[ CAS No. 52068-30-1 ] {[proInfo.proName]}

Name: 52068-30-1|(4-(Benzyloxy)phenyl)hydrazine hydrochloride|95%
Brand: Ambeed
SKU: A268201
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2D 3D

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Quality Control of [ 52068-30-1 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 52068-30-1 ]

SDS Specification

Alternatived Products of [ 52068-30-1 ]

Product Details of [ 52068-30-1 ]

CAS No. :	52068-30-1	MDL No. :	MFCD00137741
Formula :	C₁₃H₁₅ClN₂O	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	OVNUPJXMCMTQCN-UHFFFAOYSA-N
M.W :	250.72	Pubchem ID :	3016725
Synonyms :

Calculated chemistry of [ 52068-30-1 ]

Physicochemical Properties

Num. heavy atoms :	17
Num. arom. heavy atoms :	12
Fraction Csp3 :	0.08
Num. rotatable bonds :	4
Num. H-bond acceptors :	2.0
Num. H-bond donors :	2.0
Molar Refractivity :	71.59
TPSA :	47.28 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	Yes
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.11 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.0
Log Po/w (XLOGP3) :	3.83
Log Po/w (WLOGP) :	3.01
Log Po/w (MLOGP) :	2.88
Log Po/w (SILICOS-IT) :	1.87
Consensus Log Po/w :	2.32

Druglikeness

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

Water Solubility

Log S (ESOL) :	-4.07
Solubility :	0.0216 mg/ml ; 0.000086 mol/l
Class :	Moderately soluble
Log S (Ali) :	-4.52
Solubility :	0.0076 mg/ml ; 0.0000303 mol/l
Class :	Moderately soluble
Log S (SILICOS-IT) :	-4.76
Solubility :	0.00437 mg/ml ; 0.0000174 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.81

Safety of [ 52068-30-1 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H332-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 52068-30-1 ]

* 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 [ 52068-30-1 ]
Downstream synthetic route of [ 52068-30-1 ]

[ 52068-30-1 ] Synthesis Path-Upstream 1~7

1
[ 51388-20-6 ]
[ 52068-30-1 ]

Yield	Reaction Conditions	Operation in experiment
96%	Stage #1: With hydrogenchloride; sodium nitrite In water at 0℃; for 0.5 h; Stage #2: With tin(ll) chloride In water at 0℃; for 1 h;	(4-(Benzyloxy)phenyl)hydrazine hydrochloride (2).; Note: The reaction mixture and all added solutions were maintained at 0 °C during this procedure. 4-Benzyloxyaniline hydrochloride (3.00 g, 12.5 mmol) was added to cone. aq. HC1 (25 mL) and stirred for 10 min at 0 °C, followed by dropwise addition of a solution of NaN0₂ (852 mg, 12.3 mmol) in water (6 mL) over the course of 15 min. The mixture was stirred for an additional 15 min-period and then a solution of SnCl₂ (6.40 g, 33.1 mmol) in cone. aq. HC1 (7.5 mL) was added dropwise. The reaction mixture was stirred for 1 h and filtered to yield an off-white precipitate, which was washed with water and triturated with Et₂0, to yield 2 (3.01 g, 96percent):IR (ATR, neat) 3232, 2906 (br), 2693, 1568, 1508, 1242, 1177 cm^"1; 1H NMR (DMSO-d₆, 600 MHz) δ 10.11 (bs, 3 H), 7.44-7.40 (m, 2 H), 7.40-7.35 (m, 2 H), 7.33-7.29 (m, 1 H), 7.01-6.93 (m, 4 H), 5.05 (s, 2 H); ¹³C NMR (DMSO-d₆, 150 MHz) δ 153.7, 139.1, 137.3, 128.5, 128.4, 128.3, 127.9, 127.7, 127.5, 117.1, 116.9, 115.5, 115.3, 69.5; HRMS (EI) m/z calcd for Ci₃Hi₄N₂0 214.1106, found 214.1110.
92%	Stage #1: With hydrogenchloride In water at 0℃; for 0.166667 h; Stage #2: With sodium nitrite In water at 0℃; for 0.5 h; Stage #3: With tin(ll) chloride In water at 0℃; for 1 h;	Note: The reaction mixture and all added solutions were maintainedat 0 C during this procedure. 4-Benzyloxyanilinehydrochloride (3) (3.0 g, 12.5 mmol) was added to concd aq HCl(25 mL) and stirred for 10 min at 0 C, followed by dropwise additionof NaNO2 (852 mg, 12.3 mmol) in water (6 mL) over the courseof 15 min. The mixture was stirred for additional 15 min and then asolution of SnCl2 (6.4 g, 33.1 mmol) in concd aq HCl (7.5 mL) wasadded dropwise. The reaction mixture was stirred for 1 h and filteredto yield an off-white precipitate, which was washed withwater and triturated with Et2O, to afford an off-white solid (2.9 g,92percent); Mp 179–181 C. IR: mmax (KBr) cm1: 3232, 2907 (br), 1638,1618, 1511, 1246, 1178. 1H NMR (DMSO-d6, 400 MHz) d 10.14(br s, 3H, NH–NH2), 7.35–7.48 (m, 4H, Ar-H), 7.27–7.35 (m, 1H,Ar-H), 6.92–7.05 (m, 4H, Ar-H), 5.06 (s, 2H, CH2). 13C NMR(DMSO-d6, 100 MHz) d 153.7 (ArC–O), 139.1 (ArC–N), 137.3(ArC), 128.5 (ArC), 128.4 (ArC), 128.3 (ArC), 127.9 (ArC), 127.7(ArC), 117.1 (ArC), 116.9 (ArC), 115.5 (ArC), 115.3 (ArC), 69.5(CH2). HRMS (EI): Found 215.1180 (M+H)+, C13H15N2O requires215.1184.
82%	With hydrogenchloride; stannous chloride; sodium nitrite In diethyl ether; water	(a) 4-Benzyloxyphenylhydrazine hydrochloride To 4-benzyloxyaniline hydrochloride (250 g, 1.56 mol) are added water (355 ml) and con. hydrochloric acid (175 ml), and the mixture is stirred while suspending. A solution of NaNO₂ (73.2 g, 1.06 mol) in water (180 ml) is dropwise added at a temperature of 0 - 5°C, followed by stirring at the same temperature for 1 hour (A solution). To con. hydrochloric acid (2.65) is added SnCl₂ (604 g), and the A solution is added dropwise at a temperature of 0 - 5°C while stirring. After stirring at the same temperature for 30 minutes, Et₂O (2) is further added thereto, followed by further stirring for 30 minutes. The precipitated crystals are filtered off, the crystals are added to methanol (3), and the mixture is stirred for 30 minutes. The crystals are filtered off, and dried to give 220 g of (a) (Yield 82percent). m.p. 187°C (MeOH-H₂O) TLC (Merck No. 5714 Sol. CHCl₃:MeOH=10:1) Rf=0.49 IR (Nujol) cm-¹: 3230, 1585, 1510 ¹H-NMR (DMSO-D₆) δ ppm: 5.03 (2H, s, -CH₂-O), 7.35 (5H, s, C-phenyl), 11.0 (3H, br-s, -NH-NH₂ * HCl)

Reference： [1] Patent: WO2012/78859, 2012, A2, . Location in patent: Page/Page column 47
[2] Bioorganic and Medicinal Chemistry, 2016, vol. 24, # 18, p. 4075 - 4099
[3] Patent: EP427860, 1991, A1,
[4] Bioorganic and Medicinal Chemistry, 2010, vol. 18, # 10, p. 3387 - 3402
[5] Patent: US5102891, 1992, A,
[6] Patent: US3959309, 1976, A,
[7] Patent: US4062864, 1977, A,
[8] Patent: WO2014/186325, 2014, A1, . Location in patent: Page/Page column 25

2
[ 6373-46-2 ]
[ 52068-30-1 ]

Yield	Reaction Conditions	Operation in experiment
95%	With sodium nitrite In hydrogenchloride; water	A. 4-Benzyloxyphenylhydrazine hydrochloride A solution of sodium nitrite (3.8 g, 0.055 mol in 20 mL of H₂ O), is added dropwise to an ice cold stirring suspension of 4-benzyloxyaniline (13.0 g, 0.055 mol in 150 mL of concentrated HCl). The reaction mixture is stirred for 90 minutes at -8° to 10° C. A solution of SnCl_2.2H₂ O (32.0 g, 0142 mol in 50 mL concentrated HCl) is added and stirred for 1 hour at 0° C. The reaction mixture is removed from the ice bath and is stirred at room temperature for 20 hours. The mixture is then filtered and washed with water to give 13.0 g (95percent yield) of product, m.p. 182°-185° C.

Reference： [1] Patent: US5229516, 1993, A,

3
[ 6373-46-2 ]
[ 52068-30-1 ]

Yield	Reaction Conditions	Operation in experiment
95%	With sodium nitrite In hydrogenchloride; water	A. 4-Benzyloxyphenylhydrazine hydrochloride A solution of sodium nitrite (3.8 g, 0.055 mol in 20 mL of H₂ O), is added dropwise to an ice cold stirring suspension of 4-benzyloxyaniline (13.0 g, 0.055 mol in 150 mL of concentrated HCl). The reaction mixture is stirred for 90 minutes at -8° to 10° C. A solution of SnCl₂ *2H₂ O (32.0 g, 0142 mol in 50 mL concentrated HCl) is added and stirred for i hour at 0° C. The reaction mixture is removed from the ice bath and is stirred at room temperature for 20 hours. The mixture is then filtered and washed with water to give 13.0 g (95percent yield) of product, m.p. 182°-185° C.

Reference： [1] Patent: US5420289, 1995, A,

4
[ 6373-46-2 ]
[ 52068-30-1 ]

Reference： [1] Patent: EP596983, 1995, B1,

5
[ 51388-20-6 ]
[ 52068-30-1 ]

Reference： [1] Patent: US4725615, 1988, A,

6
[ 51145-58-5 ]
[ 52068-30-1 ]

Reference： [1] Journal of Organic Chemistry, 2013, vol. 78, # 15, p. 7445 - 7454

7
[ 4495-66-3 ]
[ 52068-30-1 ]
[ 198479-63-9 ]

Yield	Reaction Conditions	Operation in experiment
94%	With acetic acid In ethanol at 75 - 80℃;	Example-2 4-Benzyloxy phenyl hydrazine hydrochloride (10 g, 40 mmol), 4-benzyloxy propiophenone (9.6 g, 40 mmol) and acetic acid (0.1 ml, 1.7 mmol) were suspended in 140 ml of ethanol and the mixture was refluxed for 12 hrs at a temperature of 75-80° C. During said period the product precipitates. After cooling the mixture at 10-15° C. the crystallized product was isolated by filtration and washed with chilled ethanol (30 ml) and water (50 ml). 5-Benzyloxy-2-(4-benzyloxy)-3-methyl-1H-indole melting at 152-153° C. was obtained in a yield of 15.7 g (94percent). ¹H-NMR (DMSO) δ 10.65 (s, 1H); 7.55 (d, 2H); 7.50 (d, 4H); 7.30-7.45 (m, 6H); 7.21 (d, 1H); 7.10 (d, 1H); 7.10 (d, 1H); 6.91 (dd, 1H); 5.16 (s, 2H); 5.11 (s, 2H); 2.33 (s, 3H)
94%	at 75 - 80℃; for 12 h;	Example-2 4-Benzyloxy phenyl hydrazine hydrochloride (10 g, 40 mmol), 4-benzyloxy propiophenone (9.6 g, 40 mmol) and acetic acid (0.1 ml, 1.7 mmol) were suspended in 140 ml of ethanol and the mixture was refluxed for 12 hrs at the temperature of 75 to 80°C. During said period the product precipitates. After cooling the mixture at 10 to 15°C the crystallized product was isolated by filtration and washed with chilled ethanol (30 ml) and water (50 ml). 5-Benzyloxy-2-(4-benzyloxy)-3-methyl-1H-indole melting at 152 to 153°C was obtained in a yield of 15.7 g (94percent). ¹H-NMR (DMSO) δ 10.65 (s, 1H); 7.55 (d, 2H); 7.50(d, 4H); 7.30-7.45(m, 6H); 7.21(d, 1H); 7.10(d, 1H); 7.10(d, 1H); 6.91(dd, 1H); 5.16(s, 2H); 5.11(s, 2H); 2.33(s, 3H)
84%	With hydrogenchloride In ethanol for 2 h; Reflux	1-(4-(Benzyloxy)phenyl)propan-1-one (2) (1.9 g, 8.0 mmol) and1-(4-(benzyloxy)phenyl)hydrazine hydrochloride (4) (2.0 g,8.0 mmol) were dissolved in EtOH (50 mL) and 5 drops of conc.HCl was added and the mixture was refluxed for 2 h. The reaction mixture was then allowed to cool and was stirred for 1 h. The mixturewas filtered to afford an pale pink solid. The solid was washedwith cold EtOH (10 mL) followed by n-hexane (20 mL). (2.8 g, 84percent).Mp: 149–152 C.50 IR: mmax (KBr) cm1: 3470 (N–H), 2880, 2820,1620 (CC). 1H NMR (CDCl3, 400 MHz) d 7.86 (br s, 1H, NH),7.48–7.58 (m, 6H, Ar-H), 7.33–7.47 (m, 6H, Ar-H), 7.25–7.31 (m,1H, Ar-H), 7.14–7.18 (m, 1H, Ar-H), 7.07–7.13 (m, 2H, Ar-H), 6.97(d, J = 7.53 Hz, 1H, Ar-H), 5.18 (s, 2H, CH2), 5.15 (s, 2H CH2), 2.43(s, 3H, CH3) 13C NMR (CDCl3, 100 MHz) d 157.7 (BnO–C), 157.3(BnO–C), 143.6 (Ar-C–CH2), 137.3 (Cq), 136.3 (Cq), 136.0 (Cq),129.9 (ArC), 128.5 (ArC), 128.2 (ArC), 128.2 (ArC), 127.7 (ArC),127.6 (Ar-C), 127.1 (ArC), 120.4 (ArC), 114.7 (ArC), 114.6 (ArC),114.3 (ArC), 112.2 (Cq), 110.8 (CC), 108.8 (ArC), 102.0 (ArC),70.0 (CH2), 69.6 (CH2), 9.3 (CH3). HRMS (EI): Found 442.1797 (M+Na)+, C29H25NNaO2 requires 442.1783.

Reference： [1] Patent: US7968732, 2011, B1, . Location in patent: Page/Page column 3-4
[2] Patent: EP2426105, 2012, A1, . Location in patent: Page/Page column 3-4
[3] Bioorganic and Medicinal Chemistry, 2016, vol. 24, # 18, p. 4075 - 4099

[ 52068-30-1 ] Synthesis Path-Downstream 1~88

1
[ 52068-30-1 ]
[ 122-01-0 ]
[ 36586-42-2 ]

Reference： [1]Patent: DE2146192,1972,
Chem.Abstr.,1972,vol. 77

2
[ 5264-35-7 ]
[ 52068-30-1 ]
[ 99280-74-7 ]

Reference： [1]Angewandte Chemie,1985,vol. 97,p. 1063 - 1064

3
[ 52068-30-1 ]
[ 154005-67-1 ]
[ 53017-44-0 ]

Reference： [1]Chemical and pharmaceutical bulletin,1984,vol. 32,p. 2126 - 2139

4
[ 52068-30-1 ]
[ 93271-96-6 ]
[ 89434-13-9 ]

Reference： [1]Chemical and pharmaceutical bulletin,1984,vol. 32,p. 2126 - 2139

5
[ 52068-30-1 ]
[ 93271-96-6 ]
[ 89434-13-9 ]

Reference： [1]Chemical and pharmaceutical bulletin,1984,vol. 32,p. 2126 - 2139

6
[ 52068-30-1 ]
[ 826-73-3 ]
[ 898252-79-4 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 3233 - 3237

7
[ 937177-45-2 ]
[ 52068-30-1 ]
[ 937177-63-4 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 2322 - 2328

8
[ 52068-30-1 ]
[ 937177-71-4 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 2322 - 2328

9
[ 52068-30-1 ]
[ 937177-67-8 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 2322 - 2328

10
[ 52068-30-1 ]
N-[3-(4-hydroxy-phenyl)-1-methyl-propyl]-2-[2-phenyl-5-(2-piperidin-1-yl-ethoxy)-1H-indol-3-yl]-acetamide [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 2322 - 2328

11
[ 52068-30-1 ]
N-[3-(4-hydroxy-phenyl)-1-methyl-propyl]-2-[2-phenyl-5-(3-piperidin-1-yl-propoxy)-1H-indol-3-yl]-acetamide [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 2322 - 2328

12
[ 52068-30-1 ]
[ 937177-75-8 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 2322 - 2328

13
[ 52068-30-1 ]
[ 937177-76-9 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 2322 - 2328

14
[ 52068-30-1 ]
N-[3-(4-hydroxy-phenyl)-1-methyl-propyl]-2-[2-phenyl-5-(4-piperidin-1-yl-butoxy)-1H-indol-3-yl]-acetamide [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 2322 - 2328

15
[ 52068-30-1 ]
[ 937177-77-0 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 2322 - 2328

16
[ 52068-30-1 ]
N-[3-(4-hydroxy-phenyl)-1-methyl-propyl]-2-[2-phenyl-5-(5-piperidin-1-yl-pentyloxy)-1H-indol-3-yl]-acetamide [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 2322 - 2328

17
[ 52068-30-1 ]
[ 937177-78-1 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 2322 - 2328

18
[ 52068-30-1 ]
7-methoxy-5,6-dihydrobenzo[c]acridin-9-ol [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 3233 - 3237

19
[ 52068-30-1 ]
9-hydroxy-12-methyl-6,12-dihydro-5H-benzo[c]acridin-7-one [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 3233 - 3237

20
[ 52068-30-1 ]
[ 898252-82-9 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 3233 - 3237

21
[ 52068-30-1 ]
[ 898252-80-7 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 3233 - 3237

22
[ 52068-30-1 ]
[ 898252-81-8 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 3233 - 3237

23
[ 52068-30-1 ]
[ 2504-32-7 ]