[ CAS No. 635-26-7 ] {[proInfo.proName]}

Name: 635-26-7|o-Tolylhydrazine hydrochloride|97%
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Quality Control of [ 635-26-7 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 635-26-7 ]

Product Details of [ 635-26-7 ]

CAS No. :	635-26-7	MDL No. :	MFCD00012925
Formula :	C₇H₁₁ClN₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	KJGFNDCSTWGUDT-UHFFFAOYSA-N
M.W :	158.63	Pubchem ID :	71554
Synonyms :

Calculated chemistry of [ 635-26-7 ]

Physicochemical Properties

Num. heavy atoms :	10
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 :	44.47
TPSA :	38.05 Å²

Pharmacokinetics

GI absorption :	Low
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.7 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.0
Log Po/w (XLOGP3) :	2.21
Log Po/w (WLOGP) :	-1.79
Log Po/w (MLOGP) :	2.02
Log Po/w (SILICOS-IT) :	0.81
Consensus Log Po/w :	0.65

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.56

Water Solubility

Log S (ESOL) :	-2.59
Solubility :	0.404 mg/ml ; 0.00255 mol/l
Class :	Soluble
Log S (Ali) :	-2.64
Solubility :	0.36 mg/ml ; 0.00227 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.43
Solubility :	0.589 mg/ml ; 0.00372 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.01

Safety of [ 635-26-7 ]

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 [ 635-26-7 ]

* 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 [ 635-26-7 ]
Downstream synthetic route of [ 635-26-7 ]

[ 635-26-7 ] Synthesis Path-Upstream 1~2

1
[ 95-53-4 ]
[ 635-26-7 ]

Reference： [1] Journal of Heterocyclic Chemistry, 1995, vol. 32, # 1, p. 1 - 11
[2] European Journal of Medicinal Chemistry, 2010, vol. 45, # 10, p. 4692 - 4696
[3] Bulletin of the Korean Chemical Society, 2010, vol. 31, # 11, p. 3341 - 3347
[4] Journal of Agricultural and Food Chemistry, 2014, vol. 62, # 2, p. 381 - 390
[5] Advanced Synthesis and Catalysis, 2014, vol. 356, # 7, p. 1571 - 1576
[6] Bioorganic Chemistry, 2014, vol. 57, p. 30 - 42
[7] Bioorganic Chemistry, 2014, vol. 57, p. 30 - 42
[8] Advanced Synthesis and Catalysis, 2015, vol. 357, # 4, p. 761 - 766
[9] Journal of Chemical Research, 2015, vol. 39, # 10, p. 594 - 600
[10] Bioorganic and Medicinal Chemistry Letters, 2018, vol. 28, # 3, p. 529 - 532
[11] Journal of the Chinese Chemical Society, 2018, vol. 65, # 5, p. 538 - 547
[12] European Journal of Medicinal Chemistry, 2018, vol. 156, p. 137 - 147

2
[ 529-27-1 ]
[ 635-26-7 ]

Yield	Reaction Conditions	Operation in experiment
39.5%	at 65℃;	The pure product is dissolved in 100 g 2 - methyl phenyl hydrazine 69 ml 37percent in hydrochloric acid, in the 65 °C stirring to the reaction solution to crystallize, cooling to 20 °C, filtering, washing the filter cake for acetone, and dried to obtain 2 - methyl phenyl hydrazine hydrochloride product 110 g, content 99.2percent, yield 39.5percent.

Reference： [1] Patent: CN107814750, 2018, A, . Location in patent: Paragraph 0026; 0027; 0035; 0036; 0046

[ 635-26-7 ] Synthesis Path-Downstream 1~77

1
[ 64-17-5 ]
[ 41068-36-4 ]
[ 127-08-2 ]
[ 635-26-7 ]
4-(1-<i>o</i>-tolylazo-vinyl)-anisole [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1950,vol. 72,p. 5238

2
[ 635-26-7 ]
[ 17396-35-9 ]
[ 88892-73-3 ]

Reference： [1]Journal of general chemistry of the USSR,1963,vol. 33,p. 3331 - 3335
Zhurnal Obshchei Khimii,1963,vol. 33,p. 3403 - 3408

3
[ 80370-42-9 ]
[ 635-26-7 ]
[ 741717-64-6 ]

Reference： [1]Journal of Heterocyclic Chemistry,1993,vol. 30,p. 865 - 872

4
[ 95-46-5 ]
[ 635-26-7 ]
[ 605-39-0 ]

Yield	Reaction Conditions	Operation in experiment
99%	With sodium hydroxide; mercury dichloride; palladium dichloride In methanol for 6h; Heating;

Reference： [1]Nakajima; Kinosada; Tamura; Hara [Bulletin of the Chemical Society of Japan, 1983, vol. 56, # 4, p. 1113 - 1115]

5
[ 2161-40-2 ]
[ 635-26-7 ]
[ 53526-97-9 ]

Yield	Reaction Conditions	Operation in experiment
31%	With triethylamine In methanol Heating;

Reference： [1]Nozoe, Tetsuo; Imafuku, Kimiaki; Yin, Bing-Zhu; Honda, Masaaki; Goto, Yasutomo; et al. [Bulletin of the Chemical Society of Japan, 1988, vol. 61, p. 2531 - 2540]

6
[ 38768-08-0 ]
[ 635-26-7 ]
[ 53526-97-9 ]
6,6'-bis<(o-tolyl)hydrazono>-1,1'-bi(2,4-cycloheptadiene)-7,7'-dione [ No CAS ]

Reference： [1]Bulletin of the Chemical Society of Japan,1988,vol. 61,p. 2531 - 2540

7
[ 16676-29-2 ]
[ 635-26-7 ]
[ 126642-50-0 ]

Yield	Reaction Conditions	Operation in experiment
55%	With hydrogenchloride In ethanol for 5h; Heating;

Reference： [1]Portoghese; Sultana; Takemori [Journal of Medicinal Chemistry, 1990, vol. 33, # 6, p. 1714 - 1720]

8
[ 635-26-7 ]
[ 40876-98-0 ]
[ 87499-04-5 ]

Yield	Reaction Conditions	Operation in experiment
22%	With acetic acid; In water; toluene; at 20℃; for 5h;Heating / reflux;	To a mixture of diethyl oxalacetate sodium salt (10.5 g, 50 mmol), acetic acid (100 mL) and toluene (50 mL) was added an aqueous solution (50 mL) of (2-methylphenyl)hydrazine hydrochloride (7.93 g, 50 mmol) under stirring at room temperature, and the mixture was heated under reflux for 3 hr. After cooling, the reaction mixture was partitioned. The organic layer was washed with water and saturated brine, dried, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1-3/1) to give yellow crystals. This product was dissolved in acetic acid (36 mL), and the mixture was heated under reflux for 2 hr. After cooling, the reaction mixture was concentrated under reduced pressure, and recrystallized from hexane-ethyl acetate to give the title compound (2.69 g, yield 22%) as colorless crystals. 1H NMR (CDCl3) delta: 1.30 (3H, t, J=7.2Hz), 2.02 (3H, s), 3.74(1H, s), 4.33(2H, q, J=7.2Hz), 5.94(1H, s), 7.13-7.36(4H, m).

Reference： [1]Chemical and Pharmaceutical Bulletin,1983,vol. 31,p. 1228 - 1234
[2]Patent: EP1726580,2006,A1 .Location in patent: Page/Page column 51

9
[ 95-53-4 ]
[ 635-26-7 ]

Yield	Reaction Conditions	Operation in experiment
		General procedure: To a mixture of substituted phenyl amine (0.06 mol) and 15% HCl (60 mL), NaNO2 (5 g, 0.072 mol) in H2O (200 mL) was added drop-wise at 0 C. After the completion of addition, the reaction mixture was stirred at this temperature for 30 min. and then was dropped into the mixture of saturated solution of sodium hydrogen sulfite (22.5 g, 0.216 mol), keeping the reaction below 20 C. Upon completing the addition, the reaction was heated under refluxed for 3 h and cooled to room temperature. The solid is filtered and washed with ethyl acetate and the cake was dried to give white solid 9a-h yielded 90%.
		General procedure: To a mixture of substituted phenyl amine (0.06 mol) and 15%HCl (60 mL), NaNO2 (5 g, 0.072 mol) in H2O (200 mL) was addeddrop-wise at 0 C. After the completion of addition, the reaction mixture was stirred at this temperature for 30 min. and then wasdropped into the mixture of saturated solution of sodium hydrogen sulfite (22.5 g, 0.216 mol), keeping the reaction below 20 C. Upon completing the addition, the reaction was heated under refluxed for 3 h and cooled to room temperature. The solid is filtered and washed with ethyl acetate and the cake was dried to give white solid 9a-h yielded 90%.
		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]Journal of Heterocyclic Chemistry,1995,vol. 32,p. 1 - 11
[2]European Journal of Medicinal Chemistry,2010,vol. 45,p. 4692 - 4696
[3]Bulletin of the Korean Chemical Society,2010,vol. 31,p. 3341 - 3347
[4]Journal of Agricultural and Food Chemistry,2014,vol. 62,p. 381 - 390
[5]Advanced Synthesis and Catalysis,2014,vol. 356,p. 1571 - 1576
[6]Bioorganic Chemistry,2014,vol. 57,p. 30 - 42
[7]Bioorganic Chemistry,2014,vol. 57,p. 30 - 42
[8]Advanced Synthesis and Catalysis,2015,vol. 357,p. 761 - 766
[9]Journal of Chemical Research,2015,vol. 39,p. 594 - 600
[10]Bioorganic and Medicinal Chemistry Letters,2018,vol. 28,p. 529 - 532
[11]Journal of the Chinese Chemical Society,2018,vol. 65,p. 538 - 547
[12]Bioorganic and Medicinal Chemistry,2019,vol. 27,p. 3179 - 3193
[13]European Journal of Medicinal Chemistry,2018,vol. 156,p. 137 - 147

10
[ 67-56-1 ]
[ 126727-04-6 ]
[ 635-26-7 ]
[ 1501-05-9 ]
3-Phenyl-2-[3-(2-o-tolyl-1H-indol-3-yl)-propionylamino]-propionic acid methyl ester [ No CAS ]

Reference： [1]Tetrahedron Letters,1996,vol. 37,p. 4869 - 4872

11
[ 59997-51-2 ]
[ 635-26-7 ]
[ 337533-96-7 ]

Yield	Reaction Conditions	Operation in experiment
93%		4,4-Dimethyl-3-oxopentanenitrile (36.7 g, 0.29 mol), <strong>[635-26-7](2-methylphenyl)hydrazine hydrochloride</strong> (47.7 g, 0.29 mol), and glacial acetic acid (7.03 g, 6.7 mL, 0.12 mol) were dissolved in abs ethanol (585 mL) and heated under reflux for 18 h. After removal of the solvent under reduced pressure, EtOAc and water (500 mL each) were added, then sodium bicarbonate (42 g, 0.50 mol) was carefully added. After addition of hexane (500 mL), the organic phase was separated, washed with brine (500 mL), and dried over Na2SO4. The mixture was then filtered through a pad of silica gel (500 g) on a sintered glass funnel. The pad was eluted with hexanes/EtOAc (1:1, v/v), and the filtrate was concentrated under reduced pressure. The resulting solid was triturated with hexanes/EtOAc (9:1, v/v), filtered, washed and dried in vacuo to afford the product as a colorless solid (61.5 g, 93%). 1H NMR (400 MHz, CD2Cl2) 61.29 (s, 9H), 2.12 (s, 3H), 3.56 (br, 2H), 5.48 (s, 1H), 7.28 (m, 2H), 7.31 (m, 2H).
93%		4, 4-Dimethyl-3-oxopentanenitrile (36.7 g, 0.29 mol), (2-methylphenyl) hydrazine hydrochloride (47.7 g, 0.29 mol), and glacial acetic acid (7.03 g, 6.7 mL, 0.12 mol) were dissolved in abs ethanol (585 mL) and heated under reflux for 18 h. After removal of the solvent under reduced pressure, EtOAc and water (500 mL each) were added, then sodium bicarbonate (42 g, 0.50 mol) was carefully added. After addition of hexane (500 mL), the organic phase was separated, washed with brine (500 mL), and dried over Na2S04. The mixture was then filtered through a pad of silica gel (500 g) on a sintered glass funnel. The pad was eluted with hexanes/EtOAc (1: 1, v/v), and the filtrate was concentrated under reduced pressure. The resulting solid was triturated with hexanes/EtOAc (9: 1, v/v), filtered, washed and dried in vacuo to afford a colorless solid (61.5 g, 93 %).'H NMR (400 MHz, CD2CI2) 8 1.29 (s, 9H), 2.12 (s, 3H), 3.56 (br, 2H), 5.48 (s, 1H), 7.28 (m, 2H), 7.31 (m, 2H).
	With triethylamine; In toluene; at 110℃;	Step 34.1 : 5-tert-Butyl-2-o-tolyl-2H-pyrazol-3-ylamine; EPO <DP n="79"/>A solution of o-tolyl-hydrazine hydrochloride (0.3 mmol) in 0.5 mL of toluene with 4,4- dimethyl-3-oxopentanenitrile (375 mg, 3 mmol, 10 equiv) and Et3N (84 muL, 0.6 mmol, 2 equiv) is stirred at 1100C overnight. The solvent is evaporated and the residue taken up in EtOAC and washed with saturated NaHCO3 and brine. The organic layer is then concentrated and the residue diluted in 1 mL of ethanol and 1 mL of 1M HCI. The mixture was left at rt for 15 min and then it was concentrated. 5-tert-Butyl-2-o-tolyl-2H-pyrazol-3- ylamine is used crude in the preparation of Example 34.

Reference： [1]Patent: US2005/192294,2005,A1 .Location in patent: Page/Page column 13
[2]Patent: WO2004/50650,2004,A1 .Location in patent: Page 26-27
[3]Journal of the American Chemical Society,2009,vol. 131,p. 13286 - 13296
[4]Journal of Medicinal Chemistry,2002,vol. 45,p. 2994 - 3008
[5]Patent: WO2006/108640,2006,A1 .Location in patent: Page/Page column 77-78

12
[ 617-35-6 ]
[ 635-26-7 ]
[ 70761-93-2 ]

Yield	Reaction Conditions	Operation in experiment
	With toluene-4-sulfonic acid In benzene for 12h; Heating;

Reference： [1]Jablonowski, Jill A.; Grice, Cheryl A.; Chai, Wenying; Dvorak, Curt A.; Venable, Jennifer D.; Kwok, Annette K.; Ly, Kiev S.; Wei, Jianmei; Baker, Sherry M.; Desai, Pragnya J.; Jiang, Wen; Wilson, Sandy J.; Thurmond, Robin L.; Karlsson, Lars; Edwards, James P.; Lovenberg, Timothy W.; Carruthers, Nicholas I. [Journal of Medicinal Chemistry, 2003, vol. 46, # 19, p. 3957 - 3960]

13
[ 110-87-2 ]
[ 635-26-7 ]
[ 29957-87-7 ]

Reference： [1]Phosphorus, Sulfur and Silicon and the Related Elements,2009,vol. 184,p. 1843 - 1853
[2]Organic Letters,2004,vol. 6,p. 79 - 82
[3]Organic Letters,2017,vol. 19,p. 6336 - 6339

14
[ 1118-61-2 ]
[ 635-26-7 ]
[ 91331-68-9 ]

Yield	Reaction Conditions	Operation in experiment
90%		General procedure: In a 2-5mL microwave vial containing a stir bar, 3-aminocrotonitrile (164 mg, 2mmol) and 5 mL of 1M HCl were combined with stirring to give a 0.4 M solution of starting material. Next, phenylhydrazine (216 mg, 2 mmol) was added to the solution. The microwave vial was then sealed with an aluminum cap and irradiated in the microwave reactor at 150 C for 10 m with the absorbance set to ?very high.? After cooling, the orange sludge-containing heterogeneous solution was basified with 10% NaOH and was sonicated for 5 m to produce a visible solid precipitate. The precipitate was filtered, washed twice with D.I. water, and then dried to yield the product as a light orange solid (292 mg, 84% yield). For compounds that do not readily precipitate, the product can be isolated by extracting the basic aqueous layer 3x with dichloromethane (DCM). The combined organic layers are dried over magnesium sulfate, filtered and evaporated under reduced pressure to obtain the product.
87%		3-Aminocrotonitrile (2.00 g, 24.4 MMOL) was added to a stirred solution of (2- methylphenyl) hydrazine hydrochloride (3.67 g, 23.1 MMOL) in 1 M hydrochloric acid (20 mL). The reaction was heated (100C) for 18 h and then cooled to rt. The solution was adjusted to pH > 12 using 1 M aqueous sodium hydroxide. The mixture was extracted with dichloromethane (3 x 20 mL), and then the combined organic extracts were washed with brine, dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo. Flash chromatography of the residue over silica gel using 25-50% ethyl acetate/hexane afforded 3-METHYL-1-(2-METHYLPHENYL)-1H-PYRAZOL-5-AMINE (3.97 g, 87%) as an orange oil. H NMR (300 MHz, acetone-d6) 6 7.29 (m, 4 H), 5.32 (s, 1 H), 2.12 (s, 3 H), 2.08 (s, 3 H); ES-MS m/z 188.2 (MH+), HPLC RT (min) 0.79.

Reference： [1]Tetrahedron Letters,2019,vol. 60,p. 72 - 74
[2]Patent: WO2004/50650,2004,A1 .Location in patent: Page 30
[3]Chemical and Pharmaceutical Bulletin,2004,vol. 52,p. 1098 - 1104

15
[ 635-26-7 ]
[ 6946-05-0 ]
1,10-dimethyl-11,12-dihydro-11,12-diaza-indeno[2,1-<i>a</i>]fluorene [ No CAS ]

Reference： [1]Synlett,2005,p. 42 - 48

16
[ 635-26-7 ]
[ 108-94-1 ]
[ 19283-51-3 ]

Reference： [1]Synthetic Communications,2009,vol. 39,p. 158 - 165
[2]Chemical Communications,2004,p. 158 - 159
[3]Phosphorus, Sulfur and Silicon and the Related Elements,2009,vol. 184,p. 1843 - 1853
[4]Letters in Organic Chemistry,2009,vol. 6,p. 159 - 164
[5]Journal of Heterocyclic Chemistry,2010,vol. 47,p. 807 - 824
[6]Angewandte Chemie - International Edition,2018,vol. 57,p. 15891 - 15895
Angew. Chem.,2018,vol. 130,p. 16118 - 16122,5

17
[ 635-26-7 ]
[ 78-93-3 ]
[ 27505-78-8 ]

Reference： [1]Synthetic Communications,2009,vol. 39,p. 158 - 165
[2]Phosphorus, Sulfur and Silicon and the Related Elements,2009,vol. 184,p. 1843 - 1853
[3]Letters in Organic Chemistry,2009,vol. 6,p. 159 - 164
[4]Journal of Organic Chemistry,2012,vol. 77,p. 8049 - 8055,7
[5]Chemical Communications,2004,p. 158 - 159
[6]Organic Letters,2020,vol. 22,p. 4716 - 4720

18
[ 635-26-7 ]
[ 141-97-9 ]
[ 2125-44-2 ]

Yield	Reaction Conditions	Operation in experiment
58%	With sodium acetate; In acetic acid; at 100℃; for 16h;	A solution of o-tolyl-hydrazine hydrochloride (10.0 g, 63.0 mmol), sodium acetate (5.7 g, 69.3 mmol) and ethyl acetoacetate (8.2 g, 63.0 mmol) in glacial acetic acid (100 mL) was heated to 100 0C for 16 hrs. The reaction mixture was then cooled to 25 0C and the acetic acid was removed under reduced pressure. Ethyl acetate (150 mL) and water (150 mL) were added and the organic layer was separated, dried over Na2SO4 and concentrated to a brown solid. This solid was washed with ethyl acetate and <n="20"/>isolated by filtration to afford 5-methyl-2-o-tolyl-2,4-dihydro-pyrazol-3-one (6.9 g, 58%). 1H-NMR (400 MHz, d-DMSO) delta 7.29-7.15 (m, 4 H), 5.29 (s, 1 H), 2.08 <s, 3 H), 2.06 (S1 3 H).

Reference： [1]Patent: WO2008/23235,2008,A1 .Location in patent: Page/Page column 18-19

19
[ 635-26-7 ]
[ 95882-33-0 ]
[ 705278-77-9 ]

Yield	Reaction Conditions	Operation in experiment
62%	In toluene; for 16h;Heating / reflux;	A solution of (2-methylphenyl)hydrazine hydrochloride (2.00 g, 14.6 mmol) and crude <strong>[95882-33-0]3-cyclopentyl-3-oxopropanenitrile</strong> from the previous step (2.32 g, 14.6 mmol) in toluene (6 mL) was heated to reflux for 16 h. Removal of the solvent under reduced pressure provided a residue which was purified by silica gel chromatography using hexane/EtOAc (3:1, v/v) as the eluent. Concentration under reduced pressure provided 3-cyclopentyl-1-(2-methylphenyl)-1H-pyrazol-5-amine as a light orange solid (2.19 g, 62%). 1H NMR (400 MHz, CDCl3) δ 1.58-1.82 (m, 6H), 2.00-2.16 (m, 2H), 2.17-2.21 (s, 3H), 2.93-3.11 (m, 1H), 3.42-3.58 (s, 2H), 5.41-5.46 (s, 1H), 7.20-7.28 (m, 2H) 7.29-7.37 (m, 2H); ES-MS m/z 241.9 (MH+); HPLC RT (min) 1.69.
62%	In toluene; for 16h;Heating / reflux;	A solution of (2-methylphenyl) hydrazine hydrochloride (2.00 g, 14.6 MMOL) and crude 3- cyclopentyl-3-oxopropanenitrile from the previous step (2.32 g,-14. 6 MMOL) in toluene (6 mL) was heated to reflux for 16 h. Removal of the solvent under reduced pressure provided a residue which was purified by silica gel chromatography using hexane/EtOAc (3: 1, v/v) as the eluent. Concentration under reduced pressure provided 3-cyclopentyl-1- (2-METHYLPHENYL)-1H-PYRAZOL-5-AMINE as a light orange solid (2.19 g, 62%). ES-MS M/Z 241.9 (MH+) ; HPLC RT (min) 1. 69. AH NMR (400 MHz, CDC13) 8 1.58-1. 82 (m, 6H), 2.00- 2.16 (m, 2H), 2.17-2. 21 (s, 3H), 2.93-3. 11 (m, 1H), 3.42-3. 58 (s, 2H), 5.41-5. 46 (S, 1H), 7.20-7. 28 (m, 2H) 7.29-7. 37 (m, 2H).

Reference： [1]Patent: US2005/192294,2005,A1 .Location in patent: Page/Page column 13
[2]Patent: WO2004/50650,2004,A1 .Location in patent: Page 26

20
[ 4513-77-3 ]
[ 635-26-7 ]
[ 705278-85-9 ]

Yield	Reaction Conditions	Operation in experiment
70%	In ethanol; at 60℃; for 16h;	To a solution of (2-methylphenyl) hydrazine hydrochloride (464 mg, 2.92 mmol) in ethanol (2 mL) was added <strong>[4513-77-3]2-oxocyclohexanecarbonitrile</strong> (300 mg, 2.44 MMOL), and the mixture was heated to 60C and stirred for 16 h. The flask was then cooled to rt and the solvent was evaporated to give a solid. The crude residue of 2-(2-methylphenyl)-4, 5,6, 7- tetrahydro-2H-indazol-3-amine hydrochloride (449 mg, 70%) was used in the next step with no further purification. ES-MS m/z 228.2 (MH+) ; HPLC RT (min) 1.22.

Reference： [1]Patent: WO2004/50650,2004,A1 .Location in patent: Page 31

21
[ 55330-46-6 ]
[ 635-26-7 ]
[ 705278-79-1 ]

Yield	Reaction Conditions	Operation in experiment
81%		To a solution of 3-AMINO-3- (4-FLUOROPHENYL) ACRYLONITRILE (600 mg, 3.70 MMOL) in 1 N HCI (6 mL) was added (2-methylphenyl) hydrazine hydrochloride (558 mg, 3.51 MMOL). The reaction was refluxed for 16 h, and then cooled to rt. The resulting mixture was basified to pH 12 by slow addition of 1 N aqueous sodium hydroxide. The precipitate was collected by filtration, and then recrystallized from EtOH/Et2O to afford the intermediate (800 mg, 81%) as a light orange SOLID.'H NMR (400 MHz, CD2CI2) 6 2.20 (s, 3H), 2.14 (br s, 2H), 5.91 (s, 1 H), 7.06 (t, 2H), 7.36 (d, 4H), 7.75 (m, 2H). This material was used without further purification.

Reference： [1]Patent: WO2004/50650,2004,A1 .Location in patent: Page 27-28

22
[ 96798-17-3 ]
[ 635-26-7 ]
[3-(2,2-dimethylpropyl)-1-(2-methylphenyl)-1H-pyrazol-5-yl]amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
61%		In a mixture of 5,5-dimethyl-3-oxohexanenitrile (1.5 g, 10.77 mmol) (step 1) and <strong>[635-26-7](2-methylphenyl)hydrazine hydrochloride</strong> (1.62, 10.24 mmol) was added aq HCl (1 N, 150 mL), and the reaction mixture was refluxed for 16 h. The resulting solution was cooled to rt, basified to pH 8 with aqueous NaOH (1 N). The precipitate was collected, and the solid was dried in a vacuum oven at 60 C. to give 1.6 g (61%) of the desired product. 1H NMR (300 MHz, CD2Cl2) delta 7.27-7.38 (m, 4H), 5.42 (s, 1H), 3.54 (br, s, 2H), 2.40 (s, 2H), 2.12 (s, 3H), 0.96 (s, 9H); ES-MS m/z 244.2 (MH+); HPLC RT (min) 1.01.

Reference： [1]Patent: US2005/192294,2005,A1 .Location in patent: Page/Page column 12-13

23
[ 55330-46-6 ]
[ 635-26-7 ]
[ 705278-79-1 ]

Yield	Reaction Conditions	Operation in experiment
81%		To a solution of 3-amino-3-(4-fluorophenyl)acrylonitrile (600 mg, 3.70 mmol) in 1 N HCl (6 mL) was added <strong>[635-26-7](2-methylphenyl)hydrazine hydrochloride</strong> (558 mg, 3.51 mmol). The reaction was allowed to reflux for 16 h, and then cooled to rt. The resulting mixture was basified to pH 12 by slow addition of 1 N aqueous sodium hydroxide. The precipitate was collected by filtration, and then recrystallized from EtOH/Et2O to afford the intermediate (800 mg, 81%) as a light orange solid. 1H NMR (400 MHz, CD2Cl2) delta 2.20 (s, 3H), 2.14 (br s, 2H), 5.91 (s, 1H), 7.06 (t, 2H), 7.36 (d, 4H), 7.75 (m, 2H). This material was used without further purification.

Reference： [1]Patent: US2005/192294,2005,A1 .Location in patent: Page/Page column 14

24
[ 635-26-7 ]
[ 5417-82-3 ]
[ 870189-32-5 ]

Yield	Reaction Conditions	Operation in experiment
82%	With triethylamine; In ethanol;Heating / reflux;	1-Ethoxymethylenemalonitrile (3.76 g, 27.09 mmol) was carefully added to a solution of 2- methylphenylhydrazine hydrochloride (4.43 g, 27.09 mmol) and triethylamine (3.93 mL, 27.09 mmol) in ethanol (25 mL). The mixture was then refluxed overnight and cooled to room temperature. The resulting suspension was taken up in dichloromethane and washed with water, dried over anhydrous sodium sulfate, and concentrated. The residue was taken up in hexanes and the suspension was filtered and the orange solid dried (4.72 g, 82%). ES-MS m/z 213.2 (MH+) ; HPLC RT (min) 2.16.

Reference： [1]Patent: WO2005/112923,2005,A2 .Location in patent: Page/Page column 40

25
2-cyano-3-methylthio-3-(4-tolyl)acrylamide [ No CAS ]
[ 635-26-7 ]
[ 198967-87-2 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide;SiO2; In hexane; ethyl acetate;	EXAMPLE 17 5-Amino-1-(2-tolyl)-3-(4-tolyl)pyrazole-4-carboxamide The title compound was prepared from 2-cyano-3-methylthio-3-(4-tolyl) acrylamide (464 mg, 2.0 mmol), 2-tolylhydrazine hydrochloride (350 mg, 2.2 mmol) and sodium hydroxide (88 mg, 2.2 mmol) following the procedure used for the compound of Example 12. The crude product was subjected to column chromatography (SiO2, 75% ethyl acetate in hexane) to give the title compound as a yellow solid (30 mg) m.p. 133-135. deltaH (CDCl3) 7.52 (2H, d, J 8.1 Hz), 7.38 (4H, m), 7.28 (2H, d, J 7.4 Hz), 5.40 (4H, m), 2.40 (3H, s) and 2.23 (3H, s).

Reference： [1]Patent: US5922741,1999,A

26
[ 635-26-7 ]
[ 2094-72-6 ]
[ 912963-26-9 ]

Yield	Reaction Conditions	Operation in experiment
77%	With triethylamine; In tetrahydrofuran; at 20℃; for 2h;	Example 1 A^-(2-methylphenyl)adamantane- 1 -carbohydrazide; To an oven-dried, 25-mL, round-bottomed flask containing a magnetic stir bar was added the hydrochloride salt of o-tolylhydrazine (174 mg, 1.10 mmol). The flask was sealed with a septum and purged with nitrogen atmosphere. Anhydrous tetrahydrofuran (9 niL) was added via syringe to form a white slurry. Triethylamine (419 muL, 3.00 mmol) was added via syringe. A solution of 1-chlorocarbonyl adamantane (199 mg, 1.00 mmol) in anhydrous tetrahydrofuran (1 niL) was added. The white slurry was stirred at room temperature for 2 hours and then monitored by LC-MS (Hewlett-Packard 1100 HPLC with a Finnigan EPO <DP n="22"/>Navigator MS; C18 reverse phase column; 10-100% acetonitrile:10 mM ammonium acetate gradient; APCI positivie ionization) Water (10 mL) was added to quench and the reaction mixture was transferred to a separatory funnel. The mixture was extracted with dichloromethane (3 x 8 mL). The combined organic extracts were dried over magnesium sulfate, filtered, and concentrated by rotary evaporator to give an off-white solid. The product was re-crystallized from ethyl acetate/hexanes to give 220 mg (77%) of a white powder. MS (ESI+) m/z 285.1 (M+H)+; 1HNMR (CDCl3) delta 1.72-1.81 (m, 6H), 1.95-1.96 (m, 6H), 2.09 (br s, 3H), 2.26 (s, 3H), 3.60 (br s, IH), 6.78-6.86 (m, 2H), 7.06-7.13 (m, 2H), 7.38 (br s, IH). Anal. Calc'd for C18H24N2O: C, 76.02; H, 8.51; N, 9.85. Found: C, 75.72; H, 8.73; N, 9.75.

Reference： [1]Patent: WO2006/110516,2006,A1 .Location in patent: Page/Page column 20
[2]Journal of Medicinal Chemistry,2008,vol. 51,p. 3030 - 3034

27
[ 635-26-7 ]
[ 107-92-6 ]
[ 912963-29-2 ]

Yield	Reaction Conditions	Operation in experiment
	With benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; In ISOPROPYLAMIDE; at 100℃; for 0.116667h;Microwave irradiation;	Example 57V-(2-methylphenyl)butanohydrazide; A vial containing a stir bar was charged polymer-supported-carbodiimide resin (3.00 equivalents). To the vessel was added the butyric acid (1.25 equivalents), hydroxybenzotriazole (1.00 equivalent) and a solution of diisopropylethylamine (3.00 equivalents) with the hydrochloride salt of o-tolylhydrazine (1.00 equivalent) in dimethylacetamide. The reaction vessel was sealed and heated at 1000C for 420 seconds in a microwave reactor. After cooling, the reaction mixture was transferred to a prepacked column of Si-Carbonate (>4 equivalents of functionalized reagent), which had been previously conditioned with methanol. The reaction products were collected and concentrated to dryness. The residues were dissolved in 1:1 dimethylsulfoxide: methanol and purified by reverse phase HPLC (Waters Symmetry C8 column using a gradient of 10% to 100% acetonitrile:10 mM ammonium acetate) to afford the title compound. MS (ESI+) m/z 192.9 (M+H)+; 1HNMR (DMSO-d6/D2O) delta 0.92 (t, J = 7.5 Hz, 3H), 1.55-1.63 (m, 2H), 2.15 (s, 3H), 2.18 (t, J = 7.3 Hz, 2H), 6.64 (d, J = 8.1 H, IH), 6.69 (dd, J = 6.9, 6.9 Hz, IH), 7.01-7.04 (m, 2H).

Reference： [1]Patent: WO2006/110516,2006,A1 .Location in patent: Page/Page column 23

28
[ 635-26-7 ]
[ 40594-34-1 ]
dimethyl-(8-methyl-1,2,3,4-tetrahydro-carbazol-3-yl)-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		EXAMPLE 7 3-(Dimethylamino)-8-methyl-1,2,3,4-tetrahydrocarbazole Following the procedure given in Example 3 and using 10 g. of <strong>[40594-34-1]4-dimethylaminocyclohexanone</strong> and 11.2 g. of o-tolylhydrazine hydrochloride there was obtained 4.7 g. of 3-(dimethylamino)-8-methyl-1,2,3,4-tetrahydrocarbazole in the form of its hydrochloride which melted at 285-287C. (corr.). Test procedure 7: active at 4.8 +- 1.4 mg./kg.

Reference： [1]Patent: US3959309,1976,A

29
[ 797793-21-6 ]
[ 635-26-7 ]
6-(4-aminobenzyl)-2-(2-methylphenyl)-4,5-dihydro-3(2H)-pyridazinone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		EXAMPLE 7 6-(4-aminobenzyl)-2-(2-methylphenyl)-4,5-dihydro-3(2H)-pyridazinone To a solution of 5-(4-aminophenyl)-4-oxopentanoic acid (151 mg) in acetic acid (5 mL) were added <strong>[635-26-7]o-tolylhydrazine hydrochloride</strong> (98 mg) and sodium acetate (152 mg), and the mixture was stirred for 30 minutes at 110 degrees. The reaction mixture was concentrated and then added ethyl acetate and a saturated aqueous solution of sodium bicarbonate. The organic layer was dried over anhydrous sodium sulfate and concentrated to give the crude compound of the present invention (107 mg) having the following physical data. TLC: Rf 0.57 (ethyl acetate); NMR(CDCl3): delta 1.35 (s, 9H), 2.22 (s, 3H), 2.36 (s, 3H), 2.48 (m, 4H), 3.62 (s, 2H), 6.35 (s, 1H), 6.46 (s, 1H), 6.97 (s, 1H), 7.25 (m, 12H).

Reference： [1]Patent: US2007/10529,2007,A1 .Location in patent: Page/Page column 33

30
[ 928264-50-0 ]
[ 635-26-7 ]
[ 928264-51-1 ]

Yield	Reaction Conditions	Operation in experiment
15%		Step 2: Preparation of 3-(2-ethylpyridin-4-yl)-l-(2-methylphenyl)-lH-pyrazetaol-5-amine; A solution of <strong>[635-26-7](2-methylphenyl)hydrazine hydrochloride</strong> (1040 mg, 6.6 mol), tert- butyl 2-cyano-3-(2-ethylpyridin-4-yl)-3-oxopropanoate (1500 mg, 5.5 mmol) and para- toluenesulfonic acid (5200mg, 27 mmol) in 2-ethoxyethanol (50 mL) was stirred at 140c for 18h. The Reacion mixture was neutralized with a saturated solution of sodium bicarbonate and extracte wit ethyl acetate. The combined organic extracts were washed with brine dired over Na2SO4 and evaporated. The product was puriefied by column chromatography utilizing a gradient of ethyl acetate in hexanes. (233 mg, 15%). 1H NMR (400 MHz, CDCl3) 8.45 (d, 1 H), 7.58 (s, 1 H), 7.48 (d, 1 H), 7.38 (m, 2 H), 7.32 (m, 2 H), 5.96 (s, 1 H), 5.25 (s, 2 H), 2.75 (q., 2H), 2.10 (s, 3 H), 1.25 (t, 3H);MS (ES") m/z 279.3 (M-H+), HPLC RT (min) 0.94 {method (F) }.

Reference： [1]Patent: WO2007/27842,2007,A1 .Location in patent: Page/Page column 132

31
[ 1460-16-8 ]
[ 635-26-7 ]
[ 912963-80-5 ]

Reference： [1]Journal of Medicinal Chemistry,2008,vol. 51,p. 3030 - 3034

32
[ 635-26-7 ]
[ 762-21-0 ]
[ 87499-04-5 ]

Yield	Reaction Conditions	Operation in experiment
66%	With potassium carbonate; In ethanol; at 90℃; for 16h;	Reference Example 194 Ethyl 5-hydroxy-1-(2-methylphenyl)-1H-pyrazole-3-carboxylate A mixture of <strong>[635-26-7]2-methylphenylhydrazine hydrochloride</strong> (25.3 g), diethyl but-2-ynedioate (27.2 g) and potassium carbonate (44.26 g) was stirred in ethanol (300 mL) at 90 C. for 16 hr. The reaction mixture was allowed to cool to room temperature, acidified with 6 mol/L hydrochloric acid, and concentrated under reduced pressure. Water was added to the residue, and the mixture was extracted with ethyl acetate. The extract was washed successively with saturated aqueous sodium hydrogen carbonate solution, water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was washed with ethyl acetate-diisopropyl ether to give the title compound as an orange solid (25.8 g, yield 66%). 1H-NMR (DMSO-d6) delta: 1.27 (3H, t, J=7.2 Hz), 2.07 (3H, s), 4.24 (2H, q, J=7.2 Hz), 5.91 (1H, s), 7.26-7.43 (4H, m), 11.64 (1H, brs).

Reference： [1]Patent: US2009/156642,2009,A1 .Location in patent: Page/Page column 68

33
[ 635-26-7 ]
[ 6946-05-0 ]
[ 3449-50-1 ]

Reference： [1]Synthetic Communications,2009,vol. 39,p. 1120 - 1127

34
[ 109066-11-7 ]
[ 635-26-7 ]
C₁₂H₁₅NO [ No CAS ]

Reference： [1]Organic Letters,2009,vol. 11,p. 3458 - 3461
[2]Tetrahedron,2010,vol. 66,p. 4687 - 4695

35
[ 635-26-7 ]
3-methyl-1-tosylpyrrolidin-2-ol [ No CAS ]
C₁₉H₂₂N₂O₂S [ No CAS ]

Reference： [1]Organic Letters,2009,vol. 11,p. 3458 - 3461
[2]Tetrahedron,2010,vol. 66,p. 4687 - 4695

36
[ 33561-24-9 ]
[ 635-26-7 ]
[ 1210047-35-0 ]

Yield	Reaction Conditions	Operation in experiment
90%		5.00 g (31.5 mmol) of <strong>[635-26-7](2-methylphenyl)hydrazine hydrochloride</strong> was taken up in 30 ml of IN hydrochloric acid and 4.55 g (33.4 mmol) of 3-amino-4,4,4-trifluorobut-2-enonitrile [synthesis similar to Krespan, J. Org. Chem. 1969, 34, 42] was added. It was stirred overnight at the reflux temperature, and was then alkalized with IN sodium hydroxide solution. After extraction with ethyl acetate (2 x 200 ml), the organic phases were combined and dried over magnesium sulfate. The volatile components were removed in a rotary evaporator and the resultant oil was dried under high vacuum. This gave 6.85 g (90% of theor.) of the target compound.LC-MS (method 4): Rt = 1.08 min; MS (EIpos): m/z = 242 [M]+. 1H-NMR (400 MHz, DMSO-D6): delta [ppm] = 2.03 (s, 3H), 5.47 (sbr, 2H), 5.72 (s, IH), 7.30 (d, IH), 7.35 (dt, IH), 7.39-7.48 (m, 2H).

Reference： [1]Patent: WO2010/20363,2010,A1 .Location in patent: Page/Page column 60-61

37
[ 635-26-7 ]
[ 589-92-4 ]
[ 79242-94-7 ]

Yield	Reaction Conditions	Operation in experiment
91%	With acetic acid; for 8h;Reflux;	General procedure: A substituted phenyl hydrazine. HCl (4.61 mmol) was added to the mixture of cyclohexanone (4.61 mmol) and acetic acid (15 ml) portion wise for 30 min. The mixture was then refluxed for 8 h and progress of reaction was monitored by thin layer chromatography. The reaction mixture was cooled and poured into crushed ice. The solid product was separated, filtered, dried and recrystallized from the methanol solvent.

Reference： [1]Tetrahedron Letters,2018,vol. 59,p. 2145 - 2149
[2]Journal of Heterocyclic Chemistry,2010,vol. 47,p. 807 - 824

38
[ 1253194-10-3 ]
[ 635-26-7 ]
[ 1342235-13-5 ]

Yield	Reaction Conditions	Operation in experiment
83.3%	In ethanol; at 40 - 50℃; for 0.25h;Inert atmosphere;	General procedure: To a solution of 6-(3-dimethylamino-2-phenyl-acrolyl)-4H-benzo-[1,4]-oxazin-3-one (0.00065 mol) in ethanol, substituted phenylhydrazine hydrochloride (0.00071 mol) in ethanol was added slowly. After completion of addition, the mixture was heated to 40-50 C in a water bath. After 15 min, the solution became clear and solid was precipitated out. The solid separated was filtered, washed with ethanol and dried to give the expected product.

Reference： [1]European Journal of Medicinal Chemistry,2011,vol. 46,p. 4887 - 4896

39
N-(1-ethoxyethylidene)benzamide [ No CAS ]
[ 635-26-7 ]
[ 1364890-93-6 ]

Yield	Reaction Conditions	Operation in experiment
84%	With triethylamine; In tetrachloromethane; water;	Step 2: Synthesis of 3-Methyl-1-(2-methylphenyl)-5-phenyl-1H-1,2,4-triazole (abbreviation: HMptz1-mp) Next, into a 300-mL recovery flask were put 8.68 g of ortho-tolyl hydrazine hydrochloride, 100 mL of carbon tetrachloride, and 35 mL of Et3N, and the mixture was stirred at room temperature for 1 hour. After a predetermined time elapsed, 8.72 g of N-(1-ethoxyethylidene)benzamide obtained in the above Step 1 was added to this mixture, and the mixture was stirred at room temperature for 24 hours. After a predetermined time elapsed, water was added to the reaction mixture, and organic substances were extracted from the aqueous layer with chloroform. The organic layer of the resulting mixture was washed with saturated brine, and dried with anhydrous magnesium sulfate added thereto. The obtained mixture was gravity-filtered, and the filtrate was concentrated to give an oily substance. The obtained oily substance was purified by silica gel column chromatography. Dichloromethane was used as a developing solvent. The obtained fraction was concentrated to give 3-methyl-1-(2-methylphenyl)-5-phenyl-1H-1,2,4-triazole (abbreviation: HMptz1-mp) (an orange oily substance, 84% yield). A synthesis scheme of Step 2 is shown in the following (e-2).
84%	With triethylamine; In tetrachloromethane; water;	Step 2: Synthesis of 3-Methyl-1-(2-methylphenyl)-5-phenyl-1H-1,2,4-triazole (abbreviation: HMptz1-mp) Next, 8.68 g of o-tolyl hydrazine hydrochloride, 100 mL of carbon tetrachloride, and 35 mL of triethylamine (Et3N) were put into a 300 mL recovery flask, and the mixture was stirred at room temperature for one hour. After a predetermined time elapsed, 8.72 g of N-(1-ethoxyethylidene)benzamide obtained in the above Step 1 was added to this mixture, and the mixture was stirred at room temperature for 24 hours. After a predetermined time elapsed, water was added to the reaction mixture, the aqueous layer was subjected to extraction with chloroform, and an organic layer was obtained. The organic layer was washed with saturated brine, and dried with anhydrous magnesium sulfate added thereto. The obtained mixture was gravity-filtered, and the filtrate was concentrated to give an oily substance. The given oily substance was purified by silica gel column chromatography. Dichloromethane was used as a developing solvent. The obtained fraction was concentrated to give 3-methyl-1-(2-methylphenyl)-5-phenyl-1H-1,2,4-triazole (abbreviation: HMptz1-mp) (an orange oily substance, 84% yield). A synthetic scheme of Step 2 is shown in (b-2) below.

Reference： [1]Patent: US2012/25697,2012,A1
[2]Patent: US9059411,2015,B2 .Location in patent: Page/Page column

40
[ 943994-23-8 ]
[ 635-26-7 ]
6-[1-(2-methylphenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl]-2H-1,4-benzoxazin-3(4H)-one [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 8616 - 8631

41
[ 635-26-7 ]
[ 87277-54-1 ]
[ 1364890-93-6 ]

Yield	Reaction Conditions	Operation in experiment
84%		[Step 2: Synthesis of 3-Methyl-l-(2-methylphenyl)-5-phenyl-lH-l,2,4-triazole (abbreviation: HMptzl-mp)]Next, into a 300-mL recovery flask were put 8.68 g of ori io-tolyl hydrazine hydrochloride, 100 mL of carbon tetrachloride, and 35 mL of Et3N, and the mixture was stirred at room temperature for 1 hour. After a predetermined time elapsed, 8.72 g of N-(l-ethoxyethylidene)benzamide obtained in the above Step 1 was added to this mixture, and the mixture was stirred at room temperature for 24 hours. After a predetermined time elapsed, water was added to the reaction mixture, and organic substances were extracted from the aqueous layer with chloroform. The organic layer of the resulting mixture was washed with saturated brine, and dried with anhydrous magnesium sulfate added thereto. The obtained mixture was gravity-filtered, and the filtrate was concentrated to give an oily substance. The obtained oily substance was purified by silica gel column chromatography. Dichloromethane was used as a developing solvent. The obtained fraction was concentrated to give 3-methyl- 1 -(2-methylphenyl)-5-phenyl-lH- 1 ,2,4-triazole (abbreviation: HMptz 1 -mp) (an orange oily substance, 84 % yield). A synthesis scheme of Step 2 is shown in the following (e-2).
84%		[Step 2: Synthesis of 3-Methyl-l -(2-methylphenyl)-5-phenyl-lH-l ,2,4-triazole (abbreviation: HMptzl -mp)]Next, 8.68 g of o-tolyl hydrazine hydrochloride, 100 mL of carbon tetrachloride, and 35 mL of triethylamine (Et3N) were put into a 300-mL recovery flask and stirred at room temperature for 1 hour. After a predetermined time elapsed, 8.72 g of jV-(l -ethoxyethylidene)benzamide obtained in Step 1 above was added to this mixture, and the mixture was stirred at room temperature for 24 hours. After a predetermined time elapsed, water was added to the reaction mixture, the aqueous layer was subjected to extraction with chloroform, and an organic layer was obtained. The organic layer was washed with saturated saline, and dried with anhydrous magnesium sulfate added thereto. The obtained mixture was gravity-filtered, and the filtrate was concentrated to give an oily substance. The given oily substance was purified by silica gel column chromatography. Dichloromethane was used as a developing solvent. The obtained fraction was concentrated to give3-methyl-l -(2-methylphenyl)-5-phenyl-lH-l ,2,4-triazole (abbreviation: HMptzl -mp) (an orange oily substance, 84 % yield). The synthesis scheme of Step 2 is shown in (a-2)
84%		Step 2: Synthesis of 3-Methyl-1-(2-methylphenyl)-5-phenyl-1H-1,2,4-triazole (abbreviation: HMptzl-mp) Next, into a 300-mL recovery flask were put 8.68 g of o-tolyl hydrazine hydrochloride, 100 mL of carbon tetrachloride, and 35 mL of triethylamine (Et3N), and the mixture was stirred at room temperature for 1 hour. After a predetermined time elapsed, 8.72 g of N-(1-ethoxyethylidene)benzamide obtained in the above Step 1 was added to this mixture, and the mixture was stirred at room temperature for 24 hours. After a predetermined time elapsed, water was added to the reaction mixture, and the aqueous layer was subjected to extraction with chloroform. The organic layer of the resulting mixture was washed with saturated brine, and dried with anhydrous magnesium sulfate added thereto. The obtained mixture was gravity-filtered, and the filtrate was concentrated to give an oily substance. The obtained oily substance was purified by silica gel column chromatography. Dichloromethane was used as a developing solvent. The obtained fraction was concentrated to give 3-methyl-1-(2-methylphenyl)-5-phenyl-1H-1,2,4-triazole (abbreviation: HMptzl-mp) (an orange oily substance, 84% yield). A synthesis scheme of Step 2 is shown below.

84%		Step 2: Synthesis of 3-Methyl-1-(2-methylphenyl)-5-phenyl-1H-1,2,4-triazole (abbreviation: HMptz1-mp)[0705]Next, in a 300 mL recovery flask were put 8.68 g of o-tolyl hydrazine hydrochloride, 100 mL of carbon tetrachloride, and 35 mL of triethylamine (Et3N), and the mixture was stirred at room temperature for 1 hour. After a predetermined time elapsed, 8.72 g of N-(1-ethoxyethylidene)benzamide obtained in Step 1 was added to this mixture, and the mixture was stirred at room temperature for 24 hours. After a predetermined time elapsed, water was added to the reaction mixture, and the aqueous layer was subjected to extraction with chloroform. The organic layer was washed with saturated saline, and dried with anhydrous magnesium sulfate added thereto. The obtained mixture was gravity-filtered, and the filtrate was concentrated to give an oily substance. The obtained oily substance was purified by silica gel column chromatography. Dichloromethane was used as a developing solvent. The obtained fraction was concentrated to give 3-methyl-1-(2-methylphenyl)-5-phenyl-1H-1,2,4-triazole (abbreviation: HMptz1-mp) (orange oily substance, yield of 84%). A synthesis scheme of Step 2 is shown in (N-2).
84%		Next, 8.68 g of o-tolyl hydrazine hydrochloride, 100 mL of carbon tetrachloride, and 35 mL of triethylamine (Et3N) were put in a 300 mL recovery flask, and the mixture was stirred at room temperature for 1 hour. After a predetermined time elapsed, 8.72 g of N-(1-ethoxyethylidene)benzamide obtained in the Step 1 was added to this mixture, and the mixture was stirred at room temperature for 24 hours. After a predetermined time elapsed, water was added to the reaction mixture, and the aqueous layer was subjected to extraction with chloroform. The organic layer was washed with saturated saline, and dried with anhydrous magnesium sulfate added thereto. The obtained mixture was gravity-filtered, and the filtrate was concentrated to give an oily substance. The given oily substance was purified by silica gel column chromatography. As a developing solvent, dichloromethane was used. The obtained fraction was concentrated to give 3-methyl-1-(2-methylphenyl)-5-phenyl-1H-1,2,4-triazole (abbreviation: HMptzl-mp) (orange oily substance, yield of 84%). A scheme of the synthesis of Step 2 is shown below.
84%		Next, into a 300-mL recovery flask were put 8.68 g of <strong>[635-26-7]o-tolylhydrazine hydrochloride</strong>, 100 mL of carbon tetrachloride, and 35 mL of triethylamine (Et3N), and the mixture was stirred at room temperature for 1 hour. After a predetermined time elapsed, 8.72 g of N-(1-ethoxyethylidene)benzamide obtained in Step 1 above was added to this mixture, and the mixture was stirred at room temperature for 24 hours. After a predetermined time elapsed, water was added to the reaction mixture, and the aqueous layer was subjected to extraction with chloroform. The organic layer was washed with saturated brine, and dried with anhydrous magnesium sulfate added thereto. The obtained mixture was gravity-filtered, and the filtrate was concentrated to give an oily substance. The obtained oily substance was purified by silica gel column chromatography. Dichloromethane was used as a developing solvent. The obtained fraction was concentrated to give 3-methyl-1-(2-methylphenyl)-5-phenyl-1H-1,2,4-triazole (abbreviation: HMptzl-mp) (an orange oily substance, 84% yield).

Reference： [1]Patent: WO2012/17842,2012,A1 .Location in patent: Page/Page column 245-246
[2]Patent: WO2012/70596,2012,A1 .Location in patent: Page/Page column 57-58
[3]Patent: US2012/289708,2012,A1 .Location in patent: Page/Page column 47
[4]Patent: US2013/48964,2013,A1 .Location in patent: Paragraph 0705
[5]Patent: US2013/75705,2013,A1 .Location in patent: Paragraph 366
[6]Patent: US9029558,2015,B2 .Location in patent: Page/Page column 54

42
[ 41796-03-6 ]
[ 635-26-7 ]
[ 1379581-66-4 ]

Yield	Reaction Conditions	Operation in experiment
78%		[Step 2: Synthesis of 3-Isopropyl-l-(2-methylphenyl)-5-phenyl-lH-l ,2,4-triazole] (abbreviation: HiPrptzl-mp)]Next, 4.64 g of o-tolyl hydrazine hydrochloride, 50 mL of carbon tetrachloride, and 20 mL of triethylamine (Et3N) were put into a 300-mL three-neck flask and stirred at room temperature for 1 hour. After a predetermined time elapsed, 6.0 g of N-(l-methoxyisobutylidene)benzamide obtained in Step 1 above was added to this mixture, and the mixture was stirred at room temperature for 17 hours. After a predetermined time elapsed, water was added to the reaction mixture, the aqueous layer was subjected to extraction with chloroform, and an organic layer was obtained. The organic layer and the solution of the extract were washed together with saturated saline, and anhydrate magnesium sulfate was added to the organic layer for drying. The mixture was gravity-filtered and the filtrate was concentrated to give an oily substance. This oily substance was purified by silica gel column chromatography. As the developing solvent, hexane and ethyl acetate in a ratio of 10: 1 (v/v) was used. The obtained fraction was concentrated to give3-isopropyl-l-(2-methylphenyl)-5-phenyl-lH-l ,2,4-triazole (abbreviation: HiPrptzl-mp) (an orange oily substance, 78 % yield). The synthesis scheme of Step 2 is shown in (b-2) below.

Reference： [1]Patent: WO2012/70596,2012,A1 .Location in patent: Page/Page column 61-62

43
[ 635-26-7 ]
N-(1-ethoxybutylidene)benzamide [ No CAS ]
[ 1379581-68-6 ]

Yield	Reaction Conditions	Operation in experiment
74%		[Step 2: Synthesis of l-(2-Methylphenyl)-5-phenyl-3-propyl-lH-l,2,4-triazole (abbreviation: HPrptzl-mp)]Next, 4.3 g of o-tolyl hydrazine hydrochloride and 50 mL of carbon tetrachloride were put into a 200-mL three-neck flask, and 20 mL of triethylamine (Et3N) was added dropwise to this mixture little by little. After the addition, the mixture was stirred at room temperature for 1 hour. To this mixture was added 5.0 g of N-(l -ethoxybutylidene)benzamide, and the mixture was stirred at room temperature for 18 hours. Water was added to the obtained reaction mixture, the aqueous layer was subjected to extraction with chloroform, and an organic layer was obtained. The organic layer was washed with saturated saline, and dried with anhydrous magnesium sulfate added thereto. The resulting mixture was gravity-filtered to give filtrate. This filtrate was concentrated to give l-(2-methylphenyl)-5-phenyl-3-propyl-lH-l ,2,4-triazole (abbreviation: HPrptzl -mp) (a red oily substance, 74 % yield). The synthesis scheme of Step 1 is shown in (c-2) below.

Reference： [1]Patent: WO2012/70596,2012,A1 .Location in patent: Page/Page column 65-66

44
[ 1379581-69-7 ]
[ 635-26-7 ]
[ 1379581-70-0 ]

Yield	Reaction Conditions	Operation in experiment
55%		[0244][Step 2: Synthesis of 3-Ethyl-l-(2-methylphenyl)-5-phenyl-lH-l ,2,4-triazole (abbreviation: HEptz 1 -mp)]Next, 5.8 g of o-tolyl hydrazine hydrochloride, 100 mL of carbon tetrachloride, and 11 mL of triethylamine (Et3N) were put into a 300-mL three-neck flask, and the mixture was stirred at room temperature for 1 hour. After a predetermined time elapsed, 6.3 g of N-( 1 -methoxypropylidene)benzamide obtained in Step 1 above was added to this mixture, and the mixture was stirred at room temperature for 65 hours. Water was added to the obtained reaction solution, the aqueous layer was subjected to extraction with chloroform, and an organic layer was obtained. The organic layer and the obtained solution of the extract were washed together with saturated saline, and anhydrous magnesium sulfate was added to the organic layer for drying. The obtained mixture was gravity-filtered, and the filtrate was concentrated to give an oily substance. The given oily substance was purified by silica gel column chromatography. Dichloromethane was used as a developing solvent. The obtained fraction was concentrated to give 3-ethyl-l -(2-methylphenyl)-5-phenyl-lH-l ,2,4-triazole (abbreviation: HEptzl-mp) (a brown oily substance, 55 % yield). The synthesis scheme of Step 2 is shown in (g-2) below.

Reference： [1]Patent: WO2012/70596,2012,A1 .Location in patent: Page/Page column 69-70

45
[ 1379581-73-3 ]
[ 635-26-7 ]
[ 1379581-74-4 ]

Yield	Reaction Conditions	Operation in experiment
59%	With triethylamine; In tetrachloromethane; at 20℃; for 20h;	[Step 2: Synthesis of l-(2-Methylphenyl)-3-methyl-5-(2-naphthyl)-lH-l ,2,4-triazole (abbreviation: HMntzl-mp)]Next, 6.4 g of o-tolyl hydrazine hydrochloride and 150 mL of carbon tetrachloride were put into a 300-mL three-neck flask, a mixed solvent of 8.8 g of N-( 1 -ethoxyethylidene)-2-naphthamide obtained in Step 1 above and 20 mL of carbon tetrachloride were added dropwise to this mixture, and the mixture was stirred at room temperature for 20 hours. After the reaction, water was added to this reaction solution, the aqueous layer was subjected to extraction with chloroform, and an organic layer was obtained. The obtained solution of the extract and the organic layer were washed together with saturated saline, and anhydrate magnesium sulfate was added for drying. The obtained mixture was gravity -filtered and the filtrate was concentrated to give an oily substance. The given oily substance was purified by flash column chromatography. As the developing solvent, a mixed solvent of dichloromethane and hexane in a ratio of 1 : 1 (v/v) was used. The obtained fraction was concentrated to give an oily substance. This oily substance was further purified by silica gel column chromatography. Dichloromethane was used as a developing solvent. The obtained fraction was concentrated to give l -(2-methylphenyl)-3-methyl-5-(2-naphthyl)-lH-l ,2,4-triazole (abbreviation: HMntzl -mp) (a brown solid, 59 % yield). The synthesis scheme of Step 2 is shown in (j-2) below.

Reference： [1]Patent: WO2012/70596,2012,A1 .Location in patent: Page/Page column 77-78

46
[ 41876-75-9 ]
[ 635-26-7 ]
1-(2-methylphenyl)-5-phenyl-1H-1,2,4-triazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
57%		[Step 2: Synthesis of l-(2-Methylphenyl)-5-phenyl-lH-l,2,4-triazole (abbreviation: Hptzl-mp)]Next, 10.8 g of -tolyl hydrazine hydrochloride and 50 niL of dioxane were put into a 500-mL three-neck flask, 14 mL of an aqueous solution of sodium hydroxide (5 mol/L) was added dropwise to this mixture, and the mixture was stirred at room temperature for 15 minutes. After a predetermined time elapsed, 100 mL of 70 % acetic acid aqueous solution and 10.0 g of N-[(dimethylamino)methylidene]benzamide obtained in Step 1 above were added to this mixture, and the mixture was heated and stirred at 90 C for 2.5 hours. The obtained reaction solution was poured into 200 mL of water and the mixture was stirred at room temperature to precipitate a solid. This mixture was suction-filtered and the solid was washed with water. The obtained solid was recrystallized from a mixed solvent of ethanol and hexane, so that l-(2-methylphenyl)-5-phenyl-lH-l ,2,4-triazole (abbreviation: Hptzl-mp) was obtained (a white solid, 57 % yield). The synthesis scheme of Step 2 is shown in (d-2) below.

Reference： [1]Patent: WO2012/70596,2012,A1 .Location in patent: Page/Page column 102

47
[ 15679-03-5 ]
[ 635-26-7 ]
[ 1145788-00-6 ]

Yield	Reaction Conditions	Operation in experiment
85%	In ethanol; for 16h;Inert atmosphere; Reflux;	N-Phenanthridin-6-yl-N'-<strong>[635-26-7]o-tolylhydrazine hydrochloride</strong> A solution of <strong>[635-26-7]o-tolylhydrazine hydrochloride</strong> (7.6 g, 47 mmol) in dichloromethane (450 ml) is extracted by shaking three times each with saturated aqueous sodium hydrogencarbonate solution (90 ml each time) and demineralized water. The organic phase is dried over sodium sulfate, filtered and concentrated to dryness. Yield: 4.9 g (86%). The hydrazine (4.8 g, 39 mmol) is dissolved in ethanol (100 ml) and admixed under argon with 6-chlorophenanthridine (A. G. Mikhailovskii, V. S. Shklyaev, Chem. Heterocycl. Comp. 1992, 445) (7.0 g, 33 mmol). The mixture is stirred under reflux for 16 h. After cooling to room temperature, the resulting precipitate is filtered off and washed with ethanol and petroleum ether. Yield: 9.3 g (85%). 1H NMR (d6-DMSO, 400 MHz): delta=2.41 (s, 3H), 6.90 (t, 1H), 6.97 (d, 1H), 7.11 (t, 1H), 7.20 (d, 1H), 7.60 (t, 1H), 7.74 (t, 1H), 7.92 (t, 1H), 8.16 (t, 1H), 8.24 (d, 1H), 8.30 (br s, 1H), 8.71 (d, 1H), 8.88 (d, 1H), 8.89 (d, 1H), 12.23 (br s, 1H), 13.02 (br s, 1H).

Reference： [1]Patent: US8258297,2012,B2 .Location in patent: Page/Page column 46-47

48
[ 41979-39-9 ]
[ 635-26-7 ]
[ 350680-06-7 ]

Yield	Reaction Conditions	Operation in experiment
42%	With hydrogenchloride In ethanol; water at 80℃;

Reference： [1]Dossetter, Alexander G.; Beeley, Howard; Bowyer, Jonathan; Cook, Calum R.; Crawford, James J.; Finlayson, Jonathan E.; Heron, Nicola M.; Heyes, Christine; Highton, Adrian J.; Hudson, Julian A.; Jestel, Anja; Kenny, Peter W.; Krapp, Stephan; Martin, Scott; MacFaul, Philip A.; McGuire, Thomas M.; Gutierrez, Pablo Morentin; Morley, Andrew D.; Morris, Jeffrey J.; Page, Ken M.; Ribeiro, Lyn Rosenbrier; Sawney, Helen; Steinbacher, Stefan; Smith, Caroline; Vickers, Madeleine [Journal of Medicinal Chemistry, 2012, vol. 55, # 14, p. 6363 - 6374]

49
[ 635-26-7 ]
[ 110-12-3 ]
[ 1456718-36-7 ]

Yield	Reaction Conditions	Operation in experiment
80%	With 1,3,5-trichloro-2,4,6-triazine; In ethanol; at 80℃; for 2h;	General procedure: A mixture ofphenyl hydrazines.HCl (1 mmol), ketones (1 mmol) andTCT (0.1 mmol) in distilled ethanol was heated to 80 C. After 2 h the startingmaterial was absent as monitored by TLC. The reaction mixture was cooled toambient temperature and diluted with water. The product was extracted intoethyl acetate (5x3 mL). The combined organiclayer was dried over anhydrous Na2SO4 and concentrated toresidue. Thus obtained residue was purified by column chromatography (gradientof 5-10 % EtOAc in Petroleum ether) to yield indole ortetrahydrocarbazole or tetrahydrocarboline derivatives (3a-3x).

Reference： [1]Tetrahedron Letters,2013,vol. 54,p. 5591 - 5596

50
[ 1149371-93-6 ]
[ 635-26-7 ]
C₃₀H₄₄N₂O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium acetate; In ethanol; at 78℃;	General procedure: A mixture of compound 5 (0.360 g, 1 mmol) and various phenylhydrazines 6a-6ad (0.145-0.225 g,1 mmol) in dry EtOH (10 mL) were stirred at 78C in the presence of CH3COONa (0.099 g,1.2 mmol). After completion of the reaction monitored by TLC, the solution was then poured into water (10 mL), the white precipitate was filtered and washed with water and dried. The crude product was recrystallized from ethyl acetate/light petroleum ether to give compounds 7a-7ad. Then to a solution of compounds 7a-7ad(0.450-0.529 g, 1 mmol) in toluene (5 mL), 48% BF3*OEt2 (48% solution in Et2O, 0.05 mL, 0.17 mmol) was added dropwise and the mixture was heated under a nitrogen atmosphere at 118C. After completion of the reaction monitored by TLC, water (10 mL) was added to the mixture, which was next neutralized with NaHCO3, and the organic phase was separated and dried over Na2SO4. After evaporation in vacuo, the crude product was purified by column chromatography to give product 9a-9ad.

Reference： [1]European Journal of Medicinal Chemistry,2013,vol. 65,p. 70 - 82

51
[ 955093-27-3 ]
[ 635-26-7 ]
[ 1567367-14-9 ]

Yield	Reaction Conditions	Operation in experiment
34%		General procedure: To 1.2 eq. of the corresponding phenylhydrazine hydrochloride under Ar atmosphere, 1.2 eq of aqueous 1M NaOH were added and the mixture was stirred for 10min. Then, a 0.1M solution of aldehyde 5 or ketone 16 in AcOH was added and the mixture was stirred under Ar atmosphere and at r.t. for 2h and then heated up to 130C for further 2h. In the case of the reactions with ketone 16 the mixture was stirred at r.t. for 7h and at 130C for 16h. It was let to cool down to r.t. and diluted with EtOAc. The organic layer was washed with 6% NaHCO3 and brine, dried over anhydrous Na2SO4, filtered and the solvent was removed. The crude was purified through column chromatography affording the corresponding indole derivatives.

Reference： [1]European Journal of Medicinal Chemistry,2014,vol. 73,p. 265 - 279

52
[ 955093-27-3 ]
[ 635-26-7 ]
[ 1567367-24-1 ]

Yield	Reaction Conditions	Operation in experiment
62%		General procedure: To 1.2 eq. of the corresponding phenylhydrazine hydrochloride under Ar atmosphere, 1.2 eq of aqueous 1M NaOH were added and the mixture was stirred for 10min. Then, a 0.1M solution of aldehyde 5 or ketone 16 in AcOH was added and the mixture was stirred under Ar atmosphere and at r.t. for 2h and then heated up to 130C for further 2h. In the case of the reactions with ketone 16 the mixture was stirred at r.t. for 7h and at 130C for 16h. It was let to cool down to r.t. and diluted with EtOAc. The organic layer was washed with 6% NaHCO3 and brine, dried over anhydrous Na2SO4, filtered and the solvent was removed. The crude was purified through column chromatography affording the corresponding indole derivatives.

Reference： [1]European Journal of Medicinal Chemistry,2014,vol. 73,p. 265 - 279

53
[ 1384519-04-3 ]
[ 635-26-7 ]
[ 1583273-09-9 ]

Yield	Reaction Conditions	Operation in experiment
68%	With acetic acid; In ethanol; at 20℃;Reflux;	General procedure: Compound (E)-ethyl 3-oxo-2,3-dihydrobenzo[b]oxepine-4-carboxylate (3a, 100 mg, 0.4 mmol) was dissolved in absolute ethanol (3 mL), phenylhydrazine hydrochloride (5a, 62 mg,0.4 mmol) and acetic acid (0.06 mL, 0.06 mmol) were added atroom temperature, and the resulting mixture was refluxed for 4 h.The reaction was monitored by TLC and after completion of thereaction (TLC), the reaction mixture was brought to room temperatureand solvent was removed under reduced pressure; diluted with water and extracted with ethyl acetate. The organic layer wasdried over Na2SO4, solvent was removed under reduced pressure,and the residue was purified by column chromatography usingsilica gel (hexane/ethyl acetate) provided 6a in 80% yield. Similarlyother benzoxepinopyrazolones 6b-t were prepared from corresponding3-oxo-2,3-dihydrobenzo[b]oxepine-4-carboxylates 3bed with substituted phenylhydrazine hydrochlorides 5b-k.

Reference： [1]European Journal of Medicinal Chemistry,2014,vol. 76,p. 460 - 469

54
[ 15226-74-1 ]
[ 635-26-7 ]
[ 6630-33-7 ]
2-(p-tolyl)phthalazin-1(2H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76.2%	With 1,1'-bis-(diphenylphosphino)ferrocene; palladium diacetate; 1,8-diazabicyclo[5.4.0]undec-7-ene; In N,N-dimethyl-formamide; at 90℃; for 3h;Sealed tube; Molecular sieve;	General procedure: To a stirred mixture of 2-bromobenzaldehyde (0.5 mmol) and the corresponding hydrazinehydrochloride (0.6 mmol) in DMF taken in a 25 mL sealed tube, was added Pd(OAc)2 (5 mol %), dppf (6 mol %), molecular sieves (W/W), DBU (1.25 mmol), and Co2(CO)8 (0.15 mmol). The reaction vessel was closed immediately and heated at 90 C for 3 h. The reaction mixture was cooled to room temperature, filtered through celite bed. The filtrate was diluted with water and extracted with ethyl acetate. The ethyl acetate layer was washed with water, brine solution, dried over MgSO4, evaporated in vacuum and purified using column chromatography on silica gel (60-120 mesh) to afford the pure products.

Reference： [1]Tetrahedron Letters,2014,vol. 55,p. 3482 - 3485

55
[ 1755-15-3 ]
[ 635-26-7 ]
3,6,6-trimethyl-1-(2-methylphenyl)-1,5,6,7-tetrahydro-4H-indazol-4-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
51%	With sulfuric acid; In ethanol; at 20℃; for 24h;	General procedure: To a mixture of 1-(2-bromo-4-chlorophenyl)hydrazine hydrochloride 23b (103.2 mg, 0.40 mmol) and 2-acetyl-5,5-dimethyl-1,3-cyclohexanedione (72.9 mg, 0.40 mmol) in ethanol (1.2 mL) was treated with a few drops of concd H2SO4. The mixture was stirred at room temperature for 24 h. After the reaction was finished, the mixture was diluted with EtOAc (8.0 mL) and washed with water (4.0 mL), satd NaHCO3(aq) (4.0 mL) and brine (4.0 mL). The organic layer was dried over MgSO4 and concentrated under reduced pressure. The residue was purified by Isco CombiFlash Companion column chromatography (silica gel, 0-70% EtOAc/hexane) to give 1-(2-bromo-4-chlorophenyl)-3,6,6-trimethyl-1,5,6,7-tetrahydro-4H-indazol-4-one 20 (65.0 mg, 44%) as a powder. 5.2.7 3,6,6-Trimethyl-1-(2-methylphenyl)-1,5,6,7-tetrahydro-4H-indazol-4-one (7) The reaction of <strong>[635-26-7]1-<strong>[635-26-7](2-methylphenyl)hydrazine hydrochloride</strong></strong> (63.5 mg, 0.40 mmol) with 2-acetyl-5,5-dimethyl-1,3-cyclohexanedione (72.9 mg, 0.40 mmol), by a procedure similar to that for 20, gave 3,6,6-trimethyl-1-(2-methylphenyl)-1,5,6,7-tetrahydro-4H-indazol-4-one 7 (55.0 mg, 51%) as a powder. 1H NMR (CD3OD, 400 MHz) delta 7.49-7.36 (m, 3H), 7.28 (d, J = 7.6 Hz, 1H), 2.50 (s, 2H), 2.47 (s, 3H), 2.40 (s, 2H), 2.09 (s, 3H), 1.08 (s, 6H); HRMS calcd for C17H21N2O (M+H) 269.1654, found 269.1656.

Reference： [1]Bioorganic and Medicinal Chemistry,2014,vol. 22,p. 4694 - 4703

56
[ 635-26-7 ]
[ 141-97-9 ]
[ 29211-55-0 ]

Yield	Reaction Conditions	Operation in experiment
75.3%	With acetic acid;Reflux;	General procedure: To a solution of an appropriate intermediate 9a-h (0.028 mol) and ethyl acetoacetate (0.034 mol) dissolved in acetic acid (10 mL), the reaction mixture was heated under refluxed with stirring until the starting materials could no longer be detected by TLC. The solvent was evaporated under reduced pressure and the residue was dissolved in ethyl acetate and saturated sodium bicarbonate solution, the mixture was washed with saturated sodium bicarbonate solution (20 mL 3), brine (20 mL 3) in sequence, and the organic phase was separated, dried, and evaporated. The crude product was crystallized from THF and Hexane to afford brown solids 10a-h. Yield 75.3%. mp 126-129 C. ESI-MS m/z: 188.23 [M + H]+.
75.3%	With acetic acid;Reflux;	General procedure: To a solution of an appropriate intermediate 9a-h (0.028 mol)and ethyl acetoacetate (0.034 mol) dissolved in acetic acid(10 mL), the reaction mixture was heated under refluxed with stirringuntil the starting materials could no longer be detected by TLC. The solvent was evaporated under reduced pressure and the residuewas dissolved in ethyl acetate and saturated sodium bicarbonatesolution, the mixture was washed with saturated sodiumbicarbonate solution (20 mL 3), brine (20 mL 3) in sequence, and the organic phase was separated, dried, and evaporated. Thecrude product was crystallized from THF and Hexane to affordbrown solids 10a-h.

Reference： [1]Bioorganic Chemistry,2014,vol. 57,p. 30 - 42
[2]Bioorganic Chemistry,2014,vol. 57,p. 30 - 42

57
[ 635-26-7 ]
[ 1218-69-5 ]
C₂₆H₂₀N₄O₂Pt [ No CAS ]

Reference： [1]Chemistry - An Asian Journal,2015,vol. 10,p. 2368 - 2379

58
[ 635-26-7 ]
[ 1218-69-5 ]
C₂₁H₁₇N₃O₂ [ No CAS ]

Reference： [1]Chemistry - An Asian Journal,2015,vol. 10,p. 2368 - 2379

59
[ 635-26-7 ]
[ 151121-34-5 ]
(S)-tert-butyl 2-((tert-butoxycarbonyl)amino)-3-(5-hydroxy-1-(o-tolyl)-1H-pyrazol-4-yl)propanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
57%	With hydrogenchloride; In propan-1-ol; ethyl acetate; for 8h;Reflux;	General procedure: To a solution of (S,E)-di-tert-butyl 4-((dimethylamino)methylene)-5-oxopyrrolidine-1,2-dicarboxylate (1)(1 equivalent) in nPrOH hydrazine hydrochloride 2 (1 equivalent) or hydrazine 2 (1 equivalent) and HCl(2M in EtOAc, 1 equivalent) was/were added and the resulting mixture was heated under reflux for 3-8 h.Volatile components were evaporated in vacuo and the residue was purified by column chromatography(CC) (Silica gel 60). Fractions containing the product were combined and volatile components evaporatedin vacuo to give 3.

Reference： [1]Heterocycles,2015,vol. 91,p. 2315 - 2326

60
[ 635-26-7 ]
[ 118-91-2 ]
2-chloro-N′-(o-tolyl)benzohydrazide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
50%	With 6-chloro-3-((dimethylamino)(dimethyliminio)methyl)-1H-benzo[d][1,2,3]triazol-3-ium-1-olatehexafluorophosphate(V); triethylamine; In N,N-dimethyl-formamide; at 20℃;	General procedure: To a solution of p-tolylhydrazine hydrochloride (0.79 g, 5 mmol), 2-chlorobenzoic acid (0.78 g, 5 mmol), and HCTU (2.28 g, 5.5 mmol) in DMF (10.0 mL), Et3N (2.08 mL, 15 mmol) was added. The mixture was stirred at r.t. overnight. Then the mixture was washed with sat. aq NH4Cl, aq NaHCO3, and brine. The organic layer was dried (MgSO4) and the solvent was removed under reduced pressure. The residue was purified by column chromatography (petroleum ether/EtOAc,5:1) to give 1b (0.78 g, 60%) as a white solid; mp 161.3-162.4 C.

Reference： [1]Synthesis,2016,vol. 48,p. 3551 - 3558

61
[ 203186-58-7 ]
[ 635-26-7 ]
ethyl 5-methyl-1-(o-tolyl)-1H-pyrazole-4-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine; In ethanol; at 60℃; for 3h;	To a solution of the above crude S110 (3.6 g, 19.5 mmol) in ethanol (20 mL) was added DIPEA (2.71 g, 21 mmol) and 2-metylphenyhdrazine.HCl (3.3 g, 21 mmol). The mixture was allowed to stir at 60 C for 3 h. Then, the mixture was cooled to room temperature, concentrated to give the crude product as an oil (4.3 g, 90%).

Reference： [1]Patent: WO2017/151786,2017,A1 .Location in patent: Paragraph 00231

62
[ 529-27-1 ]
[ 635-26-7 ]

Yield	Reaction Conditions	Operation in experiment
39.5%	With hydrogenchloride; at 65℃;	The pure product is dissolved in 100 g 2 - methyl phenyl hydrazine 69 ml 37% in hydrochloric acid, in the 65 C stirring to the reaction solution to crystallize, cooling to 20 C, filtering, washing the filter cake for acetone, and dried to obtain 2 - methyl phenyl hydrazine hydrochloride product 110 g, content 99.2%, yield 39.5%.

Reference： [1]Patent: CN107814750,2018,A .Location in patent: Paragraph 0026; 0027; 0035; 0036; 0046

63
[ 21321-91-5 ]
[ 635-26-7 ]
(16R,17S)-3-methoxy-3′-methyl-1′-(2″-tolyl)-2′-pyrazolino[4′,5′:17,16]estra-1,3,5(10)-triene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	With toluene-4-sulfonic acid; In ethanol; at 100℃; for 0.333333h;Microwave irradiation;	General procedure: To a solution of 13 (248 mg, 0.80 mmol) in EtOH (5 mL), PTSA monohydrate (152 mg, 0.80 mmol) and (substituted) phenylhydrazine hydrochloride (15a-j, 1.10 mmol) were added, and the mixture was irradiated in a closed vessel at 100 C for 20 min. After completion of the reaction, the mixture was poured into water (20 mL), neutralized by the addition of NaHCO3 and extracted with CH2Cl2(2 × 15 mL). The combined organic phases were dried with anhydrous Na2SO4 and concentrated in vacuo. The crude product was purified by column chromatography with hexane/CH2Cl2 = 50:50.(16R,17S)-3-Methoxy-3?-methyl-1?-phenyl-2?-pyrazolino[4?,5?:17,16]estra-1,3,5(10)-triene (17a) According to the general procedure, phenylhydrazine hydrochloride (15a, 159 mg) was used. Yield:285 mg (white solid); Mp 221-223 C; Rf = 0.58 (ss A).

Reference： [1]Molecules,2019,vol. 24

64
[ 635-26-7 ]
[ 4381-25-3 ]
rac-N-[(2-methyl)-phenyl]-S-phenyl-S-methylsulfoximine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%	With oxygen; potassium acetate; copper(I) bromide; In acetone; at 20℃; for 12h;Schlenk technique;	General procedure: Under the oxygen atmosphere, a Schlenk tube (35 mL) equipped with a magnetic bar was loaded with the NH-sulfoximine 1 (0.5 mmo), arylhydrazine chloride (2.0 equiv.), Cu(OAc)2 (20 mol%), KOAc (2.0 equiv.) in dry acetone (4.0 mL). Then the mixture was allowed to stir at room temperature for 12 h. After the completion of the reaction, as monitored by TLC analysis, the mixture was filtered through a short celite pad and washed with dichloromethane (15 mL 3). The filtrate was concentrated, and the oily crude product was puried by column chromatography using silica gel (200-300 mesh) as stationary phase and a mixture of n-hexaneand ethyl acetate (2:1) as eluent to give the corresponding arylated products 3 or 5 (Rf = ca.0.3 otherwise noted).

Reference： [1]Tetrahedron,2019,vol. 75,p. 3886 - 3893

65
[ 98-10-2 ]
[ 635-26-7 ]
[ 18457-86-8 ]

Yield	Reaction Conditions	Operation in experiment
72%	With tert.-butylhydroperoxide; copper acetylacetonate; caesium carbonate; In water; acetonitrile; at 100℃; for 12h;Schlenk technique;	General procedure: Under the air atmosphere, a Schlenk tube (35 mL) equipped with a magnetic bar was loaded with the sulfonamide 4 (0.5 mmol), Cu(acac)2 (20 mol%), TBHP (70% in water, 2.0 equiv.), Cs2CO3 (2.0equiv.) in dry solvent MeCN (4.0 mL). Then the reaction mixture was allowed to stir at 60C for 12 h. After the completion of the reaction, as monitored by TLC analysis, the mixture was filtered through a short celite pad and washed with dichloromethane (15 mL x 3). The filtrate was concentrated, and the oily crude product was puried by column chromatography using silica gel (200-300 mesh) as stationary phase and a mixture of n-hexane and ethyl acetate (2:1) as eluent to give the corresponding arylated products 5 (Rf = ca.0.3 otherwise noted).

Reference： [1]Tetrahedron,2019,vol. 75,p. 3886 - 3893

66
[ 1666-13-3 ]
[ 635-26-7 ]
[ 94800-50-7 ]

Yield	Reaction Conditions	Operation in experiment
85%	With [2,2]bipyridinyl; nickel(II) acetate tetrahydrate; nickel; sodium carbonate; In dimethyl sulfoxide; for 0.5h;Sonication; Green chemistry;	General procedure: The reaction of dipheyldiselenide (0.125 mmol) and 4-chloropheylhydrazinehydrochloride (0.25 mmol) was carried out in DMSO in presence of sodium carbonate (0.3 mmol), metal salt (0.05 mmol)and 2,2-Bipyridine ligand (0.1 mmol) in an ultrasonic bath as a modelreaction (Scheme 2).

Reference： [1]Molecular catalysis,2019,vol. 476

67
3-amino-2-(chloroacetyl)but-2-enenitrile [ No CAS ]
[ 635-26-7 ]
5-(chloromethyl)-3-methyl-1-(2-methylphenyl)-1H-pyrazole-4-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
29%	With sodium acetate; In acetonitrile; at 20℃;	General procedure: Step 2. The appropriate substituted hydrazine (1.0 eq) was added to a mixture of the compound 3 (1.0 eq), and sodium acetate in acetonitrile. The reaction mixture was stirred at room temperature overnight. 1 N HC1 was added, and the resulted mixture was extracted with ethyl acetate (x3). The combined organic layers were washed with brine (x3), dried over Na2S04, filtered and evaporated. The desired product was obtained after purification of the crude material as reported in the specific examples.

Reference： [1]Patent: WO2019/175152,2019,A1 .Location in patent: Page/Page column 36-37; 65-66

68
ethyl 2-acetylamino-5-[3-(4-fluorophenyl)-3-oxo-prop-1-ynyl]benzoate [ No CAS ]
[ 635-26-7 ]
ethyl 2-acetylamino-5-[5-(4-fluorophenyl)-1-(o-tolyl)-1H-pyrazol-3-yl]benzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
69%	With triethylamine; In ethanol; at 80℃; for 9h;	General procedure: A mixture of alkynone 1 or 2 (1 equiv), arylhydrazine 8-14(1.2 equiv), and Et3N (5 equiv) in anhydrous EtOH (50 ml)was refluxed for 9 h. The reaction mixture was evaporated,the residue was purified by silica gel column chromatography(eluent CHCl3).

Reference： [1]Chemistry of Heterocyclic Compounds,2019,vol. 55,p. 943 - 955
Khim. Geterotsikl. Soedin.,2019,vol. 55,p. 943 - 955,13

69
ethyl 2-acetylamino-5-[3-(4-methoxyphenyl)-3-oxoprop-1-ynyl]benzoate [ No CAS ]
[ 635-26-7 ]
ethyl 2-acetylamino-5-[5-(4-methoxyphenyl)-1-(o-tolyl)-1H-pyrazol-3-yl]benzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
67%	With triethylamine; In ethanol; at 80℃; for 9h;	General procedure: A mixture of alkynone 1 or 2 (1 equiv), arylhydrazine 8-14(1.2 equiv), and Et3N (5 equiv) in anhydrous EtOH (50 ml)was refluxed for 9 h. The reaction mixture was evaporated,the residue was purified by silica gel column chromatography(eluent CHCl3).

Reference： [1]Chemistry of Heterocyclic Compounds,2019,vol. 55,p. 943 - 955
Khim. Geterotsikl. Soedin.,2019,vol. 55,p. 943 - 955,13

70
[ 6479-18-1 ]
[ 635-26-7 ]
1-methyl-3-(o-tolyl)quinoxalin-2(1H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
72%	With C114H108N24O24; potassium carbonate; In dimethyl sulfoxide; for 24h;Irradiation;	in room temperature,In a 5 mL photoreaction tube, N-methylquinoxaline-2 (1H) -one (0.1 mmol), <strong>[635-26-7]2-methylphenylhydrazine hydrochloride</strong> (0.3 mmol), and 2D-COF-1 (4 mg) were sequentially added. K2CO3 (0.3 mmol) and dimethyl sulfoxide (1.5 mL). Stir in the air for 24 hours under the irradiation of a blue LED lamp with a power of 34W and a wavelength of 400-500nm. The reaction was stopped, extracted with ethyl acetate and water, and then concentrated under reduced pressure to obtain a crude product. Finally, it was washed with a mixed eluent of petroleum ether and ethyl acetate, and flash column chromatography (silica gel column) was obtained to obtain the corresponding quinoxalinone derivative (light yellow solid 18 mg, yield 72%).

Reference： [1]Patent: CN110483421,2019,A .Location in patent: Paragraph 0065-0068

71
7-fluoro-1-methyl-1,2-dihydroquinoxalin-2-one [ No CAS ]
[ 635-26-7 ]
C₁₆H₁₃FN₂O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
59%	With C114H108N24O24; potassium carbonate; In dimethyl sulfoxide; for 24h;Irradiation;	in room temperature,7-fluoro-1-methylquinoxaline-2 (1H) -one (0.1 mmol), <strong>[635-26-7]2-methylphenylhydrazine hydrochloride</strong> (0.3 mmol), 2D-COF- 1 (4 mg), K2CO3 (0.3 mmol) and dimethyl sulfoxide (1.5 mL). Stir in the air for 24 hours under the irradiation of a blue LED lamp with a power of 34W and a wavelength of 400-500nm. The reaction was stopped, extracted with ethyl acetate and water, and then concentrated under reduced pressure to obtain a crude product. Finally, it was washed with a mixed eluent of petroleum ether and ethyl acetate, and the corresponding quinoxalinone derivative was obtained by flash column chromatography (silica gel column) (light yellow solid 16 mg, yield 59%).

Reference： [1]Patent: CN110483421,2019,A .Location in patent: Paragraph 0105-0108

72
C₂₀H₂₁NO₃ [ No CAS ]
[ 635-26-7 ]
C₂₇H₂₇N₃O [ No CAS ]
C₂₇H₂₇N₃O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87%; 6%	In ethanol; at 120℃; for 1h;Microwave irradiation; Inert atmosphere;	Compound 4 (180 mg, 0.56 mmol) and <strong>[635-26-7]o-tolylhydrazine hydrochloride</strong> (180 mg, 1.13 mmol) in EtOH (4 mL) was heated in Biotage microwave at 120 C for 1 h and then cooled to room temperature. The mixture was diluted with MTBE. The mixture was washed with 1 N aq. HC1, 1 N aq. NaOH, and water. The organic extract was dried over NazSOy filtered and concentrated. Tire residue was purified by column chromatography (silica gel, eluting with 0% to 30% EtOAc in hexanes) to give compound 23a (199 mg, 87% yield) as a beige solid m/z = 410 (M+). From the column, also get compound 24a (13 mg, 6% yield) m/z = 410 (M+l).

Reference： [1]Patent: WO2019/241796,2019,A1 .Location in patent: Page/Page column 72; 75; 147; 159

73
[ 5994-87-6 ]
[ 635-26-7 ]
P,P-diphenyl-N-(o-tolyl) phosphinic amide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
82%	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

74
[ 635-26-7 ]
[ 95-46-5 ]

Yield	Reaction Conditions	Operation in experiment
30%	With boron tribromide; dimethyl sulfoxide; at 80℃; for 1h;	General procedure: A 30-mL of round-bottomed flask was placed in ice. Arylhydrazine (0.5 mmol), CPME (or CH2Cl2) 0.2 mL was added. Then 2.4 equiv. of boron bromide (BBr3) was added gently. DMSO 0.2 mL was added in dropwise through a syringe. The mixture was then placed in hot plate (80oC), stirred in 1 hour under air. The yield of product was determined by 1H NMR (1,3,5 trioxane, CDCl3). The crude product was purified by liquid extraction with CH2Cl2 wash by sat. NaHCO3, dried over Na2SO4, column chromatography (Hexane 100% or Hexane: EtOAc =20:1).

Reference： [1]Tetrahedron Letters,2020,vol. 61

75
[ 13669-42-6 ]
[ 635-26-7 ]
3-((2-(2-methylphenyl)hydrazineylidene)methyl)quinoline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
35%	With sodium acetate; In ethanol; water; for 2h;	General procedure: The quinoline-3-carbaldehyde (0.1 mmol) was dissolved in EtOH and reacted with 0.13 mmol of phenyl hydrazine hydrochloride or derivative compounds in the presence of a solution of 0.4 g of sodium acetate in water for about 2 h. The precipitate formed at the end of the reaction was filtered off. The crystals obtained were purified by recrystallization from ethanol. The final compounds were obtained as amixture of E/Z stereoisomers.

Reference： [1]Bioorganic Chemistry,2020,vol. 101

76
[ 32294-60-3 ]
[ 635-26-7 ]
[ 861516-75-8 ]
[ 6243-26-1 ]

Yield	Reaction Conditions	Operation in experiment
1: 68% 2: 24%	With triethylamine In benzene at 60℃; for 24h;	3.2. General Procedure for Synthesis of Diaryl Tellurides from Arylhydrazine Hydrochlorides and Diaryl Ditellurides under Air General procedure: Arylhydrazine hydrochloride 1 (1.0 mmol), diaryl ditellurides 2 (0.25 mmol), Et3N (3.0 eq. vs. 1), and benzene (3.0 mL) were added to a 30 mL flask equipped with a stir bar. The resulting solution was stirred at 60 C in open air for 24 h. After the reaction was complete, the solvent was removed under reduced pressure. The residue was dissolved in AcOMe (10 mL) and filtered using silica gel. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by preparative thin-layer chromatography (eluent: CH2Cl2/iso-hexane) to afford the corresponding unsymmetrical or symmetrical diaryl tellurides 3.

Reference： [1]Chen, Qiqi; Kodama, Shintaro; Nomoto, Akihiro; Ogawa, Akiya; Sato, Fumiya; Yamamoto, Yuki [Molecules, 2022, vol. 27, # 3]

77
[ 571-55-1 ]
[ 635-26-7 ]
[ 948293-82-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: triethylamine / ethanol / 3 h / 80 °C 2: sodium hydroxide; water / ethanol / 1 h / 80 °C

Reference： [1]Abell, Chris; Blundell, Tom L.; Brown, Karen P.; Coyne, Anthony G.; Di Pietro, Ornella; Floto, R. Andres; Hess, Jeannine; Holland, Matthew T. O.; Kim, So Yeon; Marchetti, Chiara; Mendes, Vitor; Acebrón-García-De-Eulate, Marta; Mayol-Llinàs, Joan [Journal of Medicinal Chemistry, 2022, vol. 65, # 3, p. 2149 - 2173]

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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
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P401
P402	Store in a dry place.
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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
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P501	Dispose of contents/container to ...
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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
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H228	Flammable solid
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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. 635-26-7 ] {[proInfo.proName]}

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[ 635-26-7 ] Synthesis Path-Upstream 1~2

[ 635-26-7 ] Synthesis Path-Downstream 1~77

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Aryls

Amines

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