89891-69-0|3-Bromo-4-formylbenzonitrile| Ambeed

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Quality Control of [ 89891-69-0 ] Purity: 97% SDS Specification

COA

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NMR

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CNMR

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Product Details of [ 89891-69-0 ]

CAS No. :	89891-69-0
Formula :	C₈H₄BrNO
M.W :	210.03
SMILES Code :	BrC1=C(C=O)C=CC(=C1)C#N
MDL No. :	MFCD09261031
InChI Key :	ADHKMYHLJHBOKB-UHFFFAOYSA-N
Pubchem ID :	20510518

Safety of [ 89891-69-0 ]

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

Computational Chemistry of [ 89891-69-0 ] Show Less

Physicochemical Properties

Num. heavy atoms	11
Num. arom. heavy atoms	6
Fraction Csp3	0.0
Num. rotatable bonds	1
Num. H-bond acceptors	2.0
Num. H-bond donors	0.0
Molar Refractivity	44.24
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	40.86 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.57
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	2.38
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	2.13
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.	1.51
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	2.63
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.04

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.98
Solubility	0.22 mg/ml ; 0.00105 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.	-2.88
Solubility	0.278 mg/ml ; 0.00132 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	-3.29
Solubility	0.107 mg/ml ; 0.000512 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	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-5.89 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	0.0
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)	1.74

Application In Synthesis of [ 89891-69-0 ]

* 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 [ 89891-69-0 ]

[ 89891-69-0 ] Synthesis Path-Downstream 1~35

1
[ 89892-39-7 ]
[ 89891-69-0 ]

References: [1]Journal of Organic Chemistry,1964,vol. 29,p. 2034 - 2036.

2
[ 89891-69-0 ]
[ 90004-92-5 ]

References: [1]Journal of Organic Chemistry,1964,vol. 29,p. 2034 - 2036.

3
[ 89891-69-0 ]
[ 91760-66-6 ]

References: [1]Journal of Organic Chemistry,1964,vol. 29,p. 2034 - 2036.

4
[ 89891-69-0 ]
[ 90221-60-6 ]

References: [1]Journal of Organic Chemistry,1964,vol. 29,p. 2034 - 2036.

5
[ 89891-69-0 ]
[ 90484-53-0 ]

References: [1]Journal of Organic Chemistry,1964,vol. 29,p. 2034 - 2036.

6
[ 42872-74-2 ]
[ 89891-69-0 ]

References: [1]Journal of Organic Chemistry,1964,vol. 29,p. 2034 - 2036.
[2]Patent: WO2013/36869,2013,A2 .

7
[ 89891-69-0 ]
[ 90110-98-8 ]

Yield	Reaction Conditions	Operation in experiment
99%	With sodium tetrahydroborate; In methanol; at 0 - 25℃;	A solution of <strong>[89891-69-0]3-bromo-4-formylbenzonitrile</strong> (1.0 g, 4.8 mmol) in CH3OH (30 niL) was cooled to 00C. NaBH4 (180 mg, 4.8 mmol) was added portionwise. The mixture was allowed to warm to room temperature and stirred at room temperature for 1 h. The mixture was qunched with IN HCl and concentrated under vacuum. The residue was extracted with ethyl acetate (25 mL*3). The combined organic layers were washed with brine (20 mL), dried (Na2SO4) and concentrated under vacuum to give a white solid of the desired compound (1.Og, 99percent). NMR (300 MHz, CDCl3): delta 7.82 (s, IH), 7.49-7.71 (m, 2H), 4.75 (s, 2H). LC-MS: 212 (M + I)+.
99%	With methanol; sodium tetrahydroborate; at 0 - 20℃;	A solution of <strong>[89891-69-0]3-bromo-4-formylbenzonitrile</strong> A (1.0 g, 4.8 mmol) in CH3OH(30 niL) was cooled to 00C. NaBH4 (180 mg, 4.8 mmol) was added portionwise. The mixture was allowed to warm to room temperature and stirr at room temperature for 1 h. The mixture was qunched with IN HCl and concentrated under vacuum. The residue was extracted with ethyl acetate (25 mL*3). The combined organic layers were washed with brine (20 mL), dried (Na2SO4) and concentrated under vacuum to give a white solid of the desired compound B (1.Og, 990Zo)-1H NMR (300 MHz, CDCl3): delta 7.82 (s, IH), 7.49-7.71 (m, 2H), 4.75 (s, 2H). LC-MS: 212 (M + I)+.
60.7%	With methanol; sodium tetrahydroborate; at 0℃; for 0.666667h;	A solution of the product of Part 3B (3.10 g, 14.7 mmol) was dissolved MeOH (74 mL) at ambient temperature then cooled to 0 °C using an ice bath. NaBH4 (0.279 g, 7.38 mmol) was then added in one portion and the resulting solution maintained 40 min at 0 °C. Dilute aqueous HCl was added to consume excess NaBH4 then all volatiles removed in vacuo. The residue was redissolved in EtOAc with transfer to a separatory funnel, successively washed with 5percent aqueous citric acid and H2O, then dried over Na2SO4, filtered and concentrated in vacuo. Purification by chromatography on silica using a step gradient from 9: 1 hexanes/EtOAc to 1 : 1 hexanes/EtOAc afforded the title compound as a white solid (1.90 g, 8.96 mmol; 60.7percent).

References: [1]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 7317 - 7322.
[2]Patent: WO2011/22337,2011,A1 .Location in patent: Page/Page column 102.
[3]Patent: WO2010/45503,2010,A1 .Location in patent: Page/Page column 134.
[4]Patent: WO2013/36869,2013,A2 .Location in patent: Page/Page column 226.

8
[ 1906-82-7 ]
[ 89891-69-0 ]
[ 104291-81-8 ]

References: [1]Tetrahedron Letters,2010,vol. 51,p. 6549 - 6551.

9
[ 89891-69-0 ]
[ 947162-60-9 ]

References: [1]Patent: WO2011/22337,2011,A1 .
[2]Patent: WO2010/45503,2010,A1 .

10
[ 89891-69-0 ]
[ 1221343-14-1 ]

References: [1]Patent: WO2011/22337,2011,A1 .
[2]Patent: WO2010/45503,2010,A1 .

11
[ 89891-69-0 ]
[ 1195621-94-3 ]

References: [1]Patent: WO2011/22337,2011,A1 .

12
[ 89891-69-0 ]
[ 1268336-24-8 ]

References: [1]Patent: WO2011/22337,2011,A1 .

13
[ 89891-69-0 ]
[ 1268336-26-0 ]

References: [1]Patent: WO2011/22337,2011,A1 .

14
[ 89891-69-0 ]
[ 1268336-27-1 ]

References: [1]Patent: WO2011/22337,2011,A1 .

15
[ 89891-69-0 ]
[ 1268336-28-2 ]

References: [1]Patent: WO2011/22337,2011,A1 .

16
2-bromo-4-cyanobenzaldehyde O-methyloxime [ No CAS ]
[ 89891-69-0 ]

References: [1]Journal of Organic Chemistry,2011,vol. 76,p. 6414 - 6420.

17
[ 33499-34-2 ]
[ 89891-69-0 ]

References: [1]Journal of Organic Chemistry,2011,vol. 76,p. 6414 - 6420.

18
[ 105-07-7 ]
[ 89891-69-0 ]

References: [1]Journal of the American Chemical Society,2017,vol. 139,p. 888 - 896.
[2]Journal of Organic Chemistry,2011,vol. 76,p. 6414 - 6420.

19
[ 1381846-22-5 ]
[ 89891-69-0 ]