53312-82-6|4-Amino-2-bromobenzonitrile| Ambeed

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Quality Control of [ 53312-82-6 ] Purity: 98% SDS Specification

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Product Details of [ 53312-82-6 ]

CAS No. :	53312-82-6
Formula :	C₇H₅BrN₂
M.W :	197.03
SMILES Code :	N#CC1=CC=C(N)C=C1Br
MDL No. :	MFCD03695814
InChI Key :	OSYGPHDNNWRFJO-UHFFFAOYSA-N
Pubchem ID :	824602

Safety of [ 53312-82-6 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H312-H315-H319-H332
Precautionary Statements:	P280-P305+P351+P338

Computational Chemistry of [ 53312-82-6 ] Show Less

Physicochemical Properties

Num. heavy atoms	10
Num. arom. heavy atoms	6
Fraction Csp3	0.0
Num. rotatable bonds	0
Num. H-bond acceptors	1.0
Num. H-bond donors	1.0
Molar Refractivity	43.26
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	49.81 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.46
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	1.65
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.91
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.	1.55
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	1.76
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.67

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.55
Solubility	0.562 mg/ml ; 0.00285 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.	-2.31
Solubility	0.966 mg/ml ; 0.0049 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	-2.98
Solubility	0.206 mg/ml ; 0.00104 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	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	Yes
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-6.33 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	1.0 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)	1.69

Application In Synthesis of [ 53312-82-6 ]

* 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.

Downstream synthetic route of [ 53312-82-6 ]

[ 53312-82-6 ] Synthesis Path-Downstream 1~35

1
[ 36282-26-5 ]
[ 53312-82-6 ]

Yield	Reaction Conditions	Operation in experiment
49%		To a 40 mL reaction vial with a stir bar are added 2-bromo-4-fluorobenzonitrile (6.00 g, 30.0 mmol) and 3,4,5-trimethoxybenzylamine (5.4 mL, 32 mmol). The reaction is sealed and stirred at 140 C. for 1 hour. The reaction is cooled to room temperature, and CH2Cl2 (15 mL) and trifluoroacetic acid (15 mL) are added. The vial is sealed and the mixture is allowed to stir at room temperature for 24 hours. The reaction is concentrated, diluted with EtOAc (100 mL), washed with saturated aqueous NaHCO3 (2*100 mL), and dried over Na2SO4. The compound is purified by gradient flash chromatography, eluding with 0% to 40% EtOAc in hexanes to yield 4-amino-2-bromobenzonitrile as a tan solid (2.88 g, 49% yield) (LC/MS m/z=197 [M+H]+).

References: [1]Patent: US2008/76813,2008,A1 .Location in patent: Page/Page column 26.
[2]Bioorganic and Medicinal Chemistry,2013,vol. 21,p. 993 - 1005.

2
[ 108-31-6 ]
[ 53312-82-6 ]
[ 108-94-1 ]
[ 1008714-30-4 ]

Yield	Reaction Conditions	Operation in experiment
38%	at 150℃; for 16h;	To a 40 mL vial with a stir bar are added <strong>[53312-82-6]4-amino-2-bromobenzonitrile</strong> (637 mg, 3.23 mmol), maleic anhydride (317 mg, 3.23 mmol), and cyclohexanone (1.70 mL, 16.2 mmol). The reaction is heated to 150 C. for 16 hours then cooled to room temperature. The product is purified by gradient flash chromatography eluding with 0% to 10% MeOH in CH2Cl2 to provide [1-(3-bromo-4-cyanophenyl)-2-oxo-2,4,5,6,7,7a-hexahydro-1H-indol-3-yl]-acetic acid as a tan solid (456 mg, 38% yield) (LC/MS m/z=375 [M+H]+).

References: [1]Patent: US2008/76813,2008,A1 .Location in patent: Page/Page column 26.

3
[ 53312-82-6 ]
[ 411235-57-9 ]
[ 1006899-23-5 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium phosphate;bis-triphenylphosphine-palladium(II) chloride; In ethanol; water; toluene; at 80℃; for 19h;	To a stirred mixture of <strong>[53312-82-6]4-amino-2-bromobenzonitrile</strong> (2.00 g, 10.2 mmol), cyclopropyl boronic acid (1,18 g, 13.7 mmol) and K3PO4 (3.23 g, 15.2 mmol) in the mixed solvents of EtOH/H2O/toluene (2 mL/2 mL/12 mL) under nitrogen was added PdCl2(PPh3)2 (0.72 g, 1.03 mmol). This mixture was heated at 800C for 19 h and cooled to room temperature. Next, the mixture was diluted with 150 mL of EtOAc and filtered through a pad of silica gel topped with a layer of celite. This pad was further rinsed with EtOAc (2 x 100 mL). The filtrate was washed with 25 mL of brine, dried over MgSO4, filtered and concentrated in vacuo to give the crude amine. The crude amine was purified by an ISCO auto flash chromatographer using 12O g silica gel column, eluted with hexanes/CH2Cl2 solvents in a 25 min 50% to 100% gradient elution to give 0.75 g of Preparation 4OA as a white solid in 47% yield. [00428] HPLC: 1.55 min (RT) (Chromolith SpeedROD column 4.6 x 50 mm, 10- 90% aqueous MeOH over 4 minutes containing 0.2% phosphoric acid, 4 mL/min, monitoring at 220 nm). MS (ES): m/z=159 [M+H]+. 1H NMR of 4-amino-2- cyclopropyl-benzonitrile (400 MHz, CDCl3) delta ppm 7.34 (d, J=8.31 Hz, 1 H) 6.44 (dd, J=8.31, 2.27 Hz, 1 H) 6.12 (d, J=2.01 Hz, 1 H) 4.01 (s, 2 H) 2.13-2.24 (m, 1 H) 1.02- 1.12 (m, 2 H) 0.68-0.76 (m, 2 H).

References: [1]Patent: WO2009/3077,2008,A1 .Location in patent: Page/Page column 116.

4
[ 34662-35-6 ]
[ 53312-82-6 ]

Yield	Reaction Conditions	Operation in experiment
	With iron; acetic acid; In ethyl acetate; at 80℃; for 4h;	To a solution of Preparation 66B (8.39 g, 37.12 mmol) in acetic acid (42 mL) and EtOAc (42 mL) maintained at 800C, iron powder (8.3 g, 150.3 mmol) was added with mechanical stirring. The reaction mixture was maintained at 800C until all starting material was consumed (4 h). The reaction mixture was cooled, filtered through Celite and the residue was washed with EtOAc. The filtrate was then neutralized with sat. NaHCtheta3 and the organic layer was washed with water, brine, dried over sodium sulfate, and concentrated in vacuo to yield Preparation 66C (6.5 g) as an off white solid. No purification was necessary. <n="141"/>[00510] HPLC: 4.22 minutes (RT) (Eclipse XDB C18 column, 4.6 x 150 mm eluting with 50-90% aqueous acetonitrile over 15 minutes (0.0 IM ammonium acetate), 1.0 mL/min, monitoring at 280 nm).

References: [1]European Journal of Organic Chemistry,2012,p. 275 - 280.
[2]Patent: WO2009/3077,2008,A1 .Location in patent: Page/Page column 139-140.

5
[ 53312-82-6 ]
[ 1201684-65-2 ]

Yield	Reaction Conditions	Operation in experiment
		40 mg CuCI were dissolved in 10 m I water and cooled in an ice bath to 00C. 1.6 ml thionylchloride were added dropwise. The reaction solution was allowed to warm to roomtemperature overnight.1.O g 4-Amino-2-bromo-benzonitrile were suspended in 12 ml hydrochlorc acid and 45 ml water and warmed to 960C until all 4-Amino-2-bromo-benzonitrile were dissolved. The solution was cooled to -5C and 380 mg NaNO2 dissolved in 10 ml water were added. Then the thionlychloride solution was cooled to -2C and added dropwise. The <n="89"/>3-Bromo-4-cyano-benzenesulfonyl chloride precipitated and was collected by filtration and washed with ice cooled water and dried under vacuo to obtain 956 mg 3-Bromo-4- cyano-benzenesulfonyl chloride as a solid. This material was used without further purification. C7H3BrCINO2S (280.53).

References: [1]Patent: WO2009/149820,2009,A1 .Location in patent: Page/Page column 87-88.

6
[ 53312-82-6 ]
[ 1220099-40-0 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 1712 - 1717.

7
[ 1220099-39-7 ]
[ 53312-82-6 ]

Yield	Reaction Conditions	Operation in experiment
85%	With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; water; at 20℃; for 3.5h;	2,3-Dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) (2.90 g, 12.8 mmol) was added to a stirred solution of 25 (4.03 g, 12.8 mmol) in CH2Cl2 (85 mL) and H2O (43 mL) at rt. The reaction mixture was stirred for 3.5 h, and then filtered to remove precipitated solids. The filtrate was added to satd NaHCO3 aq, and extracted with CH2Cl2. The organic layer was dried over MgSO4 and concentrated. The resulting residue was purified by silica gel chromatography (hexane/AcOEt = 2/1) to afford 26 (2.13 g, 10.8 mmol, 85%) as a white solid.

References: [1]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 1712 - 1717.
[2]Bioorganic and Medicinal Chemistry,2013,vol. 21,p. 993 - 1005.

8
[ 50-00-0 ]
[ 53312-82-6 ]
[ 1189353-62-5 ]

References: [1]European Journal of Organic Chemistry,2012,p. 275 - 280.

9
[ 13296-94-1 ]
[ 53312-82-6 ]

References: [1]European Journal of Organic Chemistry,2012,p. 275 - 280.
[2]Patent: WO2009/3077,2008,A1 .

10
[ 53312-82-6 ]
[ 24424-99-5 ]
[ 1425822-14-5 ]

Yield	Reaction Conditions	Operation in experiment
6%	With dmap; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at 0℃; for 2h;Reflux;	Di-tert-butyl dicarbonate (Boc2O) (24.6 g, 113 mmol) in THF (75 mL), 4-dimethylaminopyridine (DMAP) (532 mg, 4.35 mmol) and diisopropylethylamine (DIPEA) (35.0 mL, 201 mmol) were added to a solution of 26 (7.70 g, 39.1 mmol) at 0 C. The reaction mixture was refluxed for 2 h, then cooled to rt, and concentrated to about 30 mL H2O and brine were added to it, and the mixture was extracted with AcOEt. The organic layer was dried over MgSO4 and concentrated. The resulting residue was recrystallized from hexane/AcOEt to afford 27 (8.40 g, 21.1 mmol, 54%) as white cubic crystals. The mother liquor was concentrated and the residue was purified by silica gel chromatography (hexane/AcOEt = 6/1) and reprecipitation (from EtOH) to afford 27 (899 mg, 2.26 mmol, 6%) as a white solid