[ CAS No. 118469-15-1 ] {[proInfo.proName]}

Name: 118469-15-1|5-Fluoro-2-methyl-1H-benzo[d]imidazole|97%
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Quality Control of [ 118469-15-1 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 118469-15-1 ]

CAS No. :	118469-15-1	MDL No. :	MFCD00792439
Formula :	C₈H₇FN₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	IWDUKSHNFODGKM-UHFFFAOYSA-N
M.W :	150.15	Pubchem ID :	2775375
Synonyms :

Calculated chemistry of [ 118469-15-1 ]

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	9
Fraction Csp3 :	0.12
Num. rotatable bonds :	0
Num. H-bond acceptors :	2.0
Num. H-bond donors :	1.0
Molar Refractivity :	41.02
TPSA :	28.68 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.8 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.39
Log Po/w (XLOGP3) :	1.99
Log Po/w (WLOGP) :	2.43
Log Po/w (MLOGP) :	1.75
Log Po/w (SILICOS-IT) :	2.9
Consensus Log Po/w :	2.09

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.63
Solubility :	0.352 mg/ml ; 0.00234 mol/l
Class :	Soluble
Log S (Ali) :	-2.22
Solubility :	0.908 mg/ml ; 0.00605 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.56
Solubility :	0.0415 mg/ml ; 0.000277 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.71

Safety of [ 118469-15-1 ]

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

Application In Synthesis of [ 118469-15-1 ]

* 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 [ 118469-15-1 ]
Downstream synthetic route of [ 118469-15-1 ]

[ 118469-15-1 ] Synthesis Path-Upstream 1~10

1
[ 57-55-6 ]
[ 367-31-7 ]
[ 118469-15-1 ]
[ 1977-72-6 ]

Reference： [1] Bulletin of the Chemical Society of Japan, 2010, vol. 83, # 7, p. 831 - 837

2
[ 1445-45-0 ]
[ 364-78-3 ]
[ 118469-15-1 ]

Yield	Reaction Conditions	Operation in experiment
80%	With indium; acetic acid In ethyl acetate for 4 h; Reflux; Inert atmosphere	General procedure: 2-Nitroaniline derivative (1 mmol) was added to a mixture of indium powder (574 mg, 5.0 mmol for 2-nitroaniline, 918 mg 8.0 mmol for 1,2-dinitroarene), and acetic acid (0.572 mL, 10 mmol) in ethyl acetate (2 mL), followed by the addition of trimethyl orthoester (2.0 mmol) in ethyl acetate (3 mL for 2-nitroaniline; 8 mL for 1,2-dinitroarene). The reaction mixture was stirred at reflux under a nitrogen atmosphere. After the reaction was completed, the reaction mixture was diluted with ethyl acetate (30 mL), filtered through Celite, poured into 10percent NaHCO₃ (30 mL), and then extracted with ethyl acetate (30 mL.x.3). The combined organic extracts were dried over MgSO₄, filtered, and concentrated. The residue was eluted with ethyl acetate/hexane (v/v=10/90) for 2-phenylbenzimidazole derivatives or methanol/dichloromethane (v/v=1/99) for 2-methylbenzimidazole derivatives through a silica gel column to give the corresponding benzimidazoles. The structures of the benzimidazoles were characterized by ¹H NMR, ¹³C NMR, FTIR, and GC-MS, and were mostly known compounds. HRMS data were reported in addition for unknown compounds.

Reference： [1] Tetrahedron, 2011, vol. 67, # 41, p. 8027 - 8033

3
[ 367-31-7 ]
[ 123-54-6 ]
[ 118469-15-1 ]

Reference： [1] Patent: WO2008/137027, 2008, A2, . Location in patent: Page/Page column 81-82

4
[ 1445-45-0 ]
[ 367-31-7 ]
[ 118469-15-1 ]

Reference： [1] Journal of the American Chemical Society, 2014, vol. 136, # 11, p. 4287 - 4299
[2] Patent: WO2017/222951, 2017, A1, . Location in patent: Page/Page column 84

5
[ 367-31-7 ]
[ 2208-07-3 ]
[ 118469-15-1 ]

Reference： [1] Patent: US5180723, 1993, A,

6
[ 64-17-5 ]
[ 364-78-3 ]
[ 118469-15-1 ]

Reference： [1] RSC Advances, 2016, vol. 6, # 76, p. 72750 - 72755
[2] Synthetic Communications, 2012, vol. 42, # 10, p. 1500 - 1508

7
[ 141-82-2 ]
[ 367-31-7 ]
[ 118469-15-1 ]

Reference： [1] Organic and Biomolecular Chemistry, 2018, vol. 16, # 8, p. 1337 - 1342

8
[ 57-55-6 ]
[ 367-31-7 ]
[ 118469-15-1 ]
[ 1977-72-6 ]

Reference： [1] Bulletin of the Chemical Society of Japan, 2010, vol. 83, # 7, p. 831 - 837

9
[ 64-17-5 ]
[ 367-31-7 ]
[ 615-15-6 ]
[ 118469-15-1 ]

Reference： [1] Bulletin of the Chemical Society of Japan, 2010, vol. 83, # 7, p. 831 - 837

10
[ 367-31-7 ]
[ 64-19-7 ]
[ 118469-15-1 ]

Reference： [1] Journal of the American Chemical Society, 2017, vol. 139, # 24, p. 8267 - 8276

[ 118469-15-1 ] Synthesis Path-Downstream 1~33

Yield	Reaction Conditions	Operation in experiment
80.4%		B. 2-Methyl-5-fluorobenzimidazole Iron (Fe) (176.75 mmole, 9.87 g) is added to a solution of 4-fluoro-2-nitrophenyl-N-acetamide (35.35 mmole, 7.5 g) in acetic acid (160 ml) and the mixture is refluxed for one hour and is stirred at room temperature over night. The solvent is evaporated. The residue is extracted with ethylacetate and is washed with saturated NaHCO3. The organic layer is washed with water, dried with NaSO4, is filtered and evaporated. Recrystallisation in ethylacetate gives the title compound (80.4%).

2
[ 118469-15-1 ]
[ 1133-49-9 ]
[ 1026534-16-6 ]

Yield	Reaction Conditions	Operation in experiment
	In dichloromethane; 2,4-dichlorophenoxyacetic acid dimethylamine; mineral oil;	C. 2-Methyl-5-fluoro-1-(3,4,5-trimethoxybenzyl) benzimidazole Sodium hydride (18.31 mmole, 0.44 g, 60% in mineral oil) is added in small amounts under nitrogen to an ice cooled solution of <strong>[118469-15-1]2-methyl-5-fluorobenzimidazole</strong> (16.64 mmole, 2.5 g) in dry DMA (9 ml). The mixture is stirred at the same temperature for 30 minutes. Trimethoxybenzyl chloride (18.31 mmole, 3.97 g) in DMA (4 ml) is added in several portions and the mixture is allowed to stir at room temperature over night. The reaction mixture is poured on to ice, the precipitate is collected and dissolved in dichloromethane. The organic solution is washed several times with water, is dried with Na2SO4, is filtered and is evaporated. (R1=3,4,5-trimethoxybenzyl, R2=CH3, R3=F, n=1, y=0)

Reference： [1]Patent: US6348032,2002,B1

3
[ 367-31-7 ]
[ 2208-07-3 ]
[ 118469-15-1 ]

Yield	Reaction Conditions	Operation in experiment
51%	In ethanol;	(a) 2-Methyl-5-fluorobenzimidazole Ethyl acetimidate hydrochloride (37.1 g, 0.3 mol) was added to a stirred suspension of 4-fluoro-ortho-phenylenediamine (12.6 g, 0.1 mol) in ethanol (150 ml) at 0 C. The mixture was allowed to warm up to room temperature and stirred overnight. The solvent was removed under reduced pressure and the residue extracted into ethyl acetate (100 ml), washed with water (3*100 ml), dried over anhydrous magnesium sulphate, filtered and evaporated. Crystallisation from ethyl acetate gave 2-methyl-5-fluorobenzimidazole (7.7 g, 51%) as a brown crystalline solid. m.p. 177-178 C. deltaH 7.46 (1H, dd, J 8.8, 4.7 Hz), 7.22 (1H, dd, J 8.9, 2.4 Hz), 6.98 (1H, ddd, J 9.7, 8.9, 2.4 Hz), 2.65 (3H, s).

Reference： [1]Patent: US5180723,1993,A

4
[ 367-31-7 ]
[ 123-54-6 ]
[ 118469-15-1 ]

Yield	Reaction Conditions	Operation in experiment
		Under an N2 atmosphere, 4-fluorobenzene-l,2-diamine (5.0Og, 39.6 mmol) was suspended in EtOH (220 <n="84"/>mL) and 5M HCl (16OmL) was added. The reaction was warmed to 50C and 2,4- pentandione (8.14mL, 7.93mmol) was added and the reaction was heated to reflux for 30 min. Upon cooling to room temperature, the reaction was neutralized with a saturated solution of NaHCO3(aq) and extracted with dichloromethane. The layers were separated and the aqueous layer was washed with additional dichloromethane (2x). The organics were then combined, dried (Na2SO4), filtered and concentrated in vacuo. The resulting solid was triturated with dichloromethane to afford the title compound. 1H NMR (400MHz) (DMSO-d6) delta 7.43-7.19 (bm, 2H); 6.92 (bs, IH); 2.44 (s, 3H).

Reference： [1]Patent: WO2008/137027,2008,A2 .Location in patent: Page/Page column 81-82

5
[ 118469-15-1 ]
[ 1080522-29-7 ]
[ 1080522-30-0 ]

Yield	Reaction Conditions	Operation in experiment
		Under an N2 atmosphere, 5-fluoro-2- methyl-lH-benzo[d]imidazole (5.21 g, 34.7mmol) was dissolved in concentrated sulfuric acid (25 mL) and cooled to 0 C. Nitric acid (25 mL) was added and the reaction was stirred at 0 C for 1 h. The reaction was poured over ice and neutralized with IN NaOH. The mixture was extracted with ethyl acetate (3x). The organics were combined, dried (Na2SO4), filtered and concentrated in vacuo. The residue was triturated with 10% MeOH in dichloromethane to afford l.OOg of 5-fluoro-2-methyl-6-nitro-lH-benzo[d]imidazole after filtration. The filtrate was flash column chromatographed, eluting with 2% to 7% MeOH in dichloromethane, to afford 5-fluoro-2-methyl-4-nitro-lH-benzo[d]imidazole. LC- MS ESI (pos.) m/z: 196.0 (M+H).

Reference： [1]Patent: WO2008/137027,2008,A2 .Location in patent: Page/Page column 82

6
[ 2369-11-1 ]
[ 78-39-7 ]
[ 118469-15-1 ]

Yield	Reaction Conditions	Operation in experiment
94%	With 10% Pd/C; hydrogen; acetic acid In methanol at 20℃;

Reference： [1]Location in patent: scheme or table Liu, Zheng; Li, Haihong; Zhao, Qingjie; Shen, Jingshan [Heterocycles, 2008, vol. 75, # 8, p. 1907 - 1911]

7
[ 57-55-6 ]
[ 367-31-7 ]
[ 118469-15-1 ]
[ 1977-72-6 ]

Reference： [1]Bulletin of the Chemical Society of Japan,2010,vol. 83,p. 831 - 837

8
[ 64-17-5 ]
[ 367-31-7 ]
[ 615-15-6 ]
[ 118469-15-1 ]

Reference： [1]Bulletin of the Chemical Society of Japan,2010,vol. 83,p. 831 - 837

9
[ 1445-45-0 ]
[ 364-78-3 ]
[ 118469-15-1 ]

Yield	Reaction Conditions	Operation in experiment
80%	With indium; acetic acid; In ethyl acetate; for 4.0h;Reflux; Inert atmosphere;	General procedure: 2-Nitroaniline derivative (1 mmol) was added to a mixture of indium powder (574 mg, 5.0 mmol for 2-nitroaniline, 918 mg 8.0 mmol for 1,2-dinitroarene), and acetic acid (0.572 mL, 10 mmol) in ethyl acetate (2 mL), followed by the addition of trimethyl orthoester (2.0 mmol) in ethyl acetate (3 mL for 2-nitroaniline; 8 mL for 1,2-dinitroarene). The reaction mixture was stirred at reflux under a nitrogen atmosphere. After the reaction was completed, the reaction mixture was diluted with ethyl acetate (30 mL), filtered through Celite, poured into 10% NaHCO3 (30 mL), and then extracted with ethyl acetate (30 mL×3). The combined organic extracts were dried over MgSO4, filtered, and concentrated. The residue was eluted with ethyl acetate/hexane (v/v=10/90) for 2-phenylbenzimidazole derivatives or methanol/dichloromethane (v/v=1/99) for 2-methylbenzimidazole derivatives through a silica gel column to give the corresponding benzimidazoles. The structures of the benzimidazoles were characterized by 1H NMR, 13C NMR, FTIR, and GC-MS, and were mostly known compounds. HRMS data were reported in addition for unknown compounds.

Reference： [1]Tetrahedron,2011,vol. 67,p. 8027 - 8033

10
[ 64-17-5 ]
[ 364-78-3 ]
[ 118469-15-1 ]

Reference： [1]RSC Advances,2016,vol. 6,p. 72750 - 72755
[2]Synthetic Communications,2012,vol. 42,p. 1500 - 1508

11
[ 118469-15-1 ]
[ 73183-34-3 ]
[ 1573171-35-3 ]

Reference： [1]Journal of the American Chemical Society,2014,vol. 136,p. 4287 - 4299

12
[ 1445-45-0 ]
[ 367-31-7 ]
[ 118469-15-1 ]

Yield	Reaction Conditions	Operation in experiment
	In methanol; at 60℃; for 12.0h;	(0618) A mixture of 1,1,1-trimethoxyethane (19.0 g, 159 mmol) and 4-fluorobenzene-1,2-diamine (2.00 g, 15.9 mmol) in MeOH (10 mL) was stirred at 60 C for 12 h. After cooling to ambient temperature, the mixture was concentrated. The residue was purified by flash silica gel chromatography (ISCO; 40 g SepaFlash Silica Flash Column, Eluent of 50100% EA/PE gradient (at) 40 mL/min) to give 5-fluoro-2-methyl-1H-benzo[d]imidazole as a solid.

Reference： [1]Journal of the American Chemical Society,2014,vol. 136,p. 4287 - 4299
[2]Patent: WO2017/222951,2017,A1 .Location in patent: Page/Page column 84

13
[ 118469-15-1 ]
[ 98-59-9 ]
5-fluoro-2-methyl-1-tosyl-1H-benzo[d]imidazole [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2017,vol. 139,p. 8267 - 8276

14
[ 367-31-7 ]
[ 64-19-7 ]
[ 118469-15-1 ]

Reference： [1]Journal of the American Chemical Society,2017,vol. 139,p. 8267 - 8276

15
[ 141-82-2 ]
[ 367-31-7 ]
[ 118469-15-1 ]

Reference： [1]Organic and Biomolecular Chemistry,2018,vol. 16,p. 1337 - 1342

16
[ 118469-15-1 ]
C₁₁H₁₃NO₄S [ No CAS ]
C₁₉H₂₀FN₃O₄S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
69.4%		In a 150 mL round-bottom flask, the benzimidazole compound represented by Formula III (R1 is methyl, R2 is H, R3 is fluorine) (0.306 g, 2.04 mmol) was added, and potassium carbonate was used as the base (0.324 g, 2.35). Acetonitrile was stirred as a solvent at 70C for 30 minutes, cooled to room temperature, compound II (0.400 g, 1.57 mmol) was added, and the temperature was raised to 70C. The reaction was followed by thin layer chromatography to complete the reaction. After concentration, extraction, column chromatography, drying and other post-treatments, compound IV-12 (0.441 g) was obtained with a yield of 69.4%.

Reference： [1]Patent: CN107721933,2018,A .Location in patent: Paragraph 0084-0086

17
[ 118469-15-1 ]
[ 105942-09-4 ]
3-fluoro-4-((5-fluoro-2-methyl-1H-benzo[d]imidazol-1-yl)methyl)benzonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In N,N-dimethyl-formamide; at 16℃; for 16h;	(0621) A mixture of 4-(bromomethyl)-3-fluorobenzonitrile (499 mg, 2.33 mmol) and 5-fluoro-2- methyl-1H-benzo[d]imidazole (350 mg, 2.33 mmol) in DMF (15 mL) was stirred at 16 C for 16 h. The mixture was washed with water (50 mL) and extracted with EtOAc (3 x 30 mL). The collected organic layers were washed with brine (30 mL) and dried over anhydrous Na2SO4. The mixure was filtered and the filtrate was concentrated to get the crude product. The crude product was purified by reverse-phase Prep-HPLC (preparative HPLC on a GILSON 281 instrument fitted with Phenomenex Synergi C18 250x21.2mmx4um using water and acetonitrile as the eluents. Mobile phase A: water, mobile phase B: acetonitrile (containing: 0.1%TFA-ACN). Gradient: 35-65%, 0-10 min; 100% B, 10.5-12.5min; 5% B, 13-15min) to give 3-fluoro-4-((5- fluoro-2-methyl-1H-benzo[d]imidazol-1-yl)methyl)benzonitrile as an oil. ESI-MS m/z [M + H]+ : 284.0.

Reference： [1]Patent: WO2017/222951,2017,A1 .Location in patent: Page/Page column 85

18
[ 118469-15-1 ]
(Z)-3-fluoro-4-((5-fluoro-2-methyl-1H-benzo[d]imidazol-1-yl)methyl)-N'-hydroxybenzimidamide [ No CAS ]

Reference： [1]Patent: WO2017/222951,2017,A1

19
[ 118469-15-1 ]
3-(3-fluoro-4-((5-fluoro-2-methyl-1H-benzo[d]imidazol-1-yl)methyl)phenyl)-5-(trifluoromethyl)-1,2,4-oxadiazole [ No CAS ]

Reference： [1]Patent: WO2017/222951,2017,A1

20
[ 118469-15-1 ]
[ 1080522-40-2 ]
[ 1080522-39-9 ]