[ CAS No. 60481-35-8 ]

Name: 60481-35-8|(2-Bromo-5-fluorophenyl)hydrazine hydrochloride|97%
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Quality Control of [ 60481-35-8 ]

COA NMR CNMR HPLC LC-MS

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Product Details of [ 60481-35-8 ]

CAS No. :	60481-35-8	MDL No. :	MFCD22571157
Formula :	C₆H₇BrClFN₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	-
M.W :	241.49 g/mol	Pubchem ID :	21069774
Synonyms :

Calculated chemistry of of [ 60481-35-8 ]

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 :	2.0
Molar Refractivity :	48.27
TPSA :	38.05 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.82 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.0
Log Po/w (XLOGP3) :	2.75
Log Po/w (WLOGP) :	2.91
Log Po/w (MLOGP) :	2.88
Log Po/w (SILICOS-IT) :	1.46
Consensus Log Po/w :	2.0

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.41
Solubility :	0.0945 mg/ml ; 0.000391 mol/l
Class :	Soluble
Log S (Ali) :	-3.2
Solubility :	0.151 mg/ml ; 0.000625 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.23
Solubility :	0.143 mg/ml ; 0.000593 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.8

Safety of [ 60481-35-8 ]

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 [ 60481-35-8 ]

* 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 [ 60481-35-8 ]
Downstream synthetic route of [ 60481-35-8 ]

[ 60481-35-8 ] Synthesis Path-Upstream 1~1

1
[ 1003-99-2 ]
[ 60481-35-8 ]

Reference： [1] Patent: US2007/111984, 2007, A1, . Location in patent: Page/Page column 22

[ 60481-35-8 ] Synthesis Path-Downstream 1~18

2
[ 60481-35-8 ]
[ 41979-39-9 ]
6-bromo-9-fluoro-6-methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Step B.; A solution of <strong>[60481-35-8]1-(2-bromo-5-fluorophenyl)hydrazine hydrochloride</strong> (1.0 g, 4.1 mmol), 4-piperidone hydrochloride monohydrate (636 mg, 4.1 mmol), and 12N HCl (0.68 mL, 8.2 mmol) in EtOH (10 mL) was stirred at 75 C. for 15 h. The reaction mixture was cooled to 20 C. and filtered. The solid was dissolved in H2O, basified with 1N NaOH to pH>12 and extracted with CHCl3. The combined organic solution was dried over MgSO4, filtered and concentrated in vacuo to obtain the title compound as a yellow solid (54 mg, 0.20 mmol): MS (ES) 219.2 (M-H).

Reference： [1]Patent: US2007/27178,2007,A1 .Location in patent: Page/Page column 21

3
[ 823-94-9 ]
[ 60481-35-8 ]
[ 909274-73-3 ]

Yield	Reaction Conditions	Operation in experiment
62%	In ethanol;Heating / reflux;Product distribution / selectivity;	This triazole was also prepared in 62% yield from 1-<strong>[60481-35-8](2-bromo-5-fluoro-phenyl)-hydrazine hydrochloride</strong> and 2,4,6-trimethyl-s-triazine by refluxing them in EtOH.

Reference： [1]Patent: US2007/111984,2007,A1 .Location in patent: Page/Page column 25

4
[ 60481-35-8 ]
[ 119044-66-5 ]
[ 936486-92-9 ]
[ 506-59-2 ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine; at 20℃; for 1.0h;Product distribution / selectivity;	To a solution of <strong>[60481-35-8](2-bromo-5-fluoro-phenyl)-hydrazine hydrochloride</strong> (1.21 g, 5 mmol) in pyridine (3 mL) was added a solution of N-((dimethylamino)methylene)acetamide (600 mg, 5.26 mmol) in pyridine (2 mL) and the mixture stirred at room temperature under nitrogen for 1 h. The precipitate formed was collected, washed with CH2Cl2 and then with ether to obtain 1.15 g (3.16 mmol, 63% yield) of the title compound which was contaminated with 1 mole of dimethylamine hydrochloride as a white crystalline powder: HPLC: 2.22 min (AP 84% at 220 nm); LC/MS m/z 274/276 (M+H); 1H NMR (DMSO-d6, 500 MHz) delta ppm 2.00 (3H, s, 9-Me), 2.51 (6H, s, 2 N-CH3), 6.45 (1H, dt, J=8.5, 3 Hz, 5-CH), 6.89 (1H, dd, J=12, 3 Hz, 3-CH), 7.43 (1H, dd, J=8.5, 6 Hz, 6-CH), 8.68 (1H, d, J=9.5 Hz, 7-CH), 8.88 (2H, br.s, NH2+), 9.24 (1H, s, 7-NH), 10.54 (1H, d, J=9.5 Hz, 2-NH); No signals from the rotational isomer were observed; 13C NMR (CDCl3, 125.8 Hz) deltappm 22.6 (9-CH3), 33.9 (2 NCH3), 99.6 (d, J=28 Hz, 3-CH), 99.7 (1-C), 105.0 (d, J=24 Hz, 5-CH), 133.5 (d, J=10.6 Hz, 6-CH), 137.1 (7-CH), 144.9 (d, J=11.6 Hz, 2-C), 162.4 (d, J=244 Hz, 4-CF), 168.5 (8-CO). No signals from the rotational isomer were observed; Anal. calcd for C9H9BrFN3O.Me2NH.HCl.1/2H2O: C36.24, H4.99, N15.37, found C35.88, H4.87, N15.23. An analytical sample of the title compound without contamination of dimethylamine hydrochloride was obtained by column purification (SiO2, 10-15% EtOAc-CH2Cl2): TLC Rf 0.55 (20% EtOAc-CH2Cl2); HPLC: 2.17 min (AP 88% at 220 nm); LC/MS m/z 274/276 (M+H); 1H NMR (DMSO-d6, 500 MHz) delta ppm 1.99 (3H, s, 9-Me), 6.45 (1H, dt, J=8.5, 3 Hz, 5-CH), 6.88 (1H, dd, J=12, 3 Hz, 3-CH), 7.43 (1H, dd, J=9, 6 Hz, 6-CH), 8.69 (1H, d, J=9.5 Hz, 7-CH), 9.23 (1H, s, 7-NH), 10.52 (1H, d, J=9.5 Hz, 2-NH); About 16% of rotational isomer was also observed as a set of minor peaks: 1H NMR (DMSO-d6, 500 MHz) delta ppm 2.11 (3H, s, 9'-Me), 6.58 (1H, dt, J=8.5, 3 Hz, 5'-CH), 7.10 (1H, dd, J=1 1.6, 3 Hz, 3'-CH), 7.29 (1H, d, J=2.4 Hz, 7'-CH), 7.50 (1H, dd, J=8.7, 6 Hz, 6'-CH), 8.35 (1H, s, 2'-NH), 10.70 (1H, s, 7'-NH); 13C NMR (DMSO-d6, 125.8 Hz) deltappm 22.6 (9-CH3), 99.7 (d, J=29 Hz, 3-CH), 99.8 (d, J=3 Hz, 1-C), 105.0 (d, J=24 Hz, 5-CH), 133.6 (d, J=10.6 Hz, 6-CH), 137.1 (7-CH), 144.9 (d, J=11.6 Hz, 2-C), 162.5 (d, J=241 Hz, 4-CF), 168.5 (8-CO); 13C NMR (DMSO-d6, 125.8 Hz) delta ppm 22.9 (9'-CH3), 100.7 (d, J=3 Hz, 1'-C), 101.6 (d, J=29 Hz, 3'-CH), 106.8 (d, J=24 Hz, 5'-CH), 133.6 (d, J=9.6 Hz, 6'-CH), 162.4 (d, J=242 Hz, 4'-CF), 168.6 (8'-CO); HRMS (ESI) calcd for C9H10BrFN3O (M+H) 273.9991, found 274.0004 (delta+4.6 ppm); Anal. calcd for C9H9BrFN3O: C39.43, H3.31, N29.15, found C39.67, H2.99, N29.09.

Reference： [1]Patent: US2007/111984,2007,A1 .Location in patent: Page/Page column 23

5
[ 60481-35-8 ]
[ 119044-66-5 ]
[ 936486-92-9 ]

Yield	Reaction Conditions	Operation in experiment
	With acetic acid; In tetrahydrofuran; at 20℃; for 0.25h;Product distribution / selectivity;	Alternatively, to a mixture of <strong>[60481-35-8](2-bromo-5-fluoro-phenyl)-hydrazine hydrochloride</strong> (5.9 g, 28.8 mmol) and N-((dimethylamino)methylene)acetamide (3.30 g, 28.8 mmol) in THF (30 mL) was added 5 drops of HOAc, and the mixture stirred at room temperature under nitrogen for 15 min. The mixture was concentrated in vacuo, and the residue suspended in a mixture of ether (50 mL) and hexanes (50 mL) and the resulting precipitate collected and air-dried to provide 5.7 g of the title compound as an off-white powder. A second crop gave an additional 0.3 g.

Reference： [1]Patent: US2007/111984,2007,A1 .Location in patent: Page/Page column 23

6
[ 1003-99-2 ]
[ 60481-35-8 ]

Yield	Reaction Conditions	Operation in experiment
		To a suspension of (2-bromo-5-fluoro-phenyl)-hydrazine hydrochloride (41 g, 0.17 mol; prepared from 2-bromo-5-fluoroaniline by the method described in U.S. Pat. No. 3,959,309 (1976) p-23, and p-48) in water (300 mL) and CH2Cl2 (200 mL) was added 1N-NaOH (200 mL) until the solution was basic. The CH2Cl2 layer was separated and the aqueous portion was further extracted with CH2Cl2 (150 mL). The combined organic extracts were dried (MgSO4), filtered, and concentrated to obtain 33 g (0.16 mol) of the title compound as an off-white powder: HPLC: 0.89 min (AP 97% at 220 nm); 1H NMR (CDCl3, 500 MHz) delta ppm 3.62 (2H, s, NH2), 5.75 (1H, s, NH), 6.37 (1H, m, 5-CH), 6.87 (1H, dd, J=11, 3 Hz, 3-CH), 7.31 (1H, dd, J=8.6, 5.8 Hz, 6-CH); 13C NMR (CDCl3, 125.8 Hz) 8ppm 100.0 (d, J=29 Hz, 3-CH), 101.4 (d, J=2.9 Hz, 1-C), 106.1 (d, J=23 Hz, 5-CH), 133.1 (d, J=9.6 Hz, 6-CH), 149.1 (d, J=10.6 Hz, 2-C), 163.5 (d, J=244 Hz, 4-CF); LC/MS m/z 205/207 (M+H).

Reference： [1]Patent: US2007/111984,2007,A1 .Location in patent: Page/Page column 22

7
[ 60481-35-8 ]
[ 776239-07-7 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; In dichloromethane; water;pH > 7;	To a suspension of <strong>[60481-35-8](2-bromo-5-fluoro-phenyl)-hydrazine hydrochloride</strong> (41 g, 0.17 mol; prepared from 2-bromo-5-fluoroaniline by the method described in U.S. Pat. No. 3,959,309 (1976) p-23, and p-48) in water (300 mL) and CH2Cl2 (200 mL) was added 1N-NaOH (200 mL) until the solution was basic. The CH2Cl2 layer was separated and the aqueous portion was further extracted with CH2Cl2 (150 mL). The combined organic extracts were dried (MgSO4), filtered, and concentrated to obtain 33 g (0.16 mol) of the title compound as an off-white powder: HPLC: 0.89 min (AP 97% at 220 nm); 1H NMR (CDCl3, 500 MHz) delta ppm 3.62 (2H, s, NH2), 5.75 (1H, s, NH), 6.37 (1H, m, 5-CH), 6.87 (1H, dd, J=11, 3 Hz, 3-CH), 7.31 (1H, dd, J=8.6, 5.8 Hz, 6-CH); 13C NMR (CDCl3, 125.8 Hz) 8ppm 100.0 (d, J=29 Hz, 3-CH), 101.4 (d, J=2.9 Hz, 1-C), 106.1 (d, J=23 Hz, 5-CH), 133.1 (d, J=9.6 Hz, 6-CH), 149.1 (d, J=10.6 Hz, 2-C), 163.5 (d, J=244 Hz, 4-CF); LC/MS m/z 205/207 (M+H).

Reference： [1]Patent: US2007/111984,2007,A1 .Location in patent: Page/Page column 22

8
[ 60481-35-8 ]
[ 625-77-4 ]
[ 909274-73-3 ]