[ CAS No. 614-65-3 ] {[proInfo.proName]}

Name: 614-65-3|2-((2-Phenylhydrazono)methyl)phenol|98%
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Quality Control of [ 614-65-3 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 614-65-3 ]

SDS Specification

Alternatived Products of [ 614-65-3 ]

Product Details of [ 614-65-3 ]

CAS No. :	614-65-3	MDL No. :	MFCD00136159
Formula :	C₁₃H₁₂N₂O	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	SERARPRVBWDEBA-GXDHUFHOSA-N
M.W :	212.25	Pubchem ID :	135401296
Synonyms :

Calculated chemistry of [ 614-65-3 ]

Physicochemical Properties

Num. heavy atoms :	16
Num. arom. heavy atoms :	12
Fraction Csp3 :	0.0
Num. rotatable bonds :	3
Num. H-bond acceptors :	2.0
Num. H-bond donors :	2.0
Molar Refractivity :	65.94
TPSA :	44.62 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.17 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.86
Log Po/w (XLOGP3) :	3.41
Log Po/w (WLOGP) :	2.65
Log Po/w (MLOGP) :	2.54
Log Po/w (SILICOS-IT) :	2.57
Consensus Log Po/w :	2.61

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.66
Solubility :	0.0463 mg/ml ; 0.000218 mol/l
Class :	Soluble
Log S (Ali) :	-4.03
Solubility :	0.02 mg/ml ; 0.000094 mol/l
Class :	Moderately soluble
Log S (SILICOS-IT) :	-4.49
Solubility :	0.00685 mg/ml ; 0.0000323 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	1.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.21

Safety of [ 614-65-3 ]

Signal Word:	Danger	Class:	8
Precautionary Statements:	P264-P270-P280-P301+P312+P330-P305+P351+P338+P310-P501	UN#:	1759
Hazard Statements:	H302-H318	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 614-65-3 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 614-65-3 ]
Downstream synthetic route of [ 614-65-3 ]

[ 614-65-3 ] Synthesis Path-Upstream 1~1

1
[ 614-65-3 ]
[ 99498-65-4 ]

Reference： [1] Tetrahedron Letters, 2013, vol. 54, # 31, p. 4076 - 4079

[ 614-65-3 ] Synthesis Path-Downstream 1~88

1
2-benzoyloxy-benzaldehyde phenylhydrazone [ No CAS ]
2-benzoyloxy-benzaldehyde-(benzoyl-phenyl-hydrazone) [ No CAS ]
[ 614-65-3 ]

Yield	Reaction Conditions	Operation in experiment
	With acetic acid

Reference： [1]Auwers [Justus Liebigs Annalen der Chemie, 1909, vol. 365, p. 315,338] Auwers; Sonnenstuhl [Chemische Berichte, 1904, vol. 37, p. 3940]

2
[ 141-97-9 ]
[ 614-65-3 ]
[ 86100-07-4 ]

Yield	Reaction Conditions	Operation in experiment
69%	With lanthanum(lll) triflate In neat (no solvent) at 130℃; for 8h;
	With zinc(II) chloride at 130 - 135℃;

Reference： [1]Hariprasad, Kurma Siva; Prasad, Kasagani Veera; Raju, Bhimapaka China [RSC Advances, 2016, vol. 6, # 110, p. 108654 - 108661]
[2]Minunni [Atti della Accademia Nazionale dei Lincei, Classe di Scienze Fisiche, Matematiche e Naturali, Rendiconti, 1905, vol. <5> 14 II, p. 418][Gazzetta Chimica Italiana, 1925, vol. 55, p. 535] Minunni; Lazzarini [Atti della Accademia Nazionale dei Lincei, Classe di Scienze Fisiche, Matematiche e Naturali, Rendiconti, 1906, vol. <5> 15 I, p. 137]

3
[ 59-88-1 ]
[ 90-02-8 ]
[ 614-65-3 ]

Yield	Reaction Conditions	Operation in experiment
	With water; sodium acetate
	With sodium acetate at 80 - 90℃; for 0.5h; grinding; neat (no solvent, solid phase);
	With sodium acetate In water at 20℃;	General procedure: By wearing disposable gloves, solid phenylhydrazinehydrochloride, a stable white fluffy solid, was transferredby a spatula from the reagent bottle into test tubesin a fume hood. The fume hood was not switched on. Thetest tubes can then be used on an open bench. Initially,50-mg samples of phenylhydrazine hydrochloride wereweighed out with a balance, and it was verified that thisquantity was satisfactory for the test with aldehydes andketones. An estimated quantity from a spatula in a fumehood, switched off, was used for simplicity as was thequantity of NaOAc . 3H2O (50 mg or an excess). Weassume this is likely to be the scenario in a school forsimplicity, speed and safety. We also used 1-mL aliquotsof reagent from a standard solution which had been keptsealed for 2 months (0.5 g of phenylhydrazine hydrochloridein 10-mL H2O). Phenylhydrazine hydrochlorideor phenylhydrazine hydrochloride and NaOAc . 3H2O were mixed in water (8 mL) in a test tube at RT by shakingor with upwards and downwards movements of aspatula. Five drops of the aldehyde or ketone was addedand a precipitate formed within seconds with shaking.The test tube was not stoppered with a bung but wasshaken from side to side with the top held in one handbetween thumb and forefinger. The test with glycolaldehydewas heated at 50 °C for 5 min in a water bath

Reference： [1]Fischer,E. [Chemische Berichte, 1884, vol. 17, p. 579,581][Chemische Berichte, 1887, vol. 20, p. 821]
[2]Pradhan, Kiran; Selvaraj, Kaliaperumal; Nanda, Ashis K. [Chemistry Letters, 2010, vol. 39, # 10, p. 1078 - 1079]
[3]Plater, M John [Journal of Chemical Research, 2020, vol. 44, # 1-2, p. 104 - 107]

4
[ 90-02-8 ]
[ 100-63-0 ]
[ 614-65-3 ]

Yield	Reaction Conditions	Operation in experiment
97.9%	In water; ethyl acetate at 20℃; for 0.00416667h;	3 Salicylaldehyde Phenylhydrazone-FIGS. 12 and 13A and 13B A solvent mixture was prepared with 4 mL ethyl lactate and 1 mL water. To a beaker containing 10 mmol salicylaldehyde, 2 mL of the solvent was added. To a separate beaker was added 10 mmol phenylhydrazine with 2 mL of the solvent. The two solutions were combined, the remaining solvent used to rinse the empty beaker, and the rinse added to the reaction solution. The reaction solution was allowed to sit undisturbed at room temperature for 15 s for crystallization to complete, then transferred to an ice bath. The product was vacuum filtered, rinsed with ice-cold water, and air dried overnight. 1H-NMR (400 MHz, CHLOROFORM-D) δ 10.91 (s, 1H), 7.78 (s, 1H), 7.48 (s, 1H), 7.32-7.22 (m, 3H), 7.12 (dd, J=7.6, 0.9 Hz, 1H), 7.02-6.88 (m, 5H)13C-NMR (101 MHz, CHLOROFORM-D) δ 157.1, 143.5, 141.3, 130.1, 129.7, 129.5, 121.0, 119.6, 118.6, 116.7, 112.7 DEPT-135 NMR (101 MHz, CHLOROFORM-D) δ 141.3, 130.1, 129.7, 129.5, 121.0, 119.6, 116.7, 112.7
95%	In water; acetonitrile at 20℃;
92%	In ethanol

89%	In methanol Reflux;	Typical procedure for preparation phenylhydrazones. Preparation Method IV (see Scheme 4) General procedure: Preparation of 3,5-dichloro-6-((2-phenylhydrazono)methyl)phenol (SA29). A methanol (50ml) solution of 3,5-dichloro-2-hydroxybenzaldehyde (191mg; 1mmol) and phenylhydrazine (1.08mg; 1mmol) was refluxed for 4h. Solvent was evaporated to an oily residue that crystalized upon cooling. This residue was dissolved in hot hexane (∼100ml) and left at room temperature. The formed crystalline product was separated by filtration, washed with hexane (3×10ml) and dried on air to give pure product (260mg; 92%).
80%	In ethanol for 0.5h;
72%	In methanol for 1h;	Synthesis of 2-((2-phenylhydrazono)methyl)phenol (L¹H2) A solution of salicylaldehyde (0.61 g, 5 mmol) in methanol (10 ml) was added to a solution of phenyl hydrazine (0.54 g, 5 mmol) in methanol (10 ml) with continuous stirring. After 1 h of stirring, the red-brown colored solid precipitate was filtered off and washed thoroughly with methanol and diethyl ether. Yield: 0.76 g (72 %). Anal.Calcd. for C13H12N2O (212.09): C, 73.5; H, 5.7; N, 13.2. Found: C, 73.2; H, 5.6; N, 13.1 %. IR (KBr disk, cm-1): 1590 (νC=N)s, 1490 m, 1272 m, 1152w, 743 m, 680 w cm-1. UV-Vis (CH2Cl2; λmax, nm (ε, M-1 cm-1)): 343 (13,330), 300 (6550), 240 (8390). 1H NMR (CDCl3, 500 MHz): d 10.72 (s, 1H), 7.80 (s, 1H), 7.32-7.22 (m, 3H), 7.14 (d, 1H), 7.01-6.88 (m, 6H) ppm. 13C NMR (CDCl3, 500 MHz): d 157.10, 143.46, 141.29, 130.12, 129.65, 129.47, 120.98, 119.60, 118.60, 116.68, 112.72 ppm.
	With ethanol
	With ligroine; diethyl ether
	In ethanol for 0.5h; Heating;
	In methanol at -0.16℃;
	In methanol for 2h; Reflux;	2.2.1. Salicylaldehyde phenylhydrazone (SAPH) The ligand is easily prepared in good yield from inexpensive starting materials and is simple to isolate in pure form. It was prepared according the method described in Ref. [14b]. Methanolic solution of phenylhydrazine (11 mL, 0.1 mol) and salicylaldehyde (10.5 mL, 0.1 mol) was refluxed for 2 h under constant stirring. The immediately formed yellow-white solid was collected by vacuum filtration, washed repeatedly by ethanol to remove any excess of reactants and finally dried in furnace at 80 °C for 3 h. The resulting ligand with the formula C13H12N2O was recrystallized from EtOH and melted at 142 °C (lit.mp 140-142 °C) [15] and [17]. The ligand structure was confirmed by IR spectroscopy and its purity was checked by mass spectrometry. The mass spectrum of the free ligand exhibited a molecular ion peak (M+ value) at m/e = 212; calc. = 212.25. SAPH is air stable and easily soluble in most of organic solvents e.g., ethanol, chloroform, acetone and benzene.
	With potassium chloride; sodium chloride In N,N-dimethyl-formamide at 25℃;
	In ethanol at 20℃; for 0.25h;	General One-Pot Procedure for the Preparation of Ethyl 5-Methyl-1,3-diaryl-1H-pyrazole-4-carboxylates 6 General procedure: Phenyl hydrazine (0.119 g, 1.00 mmol, 1.1 equiv) was added to a stirred solution of benzaldehyde (0.106 g, 1.00 mmol) in EtOH (5 mL). After stirring at room temperature for 15 min, the benzaldehyde phenyl hydrazone was formed (based on thin-layer chromatographic, TLC, analysis). Hg(OAc)2 (0.478 g, 1.5 mmol, 1.5 equiv) in 5 ml EtOH and ethyl but-2-ynoate (0.224 g, 2.00 mmol, 2.0 equiv) were added simultaneously to the reaction mixture from two separate droppers. The contents were then allowed to stir at room temperature for 30 min (1.0 h total). On completion of the reaction, the reaction mixture was extracted with ethyl acetate (3X5 mL). The combined organic layer was washed with 1 M KBr solution (to remove mercury salts) and with brine, dried over anhydrous Na2SO4, and then concentrated under reduced pressure. The crude product was purified by column chromatography (n-hexane/EtOAc 95/05) to give two fractions. On evaporation, 6a was obtained as a white solid (0.277 g, 96%) and 8a as an off-white solid (0.057 g, 2%).
	In ethanol at 170 - 180℃; for 1h;	3 Preparation of 2-((2-phenylhydrazono)methyl)phenol (1a) Salicylaldehyde (5.3 ml, 0.05 mol) was added to phenyl hydrazine (4.91 ml, 0.05 mol) and added 30 ml of ethanol absolute as solvent. The flask was related with condenser under reflux system and solution boiled at 170-180 °C for 1h then transfer solution to beaker and stilled in room temperature or cooled, the precipitated hydrazones would be collected and filtered, washed with ethanol then dried. The product crystallization from ethanol gave yellow crystals of title compound (2-((2-phenylhydrazono)methyl)phenol) m.p 133-135°C. δ H (DMSO, 500MHz) 6.78-7.56 (9H, m, Ar-H), 8.2 (1H, s, CH=N), 10.42 (1H, s, OH), 10.55 (1H, s, NH); δ C (DMSO, 500MHz) 111.70-144.72 (10C-Ar), 155.64 (CH=N).
	In ethanol for 0.5h;
	In ethanol
	at 25℃;
	In methanol at 20℃;
	In methanol for 4h; Reflux;
	In ethanol for 0.5h; Reflux;	Preparation of the Ligands General procedure: Hydrazones of salicylaldehyde and 2'-hydroxyacetophenone were prepared by the gradual addition of salicylaldehyde/2'-hydroxyacetophenone to the ethanolic solution of hydrazine hydrate, phenylhydrazine or 2,4-dinitrophenylhydrazine in equimolar ratio. Due to insoluble nature of 2,4-dinitrophenylhydrazine in ethanol, a minimum quantity of sulfuric acid was added into its ethanolic suspension to make its homogeneous solution. The mixture was stirred under reflux for half an hour and then cooled in an ice bath. The precipitate so obtained was filterted, washed with ethanol and recrystallized from hot ethanol or glacial acetic acid in case of 2,4-dinitrophenylhydrazone derivatives

Reference： [1]Current Patent Assignee: STATE UNIVERSITY OF NEW YORK - US2021/323911, 2021, A1 Location in patent: Paragraph 0184-0185
[2]Hariprasad, Kurma Siva; Prasad, Kasagani Veera; Raju, Bhimapaka China [RSC Advances, 2016, vol. 6, # 110, p. 108654 - 108661]
[3]Ali, Tarik E.; Assiri, Mohammed A.; Yahia [Synthetic Communications, 2018, vol. 48, # 14, p. 1828 - 1837]
[4]Backes, Gregory L.; Neumann, Donna M.; Jursic, Branko S. [Bioorganic and Medicinal Chemistry, 2014, vol. 22, # 17, p. 4629 - 4636]
[5]Akhbar, Ahmed R.; Chudasama, Vijay; Fitzmaurice, Richard J.; Powell, Lyn; Caddick, Stephen [Chemical Communications, 2014, vol. 50, # 6, p. 743 - 746]
[6]Ghosh, Kaushik; Kumar, Rajan; Kumar, Sushil; Bala, Manju; Singh, Udai P. [Transition Metal Chemistry, 2015, vol. 40, # 8, p. 831 - 837]
[7]Roessing [Chemische Berichte, 1884, vol. 17, p. 2004]
[8]Landrieu [Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1905, vol. 141, p. 359]
[9]Biltz [Chemische Berichte, 1894, vol. 27, p. 2289] Lockemann; Lucius [Chemische Berichte, 1913, vol. 46, p. 1014]
[10]Khera, B.; Sharma, A. K.; Kaushik, N. K. [Bulletin de la Societe Chimique de France, 1984, vol. 1, # 5-6, p. 172 - 174] Khera, Brij; Sharma, Anand Kumar; Kaushik, Narender Kumar [Bulletin of the Chemical Society of Japan, 1985, vol. 58, # 2, p. 793 - 794]
[11]Mondal, Biplab; Chakraborty, Soma; Munshi, Pradip; Walawalkar, Mrinalini G.; Lahiri, Goutam Kumar [Journal of the Chemical Society, Dalton Transactions, 2000, # 14, p. 2327 - 2336]
[12]Location in patent: experimental part Ahmed, Ayman H.; Thabet [Journal of Molecular Structure, 2011, vol. 1006, # 1-3, p. 527 - 535]
[13]Kool, Eric T.; Park, Do-Hyoung; Crisalli, Pete [Journal of the American Chemical Society, 2013, vol. 135, # 47, p. 17663 - 17666]
[14]Ningaiah, Srikantamurthy; Doddaramappa, Shridevi D.; Chandra; Madegowda, Mahendra; Keshavamurthy, Shubakara; Bhadraiah, Umesha K. [Synthetic Communications, 2014, vol. 44, # 15, p. 2222 - 2231]
[15]Al-Sehemi, Abdullah G.; Irfan, Ahmad; Al-Melfi, Mohrah Abdullah M.; Al-Ghamdi, Ahmed A.; Shalaan [Journal of Photochemistry and Photobiology A: Chemistry, 2014, vol. 292, p. 1 - 9]
[16]Das, Diganta Kumar; Goswami, Priyanka; Sarma, Smita [Journal of Fluorescence, 2013, vol. 23, # 3, p. 503 - 508]
[17]Al-Omair, Mohammed A.; Sayed, Abdelwahed R.; Youssef, Magdy M. [Molecules, 2015, vol. 20, # 2, p. 2591 - 2610] Arjuna, Anania; Kaur, Manpreet; Singh, Baldev [Journal of Heterocyclic Chemistry, 2019]
[18]Dilek, Ozlem; Sorrentino, Anthony M.; Bane, Susan [Synlett, 2016, vol. 27, # 9, p. 1335 - 1338]
[19]Panda, Niranjan; Ojha, Subhadra [Journal of Organometallic Chemistry, 2018, vol. 861, p. 244 - 251]
[20]Gurubrahamam, Ramani; Nagaraju, Koppanathi; Chen, Kwunmin [Chemical Communications, 2018, vol. 54, # 47, p. 6048 - 6051]
[21]Kaushik, Narender Kumar; Khera, Brij; Sharma, Anand Kumar [Bulletin of the Chemical Society of Japan, 2021, vol. 58, # 2, p. 793 - 794]

5
[ 98-88-4 ]
[ 614-65-3 ]
2-benzoyloxy-benzaldehyde-(benzoyl-phenyl-hydrazone) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine; diethyl ether
	With sodium hydroxide

Reference： [1]Lockemann; Lucius [Chemische Berichte, 1913, vol. 46, p. 1019]
[2]Lockemann; Lucius [Chemische Berichte, 1913, vol. 46, p. 1019]

6
[ 64-17-5 ]
[ 959-36-4 ]
[ 100-63-0 ]
[ 614-65-3 ]

Reference： [1]Monatshefte fur Chemie,1909,vol. 30,p. 33

7
[ 614-65-3 ]
[ 3526-45-2 ]

Yield	Reaction Conditions	Operation in experiment
	With ethanol; acetic acid; zinc

Reference： [1]Franzen [Journal fur praktische Chemie (Leipzig 1954), 1905, vol. <2>72, p. 218]

8
[ 614-65-3 ]
α-salicylosazone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With air; ethanol

Reference： [1]Biltz [Justus Liebigs Annalen der Chemie, 1899, vol. 305, p. 179,182]

9
[ 614-65-3 ]
salicylaldehyde-(4-bromo-phenylhydrazone) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With bromine; acetic acid

Reference： [1]Vanghelovitch [Buletinul Societatii de Chimie din Romania, 1927, vol. 9, p. 59][Chemisches Zentralblatt, 1928, vol. 99, # I, p. 1951]

10
[ 614-65-3 ]
2-(4,4'-bis-salicylidenehydrazino-benzhydryl)-phenol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With zinc(II) chloride

Reference： [1]Giacalone [Gazzetta Chimica Italiana, 1931, vol. 61, p. 642,644]

11
[ 614-65-3 ]
2-difluoroboranyloxy-benzaldehyde (<i>E</i>)-phenylhydrazone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With boron trifluoride In benzene

Reference： [1]Umland,F. et al. [Chemische Berichte, 1973, vol. 106, p. 2427 - 2437]

12
[ 90-02-8 ]
[ 74885-89-5 ]
[ 614-65-3 ]

Yield	Reaction Conditions	Operation in experiment
66%	With toluene-4-sulfonic acid In toluene Heating;

Reference： [1]Voegtle, Fritz; Mueller, Walter M. [Chemische Berichte, 1980, vol. 113, # 6, p. 2081 - 2085]

13
[ 62-53-3 ]
[ 614-65-3 ]
[ 33737-92-7 ]

Yield	Reaction Conditions	Operation in experiment
76%	With pyridine; hydrogenchloride; sodium nitrite In water for 4h;

Reference： [1]Stepanov, B. I.; Avramenko, G. V.; Khamud, Salekh; Mustafaeva, Sh. I. [Journal of general chemistry of the USSR, 1986, vol. 56, # 2, p. 339 - 341][Zhurnal Obshchei Khimii, 1986, vol. 56, # 2, p. 390 - 392]

14
[ 60-24-2 ]
[ 614-65-3 ]
[ 95104-63-5 ]

Yield	Reaction Conditions	Operation in experiment
61%	With triethylamine In acetone for 1h; Heating;

Reference： [1]Tirant, Michael; Smith, Thomas D. [Synthesis, 1984, # 10, p. 833 - 834]

15
[ 504-64-3 ]
[ 614-65-3 ]
[ 1846-92-0 ]

Yield	Reaction Conditions	Operation in experiment
67%	In diethyl ether 1) 0 deg C, 8 h, 2) r.t., 3 d;

Reference： [1]Bonsignore, Leonardo; Cabiddu, Salvatore; Loy, Giuseppe; Secci, Mario [Journal of Heterocyclic Chemistry, 1985, vol. 22, p. 463 - 464]

16
5-Methyl-2H-pyrazole-3-diazonium; chloride [ No CAS ]
[ 614-65-3 ]
C₁₇H₁₆N₆O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine In water at 5 - 10℃; for 2h; Yield given;

Reference： [1]Shmelev, L. V.; Anpenova, E. P.; Avramenko, G. V.; Bezuglaya, Z. V.; Tolkachev, D. V.; Gurevich, P. I. [Russian Journal of Organic Chemistry, 1993, vol. 29, # 3.2, p. 502 - 506][Zhurnal Organicheskoi Khimii, 1993, vol. 29, # 3, p. 601 - 606]

17
[ 614-65-3 ]
[ 95096-26-7 ]

Yield	Reaction Conditions	Operation in experiment
71%	With hydrogen sulfide; triethylamine In acetone for 0.166667h;

Reference： [1]Tirant, Michael; Smith, Thomas D. [Synthesis, 1984, # 10, p. 833 - 834]

18
[ 614-65-3 ]
[ 81323-15-1 ]

Yield	Reaction Conditions	Operation in experiment
93%	With hydroxylamine hydrochloride; sodium acetate In ethanol for 2.5h; Heating;

Reference： [1]Siddiqui, Amin A.; Khan, Naseem H.; Basheeruddin [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1981, vol. 20, # 11, p. 1003 - 1005]

19
[ 614-65-3 ]
C₂₆H₂₆N₄O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%	With zinc In ethanol; chloroform for 4h; Heating;

Reference： [1]Khan, Naseem H.; Zuberi, Rashid H.; Siddiqui, Amin A. [Synthetic Communications, 1980, vol. 10, # 5, p. 363 - 372]

20
[ 614-65-3 ]
[ 1132-39-4 ]
[ 69-72-7 ]

Yield	Reaction Conditions	Operation in experiment
1: 27% 2: 31%	With selenium(IV) oxide In N,N-dimethyl-formamide at 100℃; for 4h;

Reference： [1]Dakova, B. Y.; Evers, M. J.; Christiaens, L. R.; Guillaume, M. R. [Bulletin des Societes Chimiques Belges, 1987, vol. 96, # 3, p. 219 - 224]

21
[ 89-95-2 ]
[ 100-63-0 ]
[ 614-65-3 ]

Yield	Reaction Conditions	Operation in experiment
91%	With Dowex resin acid form In ethanol for 0.833333h;
	With potassium chloride In ethanol; water at 35℃;
	With potassium chloride In ethanol; water at 35℃;

Reference： [1]Niknam, Khodabakhsh; Kiasat, Ali Reza; Karimi, Sadegh [Synthetic Communications, 2005, vol. 35, # 17, p. 2231 - 2236]
[2]Mostaghim; Habibi Yangjeh; Gholami [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1999, vol. 38, # 8, p. 976 - 978]
[3]Mostaghim; Habibi Yangjeh; Gholami [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1999, vol. 38, # 8, p. 976 - 978]

Yield	Reaction Conditions	Operation in experiment
	With emulsin

23
[ 614-65-3 ]
3,3'-Bis-(2-hydroxy-phenyl)-5,5'-diphenyl-1,1'-(3,3'-dimethoxy-biphenyl-4,4'-diyl)-di-formazan [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With methanol; ethanol; sodium acetate Reagens 4: Pyridin;

Reference： [1]Ried; Gick [Justus Liebigs Annalen der Chemie, 1953, vol. 581, p. 16,22]

24
[ 100-63-0 ]
[ 614-65-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 82 percent / toluene / Ambient temperature 2: 66 percent / p-TsOH / toluene / Heating

Reference： [1]Voegtle, Fritz; Mueller, Walter M. [Chemische Berichte, 1980, vol. 113, # 6, p. 2081 - 2085]

25
[ 614-65-3 ]
N-Phenyl-N'-(2-hydroxy-α-amino)benzylhydrazine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 93 percent / NH₂OH*HCl, NaOAc / ethanol / 2.5 h / Heating 2: 96 percent / H₂ / 5percent Pd/C / benzene / 2.5 h / 1603.2 Torr

Reference： [1]Siddiqui, Amin A.; Khan, Naseem H.; Basheeruddin [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1981, vol. 20, # 11, p. 1003 - 1005]

26
[ 614-65-3 ]
[ 531-81-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 67 percent / diethyl ether / 1) 0 deg C, 8 h, 2) r.t., 3 d 2: 20percent aq. NaOH

Reference： [1]Bonsignore, Leonardo; Cabiddu, Salvatore; Loy, Giuseppe; Secci, Mario [Journal of Heterocyclic Chemistry, 1985, vol. 22, p. 463 - 464]

27
[ 19820-51-0 ]
[ 614-65-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: alcohol 2: glacial acetic acid

Reference： [1]Auwers [Justus Liebigs Annalen der Chemie, 1909, vol. 365, p. 315,338]

28
[ 100-63-0 ]
[ 614-65-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: alcohol 2: glacial acetic acid

Reference： [1]Auwers [Justus Liebigs Annalen der Chemie, 1909, vol. 365, p. 315,338]

29
[ 614-65-3 ]
2,2'-diacetoxy-benzil-bis-(acetyl-phenyl-hydrazone) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: alcohol; alkali; air 2: nitrobenzene 3: sodium acetate
	Multi-step reaction with 2 steps 1: alcohol; alkali; air 2: potassium acetate

Reference： [1]Biltz [Justus Liebigs Annalen der Chemie, 1899, vol. 305, p. 179,182]
[2]Biltz [Justus Liebigs Annalen der Chemie, 1899, vol. 305, p. 179,182]

30
[ 614-65-3 ]
3-(2-hydroxy-phenyl)-5-methyl-1-phenyl-1<i>H</i>-pyrazole-4-carboxylic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: zinc chloride / 130 - 135 °C 2: alcoholic KOH-solution

Reference： [1]Minunni [Atti della Accademia Nazionale dei Lincei, Classe di Scienze Fisiche, Matematiche e Naturali, Rendiconti, 1905, vol. <5> 14 II, p. 418][Gazzetta Chimica Italiana, 1925, vol. 55, p. 535] Minunni; Lazzarini [Atti della Accademia Nazionale dei Lincei, Classe di Scienze Fisiche, Matematiche e Naturali, Rendiconti, 1906, vol. <5> 15 I, p. 137]

31
[ 12148-49-1 ]
[ 614-65-3 ]
(C₉H₇)2ZrCl(OC₆H₄CHNNHC₆H₅) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60%	In tetrahydrofuran byproducts: HCl; a soln. of the Zr-complex was added to a soln. of the hydrazone (both in THF) and the mixt. refluxed for 10-12 h;; after partial evapn. in vac., petroleum ether was added, filtered, washed with petroleum ether, dried in vac. and recrystallized from CH2Cl2; elem. anal.;;

Reference： [1]Sharma, A. K.; Khera, B.; Kaushik, N. K. [Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical and Analytical, 1986, vol. 25, # 9, p. 865 - 867]

32
[ 12113-02-9 ]
[ 614-65-3 ]
(C₉H₇)2TiCl(OC₆H₄CHNNHC₆H₅) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
68%	In tetrahydrofuran byproducts: HCl; a soln. of the Ti-complex was added to a soln. of the hydrazone (both in THF) and the mixt. refluxed for 10-12 h;; after partial evapn. in vac., petroleum ether was added, filtered, washed with petroleum ether, dried in vac. and recrystallized from CH2Cl2; elem. anal.;;

Reference： [1]Sharma, A. K.; Khera, B.; Kaushik, N. K. [Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical and Analytical, 1986, vol. 25, # 9, p. 865 - 867]

33
dysprosium((III) oxide [ No CAS ]
[ 614-65-3 ]
{Dy(C₆H₄(O)CHNNHC₆H₅)(OH)2(OH₂)2} [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With H₂O In ethanol; nitric acid aq. HNO3; dissoln. of oxide in nitric acid by heating; dilution with water; slow addn. to hydrazone soln. (ethanol, slight excess at 1/1 molar ratio); stirring; adjusting to pH 8.77 with aq. ammonia; stirring, 15-20 min; pptn.; washing (water, ethanol 50%, ethanol); drying at 90°C; elem. anal.;

Reference： [1]Thankarajan, N.; Kumar, K. Pradeep [Journal of the Indian Chemical Society, 1992, vol. 69, p. 780 - 781]

34
erbium(III) oxide [ No CAS ]
[ 614-65-3 ]
{Er(C₆H₄(O)CHNNHC₆H₅)(OH)2(OH₂)2} [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With H₂O In ethanol; nitric acid aq. HNO3; dissoln. of oxide in nitric acid by heating; dilution with water; slow addn. to hydrazone soln. (ethanol, slight excess at 1/1 molar ratio); stirring; adjusting to pH 7.95 with aq. ammonia; stirring, 15-20 min; pptn.; washing (water, ethanol 50%, ethanol); drying at 90°C; elem. anal.;

Reference： [1]Thankarajan, N.; Kumar, K. Pradeep [Journal of the Indian Chemical Society, 1992, vol. 69, p. 780 - 781]

35
europium(III) oxide [ No CAS ]
[ 614-65-3 ]
{Eu(C₆H₄(O)CHNNHC₆H₅)(OH)2(OH₂)2} [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With H₂O In ethanol; nitric acid aq. HNO3; dissoln. of oxide in nitric acid by heating; dilution with water; slow addn. to hydrazone soln. (ethanol, slight excess at 1/1 molar ratio); stirring; adjusting to pH 8.34 with aq. ammonia; stirring, 15-20 min; pptn.; washing (water, ethanol 50%, ethanol); drying at 90°C; elem. anal.;

Reference： [1]Thankarajan, N.; Kumar, K. Pradeep [Journal of the Indian Chemical Society, 1992, vol. 69, p. 780 - 781]

36
gadolinium(III) oxide [ No CAS ]
[ 614-65-3 ]
{Gd(C₆H₄(O)CHNNHC₆H₅)(OH)2(OH₂)2} [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With H₂O In ethanol; nitric acid aq. HNO3; dissoln. of oxide in nitric acid by heating; dilution with water; slow addn. to hydrazone soln. (ethanol, slight excess at 1/1 molar ratio); stirring; adjusting to pH 7.54 with aq. ammonia; stirring, 15-20 min; pptn.; washing (water, ethanol 50%, ethanol); drying at 90°C; elem. anal.;

Reference： [1]Thankarajan, N.; Kumar, K. Pradeep [Journal of the Indian Chemical Society, 1992, vol. 69, p. 780 - 781]

37
holmium(III) oxide [ No CAS ]
[ 614-65-3 ]
{Ho(C₆H₄(O)CHNNHC₆H₅)(OH)2(OH₂)2} [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With H₂O In ethanol; nitric acid aq. HNO3; dissoln. of oxide in nitric acid by heating; dilution with water; slow addn. to hydrazone soln. (ethanol, slight excess at 1/1 molar ratio); stirring; adjusting to pH 7.60 with aq. ammonia; stirring, 15-20 min; pptn.; washing (water, ethanol 50%, ethanol); drying at 90°C; elem. anal.;

Reference： [1]Thankarajan, N.; Kumar, K. Pradeep [Journal of the Indian Chemical Society, 1992, vol. 69, p. 780 - 781]

38
neodymium(III) oxide [ No CAS ]
[ 614-65-3 ]
{Nd(C₆H₄(O)CHNNHC₆H₅)(OH)2(OH₂)2} [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With H₂O In ethanol; nitric acid aq. HNO3; dissoln. of oxide in nitric acid by heating; dilution with water; slow addn. to hydrazone soln. (ethanol, slight excess at 1/1 molar ratio); stirring; adjusting to pH 7.84 with aq. ammonia; stirring, 15-20 min; pptn.; washing (water, ethanol 50%, ethanol); drying at 90°C; elem. anal.;

Reference： [1]Thankarajan, N.; Kumar, K. Pradeep [Journal of the Indian Chemical Society, 1992, vol. 69, p. 780 - 781]

39
lutetium(III) oxide [ No CAS ]
[ 614-65-3 ]
{Lu(C₆H₄(O)CHNNHC₆H₅)(OH)2(OH₂)2} [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With H₂O In ethanol; nitric acid aq. HNO3; dissoln. of oxide in nitric acid by heating; dilution with water; slow addn. to hydrazone soln. (ethanol, slight excess at 1/1 molar ratio); stirring; adjusting to pH 7.32 with aq. ammonia; stirring, 15-20 min; pptn.; washing (water, ethanol 50%, ethanol); drying at 90°C; elem. anal.;

Reference： [1]Thankarajan, N.; Kumar, K. Pradeep [Journal of the Indian Chemical Society, 1992, vol. 69, p. 780 - 781]

40
cerium (IV) ammonium nitrate [ No CAS ]
[ 614-65-3 ]
Ce⁽⁴⁺⁾*2C₆H₄(O)CHNNHC₆H₅^(1-)*2NO₃^(1-)*2H₂O={Ce(C₆H₄(O)CHNNHC₆H₅)2(NO₃)(OH₂)2}NO₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With H₂O In ethanol slow addn. of Ce salt soln. (50% ethanol) to hydrazone soln.; stirring, 5 min; crystn.; filtration; washing (water, ethanol 50%, ethanol); drying at 90°C; elem. anal.;

Reference： [1]Thankarajan, N.; Kumar, K. Pradeep [Journal of the Indian Chemical Society, 1992, vol. 69, p. 780 - 781]

41
[ 1291-32-3 ]
[ 614-65-3 ]
Zr(C₆H₄(O)CHNNHC₆H₅)(C₅H₅)2Cl [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
72%	In tetrahydrofuran reflux, 10 - 12 h,; filtered, evapn. of solvent in vac., crystals pptd. by petroleum ether, filtered, washed by petroleum ether, dried in vac., recrystd. from CH2Cl2; elem. anal.;

Reference： [1]Khera, B.; Sharma, A. K.; Kaushik, N. K. [Bulletin de la Societe Chimique de France, 1984, vol. I, p. 172 - 174]

42
[ 94-67-7 ]
nickel dichloride [ No CAS ]
[ 614-65-3 ]
[ 103992-66-1 ]

Yield	Reaction Conditions	Operation in experiment
70%	With NaOH In ethanol; water; acetone dropwise addn. of aq. soln. of NiCl2 to mixt. of NaOH and ligands in mixt. of acetone/EtOH/water 2:1:1 (stirring), pptn.; filtration off, washing (EtOH), drying (vac.); elem. anal.;

Reference： [1]Aggarwal, R. C.; Bala, Rashmi; Prasad, R. L. [Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 1986, vol. 42, # 6, p. 725 - 728]

43
samarium(III) oxide [ No CAS ]
[ 614-65-3 ]
{Sm(C₆H₄(O)CHNNHC₆H₅)(OH)2(OH₂)2} [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With H₂O In ethanol; nitric acid aq. HNO3; dissoln. of oxide in nitric acid by heating; dilution with water; slow addn. to hydrazone soln. (ethanol, slight excess at 1/1 molar ratio); stirring; adjusting to pH 7.81 with aq. ammonia; stirring, 15-20 min; pptn.; washing (water, ethanol 50%, ethanol); drying at 90°C; elem. anal.;

Reference： [1]Thankarajan, N.; Kumar, K. Pradeep [Journal of the Indian Chemical Society, 1992, vol. 69, p. 780 - 781]

44
thulia [ No CAS ]
[ 614-65-3 ]
{Tm(C₆H₄(O)CHNNHC₆H₅)(OH)2(OH₂)2} [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With H₂O In ethanol; nitric acid aq. HNO3; dissoln. of oxide in nitric acid by heating; dilution with water; slow addn. to hydrazone soln. (ethanol, slight excess at 1/1 molar ratio); stirring; adjusting to pH 8.51 with aq. ammonia; stirring, 15-20 min; pptn.; washing (water, ethanol 50%, ethanol); drying at 90°C; elem. anal.;

Reference： [1]Thankarajan, N.; Kumar, K. Pradeep [Journal of the Indian Chemical Society, 1992, vol. 69, p. 780 - 781]

45
terbium(III) oxide [ No CAS ]
[ 614-65-3 ]
Tb⁽⁴⁺⁾*2C₆H₄(O)CHNNHC₆H₅^(1-)*2OH^(1-)*3H₂O={Tb(C₆H₄(O)CHNNHC₆H₅)2(OH)2(OH₂)3} [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With H₂O In ethanol; nitric acid aq. HNO3; dissoln. of oxide in nitric acid by heating; dilution with water; slow addn. to hydrazone soln. (ethanol, slight excess at 1/2 molar ratio); stirring; adjusting to pH 6.01 with aq. ammonia; stirring, 15-20 min; pptn.; washing (water, ethanol 50%, ethanol); drying at 90°C; elem. anal.;

Reference： [1]Thankarajan, N.; Kumar, K. Pradeep [Journal of the Indian Chemical Society, 1992, vol. 69, p. 780 - 781]

46
ytterbium(III) oxide [ No CAS ]
[ 614-65-3 ]
{Yb(C₆H₄(O)CHNNHC₆H₅)(OH)2(OH₂)2} [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With H₂O In ethanol; nitric acid aq. HNO3; dissoln. of oxide in nitric acid by heating; dilution with water; slow addn. to hydrazone soln. (ethanol, slight excess at 1/1 molar ratio); stirring; adjusting to pH 8.21 with aq. ammonia; stirring, 15-20 min; pptn.; washing (water, ethanol 50%, ethanol); drying at 90°C; elem. anal.;

Reference： [1]Thankarajan, N.; Kumar, K. Pradeep [Journal of the Indian Chemical Society, 1992, vol. 69, p. 780 - 781]

47
praseodymium(III) oxide [ No CAS ]
[ 614-65-3 ]
{Pr(C₆H₄(O)CHNNHC₆H₅)(OH)2(OH₂)2} [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With H₂O In ethanol; nitric acid aq. HNO3; dissoln. of oxide in nitric acid by heating; dilution with water; slow addn. to hydrazone soln. (ethanol, slight excess at 1/1 molar ratio); stirring; adjusting to pH 7.91 with aq. ammonia; stirring, 15-20 min; pptn.; washing (water, ethanol 50%, ethanol); drying at 90°C; elem. anal.;

Reference： [1]Thankarajan, N.; Kumar, K. Pradeep [Journal of the Indian Chemical Society, 1992, vol. 69, p. 780 - 781]

48
[ 1271-19-8 ]
[ 614-65-3 ]
[ 97959-92-7 ]

Yield	Reaction Conditions	Operation in experiment
60%	In tetrahydrofuran to stirred soln. of Cp2TiCl2 in THF slowly added soln. of hydrazone in THF, refluxed at 68°C for 10-12 h; filtered, concd. in vac., pptd. ba adding petroleum ether, filtered, washed with petroleum ether, dried in vac., recrystd. from CH2Cl2-petroleum ether; elem. anal.;
60%	In tetrahydrofuran at 68℃;	Preparation of Complexes General procedure: To a stired solution of bis(cyclopentadienyl)titanium(IV) dichloride, (Cp)2TiCl2 (8 mmol) in 30 ml tetrahydrofuran, a solution containing 8 mmol of appropiate hydrazone or azine in 30 ml tetrahydrofuran was added slowly and the reaction mixture was refluxed for 10-12 h. It was then filtered an the volume of the filtrate was reduced to ca. 20 ml by evaporating the solvent under reduced pressure. The crystals of the product were precipitated by adding 80 ml petroleum ather (60-80 oC) to the concentrated filtrate. These were filtered, washed with petroleum ether and dried under vacuum. Recrystalized from dichloromethane by adding excess of petroleum ether.

Reference： [1]Khera, Brij; Sharma, Anand Kumar; Kaushik, Narender Kumar [Bulletin of the Chemical Society of Japan, 1985, vol. 58, # 2, p. 793 - 794]
[2]Kaushik, Narender Kumar; Khera, Brij; Sharma, Anand Kumar [Bulletin of the Chemical Society of Japan, 2021, vol. 58, # 2, p. 793 - 794]

49
[ 72905-30-7 ]
[ 614-65-3 ]
[ 297733-67-6 ]

Yield	Reaction Conditions	Operation in experiment
	With NaCH₃COO In methanol heated; solvent-removed, chromd. (SiO2);

Reference： [1]Mondai, Biplab; Chakraborty, Soma; Munshi, Pradip; Walawalkar, Mrinalini G.; Lahiri, Goutam Kumar [Journal of the Chemical Society, Dalton Transactions, 2000, # 14, p. 2327 - 2335]

50
[ 14126-40-0 ]
[ 614-65-3 ]
CoCl(P(C₆H₅)3)(C₁₃H₁₁N₂O) [ No CAS ]

Reference： [1]Inorganic Chemistry Communications,2010,vol. 13,p. 195 - 198

51
[ 32315-10-9 ]
[ 614-65-3 ]
[ 1355071-22-5 ]

Yield	Reaction Conditions	Operation in experiment
90%	With samarium; titanium tetrachloride In tetrahydrofuran for 2h; Reflux; Inert atmosphere;

Reference： [1]Location in patent: experimental part Dou, Guolan; Sun, Fang; Zhao, Xuan; Shi, Daqing [Chinese Journal of Chemistry, 2011, vol. 29, # 11, p. 2465 - 2470]

52
[ 107-21-1 ]
[ 614-65-3 ]
[ 895138-62-2 ]

Yield	Reaction Conditions	Operation in experiment
66%	With Iron(III) nitrate nonahydrate; dipotassium peroxodisulfate In neat (no solvent) at 20℃; for 12h; regioselective reaction;	Method A: General procedure: A mixture of diaryl hydrazones (0.51mmol), K2S2O8 (2 equiv.), Fe(NO3)3·9H2O (5mol%) and diol (1.02mmol, 2 equiv.) was stirred at room temperature for 12h. After complete consumption of hydrazone, the reaction mixture was poured into water (20mL) and extracted with dichloromethane (3×20mL). The combined organic layer was washed with water (50mL), dried over Na2SO4, and concentrated under reduced pressure. The residue was purified by column chromatography using ethyl acetate and petroleum ether as eluent to afford the desired pyrazoles.
63%	With tert.-butylhydroperoxide; iron(III) chloride; oxygen; acetylacetone at 120℃; for 6h; regioselective reaction;

Reference： [1]Panda, Niranjan; Ojha, Subhadra [Journal of Organometallic Chemistry, 2018, vol. 861, p. 244 - 251]
[2]Panda, Niranjan; Jena, Ashis Kumar [Journal of Organic Chemistry, 2012, vol. 77, # 20, p. 9401 - 9406,6] Panda, Niranjan; Jena, Ashis Kumar [Journal of Organic Chemistry, 2012, vol. 77, # 20, p. 9401 - 9406]

53
[ 57-55-6 ]
[ 614-65-3 ]
[ 72815-87-3 ]

Yield	Reaction Conditions	Operation in experiment
51%	With tert.-butylhydroperoxide; iron(III) chloride; oxygen; acetylacetone at 20℃; for 1h; regioselective reaction;

Reference： [1]Panda, Niranjan; Jena, Ashis Kumar [Journal of Organic Chemistry, 2012, vol. 77, # 20, p. 9401 - 9406,6] Panda, Niranjan; Jena, Ashis Kumar [Journal of Organic Chemistry, 2012, vol. 77, # 20, p. 9401 - 9406]

54
[ 59938-06-6 ]
[ 614-65-3 ]
C₁₇H₁₃F₃N₂O₂ [ No CAS ]

Reference： [1]Tetrahedron Letters,2013,vol. 54,p. 4076 - 4079

55
[ 614-65-3 ]
[ 99498-65-4 ]

Reference： [1]Tetrahedron Letters,2013,vol. 54,p. 4076 - 4079

56
[ 1078138-42-7 ]
[ 614-65-3 ]
C₂₁H₂₁O₄P [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With tributylphosphine In tetrahydrofuran at 60℃; for 12h;

Reference： [1]Rama Suresh; Prasad Tulichala; Kotikalapudi, Ramesh; Kumara Swamy [Journal of Heterocyclic Chemistry, 2014, vol. 51, # 3, p. 760 - 767]

57
[ 4341-76-8 ]
[ 614-65-3 ]
[ 1360084-68-9 ]

Yield	Reaction Conditions	Operation in experiment
	With mercury(II) diacetate In ethanol at 20℃; for 0.5h; regioselective reaction;	General One-Pot Procedure for the Preparation of Ethyl 5-Methyl-1,3-diaryl-1H-pyrazole-4-carboxylates 6 General procedure: Phenyl hydrazine (0.119 g, 1.00 mmol, 1.1 equiv) was added to a stirred solution of benzaldehyde (0.106 g, 1.00 mmol) in EtOH (5 mL). After stirring at room temperature for 15 min, the benzaldehyde phenyl hydrazone was formed (based on thin-layer chromatographic, TLC, analysis). Hg(OAc)2 (0.478 g, 1.5 mmol, 1.5 equiv) in 5 ml EtOH and ethyl but-2-ynoate (0.224 g, 2.00 mmol, 2.0 equiv) were added simultaneously to the reaction mixture from two separate droppers. The contents were then allowed to stir at room temperature for 30 min (1.0 h total). On completion of the reaction, the reaction mixture was extracted with ethyl acetate (3X5 mL). The combined organic layer was washed with 1 M KBr solution (to remove mercury salts) and with brine, dried over anhydrous Na2SO4, and then concentrated under reduced pressure. The crude product was purified by column chromatography (n-hexane/EtOAc 95/05) to give two fractions. On evaporation, 6a was obtained as a white solid (0.277 g, 96%) and 8a as an off-white solid (0.057 g, 2%).

Reference： [1]Ningaiah, Srikantamurthy; Doddaramappa, Shridevi D.; Chandra; Madegowda, Mahendra; Keshavamurthy, Shubakara; Bhadraiah, Umesha K. [Synthetic Communications, 2014, vol. 44, # 15, p. 2222 - 2231]

58
[ 670-54-2 ]
[ 614-65-3 ]
[ 94994-59-9 ]

Yield	Reaction Conditions	Operation in experiment
23%	In N,N-dimethyl-formamide at 400℃; for 6h;	6 Preparation of 2-{4-[2-(2-hydroxybenzylidene)hydrazino]phenyl}ethylene-1,1,2-tricarbonitrile (dye1) The 2-((2-phenylhydrazono)methyl)phenol (1a) (2.12 g, 0.01 mol) was dissolved in 20 ml DMF as solvent then added 1.28 g of TCNE direct gave dark color. The solution was boiled at 400°C under reflux for 6h. The solvent was removed and the residual solid collected and recrystallized from toluene/petroleum ether mixture to get dye1 (0.72 g, 23% yield) m.p 225-227°C. δ H (DMSO, 500MHz) 6.87-7.99 (8H, m, Ar-H), 8.45 (1H, s, CH=N), 10.2 (1H, s, OH exchange with D2O), 11.84 (s, 1H,NH exchange with D2O); δ C (DMSO, 500MHz) 78.69 and 142.28 (C=C), 114.01, 114.24 and 114.79 (3xC≡N), 112.72, 115.87, 119.25, 120.16, 125.27, 128.86, 132.78, 136.90, 150.94 and 156.39 (10C-Ar), 162.27(CH=N).

Reference： [1]Al-Sehemi, Abdullah G.; Irfan, Ahmad; Al-Melfi, Mohrah Abdullah M.; Al-Ghamdi, Ahmed A.; Shalaan [Journal of Photochemistry and Photobiology A: Chemistry, 2014, vol. 292, p. 1 - 9]

59
[ 614-65-3 ]
2-(4,5-dihydro-5-imino-4-phenyl-1,3,4-thiadiazol-2-yl)phenol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: N-Bromosuccinimide; dimethylsulfide / dichloromethane / -20 - 20 °C 2: ethanol / 6 h / Reflux

Reference： [1]Al-Omair, Mohammed A.; Sayed, Abdelwahed R.; Youssef, Magdy M. [Molecules, 2015, vol. 20, # 2, p. 2591 - 2610]

60
[ 614-65-3 ]
1-(2-hydroxyphenyl-3-phenyl-1,3,4-thiadiazol-4,(3H)-ylidene)hydrazine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: N-Bromosuccinimide; dimethylsulfide / dichloromethane / -20 - 20 °C 2: triethylamine / ethanol / 4 h / Reflux

Reference： [1]Al-Omair, Mohammed A.; Sayed, Abdelwahed R.; Youssef, Magdy M. [Molecules, 2015, vol. 20, # 2, p. 2591 - 2610]

61
[ 614-65-3 ]
2-hydroxy-N-phenylbenzohydrazonoyl bromide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86%	With N-Bromosuccinimide; dimethylsulfide In dichloromethane at -20 - 20℃;	Synthesis of 2-Hydroxy-N-phenylbenzohydrazonoyl Bromide (4) To a solution of N-bromosuccinimide (10 mmol) dissolved in CH2Cl2 (70 mL) at 0 °C was added dimethyl sulfide (1.12 g, 18 mmol) and the reaction mixture was stirred for 15 min at 0 °C and then kept in a deep freezer (-20 °C) overnight. To this solution was added the hydrazone (9 mmol) in CH2Cl2 (20 mL) and the reaction mixture was left in the deep freezer overnight and then allowed to warm to room temperature for 2 h. The progress of the reaction was monitored by TLC. The reaction mixture was quenched with cold water. The contents were extracted with CH2Cl2 (40 mL), washed with water (2 × 40 mL) and dried (MgSO4). The solvent was removed under reduced pressure and crystallization from MeOH afforded the final product 2-hydroxy-N-phenylbenzohydrazonoyl bromide(4).

Reference： [1]Al-Omair, Mohammed A.; Sayed, Abdelwahed R.; Youssef, Magdy M. [Molecules, 2015, vol. 20, # 2, p. 2591 - 2610]

62
[ 614-65-3 ]
2-(5-(2-hydroxyphenyl)-2,4-diphenyl-2H-1,2,4-triazol-3(4H)-ylidene)malononitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: N-Bromosuccinimide; dimethylsulfide / dichloromethane / -20 - 20 °C 2: triethylamine / ethanol / 6 h / Reflux

Reference： [1]Al-Omair, Mohammed A.; Sayed, Abdelwahed R.; Youssef, Magdy M. [Molecules, 2015, vol. 20, # 2, p. 2591 - 2610]

63
[ 120-72-9 ]
[ 614-65-3 ]
[ 33948-97-9 ]

Yield	Reaction Conditions	Operation in experiment
93%	With Fe⁺³-montmorillonite K₁₀ for 0.025h;	General procedure for the preparation of diindolylmethanes. General procedure: Into a mortar, substituted benzaldehyde 1(1 mmol) or substituted hydrazone 4 (1 mmol), indole2 (2 mmol, 0.28 g), and Fe+3-montmorillonite K10(0.1 g) were added. The mixture was pulverized with apestle and entered a spontaneous reaction. Theprogress of a reaction was monitored by thin-layer chromatography (TLC) using EtOAc: petroleum ether(2 : 1) as eluent. The conditions of the reaction aregiven in Table 2. After the reaction was complete, theproduct was extracted with CHCl3 (3 × 10 mL) andinsoluble catalyst was removed by filtration. Theresulting crude material was purified by recrystallizationfrom EtOH to obtain pure products. Allsynthesized compounds are unknown and were characterizedby their physical constants, comparison withauthentic samples, IR, 1H NMR, and 13C NMR spectroscopies,and by elemental analysis.3,3'-[(Phenyl)methylene]bis(1H-indole) (3a). mp122-123°C, IR spectrum (KBr), ν, cm-1: 3396, 3049,2867, 1602, 1537, 1450, 1338. 1H NMR spectrum(400 MHz, CDCl3), δH, ppm: 5.93 s (1H), 6.73 s (2H),7.10-7.37 m (12H), 7.57-7.60 m (1H), 7.95 br.s (2H).13C NMR spectrum (100 MHz, CDCl3), δC, ppm: 33.7,112.1, 112.9, 116.7, 118.9, 122.2, 125.6, 127.3, 127.8,129.6, 132.8, 139.0, 146.7.

Reference： [1]Fekri; Nikpassand; Kohansal [Russian Journal of General Chemistry, 2015, vol. 85, # 12, p. 2861 - 2866][Zh. Obshch. Khim., 2015, vol. 85, # 12, p. 2861 - 2866,6]

64
[ 41756-81-4 ]
[ 614-65-3 ]
[ruthenium(III)chloride(triphenylphosphine)2(2-((2-phenylhydrazono)methyl)phenol)] [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
66%	In methanol for 10 - 12h; Reflux;	Synthesis of complex 1 Solid [Ru(PPh3)3Cl2] (0.096 g, 0.10 mmol) was added directly to a hot methanol solution (30 ml) of L1H2 (0.025 g, 0.12 mmol). The reaction mixture was refluxed for 10-12 h. The resulting yellowish brown crystalline complex 1, [Ru(L1)(PPh3)2Cl], was collected by filtration at room temperature after 2-3 days and then washed with cold methanol and diethyl ether. Yield: 0.057 g (66 %). Anal. Calcd. for C49H40ClN2OP2Ru (871.13): C, 67.5; H, 4.6; N, 3.2. Found: C, 67.4; H, 4.5; N, 3.1 %. IR (KBr disk,cm-1): 1605 (νC=N)s, 1428 s, 1297w, 1090 s, 742 m, 695 s, 518 s (νPPh3) cm-1. UV-Vis (CH2Cl2; λmax, nm (ε,M-1 cm-1)): 375 (1050), 295 (8210).

Reference： [1]Ghosh, Kaushik; Kumar, Rajan; Kumar, Sushil; Bala, Manju; Singh, Udai P. [Transition Metal Chemistry, 2015, vol. 40, # 8, p. 831 - 837]

65
[ 762-21-0 ]
[ 614-65-3 ]
ethyl 4-oxo-2-phenyl-2,4-dihydrochromeno[4,3-c]pyrazole-3-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
64%	With lanthanum(lll) triflate In neat (no solvent) at 130℃; for 7h;

Reference： [1]Hariprasad, Kurma Siva; Prasad, Kasagani Veera; Raju, Bhimapaka China [RSC Advances, 2016, vol. 6, # 110, p. 108654 - 108661]

66
[ 80306-63-4 ]
[ 614-65-3 ]
[ 1338214-83-7 ]

Yield	Reaction Conditions	Operation in experiment
65%	With lanthanum(lll) triflate In neat (no solvent) at 130℃; for 7h;

Reference： [1]Hariprasad, Kurma Siva; Prasad, Kasagani Veera; Raju, Bhimapaka China [RSC Advances, 2016, vol. 6, # 110, p. 108654 - 108661]

67
[ 623-47-2 ]
[ 614-65-3 ]
2-phenyl[1]benzopyrano[4,3-c]pyrazol-4(2H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
68%	With lanthanum(lll) triflate In neat (no solvent) at 130℃; for 8h;

Reference： [1]Hariprasad, Kurma Siva; Prasad, Kasagani Veera; Raju, Bhimapaka China [RSC Advances, 2016, vol. 6, # 110, p. 108654 - 108661]

68
[ 638-07-3 ]
[ 614-65-3 ]
[ 86100-07-4 ]

Yield	Reaction Conditions	Operation in experiment
67%	With lanthanum(lll) triflate In neat (no solvent) at 130℃;

Reference： [1]Hariprasad, Kurma Siva; Prasad, Kasagani Veera; Raju, Bhimapaka China [RSC Advances, 2016, vol. 6, # 110, p. 108654 - 108661]

69
[ 609-15-4 ]
[ 614-65-3 ]
[ 86100-07-4 ]

Yield	Reaction Conditions	Operation in experiment
	With lanthanum(lll) triflate In neat (no solvent) at 130℃;

Reference： [1]Hariprasad, Kurma Siva; Prasad, Kasagani Veera; Raju, Bhimapaka China [RSC Advances, 2016, vol. 6, # 110, p. 108654 - 108661]

70
[ 22502-03-0 ]
[ 614-65-3 ]
[ 86100-07-4 ]

Reference： [1]RSC Advances,2016,vol. 6,p. 108654 - 108661

71
[ 4341-76-8 ]
[ 614-65-3 ]
[ 86100-07-4 ]

Yield	Reaction Conditions	Operation in experiment
65%	With lanthanum(lll) triflate In neat (no solvent) at 130℃; for 8h;

Reference： [1]Hariprasad, Kurma Siva; Prasad, Kasagani Veera; Raju, Bhimapaka China [RSC Advances, 2016, vol. 6, # 110, p. 108654 - 108661]

72
[ 2216-94-6 ]
[ 614-65-3 ]
2,3-diphenyl[1]benzopyrano[4,3-c]pyrazol-4[2H]-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
67%	With lanthanum(lll) triflate In neat (no solvent) at 130℃; for 8h;

Reference： [1]Hariprasad, Kurma Siva; Prasad, Kasagani Veera; Raju, Bhimapaka China [RSC Advances, 2016, vol. 6, # 110, p. 108654 - 108661]

73
[ 614-65-3 ]
[ 90-02-8 ]

Yield	Reaction Conditions	Operation in experiment
78%	With citric acid In water for 0.133333h; Microwave irradiation; Green chemistry;	General procedure for the deprotection ofCarbonylcompounds from phenylhydrazones,semicarbazones, and oximes General procedure: A mixture of 0.2 mmol phenylhydrazone,semicarbazones or oximes and citric acid(0.2 mmol) were mixed together in water (10 mL)was introduced in a 50 mL Erlenmeyer ask and wasplaced in a commercial microwave oven operatingat a power output of 300 W and irradiated for theappropriate time in 30 seconds intervals each.(Table 3). The reaction was monitored by TLC.The product extracted with Chloroform, dried overanhydrous Na2SO4, flter and was chromatographed on silica gel (eluted by ethyl acetate: hexane 2:8)to afford the corresponding products in good toexcellent yields (Table 3). All the products werecharacterized by their physical constants, IR, NMRspectra and comparison with authentic samples.The phenylhydrazones, semicarbazones and oximeswere prepared by standard procedures32.

Reference： [1]Abd El Rahman, Naglaa M.; Nasreen, Aayesha [Oriental Journal of Chemistry, 2017, vol. 33, # 4, p. 2030 - 2035]

74
[ 1619-75-6 ]
[ 614-65-3 ]
C₂₆H₂₄N₂O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
68%	With 1,4-diaza-bicyclo[2.2.2]octane In dichloromethane at 40℃; for 21h; Sealed tube; diastereoselective reaction;

Reference： [1]Gurubrahamam, Ramani; Nagaraju, Koppanathi; Chen, Kwunmin [Chemical Communications, 2018, vol. 54, # 47, p. 6048 - 6051]

75
[ 298-06-6 ]
[ 614-65-3 ]
2-ethoxy-3-phenyl-2-sulfido-2,3-dihydro-1,3,4,2-benzoxadiazaphosphepine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
55%	In ethanol for 8h; Reflux;	Synthesis of 2-ethoxy-3-phenyl-2-sulfido-2,3-dihydro-1,3,4,2-benzoxadiazaphosphepine (6) A solution of phosphorus decasulfide (2.22 g, 5 mmol) in ethanol (30 ml) was heated under reflux for 1 hour to give O,O-diethyldithiophosphoric acid in situ. Compound 1 (0.53 g, 2.5 mmol) was added to the previous ethanolic solution. The mixture was heated under reflux for 8 hours. The reaction mixture was concentrated into its half volume and left to cool. The formed solid after adding some water, was filtered off and recrystallized from diluted ethanol to give yellow solid in 55% yield; mp 178-180 oC. IR (KBr), (nmax, cm-1): 3030 (C-Harom), 2927 (C-Haliph), 1602 (C=N), 1565 (C=C), 1067 (P-O-C), 693 (P=S). 1H-NMR (400 MHz, DMSO-d6): 1.03 (t, 3H, J=6.8 Hz, CH3), 4.01 (q, 2H, J=6.8 Hz, OCH2), 7.35-7.41(m, 3H, Ph-H), 7.49-7.55 (m, 4H, Ph-H), 7.79 (t, 1H, J=7.2 Hz, Ph-H), 7.97 (d, 1H, J=8.0 Hz, Ph-H), 9.62 (s, 1H, CH=N).13C-NMR (100 MHz, DMSO-d6): 14.3 (CH3), 59.6 (CH2), 115.1 (C-2`,6`), 116.7 (C-9), 118.8 (C-5a), 120.1 (C-4`), 122.3 (C-7), 129.6 (C-3`,5`), 130.8 (C-6), 138.5 (C-8), 141.5 (C-1`), 145.9 (C-5), 160.4 (C-9a). MS (EI, m/z): 318 (M+,27%). Anal. calcd. for C15H15N2O2PS (318.34): C, 56.60; H, 4.75; N, 8.80; S, 10.07%. Found: C, 56.28; H, 3.61; N, 8.59; S, 9.69%.

Reference： [1]Ali, Tarik E.; Assiri, Mohammed A.; Yahia [Synthetic Communications, 2018, vol. 48, # 14, p. 1828 - 1837]

76
[ 19172-47-5 ]
[ 614-65-3 ]
2-(4-methoxyphenyl)-3-phenyl-2-sulfido-2,3-dihydro-1,3,4,2-benzoxadiaza-phosphepine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	In toluene for 8h; Reflux;	Synthesis of 2-(4-methoxyphenyl)-3-phenyl-2-sulfido-2,3-dihydro-1,3,4,2-benzoxadiaza-phosphepine (7) Lawesson's reagent (0.5 g, 1.25 mmol) was added to a solution of compound 1 (0.26 g, 1.25 mmol) in toluene (30 ml). The mixture was heated under reflux for 8 hours. The solution was concentrated to its half volume and left to cool. The obtained solid was filtered off and recrystallized from toluene to give canary yellow solid in 75% yield; mp 184-186 oC. IR (KBr), (nmax, cm-1): 3079 (C-Harom), 2981 (C-Haliph), 1617 (C=N), 1514 (C=C), 1044 (O-C), 765 (P=S). 1H-NMR (400 MHz, DMSO-d6): 3.74 (s, 3H, OCH3), 7.30 (d, 1H, J=6.8 Hz, Ar-H), 7.39 (t, 2H, J=7.2 Hz, Ph-H and Ar-H), 7.45-7.49 (m, 2H, Ph-H), 7.65-7.76 (m, 5H, Ph-H), 7.92 (d, 1H, J=8.0 Hz, Ph-H), 8.07 (d, 2H, J=8.0 Hz, Ar-H), 9.00 (s, 1H, CH=N). 13C-NMR (100 MHz, DMSO-d6): 55.6 (OCH3), 116.2 (C-9), 116.6 (C-2`,6`), 119.1 (C-5a), 120.3 (C-3``,5``), 121.3 (C-4`), 122.0 (C-7), 128.2 (C-2``,6``), 129.1 (C-3`,5`), 130.7 (d, JPC=105 Hz, C-1``), 134.6 (C-6`), 135.5 (C-8), 146.4 (C-1`), 147.9 (C-5), 157.1 (C-4``), 157.8 (C-9a). 31P-NMR (162 MHz, DMSO-d6): 57.2 ppm. MS (EI, m/z): 380 (M+, 67%). Anal. calcd. for C20H17N2O2PS (380.41): C, 63.15; H, 4.50; N, 7.36; S, 8.43%. Found: C, 62.95; H, 4.19; N, 7.02; S, 8.07%.

Reference： [1]Ali, Tarik E.; Assiri, Mohammed A.; Yahia [Synthetic Communications, 2018, vol. 48, # 14, p. 1828 - 1837]

77
[ 78-40-0 ]
[ 614-65-3 ]
2-ethoxy-3-phenyl-2-oxido-2,3-dihydro-1,3,4,2-benzoxadiazaphosphepine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
53%	With 1,8-diazabicyclo[5.4.0]undec-7-ene for 10h; Heating;	Synthesis of 2-ethoxy-3-phenyl-2-oxido-2,3-dihydro-1,3,4,2-benzoxadiazaphosphepine (8) A mixture of triethyl phosphate (0.85 ml, 5 mmol) and compound 1 (0.53 g, 2.5 mmol) in the presence of a few drops of DBU, was fused on water bath for 10 hours. The oily product was dissolved in hot methanol and left to cool. The formed solid was filtered off and dried to give pale brown solid in 53% yield; mp 146-148 oC. IR (KBr), (nmax, cm-1): 3050 (C-Harom), 2976 (C-Haliph), 1600 (C=N), 1560, 1510 (C=C), 1202 (P=O), 1047 (P-O-C). 1H-NMR (400 MHz, DMSO-d6): 1.03 (t, 3H, J=6.8 Hz, CH3), 3.41 (q, 2H, J=6.8 Hz, OCH2), 7.21 (d, 1H, J=8.4 Hz, Ph-H), 7.51-7.58 (m, 4H, Ph-H), 7.82 (t, 2H, J=8.0 Hz, Ph-H), 8.01 (d, 2H, J=8.0 Hz, Ph-H), 8.72 (s, 1H, CH=N). 13C-NMR (100 MHz, DMSO-d6): 16.5 (CH3), 61.1 (CH2), 112.2 (C-2`,6`), 117.3 (C-9), 119.2 (C-5a), 120.2 (C-4`), 121.5 (C-7), 129.1 (C-3`,5`), 130.8 (C-6), 136.6 (C- 8), 141.4 (C-1`), 145.9 (C-5), 159.3 (C-9a). MS (EI, m/z): 302 (M+, 24%). Anal. calcd. for C15H15N2O3P (302.27): C, 59.60; H, 5.00; N, 9.27%. Found: C, 59.31; H, 4.72; N, 8.97%.

Reference： [1]Ali, Tarik E.; Assiri, Mohammed A.; Yahia [Synthetic Communications, 2018, vol. 48, # 14, p. 1828 - 1837]

78
[ 762-04-9 ]
[ 614-65-3 ]
1-(2-ethoxy-2-oxido-2,3-dihydro-1,2-benzoxaphosphol-3-yl)-2-phenylhydrazine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
69%	With 1,8-diazabicyclo[5.4.0]undec-7-ene for 6h; Heating;	Synthesis of 1-(2-ethoxy-2-oxido-2,3-dihydro-1,2-benzoxaphosphol-3-yl)-2-phenylhydrazine (9) A mixture of diethyl phosphite (0.7 ml, 5 mmol) and compound 1 (0.53 g, 2.5 mmol) in the presence of a few drops of DBU, was fused on water bath for 6 hours. The oily product was dissolved in hot diluted ethanol and left to cool. The formed solid was filtered off and dried to give yellow solid in 69% yield; mp 101-103 oC. IR (KBr), (nmax, cm-1): 3415, 3162 (2 NH), 3049 (C-Harom), 2950, 2886 (C-Haliph), 1614, 1573 (C=C), 1230 (P=O), 1083 (P-O-C). 1H-NMR (400 MHz, DMSO-d6): 0.77 (t, 3H, J=6.8 Hz, CH3), 3.95 (q, 2H, J=6.8 Hz, OCH2), 4.68 (s, 1H, NH exchangeable with D2O), 5.32 (d, 1H, J=15.2 Hz, P-CH), 6.77 (t, 1H, J=7.2 Hz, Ph-H), 6.86-6.89 (m, 2H, Ph-H), 7.04 (d, 1H, J=8.0 Hz, Ph-H), 7.17 (d, 1H, J=7.6 Hz, Ph-H), 7.22-7.24 (m, 3H, Ph-H), 7.28-7.31 (m, 1H, Ph-H), 9.08 (brs, 1H, NH exchangeable with D2O). 13C-NMR (100 MHz, DMSO-d6): 17.2 (CH3), 59.6 (CH2), 48.5 (d, JPC=148 Hz), 116.9 (C-2`,6`), 117.7 (C-7), 118.7 (C-3a), 119.7 (C-4`), 121.45 (C-5), 129.2 (C-3`,5`), 131.6 (C-4), 134.1 (C-6), 139.6 (C-1`), 157.2 (C-7a). 31P-NMR (162 MHz, DMSO-d6): 19.7 ppm. MS (EI, m/z): 304 (M+, 35%). Anal. calcd. for C15H17N2O3P (304.29): C, 59.21; H, 5.63; N, 9.21%. Found: C, 58.91; H, 5.39; N, 9.01%.

Reference： [1]Ali, Tarik E.; Assiri, Mohammed A.; Yahia [Synthetic Communications, 2018, vol. 48, # 14, p. 1828 - 1837]

79
[ 140-08-9 ]
[ 614-65-3 ]
2,3-dihydro[1,2]benzoxaphospholo[2,3-b][1,4,2]oxazaphosphinine 5-oxide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
48%	With 1,8-diazabicyclo[5.4.0]undec-7-ene In water for 10h;	Synthesis of 2,3-dihydro[1,2]benzoxaphospholo[2,3-b][1,4,2]oxazaphosphinine 5-oxide (10) A mixture of tris(2-chloroethyl)phosphite (0.7 mL, 3 mmol) and compound 1 (0.53 g, 2.5 mmol) in presence of a few drops of DBU as a catalyst, were allowed to react on a water bath for 10 h (0.15 mL of distilled water added after 3 h). The reaction mixture was treated with cold water to give the solid which was filtered off and recrystallized from dilute ethanol to yield a beige solid in 48% yield; mp 228-230°C (dec.). IR (KBr), (nmax, cm-1): 3064 (C-Harom), 2974, 2922(C-Haliph), 1628 (C=N), 1600 (C=C), 1291 (P=O), 1044 (P-O-C). 1H-NMR (400 MHz, DMSO-d6): 3.80 (s, 2H, NCH2), 4.17 (s, 2H, OCH2), 6.81-6.97 (m, 2H, Ph-H), 7.38 (t, 1H, J=8.4 Hz, Ph-H), 7.68 (d, 1H, J=8.0 Hz, Ph-H). 13C-NMR (100 MHz, DMSO-d6): 55.7 (NCH2), 60.6 (OCH2), 117.9 (C-7), 119.4 (C-10a), 121.1 (C-9), 125.6 (C-10), 135.3 (C-8), 146.1 (d, JPC=94 Hz, C-10b), 157.1 (C-6a). MS (EI, m/z): 209 (M+, 3%). Anal. calcd. for C9H8NO3P (209.14): C, 51.69; H, 3.86; N, 6.70%. Found: C, 51.31; H, 3.52; N, 6.43%.

Reference： [1]Ali, Tarik E.; Assiri, Mohammed A.; Yahia [Synthetic Communications, 2018, vol. 48, # 14, p. 1828 - 1837]

80
[ 867-13-0 ]
[ 614-65-3 ]
3-ethoxy-3-oxido-2-phenyl-2,3-dihydrochromeno[3,4-d][1,2,3]diazaphosphol-4(1H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
72%	With 1,8-diazabicyclo[5.4.0]undec-7-ene In ethanol for 10h; Reflux; regioselective reaction;	Synthesis of 3-ethoxy-3-oxido-2-phenyl-2,3-dihydrochromeno[3,4-d][1,2,3]diazaphosphol-4(1H)-one (12) A mixture of compound 1 (0.53 g, 2.5 mmol) and diethyl ethoxycarbonyl phosphonate (0.56 ml, 2.5 mmol) in ethanol containg a few drops of DBU, was heated under reflux for 10 hours. The solid formed was filtered off, washed with water then cooled ethanol and crystallized from DMF/EtOH to give pale brown solid in 72% yield; mp >300 oC. IR (KBr), (nmax, cm-1): 3270 (NH), 3030 (C-Harom), 1733 (C=O), 1622, 1601 (C=C), 1250 (P=O), 1032 (O-C). 1H-NMR (400 MHz, DMSO-d6): 1.29 (t, 3H, J=6.8 Hz, CH3), 4.34 (q, 2H, J=6.8 Hz, OCH2), 7.36 (t, 1H, J=6.8 Hz, Ph-H), 7.59-7.63 (m, 3H, Ph-H), 7.68-7.75 (m, 3H, Ph-H), 7.89 (d, 2H, J=7.0 Hz, Ph-H), 9.21 (s, 1H, NH exchangeable with D2O). 13C-NMR (100 MHz, DMSO-d6): 15.8 (CH3), 60.0 (OCH2), 116.9 (C-2`,6`), 117.8 (C-6), 118.1 (C-9a), 120.8 (C-4`), 122.9 (C-8), 125.9 (d, JPC=86 Hz, C-3a), 127.9 (C-9), 130.0 (C-3`,5`), 135.2 (C-7), 141.0 (C-9b), 143.7 (C-1`), 156.5 (C-5a), 175.1 (C-4). 31P-NMR (162 MHz, DMSO-d6): 25.3 ppm. MS (EI, m/z): 342 (M+,13 %). Anal. calcd. for C17H15N2O4P (342.29): C, 59.65; H, 4.42; N, 8.18. Found: C, 59.29; H, 4.03; N, 7.89%.

Reference： [1]Ali, Tarik E.; Assiri, Mohammed A.; Yahia [Synthetic Communications, 2018, vol. 48, # 14, p. 1828 - 1837]

81
[ 614-65-3 ]
3-phenyl-2,3-dihydro-1,3,4,2-benzoxadiazaphosphepine 2-oxide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73%	With phosphorus tribromide; triethylamine In toluene for 10.5h; Reflux;	General procedure for reaction of compound 1 with phosphorus oxychloride and phosphorus tribromide: Sythesis of products 3 and 4. General procedure: A solution of phosphorus oxychloride or phosphorus tribromide (2.5 mmol) in toluene (5 ml), was added dropwise to a solution of compound 1 (0.53 g, 5 mmol) in toluene (60 ml) in resence of a catalytic amount of triethylamine (0.7 ml, 10 mmol) at 5-10 oC for 30 minutes. The mixtures were heated under reflux for 10 hours. The reaction mixtures were concentrated into their third volume and left to cool. The obtained oily products were dissolved in distilled water (15 ml). The formed solids were filtered off and crystallized from methanol to give pale green solids 3 and 4, respectively.

Reference： [1]Ali, Tarik E.; Assiri, Mohammed A.; Yahia [Synthetic Communications, 2018, vol. 48, # 14, p. 1828 - 1837]

82
[ 614-65-3 ]
3-phenyl-2-sulfanyl-2-sulfido-2,3-dihydro-1,3,4,2-benzoxadiazaphosphepine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
63%	With tetraphosphorus decasulfide In toluene for 5h; Reflux;	Synthesis of 3-phenyl-2-sulfanyl-2-sulfido-2,3-dihydro-1,3,4,2-benzoxadiazaphosphepine (5) A mixture of phosphorus decasulfide (1.11 g, 2.5 mmol) and compound 1 (0.53 g, 2.5 mmol) in toluene (40 ml), was heated under reflux for 5 hours. The formed solid on heating was filtered off and recrystallized from ethanol to give orange solid in 63% yield; mp 95-97 oC. IR (KBr), (nmax, cm-1): 3058 (C-Harom), 2610 (SH), 1600 (C=N), 1544, 1503 (C=C), 1059 (O-C), 691 (P=S). 1H-NMR (400 MHz, DMSO-d6): 3.33 (br, 1H, SH exchangeable with D2O), 6.66-6.89 (m, 1H, Ph-H), 7.16-8.00 (m, 8H, Ph-H), 8.95 (s, 1H, CH=N). MS (EI, m/z): 306 (M+, 69%). Anal. calcd. for C13H11N2OPS2 (306.35): C, 50.97; H, 3.62; N, 9.14; S, 20.93%. Found: C, 50.72; H, 3.11; N, 8.95; S, 20.59%.

Reference： [1]Ali, Tarik E.; Assiri, Mohammed A.; Yahia [Synthetic Communications, 2018, vol. 48, # 14, p. 1828 - 1837]

83
[ 614-65-3 ]
3-phenyl-2-hydroxy-2-oxido-2,3-dihydro-1,3,4,2-benzoxadiazaphosphepine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60%	With triethylamine; trichlorophosphate In toluene for 10.5h; Reflux;	General procedure for reaction of compound 1 with phosphorus oxychloride and phosphorus tribromide: Sythesis of products 3 and 4. General procedure: A solution of phosphorus oxychloride or phosphorus tribromide (2.5 mmol) in toluene (5 ml), was added dropwise to a solution of compound 1 (0.53 g, 5 mmol) in toluene (60 ml) in resence of a catalytic amount of triethylamine (0.7 ml, 10 mmol) at 5-10 oC for 30 minutes. The mixtures were heated under reflux for 10 hours. The reaction mixtures were concentrated into their third volume and left to cool. The obtained oily products were dissolved in distilled water (15 ml). The formed solids were filtered off and crystallized from methanol to give pale green solids 3 and 4, respectively. 3-Phenyl-2-hydroxy-2-oxido-2,3-dihydro-1,3,4,2-benzoxadiazaphosphepine (3): 60% yield; mp >300 oC. IR (KBr), (nmax, cm-1): 3227 (br, OH), 1604 (C=N), 1581, 1510 (C=C), 1220 (P=O). 1H-NMR (400 MHz, DMSO-d6): 3.55 (s, 1H, OH exchangeable with D2O), 6.92-7.02 (m, 4H, Ph-H), 7.36-7.54 (m, 4H, Ph-H), 7.67 (d, 1H, J=7.6 Hz, Ph-H), 8.96 (s, 1H, CH=N). 13C-NMR (100 MHz, DMSO-d6): 112.2 (C-2`,6`), 115.1 (C-9), 117.9 (C-5a), 121.4 (C-4`), 122.9 (C-7), 129.7 (C-3`,5`), 130.2 (C-6), 133.3 (C-8), 142.0 (C-1`), 146.5 (C-5), 158.1 (C-9a). MS (EI, m/z): 274 (M+, 9%). Anal. calcd. for C13H11N2O3P (274.22): C, 56.94; H, 4.04; N, 10.22%. Found: C, 56.65; H, 3.76; N, 9.86%.

Reference： [1]Ali, Tarik E.; Assiri, Mohammed A.; Yahia [Synthetic Communications, 2018, vol. 48, # 14, p. 1828 - 1837]

84
[ 824-72-6 ]
[ 614-65-3 ]
2,3-diphenyl-2-oxido-2,3-dihydro-1,3,4,2-benzoxadiazaphosphepine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%	With triethylamine In toluene for 10.5h; Reflux;	Synthesis of 2,3-diphenyl-2-oxido-2,3-dihydro-1,3,4,2-benzoxadiazaphosphepine (2) A solution of phenylphosphonic dichloride (0.35 ml, 2.5 mmol) in toluene (5 ml) wasadded dropwise to a solution of compound 1 (0.53 g, 2.5 mmol) in toluene (30 ml) inthe presence of a catalytic amount of triethylamine (0.35 ml, 5 mmol) at 5-10 C for30 min. The mixture was heated under reflux for 10 h. The formed solid was filtered off,washed with water several times and crystallized from diluted dioxane to give pale greensolid in 78% yield; mp 236-238 C. IR (KBr), (max, cm1): 3098 (C-Harom), 1609(CN), 1530 (CC), 1199 (PO), 1089 (O-C). 1H NMR (400 MHz, DMSO-d6):7.52-7.59 (m, 4H, Ph-H), 7.74 (d, 3H, J5.2 Hz, Ph-H), 7.85-7.90 (m, 3H, Ph-H),8.12-8.21 (m, 4H, Ph-H), 8.91 (s, 1H, CHN). 13C NMR (100 MHz, DMSO-d6): 116.7 (C-20,60), 118.2 (C-9), 119.4 (C-5a), 120.4 (C-40), 121.8 (C-7), 124.0 (C-300,500), 127.8(C-200,600), 129.6 (C-30,50), 130.9 (C-6), 132.3 (C-400), 136.8 (C-8), 140.0 (d,JPC125 Hz, C-100), 142.3 (C-10), 147.0 (C-5), 159.6 (C-9a). 31P NMR (162 MHz,DMSO-d6): 35.7 ppm. MS (EI, m/z): 334 (M, 6%). Anal. calcd. for C19H15N2O2P(334.32): C, 68.26%; H, 4.52%; N, 8.38%. Found: C, 67.91%; H, 4.25%; N, 8.02%.

Reference： [1]Ali, Tarik E.; Assiri, Mohammed A.; Yahia [Synthetic Communications, 2018, vol. 48, # 14, p. 1828 - 1837]

85
[ 614-65-3 ]
C₁₃H₉Br₃N₂O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With bromine; acetic acid

Reference： [1]Arjuna, Anania; Kaur, Manpreet; Singh, Baldev [Journal of Heterocyclic Chemistry, 2019]

86
[ 614-65-3 ]
2',4'-dibromophenyl-5-cyclohexyl-3-(2''-hydroxyphenyl)-3a,4,6,6a-tetrahydro-1H,5H-pyrrolo[3,4-c]pyrazole-4,6-dioneyrazole-4,6-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: bromine; acetic acid 2: copper(II) nitrate / water / 1.5 h / Inert atmosphere; Heating; Green chemistry

Reference： [1]Arjuna, Anania; Kaur, Manpreet; Singh, Baldev [Journal of Heterocyclic Chemistry, 2019]

87
[ 22472-11-3 ]
[ 614-65-3 ]

Yield	Reaction Conditions	Operation in experiment
	With dihydrogen peroxide In N,N-dimethyl-formamide at 25℃; for 0.5h;

Reference： [1]Aguiar, Sandra I.; André, Ana S.; António, João P. M.; Bernardes, Gonçalo J. L.; Carvalho, Joana Inês; Dias, Joana N. R.; Faustino, Hélio; Gois, Pedro M. P.; Lopes, Ricardo M. R. M.; Veiros, Luis F.; da Silva, Frederico A. [Angewandte Chemie - International Edition, 2021, vol. 60, # 49, p. 25914 - 25921][Angew. Chem., 2021, vol. 133, # 49, p. 26118 - 26125]

88
[ 40138-16-7 ]
[ 100-63-0 ]
[ 614-65-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: water / 20 °C 2: dihydrogen peroxide / N,N-dimethyl-formamide / 0.5 h / 25 °C / pH 7.4

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P321
P322
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P378
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P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
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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.
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P401
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H200	Unstable explosive
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H231	May react explosively even in the absence of air at elevated pressure and/or temperature
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H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
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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
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H290	May be corrosive to metals
Health hazards
Code	Phrase
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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
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H351	Suspected of causing cancer
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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. 614-65-3 ] {[proInfo.proName]}

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[ 614-65-3 ] Synthesis Path-Upstream 1~1

[ 614-65-3 ] Synthesis Path-Downstream 1~88

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Aryls

Hydrazones

Amines

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[ 614-65-3 ]