[ CAS No. 93-84-5 ] {[proInfo.proName]}

Name: 93-84-5|5-Nitro-1H-benzo[d]imidazol-2(3H)-one|97%
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Quality Control of [ 93-84-5 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 93-84-5 ]

Product Details of [ 93-84-5 ]

CAS No. :	93-84-5	MDL No. :	MFCD00220274
Formula :	C₇H₅N₃O₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	DLJZIPVEVJOKHB-UHFFFAOYSA-N
M.W :	179.13	Pubchem ID :	3725611
Synonyms :

Calculated chemistry of [ 93-84-5 ]

Physicochemical Properties

Num. heavy atoms :	13
Num. arom. heavy atoms :	9
Fraction Csp3 :	0.0
Num. rotatable bonds :	1
Num. H-bond acceptors :	3.0
Num. H-bond donors :	2.0
Molar Refractivity :	47.74
TPSA :	94.47 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-7.12 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.73
Log Po/w (XLOGP3) :	0.39
Log Po/w (WLOGP) :	0.76
Log Po/w (MLOGP) :	-0.19
Log Po/w (SILICOS-IT) :	-0.02
Consensus Log Po/w :	0.34

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.64
Solubility :	4.08 mg/ml ; 0.0228 mol/l
Class :	Very soluble
Log S (Ali) :	-1.94
Solubility :	2.06 mg/ml ; 0.0115 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-2.2
Solubility :	1.14 mg/ml ; 0.00634 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	2.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.92

Safety of [ 93-84-5 ]

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

Application In Synthesis of [ 93-84-5 ]

* 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 [ 93-84-5 ]
Downstream synthetic route of [ 93-84-5 ]

[ 93-84-5 ] Synthesis Path-Upstream 1~1

1
[ 93-84-5 ]
[ 95-23-8 ]

Yield	Reaction Conditions	Operation in experiment
86%	With hydrogen In methanol; ethyl acetate for 6 h;	Step: 21bSynthesis of 5-Amino-l,3-dihydro-benzoimidazol-2-one.Procedure:Pd-C(140 mg) was added to a solution of 5-Nitro-l,3-dihydro-benzoimidazol-2-one (1.4g, 0.0078mol) in MeOH and EtOAc, and was hydrogenated for 6hrs. The reaction was monitored by the TLC (10percent methanol in chloroform). The resulting reaction mixture was filtered through celite bed and was concentrated to afford lg (86 percent yield) of 5-Amino-l,3- dihydro-benzoimidazol-2-one.
78%	With hydrogen In ethanol for 3 h;	EXAMPLE 35; [0198] This example illustrates a preparation of 5-(6-methoxy-l-oxoisoindolin-2-yl)-l/-f- benzo[</]imidazol-2(3H)-one in an embodiment of the invention.; Step A: Synthesis of 5-amino-lH-benzo[<i]imidazol-2(3/-/)-one as an intermediate <n="80"/>; [0199] A mixture of 5-nitro-l/f-benzo[1H NMR (300 MHz, CDCl₃) δ 6.75-6.73 (m, IH), 6.41-6.35 (m, 2H); ESI MS m/z 150 [M + H]⁺.

Reference： [1] Patent: WO2012/59932, 2012, A1, . Location in patent: Page/Page column 161-162
[2] Patent: WO2009/42907, 2009, A1, . Location in patent: Page/Page column 78-79
[3] Journal of the American Chemical Society, 1958, vol. 80, p. 1662
[4] Patent: WO2012/115479, 2012, A2, . Location in patent: Page/Page column 23
[5] Patent: CN104151251, 2017, B, . Location in patent: Paragraph 0024

[ 93-84-5 ] Synthesis Path-Downstream 1~88

1
[ 615-16-7 ]
[ 93-84-5 ]

Reference： [1]Journal of the Chemical Society,1950,p. 1515,1516
[2]Zhurnal Obshchei Khimii,1957,vol. 27,p. 127,130; engl. Ausg. S. 143, 147

2
[ 5955-72-6 ]
[ 93-84-5 ]

Reference： [1]Chemische Berichte,1912,vol. 45,p. 3249

3
[ 93-84-5 ]
[ 108-24-7 ]
[ 2735-74-2 ]

Reference： [1]Journal of the American Chemical Society,1958,vol. 80,p. 1662

4
[ 93-84-5 ]
[ 77-78-1 ]
[ 43027-50-5 ]

Yield	Reaction Conditions	Operation in experiment
96%	In sodium hydroxide;	a 1,3-dimethyl-<strong>[93-84-5]5-nitro-1,3-dihydrobenzimidazol-2-one</strong> 90 parts of <strong>[93-84-5]5-nitro-1,3-dihydrobenzimidazol-2-one</strong> are suspended in 500 parts of aqueous sodium hydroxide solution (30%) and the suspension is heated to 53 C.; 161 parts of dimethyl sulphate are added dropwise over 12 hours during which the temperature rises to 70 C. The mixture is cooled to room temperature and filtered and the solid product is washed to neutrality. Drying under reduced pressure at 80 C. gives 99 parts of a beige powder of a compound of the following formula Yield: 96% Melting point: 206.3 C. 1H-NMR (DMSO): delta: 3.35 (s, CH3)-3.37 (s,CH3)-7.28 (d, 3J=9 Hz, H-C7)-7.98 (d, 4J=2 Hz, H-C4)-8.00 (dd, 3J=9 Hz, 4J=2Hz, H-C6)
	In sodium hydroxide;	a 1,3-Dimethyl-<strong>[93-84-5]5-nitro-1,3-dihydrobenzimidazol-2-one</strong> 90 parts of <strong>[93-84-5]5-nitro-1,3-dihydrobenzimidazol-2-one</strong> are suspended in 500 parts of aqueous sodium hydroxide solution (30%) and the suspension is heated to 53 C.; 161 parts of dimethyl sulphate are added dropwise over 12 hours during which the temperature rises to 70 C. The mixture is cooled to room temperature and filtered and the solid product is washed to neutrality. Drying under reduced pressure at 80 C. gives 99 parts of a beige powder of a compound of the following formula

Reference： [1]Patent: US6255482,2001,B1
[2]Russian Journal of Organic Chemistry,2011,vol. 47,p. 1190 - 1193
[3]Zhurnal Obshchei Khimii,1957,vol. 27,p. 127,130; engl. Ausg. S. 143, 147
[4]Patent: US6617453,2003,B1

5
[ 93-84-5 ]
[ 74-88-4 ]
[ 43027-50-5 ]

Yield	Reaction Conditions	Operation in experiment
93%		Example 3; Synthesis of Compound 19; DMF (10 ml) was added to 0.6 g of 60% NaH (15.12 mM) in a 100 mL round bottom flask under N2. Added to the flask was 1.29 g of 5-nitro-2-benzimidazolinone (7.20 mM) in 10 mL DMF and rinsed with 10 mL more DMF. The solution was stirred 25 minutes and 10.22 g MeI (72 mM) was added and then stirred a further 3 hours. HCl (200 mL, 1 M) was added to the solution and then was extracted with EtOAc, washed with brine, and dried over MgSO4 and then concentrated in vacuo and flashed 0 to 100% EtOAc in hexanes to give 1.4 g of 1,3-dimethyl-<strong>[93-84-5]5-nitro-1H-benzo[d]imidazol-2(3H)-one</strong> (93% yield).
86%	With potassium carbonate; In N,N-dimethyl-formamide; at 0 - 20℃;	To a solution of <strong>[93-84-5]5-nitro-1H-benzo[d]imidazol-2(3H)-one</strong> (55 g, 309 mmol) in 150 mL of DMF was added K2CO3 (85 g, 618 mmol), the reaction mixture was cooled to 0 C., then iodomethane (109 g, 772 mmol) was slowly added. The reaction mixture was stirred at RT overnight, then water was added to the reaction mixture. The resulting suspension was filtered and the collected solids were washed with water (200 mL) and dried to give 1,3-dimethyl-<strong>[93-84-5]5-nitro-1H-benzo[d]imidazol-2(3H)-one</strong> as a yellow solid (55 g, 86%). MS (ES+) C9H9N3O3 requires: 207. found: 208 [M+H]+.

Reference： [1]Patent: US2007/37791,2007,A1 .Location in patent: Page/Page column 40-41
[2]Patent: US2016/60260,2016,A1 .Location in patent: Paragraph 0182
[3]Journal of Heterocyclic Chemistry,1992,vol. 29,p. 1069 - 1076
[4]Journal of the American Chemical Society,1958,vol. 80,p. 1662

7
[ 93-84-5 ]
[ 3705-86-0 ]

Reference： [1]Zhurnal Obshchei Khimii,1957,vol. 27,p. 127,130; engl. Ausg. S. 143, 147
[2]Monatshefte fur Chemie,1976,vol. 107,p. 1307

8
[ 93-84-5 ]
[ 50796-10-6 ]

Reference： [1]Zhurnal Obshchei Khimii,1957,vol. 27,p. 127,130; engl. Ausg. S. 143, 147
[2]Journal of the Chemical Society,1950,p. 1515,1516

9
[ 5466-84-2 ]
[ 93-84-5 ]

Reference： [1]Annali di Chimica,1959,vol. 49,p. 1809,1812

10
[ 1026685-07-3 ]
[ 93-84-5 ]

Reference： [1]Chemische Berichte,1884,vol. 17,p. 2630
[2]Chemische Berichte,1884,vol. 17,p. 2630

11
[ 99-56-9 ]
[ 57-13-6 ]
[ 93-84-5 ]

Yield	Reaction Conditions	Operation in experiment
90%	With sulfated polyborate; at 120℃; for 2h;	General procedure: A mixture of amine (4 mmol or 2 mmol), or substituted OPDA (2 mmol), urea (2.4mmol), or N-phenylurea (2 mmol) and sulfated polyborate (10 wt%) was heated at 120C in an oil bath. The reaction was monitored by thin layer chromatography. After completion of the reaction, the mixture was cooled to room temperature and quenched by water (5 mL); solid precipitated was filtered at vacuum pump, washed with water (3×5 mL), dried under vacuum and recrystallized from ethanol to afford the pure product.
		A solution of 1,2-diamino-4-nitrobenzene (3. 0g) and urea (7.06g) in dimethylformamide was stirred and heated at reflux for 5h. The cooled mixture was poured into water and the solid was collected by filtration. The solid was suspended in hot water and the remaining solid was collected. The resultant solid was then suspended in hydrochloric acid (1 M), stirred and the remaining solid was collected and air dried to give 5-nitro-1, 3-dihydrobenzimidazol-2-one as a tan coloured solid (1. 9g). 'H NMR (DMSO-d6) d 11.4 (br s, 1 H) 11.2 (br s 1 H) 7.95 (dd, 1 H) 7.7 (d, 1 H) 7.1 (d, 1 H)

Reference： [1]Tetrahedron Letters,2017,vol. 58,p. 4304 - 4307
[2]Asian Journal of Chemistry,2013,vol. 25,p. 509 - 511
[3]Journal of Heterocyclic Chemistry,1992,vol. 29,p. 1069 - 1076
[4]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 1403 - 1407
[5]Chemische Berichte,1912,vol. 45,p. 3249
[6]Patent: WO2005/35526,2005,A1 .Location in patent: Page/Page column 52

12
[ 93-84-5 ]
C₇H₄N₃O₃^(1-)*Na⁽¹⁺⁾ [ No CAS ]

Reference： [1]Chemistry of Natural Compounds,1983,vol. 19,p. 738 - 739
Khimiya Prirodnykh Soedinenii,1983,p. 776 - 778

13
[ 5310-51-0 ]
[ 93-84-5 ]

Reference： [1]Collection of Czechoslovak Chemical Communications,1988,vol. 53,p. 1044 - 1052
[2]Collection of Czechoslovak Chemical Communications,1988,vol. 53,p. 1044 - 1052

14
[ 94-52-0 ]
[ 93-84-5 ]

Reference： [1]Chemistry of Natural Compounds,1983,vol. 19,p. 124 - 125
Khimiya Prirodnykh Soedinenii,1983,p. 121

15
[ 70254-61-4 ]
[ 99-56-9 ]
[ 1792-40-1 ]
[ 93-84-5 ]
[ 193613-57-9 ]
4-acetonylidene-7-nitro-1,5-benzodiazepin-2-one [ No CAS ]

Reference： [1]Bulletin des Societes Chimiques Belges,1997,vol. 106,p. 205 - 210

16
[ 93-84-5 ]
[ 272116-04-8 ]
C₃₁H₂₃N₃O₇ [ No CAS ]

Reference： [1]Journal of the Chemical Society. Perkin Transactions 1 (2001),2000,p. 1037 - 1043

Yield	Reaction Conditions	Operation in experiment
87.8%	With sodium hydrogen sulfide; In 1-methyl-pyrrolidin-2-one; at 90℃; under 22502.3 Torr; for 24h;	General procedure: Add in a 15ml Teflon-lined reactor216 mg (2 mmol) of o-phenylenediamine, 56 mg (1 mmol)NaHS (molar ratio of o-phenylenediamine to NaHS is 1:2),Add 1 mL of NMP as the reaction solvent.Put the magnets and tighten the reactor.Then charge 3MPa of carbon dioxide,The reaction was stirred at 90 C for 24 hours.After cooling the reactor to room temperature,Extracted with ethyl acetate,Washed with saturated saline,After drying the organic layer, the solvent is removed under reduced pressure to give a crude material;The crude product is separated by recrystallization or column chromatography (200-300 mesh silica gel,Petroleum ether and ethyl acetate as eluent)99% white powder benzimidazolone 116mg,The yield was 88%.

19
[ 93-84-5 ]
1-halogenepoxy propane [ No CAS ]
5-Nitro-1,3-bis-oxiranylmethyl-1,3-dihydro-benzoimidazol-2-one [ No CAS ]

Reference： [1]Arzneimittel-Forschung/Drug Research,1984,vol. 34,p. 663 - 668

20
[ 93-84-5 ]
[ 24424-99-5 ]
[ 438200-95-4 ]
2,3-dihydro-5-nitro-2-oxo-1H-benzimidazole-1-carboxylic acid 1,1-dimethylethyl ester [ No CAS ]

Reference： [1]Zeitschrift fur Naturforschung, B: Chemical Sciences,2002,vol. 57,p. 349 - 354
[2]Bioconjugate Chemistry,2015,vol. 26,p. 120 - 127

21
[ 93-84-5 ]
[ 98-59-9 ]
2,3-dihydro-5-nitro-1,3-bis(4-tolylsulfonyl)-1H-benzimidazol-2-one [ No CAS ]

Reference： [1]Zeitschrift fur Naturforschung, B: Chemical Sciences,2002,vol. 57,p. 349 - 354

22
[ 93-84-5 ]
[ 93-11-8 ]
2,3-dihydro-1,3-bis(naphth-2-ylsulfonyl)-5-nitro-1H-benzimidazol-2-one [ No CAS ]

Reference： [1]Zeitschrift fur Naturforschung, B: Chemical Sciences,2002,vol. 57,p. 349 - 354

23
[ 616-79-5 ]
[ 93-84-5 ]

Reference： [1]Synthetic Communications,2004,vol. 34,p. 735 - 742

24
[ 93-84-5 ]
2,3-dihydro-1-(naphth-2-ylsulfonyl)-5-nitro-1H-benzimidazol-2-one [ No CAS ]

Reference： [1]Zeitschrift fur Naturforschung, B: Chemical Sciences,2002,vol. 57,p. 349 - 354

25
[ 93-84-5 ]
[ 438200-98-7 ]

Reference： [1]Zeitschrift fur Naturforschung, B: Chemical Sciences,2002,vol. 57,p. 349 - 354

26
[ 93-84-5 ]
[ 90403-68-2 ]

Reference： [1]Chemistry of Natural Compounds,1983,vol. 19,p. 738 - 739
Khimiya Prirodnykh Soedinenii,1983,p. 776 - 778

27
[ 97-00-7 ]
[ 93-84-5 ]

Reference： [1]Collection of Czechoslovak Chemical Communications,1988,vol. 53,p. 1044 - 1052

28
[ 93-84-5 ]
[ 59747-16-9 ]

Reference： [1]Journal of the American Chemical Society,1958,vol. 80,p. 1662

29
[ 93-84-5 ]
[ 832102-60-0 ]

Reference： [1]Journal of the Chemical Society,1950,p. 1515,1516

30
[ 93-84-5 ]
5-nitro-2-piperidino-1⁽³⁾<i>H</i>-benzimidazole [ No CAS ]

Reference： [1]Journal of the Chemical Society,1950,p. 1515,1516

31
[ 93-84-5 ]
[ 90324-08-6 ]

Reference： [1]Zhurnal Obshchei Khimii,1957,vol. 27,p. 127,130; engl. Ausg. S. 143, 147
[2]Zhurnal Obshchei Khimii,1957,vol. 27,p. 127,130; engl. Ausg. S. 143, 147

32
[ 93-84-5 ]
5-isopropylamino-4,6-dinitro-1,3-dihydro-benzimidazol-2-one [ No CAS ]

Reference： [1]Journal of the Chemical Society,1950,p. 1515,1516

33
[ 93-84-5 ]
(4-chloro-phenyl)-(5-nitro-1⁽³⁾<i>H</i>-benzimidazol-2-yl)-amine [ No CAS ]

Reference： [1]Journal of the Chemical Society,1950,p. 1515,1516

34
[ 93-84-5 ]
[ 96461-50-6 ]

Reference： [1]Zhurnal Obshchei Khimii,1957,vol. 27,p. 127,130; engl. Ausg. S. 143, 147

35
[ 93-84-5 ]
[ 98590-15-9 ]

Reference： [1]Zhurnal Obshchei Khimii,1957,vol. 27,p. 127,130; engl. Ausg. S. 143, 147
[2]Zhurnal Obshchei Khimii,1957,vol. 27,p. 127,130; engl. Ausg. S. 143, 147
[3]Zhurnal Obshchei Khimii,1957,vol. 27,p. 127,130; engl. Ausg. S. 143, 147

36
[ 93-84-5 ]
[ 96461-87-9 ]

Reference： [1]Journal of the Chemical Society,1950,p. 1515,1516
[2]Zhurnal Obshchei Khimii,1957,vol. 27,p. 127,130; engl. Ausg. S. 143, 147

37
[ 35411-68-8 ]
[ 93-84-5 ]

Reference： [1]Chemische Berichte,1884,vol. 17,p. 2630

38
[ 93-84-5 ]
[ 75-26-3 ]
[ 925220-86-6 ]

Yield	Reaction Conditions	Operation in experiment
	With caesium carbonate; In N,N-dimethyl-formamide; at 80℃; for 12h;	Example 32; Synthesis of Compound 65; Commercially available 5-Nitro-2benzimidazolinone a was dissolved in 50 ml of DMF in a round bottom flask with a vigreux condensation column attached. To this solution was added 23.65 g Cs2CO3 and 8.93 g of 2-bromopropane and the mixture was placed under N2 in an oil bath heated to 80 C. for 12 hours. The reaction was almost complete by TLC, so it was cooled to room temp, diluted with 1 M HCl, extracted with EtOAc, washed with brine, dried over MgSO4, concentrated under vacuum, and flashed on silica (EtOAc/hexanes) to give 7.64 g compound b. Compound b (6.35 g) was dissolved in 200 ml EtOH and 200 uL of concentrated HCl and bubbled under N2 for 10 minutes at which time 2 scoops of 10% Pd/C was added and an H2 balloon attached. This was stirred for 48 hours. The reaction was completed by LCMS, filtered over celite and concentrated under vacuum to give compound c (5.6 g) in a 99% yield.

Reference： [1]Patent: US2007/37791,2007,A1 .Location in patent: Page/Page column 65-66

39
[ 93-84-5 ]
[ 75-03-6 ]
[ 24786-47-8 ]

Yield	Reaction Conditions	Operation in experiment
	With caesium carbonate; In N,N-dimethyl-formamide; at 80℃; for 12h;	Example 31; Synthesis of Compound 64; Commercially available 5-nitro-2-benzimidazolinone a was dissolved in 70 ml of DMF in a round bottom flask with a vigreux condensation column attached. To this solution was added 9.22 g Cs2CO3 and 4.41 g of ethyl iodide and the mixture was placed under N2 in an oil bath heated to 80 C. for 12 hours. The reaction was almost complete by TLC, so it was cooled to room temp, diluted with 1 M HCl, extracted with EtOAc, washed with brine, dried over MgSO4, concentrated under vacuum, and flashed by ISCO (EtOAc/hexanes) to give compound b. Compound b was dissolved in 200 ml EtOH and 200 uL of concentrated HCl and bubbled under N2 for 10 minutes at which time 2 scoops of 10% Pd/C was added and an H2 balloon attached. This was stirred 12 hours. The reaction was completed by LCMS, filtered over celite and concentrated under vacuum to give compound c.

Reference： [1]Patent: US2007/37791,2007,A1 .Location in patent: Page/Page column 64-65

40
[ 93-84-5 ]
1,5,6-trinitro-2,3-dihydro-1H-benzimidazol-2-one [ No CAS ]
1,3,5,6-tetranitro-2,3-dihydro-1H-benzimidazol-2-one [ No CAS ]
1,4,5,6-tetranitro-2,3-dihydro-1H-benzimidazol-2-one [ No CAS ]

Reference： [1]Russian Journal of Organic Chemistry,2009,vol. 45,p. 872 - 878

41
[ 93-84-5 ]
1,5,6-trinitro-2,3-dihydro-1H-benzimidazol-2-one [ No CAS ]
[ 3705-86-0 ]
[ 50796-10-6 ]

Reference： [1]Russian Journal of Organic Chemistry,2009,vol. 45,p. 872 - 878

42
[ 1192307-15-5 ]
[ 93-84-5 ]

Reference： [1]Journal of Organic Chemistry,2009,vol. 74,p. 7974 - 7977

43
[ 64-67-5 ]
[ 93-84-5 ]
[ 24786-47-8 ]