61150-58-1|2-(2-Bromo-4-fluorophenyl)acetonitrile| Ambeed

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Quality Control of [ 61150-58-1 ] Purity: 98% SDS Specification

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Product Details of [ 61150-58-1 ]

CAS No. :	61150-58-1
Formula :	C₈H₅BrFN
M.W :	214.03
SMILES Code :	N#CCC1=CC=C(F)C=C1Br
MDL No. :	MFCD04115829
InChI Key :	OITVZXQQQFKXIP-UHFFFAOYSA-N
Pubchem ID :	826392

Safety of [ 61150-58-1 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H332-H335
Precautionary Statements:	P261-P280-P305+P351+P338

Computational Chemistry of [ 61150-58-1 ] Show Less

Physicochemical Properties

Num. heavy atoms	11
Num. arom. heavy atoms	6
Fraction Csp3	0.12
Num. rotatable bonds	1
Num. H-bond acceptors	2.0
Num. H-bond donors	0.0
Molar Refractivity	43.62
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	23.79 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.91
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	2.37
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	3.07
Log P_o/w (MLOGP)? MLOGP: Topological method implemented from Moriguchi I. et al. 1992 Chem. Pharm. Bull. Moriguchi I. et al. 1994 Chem. Pharm. Bull. Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.	2.94
Log P_o/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	3.22
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.7

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-3.0
Solubility	0.215 mg/ml ; 0.00101 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-2.51
Solubility	0.661 mg/ml ; 0.00309 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-4.03
Solubility	0.0202 mg/ml ; 0.0000942 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Moderately soluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	High
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	Yes
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) and tested on 415 molecules (test set) 10-fold CV: ACC=0.72 / AUC=0.77 External: ACC=0.88 / AUC=0.94	No
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.83 / AUC=0.90 External: ACC=0.84 / AUC=0.91	Yes
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.80 / AUC=0.86 External: ACC=0.80 / AUC=0.87	No
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) and tested on 2075 molecules (test set) 10-fold CV: ACC=0.78 / AUC=0.85 External: ACC=0.71 / AUC=0.81	No
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) and tested on 1068 molecules (test set) 10-fold CV: ACC=0.79 / AUC=0.85 External: ACC=0.81 / AUC=0.87	No
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) and tested on 2579 molecules (test set) 10-fold CV: ACC=0.77 / AUC=0.85 External: ACC=0.78 / AUC=0.86	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-5.92 cm/s

Druglikeness

Lipinski? Lipinski (Pfizer) filter: implemented from Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev. MW ≤ 500 MLOGP ≤ 4.15 N or O ≤ 10 NH or OH ≤ 5	0.0
Ghose? Ghose filter: implemented from Ghose AK. et al. 1999 J. Comb. Chem. 160 ≤ MW ≤ 480 -0.4 ≤ WLOGP ≤ 5.6 40 ≤ MR ≤ 130 20 ≤ atoms ≤ 70	None
Veber? Veber (GSK) filter: implemented from Veber DF. et al. 2002 J. Med. Chem. Rotatable bonds ≤ 10 TPSA ≤ 140	0.0
Egan? Egan (Pharmacia) filter: implemented from Egan WJ. et al. 2000 J. Med. Chem. WLOGP ≤ 5.88 TPSA ≤ 131.6	0.0
Muegge? Muegge (Bayer) filter: implemented from Muegge I. et al. 2001 J. Med. Chem. 200 ≤ MW ≤ 600 -2 ≤ XLOGP ≤ 5 TPSA ≤ 150 Num. rings ≤ 7 Num. carbon > 4 Num. heteroatoms > 1 Num. rotatable bonds ≤ 15 H-bond acc. ≤ 10 H-bond don. ≤ 5	1.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.55

Medicinal Chemistry

PAINS? Pan Assay Interference Structures: implemented from Baell JB. & Holloway GA. 2010 J. Med. Chem.	0.0 alert
Brenk? Structural Alert: implemented from Brenk R. et al. 2008 ChemMedChem	0.0 alert: heavy_metal
Leadlikeness? Leadlikeness: implemented from Teague SJ. 1999 Angew. Chem. Int. Ed. 250 ≤ MW ≤ 350 XLOGP ≤ 3.5 Num. rotatable bonds ≤ 7	No; 1 violation:MW<1.0
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties, trained on 12'782'590 molecules and tested on 40 external molecules (r² = 0.94)	1.49

Application In Synthesis of [ 61150-58-1 ]

* 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.

Downstream synthetic route of [ 61150-58-1 ]

[ 61150-58-1 ] Synthesis Path-Downstream 1~35

1
[ 61150-57-0 ]
[ 143-33-9 ]
[ 61150-58-1 ]

References: [1]Collection of Czechoslovak Chemical Communications,1977,vol. 42,p. 3079 - 3093.

2
[ 61150-58-1 ]
[ 61150-59-2 ]

Yield	Reaction Conditions	Operation in experiment
	With dihydrogen peroxide; sodium hydroxide; In ethanol; water; for 24h;Reflux;	To a solution of s2 in EtOH (10.0 mL) and H2O (5.0 mL) were successively added NaOH (2.94 g,73.5 mmol) and aqueous H2O2 (23 muL, 0.736 mmol) at room temperature. After the mixture washeated to reflux for 24 h, the reaction was quenched by addition of conc. HCl at 0 C. The crudemixture was extracted with EtOAc (x4) and the combined organic extracts were washed with brine,dried (Na2SO4), and concentrated in vacuo to give crude s3 (1.62 g) as pale yellow solid. Thiscrude material was used for next reaction without further purification.

References: [1]Synlett,2011,p. 2525 - 2528.
[2]Collection of Czechoslovak Chemical Communications,1977,vol. 42,p. 3079 - 3093.
[3]Journal of the American Chemical Society,2018,vol. 140,p. 6203 - 6207.
[4]Chemistry Letters,2018,vol. 47,p. 868 - 871.

Yield	Reaction Conditions	Operation in experiment
21 g (96%)		Sodium cyanide (7.5 g) is added to a solution of the bromide from the preceding preparation (27.4 g) in dimethylformamide (40 ml) under external cooling with cold water and the mixture is stirred at room temperature for 3 hours. After standing overnight, the mixture is diluted with large volumes of water and set aside for several hours. The separated product is filtered, washed with water and dried, yielding 21 g (96%) of crude 2-bromo-4-fluorophenylacetonitrile which is crystallized from cyclohexane.

4
[ 1422-53-3 ]
[ 61150-58-1 ]

References: [1]Collection of Czechoslovak Chemical Communications,1977,vol. 42,p. 3079 - 3093.
[2]Synlett,2011,p. 2525 - 2528.

5
[ 61150-58-1 ]
[ 65999-41-9 ]

References: [1]Collection of Czechoslovak Chemical Communications,1977,vol. 42,p. 3079 - 3093.

6
[ 61150-58-1 ]
[ 56096-99-2 ]

References: [1]Collection of Czechoslovak Chemical Communications,1977,vol. 42,p. 3079 - 3093.

7
[ 61150-58-1 ]
[ 74-88-4 ]
[ 1086599-47-4 ]

Yield	Reaction Conditions	Operation in experiment
65%		Add sodium hydride (1 g, 42.1 mmol) to a stirred solution of (2-bromo-4- fluoro-phenyl)-acetonitrile (3 g, 14 mmol) in 10 mL of dimethyl formamide (DMF) at 0 0C. Stir the mixture at 0 0C to RT for half an hour. Add methyl iodide (6 g, 42 mmol). Stir for another 30 min. Quench the reaction with water. Extract the product into DCM. Dry the organic phase over sodium sulfate and concentrate to give an oily residue. Purify the residue by flash column chromatography (FCC) (hexane to 20 % ethyl acetate in hexane as gradient elute) to give the title compound as a white solid (2.2 g, 65 %). 1H NMR (400 MHz, CDCl3) delta 7.41-7.47 (m, 2H), 7.03-7.08 (m, IH), 1.88 (s, 6H).

References: [1]Patent: WO2008/144223,2008,A2 .Location in patent: Page/Page column 13.

8
[ 61150-58-1 ]
[ 109-64-8 ]
[ 1086599-29-2 ]

Yield	Reaction Conditions	Operation in experiment
31%	With potassium hydroxide;tetrabutylammomium bromide; In toluene; at 100℃; for 2h;	Add potassium hydroxide (8.39 g, 150 mmol) and tetrabutylamine bromide(0.3 g, catalytic) to a solution of <strong>[61150-58-1]2-<strong>[61150-58-1](2-bromo-4-fluorophenyl)acetonitrile</strong></strong> (4 g, 18.69 mmol) and 1,3-dibromopropane (4.15 g, 20.5 mmol) in toluene (20 mL). Stir it at 100 0C temperature for 2 h. Dilute the mixture with water and extract with ethyl acetate. Wash the organic layer with 1 N HCl and aqueous saturated sodium chloride. Dry over magnesium sulfate. Remove the organic solvent to give the crude product.Distill to give l-(2-bromo-4-fluorophenyl)cyclobutanecarbonitrile (boiling point 110- 120 C/0.3 Torr.) (1.5 g, 31 %). MS (GC) m/z 253 [M]+.Add 6 mL of HCl saturated methanol to the above solid and stir overnight. Evaporate the solvent to dry. Add NaHCO3 (1 M, 30 mL) and ether (20 mL). Stir for 15 min. Separate the organic layer and extract the aqueous layer with ether. Combine the ether solution and remove the solvent. Dissolve the residue in methanol (10 mL) and KOH (1.5 g) and stir over the weekend. Remove methanol and add water (30 mL). Extract with ethyl acetate and then acidify the aqueous layer with HCl. Extract the acidic solution with ethyl acetate, dry over MgSO4, and remove the solvent to give the title compound (1.0 g, 24 %). MS (ES) m/z 271 [M-I]".

References: [1]Patent: WO2008/144223,2008,A2 .Location in patent: Page/Page column 17.

9
[ 75-15-0 ]
[ 61150-58-1 ]
[ 74-88-4 ]
[ 1012327-04-6 ]

References: [1]Organic Letters,2008,vol. 10,p. 965 - 968.

10
[ 556-56-9 ]
[ 61150-58-1 ]
[ 1071838-67-9 ]

References: [1]Journal of Organic Chemistry,2008,vol. 73,p. 8452 - 8457.

11
[ 75-15-0 ]
[ 61150-58-1 ]
[ 74-88-4 ]
[ 1174642-53-5 ]