[ CAS No. 53661-18-0 ] {[proInfo.proName]}

Name: 53661-18-0|4-Ethylphenylhydrazine Hydrochloride|97%
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Quality Control of [ 53661-18-0 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 53661-18-0 ]

Product Details of [ 53661-18-0 ]

CAS No. :	53661-18-0	MDL No. :	MFCD01861267
Formula :	C₈H₁₃ClN₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	YGFUKCJADFMHGW-UHFFFAOYSA-N
M.W :	172.66	Pubchem ID :	2760970
Synonyms :

Calculated chemistry of [ 53661-18-0 ]

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.25
Num. rotatable bonds :	2
Num. H-bond acceptors :	1.0
Num. H-bond donors :	2.0
Molar Refractivity :	50.39
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) :	-5.45 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.0
Log Po/w (XLOGP3) :	2.68
Log Po/w (WLOGP) :	2.15
Log Po/w (MLOGP) :	2.34
Log Po/w (SILICOS-IT) :	1.11
Consensus Log Po/w :	1.66

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.87
Solubility :	0.233 mg/ml ; 0.00135 mol/l
Class :	Soluble
Log S (Ali) :	-3.13
Solubility :	0.128 mg/ml ; 0.000739 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.85
Solubility :	0.243 mg/ml ; 0.00141 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.22

Safety of [ 53661-18-0 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302+H312+H332-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 53661-18-0 ]

* 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.

Upstream synthesis route of [ 53661-18-0 ]
Downstream synthetic route of [ 53661-18-0 ]

[ 53661-18-0 ] Synthesis Path-Upstream 1~3

1
[ 589-16-2 ]
[ 53661-18-0 ]

Yield	Reaction Conditions	Operation in experiment
95%	Stage #1: With hydrogenchloride; sodium nitrite In water at 0℃; for 1 h; Stage #2: With hydrogenchloride; tin(ll) chloride In water at -10℃; for 1.5 h;	150 ml of water and 160 ml of 12N hydrochloric acid are added to 24.2 g (0.2 mol) of 4-ethylaniline. The mixture is cooled to 0 C. and 14 g (0.2 mol) of sodium nitrite dissolved in 140 ml of water are then introduced dropwise. After 1 hour at 0 C., 112 g (0.496 mol) of stannous chloride dihydrate dissolved in 90 ml of 12 N hydrochloric acid are added to the reaction mixture, at 10 C. After 1 hour 30 at 10 C., the reaction mixture is ltered in order to obtain a brown solid, m.p.=198 C.; yield=95percent.

Reference： [1] Patent: US2004/43995, 2004, A1, . Location in patent: Page 13
[2] Journal of Medicinal Chemistry, 1999, vol. 42, # 3, p. 526 - 531
[3] Journal of the Chinese Chemical Society, 2018, vol. 65, # 5, p. 538 - 547
[4] European Journal of Medicinal Chemistry, 2018, vol. 156, p. 137 - 147

2
[ 1585-07-5 ]
[ 53661-18-0 ]

Yield	Reaction Conditions	Operation in experiment
55%	Stage #1: With potassium phosphate; N,N'-bis(2,5-dimethylpyrrol-1-yl)oxalamide; cetyltrimethylammonim bromide; copper(I) bromide In water at 80℃; for 0.166667 h; Sealed tube; Inert atmosphere Stage #2: With hydrazine hydrate In water at 80℃; for 2 h; Sealed tube; Inert atmosphere Stage #3: With hydrogenchloride In dichloromethane; water	General procedure: CuBr (36 mg, 0.25 mmol, 2.5 mol percent), L3 (110 mg, 0.4 mmol,4 mol percent), H2O (0.5 mL), and K3PO4 (254 mg, 1.2 mmol) were mixedin a 15 mL screw cap test tube. After STAC (110 mg, 0.3 mmol,3 mol percent) and aryl bromide (10 mmol) were added, the resulting mixture was stirred at 80-110° C (bath temperature) for 10 min.Then K3PO4 (2.29 g, 10.8 mmol) and N2H4*H2O (1 g, 20 mmol) were added and argon (flow rate 5-7 mL/min) was bubbled through thereaction mixture for 5 min.28 The reaction mixture was stirred ina closed test tube at 80-110° C (bath temperature) for 1-2 h until complete consumption of starting material was observed as monitoredby TLC (eluentehexane), then cooled to room temperatureand diluted with SH2Cl2 (50 mL). The resulting solutionwas filteredand washed with brine (225 mL). Aq HCl (37percent) was added to the CH2Cl2 solution dropwise until pH 3-4. The formed precipitate was filtered, washed with SH2Cl2 (15 mL) and dried atroom temperature. NMR spectra of certain synthesized aryl hydrazine hydrochlorides showed that they contained 1-5 mol percent of the corresponding aniline hydrochlorides as impurities (see Supplementary data). Analytical samples of aryl hydrazine hydrochlorides were purified via precipitation from methanol solution by adding 2-3 volumes of diethyl ether.

Reference： [1] Tetrahedron, 2014, vol. 70, # 26, p. 4043 - 4048

3
[ 25309-64-2 ]
[ 53661-18-0 ]

Reference： [1] Chinese Journal of Chemistry, 2018, vol. 36, # 11, p. 1003 - 1006

[ 53661-18-0 ] Synthesis Path-Downstream 1~36

1
[ 23572-06-7 ]
[ 53661-18-0 ]
[ 80823-83-2 ]
[ 128102-51-2 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions II,1990,p. 215 - 221

2
[ 53661-18-0 ]
[ 78-93-3 ]
N-(4-Ethyl-phenyl)-N'-[1-methyl-prop-(E)-ylidene]-hydrazine [ No CAS ]

Reference： [1]Journal of Organic Chemistry USSR (English Translation),1983,p. 388 - 392
Zhurnal Organicheskoi Khimii,1983,vol. 19,p. 445 - 450

3
[ 32464-55-4 ]
[ 53661-18-0 ]
[ 222733-82-6 ]

Reference： [1]Journal of Medicinal Chemistry,1999,vol. 42,p. 526 - 531

4
[ 589-16-2 ]
[ 53661-18-0 ]

Yield	Reaction Conditions	Operation in experiment
95%		150 ml of water and 160 ml of 12N hydrochloric acid are added to 24.2 g (0.2 mol) of 4-ethylaniline. The mixture is cooled to 0 C. and 14 g (0.2 mol) of sodium nitrite dissolved in 140 ml of water are then introduced dropwise. After 1 hour at 0 C., 112 g (0.496 mol) of stannous chloride dihydrate dissolved in 90 ml of 12 N hydrochloric acid are added to the reaction mixture, at 10 C. After 1 hour 30 at 10 C., the reaction mixture is ltered in order to obtain a brown solid, m.p.=198 C.; yield=95%.
		General procedure: dissolve the substituted anline (3 mmol) in HCl aq (6 M) at -5 C,and slowly added an aqueous solution of NaNO2 (0.23 g, 3.3 mmol).The mixture was stirred for further 0.5 h, a solution of SnCl2 (1.7 g,7.5 mmol) dissolved in concentrated HCl was added dropwise, then the resulting mixture was moved to room temperature and stirred for further1 h. The muddy mixture was filtered out, washed with a small amount of HCl solution and dried in vacuum. This desired phenylhydrazine hydrochloride intermediate was used directly without additional purification.To a solution of substituted benzyl halide 3 mmol in EtOH was added the hydrazine hydrate 30 mmol, and the mixture was stirred atroom temperature overnight till the reaction was completed monitored by TLC. The reaction mixture was concentrated to dryness, and redissolvedin a little EtOH, then added an aqueous HCl (12 M) andstirred for a while at 0 C. The resulting precipitate was collected byfiltration and dried. This desired benzylhydrazine hydrochloride intermediatewas used directly without additional purification.
		General procedure: Concentrated hydrochloric acid (30mmol, 2.5mL, 12M) was added to phenylaniline (10mmol) and the resulting white suspension was cooled to 0C, then appropriate amount of water was added to dissolve the white solid. Sodium nitrite (11mmol) in 10mL of water, precooled to 0C, was slowly added to the solution of phenylaniline hydrochloride. The temperature of the reaction was maintained at 0C for 0.5h. The diazonium salt solution was treated with a solution of stannous chloride hydrate (40mmol) in 15mL of concentrate hydrochloric acid (12M), then stirred for another 4hat 0C. A light brown solid which formed was collected by filtration, washed with little precooled ethyl alcohol and dichloromethane, the crude product was used without further purification.

Reference： [1]Patent: US2004/43995,2004,A1 .Location in patent: Page 13
[2]Journal of Medicinal Chemistry,1999,vol. 42,p. 526 - 531
[3]Journal of the Chinese Chemical Society,2018,vol. 65,p. 538 - 547
[4]Bioorganic and Medicinal Chemistry,2019,vol. 27,p. 3179 - 3193
[5]European Journal of Medicinal Chemistry,2018,vol. 156,p. 137 - 147

5
[ 53661-18-0 ]
[ 62500-88-3 ]

Reference： [1]Journal of Medicinal Chemistry,1999,vol. 42,p. 526 - 531

6
[ 617-35-6 ]
[ 53661-18-0 ]
ethyl 2-[2-(4-ethylphenyl)-hydrazono]propanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
94%	In ethanol; for 3.5h;Heating / reflux;	23 ml (0.2 mol) of ethyl pyruvate are added to 34.5 g (0.2 mol) of <strong>[53661-18-0]4-ethylphenylhydrazine hydrochloride</strong> prepared above in suspension in 500 ml of ethanol, and the reaction miXture is heated for 3 hours 30 at ref The miXture is then cooled to a temperature of 200 C. and the ethanol is evaporated off. The soud residue is washed with pentane and dried at 40 C. under vacuum in order to obtain a colourless liquid; yield=94%.

Reference： [1]Patent: US2004/43995,2004,A1 .Location in patent: Page 13; 14

7
[ 1445-73-4 ]
[ 53661-18-0 ]
[ 1147937-58-3 ]

Yield	Reaction Conditions	Operation in experiment
82%		Example 8A[0405] Sulfuric acid (2 mL) was added to a solution of 4-Ethyl phenyl hydrazine hydrochloride (2.0 g, 11 mmol) in dioxane (30 mL), and allowed to stir for 5 min at RT. N- methylpiperidone (1.7 g, 13 mmol) was added and the mixture was heated at 80 0C for 3 h. After completion of reaction (monitored by TLC), reaction mixture was concentrated to -20 mL under reduced pressure and basified to pH 10 using 10% aqueous KOH solution. The mixture was extracted with EtOAc (3x100 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure using rotary evaporator to provide the desired compound as a brown colored solid (0.35g , 82% yield).

Reference： [1]Patent: WO2010/51501,2010,A1 .Location in patent: Page/Page column 237-238

8
[ 53661-18-0 ]
[ 1370410-13-1 ]

Reference： [1]Organic Letters,2012,vol. 14,p. 2066 - 2069

9
[ 53661-18-0 ]
[ 1370410-33-5 ]

Reference： [1]Organic Letters,2012,vol. 14,p. 2066 - 2069

10
[ 53661-18-0 ]
[ 1370410-43-7 ]

Reference： [1]Organic Letters,2012,vol. 14,p. 2066 - 2069
[2]Organic Letters,2012,vol. 14,p. 2066 - 2069

11
[ 53661-18-0 ]
[ 78-93-3 ]
[ 85654-50-8 ]

Reference： [1]Organic Letters,2012,vol. 14,p. 2066 - 2069
[2]Tetrahedron,2014,vol. 70,p. 312 - 317

12
[ 53661-18-0 ]
[ 18326-16-4 ]
11-ethyl-4-isopropyl-7,7,13a-trimethyl-6,6a,7,8,13,13a-hexahydro-5H-naphtho[2,1-b]carbazol-3-ol [ No CAS ]

Reference： [1]ACS Medicinal Chemistry Letters,2012,vol. 3,p. 818 - 822,5

13
[ 53661-18-0 ]
[ 18326-16-4 ]
C₂₉H₃₇NO [ No CAS ]

Reference： [1]ACS Medicinal Chemistry Letters,2012,vol. 3,p. 818 - 822,5

14
[ 53661-18-0 ]
[ 1522364-37-9 ]

Reference： [1]Tetrahedron,2014,vol. 70,p. 312 - 317

15
[ 53661-18-0 ]
[ 1522364-16-4 ]

Reference： [1]Tetrahedron,2014,vol. 70,p. 312 - 317

16
[ 1585-07-5 ]
[ 53661-18-0 ]

Yield	Reaction Conditions	Operation in experiment
55%		General procedure: CuBr (36 mg, 0.25 mmol, 2.5 mol %), L3 (110 mg, 0.4 mmol,4 mol %), H2O (0.5 mL), and K3PO4 (254 mg, 1.2 mmol) were mixedin a 15 mL screw cap test tube. After STAC (110 mg, 0.3 mmol,3 mol %) and aryl bromide (10 mmol) were added, the resulting mixture was stirred at 80-110 C (bath temperature) for 10 min.Then K3PO4 (2.29 g, 10.8 mmol) and N2H4*H2O (1 g, 20 mmol) were added and argon (flow rate 5-7 mL/min) was bubbled through thereaction mixture for 5 min.28 The reaction mixture was stirred ina closed test tube at 80-110 C (bath temperature) for 1-2 h until complete consumption of starting material was observed as monitoredby TLC (eluentehexane), then cooled to room temperatureand diluted with SH2Cl2 (50 mL). The resulting solutionwas filteredand washed with brine (225 mL). Aq HCl (37%) was added to the CH2Cl2 solution dropwise until pH 3-4. The formed precipitate was filtered, washed with SH2Cl2 (15 mL) and dried atroom temperature. NMR spectra of certain synthesized aryl hydrazine hydrochlorides showed that they contained 1-5 mol % of the corresponding aniline hydrochlorides as impurities (see Supplementary data). Analytical samples of aryl hydrazine hydrochlorides were purified via precipitation from methanol solution by adding 2-3 volumes of diethyl ether.

Reference： [1]Tetrahedron,2014,vol. 70,p. 4043 - 4048

17
[ 201230-82-2 ]
[ 19820-56-5 ]
[ 53661-18-0 ]
2-(4-ethylphenyl)phthalazin-1(2H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60%	With palladium(II) trifluoroacetate; 1,3-bis-(diphenylphosphino)propane; magnesium sulfate; 1,8-diazabicyclo[5.4.0]undec-7-ene; In acetonitrile; at 150℃; under 7500.75 Torr; for 21h;Autoclave;	General procedure: 2-Formylaryl tosylate (2 mmol), hydrazine (2 mmol), Pd(TFA)2 (5 mol%), dppp (10 mol%), DBU (2.4 mmol), anhydrous MgSO4 (2 mmol) and CH3CN (30 ml) were charged in a 200 ml-autoclave. The autoclave was flushed using CO three times. The reaction was pressurized with CO to 1.0 MPa, and stirred at 140 C for 21 h. Then the mixture was cooled to room temperature and the excess CO was vented. Solvent was removed under reduced pressure and the crude residue was purified by column chromatography on silica gel with petroleum ether-ethyl acetate as the eluent to afford the desired product.

Reference： [1]Tetrahedron,2016,vol. 72,p. 8282 - 8286

18
[ 110-91-8 ]
[ 201230-82-2 ]
[ 53661-18-0 ]
4-[(4-ethylphenyl)carbonyl]morpholine [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2017,vol. 82,p. 4970 - 4976

19
[ 201230-82-2 ]
[ 53661-18-0 ]
[ 536-74-3 ]
1,5-bis(4-ethylphenyl)-3-phenyl-1H-pyrazole [ No CAS ]

Reference： [1]Organic Letters,2017,vol. 19,p. 3466 - 3469

20
[ 696-63-9 ]
[ 53661-18-0 ]
(4-ethylphenyl)(4-methoxyphenyl)sulfane [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2018,vol. 83,p. 2389 - 2394

21
[ 22478-66-6 ]
[ 53661-18-0 ]
C₂₈H₃₈N₂O [ No CAS ]

Reference： [1]Journal of the Chinese Chemical Society,2018,vol. 65,p. 538 - 547

22
[ 22478-66-6 ]
[ 53661-18-0 ]
2-dehydroabietyl-4-(4-ethylphenyl)-4H-1,3,4-oxadiazin-5(6H)-one [ No CAS ]

Reference： [1]Journal of the Chinese Chemical Society,2018,vol. 65,p. 538 - 547

23
3-phenylamino-2-(3,4,5-trimethoxybenzoyl)acrylonitrile [ No CAS ]
[ 53661-18-0 ]
(5-amino-1-(4-ethylphenyl)-1H-pyrazol-4-yl) (3,4,5-trimethoxyphenyl)methanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
0.32 g	In ethanol; at 120℃; for 0.166667h;Microwave irradiation; Sealed tube; Alkaline conditions;	General procedure: A mixture of 3-(phenylamino)-2-(3,4,5-trimethoxybenzoyl)acrylonitrile (1mmol), substituted phenylhydrazine hydrochloride (1mmol) and trimethylamine(1mmol) in ethanol was irradiated in the sealed tube at 120C for 10min using a CEM Discover microwave synthesizer. After cooling to room temperature, the mixture was concentrated in vacuo, purification by column chromatography on the silica gel to get the pure product.

Reference： [1]European Journal of Medicinal Chemistry,2018,vol. 156,p. 137 - 147

24
3-phenylamino-2-(3,4,5-trimethoxybenzoyl)acrylonitrile [ No CAS ]
[ 53661-18-0 ]
(1-(4-ethylphenyl)-1H-pyrazol-4-yl) (3,4,5-trimethoxyphenyl)methanone [ No CAS ]

Reference： [1]European Journal of Medicinal Chemistry,2018,vol. 156,p. 137 - 147

25
[ 25309-64-2 ]
[ 53661-18-0 ]

Reference： [1]Chinese Journal of Chemistry,2018,vol. 36,p. 1003 - 1006

26
2-(3-carbamoyl-2,4-difluorophenoxy)acetic acid [ No CAS ]
[ 53661-18-0 ]
C₁₇H₁₇F₂N₃O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		General procedure: A 10 mL round-bottom flask equipped with a magnetic stirrer was charged with 7 or 13 (0.26 mmol), EDCI (55 mg, 0.29 mmol), HOBt(39 mg, 0.29 mmol) and THF (5 mL), DMF (1 mL), this mixture wasstirred at room temperature for 3 h. Then the intermediate 10 (0.4 mmol) and followed DIPEA (155 mg, 1.2 mmol) were added to the reaction, and stirred overnight. The mixture was then diluted withEtOAc (30 mL), washed with NH4Cl (aq) and brine, dried over Na2SO4,concentrated in a rotovapor, and purified on silica gel. Elution withDCM/MeOH (30:1) afforded the according products 11 or 14 in goodyield. Example 11-A12, 1H NMR (600 MHz, DMSO-d6) delta 10.04 (s, 1H),8.14 (s, 1H), 8.00 (s, 1H), 7.86 (s, 1H), 7.21-7.14 (m, 3H), 7.13-7.08(m, 1H), 6.71 (d, J=6.8 Hz, 2H), 4.75 (s, 2H). ESI-MS calcd forC15H13ClF2N3O3 [M+H]+, 356.1, found 356.3.The above acylhydrazine intermediate 11 or 14 was dissolved inTHF (5 mL), and triphosgene (2 eq) was added, the mixture was stirredat room temperature for 1 h. Upon completion, the reaction mixturewas then diluted with EtOAc (25 mL), washed with brine, dried overNa2SO4, concentrated in vacuum, and purified on silica gel. Elutionwith petroleum ether/EtOAc (2:1 to 1:1) afforded the according productsin good yield.

Reference： [1]Bioorganic and Medicinal Chemistry,2019,vol. 27,p. 3179 - 3193

27
2-(3-carbamoyl-2,4-difluorophenoxy)acetic acid [ No CAS ]
[ 53661-18-0 ]
2,6-difluoro-3-((4-(4-ethylphenyl)-5-oxo-1,3,4-oxadiazol-2-yl)methoxy)benzamide [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2019,vol. 27,p. 3179 - 3193

28
[ 17751-36-9 ]
[ 53661-18-0 ]
C₂₉H₃₅NO₂ [ No CAS ]

Reference： [1]Journal of Enzyme Inhibition and Medicinal Chemistry,2019,vol. 34,p. 1544 - 1561

29
[ 53661-18-0 ]
2,3,4,4a,9,13c-hexahydro-12-ethyl-7-isopropyl-1,4a-dimethyl-9-(2-(piperazin-1-yl)ethyl)-1H-dibenzo[a,c]carbazole-1-carboxylic acid methyl ester [ No CAS ]

Reference： [1]Journal of Enzyme Inhibition and Medicinal Chemistry,2019,vol. 34,p. 1544 - 1561

30
[ 53661-18-0 ]
C₃₁H₃₈BrNO₂ [ No CAS ]

Reference： [1]Journal of Enzyme Inhibition and Medicinal Chemistry,2019,vol. 34,p. 1544 - 1561

31
[ 119-64-2 ]
[ 53661-18-0 ]
8-ethyl-11H-benzo[a]carbazole [ No CAS ]

Reference： [1]Organic Letters,2019,vol. 21,p. 7179 - 7183

32
[ 53661-18-0 ]
[ 79-22-1 ]
C₁₀H₁₄N₂O₂ [ No CAS ]

Reference： [1]Organic Letters,2019,vol. 21,p. 7519 - 7523

33
[ 53661-18-0 ]
C₂₉H₂₄F₆N₂O₄ [ No CAS ]

Reference： [1]Organic Letters,2019,vol. 21,p. 7519 - 7523

34
[ 53661-18-0 ]
(S)-4-(3,5-bis(trifluoromethyl)benzyl) 1-methyl 2-(4-ethylphenyl)-3-phenyl-2,3-dihydro-1H-pyrazole-1,4-dicarboxylate [ No CAS ]

Reference： [1]Organic Letters,2019,vol. 21,p. 7519 - 7523

35
[ 53661-18-0 ]
C₁₀H₁₂N₂O₂ [ No CAS ]

Reference： [1]Organic Letters,2019,vol. 21,p. 7519 - 7523

36
[ 5994-87-6 ]
[ 53661-18-0 ]
P,P-diphenyl-N-(4-ethylphenyl) phosphinic amide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88%	With di-tert-butyl peroxide; copper diacetate; caesium carbonate; In 1,2-dichloro-ethane; at 80℃; for 6h;	General procedure: Under the air atmosphere, a Schlenk tube (35 mL) equipped with a magnetic bar, arylhydrazine hydrochloride 2 (0.6 mol in three portions at the interval of 2 hours) was added to the mixture of phosphoryl amide 1 (0.3 mmol), Cu(OAc)2 (10 mol%), DTBP (0.6 mmol), Cs2CO3 (0.6 mmol) in dry DCE (3.0 mL). Then, the reaction mixture was allowed to stir at 80 C for 6 hours. After the consumption of 1, as monitored by TLC analysis, the mixture was filtered through a short celite pad and washed with methane (15mL x 3). The filtrate was concentrated, and the oily crude product was purified by column chromatography using silica gel (200-300 mesh) as stationary phase and a mixture of n-hexane and ethyl acetate (ca. 5:1) as eluent to give the corresponding arylated products 3 (Rf=ca.0.3 otherwise noted).

Reference： [1]Synthetic Communications,2020,vol. 50,p. 947 - 957

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Ghs Precautionary Statements

Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

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Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 53661-18-0 ] {[proInfo.proName]}

Quality Control of [ 53661-18-0 ]

Related Doc. of [ 53661-18-0 ]

Product Details of [ 53661-18-0 ]

Calculated chemistry of [ 53661-18-0 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 53661-18-0 ]

Application In Synthesis of [ 53661-18-0 ]

[ 53661-18-0 ] Synthesis Path-Upstream 1~3

[ 53661-18-0 ] Synthesis Path-Downstream 1~36

Related Functional Groups of [ 53661-18-0 ]

Aryls

Amines

Hydrazines

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 53661-18-0 ]