[ CAS No. 5446-17-3 ] {[proInfo.proName]}

Name: 5446-17-3|(5-Chloro-2-methylphenyl)hydrazine hydrochloride|97%
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SKU: A305264
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Quality Control of [ 5446-17-3 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 5446-17-3 ]

SDS Specification

Alternatived Products of [ 5446-17-3 ]

Product Details of [ 5446-17-3 ]

CAS No. :	5446-17-3	MDL No. :	MFCD04038837
Formula :	C₇H₁₀Cl₂N₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	YAGKCRFGEGJKDS-UHFFFAOYSA-N
M.W :	193.07	Pubchem ID :	13200574
Synonyms :

Calculated chemistry of [ 5446-17-3 ]

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.14
Num. rotatable bonds :	1
Num. H-bond acceptors :	1.0
Num. H-bond donors :	2.0
Molar Refractivity :	50.59
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) :	-4.89 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.0
Log Po/w (XLOGP3) :	3.65
Log Po/w (WLOGP) :	2.55
Log Po/w (MLOGP) :	2.61
Log Po/w (SILICOS-IT) :	1.43
Consensus Log Po/w :	2.05

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-3.67
Solubility :	0.0409 mg/ml ; 0.000212 mol/l
Class :	Soluble
Log S (Ali) :	-4.14
Solubility :	0.0141 mg/ml ; 0.0000728 mol/l
Class :	Moderately soluble
Log S (SILICOS-IT) :	-3.08
Solubility :	0.161 mg/ml ; 0.000834 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	2.0
Synthetic accessibility :	1.45

Safety of [ 5446-17-3 ]

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 [ 5446-17-3 ]

* 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 [ 5446-17-3 ]
Downstream synthetic route of [ 5446-17-3 ]

[ 5446-17-3 ] Synthesis Path-Upstream 1~1

1
[ 95-79-4 ]
[ 5446-17-3 ]

Yield	Reaction Conditions	Operation in experiment
76%	Stage #1: With hydrogenchloride; sodium nitrite In water at 0℃; for 2 h; Inert atmosphere Stage #2: With tin(II) chloride dihdyrate In water at 0℃; for 0.75 h; Inert atmosphere	To an ice-cooled suspension of 5-chloro-2-methylaniline (1.4362 g, 10.143 mmol, 1.00 equiv) in water (10 mL) was added concentrated hydrochloric acid (10 mL). To this reaction mixture was added dropwise a solution of sodium nitrite (0.791 g, 11.5 mmol, 1.13 equiv) in water (5 mL) at 0° C. After 2 hours, the reaction mixture was slowly added to a stirring ice-cooled solution of tin chloride dihydrate (5.88 g, 25.8 mmol, 2.55 equiv) in concentrated hydrochloric acid (8 mL). Water was added as needed to maintain the stirring while solids formed. The reaction was kept at 0° C. for 45 minutes. The white solids were filtered and rinsed with diethyl ether (2.x.50 mL). The solids were dried under vacuum to provide 1.49 g (76percent) of (5-chloro-2-methylphenyl)hydrazine hydrochloride. ¹H NMR (400 MHz, DMSO-d₆) δ: 10.08 (s, 3H), 7.98 (s, 1H), 7.13 (d, 1H), 6.97 (s, 1H), 6.91 (d, 1H), 2.14 (s, 3H).

Reference： [1] Patent: US2012/22043, 2012, A1, . Location in patent: Page/Page column 84-85

[ 5446-17-3 ] Synthesis Path-Downstream 1~20

1
[ 6654-36-0 ]
[ 5446-17-3 ]
[ 109690-11-1 ]

Reference： [1]Journal of the American Chemical Society,1956,vol. 78,p. 5854,5856

2
diazotized 5-chloro-2-methyl-aniline [ No CAS ]
[ 5446-17-3 ]

Reference： [1]Journal of the American Chemical Society,1956,vol. 78,p. 5854,5856

3
[ 5446-17-3 ]
[ 105973-78-2 ]

Reference： [1]Journal of the American Chemical Society,1956,vol. 78,p. 5854,5856

4
[ 1118-61-2 ]
[ 5446-17-3 ]
[ 76606-55-8 ]

Yield	Reaction Conditions	Operation in experiment
		5-Amino-3-methyl-1-(4-chloro-2-methylphenyl) pyrazole <strong>[5446-17-3]5-chloro-2-methylphenylhydrazine HCl</strong> (80.32 g.) was reacted with 3-amino-2-butene nitrile (32.5 g.) as described in Example XLIII to give 60.5 g. product, mp 86-87. Analyzed for C11 H12 ClN3: Theoretical; C=59.59, H=5.45, N=18.95 Found; C=59.44, H=5.49, N=18.73.
		5-Amino-3-methyl-1-(4-chloro-2-methylphenyl) pyrazole <strong>[5446-17-3]5-chloro-2-methylphenylhydrazine HCl</strong> (80.32 g.) was reacted with 3-amino-2-butene nitrile (32.5 g.) as described in Example XLIII to give 60.5 g. product, mp 86-87. Analyzed for C11 H12 ClN3: Theoretical; C=59.59, H=5.45, N=18.95. Found; C=59.44, H=5.49, N=18.73.

Reference： [1]Patent: US4226773,1980,A
[2]Patent: US4234594,1980,A

5
[ 41979-39-9 ]
[ 5446-17-3 ]
9-Chloro-6-methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In ethanol; water; at 75℃; for 15h;	Example 12 9-Chloro-6-methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole hydrochloride; To a solution of <strong>[5446-17-3]1-<strong>[5446-17-3](5-chloro-2-methylphenyl)hydrazine hydrochloride</strong></strong> (1.0 g, 5.2 mmol) and 4-piperidone hydrochloride monohydrate (0.79 g, 5.2 mmol) in EtOH (8.9 mL) was added 12 N HCl (1.3 ml, 15.5. mmol) at 75 C. The reaction mixture was stirred at 75 C. for 15 h, filtered and rinsed with cold EtOH to obtain the title compound (0.65 mg, 2.5 mmol): MS (ES) 221.1 (M+H).

Reference： [1]Patent: US2007/27178,2007,A1 .Location in patent: Page/Page column 20

6
[ 1118-61-2 ]
[ 5446-17-3 ]
[ 1224944-69-7 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; In ethanol; at 80℃; for 16h;Inert atmosphere;	To a solution of <strong>[5446-17-3](5-chloro-2-methylphenyl)hydrazine hydrochloride</strong> (1.49 g, 7.72 mmol, 1.00 equiv) in ethanol (8 mL) was added hydrogen chloride (4.0 mL, 20 mmol, 2 equiv, 5 M aqueous solution) and 3-aminocrotonitrile (0.664 g, 8.09 mmol, 1.05 equiv). The reaction mixture was stirred at 80 C. for 16 hours and then brought to neutral pH with saturated aqueous sodium bicarbonate solution. The resultant solution was extracted twice with dichloromethane, and the combined extracts were dried over magnesium sulfate, filtered, and concentrated to yield 1.41 g (82%) of 1-(5-chloro-2-methylphenyl)-3-methyl-1H-pyrazol-5-amine, which was carried forward without further purification. LCMS (ESI) m+H=222.2; 1H NMR (400 MHz, DMSO-d6) delta: 7.39 (d, 1H), 7.37 (d, 1H), 7.25 (s, 1H), 5.22 (s, 1H), 5.00 (s, 2H), 2.04 (overlapping s and s, 6H).

Reference： [1]Patent: US2012/22043,2012,A1 .Location in patent: Page/Page column 85

7
[ 95-79-4 ]
[ 5446-17-3 ]

Yield	Reaction Conditions	Operation in experiment
76%		To an ice-cooled suspension of 5-chloro-2-methylaniline (1.4362 g, 10.143 mmol, 1.00 equiv) in water (10 mL) was added concentrated hydrochloric acid (10 mL). To this reaction mixture was added dropwise a solution of sodium nitrite (0.791 g, 11.5 mmol, 1.13 equiv) in water (5 mL) at 0 C. After 2 hours, the reaction mixture was slowly added to a stirring ice-cooled solution of tin chloride dihydrate (5.88 g, 25.8 mmol, 2.55 equiv) in concentrated hydrochloric acid (8 mL). Water was added as needed to maintain the stirring while solids formed. The reaction was kept at 0 C. for 45 minutes. The white solids were filtered and rinsed with diethyl ether (2×50 mL). The solids were dried under vacuum to provide 1.49 g (76%) of (5-chloro-2-methylphenyl)hydrazine hydrochloride. 1H NMR (400 MHz, DMSO-d6) delta: 10.08 (s, 3H), 7.98 (s, 1H), 7.13 (d, 1H), 6.97 (s, 1H), 6.91 (d, 1H), 2.14 (s, 3H).

Reference： [1]Patent: US2012/22043,2012,A1 .Location in patent: Page/Page column 84-85

8
[ 5446-17-3 ]
[ 1639789-04-0 ]