[ CAS No. 22590-64-3 ]

Name: 22590-64-3|3-(Oxiran-2-ylmethoxy)benzaldehyde|97%
Brand: Ambeed
SKU: A702326
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Quality Control of [ 22590-64-3 ]

COA NMR CNMR HPLC LC-MS

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Product Details of [ 22590-64-3 ]

CAS No. :	22590-64-3	MDL No. :	MFCD00203974
Formula :	C₁₀H₁₀O₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	N/A
M.W :	178.18 g/mol	Pubchem ID :	-
Synonyms :

Safety of [ 22590-64-3 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P330-P363-P501	UN#:
Hazard Statements:	H302-H312-H332	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 22590-64-3 ]

* 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 [ 22590-64-3 ]

[ 22590-64-3 ] Synthesis Path-Downstream 1~27

1
[ 304-20-1 ]
[ 22590-64-3 ]
[ 160951-45-1 ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1994,vol. 42,p. 1609 - 1616

2
[ 160951-65-5 ]
[ 22590-64-3 ]
Diethyl-(6-{N'-[1-(3-oxiranylmethoxy-phenyl)-meth-(E)-ylidene]-hydrazino}-pyridazin-3-yl)-amine [ No CAS ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1994,vol. 42,p. 1609 - 1616

3
[ 22590-64-3 ]
1-Isopropylamino-3-[3-(phthalazin-1-yl-hydrazonomethyl)-phenoxy]-propan-2-ol [ No CAS ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1994,vol. 42,p. 1609 - 1616

4
[ 22590-64-3 ]
1-{3-[(6-Diethylamino-pyridazin-3-yl)-hydrazonomethyl]-phenoxy}-3-isopropylamino-propan-2-ol [ No CAS ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1994,vol. 42,p. 1609 - 1616

5
[ 110-89-4 ]
[ 22590-64-3 ]
[ 892404-75-0 ]

Yield	Reaction Conditions	Operation in experiment
72%	In ethanol;Heating / reflux;	A mixture of 3- oxiranylmethoxy-benzaldehyde (0.59 g, 3.31 mmol) and piperidine (0.34 ml_, 3.48 mmol) in EtOH (10 mL) was heated at reflux overnight. The reaction mixture was EPO <DP n="75"/>allowed to cool to rt and then was concentrated. The crude material was purified by FCC (MeOH/DCM) to give the desired product as a yellow oil (0.63 g, 72%). MS (ESI): mass calcd for C15H2INO3, 263.15; m/z found, 264.4 [M+H]+. 1H NMR (CDCI3): 9.98 (s, 1 H), 7.48-7.41 (m, 3H)1 7.23-7.21 (m, 1 H), 4.13-4.08 (m, 1 H), 4.06-4.00 (m, 2H), 2.76-2.57 (m, 2H), 2.53-2.45 (m, 2H), 2.42-2.31 (m, 2H), 1.64- 1.57 (m, 4H), 1.49-1.45 (m, 2H).

Reference： [1]Patent: WO2006/66197,2006,A1 .Location in patent: Page/Page column 73

6
[ 100-83-4 ]
[ 106-89-8 ]
[ 22590-64-3 ]

Yield	Reaction Conditions	Operation in experiment
75%		To a solution of 3-hydroxybenzaldehyde (2.0 g, 16.38 mmol) in DMF (25 mL) was added NaH (60%, 982.6 mg, 24.57 mmol) at 0C in portions. The mixture was stirred at this temperature for 30 mintues before a solution of 2-(chloromethyl)oxirane (2.27 g, 24.57 mmol) in DMF (5 mL) was slowly added into the reaction mixture which was then allowed to reach room temperature slowly and stirred for 16 h. The solvent was removed by concentration and the residue dissolved in ethyl acetate and washed with water. T the separated organic layer was dried over sodium sulfate, filtered and concentrated. The crude product was then purified by column chromatography. (2.2 g, yield 75%) MS (ESI+) e/z: 179.1 [M+l]+
58%	With potassium carbonate; In acetonitrile;Heating / reflux;	To a mixture of 3- hydroxybenzaldehyde (10.0 g, 81.9 mmol) and K2CO3 (17.0 g, 123.0 mmol) in acetonitrile (235 ml_) was added epichlorohydrin (15.2 g, 163.8 mmol) and the mixture was heated at reflux overnight. The mixture was allowed to cool to rt, was diluted with EtOAc, washed with 1 N NaOH and brine, dried (MgSO4), and concentrated. The crude material was purified by FCC (EtOAc/hexanes) to give the desired product as a clear oil (8.49 g, 58%). 1H NMR (CDCI3): 9.98 (s, 1 H), 7.50-7.44 (m, 2H), 7.41 -7.40 (m, 1 H), 7.24-7.21 (m, 1 H), 4.33 (dd, J=11.0, 2.8, 1 H), 4.00-3.97 (m, 1 H), 3.40-3.37 (m, 1 H), 2.94-2.93 (m, 1 H), 2.79-2.78 (m, 1 H).

Reference： [1]ChemMedChem,2020
[2]Patent: WO2014/100695,2014,A1 .Location in patent: Paragraph 00306
[3]Patent: WO2006/66197,2006,A1 .Location in patent: Page/Page column 73

7
[ 22590-64-3 ]
[ 1069791-50-9 ]

Reference： [1]Patent: WO2014/100695,2014,A1

8
[ 22590-64-3 ]
[ 1616095-72-7 ]

Reference： [1]Patent: WO2014/100695,2014,A1

9
[ 91-21-4 ]
[ 22590-64-3 ]
[ 1616099-10-5 ]

Yield	Reaction Conditions	Operation in experiment
63%	In ethanol; at 110℃; for 3h;	A solution of <strong>[22590-64-3]3-(oxiran-2-ylmethoxy)benzaldehyde</strong> (1.0 g, 5.61 mmol) and 1,2,3,4- tetrahydroisoquinoline (1.49 g, 11.22 mmol) in EtOH (20 mL) was heated at 110C for 3 h. The solvent was then removed by concentration and the residue dissolved in ethyl acetate, washed with water and the separated organic layer dried and concentrated. The crude product was purified by column chromatography. (1.1 g, yield 63%.) MS (ESI+) e/z: 312.3 [M+l]+

Reference： [1]Patent: WO2014/100695,2014,A1 .Location in patent: Paragraph 00307

10
[ 100-83-4 ]
[ 3132-64-7 ]
[ 22590-64-3 ]

Yield	Reaction Conditions	Operation in experiment
		[00351] To a solution of 3-hydroxybenzaldehyde (2.0 g, 16.38 mmol) in DMF (30 niL) at 0 C was added NaH (983 mg, 24.57 mmol) in portions. After 0.5 h, a solution of 2- (bromomethyl)oxirane (2.69 mg, 19.65 mmol) in DMF (5 mL) was added and the reaction mixture was warmed to room temperature for 5 h. The mixture was concentrated, dissolved in ethyl acetate and washed with water. The organic portion was dried over sodium sulfate, filtered and concentrated. The crude product was used in the next step without further purification. (2.1 g, yield 72%) MS (ESI+) e/z: 179.1 [M+l]+.
		Sodium hydride (60% in mineral oil, 983 mg, 24.57 mmol) was added in portions to a stirred and cooled (0 C) solution of 3-hydroxybenzaldehyde (2.0 g, 16.38 mmol) in dimethylformamide (30 mL) and the mixture was then stuffed at 0 C for 0.5 h before a solution of 2-(bromomethyl)oxirane (2.69 mg, 19.65 mmol) in dimethylformamide (5 mL) was added. Stirring was continued for 5 h at ambient temperature. The solvent then was removed in vacuo and the residue was dissolved in ethyl acetate (100 mL), washed with water (30 mL) and the separated organic layer was dried over sodium sulfate. The solution was filtered, and the filtrate concentrated in vacuo. The crude product (2.1 g, 72%) was used in next step without further purification. LCMS (mlz): 179.1 (M+1).

Reference： [1]Patent: WO2014/100734,2014,A1 .Location in patent: Paragraph 00351
[2]ACS Medicinal Chemistry Letters,2016,vol. 7,p. 162 - 166
[3]Patent: WO2015/200677,2015,A2 .Location in patent: Paragraph 00441; 00442

11
[ 22590-64-3 ]
[ 1616059-87-0 ]

Reference： [1]Patent: WO2014/100734,2014,A1
[2]ACS Medicinal Chemistry Letters,2016,vol. 7,p. 162 - 166
[3]Patent: WO2015/200677,2015,A2

12
[ 22590-64-3 ]
[ 1616059-88-1 ]

Reference： [1]Patent: WO2014/100734,2014,A1

13
[ 22590-64-3 ]
[ 1616059-30-3 ]

Reference： [1]Patent: WO2014/100734,2014,A1

14
[ 1003-03-8 ]
[ 22590-64-3 ]
[ 1616059-86-9 ]

Yield	Reaction Conditions	Operation in experiment
		[00352] To a solution of <strong>[22590-64-3]3-(oxiran-2-ylmethoxy)benzaldehyde</strong> (1.0 g, 5.61 mmol) in MeOH (15 mL) was added cyclopentanamine (502 mg, 5.89 mmol) at room temperature. After 4 h, sodium borohydride (318 mg, 8.42 mmol) was added in portions and the mixture was stirred for another 1 h. The reaction mixture was quenched by adding aquesous 1 N HCl until the pH was adjusted to 4-5. The resulting solution was diluted with ethyl acetate, washed with water, dried over sodium sulfate, filtered and concentrated. The crude product was used in the next step without further purification. (1.1 g, yield 79%) MS (ESf ) e/z: 248.2 [M+l]+.
		To a solution of <strong>[22590-64-3]3-(oxiran-2-ylmethoxy)benzaldehyde</strong> (1.0 g, 5.61 mmol) in methanol (15 mL) was added cyclopentanamine (502 mg, 5.89 mmol). After addition, the mixture was stirred at ambient temperature for 4 h and then NaBH4 (318 mg, 8.42 mmol) was added. The resulting mixture was stuffed for another 1 h before quenching by addition of aqueous iN HC1, adjusting to pH 6-7. The solution was diluted with ethyl acetate (30 mL) and the organic layer was washed with water (10 mL). The separated organic layer was dried over sodium sulfate, filtered, and concentrated in vacuo. The crude product (1.1 g, 79%) was used in next step without further purification. LCMS (mlz): 248.2 (M+1).

Reference： [1]Patent: WO2014/100734,2014,A1 .Location in patent: Paragraph 00352
[2]ACS Medicinal Chemistry Letters,2016,vol. 7,p. 162 - 166
[3]Patent: WO2015/200677,2015,A2 .Location in patent: Paragraph 00443; 00444

15
[ 71-41-0 ]
[ 22590-64-3 ]
3-(2-hydroxy-3-amyloxy-n-propoxy)benzaldehyde [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	With zirconyl(IV) nitrate hydrate; at 45℃; for 0.5h;	General procedure: A mixture ofstyrene epoxide (120 mg, 1.0 mmol) and t-butyl alcohol (3 ml) and ZrO(NO3)2 nH2O (46 mg, 20 mol%).The mixture was heated under stirring at 45 C. The progress ofreaction was monitored by GC-MS and TLC. After completion, the reaction mixturewas concentrated under the reduced pressure. Then crude product was purifiedusing column cromatography (20% ethyl acetate:pet ether, rf 0.6) to afford 168.7 mg (87 %) of 2-tert-butoxy-2-phenylethanolas a whitesolid. obs mp 76-78 C, reported mp 77-79 C; 61H NMR (500 MHz, CDCl3) delta 7.39-7.28 (m, 5H), 4.65 (dd, J= 8.05, 4.39 Hz, 1H), 3.56-3.50 (m, 2H), 1.21 (s, 9H); 13C NMR (125MHz, CDCl3) 28.7, 67.8, 74.8, 75.1, 126.3, 127.2, 128.1, 142.2; HRMS(EI) calcd for C12H18O2 (M+) 194.3068, found194.3066.

Reference： [1]Tetrahedron Letters,2015,vol. 56,p. 5916 - 5919

16
[ 22590-64-3 ]
1-(3-((cyclopentylamino)methyl)phenoxy)-3-(3,4-dihydro-2,7-naphthyridin-2(1H)-yl)propan-2-ol trifluoroacetate salt [ No CAS ]