[ CAS No. 31127-39-6 ]

Name: 31127-39-6|2,3-Dihydrobenzo[b][1,4]dioxine-6-carbaldehyde oxime|98%
Brand: Ambeed
SKU: A269239
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Quality Control of [ 31127-39-6 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 31127-39-6 ]

SDS Specification

Alternatived Products of [ 31127-39-6 ]

Product Details of [ 31127-39-6 ]

CAS No. :	31127-39-6	MDL No. :	MFCD00862517
Formula :	C₉H₉NO₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	-
M.W :	179.17 g/mol	Pubchem ID :	-
Synonyms :

Calculated chemistry of [ 31127-39-6 ]

Physicochemical Properties

Num. heavy atoms :	13
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.22
Num. rotatable bonds :	1
Num. H-bond acceptors :	4.0
Num. H-bond donors :	1.0
Molar Refractivity :	46.69
TPSA :	51.05 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.53 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.88
Log Po/w (XLOGP3) :	1.21
Log Po/w (WLOGP) :	1.27
Log Po/w (MLOGP) :	0.4
Log Po/w (SILICOS-IT) :	1.96
Consensus Log Po/w :	1.34

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-1.99
Solubility :	1.84 mg/ml ; 0.0103 mol/l
Class :	Very soluble
Log S (Ali) :	-1.88
Solubility :	2.37 mg/ml ; 0.0132 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-1.95
Solubility :	2.03 mg/ml ; 0.0113 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	3.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.36

Safety of [ 31127-39-6 ]

Signal Word:	Danger	Class:	4.1,6.1
Precautionary Statements:	P240-P210-P241-P280-P370+P378-P501-P261-P270-P271-P264-P337+P313-P305+P351+P338-P361+P364-P332+P313-P301+P310+P330-P302+P352+P312-P304+P340+P311-P403+P233-P405	UN#:	2926
Hazard Statements:	H228-H301+H311+H331-H315-H319	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 31127-39-6 ]

* 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.

Upstream synthesis route of [ 31127-39-6 ]
Downstream synthetic route of [ 31127-39-6 ]

[ 31127-39-6 ] Synthesis Path-Upstream 1~3

1
[ 31127-39-6 ]
[ 17413-10-4 ]

Reference： [1] Patent: CN108117534, 2018, A, . Location in patent: Paragraph 1180; 1181; 1182

2
[ 29668-44-8 ]
[ 31127-39-6 ]

Yield	Reaction Conditions	Operation in experiment
98%	With hydroxylamine hydrochloride; sodium hydroxide In ethanol at 80℃; for 4 h; Inert atmosphere	General procedure: To a suspension of aldehyde (30/35 mmol) in ethanol (50 mL) was added NH2OH*HCl (2 eq) and NaOH pellets (1.8 eq). The suspension was stirred at 80 C for 4 h and concentrated in vacuo. The crude product was extracted in EtOAc (200 mL). The organic layer was washed with 1 N HCl (2 200 mL), water (4 200 mL), dried (MgSO4) and concentrated in vacuo. If TLC showed impurities, the solid was washed with a minimum of cold Et2O to afford the aldoxime as a white powder.

Reference： [1] European Journal of Medicinal Chemistry, 2016, vol. 108, p. 444 - 454
[2] Bioorganic and Medicinal Chemistry Letters, 2003, vol. 13, # 10, p. 1795 - 1799
[3] Bioorganic and Medicinal Chemistry, 2004, vol. 12, # 15, p. 3965 - 3970
[4] Bulletin of the Korean Chemical Society, 2012, vol. 33, # 12, p. 4227 - 4230
[5] Advanced Synthesis and Catalysis, 2014, vol. 356, # 5, p. 977 - 981
[6] Bioorganic and Medicinal Chemistry, 2016, vol. 24, # 21, p. 5440 - 5448
[7] Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 12, p. 2674 - 2677
[8] Bioorganic and Medicinal Chemistry Letters, 2018, vol. 28, # 23-24, p. 3741 - 3747

3
[ 124362-47-6 ]
[ 31127-39-6 ]

Reference： [1] Patent: CN108117534, 2018, A, . Location in patent: Paragraph 1177; 1178; 1179

[ 31127-39-6 ] Synthesis Path-Downstream 1~37

1
[ 29668-44-8 ]
[ 31127-39-6 ]

Yield	Reaction Conditions	Operation in experiment
98%	With hydroxylamine hydrochloride; sodium hydroxide; In ethanol; at 80℃; for 4h;Inert atmosphere;	General procedure: To a suspension of aldehyde (30/35 mmol) in ethanol (50 mL) was added NH2OH*HCl (2 eq) and NaOH pellets (1.8 eq). The suspension was stirred at 80 C for 4 h and concentrated in vacuo. The crude product was extracted in EtOAc (200 mL). The organic layer was washed with 1 N HCl (2 200 mL), water (4 200 mL), dried (MgSO4) and concentrated in vacuo. If TLC showed impurities, the solid was washed with a minimum of cold Et2O to afford the aldoxime as a white powder.
	With hydroxylamine hydrochloride; sodium carbonate; In methanol; water; at 20℃; for 2h;	General procedure: To a mixture of aldehyde (10.0 mmol) in 30% methanol aqueous solution, NH2OH·HCl (0.695 g, 10.0 mmol) was added slowly. After the NH2OH·HCl was fully dissolved, Na2CO3 (0.53 g 5.0 mmol) was added and then the resulting mixture was stirred at room temperature for 2 h. The reaction mixture was diluted with water and extracted with CH2Cl2. The organic phase was dried to afford intermediate a' as white solids.
	With hydroxylamine hydrochloride; sodium carbonate; In methanol; water; at 20℃; for 2h;	General procedure: To a mixture of aldehyde 1 (10.0 mmol) in 30% methanol aqueous solution, NH2OH·HCl (0.695 g, 10.0 mmol) was added slowly. After the NH2OH·HCl was fully dissolved, Na2CO3 (0.53 g 5.0 mmol) was added and then the resulting mixture was stirred at room temperature for 2 h. The reaction mixture was diluted with water and extracted with CH2Cl2. The organic phase was dried to afford intermediate 2 as white solids.

General procedure: To a solution of 2-nitro-benzaldehyde 1a,b or benzaldehyde 4a,b (20 mmol) in methanol (15 mL) was added dropwise solution of hydroxylamine hydrochloride (40 mol) in water (10 mL) at room temperature in 30 min. Aqueous solution of sodium hydroxide (0.4 mol) was then added dropwise to the solution and the sulting mixture was stirred for 30-60 min at room temperature. Afterwards, solvent was removed under reduced pressure, the residue was quenched in crushed ice/water (10 mL) and the pH was adjusted to ~ 4 with acetic acid 50 %. The formed precipitate was isolated, washed with cold water (20 mL) and n-hexane (30 mL), and dried at 50C to afford corresponding oxime derivatives 2a,b or 5a,b, which were used for the next step without further purification.

Reference： [1]European Journal of Medicinal Chemistry,2016,vol. 108,p. 444 - 454
[2]Bioorganic and Medicinal Chemistry Letters,2003,vol. 13,p. 1795 - 1799
[3]Bioorganic and Medicinal Chemistry,2004,vol. 12,p. 3965 - 3970
[4]Bulletin of the Korean Chemical Society,2012,vol. 33,p. 4227 - 4230
[5]Advanced Synthesis and Catalysis,2014,vol. 356,p. 977 - 981
[6]Bioorganic and Medicinal Chemistry,2016,vol. 24,p. 5440 - 5448
[7]Bioorganic and Medicinal Chemistry Letters,2017,vol. 27,p. 2674 - 2677
[8]Bioorganic and Medicinal Chemistry Letters,2018,vol. 28,p. 3741 - 3747

2
[ 31127-39-6 ]
[ 596095-20-4 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2003,vol. 13,p. 1795 - 1799

3
[ 107-19-7 ]
[ 31127-39-6 ]
[3-(2,3-dihydro-benzo[1,4]dioxin-6-yl)-isoxazol-5-yl]-methanol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
67%		General procedure: To a solution of 2,3-dihydrobenzo[b][1,4]dioxine-6-carbaldehyde oximes 10 (2.69 g, 15.0 mmol) in THF (70 mL) at room temperature under nitrogen atmosphere, N-chlorosuccinimide (2.40 g, 18.0 mmol) and pyridine (120 muL, 1.50 mmol) were added. After being stirred for 40 min at 60 C, the mixture was cooled to rt and solutions of propargyl alcohol (700 muL, 12.0 mmol) in THF (2 mL) and triethylamine (2.50 mL, 18.0 mmol) in THF (4 mL) were added dropwise successively. After the mixture being stirred at 50 C for 2 h. Saturated NaHCO3 solution was added and the mixture was extracted with ethyl acetate (50 mL × 3). The organic layers were dried over anhydrous MgSO4 and concentrated. The residue was purified by flash column chromatography (hexane:EtOAc =2:1) to give the isoxazole alcohol 11 (when R2= 2,3-dihydrobenzo[b][1,4]dioxin-6-yl, 1.87 g, 67%). To a solution of thus prepared alcohol 11 (1.16 g, 5.00mmol) in dichloromethane (15 mL) at room temperature, pyridinium chlorochromate (2.16 g, 10.0 mmol) and 4 A molecular sieve (4.00 g) were added. After being stirred for 4 h, the mixture was concentrated and the residue was purified by flash column chromatography (hexane:EtOAc =3:1) to give the building block 3 (when R2= 2,3-dihydrobenzo[b][1,4]dioxin-6-yl, 740 mg, 65%). 1H NMR (500 MHz, CDCl3) delta 9.95 (s, 1H), 7.31 (s, 1H), 7.27 (d, J = 8.0 Hz, 1H), 7.13 (s, 1H), 6.90 (d, J = 8.0 Hz,1H), 4.22-4.27 (m, 4H). Other isoxazole aldehyde derivatives were synthesizedanalogously and identified with the 1H NMR spectroscopy.
		General procedure: A mixture of a' (10.0 mmol) in CH2Cl2 was stirred at room temperature, NCS (1.60 g, 12.0 mmol) was then added. The resulted mixture was stirred at reflux and propynol (0.56 g, 10.0 mmol) was added dropwise. After 0.5 h, triethylamine (1.01 g, 10 mmol) was added dropwise and refluxed for another 4 h. After cooling, the reaction mixture was washed with water and evaporated under reduced pressure. The obtained residue was purified by silica gel chromatography with petroleum ether/ethyl acetate as eluent to give intermediate b'.

Reference： [1]Bulletin of the Korean Chemical Society,2012,vol. 33,p. 4227 - 4230
[2]Bioorganic and Medicinal Chemistry,2004,vol. 12,p. 3965 - 3970
[3]Bioorganic and Medicinal Chemistry,2016,vol. 24,p. 5440 - 5448

4
[ 31127-39-6 ]
[3-(2,3-dihydro-benzo[1,4]dioxin-6-yl)-isoxazol-5-ylmethyl]-[2-(4-<i>p</i>-tolyl-piperazin-1-yl)-ethyl]-amine [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2004,vol. 12,p. 3965 - 3970

5
[ 31127-39-6 ]
[ 808740-73-0 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2004,vol. 12,p. 3965 - 3970
[2]Bulletin of the Korean Chemical Society,2012,vol. 33,p. 4227 - 4230

6
[ 31127-39-6 ]
3-(2,3-dihydro-benzo[1,4]dioxin-6-yl)-4,5-dihydro-isoxazole-5-carboxylic acid (2'-sulfamoyl-biphenyl-4-yl)-amide [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2003,vol. 13,p. 1795 - 1799

7
[ 108499-32-7 ]
[ 31127-39-6 ]
[ 773059-95-3 ]