synthesis Path-Upstream 1~2

1
[ 2493-04-1 ]
[ 698-63-5 ]

Yield	Reaction Conditions	Operation in experiment
90%	With manganese(IV) oxide In dichloromethane at 20℃; for 12 h;	The compound 4 (10 g, 0.07 µM) dissolved in 150 ml dichloromethane in, adding manganese dioxide (60.9 g, 0.7 µM), stirring at room temperature 12 h, filtering, drying by anhydrous magnesium sulphate, evaporate the solvent. Vacuum distillation, to obtain compound 5 (8.9 g, orange liquid, yield 90percent).

Reference： [1] Chemistry - A European Journal, 2010, vol. 16, # 42, p. 12718 - 12726
[2] Patent: CN108101874, 2018, A, . Location in patent: Paragraph 0006; 0017; 0020; 0023; 0026; 0028; 0031
[3] RSC Advances, 2014, vol. 4, # 25, p. 12834 - 12839
[4] Journal of the American Chemical Society, 1931, vol. 53, p. 1923
[5] Green Chemistry, 2017, vol. 19, # 5, p. 1315 - 1326

2
[ 2493-04-1 ]
[ 20782-91-6 ]

Yield	Reaction Conditions	Operation in experiment
84%	With 1,3,5-tribromo-hexahydro-<1,3,5>triazine-2,4,6-trione; triphenylphosphine In dichloromethane at 20℃; for 4 h;	To a stirred solutionof triphenyl phosphine (39.40 g, 150.24 mmol, 4.3 eq) in dichloromethane (200 mL) was added tribromoisocyanuric acid (14.05 g, 38.34 mmol, 1.5 eq). After 30 min, the alcohol(4) (5 g, 34.94 mmol, 1 eq) was added and the suspension was stirred at room temperature for 4 h. After completion of the reaction, the precipitated cyanuric acid was filtered off and the organic layer was washed with water (4 × 100 mL) followedby brine solution. The organic layer was dried over Na2SO4, filtered and evaporated under reduced pressure. The obtained residue was treated with n-hexane and filtered through a short column packed with silica gel (100-200 mesh). Evaporationof n-hexane gave the desired product 5. Yellow oily liquid; Yield: 6.33 g, 84 percent. IR (KBr, ν max , cm –1 ): 1526 and 1345 (NO2);1 H NMR (400 MHz, CDCl3) δ 4.49 (s, 2H), 6.64 (d, J = 4.0Hz, 1H, H 3 -furan), 7.28 (d, J = 4.0 Hz, 1H, H 4 -furan).
60%	With phosphorus tribromide In dichloromethane at 0 - 20℃; for 1 h;	To a stirred solution of A (928 mg, 6.50 mmol) in DCM (20m1), phosphorus tribromide (0.80 ml, 8.40 mmol) was added slowly at 0 °C and reaction mixture was stirred at room temperature for one hour. On completion, the reaction mixture was poured into crushed ice, neutralizedwith sodium bicarbonate solution and extracted with DCM,which on evaporation obtain the compoundB (800 mg) in 60percent isolated yield. 1H NMR (CDC13): 37.29 (d, 1H, JAB= 3.5 Hz, ArH), 6.65 (d, 1H, JAB= 3.5 Hz, ArH), 4.49 (s, 2H, CH2).

Reference： [1] Asian Journal of Chemistry, 2018, vol. 30, # 2, p. 312 - 316
[2] Patent: WO2017/17631, 2017, A2, . Location in patent: Paragraph 00310
[3] Medicinal Chemistry Research, 2013, vol. 22, # 12, p. 5940 - 5947

[ 2493-04-1 ] Synthesis Path-Downstream 1~26

1
[ 2493-04-1 ]
[ 122-01-0 ]
[ 25294-78-4 ]

Reference： [1]Patent: US2847424,1953,

2
[ 2493-04-1 ]
[ 79-04-9 ]
[ 6628-60-0 ]

Reference： [1]Patent: US2847424,1953,

3
[ 2493-04-1 ]
[ 598-21-0 ]
[ 6281-24-9 ]

Reference： [1]Patent: US2847424,1953,

4
[ 2493-04-1 ]
[ 625-36-5 ]
[ 13295-81-3 ]

Reference： [1]Patent: US2847424,1953,

6
[ 2493-04-1 ]
[ 4098-31-1 ]

Yield	Reaction Conditions	Operation in experiment
71%	With thionyl chloride; at 20℃;	A solution of compound 3 (3.5g, 25mmol) in 5mL SOCl2 was stirred at room temperature. When TLC showed no starting material remained, ice was added to the solution. Extracted with DCM, then the organic layer was dried and removed in vacuo. The residue was purified by chromatography (PE/DCM, 10/1) to give compound 4(2.8g, 71%). 1H-NMR (CDCl3, 300MHz): delta 4.598(s, 2H); 6.628(d, 1H); 7.280(d, 1H).

Reference： [1]Patent: EP3018125,2016,A1 .Location in patent: Paragraph 0874-0875; 0878
[2]Journal of the Chemical Society. Perkin transactions I,1997,p. 1147 - 1156
[3]Iowa State College Journal of Science,1932,vol. 6,p. 389,391

7
[ 698-63-5 ]
[ 2493-04-1 ]

Yield	Reaction Conditions	Operation in experiment
83%	With methanol; sodium tetrahydroborate; at 0 - 20℃; for 1h;	To a solution 5-nitrofuran-2-carbaldehyde (794 mg,5.63 mmol) in dry methanol (10 ml), sodium borohydride (320 mg, 8.44 mmol) was added inportions at 0C. Then the reaction mixture was stirred at room temperature for another 1 h. After completion, the reaction mixture was acidified with 3 N HC1 and extracted with ethyl acetate. Organic layer was washed with brine, dried over sodium sulphate and finally solvent evaporated under vacuum to obtain the compound A. This was directly used for the next step without furtherpurification (670 mg, 83%).
81.5%	With sodium tetrahydroborate; water; In tetrahydrofuran; at 20℃; for 0.5h;	A solution of compound 2 (4.24g, 0.03 mol) in 30ml THF was stirred at room temperature. Then NaBH4 (0.3g, 0.06mol) was added in several times. When TLC showed no starting material remained, the mixture was poured into 30ml water and extracted with DCM. The organic layer was dried and removed in vacuo to give compound 3(3.5g, 81.5%).
80%	With sodium tetrahydroborate; In methanol; at 0℃; for 2.5h;Inert atmosphere;	5-Nitrofuran-2-carbaldehyde (4.00 g, 28 mmol) was dissolved in anhydrous methanol (80 mL) and cooled to 0 oC. NaBH4 (1.17 g, 31 mmol) was added to the reaction mixture, which was stirred for 2.5 h. The reaction was quenched with an HCl solution (1 M, 40 mL) and extracted with EtOAc (3 x 50 mL). The combined organic layer was dried over Na2SO4 and concentrated under reduced pressure to afford a crude yellow oil. Purification by flash chromatography using a prepacked 100 g silica column [solvent A: EtOAc; solvent B: hexanes; gradient: 7%A / 93%B (1 CV), 7%A / 93%B ? 60%A / 40%B (10 CV), 60%A / 40%B (2 CV); flow rate: 100 mL/min; monitored at 254 and 280 nm] afforded (5-nitrofuran-2-yl)methanol (34) (3.23 g, 22.6 mmol, 80%) as a pale yellow oil.1H NMR (600 MHz, CDCl3) delta 7.31 (1H, d, J = 3.6 Hz), 6.58 (1H, d, J = 3.6 Hz), 4.74 (2H, s), 2.09 (1H, s). 13C NMR (151 MHz, CDCl3) delta 157.37, 151.92, 112.40, 110.61, 57.45.

62.9%	With methanol; sodium tetrahydroborate; at 20℃; for 3h;Cooling with ice;	5-nitrofurfural (10 mmol, 1.41 g) was dissolved in methanol (100 ml), and sodium borohydride (15 mmol, 0.6 g) was added thereto under an ice bath condition, and the reaction was carried out at room temperature for 3 hours.Point the plate to determine the end point of the reaction, then add water (10ml) to stop the reaction, remove the solvent methanol by rotary evaporation, and extract three times with dichloromethane (25ml * 3) to obtain an oil phase. Dry over anhydrous sodium sulfate for two hours, filter and spin The solvent was distilled off to obtain a crude product, which was passed through a column with petroleum ether: ethyl acetate (4: 1) to obtain the product 2a (0.91 g, 62.9%).
46%	With sodium tetrahydroborate; In methanol; at 0℃; for 0.5h;	To a stirred solutionof 5-nitrofurfural (3) (5 g, 35.44 mmol) in methanol (100 mL), cooled to 0 C, was added sodium borohydride (1.47 g, 38.98mmol) portion-wise and continued to stirred for additional 30 min. After completion of the reaction, checked by TLC, thes olvent was concentrated under reduced pressure and theresidue was quenched with water (2 mL) and extracted with cyclopentyl methylether (4 × 25 mL). The organic layer was washed with water (2 × 30 mL), dried over Na2SO4 and evaporated to obtain (5-nitrofuran-2-yl)methanol 4. Pale yellow oil;Yield: 2.33 g, 46 %; 1 H NMR (400 MHz, CDCl3) delta 2.50 (br s,1H, OH), 4.73 (s, 2H, -CH 2 ), 6.57 (d, 1H, J = 4 Hz, H 3 -furan),7.30 (d, 1H, J = 4.0 Hz, H 4 -furan).

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1997,p. 1147 - 1156
[2]Journal of Medicinal Chemistry,2000,vol. 43,p. 2258 - 2265
[3]Synthetic Communications,1990,vol. 20,p. 849 - 854
[4]Patent: WO2017/17631,2017,A2 .Location in patent: Paragraph 00309
[5]Patent: EP3018125,2016,A1 .Location in patent: Paragraph 0874-0875; 0877
[6]Bioorganic and Medicinal Chemistry Letters,2017,vol. 27,p. 636 - 641
[7]Bioorganic Chemistry,2020,vol. 98
[8]Patent: CN110437281,2019,A .Location in patent: Paragraph 0038-0040
[9]Journal of Chemical Research, Miniprint,1985,p. 1814 - 1823
[10]Phosphorus, Sulfur and Silicon and the Related Elements,1995,vol. 104,p. 169 - 180
[11]Asian Journal of Chemistry,2018,vol. 30,p. 312 - 316
[12]Journal of Organic Chemistry,2018,vol. 83,p. 4427 - 4440
[13]Medicinal Chemistry Research,2013,vol. 22,p. 5940 - 5947

8
[ 2493-04-1 ]
[ 821-48-7 ]
C₁₃H₂₀Cl₄N₃O₅P [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2000,vol. 43,p. 2258 - 2265

9
[ 2493-04-1 ]
[ 43204-63-3 ]
C₁₃H₂₀Br₄N₃O₅P [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2000,vol. 43,p. 2258 - 2265

10
[ 2493-04-1 ]
[ 150756-67-5 ]
[ 324770-46-9 ]

Reference： [1]Journal of Medicinal Chemistry,2000,vol. 43,p. 2258 - 2265
[2]Journal of Medicinal Chemistry,2008,vol. 51,p. 2412 - 2420

11
[ 365432-15-1 ]
[ 2493-04-1 ]
[ 365431-83-0 ]