24468-88-0|N-Benzyl-2-bromo-N-(2-bromoethyl)ethanamine| Ambeed

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Quality Control of [ 24468-88-0 ] Purity: 97% SDS Specification

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Product Details of [ 24468-88-0 ]

CAS No. :	24468-88-0
Formula :	C₁₁H₁₅Br₂N
M.W :	321.05
SMILES Code :	BrCCN(CCBr)CC1=CC=CC=C1
MDL No. :	MFCD01657317
InChI Key :	NOCFCCNGOFVBDJ-UHFFFAOYSA-N
Pubchem ID :	34259

Safety of [ 24468-88-0 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H317-H319
Precautionary Statements:	P305+P351+P338-P280

Computational Chemistry of [ 24468-88-0 ] Show Less

Physicochemical Properties

Num. heavy atoms	14
Num. arom. heavy atoms	6
Fraction Csp3	0.45
Num. rotatable bonds	6
Num. H-bond acceptors	1.0
Num. H-bond donors	0.0
Molar Refractivity	69.27
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	3.24 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	3.14
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	3.28
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	3.13
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.	3.6
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	3.54
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	3.34

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-3.82
Solubility	0.0488 mg/ml ; 0.000152 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.	-3.02
Solubility	0.305 mg/ml ; 0.000949 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	-5.44
Solubility	0.00117 mg/ml ; 0.00000363 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	Yes
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.	-5.93 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<0.0
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)	1.52

Application In Synthesis of [ 24468-88-0 ]

* 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 [ 24468-88-0 ]

[ 24468-88-0 ] Synthesis Path-Downstream 1~21

1
4-benzyl-morpholine; hydrobromide [ No CAS ]
[ 24468-88-0 ]

References: [1]Arhiv za Kemiju,1946,vol. 18,p. 37,38.
Chem.Abstr.,1948,p. 1942.

2
[ 91335-65-8 ]
[ 24468-88-0 ]

References: [1]Canadian Journal of Chemistry,1964,vol. 42,p. 1699 - 1706.

3
[ 98-88-4 ]
(+-)-2.3-dibromo-propylamine hydrobromide [ No CAS ]
[ 24468-88-0 ]

References: [1]Canadian Journal of Chemistry,1964,vol. 42,p. 1699 - 1706.

4
[ 101-32-6 ]
[ 24468-88-0 ]

Yield	Reaction Conditions	Operation in experiment
54.6%	With phosphorus tribromide; In toluene; at 0℃; for 6h;Inert atmosphere; Reflux;	A mixture of compound O-1 (12.10 g, 115.1 mmol), benzyl bromide (13.70 mL, 115.3 mmol) and potassium carbonate (31.81 g, 230.2 mmol) in acetone (120 mL) was refluxed for 18 hours, cooled to rt and filtered. The filtrate was concentrated in vacuo. The residue was purified by silica gel column chromatography (DCM/MeOH (v/v) = 20/1) to give compound O-2 as pale yellow liquid (16.39 g, 72.9%). The compound was characterized by the following spectroscopic data: 1H NMR (400 MHz, CDCl3): delta 7.36-7.23 (m, 5H), 3.70 (s, 2H), 3.62 (t, J = 5.3 Hz, 4H), 2.72 (t, J = 5.3 Hz, 4H), 2.48 (brs, 2H). [0555] To a solution of compound O-2 (14.60 g, 74.77 mmol) in toluene (140 mL) was added phosphorus tribromide (21.1 mL, 224.5 mmol) dropwise at 0 C under N2. At the end of the addition, the mixture was refluxed for 6 hours, cooled to rt, quenched with ice water (400 mL) and filtered. The filtrate was washed with NaOH solution and extracted with DCM (100 mL x 3). The combined organic phases were dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by silica gel column chromatography (hexane/EtOAc (v/v) = 10/1) to give the title compound 32-1 as colorless oil (13.30 g, 54.6%). The compound was characterized by the following spectroscopic data: 1H NMR (400 MHz, CDCl3): delta 7.36-7.25 (m, 5H), 3.73 (s, 2H), 3.34 (t, J = 7.3 Hz, 4H), 2.98 (t, J = 7.3 Hz, 4H).
54.6%	With phosphorus tribromide; In toluene; at 0℃; for 6h;Inert atmosphere; Reflux;	To a solution of compound O-2 (14.60 g, 74.77 mmol) in toluene (140 mL) was added phosphorus tribromide(21.1 mL, 224.5 mmol) dropwise at 0 C under N2. At the end of the addition, the mixture was refluxed for 6 hours, cooledto rt, quenched with ice water (400 mL) and filtered. The filtrate was washed with NaOH solution and extracted withDCM (100 mL x 3). The combined organic phases were dried over anhydrous Na2SO4 and concentrated in vacuo. Theresidue was purified by silica gel column chromatography (hexane/EtOAc (v/v) = 10/1) to give the title compound 32-1as colorless oil (13.30 g, 54.6%). The compound was characterized by the following spectroscopic data:1H NMR (400 MHz, CDCl3): delta 7.36-7.25 (m, 5H), 3.73 (s, 2H), 3.34 (t, J = 7.3 Hz, 4H), 2.98 (t, J = 7.3 Hz, 4H).
18%	With phosphorus tribromide; In dichloromethane; at 0 - 20℃; for 8h;	Into a 500-mL round-bottom flask was placed 2,2'-(benzylazanediyl)diethanol (11.3 g, 57.9 mmol, 1 equiv) and CH2C12 (100 mL). This was followed by the dropwise addition of phosphorus tribromide (34.6 g, 128 mmol, 2.2 equiv) at 0 C. The resulting solution was stirred for 8 h at room temperature. The reaction was then quenched by the addition of 80 mL of ice-water. The pH value of the solution was adjusted to 7 with sat. aq. Na2C03 solution. The resulting solution was extracted with 3x80 mL of CH2C12. The combined organic layers were dried over anhydrous Na2S04, filtered, and concentrated under vacuum. The residue was purified by normal phase chromatography on silica gel using CH2Cl2/petroleum ether (1 :3). The collected fractions were concentrated under vacuum to afford 3.3 g (18% yield) of the title compound as yellow oil. 1H MR (400 MHz, CDC13) delta (ppm): 7.34-7.27 (m, 5H), 3.73 (s, 2H), 3.43 (t, J= 7.2 Hz, 4H), 2.98 (t, J= 7.2 Hz, 1H).

41.58 g	With phosphorus tribromide; In toluene; at 0 - 105℃; for 16h;	To a 0 C solution of 2,2?-(benzylazanediyl)bis(ethan-l-ol) (30.66 g, 0.16 mol) intoluene (300 mL) was added tribromophosphane (69.13 g, 0.26 mol) dropwise. The resultingmixture was stirred at 105 C for 16 h. After cooling to RT, the volatiles were removed under reduce pressure. The residue was diluted with water (300 mL), and the pH value was adjusted to 9with NaOH. The resulting mixture was extracted with EA (3 x 150 mL), the organic layers combined, dried over anhydrous Na2504 and filtered. The filtrate was concentrated under reducedpressure to give N-benzyl-2-bromo-N-(2-bromoethyl) ethan-1-amine (41.58 g) which was used in next step without any further purification. MS: m/z 320 (M+H).
41.58 g	With phosphorus tribromide; In toluene; at 0 - 105℃; for 15h;	N-Benzyldiethanolamine (30.66 g, 0.16 mol) in toluene (300 mL) at 0 CPhosphorus tribromide (69.13 g, 0.26 mol) was added dropwise to the solution. The system was heated to 105 C and stirred for 16 h.After cooling to RT, the volatiles were removed under reduced pressure. The residue was diluted with water (300 mL) and the pH was adjusted to 9 with NaOH.The system was extracted with EA (3×150 mL).The filtrate was concentrated under reduced pressure to give N-benzyl-2-bromo-N-(2-bromoethyl)ethane-l-amine (41.58 g).Used directly in the next step without any further purification.

References: [1]Inorganic Chemistry,2011,vol. 50,p. 10213 - 10224.
[2]Patent: EP2730572,2015,B1 .Location in patent: Paragraph 0554-0555.
[3]Patent: EP2730572,2015,B1 .Location in patent: Paragraph 0553; 0555.
[4]Patent: WO2018/75959,2018,A1 .Location in patent: Paragraph 0772-0773.
[5]Patent: WO2018/172984,2018,A1 .Location in patent: Page/Page column 53.
[6]Patent: CN110143949,2019,A .Location in patent: Paragraph 0211; 0213.
[7]Patent: US2020/108071,2020,A1 .Location in patent: Paragraph 0853.
[8]Patent: WO2020/63760,2020,A1 .Location in patent: Page/Page column 86.

5
[ 24468-88-0 ]
[ 829-85-6 ]
[ 99573-07-6 ]

References: [1]Inorganic Chemistry,2011,vol. 50,p. 10213 - 10224.

6
[ 100-39-0 ]
[ 24468-88-0 ]

References: [1]Inorganic Chemistry,2011,vol. 50,p. 10213 - 10224.
[2]Patent: WO2018/75959,2018,A1 .
[3]Patent: WO2018/172984,2018,A1 .
[4]Patent: EP2730572,2015,B1 .
[5]Patent: CN110143949,2019,A .
[6]Patent: US2020/108071,2020,A1 .
[7]Patent: WO2020/63760,2020,A1 .

7
[ 24468-88-0 ]
[ 1419389-18-6 ]

References: [1]Patent: EP2730572,2015,B1 .

8
[ 24468-88-0 ]
[ 1419389-20-0 ]

References: [1]Patent: EP2730572,2015,B1 .

9
[ 52428-09-8 ]
[ 24468-88-0 ]
[ 1419389-16-4 ]

Yield	Reaction Conditions	Operation in experiment
14.9%	With sodium hydride; In N,N-dimethyl-formamide; mineral oil; at 50℃; for 18h;Inert atmosphere;	To a solution of compound 1-2 (2.56 g, 14.34 mmol) and compound 32-1 (6.905 g, 21.51 mmol) in DMF (15 mL) under N2 was added NaH (1.434g, 35.85 mmol, 60% dispersed in Mineral oil). The mixture was stirred at 50 C for 18 hours, cooled to rt, and quenched with water (20 mL). The mixture was extracted with EtOAc (150 mL x 3). The combined organic phases were washed with water, dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by silica gel column chromatography (hexane/EtOAc (v/v) = 8/1) to give the title compound 32-2 (0.752 g, 14.9%). The compound was characterized by the following spectroscopic data: MS-ESI: m/z 352.1 [M+H]+; and1H NMR (400 MHz, CDCl3): delta 7.63-7.56 (m, 1H), 7.41-7.22 (m, 6H), 3.82 (d, 6H), 3.56 (s, 2H), 3.03 (s, 2H), 2.98-2.89 (m, 2H), 2.24-2.00 (m, 4H), 1.37 (d, J = 11.8 Hz, 2H).
14.9%	With sodium hydride; In N,N-dimethyl-formamide; mineral oil; at 50℃; for 18h;Inert atmosphere;	To a solution of compound 1-2 (2.56 g, 14.34 mmol) and compound 32-1 (6.905 g, 21.51 mmol) in DMF (15mL) under N2 was added NaH (1.434g, 35.85 mmol, 60% dispersed in Mineral oil). The mixture was stirred at 50 C for18 hours, cooled to rt, and quenched with water (20 mL). The mixture was extracted with EtOAc (150 mL x 3). Thecombined organic phases were washed with water, dried over anhydrous Na2SO4 and concentrated in vacuo. Theresidue was purified by silica gel column chromatography (hexane/EtOAc (v/v) = 8/1) to give the title compound 32-2(0.752 g, 14.9%). The compound was characterized by the following spectroscopic data:MS-ESI: m/z 352.1 [M+H]+; and1H NMR (400 MHz, CDCl3): delta 7.63-7.56 (m, 1H), 7.41-7.22 (m, 6H), 3.82 (d, 6H), 3.56 (s, 2H), 3.03 (s, 2H), 2.98-2.89(m, 2H), 2.24-2.00 (m, 4H), 1.37 (d, J = 11.8 Hz, 2H).

References: [1]Patent: EP2730572,2015,B1 .Location in patent: Paragraph 0556.
[2]Patent: EP2730572,2015,B1 .Location in patent: Paragraph 0553; 0556.

10
[ 24468-88-0 ]
[ 25364-47-0 ]
C₄₁H₅₅N₅⁽²⁺⁾*2Br^(1-) [ No CAS ]

References: [1]Journal of the American Chemical Society,2015,vol. 137,p. 7620 - 7623.

11
[ 24468-88-0 ]
[ 223762-69-4 ]
C₃₃H₃₉N₅⁽²⁺⁾*2Br^(1-) [ No CAS ]

References: [1]Journal of the American Chemical Society,2015,vol. 137,p. 7620 - 7623.

12
[ 24468-88-0 ]
[ 25364-44-7 ]
C₃₅H₄₃N₅⁽²⁺⁾*2Br^(1-) [ No CAS ]

References: [1]Journal of the American Chemical Society,2015,vol. 137,p. 7620 - 7623.

13
1,2,3-triselena[3] ferrocenophane [ No CAS ]
[ 24468-88-0 ]
Se₄N₂[7,7]ferrocenophane [ No CAS ]
Se₂N[10]ferrocenophane [ No CAS ]

References: [1]Dalton Transactions,2016,vol. 45,p. 3417 - 3428.

14
[ 15115-60-3 ]
[ 24468-88-0 ]
1‘-benzyl-4-bromospiro[indene-2,4’-piperidin]-1(3H)-one [ No CAS ]