[ CAS No. 5410-97-9 ] {[proInfo.proName]}

Name: 5410-97-9|3-Nitrodibenzo[b,d]furan|98%
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SKU: A404186
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COA NMR CNMR HPLC LC-MS

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Product Details of [ 5410-97-9 ]

CAS No. :	5410-97-9	MDL No. :	MFCD00092337
Formula :	C₁₂H₇NO₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	UVFAHDAUVZRVCC-UHFFFAOYSA-N
M.W :	213.19	Pubchem ID :	72897
Synonyms :

Calculated chemistry of [ 5410-97-9 ]

Physicochemical Properties

Num. heavy atoms :	16
Num. arom. heavy atoms :	13
Fraction Csp3 :	0.0
Num. rotatable bonds :	1
Num. H-bond acceptors :	3.0
Num. H-bond donors :	0.0
Molar Refractivity :	62.54
TPSA :	58.96 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-4.8 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.04
Log Po/w (XLOGP3) :	3.95
Log Po/w (WLOGP) :	3.49
Log Po/w (MLOGP) :	2.46
Log Po/w (SILICOS-IT) :	1.2
Consensus Log Po/w :	2.63

Druglikeness

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

Water Solubility

Log S (ESOL) :	-4.19
Solubility :	0.0139 mg/ml ; 0.0000652 mol/l
Class :	Moderately soluble
Log S (Ali) :	-4.89
Solubility :	0.00276 mg/ml ; 0.0000129 mol/l
Class :	Moderately soluble
Log S (SILICOS-IT) :	-4.35
Solubility :	0.00952 mg/ml ; 0.0000447 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	2.0 alert
Leadlikeness :	2.0
Synthetic accessibility :	2.71

Safety of [ 5410-97-9 ]

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

Application In Synthesis of [ 5410-97-9 ]

* 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 [ 5410-97-9 ]
Downstream synthetic route of [ 5410-97-9 ]

[ 5410-97-9 ] Synthesis Path-Upstream 1~3

1
[ 5410-97-9 ]
[ 26608-06-0 ]

Reference： [1] Patent: US2010/244004, 2010, A1,
[2] Patent: CN105481903, 2016, A,
[3] Patent: CN105461756, 2016, A,
[4] Organic Electronics: physics, materials, applications, 2017, vol. 43, p. 105 - 111
[5] Patent: JP2018/90561, 2018, A,
[6] Patent: CN108341795, 2018, A,
[7] Patent: EP1859798, 2015, B1,

2
[ 5410-97-9 ]
[ 98045-13-7 ]

Reference： [1] Patent: US6194409, 2001, B1,

3
[ 5410-97-9 ]
[ 98045-13-7 ]

Reference： [1] Journal of Medicinal Chemistry, 2003, vol. 46, # 12, p. 2436 - 2445

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Yield	Reaction Conditions	Operation in experiment
90%	With nitric acid at 0℃; for 2h; Cooling with ice;	Preparation of compound (2): A mixture of 65% nitric acid (23.4 g, 0.4 mol, 1 .2 eq) and trifluoroacetic acid (80 ml) at 0°C is added dropwise at 0°C to a suspension of 97% dibenzofuran (34.6 g, 0.2 mol, 1 eq) and trifluoroacetic acid (420 ml) within one hour. At the end of the addition, the resulting solution is stirred at 0°C for one hour, before being precipitated in 2 I of ice- water while stirring. Removal by suction filtration is followed by the dissolution of the crude material in dichloromethane and extraction with water. The organic phase is admixed with ethanol, and the dichloromethane is distilled out of the mixture. The concentration of the ethanolic suspension is followed by the removal by suction filtration and the washing of the product.Yield: 38.3 g (90%).1H NMR (d6-DMSO, 400 MHz): δ = 7.47 (dd, 1 H), 7.63 (dd, 1 H), 7.78 (d, 1 H), 8.25 (d, 1 H), 8.27 (d, 1 H), 8.37 (d, 1 H), 8.57 (s, 1 H).
84%	With nitric acid; trifluoroacetic acid for 2.83333h; Cooling with ice;	9 Preparation of Intermediate M-1 Trifluoroacetic acid (150 ml) was added to the reaction flask, followed by the addition of compound I-9 (14.2 g, 82 mmol), which was dissolved with vigorous stirring at room temperature, and cooled with ice water, 70% HNO3 (9.1 g, 101 mmol) Add to trifluoroacetic acid (50 ml), and slowly add to the reaction flask, stir for 40 minutes, then pour the reaction solution into 300 ml of ice water and stir for 30 minutes, and filter to obtain a white solid similar to 2M sodium hydroxide solution After washing with water, the obtained solid was recrystallized from ethyl acetate to give pale yellow solid M-1 (14.7 g, 84%).
76%	With nitric acid; trifluoroacetic acid at 10℃; for 1h; Inert atmosphere;	12.1 <1> Synthesis of 3-nitro dibenzofuran In a 1 L four-necked round bottom flask equipped with a stirrer, a Liebig condenser (not required), a thermometer, a nitrogen inlet tube and a 200 mL dropping funnel,40.0 g (0.24 mol) of benzofuran and 500 mL of trifluoroacetic acid were placed and cooled to 0 ° C. or lower in an ice water bath. Subsequently, 100 mL of trifluoroacetic acid in which 18.2 g (0.29 mol) of nitric acid (d = 1.52) was dissolved was dropped in a nitrogen gas stream so that the reaction solution did not exceed 0 ° C., and then 1 hour at 0 ° C. or lower , Followed by post-reaction to obtain a reaction solution.Next, stirrer, Liebig condenser (may be omitted), a thermometer, and a 200mL addition funnel, 4-neck round bottom flask set the 5L, stirring slowly added to crushed ice 3 Kg, the reaction The solution was slowly added, and the precipitated crystals were suction filtered. The crystal on the nutsche was washed successively with 600 mL of water, 500 mL of 5% potassium carbonate aqueous solution and 1000 mL of water, and dried in a vacuum dryer at 60 ° C. to obtain crude crystals. Then, recrystallization was performed with 350 mL of acetic acid to obtain 38.7 g (yield: 76.0%) of the desired nitro compound.

70%	With nitric acid; trifluoroacetic acid at 20℃; for 2.16667h; Cooling with ethanol ice bath;	1.1 Example 1: Preparation of (R)-2-(7-methoxycarbonyIamino-dibenzofuran-2- sulfonylamino)-3-methyl-butyric acidStep 1: Preparation of 3-nitrodibenzo[b,dlfuran[0092] The following procedures are similar to those described in Keumi et al. (1991), J. Org. Chem., 56: 4671-4677. Dibenzofuran (50 g) was mixed with 400 mL of trifluoroacetic acid (TFA). The resulting suspension was cooled in an ethanol ice bath and 11.7 mL of fuming nitric acid (HNO3, >90%) was added drop- EPO wise over 10 minutes. The reaction mixture was allowed to warm to room temperature and stirred for two hours followed by filtration. The solid from the filtration was triturated with methanol (MeOH) and dried under reduced pressure to provide 45 g of 3-nitrodibenzo[b,d]furan in 70% yield.
70%	With nitric acid; trifluoroacetic acid at 20℃; Cooling with ice;
70%	With nitric acid; trifluoroacetic acid at 20℃; Cooling;	4.1 Dibenzofuran (50 g, fine powder) was mixed with 400 mL of trifluoroacetic acid (TFA) and the resulting suspension was cooled in an ethanol-ice bath before the addition of HNO3 (11.7 mL, >90%) over 10 minutes. The reaction mixture was warmed to room temperature and stirred for 2 hours. After filtration, the resulting solid was triturated with methanol and dried under vacuum (see, e.g., Keumi, T. et al. (1991), J. O. C. 56: 4671) to produce 3-nitrodibenzo[b,d]furan (45 g, 70% yield) as a solid.
70%	With nitric acid; trifluoroacetic acid at 20℃; for 2h;
70%	With nitric acid; trifluoroacetic acid at 20℃; for 2h; Cooling with ice;	2.1 1) Synthesis of intermediate A2-2 A solution of A1-1 (8 g, 47.62 mmol) in trifluoroacetic acid (64 mL) was added slowly nitric acid (1.9 mL) under ice bath, The mixture was stirred at room temperature for 2 hours, filtered and filtered with methanol to give a yellow solid (7 g, 70%).
67%	With nitric acid In acetic acid at 90℃; for 0.166667h;
	With nitric acid; acetic acid
	With nitric acid; acetic acid
	With tetrachloromethane; nitric acid
	With mixture of gaseous nitrogen oxides; acetic acid at 20℃;
	With Nitrogen dioxide; acetic acid at 20℃;
	With nitric acid In trifluoroacetic acid at -0.1℃;
	With nitric acid; trifluoroacetic acid
	Multi-step reaction with 2 steps 1: nitric acid / trifluoroacetic acid 2: dichloromethane; ethyl acetate; N,N-dimethyl-formamide
	With nitric acid; trifluoroacetic acid at -4℃; for 2h;
	With nitric acid; acetic acid at 65℃; for 3h;	9 Example 9 3-Nitrodibenzofuran Example 9 3-Nitrodibenzofuran Combine dibenzofurane (20.0 g, 0.11 mol) and acetic acid (80 ml). Heat to 65°C. Add 98% nitric acid (20.0 g, 11.8 mol). After 3 hours, cool to room temperature to give a solid. Collect the solid by filtration, rinse with water, and dry to give the title compound.
14.7 g	With nitric acid; trifluoroacetic acid at 20℃; for 0.666667h; Cooling with ice;	2 Synthesis of 3-nitro-dibenzofuran The reaction flask was added 150ml of trifluoroacetic acid, followed by addition of dibenzofuran (14.2g, 82mmol), stirring vigorously and dissolved at room temperature, ice-water cooling bath was 70% HNO3(9.1g, 101mmol) was added to 50ml of trifluoroacetic acid was slowly added to the reaction flask and stirred for 40 minutes, after which the reaction mixture was poured into 300ml of ice water and then stirred for 30 minutes and filtered to give an off-white solid, respectively 2M hydrogen sodium hydroxide solution and water, the resulting solid was recrystallized from ethanol to give a pale yellow solid 14.7g.
14.7 g	With nitric acid; trifluoroacetic acid for 0.666667h;	2 Synthesis of 3-nitro-dibenzofuran The reaction flask was added 150ml of trifluoroacetic acid, followed by addition of dibenzofuran (14.2g, 82mmol), vigorously stirred at room temperature to dissolve the ice water cooling bath was 70% HNO3(9.1g, 101mmol) was added to 50ml of trifluoroacetic acid was slowly added to the reaction flask and stirred for 40 minutes, after which the reaction mixture was poured into 300ml of ice water and then stirred for 30 minutes and filtered to give an off-white solid, respectively 2M hydrogen sodium hydroxide solution and water, the resulting solid was recrystallized from ethanol to give a pale yellow solid 14.7g.
	With nitric acid In trifluoroacetic acid

Yield	Reaction Conditions	Operation in experiment
	With thionyl chloride at 190℃;
	Multi-step reaction with 2 steps 1: 89 percent / 80percent N₂H₄*H₂O / Raney-Ni / ethanol / 2 h / Heating 2: 1) aq. NaNO₂, aq. HCl, 2) CuCl, conc. HCl / 2) 70 deg C, 1 h

Yield	Reaction Conditions	Operation in experiment
98%	With hydrogen;palladium on activated charcoal; In methanol; at 20℃; under 2585.81 Torr;	Example 28: Preparation of (S)-2-(8-(isobutoxycarbonylamino)dibenzo[b,d]furan-3-sulfonamido)-3-methylbutanoic acid EPO <DP n="74"/>Step 1 : Preparation of dibenzo[b,d]furan-3-amine[0130] 3-Nitrodibenzo[b,d]furan obtained from nitration of dibenzofuran (Example 1) (2.13 g, 10 mmol) was mixed with 20 mL of MeOH and 0.5 g of Pd/C. The reaction was carried out using a Parr shaker at room temperature under hydrogen (50 psi) overnight. The reaction mixture was filtered through Celite. Removal of MeOH gave 1.80 g of dibenzo[b,d]furan-3 -amine as an off-white solid in 98% yield.
98%	With hydrogen;palladium 10% on activated carbon; In methanol; at 20℃; under 2585.81 Torr;	3-Nitrodibenzo[b,d]furan (an intermediate in the preparation of Example 4) (2.13 g, 10 mmole) was mixed with 20 mL of MeOH and 0.5 g of 10% Pd/C (wt/wt), and the reaction was shaken with a Parr shaker at room temperature under an atmosphere of hydrogen (50 psi) overnight. The reaction mixture was filtered through Celite and the filtrate was concentrated to give 1.80 g of pure dibenzo[b,d]furan-3-amine as an off-white solid in a 98% yield.
97%	With palladium on activated charcoal; hydrogen; In ethyl acetate; under 3102.97 Torr; for 0.25h;	Compound M-1 (12.6 g, 60 mmol) and ethyl acetate (800 ml) were sequentially added to a round bottom flask, and air was purged with nitrogen for 5 minutes, then Pd/C was added, hydrogenation was started, and hydrogen gas was pressurized at 60 psi. The pressure of 60 psi was stable for 15 minutes and the reaction was complete when it was no longer reduced. The reaction solution was filtered through a sand funnel and the filtrate was dried to give a white solid M-2 (10.9 g, 97%).

[ CAS No. 5410-97-9 ] {[proInfo.proName]}

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