Name: 1038-95-5|Tri-p-tolylphosphine|98%
Brand: Ambeed
SKU: A151967
Price: 5.0 USD
Availability: InStock
Rating: 95 (25 reviews)

1
[ 1038-95-5 ]
[ 807-19-2 ]

Yield	Reaction Conditions	Operation in experiment
34%	With pyridine; potassium permanganate In water at 100℃; for 48h;	2.1 (1) Ligand [4,4’,4”-tricarboxyphenyl] phosphineOxide (Hereinafier TCPO) The synthesis was performed at a half scale of the published data (J. Vaclavik, M Servalli et al, Chem Cat Chem 2013, 5, 692-696). In a 100-mE pear-shaped evaporating flask, tri(p-toryl)phosphine (1 g, 3.2 mmol) was dispersed in pyridine (12 mE)/distilled water (24 mE). While heating the dispersion, KMnO4 (10 g, 63.3 mmol) was added in four portions and refluxed under heating at 100° C. for 48 hours. Afier 48 hours, the reaction solution was filtered through a filter paper and the precipitate was washed with warm watet When 10 M H2504 was added to the obtained filtered liquid, a white precipitate was obtained. The precipitate was dissolved in 2 M NaOH and the aqueous solution was extracted with THF and EtOAc. To the obtained aqueous layer was again added 10 M H2504 and the generated white precipitate was recovered by suction filtration. The obtained precipitate was dried under vacuum to give white powder. Yield: 0.433 g (34%). ‘H NMR (400 MHz, DMSO, TMS): ö8.12-8.08 (dd, 6H), ö7.88-7.75 (dd, 6H). IR(ATR): 1692, 1395, 1246, 1162, 1102, 1016, 857 cm’.
	With chromic acid; acetic acid at 40 - 50℃;
	With potassium permanganate; sodium carbonate In water at 120℃; for 5h;	2.1. Synthesis of tris(4-(benzo[d]thiazol-2-yl)phenyl)phosphine oxide (4-TBTPO) General procedure: 4,4,4-Phosphoryltribenzoic acid (TCPO) was firstly prepared from oxidation of tri(ptolyl)phosphine by potassium permanganate. Tri(p-tolyl)phosphine (0.3 g, 1.0 mmol), sodium carbonate (0.24 g, 3.0 mmol) and potassium permanganate (0.47 g, 3.0 mmol) were added to water (30mL). The mixture was heated at 120°C for 5 h with reflux condenser. After filtering the reaction mixture, dilute aq. HCl was slowly added to the filtrate. The precipitates were recrystallized from methanol. The structure of TCPO could be simply confirmed by spectroscopic methods. Then TCPO (0.42 g, 1mmol), triphenyl phosphite (0.78mL, 3mmol), tetrabutylammonium bromide (0.96 g, 3mmol), 2-aminothiophenol (0.32 mL, 3 mmol) were added to flask with reflux condenser and heated at 120°C for 3h. The progress of reaction was monitored by TLC. After the completion of reaction, the product was precipitated from the solution by adding methanol and filtered. Then the product was dissolved in CHCl3, added anhydrous MgSO4, and stirred at room temperature for 4 h. Filtered and evaporated the solvents to get a yellow solid.

With potassium permanganate; sodium carbonate In water at 120℃; for 5h;

1 A mixed solution of tri (p-tolyl) phosphine (0.3g, 1.0mmol), sodium carbonate (0.24g, 3.0mmol) and potassiumpermanganate (0.47g, 3.0mmol) in 30mL aqueous solution was added to reflux condenser Condenser, and the mixture was heated at 120 DEG C for 5 hours. Then, after filtering the reaction mixture, a dilute hydrochloric acid aqueous solution was added to the filtered mixture, and TCPO as a precipitate was recovered.

Reference： [1]Current Patent Assignee: HOKKAIDO UNIVERSITY - US2018/334472, 2018, A1 Location in patent: Paragraph 0140; 0141; 0142; 0143
[2]Michaelis [Justus Liebigs Annalen der Chemie, 1901, vol. 315, p. 91]
[3]Jo, Hyeonhee; Kim, Kyeonghyeon; Kim, Dong-Eun; Shin, Hoon-Kyu; Lee, Burm-Jong [Molecular Crystals and Liquid Crystals, 2016, vol. 636, # 1, p. 60 - 66]
[4]Current Patent Assignee: INJE UNIVERSITY - KR2017/36453, 2017, A Location in patent: Paragraph 0024-0025

2
[ 1038-95-5 ]
[ 797-70-6 ]

Yield	Reaction Conditions	Operation in experiment
100%	With gold(III) complex supported on cellulose extracted from Carthamus tinctorius immobilized on nanofibrous phosphosilicate; air at 20℃; for 1h; Irradiation;
100%	With 4-phenylthioxanthone In methanol at 20℃; for 1h; Irradiation;	Tris(4-methoxyphenyl)phosphine oxide (2a) General procedure: 1a (70.5 mg, 0.20 mmol), 4-phenylthioxanthone (3 mg, 0.01 mmol), CH3OH (30 mL) were added to a pyrex reaction flash which was equipped with a magnetic stirrer. The mixture was irradiated by a 23 W household lamp at rt under air atmosphere. The photoreaction was completed after 40 minutes as monitored by TLC (eluent: petroleum ether). The solvent was removed and the residue was purified by flash column chromatography on silica gel (eluent: petroleum ether/ethyl acetate = 10/1→EA) to afford 2a as a solid (74 mg, 100%); 1H NMR (400 MHz, CDCl3) δ 7.56 (dd, J = 11.6, 8.8 Hz, 6 H), 6.95 (dd, J = 8.8, 2.0 Hz, 6 H), 3.83 (s, 9 H).
100%	With dihydrogen peroxide In dichloromethane at 20℃; for 0.166667h;

99%	Stage #1: Tri(p-tolyl)phosphine With dihydrogen peroxide In dichloromethane for 0.5h; Stage #2: In dichloromethane for 18h; Molecular sieve;
98%	With n-butyllithium; dinitrogen monoxide In hexane; toluene at 20℃; for 0.5h;
97%	With dihydrogen peroxide In dichloromethane for 3h;
96%	With sulfur trioxide In dichloromethane at 0℃;
93%	With dihydrogen peroxide In tetrahydrofuran; water at 20℃; for 2h;
89%	With dihydrogen peroxide In dichloromethane; water at 0℃; for 4h;
89%	With eosin In methanol; dichloromethane at 20℃; for 4h; Irradiation; Green chemistry;
	With perchloric acid; dihydrogen peroxide; methyltrioxorhenium(VII) In acetonitrile at 25℃;
	With sodium hydroxide; water; bromine ueber mehrere Stufen;
	With water; bromine 1) benzene, 5 min, 2) acetone; Yield given. Multistep reaction;
	With rhodamine 6G In water; acetonitrile at 25℃; Irradiation;
	With p-nitrostilbene dibromide In methanol; acetonitrile at 25℃;
	With air; biphenyl; 9,10-Dicyanoanthracene In acetonitrile UV-irradiation;
	With disodium hydrogenphosphate; 3-chloro-benzenecarboperoxoic acid In dichloromethane at 0℃; for 0.5h;
	With air; biphenyl; 9,10-Dicyanoanthracene In acetonitrile Irradiation;
	Multi-step reaction with 2 steps 1: benzene 2: (i) PhLi, Et₂O, (ii) Ph₂CO
	With air; triethyl borane In tetrahydrofuran; hexane at 20℃; for 0.333333h;
	With water In dichloromethane Laser flash photolysis;
	With p-methoxy-phenylazide at 21.84℃;
	With tris(4,4-dimethyl-2-oxazolinyl)phenylborato(ethylperoxy)zinc In benzene
	With dihydrogen peroxide In tetrahydrofuran; water at 20℃;
	With 3,6-bis(ethylamino)-9-[2-(methoxycarbonyl)phenyl]-xanthylium chloride In water; acetonitrile Irradiation;
	With dihydrogen peroxide In dichloromethane; water at 0 - 20℃;
	With [(N-benzyl-N,N′,N′-tris(2-pyridylmethyl)-1,2-diaminoethane)Mn^IV(O)]²⁺ In 2,2,2-trifluoroethanol; acetonitrile at -0.16℃;
	Multi-step reaction with 4 steps 1: toluene / 18 h / 20 °C 2: sodium hydroxide / water 3: sodium amide / toluene / 24 h / Inert atmosphere; Reflux 4: neat (no solvent) / 170 °C
	With mesitylenecarbonitrile oxide; triphenylphosphine In tetrahydrofuran at 20℃; for 0.25h; Inert atmosphere;
	With 2,6-dimethylpyridine; ferrocenium trifluoromethanesulfonate; water In acetonitrile at 20℃; for 3h; Schlenk technique; Inert atmosphere; Irradiation;
	With [(2-(N,N-bis(pyridin-2-yl)methyl)amino-(N-quinolin-8-yl)acetamidato)Mn^III(H₂O)](OTf)₂ In acetonitrile at 24.84℃;

Reference： [1]Sadeghzadeh, Seyed Mohsen; Zhiani, Rahele [RSC Advances, 2019, vol. 9, # 3, p. 1509 - 1516]
[2]Ding, Aishun; Li, Shijie; Chen, Yang; Jin, Ruiwen; Ye, Cong; Hu, Jianhua; Guo, Hao [Tetrahedron Letters, 2018, vol. 59, # 43, p. 3880 - 3883]
[3]Song, Jeong Hwa; Lee, Giseong; Yoon, Jung Heum; Jang, Junyeon; Choi, Doosan; Yun, Heejun; Kwon, Kangin; Kim, Hojin; Hong, Chang Seop; Kim, Youngki; Han, Hogyu; Lim, Kwang Soo; Lee, Woo Ram [Chemistry - A European Journal, 2020, vol. 26, # 51, p. 11767 - 11775]
[4]Arp, Fabian F.; Bhuvanesh, Nattamai; Blümel, Janet [Inorganic Chemistry, 2020, vol. 59, # 18, p. 13719 - 13732]
[5]Yamada, Tohru; Suzuki, Kyosuke; Hashimoto, Kentaro; Ikeno, Taketo [Chemistry Letters, 1999, # 10, p. 1043 - 1044]
[6]Yanagisawa, Kei; Kitagawa, Yuichi; Nakanishi, Takayuki; Akama, Tomoko; Kobayashi, Masato; Seki, Tomohiro; Fushimi, Koji; Ito, Hajime; Taketsugu, Tetsuya; Hasegawa, Yasuchika [European Journal of Inorganic Chemistry, 2017, vol. 2017, # 32, p. 3843 - 3848]
[7]Olah, George A.; Gupta, B. G. Balaram; Garcia-Luna, Armando; Narang, Subhash C. [Journal of Organic Chemistry, 1983, vol. 48, # 10, p. 1760 - 1762]
[8]Stepen, Arne J.; Bursch, Markus; Grimme, Stefan; Stephan, Douglas W.; Paradies, Jan [Angewandte Chemie - International Edition, 2018, vol. 57, # 46, p. 15253 - 15256][Angew. Chem., 2018, vol. 130, # 46, p. 15473 - 15476,4]
[9]Hasegawa, Yasuchika; Ohkubo, Tomoki; Nakanishi, Takayuki; Kobayashi, Atsushi; Kato, Masako; Seki, Tomohiro; Ito, Hajime; Fushimi, Koji [European Journal of Inorganic Chemistry, 2013, # 34, p. 5911 - 5918]
[10]Zhang, Yanbin; Ye, Cong; Li, Shijie; Ding, Aishun; Gu, Guangxin; Guo, Hao [RSC Advances, 2017, vol. 7, # 22, p. 13240 - 13243]
[11]Abu-Omar; Espenson [Journal of the American Chemical Society, 1995, vol. 117, # 1, p. 272 - 280]
[12]Michaelis [Justus Liebigs Annalen der Chemie, 1901, vol. 315, p. 91]
[13]Chou, Whe-Narn; Pomerantz, Martin [Journal of Organic Chemistry, 1991, vol. 56, # 8, p. 2762 - 2769]
[14]Yasui, Shinro; Tsujimoto, Munekazu; Itoh, Kenji; Ohno, Atsuyoshi [Journal of Organic Chemistry, 2000, vol. 65, # 15, p. 4715 - 4720]
[15]Yasui, Shinro [Heteroatom Chemistry, 2001, vol. 12, # 4, p. 217 - 222]
[16]Yasui, Shinro; Tojo, Sachiko; Majima, Tetsuro [Journal of Organic Chemistry, 2005, vol. 70, # 4, p. 1276 - 1280]
[17]Yamagiwa, Noriyuki; Tian, Jun; Matsunaga, Shigeki; Shibasaki, Masakatsu [Journal of the American Chemical Society, 2005, vol. 127, # 10, p. 3413 - 3422]
[18]Yasui, Shinro; Tojo, Sachiko; Majima, Tetsuro [Organic and Biomolecular Chemistry, 2006, vol. 4, # 15, p. 2969 - 2973]
[19]Wittig,G. et al. [Chemische Berichte, 1961, vol. 94, p. 676 - 689]
[20]Location in patent: experimental part Motoshima, Kosuke; Sato, Akinori; Yorimitsu, Hideki; Oshima, Koichiro [Bulletin of the Chemical Society of Japan, 2007, vol. 80, # 11, p. 2229 - 2231]
[21]Location in patent: experimental part Yasui, Shinro; Mishima, Masaaki [Phosphorus, Sulfur and Silicon and the Related Elements, 2011, vol. 186, # 4, p. 838 - 840]
[22]Location in patent: experimental part Khursan; Kovaleva; Chainikova; Talipov; Safiullin [High Energy Chemistry, 2010, vol. 44, # 4, p. 284 - 289]
[23]Mukherjee, Debabrata; Ellern, Arkady; Sadow, Aaron D. [Journal of the American Chemical Society, 2012, vol. 134, # 31, p. 13018 - 13026]
[24]Itoh, Masaki; Hashimoto, Yuto; Hirano, Koji; Satoh, Tetsuya; Miura, Masahiro [Journal of Organic Chemistry, 2013, vol. 78, # 16, p. 8098 - 8104]
[25]Yasui, Shinro; Tsujimoto, Munekazu [Journal of Physical Organic Chemistry, 2013, vol. 26, # 12, p. 1090 - 1097]
[26]Gwon, Donghyeon; Lee, Donggun; Kim, Jiyu; Park, Sehoon; Chang, Sukbok [Chemistry - A European Journal, 2014, vol. 20, # 39, p. 12421 - 12425]
[27]Lee, Yong-Min; Yoo, Mi; Yoon, Heejung; Li, Xiao-Xi; Nam, Wonwoo; Fukuzumi, Shunichi [Chemical Communications, 2017, vol. 53, # 67, p. 9352 - 9355]
[28]Aitken, R. Alan; Bjørnstad, Vidar; Massil, Tracy; Skramstad, Jan; Young, Robert J. [Arkivoc, 2017, vol. 2017, # 3, p. 293 - 301]
[29]Szkop, Kevin M.; Zhu, Diya; Longobardi, Lauren E.; Heck, Julian; Stephan, Douglas W. [Dalton Transactions, 2018, vol. 47, # 27, p. 8933 - 8939]
[30]Tanabe, Yoshiaki; Nakajima, Kazunari; Nishibayashi, Yoshiaki [Chemistry - A European Journal, 2018, vol. 24, # 70, p. 18618 - 18622]
[31]Sharma, Namita; Zou, Huai-Bo; Lee, Yong-Min; Fukuzumi, Shunichi; Nam, Wonwoo [Journal of the American Chemical Society, 2021, vol. 143, # 3, p. 1521 - 1528]

3
[ 515-46-8 ]
[ 1038-95-5 ]
Ethyl-tri-p-tolyl-phosphonium-benzolsulfonat [ No CAS ]

Reference： [1]Chemische Berichte,1964,vol. 97,p. 2534 - 2538

4
[ 603-35-0 ]
[ 1038-95-5 ]
[ 92-52-4 ]
[ 613-33-2 ]
[ 644-08-6 ]

Reference： [1]Tetrahedron Letters,1984,vol. 25,p. 391 - 392

5
[ 1038-95-5 ]
[ 613-33-2 ]

Reference： [1]Tetrahedron Letters,2000,vol. 41,p. 6775 - 6779
[2]Tetrahedron Letters,1984,vol. 25,p. 391 - 392

6
[ 7726-95-6 ]
furan-2,3,5(4H)-trione pyridine (1:1) [ No CAS ]
[ 1038-95-5 ]
[ 797-70-6 ]

Reference： [1]Michaelis [Justus Liebigs Annalen der Chemie, 1901, vol. 315, p. 91]

7
[ 536-74-3 ]
[ 1038-95-5 ]
[ 613-33-2 ]
[ 3287-02-3 ]

Reference： [1]Tetrahedron Letters,2000,vol. 41,p. 6775 - 6779

8
[ 7175-54-4 ]
[ 1038-95-5 ]
[ 16812-36-5 ]
[ 797-70-6 ]

Yield	Reaction Conditions	Operation in experiment
	In pentane at -80.15℃;

Reference： [1]Fukuzumi, Shunichi; Shimoosako, Kanji; Suenobu, Tomoyoshi; Watanabe, Yoshihito [Journal of the American Chemical Society, 2003, vol. 125, # 30, p. 9074 - 9082]

9
triphenylphosphine [ No CAS ]
[ 6372-42-5 ]
C₁₈H₂₁P*H⁽¹⁺⁾*BF₄^(1-) [ No CAS ]
[ 1038-95-5 ]

Reference： [1]Chemistry - A European Journal,2007,vol. 13,p. 3796 - 3803

10
C₁₈H₂₁P*H⁽¹⁺⁾*BF₄^(1-) [ No CAS ]
[ 1038-95-5 ]
triphenylphosphine [ No CAS ]
[ 6372-42-5 ]

Reference： [1]Chemistry - A European Journal,2007,vol. 13,p. 3796 - 3803

11
[ 292638-84-7 ]
[ 1038-95-5 ]
[ 38985-79-4 ]
[ 380365-23-1 ]
[ 380365-20-8 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine;palladium diacetate; In acetonitrile;	A solution of <strong>[38985-79-4]2-acetamido-5-bromobenzoic acid</strong> (2.05 g, 7.94 mmol), styrene (1.02 mL, 8.9 mmol), acetonitrile (20 mL) and triethylamine (10 mL) was treated with tritolylphosphine (0.365 g, 1.2 mmol) and Pd(OAc)2 (0.055 g, 0.25 mmol). The reaction mixture was heated at 80 C. for 17 hours then cooled, diluted with water (30 mL) and filtered. The filtrate was washed twice with ether, cooled on ice and then acidified with HCl (2 ml, 12 N). The solid product was collected by filtration and dried to give 2.34 g of compound 12. Preparation of methyl 5-((1E)-2-phenylvinyl)-2-(acetylamino)benzoate (compound 13).

Reference： [1]Patent: US2002/32218,2002,A1

12
[ 537-73-5 ]
[ 1038-95-5 ]
[ 110037-35-9 ]

Yield	Reaction Conditions	Operation in experiment
	With nitrogen;palladium diacetate; In hydrogen;	Example 13 Production of 3-hydroxy-4-methoxycinnamaldehyde In a chemical reactor for hydrogen addition (hydrogenation) under elevated pressure, previously tetrahydrofuran (64 ml) was bubbled with nitrogen gas for 10 minutes. Palladium acetate (58 mg, 0.257 mmol), tri(p-tolyl) phosphine (157 mg, 0.515 mmol), 3-hydroxy-4-methoxycinnamic acid (5.00 g, 25.7 mmol) and pivalic acid anhydride (14.4 g, 77.2 mmol) were added thereto, and thereafter the mixture was bubbled with nitrogen gas for 30 minutes to substitute nitrogen gas completely for the gas in the system of reaction, whereby the system was filled with nitrogen gas. Next, hydrogen gas was added thereinto to substitute hydrogen gas for the gas in the system, and then the mixture was stirred under hydrogen pressure of 3.4 MPa at 80° C. for 24 hours for reaction. Thus obtained reaction solution was concentrated under reduced pressure to remove tetrahydrofuran by vaporization. The remaining residue was subjected to a purification process with a silica gel column chromatography (eluding solvent: toluene/ethyl acetate=4/1) to obtain 3-hydroxy-4-methoxycinnamaldehyde (2.26 g, 12.7 mmol, yield: 49percent).

Reference： [1]Patent: US2002/133037,2002,A1

13
[ 100-69-6 ]
2-bromo-4-chlorobenzyloxybenzene [ No CAS ]
[ 1038-95-5 ]
4-chloro-2-[2-(pyridin-2-yl)vinyl]benzyloxybenzene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
58%	With sodium acetate; magnesium sulfate In N,N-dimethyl-formamide	Preparation of 4-chloro-2-[2-(pyridin-2-yl)vinyl]benzyloxybenzene Preparation of 4-chloro-2-[2-(pyridin-2-yl)vinyl]benzyloxybenzene 124.4 g (417.8 mmol) of 2-Bromo-4-chlorobenzyloxybenzene, 54.8 ml (501.4 mmol) of 2-vinylpyridine, 4.69 g (20.9 mmol) palladium acetate, 25.4 g (83.6 mmol) tritolylphosphine, and 48 g (584.9 mmol) sodium acetate are heated together in 200 ml DMF at 165° C. (oil bath temperature) under nitrogen for 8 hours. The cooled mixture is evaporated to dryness in vacuo. The residue is then diluted with Et2 O:DCM (3:1, 1 L) and washed with sodium carbonate solution (1M, 3*1 L). The aqueous washings are extracted with Et2 O:DCM (3:1, 1L) and the combined organic extract dried using MgSO4, filtered through celite, and evaporated to dryness to leave an orange solid. Flash chromatography (SiO2, DCM:pentane 3:1) gave a yellow solid which was triturated with pentane (600 ml) to give the title compound as a pale yellow solid (77.5 g, 58%), m.p. 105.2-105.8° C. 6H (250 MHz, CDCl3) 8.60 (d, J=4.5 Hz, 1H), 7.96 (d, J=16.3 Hz, 1H), 7.64-7.60 (m, 2H), 7.46-7.34 (m, 7H), 7.24 (d, J=16.6 Hz, 1H), 7.18-7.11 (m, 1H), 6.95 (d, J=8.9 Hz, 1H), 5.16 (s, 2H).

Reference： [1]Current Patent Assignee: EURO CELTIQUE S.A. - US6166041, 2000, A

14
[ 1295-35-8 ]
[ 1038-95-5 ]
[ 82999-54-0 ]

Reference： [1]Inorganic Chemistry,1983,vol. 22,p. 411 - 418

15
[ 152386-96-4 ]
[ 1038-95-5 ]
[ 146645-28-5 ]
[ 797-70-6 ]

Yield	Reaction Conditions	Operation in experiment
	In dichloromethane 25°C;

Reference： [1]Jacobi, Bridey Grant; Laitar, David S.; Pu, Lihung; Wargocki, Michael F.; DiPasquale, Antonio G.; Fortner, Kevin C.; Schuck, Stephany M.; Brown, Seth N. [Inorganic Chemistry, 2002, vol. 41, # 18, p. 4815 - 4823]

16
[ 12081-16-2 ]
[ 1038-95-5 ]
[ 24554-70-9 ]

Reference： [1]Journal of the American Chemical Society,1974,vol. 96,p. 2762 - 2774

17
[ 1295-35-8 ]
[ 645-49-8 ]
[ 1038-95-5 ]
[ 53586-22-4 ]

Reference： [1]Journal of Organometallic Chemistry,1974,vol. 74,p. 121 - 134

18
[ 1295-35-8 ]
[ 103-30-0 ]
[ 1038-95-5 ]
[ 53564-87-7 ]

Reference： [1]Journal of Organometallic Chemistry,1974,vol. 74,p. 121 - 134

19
[ 92361-49-4 ]
[ 1038-95-5 ]
[ 92361-56-3 ]

Reference： [1]Synthesis and Reactivity in Inorganic and Metal-Organic Chemistry,1984,vol. 14,p. 383 - 400

20
[ 1295-35-8 ]
[ 20913-05-7 ]
[ 1038-95-5 ]
[ 104549-98-6 ]

Reference： [1]Organometallics,1986,vol. 5,p. 2356 - 2359

21
[ 12266-72-7 ]
[ 1038-95-5 ]
[ 109215-98-7 ]

Reference： [1]Inorganica Chimica Acta,1987,vol. 128,p. 93 - 104

22
[ 1295-35-8 ]
[ 637-27-4 ]
[ 1038-95-5 ]
[ 74-85-1 ]
[ 74887-07-3 ]
[ 108-95-2 ]

Reference： [1]Journal of the American Chemical Society,1980,vol. 102,p. 3758 - 3764

23
[ 1295-35-8 ]
[ 2554-06-5 ]
[ 1038-95-5 ]
[ 71-43-2 ]
[(Ni(PC6H4CH3-4))2(μ-(η-CH2CH(Me)Si(μ-O))4)]*2C6H6 [ No CAS ]

Reference： [1]Journal of Organometallic Chemistry,2000,vol. 605,p. 221 - 225

24
[ 1295-35-8 ]
[ 2627-95-4 ]
[ 1038-95-5 ]
[ 189372-78-9 ]

Reference： [1]Journal of Organometallic Chemistry,2000,vol. 605,p. 221 - 225

25
[ 1295-35-8 ]
[ 2554-06-5 ]
[ 1038-95-5 ]
[ 306770-74-1 ]

Reference： [1]Journal of Organometallic Chemistry,2000,vol. 605,p. 221 - 225

26
[ 1295-35-8 ]
[ 21230-92-2 ]
[ 1038-95-5 ]
[ 62816-21-1 ]
[ 209798-23-2 ]

Reference： [1]New Journal of Chemistry,1998,vol. 22,p. 467 - 472

27
[ 20759-14-2 ]
[ 133850-81-4 ]
[ 1038-95-5 ]
[ 195449-00-4 ]

Reference： [1]Chemische Berichte,1997,vol. 130,p. 1315 - 1319

28
[ 1295-35-8 ]
1-methyl-2-(triphenylphosphoranylideneamino)benzimidazole [ No CAS ]
[ 1038-95-5 ]
[ 190433-74-0 ]

Reference： [1]Journal of Organometallic Chemistry,1999,vol. 582,p. 371 - 377

29
[ 1295-35-8 ]
[ 5162-63-0 ]
[ 1038-95-5 ]
[ 467435-00-3 ]

Reference： [1]Polyhedron,2002,vol. 21,p. 1261 - 1265

30
[ 1295-35-8 ]
C₆H₄P(C₆H₅)3NH₂⁽¹⁺⁾*Br^(1-) = (C₆H₄P(C₆H₅)3NH₂)Br [ No CAS ]
[ 1038-95-5 ]
[ 209798-29-8 ]

Reference： [1]New Journal of Chemistry,1998,vol. 22,p. 467 - 472

31
[ 797-70-6 ]
[ 1038-95-5 ]

Yield	Reaction Conditions	Operation in experiment
91%	With chloro-trimethyl-silane; magnesium at 20℃; for 4h;	A typical procedure for the reduction of 2a General procedure: To a mixture of Mg powder (8 mmol, 4 mol equiv), Me3SiCl (6 mmol, 3 mol equiv), and DMI (8 mL) was added 2a (2 mmol), and the whole mixture was stirred for 2 h at room temperature. To the reaction mixture was added satd aq (NH4)2CO3, and the mixture was extracted with Et2O (10 mL 3). The combined organic layers were washed with satd aq NaCl, dried over Na2SO4, and concentrated under reduced pressure. The resultant was analyzed by 31P NMR to find that 1a and 2a were obtained in 97:3 ratio. The desired 1a was obtained in 96% yield after purification by silica gel column chromatography (hexane/AcOEt = 5:1) (Table 1, entry 1).
89%	With copper(II) trifluoromethanesulfonate; 1,1,3,3-Tetramethyldisiloxane In toluene at 100℃; Inert atmosphere;
85%	With oxalyl dichloride; diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate; triethylamine In dichloromethane at 40℃; for 2h; Inert atmosphere;	General procedure for the reduction of tertiary phosphine oxides General procedure: To a solution of tertiary phosphine oxides 2 (0.4mmol) in CH2Cl2 (2mL) was added oxalyl chloride (0.4mmol) dropwise at room temperature under an argon atmosphere. After 30min, HEH (1mmol) was added to the mixture in one portion as well as TEA (3mmol). The mixture was stirred for another 2h at 40°C, and then diluted with H2O (10mL). The resulting mixture was extracted with CH2Cl2 repeatedly. The extracts were dried (anhydrous Na2SO4) and evaporated. The crude product was purified by column chromatography on silica gel using ethyl acetate/petroleum ether to afford the pure product.

84%	With diethoxymethylane; Bis(p-nitrophenyl) phosphate In toluene at 110℃; Inert atmosphere; chemoselective reaction;
82%	With chloro-trimethyl-silane; tetrabutylammomium bromide; copper; zinc In acetonitrile at 45℃; Electrochemical reaction; Inert atmosphere;
81%	With oxalyl dichloride; hydrogen In chloroform-d1 at 130℃; for 18h;
80%	Stage #1: tri(4-methylphenyl)phosphine oxide With trifluoroacetic anhydride In 1,4-dioxane at 20℃; for 0.5h; Inert atmosphere; Stage #2: With 15-crown-5; sodium hydride; sodium hydrogencarbonate In 1,4-dioxane at 150℃; for 24h; Inert atmosphere;	2 Synthesis of Tris(4-methylphenyl)phosphine Into the reactor were added 0.2 mmol of tris(4-methylphenyl)phosphine oxide, 0.36 mmol of trifluoroacetic anhydride, and 1 ml of solvent dioxane. Stir at room temperature under a nitrogen atmosphere for 30 min; after the reaction is complete, continue to add 0.2 mmol of sodium bicarbonate, 0.24 mmol of 15-Crown-5, and 1.2 mmol of sodium hydride under a nitrogen environment. Under the environment of 150 oC, continue stirring for 24 hours, stop the reaction and cool to room temperature, and distill under reduced pressure to remove the solvent. The crude product is separated by column chromatography to obtain the target product with a yield of 80%.
74%	With triphenyl phosphite; diphenyl hydrogen phosphite; iodine In tetrahydrofuran at 20℃; Inert atmosphere;
67%	Stage #1: tri(4-methylphenyl)phosphine oxide With [Fe(CO)(1,3-bis(diphenylphosphino)propane)H(NO)]; phenylsilane; N-ethyl-N,N-diisopropylamine In toluene at 100℃; for 18h; Schlenk technique; Stage #2: With sodium hydroxide In methanol; water; toluene at 20℃; for 1h; Schlenk technique; chemoselective reaction;
	Multi-step reaction with 2 steps 1.1: oxalyl dichloride; tetrabutylammonium trifluoromethylsulfonate / acetonitrile / 0.17 h / 20 °C / Inert atmosphere 2.1: tetrabutylammonium trifluoromethylsulfonate / acetonitrile / 8 h / 20 °C / Electrochemical reaction; Undivided electrochemical cell with aluminum anode/platinum cathode; Inert atmosphere 2.2: Inert atmosphere
96 %Chromat.	With [AlH₃(triethylamine)] In hexane at 20℃; for 0.166667h; Inert atmosphere; Schlenk technique;	Compound IIIa (general procedure). General procedure: Triphenylphosphine oxide or sulfide (1 mmol), dry hexane (1 mL), and Ic (1 mmol) were added to a Schlenk tube under the atmosphere of nitrogen. The reaction was carried out at room temperature for 10 min and monitored by TLC. Upon completion of the process the reaction mixture was filtered by silica gel and washed several times with ethyl acetate. Ethyl acetate was evaporated and the residue purified by flash chromatography on silica gel with pure cyclohexane toafford the desired phosphine. The yield was determined by GC without additional purification.
96 %Spectr.	With hexylsilane; trifluorormethanesulfonic acid In toluene at 70℃; for 24h; Inert atmosphere; Sealed tube; chemoselective reaction;

Reference： [1]Kuroboshi, Manabu; Kita, Toshihito; Aono, Asuka; Katagiri, Toshimasa; Kikuchi, Seiya; Yamane, Syoko; Kawakubo, Hiromu; Tanaka, Hideo [Tetrahedron Letters, 2015, vol. 56, # 7, p. 918 - 920]
[2]Location in patent: scheme or table Li, Yuehui; Das, Shoubhik; Zhou, Shaolin; Junge, Kathrin; Beller, Matthias [Journal of the American Chemical Society, 2012, vol. 134, # 23, p. 9727 - 9732]
[3]Zhang, Tong-Xin; Zhang, Wei-Xi; Luo, Mei-Ming [Chinese Chemical Letters, 2014, vol. 25, # 1, p. 176 - 178]
[4]Li, Yuehui; Lu, Liang-Qiu; Das, Shoubhik; Pisiewicz, Sabine; Junge, Kathrin; Beller, Matthias [Journal of the American Chemical Society, 2012, vol. 134, # 44, p. 18325 - 18329]
[5]Location in patent: scheme or table Kawakubo, Hiromu; Kuroboshi, Manabu; Yano, Tomotake; Kobayashi, Kazuma; Kamenoue, Syogo; Akagi, Tomomi; Tanaka, Hideo [Synthesis, 2011, # 24, p. 4091 - 4098]
[6]Stepen, Arne J.; Bursch, Markus; Grimme, Stefan; Stephan, Douglas W.; Paradies, Jan [Angewandte Chemie - International Edition, 2018, vol. 57, # 46, p. 15253 - 15256][Angew. Chem., 2018, vol. 130, # 46, p. 15473 - 15476,4]
[7]Current Patent Assignee: HAINAN UNIVERSITY - CN113698431, 2021, A Location in patent: Paragraph 0020
[8]Li, Peng; Wischert, Raphael; Métivier, Pascal [Angewandte Chemie - International Edition, 2017, vol. 56, # 50, p. 15989 - 15992][Angew. Chem., 2017, vol. 129, # 50, p. 16205 - 16208,4]
[9]Rommel, Susanne; Belger, Christian; Begouin, Jeanne-Marie; Plietker, Bernd [ChemCatChem, 2015, vol. 7, # 8, p. 1292 - 1301]
[10]Kuroboshi, Manabu; Yano, Tomotake; Kamenoue, Shogo; Kawakubo, Hiromu; Tanaka, Hideo [Tetrahedron, 2011, vol. 67, # 32, p. 5825 - 5831]
[11]Yang, Shuyan; Han, Xinxin; Luo, Minmin; Gao, Jing; Chu, Wenxiang; Ding, Yuqiang [Russian Journal of General Chemistry, 2015, vol. 85, # 5, p. 1156 - 1160][Zh. Obshch. Khim.]
[12]Schirmer, Marie-Luis; Jopp, Stefan; Holz, Jens; Spannenberg, Anke; Werner, Thomas [Advanced Synthesis and Catalysis, 2016, vol. 358, # 1, p. 26 - 29]

32
N,N-dimethyl-S-difluoromethyl-S-phenylsulfoximinium tetrafluoroborate [ No CAS ]
[ 1038-95-5 ]
P-(difluoromethyl)tri(p-tolyl)phosphonium tetrafluoroborate [ No CAS ]
[ 797-70-6 ]

Yield	Reaction Conditions	Operation in experiment
65 %Spectr.	In dichloromethane at 20℃; for 1h; Inert atmosphere;

Reference： [1]Location in patent: experimental part Prakash, G.K. Surya; Zhang, Zhe; Wang, Fang; Ni, Chuanfa; Olah, George A. [Journal of Fluorine Chemistry, 2011, vol. 132, # 10, p. 792 - 798]

33
di-μ-chlorobis{(acetophenone oxime)palladium(II)} [ No CAS ]
[ 1038-95-5 ]
[Pd(C,N-C₆H₄(C(Me)=NOH)-2)Cl(PTol₃)] [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
66%	In acetone at 20℃; for 1h;	7 3.1 General procedure General procedure: The synthesis of the cyclopalladated compounds have been carried out using the procedure described by Onue etal. [16] with minor modifications. In a general procedure, to a stirred suspension of [PdCl(C2,N-aphox)]2 (100mg, 0.18mmol) in 10mL of acetone, 0.38mmol of the suitable phosphine ligand (mass of reactants: L1=99.8, L2=120.3, L3=106.7, L4=105.1, L5=134.0, L6=115.8mg) dissolved in 5mL of acetone was added dropwise, affording a yellow solution. The mixture was stirred for 1hat room temperature and slow evaporation of the final solutions at room temperature afforded crystals in good yields. The crystals were collected, washed with pentane and dried under vacuum. Suitable single crystals for X-ray diffraction determination of 1-5 have been obtained by slow evaporation of a solution containing 2-5mg of the complex in 5mL of acetone. Yellow crystals were obtained after 1 week.
	In dichloromethane addn. of ligand to a suspn. of Pd complex in CH2Cl2;

Reference： [1]Bozza, Gabriela F.; de Farias, Renan L.; de Souza, Ronan F.F.; Rocha, Fillipe V.; Barra, Carolina V.; Deflon, Victor M.; de Almeida, Eduardo T.; Mauro, Antonio E.; Netto, Adelino V.G. [Journal of Molecular Structure, 2019, vol. 1175, p. 195 - 207]
[2]Vicente, Jose; Chicote, Maria-Teresa; Abellan-Lopez, Antonio; Bautista, Delia [Dalton Transactions, 2012, vol. 41, # 3, p. 752 - 762]

34
[ 1228793-95-0 ]
[ 1228793-96-1 ]
[ 1228793-97-2 ]
[ 6783-05-7 ]
[ 5228-61-5 ]
[ 556-08-1 ]
[ 1038-95-5 ]
[ 1228793-81-4 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydride; sodium hydrogencarbonate; potassium carbonate; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; trifluoroacetic acid;Pd(PPh3)4; palladium; In 1,2-dimethoxyethane; ethanol; dichloromethane; water;	Synthesis of 4-acetamido-N-(2-amino-5-phenethylphenyl)benzamide (BRD-7050) To a stirred solution of <strong>[5228-61-5]5-bromo-2-nitroaniline</strong> (4.0 g, 18.43 mmol, 1.0 eq), 4-acetamidobenzoic acid (4.95 g, 27.6 mmol, 1.5 eq) and BOP (10.60 g, 23.96 mmol, 1.3 eq) was added sodium hydride (2.96 g, 123.0 mmol, 6.7 eq) portion-wise at 0 C. The reaction mixture was allowed to warm to room temperature and stir for 60 h. The solvents were evaporated under reduced pressure. The residue was diluted with a saturated solution of sodium bicarbonate. The obtained precipitate was filtered. The product was purified by column chromatography (silica gel, 25% EtOAc/CH2Cl2) to afford the desired product (3.31 g, 40% yield). A mixture of tert-butyl 2-(4-acetamidobenzamido)-4-bromophenylcarbamate (0.50 g, 1.11 mmol, 1.0 eq), (E)-styrylboronic acid (0.33 g, 2.23 mmol, 2.0 eq), potassium carbonate (0.46 g, 3.335 mmol, 3.0 eq), Pd(PPh3)4 (0.09 g, 0.08 mmol, 0.07 eq) and tritolyl phosphine (0.10 g, 0.33 mmol, 0.3 eq) in DME/H2O (30 mL) was heated to reflux for 20 h. The reaction mixture was diluted with water. The obtained solid was filtered. The crude product was purified by column chromatography (silica gel, 2% MeOH/CH2Cl2) to obtain pure product (0.30 g, 57% yield). To a solution of (E)-tert-butyl 2-(4-acetamidobenzamido)-4-styrylphenylcarbamate (0.15 g, 0.32 mmol, 1.0 eq) in ethanol (10 mL) was added palladium on carbon (0.02 g, 0.23 mmol, 0.7 eq). The reaction mixture was stirred under H2 atmosphere for 20 h. The reaction mixture was filtered through celite, the solids were washed with methanol. The reaction was then concentrated under reduced pressure to afford an off white solid (0.14 g, 93% crude yield) which was used in the next step without further purification. To a solution of tert-butyl 2-(4-acetamidobenzamido)-4-phenethylphenylcarbamate (0.14 g, 0.29 mmol) in CH2Cl2 (3 mL) at 0 C. was added TFA (2 mL) dropwise. The reaction mixture was slowly warmed to room temperature and stirred for 2 h. The solvent was removed by evaporation under reduced pressure. The crude residue was diluted with water and quenched with a saturated aqueous solution of sodium bicarbonate. The obtained solid was filtered, washed with water and dried under vacuum to afford the desired product (0.08 h, 68% yield). ESI+ MS: m/z (rel intensity) 374 (95.0, M+H).

Reference： [1]Patent: US2012/101147,2012,A1

35
[ 4542-75-0 ]
[ 1038-95-5 ]
4,4'-bis((tri(p-tolyl)phosphonio)methyl)diphenyl ether dibromide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 2606 - 2622

36
[ 7681-65-4 ]
[ 51-52-5 ]
[ 1038-95-5 ]
[ 1404364-15-3 ]

Reference： [1]Inorganic Chemistry,2012,vol. 51,p. 12248 - 12259

37
[ 100-42-5 ]
[ 1038-95-5 ]
[ 4714-21-0 ]

Yield	Reaction Conditions	Operation in experiment
77%	With sodium acetate; silver trifluoroacetate; palladium dichloride In acetonitrile at 60℃; for 24h; Schlenk technique; Inert atmosphere;	4.2.1 General procedure General procedure: Under N2 atmosphere, NaOAc (4.0 equiv), PPh3 1a (0.5 mmol), PdCl2 (10.0 mol %), AgOOCCF3 (5.0 equiv), CH3CN (2.0 mL) and methyl acrylate 2a (0.6 mmol) were successively added into a Schlenk reaction tube. Then the mixture was stirred at 60 °C for 24 h. After cooling to room temperature, the solvent was evaporated in vacuo and then purified by flash column chromatography on silica gel to give the pure product 3a.

Reference： [1]Ma, Ming-Tao; Lu, Jian-Mei [Tetrahedron, 2013, vol. 69, # 9, p. 2102 - 2106]

38
[ 292638-85-8 ]
[ 1038-95-5 ]
methyl 3-(4-methylphenyl)acrylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%	With sodium acetate; silver trifluoroacetate; palladium dichloride In acetonitrile at 60℃; for 24h; Schlenk technique; Inert atmosphere;	4.2.1 General procedure General procedure: Under N2 atmosphere, NaOAc (4.0 equiv), PPh3 1a (0.5 mmol), PdCl2 (10.0 mol %), AgOOCCF3 (5.0 equiv), CH3CN (2.0 mL) and methyl acrylate 2a (0.6 mmol) were successively added into a Schlenk reaction tube. Then the mixture was stirred at 60 °C for 24 h. After cooling to room temperature, the solvent was evaporated in vacuo and then purified by flash column chromatography on silica gel to give the pure product 3a.

Reference： [1]Ma, Ming-Tao; Lu, Jian-Mei [Tetrahedron, 2013, vol. 69, # 9, p. 2102 - 2106]

39
[ 141-32-2 ]
[ 1038-95-5 ]
n-butyl 4-methyl-cinnamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
68%	With sodium acetate; silver trifluoroacetate; palladium dichloride In acetonitrile at 60℃; for 24h; Schlenk technique; Inert atmosphere;	4.2.1 General procedure General procedure: Under N2 atmosphere, NaOAc (4.0 equiv), PPh3 1a (0.5 mmol), PdCl2 (10.0 mol %), AgOOCCF3 (5.0 equiv), CH3CN (2.0 mL) and methyl acrylate 2a (0.6 mmol) were successively added into a Schlenk reaction tube. Then the mixture was stirred at 60 °C for 24 h. After cooling to room temperature, the solvent was evaporated in vacuo and then purified by flash column chromatography on silica gel to give the pure product 3a.

Reference： [1]Ma, Ming-Tao; Lu, Jian-Mei [Tetrahedron, 2013, vol. 69, # 9, p. 2102 - 2106]

40
[ 59171-72-1 ]
[ 1038-95-5 ]
[ 1370731-61-5 ]
[ 1370731-50-2 ]

Yield	Reaction Conditions	Operation in experiment
71%; 21%	With silver(I) acetate; palladium diacetate; trifluoroacetic acid; In 1-methyl-pyrrolidin-2-one; at 120℃; for 48h;Inert atmosphere; Schlenk technique;	General procedure: 4.3.28 methyl 2-phenyl-5-(4-methylphenyl)oxazole-4-carboxylate (4h) A suspension of Pd(OAc)2 (10 mol %), Ar3P (0.33 mmol or 0.75 mmol), AgOAc (3.0 mmol), TFA (1.0 mmol) and azole-4-carboxylates (0.5 mmol) in NMP (2 mL) was introduced to a Schlenk tube. After stirring at 120 C under argon for 24 h (reactions with 0.33 mmol of Ph3P), or 48 h (reactions with 0.75 mmol of Ph3P), the reaction mixture was diluted with ethyl acetate, and then filtered through a pad of Celite. Volatiles were removed in vacuo to give the crude products, which was purified by flash column chromatography on silica gel to afford pure arylated products Yield 104 mg (71%). 1H NMR (300 MHz, CDCl3) δ 2.41 (s, 3H), 3.97 (s, 3H), 7.29 (d, J=8.2 Hz, 2H), 7.46-7.49 (m, 3H), 8.04 (d, J=8.2 Hz, 2H), 8.13-8.16 (m, 2H) ppm; 13C NMR (75 MHz, CDCl3) δ 161.8, 158.5, 154.6, 139.8, 130.0, 128.2, 127.8, 127.4, 125.8, 125.4, 123.2, 51.3, 20.6 ppm.

Reference： [1]Tetrahedron,2013,vol. 69,p. 3281 - 3286

41
[ 1038-95-5 ]
[ 7113-02-2 ]
[ 1315510-22-5 ]
[ 1370731-59-1 ]

Yield	Reaction Conditions	Operation in experiment
1: 75% 2: 16%	With silver(I) acetate; palladium diacetate; trifluoroacetic acid In 1-methyl-pyrrolidin-2-one at 120℃; for 24h; Inert atmosphere; Schlenk technique;	3.22 methyl 2-phenyl-5-(4-methylphenyl)thiazole-4-carboxylate ;(4a) General procedure: 4.3.22 methyl 2-phenyl-5-(4-methylphenyl)thiazole-4-carboxylate ;(4a) A suspension of Pd(OAc)2 (10 mol %), Ar3P (0.33 mmol or 0.75 mmol), AgOAc (3.0 mmol), TFA (1.0 mmol) and azole-4-carboxylates (0.5 mmol) in NMP (2 mL) was introduced to a Schlenk tube. After stirring at 120 C under argon for 24 h (reactions with 0.33 mmol of Ph3P), or 48 h (reactions with 0.75 mmol of Ph3P), the reaction mixture was diluted with ethyl acetate, and then filtered through a pad of Celite. Volatiles were removed in vacuo to give the crude products, which was purified by flash column chromatography on silica gel to afford pure arylated products Yield 116 mg (75%). 1H NMR (300 MHz, CDCl3) δ 2.40 (s, 3H), 3.86 (s, 3H), 7.24 (d, J=7.9 Hz, 2H), 7.43-7.45 (m, 5H), 7.95-7.98 (m, 2H) ppm; 13C NMR (75 MHz, CDCl3) δ 164.8, 161.8, 145.8, 139.5, 138.5, 131.8, 129.6, 128.8, 128.0, 126.3, 125.8, 51.3, 20.4 ppm.

Reference： [1]Li, Ziyuan; Zhou, Haipin; Xu, Jinyi; Wu, Xiaoming; Yao, Hequan [Tetrahedron, 2013, vol. 69, # 15, p. 3281 - 3286]

42
[Cu^II(1-(2-phenethyl)-5-[2-(2-pyridyl)ethyl]-1,5-diazacyclooctane)(O₂)]⁺ [ No CAS ]
[ 1038-95-5 ]
[Cu^II(1-(2-phenethyl)-5-[2-(2-pyridyl)ethyl]-1,5-diazacyclooctane)(O)]²⁺ [ No CAS ]
[ 797-70-6 ]

Yield	Reaction Conditions	Operation in experiment
86 %Spectr.	In acetone at -85℃;

Reference： [1]Tano, Tetsuro; Okubo, Yuri; Kunishita, Atsushi; Kubo, Minoru; Sugimoto, Hideki; Fujieda, Nobutaka; Ogura, Takashi; Itoh, Shinobu [Inorganic Chemistry, 2013, vol. 52, # 18, p. 10431 - 10437]

43
[ 1038-95-5 ]
[ 298-12-4 ]
tris-(p-tolyl)phosphonioglycolate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%	In diethyl ether at 20℃; Inert atmosphere; Schlenk technique;	4.6. Tris-(p-tolyl)phosphonioglycolate (3c) Reaction of glyoxylic acid (1.06 g, 11.5 mmol) in dry diethyl ether (100 mL) with tris-(p-tolyl)phosphane (3.54 g, 11.6 mmol) in dry diethyl ether (20 mL) at room temperature and workup as described for 3a gave 3.42 g (78%) of a white powder of 3c.

Reference： [1]Basvani, Kaleswara Rao; Fomina, Olga S.; Yakhvarov, Dmitry G.; Heinicke, Joachim [Polyhedron, 2014, vol. 67, p. 306 - 313]

44
[Pd(acac)(MeCN)₂]BF₄ [ No CAS ]
[ 1038-95-5 ]
acetylacetonatobis(tri(p-tolyl)phosphine)palladium(II) tetrafluoroborate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
95%	In dichloromethane at 20℃; for 1h;	3 4.7 Preparation of [Pd(acac)(P(p-Tol)₃)₂]BF₄ (6) P(p-Tol)3 (0.913g, 3.00mmol) was dissolved in dichloromethane (20mL) and 1 (0.562g, 1.50mmol) was slowly added. Then, the reaction mixture was stirred for 1h at ambient temperature. The resulting yellow solution was filtered, and the solvent of the filtrate was removed under reduced pressure yielding ayellow solid (1.283g, 95%). 1H NMR (CDCl3): δ 7.2-7.6 (m, 24H, Ar), 5.5 (s, 1H, CH), 2.4 (s, 18H, Ar), 1.5 (s, 6H, CH3). 13C NMR ((CD3)2CO): δ 186.2 (s, C=O), 141.5 (d, p-CH, Ar), 134.0 (d, o-CH, Ar), 129.3 (d, m-CH, Ar), 100.4 (d, CH), 26.0 (q, CH3), 21.3 (q, CH3, Ar). Spectroscopic data were found to match literature data [45,48].

Reference： [1]Suslov, Dmitry S.; Bykov, Mikhail V.; Belova, Marina V.; Abramov, Pavel A.; Tkach, Vitaly S. [Journal of Organometallic Chemistry, 2014, vol. 752, p. 37 - 43]

45
[ 1038-95-5 ]
[ 797-70-6 ]
tetra(p-tolyl)diphosphane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With air for 1h; Irradiation;

Reference： [1]Yasui, Shinro; Ogawa, Yuya; Shioji, Kosei; Yamazaki, Shoko [Chemistry Letters, 2013, vol. 42, # 12, p. 1478 - 1480]

46
1,3-(μ-propanedithiolato)diironhexacarbonyl [ No CAS ]
[ 1038-95-5 ]
[ 1598427-34-9 ]

Yield	Reaction Conditions	Operation in experiment
52%	With trimethylamine-N-oxide In acetonitrile at 20℃; for 2h; Inert atmosphere; Schlenk technique;	Synthesis of [{(μ-SCH2)2CH2}Fe2(CO)5P(PhOMe-p)3] (1) General procedure: A mixture of [{(μ-SCH2)2CH2}Fe2(CO)6] (0.193 g, 0.5 mM), P(PhOMe-p)3 (0.211 g, 0.6 mM), and Me3NO·2H2O (0.056 g, 0.5 mM) was dissolved in MeCN (15 mL) and was stirred at room temperature for 2 h to give a black-red solution. The solvent was removed on a rotary evaporator and the residue was subjected to preparative TLC separation using CH2Cl2/petroleum ether (v/v = 1 : 5) as eluent. From the main red band, 1 (0.241 g, 68%) was obtained as a red solid.

Reference： [1]Zhao, Pei-Hua; Li, Xin-Hang; Liu, Yun-Feng; Liu, Ya-Qing [Journal of Coordination Chemistry, 2014, vol. 67, # 5, p. 766 - 778]

47
[ 603-35-0 ]
[ 1038-95-5 ]
[ 18957-70-5 ]
C₁₆H₁₉OP [ No CAS ]
[ 6840-28-4 ]
[ 797-70-6 ]
C₁₇H₂₁OP [ No CAS ]
[ 791-28-6 ]
[ 4252-88-4 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: triphenylphosphine; Tri(p-tolyl)phosphine With dicarbonylacetylacetonato rhodium (I); propene; hydrogen at 150℃; Stage #2: With tert.-butylhydroperoxide	C Comparative Experiment C - Not an embodiment of the invention Comparative Experiment C - Not an embodiment of the invention Comparative Experiment A is repeated, except under a 1 : 1 propylene: hydrogen g mixture. This shows the fastest rates of overall ligand scrambling so far and introduces another ligand degradation pathway, shown below in Scheme 2, which introduces propyl moieties onto the phosphorus (see Table 5 where "PrxPhyPO" represents the new propyl- substituted phosphine oxides). Nearly all of the starting TPP and (p-Tol^P has been consumed. Without wishing to be bound by any theory, this is most likely related to the ability of this gas mixture to essentially react CO off of the Rh centers and make vacant binding sites for formation of Rh aggregates and ligand scrambling reactions. In the absence of BZEV1, the aryl exchanged phosphines Ph2(p-Tol)P and Ph(p-Tol) 2P have reached their maximum concentration within the 20 minute interval to the first sample. Subsequent exchange of propyl substituents into the mixture of aryl phosphines then occurs more + H2 Rh Scheme 2. In the presence of propylene and hydrogen, the rhodium catalyzed ligand scrambling reactions result in additional propyl substituted ligands. Propyldiphenylphosphine (Pr(Ph)2P), Propyldi-(paratolyl)phosphine (Pr(p-Tol)2P), and Propyl(phenyl)(paratolyl)phosphine (Pr(Ph)(p-Tol)P) are shown. Lesser amounts of further exchanged phosphines are also formed. Table 5 - Comparitive Example under 1:1 ^Propylene but without BZIM demonstrating rapid aryl exchange between tri-arylphosphines and propyl group insertion.

Reference： [1]Current Patent Assignee: DOW INC - WO2014/149915, 2014, A1 Location in patent: Page/Page column 36-38

48
[ 603-35-0 ]
[ 1038-95-5 ]
[ 18957-70-5 ]
[ 6840-28-4 ]
[ 797-70-6 ]
[ 791-28-6 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: triphenylphosphine; Tri(p-tolyl)phosphine With benzoimidazole; dicarbonylacetylacetonato rhodium (I); hydrogen at 150℃; Stage #2: With tert.-butylhydroperoxide	2 Example 2 Example 2 Comparative Experiment B is repeated, except that 1 wt. % BZIM is added at the beginning. The results are shown in Table 4, and show substantially less aryl interchange over the same time period. Furthermore, in the presence of BZIM, the composition appears to be leveling off well before reaching the apparent equilibrium mixture seen in the Comparative Experiment B (i.e., in the absence of BZIM). Table 4 - Example with BZIM (under hydrogen) demonstrating substantially reduced aryl exchange between tri-arylphosphines compared to without BZIM.

Reference： [1]Current Patent Assignee: DOW INC - WO2014/149915, 2014, A1 Location in patent: Page/Page column 36

49
[ 603-35-0 ]
[ 1038-95-5 ]
[ 797-70-6 ]
[ 791-28-6 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: triphenylphosphine; Tri(p-tolyl)phosphine With benzoimidazole; dicarbonylacetylacetonato rhodium (I); propene at 150℃; Stage #2: With tert.-butylhydroperoxide	1 Example 1 Example 1 The procedure of Comparative Experiment A is repeated, except that 1 wt. % BZIM is added at the beginning. The results are shown in Table 2, and show essentially no aryl interchange over the same time period. Table 2 - Example with BZIM (under propylene) demonstrating essentially no aryl exchange between tri-arylphosphines.

Reference： [1]Current Patent Assignee: DOW INC - WO2014/149915, 2014, A1 Location in patent: Page/Page column 35

50
[ 1038-95-5 ]
[ 7787-70-4 ]
[CuBr{P(p-tolyl)₃}₃] [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
68%	In methanol; at 60℃; for 0.5h;Inert atmosphere;	General procedure: The complexes were prepared according to the following method [14]: 1mmol of <strong>[7787-70-4]copper(I) bromide</strong> or copper(I) chloride is stirred in methanol until complete dissolution. Then, 2.1mmol of the corresponding phosphine ligand was added. The mixture was stirred at 60C for 30min. under nitrogen atmosphere. A microcrystalline precipitate was obtained by concentration of the solution at reduced pressure. The solid product was dissolved in a dichloromethane/methanol mixture and the solution was gradually cooled to 4C to give an air stable and colorless crystalline solid suitable for X-ray single-crystal diffraction studies.
68%	In methanol; at 60℃; for 0.5h;Inert atmosphere;	General procedure: The complexes were prepared according to the following method [14]: 1mmol of <strong>[7787-70-4]copper(I) bromide</strong> or copper(I) chloride is stirred in methanol until complete dissolution. Then, 2.1 mmol of the corresponding phosphine ligand was added. The mixture was stirred at 60C for 30min. under nitrogen atmosphere. A microcrystalline precipitate was obtained by concentration of the solution at reduced pressure. The solid product was dissolved in a dichloromethane/methanol mixture and the solution was gradually cooled to 4C to give an air stable and colorless crystalline solid suitable for X-ray single-crystal diffraction studies.

Reference： [1]Polyhedron,2014,vol. 85,p. 405 - 411
[2]Polyhedron,2015,vol. 85,p. 405 - 411

51
[ 1038-95-5 ]
copper(l) chloride [ No CAS ]
[{(p-tolyl)₃P}₃Cu₂Cl₂] [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
55%	In methanol at 60℃; for 0.5h; Inert atmosphere;	2.3 Preparation of complexes General procedure: The complexes were prepared according to the following method [14]: 1mmol of copper(I) bromide or copper(I) chloride is stirred in methanol until complete dissolution. Then, 2.1mmol of the corresponding phosphine ligand was added. The mixture was stirred at 60°C for 30min. under nitrogen atmosphere. A microcrystalline precipitate was obtained by concentration of the solution at reduced pressure. The solid product was dissolved in a dichloromethane/methanol mixture and the solution was gradually cooled to 4°C to give an air stable and colorless crystalline solid suitable for X-ray single-crystal diffraction studies.
55%	In methanol at 60℃; for 0.5h; Inert atmosphere;	4 2.3 Preparation of complexes General procedure: The complexes were prepared according to the following method [14]: 1mmol of copper(I) bromide or copper(I) chloride is stirred in methanol until complete dissolution. Then, 2.1 mmol of the corresponding phosphine ligand was added. The mixture was stirred at 60°C for 30min. under nitrogen atmosphere. A microcrystalline precipitate was obtained by concentration of the solution at reduced pressure. The solid product was dissolved in a dichloromethane/methanol mixture and the solution was gradually cooled to 4°C to give an air stable and colorless crystalline solid suitable for X-ray single-crystal diffraction studies.

Reference： [1]Espinoza, Sully; Arce, Pablo; San-Martín, Enrique; Lemus, Luis; Costamagna, Juan; Farías, Liliana; Rossi, Miriam; Caruso, Francesco; Guerrero, Juan [Polyhedron, 2014, vol. 85, p. 405 - 411]
[2]Espinoza, Sully; Arce, Pablo; San-Martn, Enrique; Lemus, Luis; Costamagna, Juan; Faras, Liliana; Rossi, Miriam; Caruso, Francesco; Guerrero, Juan [Polyhedron, 2015, vol. 85, p. 405 - 411]

52
[ 534-07-6 ]
[ 1038-95-5 ]
C₂₄H₂₅ClOP⁽¹⁺⁾*Cl^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	In benzene at 20℃; for 6h;	2.3.1 [CH₃COCH₂PPh₃]⁺Cl^- (1) General procedure: A solution consisting of triphenylphosphane (PPh3) (0.655g, 2.5mmol) and dichloroacetone, ClCH2COCH2Cl (2.5mmol, 0.318g) in benzene was stirred at room temperature for 6h. The resulting suspension was filtered off, and the obtained precipitate washed with diethyl either and benzene, and then dried to give [ClCH2COCH2PPh3]Cl as a white powder.

Reference： [1]Naghipour, Ali; Badpa, Khadijeh; Notash, Behrouz [Polyhedron, 2015, vol. 87, p. 349 - 353]

53
[ 26386-88-9 ]
[ 1038-95-5 ]
C₃₃H₃₁NO₃P₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	In toluene; at 20℃; for 1h;	The title compound was prepared using three differentapproaches of Staudinger reaction: (a) to a magnetically stirredsolution of diphenylphosphorylazide (0.5 ml, 2.13 mmol) in toluene(10 ml) was added dropwise a toluene (20 ml) solution oftri(p-tolyl)phosphine (0.5 g, 1.64 mmol). The mixture was stirredfor 1 h at room temperature. After 1 h (TLC control) the solventwas removed under reduced pressure and colorless oil wasobtained. Single colorless crystals of polymorph a (0.77 g, yield85%) were grown by slow solvent evaporation technique fromthe mother solution and diffusion of hexane. (b) In this case, theresulting mixture between toluene solutions of tri(p-tolyl)phosphineand diphenylphosphorylazide was heated under reflux for20 min. After the reaction, the mixture was gradually cooled downto ambient temperature. The solvent was removed under reducedpressure and pale yellow oil was obtained. Finally, colorless crystalsof polymorph (0.81 g, yield 89.5%) were obtained by slowsolvent evaporation technique from the mother solution and diffusionof hexane. (c) The reaction carried out in hexane, under reflux.After diphenylphosphorylazide addition a white precipitate wasobtained. The product (0.87 g, yield 96%) was collected by filtration,washed with cold hexane and dried in a vacuum.

Reference： [1]Journal of Molecular Structure,2015,vol. 1083,p. 389 - 397

54
[ 292638-85-8 ]
[ 1038-95-5 ]
[ 20754-20-5 ]

Yield	Reaction Conditions	Operation in experiment
55%	With silver(I) acetate; palladium diacetate; acetic acid In acetonitrile at 70℃; for 24h; Sealed tube;

Reference： [1]Lu, Dapeng; Xu, Yu; Liu, Wenjing; Guo, Lijuan; Sun, Xingxia [Helvetica Chimica Acta, 2015, vol. 98, # 1, p. 116 - 122]

55
(acetylacetonato)dicarbonylrhodium (l) [ No CAS ]
[ 121627-17-6 ]
[ 1038-95-5 ]
C₆₈H₆₆O₉P₃Rh [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With carbon monoxide; hydrogen; In toluene; at 100℃; under 18751.9 Torr; for 1h;Autoclave;	In an air atmosphere containing 200mL to gauge stainless steel autoclave was charged with [Rh (acac) (CO)2] (0.07mmol, 18.1mg) and 0.28mmol of a single phosphine ligands L4 and L12, 0.14mmol bidentate phosphite ligand, and 70mL of anhydrous toluene, connecting the gas line to a synthesis gas (hydrogen: carbon monoxide = 1: 1) after the autoclave was replaced three times the gas, the electromagnetic drive a mechanical stirrer, temperature of the autoclave was heated to 100 deg.] C, passed into the synthesis gas to a total pressure of 2.0MPa, at 100 , 2.0MPa reaction conditions 1h, to obtain a rhodium / (bidentate phosphite - single phosphine ligand) complex catalyst HRh (L12) (L4) (CO).

Reference： [1]Patent: CN105566081,2016,A .Location in patent: Paragraph 0054; 0055; 0056

56
[ 51803-78-2 ]
silver nitrate [ No CAS ]
[ 1038-95-5 ]
[Ag(nimesulide)(tri(p-tolyl)phosphine)₂] [ No CAS ]

Reference： [1]Inorganic Chemistry,2016,vol. 55,p. 8681 - 8696

57
Fe2(CO)6[μ-SCCHCHC(CH3)CHCS] [ No CAS ]
[ 1038-95-5 ]
C₃₃H₂₇Fe₂O₅PS₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
82%	With trimethylamine-N-oxide In acetonitrile at 20℃; for 1h; Schlenk technique; Inert atmosphere;	2.2. Synthesis of 2 General procedure: To a solution of 1 (0.2 mmol) and P(3-C6H4Cl)3 (0.2 mmol) in MeCN (15 mL) was added a solution of Me3NO·2H2O (0.2 mmol) in MeCN (5 mL). The mixture was stirred at room temperature for 1 h and then the solvent was reduced on a rotary evaporator and the residue was subjected to TLC separationusing CH2Cl2/petroleum ether = 1 : 3 (v/v) as eluent. The main red band gave 0.110 g (71%) of 2 as a red solid.

Reference： [1]Liu, Xu-Feng [Journal of Coordination Chemistry, 2016, vol. 69, # 17, p. 2620 - 2629]

58
[ 1038-95-5 ]
[ 18523-22-3 ]
C₂₉H₂₇BrOP⁽¹⁺⁾*Br^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
66%	In acetone at 25℃; for 12h;	2 2.2 Synthesis of [(p-tolyl)₃C(H)₂C(O)C₆H₄-m-Br]Br (S) 0.26g (1mmol) of tri(p-tolyl)phosphine was dissolved in 25ml acetone. Then, 0.26g (1mmol) of 2,3′-dibromoacetophenone was added to the solution. The resulting mixture was allowed to stir for 12h. After evaporation of the solvent and washing with petroleum benzene, white sediment was achieved. Yield: 66% (0.34g); Melting point: 209-210°C. The product was characterized on the basis of 1H, 31P, 13C NMR and CHN analysis data that well fitted its structure. Anal. Calc. for C29H27Br2OP: C, 59.82; H, 4.67. Found: C, 59.90; H, 4.81%. IR (KBr disk): ν (cm-1) 1681 (C=O), 1597, 1501, 1402, 1206, 1110, 855 (P-C), 802 and 782. 1H NMR (CDCl3): δ (ppm) 2.44 (9H, s, 3CH3), 6.14 (2H, d, 2JPH=21.32Hz, CH2); 7.02-8.41 (16H, m, Ph). 31P NMR (CDCl3): δ (ppm) 17.98. 13C NMR (CDCl3): δ (ppm) 21.79 (s, 3CH3); 38.73 (d, 1JPC=50.40Hz, CH); 121.52-146.23 (m, Ph); 191.29(CO).

Reference： [1]Sabounchei, Seyyed Javad; Ahmadianpoor, Mahmood; Hashemi, Ali; Mohsenzadeh, Fariba; Gable, Robert William [Inorganica Chimica Acta, 2017, vol. 458, p. 77 - 83]

59
[ 1422513-85-6 ]
[ 1038-95-5 ]
[μ-SCH(CH₃)CH(CH₃)S-μ]Fe₂(CO)₅[P(4-C₆H₄CH₃)₃] [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
64%	With trimethylamine-N-oxide In dichloromethane; acetonitrile at 20℃; for 1h;	4 2.2 Synthesis of (μ-SCH₂CH₂S-μ)Fe₂(CO)₅[P(4-C₆H₄F)₃] (1) General procedure: To a solution of (μ-SCH2CH2S-μ)Fe2(CO)6 (0.074g, 0.2mmol) and tris(4-fluorophenyl)phosphine (0.063g, 0.2mmol) in CH2Cl2 (10mL) was added a solution of Me3NO·2H2O (0.026g, 0.23mmol) in MeCN. The mixture was stirred at room temperature for 1h and then the solvent was reduced in vacuo and the residue was subjected to TLC separation using CH2Cl2/ petroleum ether (v/v=1:2) as eluent. From the main red band, 0.111g (84%) of complex 1 was obtained as a red solid.

Reference： [1]Liu, Xu-Feng [Polyhedron, 2016, vol. 119, p. 71 - 76]

60
[ 12279-09-3 ]
[ 1038-95-5 ]
[ 53127-35-8 ]

Reference： [1]Chemical Communications,2017,vol. 53,p. 3098 - 3101

61
[ 1038-95-5 ]
platinum(II) chloride [ No CAS ]
[Pt(μ-Cl)(CI)(P(C₆H₄Me-4)₃)]₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
93%	With acetonitrile In 5,5-dimethyl-1,3-cyclohexadiene at 140℃; for 22h;	2 Example 2: Preparation of [Pt(μ-Cl)(CI)(P(C₆H₄Me-4)₃)]₂ For the preparation of this compound PtCl2 (0.68 gram, 2.56 mmol) and P(C6H4Me2-4)3 (0.80 gram, 2.63 mmol) were reacted in a mixture of xylenes (15 mL) and MeCN (0.11 gram, 2.45 mmol) at 140 °C while stirring for 22 hours. After cooling to ambient temperature the reaction mixture was filtered over a glass-sintered filter. The solid residue was washed with heptane (10 mL) and dried at 50 °C for 4 hours. The product was obtained as a yellow-orange solid (1.36 gram, 1.19 mmol, 93 % yield on [Pt]) .

Reference： [1]Current Patent Assignee: ARKEMA - WO2017/109102, 2017, A1 Location in patent: Paragraph 086-087

62
[ 34767-55-0 ]
[ 1038-95-5 ]
bis((p-tolyl)₃phosphine)-κ²-acetylacetonatorhodium(I) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
0.81 g	In toluene; for 1.0h;Reflux; Inert atmosphere;	A suspension of acetylacetone (0.20g, 9mmol) and KOH (0.50g, 8.5mmol) in degassed THF (50mL) was added to a solution of [Rh(μ-Cl)(COE)2]2 (1.5g, 4.18mmol) in degassed THF (5mL) and the reaction mixture was stirred for 1.5hat room temperature. The volatiles were removed in vacuo and the resulting residue was extracted with hexane (25mL) to give, after evaporation of the solvent, [Rh(κ2-O,O-acac)(COE)2] [35]. The extract was added to a solution of P(p-tolyl)3 (2.52g, 8.3mmol) in degassed toluene (20ml). The reaction mixture was stirred and heated to reflux for 1h and then the solvent was removed in vacuo. Compound 1 was isolated as an orange solid. Yield: 0.81g (96%) 1H NMR (300MHz, C6D6, r.t., ppm) δ: 7.86 (m, 12H, CHarom), 6.80 (d, J=7Hz, 12H, CHarom), 5.38 (s, 1H, acac-CH), 2.00 (s, 18H, p-tolyl-CH3), 1.58 (s, 6H, acac-CH3). 31P{1H} NMR (121MHz, C6D6, r.t., ppm) δ: 54.8 (d, JRh-P=195Hz, 2P). Elem. Anal. Calcd. (%) for C47H49P2O2Rh: C, 69.63; H, 6.09. Found: C, 69.77; H, 6.50. MS (ES+) m/z=810 [M+].

Reference： [1]Journal of Organometallic Chemistry,2017,vol. 847,p. 184 - 192

63
[ 1038-95-5 ]
[ 797-70-6 ]
tri-p-tolylphosphoranylideneketene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: toluene / 18 h / 20 °C 2: sodium hydroxide / water 3: sodium amide / toluene / 24 h / Inert atmosphere; Reflux

Reference： [1]Aitken, R. Alan; Bjørnstad, Vidar; Massil, Tracy; Skramstad, Jan; Young, Robert J. [Arkivoc, 2017, vol. 2017, # 3, p. 293 - 301]

64
[ 1450-85-7 ]
[ 10025-98-6 ]
[ 1038-95-5 ]
[bis(tri-p-tolylphosphine)bis{pyrimidine-2(1H)-thione}]palladium(II) chloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%		All complexes were prepared by addition of 2 equivalents of tri-p-tolyl-phosphine dissolved in 15 mL of acetonitrile to the solution of K2[PdCl4] (0.326 g) in 15 mL of water followed by stirring. After 30 min 2 equiv. of hetero-cyclic thiones in 15 mL of methanol were added and the solutions were stirred for 1 h (Scheme 1). Yellow and red colorsolutions obtained were filtered off and filtrates were stored at room temperature for 3-5 days. Solid products were obtained from acetonitrile-methanol mixture upon slow evaporation.

Reference： [1]Russian Journal of General Chemistry,2017,vol. 87,p. 2073 - 2082

65
[ 91-13-4 ]
[ 1038-95-5 ]
(2-bromomethylbenzyl)tri(p-tolyl)phosphonium bromide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
91%	In benzene at 20℃; for 6h;	3 2.3 Synthesis of bis[(2-methylacetatobenzyl)tri(p-tolyl)phosphonium]hexabromodipalladate(II), [(CH₃C₆H₄)₃PCH₂C₆H₄CH₂OC(O)CH₃]₂[Pd₂Br₆] The phosphonium salt was synthesized via following procedure that described in the literature [17]. To a solution of 15 1,2-bis(bromomethyl)benzene (0.263g, 1mmol) in 16 benzene (2mL), a solution of 17 tri(p-tolyl)phosphine (P(p-tolyl)3) (0.304g, 1mmol) in benzene (2mL) was added and the resulting mixture was stirred for 6h at room temperature. The separated solid was filtered off and washed with diethyl ether (10mL) to give 18 (2-bromomethylbenzyl)tri(p-tolyl)phosphonium bromide, [(CH3C6H4)3PCH2C6H4CH2Br]Br, as a white powder. Yield: 0.502g (91%). M.p. 187°C. IR (υ, cm-1): 3045 (C-H stretch (aromatic)), 2955 (C-H stretch (alkyl)), 1447 (CH2-P)

Reference： [1]Ghorbani-Choghamarani, Arash; Naghipour, Ali; Heidarizadi, Fateme; Shirkhani, Roghayeh; Notash, Behrouz [Inorganica Chimica Acta, 2016, vol. 446, p. 97 - 102]

66
[ 15696-40-9 ]
[ 821-38-5 ]
[ 1038-95-5 ]
C₆₀H₆₆O₈Os₂P₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		A mixture of Os3(CO)12 (70.2 mg, 0.0774 mmol), tetradecanedioicacid (32.2 mg, 0.125 mmol), and 1,2-dichlorobenzene (7.0 mL)was irradiated and stirred at 200 C for 15 min. A pale yellow solutionwas formed. The solvent was removed and the solid residuewas transferred to a 100 mL flask using a mixture of chloroform(30 mL) and acetonitrile (5 mL). Tri-p-tolylphosphine (74.3 mg, 0.244 mmol) was added to the flask, and the mixture was refluxedand stirred under N2 for 1.5 h. The solvents were removed and theresidue was dissolved in CH2Cl2. TLC with an eluent of 1.8:1 hexanes/dichloromethane gave four bands. The top band (colorless,Rf = 0.96) consisted of trace amounts of Os4(m-H)4(CO)12. IR (nuCO,CHCl3): 2085 m; 2067 vs; 2020 s; 1998 w cm-1. Band 2 (yellow,Rf = 0.86) consisted of unreacted tri-p-tolylphosphine. Band 3(yellow, Rf = 0.76) comprised of 79.2 mg (50.2%) of cluster 5. IR (nuCO,CHCl3): 2085 w; 2067 w; 2011 vs; 1967 w; 1933 vs cm-1. 1H NMR(CDCl3): delta 1.06 (m, 20H), 1.81 (m, 4H), 2.36 (s, 18H), 7.24 (m, 24H).Anal. Calc. for C60H66O8P2Os2: C, 53.08; H, 4.90%. Found: C, 52.60; H,4.72%. Band 4 (yellow, Rf = 0.56) consisted of 4.4 mg of an unknowncompound. IR (nuCO, CHCl3): 2085 w; 2066 w; 2011 vs; 1967 m; 1934vs cm-1.

Reference： [1]Journal of Organometallic Chemistry,2017,vol. 849-850,p. 324 - 331

67
ruthenium trichloride [ No CAS ]
C₄₃H₄₂CuN₄P₂⁽¹⁺⁾*BF₄^(1-) [ No CAS ]
[ 1038-95-5 ]
C₈₅H₈₃Cl₂CuN₄P₄Ru⁽¹⁺⁾*BF₄^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88%	With sodium acetate In benzene at 100℃; for 24h; Inert atmosphere;	4 Example 4: Preparation of pyrimidinyl ruthenium copper heteronuclear compound (8): In a 50 ml three-necked flask equipped with a stirring reflux device was added 1.5 mmol of pyrimidylpyrazole copper bisphosphine compound D, 1 mmol of ruthenium trichloride, 3 mmol of tri-p-methylphenylphosphine, 1.5 mmol of sodium acetate and 20 ml of benzene. After heating at a temperature of 100 ° C for 24 hours under a nitrogen atmosphere, the mixture was cooled and filtered. The resulting solid was recrystallized from a mixed solvent of CH 2 Cl 2 and petroleum ether to give a product 8 in a yield of 88%.

Reference： [1]Current Patent Assignee: LUOYANG NORMAL UNIVERSITY - CN104327126, 2017, B Location in patent: Paragraph 0047; 0048; 0049

68
[ 7681-65-4 ]
[ 2456-81-7 ]
[ 1038-95-5 ]
[Cu₂I₂(tri-p-tolylphosphine)₂(4-pyrrolidinopyridine)₂] [ No CAS ]

Reference： [1]Inorganic Chemistry,2018,vol. 57,p. 5929 - 5938

69
[ 1038-95-5 ]
bis(4-methylphenyl)phosphonium bromide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
93%	With phosphorus tribromide; iron (III) bromide In tetrachloromethane at 0 - 70℃; for 12h;	2 Example 2 Synthesis of Bis(4-methylphenyl)phosphonium bromide Tris(4-methylphenyl)phosphine (1.1 mol, 334 g), 1 L of carbon tetrachloride, and iron bromide were added to the dry reactor(0.1 mol, 29.2 g), and phosphorus tribromide (0.5 mol, 134 g) was then added dropwise to the system at 0-10° C. After completion of the dropwise addition, the temperature was raised to 70° C. and reacted for 12 hours to stop the reaction. The reaction solution was filtered through Celite,The filtrate was distilled out of the solvent at atmospheric pressure, and then distilled under reduced pressure to obtain 407 g of bis(4-methylphenyl)phosphonium bromide in a yield of 93%.

Reference： [1]Current Patent Assignee: HENAN ACADEMY OF SCIENCES - CN107936056, 2018, A Location in patent: Paragraph 0016-0017

70
[ 1038-95-5 ]
[ 1019-71-2 ]

Yield	Reaction Conditions	Operation in experiment
91%	With zinc trifluoromethanesulfonate; phosphorus trichloride In tetrachloromethane at 0 - 60℃; for 12h;	3 Example 3 Synthesis of Bis(4-methylphenyl)phosphorus chloride Add tris(4-methylphenyl)phosphine (1.1 mol, 334 g), 1 L carbon tetrachloride, and trifluoromethyl to the dry reactorZinc alkanesulfonate (0.05 mol, 18.5 g) was added dropwise to the system at 0-10°C. Phosphorus trichloride (0.5 mol, 69 g) was added. After completion of the dropwise addition, the temperature was raised to 60°C for 12 hours to stop the reaction. . The reaction solution was filtered through celite, the filtrate was distilled out of the solvent at normal pressure, and then distilled under reduced pressure to obtain 339 g of di(4-methylphenyl)phosphorus chloride. The yield was 91%.

Reference： [1]Current Patent Assignee: HENAN ACADEMY OF SCIENCES - CN107936057, 2018, A Location in patent: Paragraph 0018-0019

71
[Fe₂(CO)₆{μ-SCH₂CH(CH₂O₂CCH₃)S}] [ No CAS ]
[ 1038-95-5 ]
C₃₁H₂₉Fe₂O₇PS₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
74%	With trimethylamine-N-oxide In dichloromethane; acetonitrile at 20℃; for 1h;	4 2.3. Synthesis of [{μ-SCH2CH(CH2O2CCH3)S}Fe2(CO)5(PPh3)] (3) General procedure: To a solution of 2 (0.044 g, 0.1 mmol) and triphenylphosphine(0.026 g, 0.1 mmol) in CH2Cl2 (5 mL) was added a solution ofMe3NO·2H2O (0.011 g, 0.1 mmol) in MeCN (5 mL). The mixture wasstirred at room temperature for 1 h and then the solvent wasreduced on a rotary evaporator. The residue was subjected to TLCseparation using CH2Cl2/petroleum ether =3:2 (v/v) as eluent.From the main red band, 0.059 g (87%) of complex 3 was obtainedas a red solid. IR (CH2Cl2, cm-1): νC≡O 2048 (νs),1987 (νs),1937 (m);νC=O 1740 (m). 1H NMR (500 MHz, CDCl3): 7.60-7.57 (m, 6H, PhH),7.44-7.43 (m, 9H, PhH), 3.79-3.75 (m, 2H, OCH2), 2.00 (s, 3H, CH3),1.78 (quint, J = 6.7 Hz, 1H, SCH), 1.43 (s, 2H, SCH2) ppm. 31P{1H}NMR (200 MHz, CDCl3, 85% H3PO4): 62.91 (s) ppm. 13C{1H} NMR(125 MHz, CDCl3): 214.65 (d, JP-C = 9 Hz, PFeC≡O), 214.41 (d, JP-C =8.1 Hz, PFeC≡O), 209.91 (FeC≡O), 170.26 (C=O), 135.58 (d, JP-C=39.4 Hz, i-PhC), 133.17 (d, JP-C = 9.5 Hz, o-PhC), 130.32 (s, p-PhC),128.63 (d, JP-C = 11.2 Hz, m-PhC), 65.97 (OCH2), 50.06 (SCH), 37.35(SCH2), 20.76 (CH3) ppm. Anal. Calcd for C28H23Fe2O7PS2: C, 49.58;H, 3.42. Found: C, 49.52; H, 3.26%.

Reference： [1]Lian, Meng; He, Jiao; Yu, Xiao-Yong; Mu, Chao; Liu, Xu-Feng; Li, Yu-Long; Jiang, Zhong-Qing [Journal of Organometallic Chemistry, 2018, vol. 870, p. 90 - 96]

72
[ 1038-95-5 ]
[ 4714-24-3 ]
tris(p-tolyl)-(4-(2-phenylethenyl)phenyl)phosphonium bromide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
92%	With nickel(II) chloride hexahydrate In 1,2-dimethoxyethane at 165℃; for 24h;	3 [Synthesis Example 3]Synthesis of tris (p-tolyl) -4- (2-phenylethenyl) phenylphosphonium bromide In a flask equipped with a stirrer,2.4 g (8.0 mmol) of tris (p-tolyl) phosphine,0.2 g (0.9 mmol) of nickel chloride hexahydrate,1-bromo-4- (2-phenylethenyl) benzene,2.3 g (8.8 mmol), ethylene glycol 14.6 g was added,And reacted at 165 ° C. for 24 hours. The reaction solution was cooled to room temperature,12.2 g of water,18.3 g of dichloromethane was added and the liquid separation operation was carried out,The organic layer was separated.After washing the organic layer twice with 14.6 g of water, the solvent was distilled off under reduced pressure,Tris (p-tolyl) -4- (2-phenylethenyl) phenyl) phosphonium bromide in a slightly yellow powder form4.1 g was obtained(Yield 92%).

Reference： [1]Current Patent Assignee: SUMITOMO CHEMICAL COMPANY LIMITED; Sumitomo Chemical (w/o Dongwoo Fine-Chem) - JP2018/168137, 2018, A Location in patent: Paragraph 0111; 0112

73
[ 1038-95-5 ]
[ 75-05-8 ]
[ 797-70-6 ]
C₁₆H₁₆NP [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1: > 26 %Chromat. 2: 16 %Chromat.	at 20℃; for 3h; Inert atmosphere; Irradiation;

Reference： [1]Yasui, Shinro; Ando, Taro; Ozaki, Masashi; Ogawa, Yuya; Shioji, Kosei [Heteroatom Chemistry, 2018, vol. 29, # 5-6]

74
[ 15696-40-9 ]
[ 802294-64-0 ]
[ 1038-95-5 ]
bis(μ-propanoato-1κO:2κO')bis[tris(4-methylphenyl)phosphane]-1κP,2κP-bis(dicarbonylosmium) [ No CAS ]
Os2(μ-H)₄(CO)₁₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1: 7.4 mg 2: 55.5%	Stage #1: dodecacarbonyl triosmium; propionic acid at 185℃; for 0.166667h; Microwave irradiation; Stage #2: Tri(p-tolyl)phosphine In chloroform; acetonitrile for 0.916667h; Reflux;	2.2.3. Synthesis of (4) General procedure: A mixture of Os3(CO)12 (49.4 mg,0.0545 mmol) and acetic acid (7 ml) was stirred and irradiatedin a microwave reactor at 185 °C for 10 min. The excess acidwas evaporated under a stream of air and the residue wasredissolved in a mixture of chloroform (25 ml) and acetonitrile(3 ml). Tri-p-tolylphosphane (81.7 mg, 0.268 mmol) was addedand the solution refluxed for 55 min. The solvent was removedand the residue dissolved in CH2Cl2. Three bands were collected after TLC with an eluent of 1.25:1 hexanes-CH2Cl2. The first and second bands contained 2.7 mg of Os4(μ-H)4-(CO)12 and 7.1 mg of (2), respectively. Band 3 consisted of54.0 mg (54.1% yield) of (4).

Reference： [1]Wilson, Kylie M.; Swartout, John W.; Touchton, Henry A.; Lambert, Erica N.; Johnstone, James E.; Archambeau, Ashley K.; Marolf, David M.; Mikeska, Emily R.; Lynch, Vincent M.; Nesterov, Vladimir N.; Reinheimer, Eric W.; Powell, Gregory L.; Powell, Cynthia B. [Acta Crystallographica Section C: Structural Chemistry, 2019, vol. 75, # 5, p. 529 - 537]

75
[ 19226-36-9 ]
[ 1038-95-5 ]
[ 78450-40-5 ]

Yield	Reaction Conditions	Operation in experiment
94%	With iron(III) chloride In toluene at 100℃; for 1h; Schlenk technique; Irradiation;	10 Example 10: Synthesis of N-[tris(4-methylphenyl)-λ5-phosphazene]benzamide Accurately weigh 3-phenyl-1,4,2-dioxazol-5-one (48.9mg, 0.3mmol), tris(p-tolyl)phosphine(121.7mg, 0.4mmol), ferric chloride (4.8mg, 10mol%) was added to the 25mL Schlenk reaction bottle, then added to ABenzene (2 mL) was reacted at 100 ° C for 1 h under light conditions (10 W, 480 nm). After the reaction is completed, the solvent is removed under reduced pressure and oil is used.The ether/ethyl acetate was used as an eluent and was separated on a silica gel column. The yield of the product was 94%.
94%	With tris(triphenylphosphine)ruthenium(II) chloride In toluene at 100℃; for 1h; Schlenk technique; Irradiation;	10 Example 10: Synthesis of N-[tris(4-methylphenyl)-λ5-phosphazene]benzamide Accurately weighed 3-phenyl-1,4,2-dioxazol-5-one (48.9 mg, 0.3 mmol),Tris(p-tolyl)phosphine (121.7 mg, 0.4 mmol) and tris(triphenylphosphine)phosphonium chloride (28.7 mg, 10 mol%) were added to a 25 mL Schlenk reaction flask.Then add toluene (2 mL),The reaction was carried out at 100 ° C for 1 h under light conditions (10 W, 480 nm). After the reaction is completed, the pressure is removed.Solvent, using petroleum ether / ethyl acetate as eluent on a silica column, the product yield was 94%.
94%	With cadmium(II) sulphide In toluene at 100℃; for 1h; Schlenk technique;	10 Example 10: Synthesis of N-[tris(4-methylphenyl)-λ5-phosphoramido]benzamide Accurately weighed 3-phenyl-1,4,2-dioxazol-5-one (48.9 mg, 0.3 mmol),Tris(p-tolyl)phosphine (121.7 mg, 0.4 mmol),Cadmium sulfide (4.3 mg, 10 mol%) was added to a 25 mL Schlenk reaction flask.Then add toluene (2 mL),The reaction was carried out at 100 ° C for 1 h under light conditions (10 W, 480 nm).After the reaction,The solvent was removed under reduced pressure.Using petroleum ether/ethyl acetate as the eluent,Separated by silica gel column,The yield of the product was 94%.

94%	With iron(III) chloride In toluene at 100℃; for 1h; Irradiation; Schlenk technique;	10 Synthesis of N-[Tris(4-methylphenyl)-λ5-phosphoranylidene]benzamide Accurately weigh 3-phenyl-1,4,2-dioxazol-5-one (48.9mg, 0.3mmol), tris(p-tolyl)phosphine (121.7mg, 0.4mmol), ferric chloride (4.8mg , 10mol%) was added to a 25mL Schlenk reaction flask, then toluene (2mL) was added, and the reaction was carried out at 100°C under light conditions (10W, 480nm) for 1 hour. After the reaction, the solvent was removed under reduced pressure, petroleum ether/ethyl acetate was used as the eluent, and the silica gel column was used for separation. The yield of the product was 94%.
94%	With iron(III) chloride In dichloromethane at 20℃; for 0.25h; Inert atmosphere; Irradiation; Glovebox; regioselective reaction;

Reference： [1]Current Patent Assignee: DALIAN UNIVERSITY OF TECHNOLOGY - CN109762017, 2019, A Location in patent: Paragraph 0065-0066
[2]Current Patent Assignee: DALIAN UNIVERSITY OF TECHNOLOGY - CN109762018, 2019, A Location in patent: Paragraph 0064-0065
[3]Current Patent Assignee: DALIAN UNIVERSITY OF TECHNOLOGY - CN109796492, 2019, A Location in patent: Paragraph 0064-0067
[4]Current Patent Assignee: DALIAN UNIVERSITY OF TECHNOLOGY - CN112142792, 2020, A Location in patent: Paragraph 0069-0073
[5]Tang, Jing-Jing; Yu, Xiaoqiang; Wang, Yi; Yamamoto, Yoshinori; Bao, Ming [Angewandte Chemie - International Edition, 2021, vol. 60, # 30, p. 16426 - 16435][Angew. Chem., 2021, vol. 133, # 30, p. 16562 - 16571]

76
[ 88-73-3 ]
[ 1038-95-5 ]
[ 70680-21-6 ]

Yield	Reaction Conditions	Operation in experiment
78%	With P(p-CH₃OC₆H₄)3; palladium diacetate; caesium carbonate In N,N-dimethyl-formamide at 90℃; for 6h; Inert atmosphere;	Cross-coupling of 1b with triarylbismuth reagents: (Table 3). General procedure: The representativecross-coupling procedure given for Table 2 was followed with the followingreagents and conditions: arylchloride 1b (0.875 mmol, 3.5 equiv.), BiAr3(0.25 mmol, 1 equiv.), Pd(OAc)2 (0.025 mmol, 0.1 equiv.), P(p-anisyl)3(0.1 mmol, 0.4 equiv.), Cs2CO3 (0.75 mmol, 3 equiv.) and DMF (3 mL) at 90 Cfor 6h.

Reference： [1]Rao, Maddali L.N.; Meka, Suresh [Tetrahedron Letters, 2019, vol. 60, # 34]

77
[Fe₂(CO)₆{μ-SCH₂CH(CH₂CH₃)S}] [ No CAS ]
[ 1038-95-5 ]
pentacarbonyl(butane-1,2-dithiolato)tris(4-methylphenyl)phosphinodiiron(I) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
81%	With trimethylamine-N-oxide In dichloromethane; acetonitrile at 20℃; for 1h;	2.2. Synthesis of pentacarbonyl(butane-1,2-dithiolato)tris(4-methylphenyl)phosphinodiiron(I) (2) To a solution of [Fe2(CO)6{m-SCH2CH(CH2CH3)S}] (0.040 g, 0.10 mmol) and tris(4-methylphenyl)phosphine (0.030 g, 0.099 mmol) in CH2Cl2 (5 mL) was added a solution ofMe3NO2H2O (0.011 g, 0.099 mmol) in MeCN (5 mL). The mixture was stirred at roomtemperature for 1 h, and then, the solvent was reduced on a rotary evaporator. Theresidue was subjected to TLC using CH2Cl2/petroleum ether 1:4 (v/v) as eluent.From the main red band, 0.055 g (81%) of 2 was obtained as a red solid. IR (CH2Cl2,cm1): mCO 2041 (vs), 1981 (vs), 1932 (m). 1H NMR (500 MHz, CDCl3): 7.40 (s, 4H, PhH),6.93, 6.85 (2s, 8H, PhH), 3.53 (s, 9H, 3CH3), 1.54 (s, 2H, SCH2), 1.26 (s, 2H, CH2), 1.00 (s,1H, SCH), 0.71 (s, 3H, CH2CH3) ppm. 31P{1H} NMR (200 MHz, CDCl3, 85% H3PO4): 50.37(s) ppm. Anal. Calcd for C30H29Fe2O5PS2: C, 53.28; H, 4.32. Found: C, 52.98; H, 4.44%.

Reference： [1]Lin, Hui-Min; Mu, Chao; Li, Ao; Liu, Xu-Feng; Li, Yu-Long; Jiang, Zhong-Qing; Wu, Hong-Ke [Journal of Coordination Chemistry, 2019, vol. 72, # 15, p. 2517 - 2530]

78
μ-(1,2-ethanedithilato)diironhexacarbonyl [ No CAS ]
[ 1038-95-5 ]
[ 1598427-34-9 ]

Yield	Reaction Conditions	Operation in experiment
83%	With trimethylamine-N-oxide In dichloromethane; acetonitrile at 20℃; for 11h;	2.2. Synthesis of pentacarbonyl(ethane-1,2-dithiolato)tris(4-methylphenyl)phosphinodiiron(I) (2) To a solution of [Fe2(CO)6(m-SCH2CH2S)] (0.037 g, 0.1 mmol) and tris(4-methylphenyl)-phosphine (0.032 g, 0.1 mmol) in CH2Cl2 (5 mL) was added a solution of Me3NO2H2O(0.011 g, 0.1 mmol) in MeCN (5 mL). The mixture was stirred at room temperature for1 h and then the solvent was reduced on a rotary evaporator. The residue was subjectedto TLC using CH2Cl2/petroleum ether1:5 (v/v) as eluent. From the main redband, 0.054 g (83%) of 2 was obtained as a red solid. IR (CH2Cl2, cm-1): mCO 2042 (vs),1992 (vs), 1968 (vs), 1939 (vs). 1H NMR (500 MHz, CDCl3): 7.44 (dd, J8, 10 Hz, 6 H,PhH), 7.20 (d, J7 Hz, 6 H, PhH), 2.38 (s, 9 H, 3CH3), 1.85 (d, J7.5 Hz, 2 H, SCH2), 1.16(d, J7.5 Hz, 2 H, SCH2) ppm. 31P{1H} NMR (200 MHz, CDCl3, 85% H3PO4): 60.53 (s)ppm. 13C{1H} NMR (125 MHz, CDCl3): 215.08 (d, JP-C8.9 Hz, PFeCO), 210.25 (FeCO),140.28 (s, p-PhC), 133.04 (d, JP-C11.5 Hz, o-PhC), 132.90 (d, JP-C41.4 Hz, i-PhC),129.25 (d, JP-C10 Hz, m-PhC), 34.87 (SCH2), 21.36 (CH3) ppm. Anal. Calcd. forC28H25Fe2O5PS2: C, 51.88; H, 3.89. Found: C, 52.02; H, 3.82%.

Reference： [1]Yan, Lin; He, Jiao; Liu, Xu-Feng; Li, Yu-Long; Jiang, Zhong-Qing; Wu, Hong-Ke [Journal of Coordination Chemistry, 2019, vol. 72, # 15, p. 2531 - 2543]

79
11-bromo-N-(2-(sec-butyl)-1,3-dioxoisoindolin-4-yl)undecanamide [ No CAS ]
[ 1038-95-5 ]
(11-((2-(sec-butyl)-1,3-dioxoisoindolin-4-yl)amino)-11-oxoundecyl)tri-p-tolylphosphonium bromide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
96%	With triphenylphosphine In acetonitrile for 72h; Reflux;	9 Example 9 - Synthesis of (1 l-((2-(.vee-butyl)-L3-diQxoisoindolin-4-yl)amino)-l 1 (0228) oxoundecyl)tri-p-tolylphosphonium bromide (intermediate) (0229) 22d (0230) A solution of lib (400 mg, 0.86 mmol) and tri(p-tolyl)phosphine (785 mg, 2.58 mmol) in dry CH3CN (7 mL) was refluxed for 72 hours. The mixture was concentrated in vacuo and the residue was purified by flash chromatography (5% MeOH/DCM) to afford the title compound 22d (636 g, 96%) as a white solid.
63%	In acetonitrile for 72h; Reflux; Inert atmosphere;	3.2.6. General Procedure for the Synthesis of Phosphonium Phthalimides General procedure: A solution of the bromide (1 mmol) and the phosphine (2 mmol) in dry acetonitrile (5 mL) was refluxed under Ar for 3 days. After cooling, the solvent was evaporated and the residue was subjected to column chromatography, yielding the corresponding phosphonium cation.

Reference： [1]Current Patent Assignee: GOVERNMENT OF SPAIN; POLYTECHNIC UNIVERSITY OF VALENCIA - WO2019/243757, 2019, A1 Location in patent: Page/Page column 37-38
[2]Pantelia, Anna; Daskalaki, Ira; Consuelo Cuquerella; Rotas, Georgios; Miranda, Miguel A.; Vougioukalakis, Georgios C. [Molecules, 2019, vol. 24, # 21]

80
[ 106-43-4 ]
[ 1038-95-5 ]

Yield	Reaction Conditions	Operation in experiment
72.48%	Stage #1: para-chlorotoluene With magnesium In 2-methyltetrahydrofuran at 25 - 55℃; for 2h; Stage #2: With phosphorus trichloride In 2-methyltetrahydrofuran at 25 - 85℃; for 3h; Stage #3: With hydrogenchloride In 2-methyltetrahydrofuran; water for 1.5h;	1; 3 Continuously pour dry nitrogen into the clean reactor,Put magnesium chips 4.86g (0.2mol),P-chlorotoluene 3.80g (0.03mol),15.33g of solvent was added to the reactor.The temperature was increased by stirring, and the reaction was initiated at 42°C. Drop the pre-prepared p-chlorotoluene solution (p-chlorotoluene 21.52g (0.17mol), 2-methyltetrahydrofuran 65.02g),Control the temperature around 55.After 1h addition, the temperature will be reduced to about 25 after 1h addition. Keep the temperature of the kettle around 25,Drop the pre-prepared phosphorus trichloride solution (phosphorus trichloride 8.25g (0.18mol), 2-methyltetrahydrofuran 20.21g),After adding in 1h, after adding and keeping warm for 1h, cool down and set aside. Maintain a pressure of about -0.3MPa in the kettle,Slowly increase the temperature of the kettle, and the internal temperature will reach about 85 in about 1 hour.After desolvation is over, the vacuum is broken by nitrogen, and the temperature is lowered for use. Add 45 g of hydrochloric acid with a concentration of 5% dropwise, and keep it for 0.5h after 1h. Cool the reaction solution to 10°C and filter;Rinse the filter cake with water and methanol and drain it;Place the filter cake in a vacuum dryer at 60°C and dry for 2 hours to obtain tris-(4-tolyl)phosphine.The yield is 72.48%, which is off-white powder,The content detected by HPLC was 99.37%, as shown in Figure 1.
20%	With 1-methyl-pyrrolidin-2-one; potassium hydroxide monohydrate; phosphorus at 100 - 112℃; for 1h; Inert atmosphere;

Reference： [1]Current Patent Assignee: JIANGSU FUBIYA CHEMICALS - CN111825715, 2020, A Location in patent: Paragraph 0049-0055; 0063-0064
[2]Malysheva, Svetlana F.; Kuimov, Vladimir A.; Belogorlova, Natalia A.; Albanov, Alexander I.; Gusarova, Nina K.; Trofimov, Boris A. [European Journal of Organic Chemistry, 2019, vol. 2019, # 36, p. 6240 - 6245]

81
[ 42516-72-3 ]
[ 1038-95-5 ]
C₆₃H₆₇P₃Ru [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
74%	With hydrogen In tetrahydrofuran at 20℃; for 3h;

Reference： [1]Bordet, Alexis; Estes, Deven P.; Leitner, Walter; Leutzsch, Markus; Schubert, Lukas [ACS Catalysis, 2020, vol. 10, # 5, p. 2990 - 2998]

82
[ 15696-40-9 ]
[ 64-19-7 ]
[ 802294-64-0 ]
[ 1038-95-5 ]
bis(μ-propanoato-1κO:2κO')bis[tris(4-methylphenyl)phosphane]-1κP,2κP-bis(dicarbonylosmium) dichloromethane monosolvate [ No CAS ]
6CO*2Os*2C₃H₅O₂^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1: 55.5% 2: 7.4 mg	Stage #1: dodecacarbonyl triosmium; acetic acid; propionic acid at 185℃; for 0.166667h; Microwave irradiation; Stage #2: Tri(p-tolyl)phosphine In chloroform; acetonitrile for 0.916667h; Reflux;	2.2.3. Synthesis of (4). A mixture of Os3(CO)12 (49.4 mg,0.0545 mmol) and acetic acid (7 ml) was stirred and irradiatedin a microwave reactor at 185 C for 10 min. The excess acidwas evaporated under a stream of air and the residue wasredissolved in a mixture of chloroform (25 ml) and acetonitrile(3 ml). Tri-p-tolylphosphane (81.7 mg, 0.268 mmol) was addedand the solution refluxed for 55 min. The solvent was removedand the residue dissolved in CH2Cl2. Three bands werecollected after TLC with an eluent of 1.25:1 hexanes-CH2Cl2.The first and second bands contained 2.7 mg of Os4(-H)4-(CO)12 and 7.1 mg of (2), respectively. Band 3 consisted of54.0 mg (54.1% yield) of (4). IR (CO, CHCl3): 2011 (vs), 1967(w), 1934 (vs) cm1. 1H NMR (CDCl3): 7.35 (m, 24H), 2.36(m, 18H), 1.60 (t, 6H). Analysis calculated (%) for C50H48-O8Os2P2: C 49.25, H 3.97; found: C 50.02, H 4.08. Singlecrystals were obtained by slow evaporation of a p-xylenesolution at ambient temperature.

Reference： [1]Archambeau, Ashley K.; Johnstone, James E.; Lambert, Erica N.; Lynch, Vincent M.; Marolf, David M.; Mikeska, Emily R.; Nesterov, Vladimir N.; Powell, Cynthia B.; Powell, Gregory L.; Reinheimer, Eric W.; Swartout, John W.; Touchton, Henry A.; Wilson, Kylie M. [Acta Crystallographica Section C: Structural Chemistry, 2019, vol. 75, p. 529 - 537]

83
[ 3375-31-3 ]
[ 106-95-6 ]
[ 1038-95-5 ]
Pd[P(p-Me-Ph)₃](η₃-C₃H₅)Br [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With potassium <i>tert</i>-butylate In 1,2-dichloro-ethane at 80℃; for 24h; Inert atmosphere;	2 Example 2 Preparation of tri(p-methylphenyl)phosphine allyl palladium bromide and its derivatives Step 1: Add 36mg palladium acetate and 97mg tris(p-methylphenyl)phosphine to the reaction tube,77mg allyl bromide, 45mg potassium tert-butoxide, 1mL 1,2 dichloroethane, under a nitrogen atmosphere, heated to 80 for 24h.The remaining steps are the same as in Example 1. A divalent palladium yellow solid (product II) is obtained with a yield of up to 80%.The yellow solid was recrystallized from dichloromethane/diethyl ether to obtain a yellow crystal product with the structural formula {Pd[P(p-Me-Ph)3](η3-C3H5)Br}, which was recorded as sample 2.

Reference： [1]Current Patent Assignee: CHINESE ACADEMY OF SCIENCES - CN111116666, 2020, A Location in patent: Paragraph 0111-0117

84
[ 917-92-0 ]
[ 1038-95-5 ]
C₂₇H₃₂P⁽¹⁺⁾*F₆P^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
77%	With ammonium hexafluorophosphate; [4,4′-bis(1,1-dimethylethyl)-2,2′-bipyridine-N1,N1′]bis{3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-κN]phenyl-κC}iridium(III) hexafluorophosphate In acetonitrile at 20℃; for 20h; Inert atmosphere; Sealed tube; Irradiation;	Reaction procedure General procedure: To an oven-dried 4 mL vial equipped with a stirrer bar, Ir catalyst (1.1 mg, 0.001mmol, 0.5 mol%) and 1 (52.2 mg, 0.20 mmol) were added. The vial was purged withargon gas and capped with a silicon-sealed open-top screw cap. Alkyne 2 (32.5 mg, 0.40mmol, 2.0 equiv) and anhydrous acetonitrile (3.0 mL) were added into the vial viasyringe through the silicon-sealed cap. The mixture was stirred under photoirradiation(470 nm) at room temperature for 20 hours. After irradiation, the solvent was removedunder reduced pressure and the residue was purified by preparative thin-layerchromatography (CHCl3/MeOH = 10/1) to afford the product 3 as white solids (83.5 mg,0.17 mmol, 86% yield).

Reference： [1]Masuda, Yusuke; Ikeshita, Daichi; Murakami, Masahiro [Chemistry Letters, 2021, vol. 50, # 9, p. 1691 - 1694]

85
[ 24067-17-2 ]
[ 1038-95-5 ]
[ 613-33-2 ]
[ 1528-74-1 ]
[ 2143-88-6 ]

Yield	Reaction Conditions	Operation in experiment
1: 23% 2: 14% 3: 33%	With palladium diacetate In acetonitrile at 35℃; for 24h; Schlenk technique; Inert atmosphere;	4.1.2. Typical procedure General procedure: A solution of aryl boronic acid (1 molar equiv.) and PAr3 (1 molarequiv.) in acetonitrile (8.0 mL per 0.38 mmol of RB(OH)2) was placed ina Schlenk flask. Then Pd(OAc)2 (0.3 molar equiv.) was added. The reactionmixture was stirred at 35 C for 24 h. The reaction progress wasmonitored by TLC (1:4 EtOAc-hexanes). The reaction mixture wasfiltered through celite to remove insoluble materials, celite was washedwith dichloromethane. The filtrate was concentrated under reducedpressure. The resulting residue was dissolved in MeOH-CH2Cl2 (1:20)and loaded on to preparative TLC plate. A 3:7 mixture of EtOAc-hexaneswas used as an eluent for the purification unless otherwise mentioned.Two pure compounds were isolated from the TLC plate: 8-phenylquinoline(3a, 19%) and biphenyl (6, 2%).

Reference： [1]Enright, Dale R.; Gogate, Akash R.; Smoliakova, Irina P.; Vasireddy, Purna C. R. [Polyhedron, 2022, vol. 211]

86
ibuprofen-bromopentanol ester [ No CAS ]
[ 1038-95-5 ]
C₃₉H₄₈O₂P⁽¹⁺⁾ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%	With sodium iodide In acetonitrile for 24h; Reflux;	Synthesis of compound 8b: Compound (7) 50 mg (0.141 mmol) and sodium iodide 84.54 mg (0.564 mmol) were dissolved in 2 mL acetonitrile. Tris(p-tolyl) phosphine 171.4 mg (0.564 mmol) was added to the mixture. The reaction was stirred under reflux for 24 hours. After completion, (monitored by TLC in 5% DCM in methanol) acetonitrile was removed under reduced pressure and resulted residue was purified by column chromatography on silica gel (100-200 mesh) eluting with DCM:MeOH:AcOH (98:2:0.5) solvent system.Yield = 78%.
78%	With sodium iodide In acetonitrile for 24h; Reflux;	Synthesis of compound 8b: Compound (7) 50 mg (0.141 mmol) and sodium iodide 84.54 mg (0.564 mmol) were dissolved in 2 mL acetonitrile. Tris(p-tolyl) phosphine 171.4 mg (0.564 mmol) was added to the mixture. The reaction was stirred under reflux for 24 hours. After completion, (monitored by TLC in 5% DCM in methanol) acetonitrile was removed under reduced pressure and resulted residue was purified by column chromatography on silica gel (100-200 mesh) eluting with DCM:MeOH:AcOH (98:2:0.5) solvent system.Yield = 78%.

Reference： [1]Bajpai, Aman; Basu, Sudipta; Chhabria, Dimple; Deepshikha; Kirubakaran, Sivapriya; Mishra, Tripti [Bioorganic and Medicinal Chemistry, 2022, vol. 64]
[2]Bajpai, Aman; Basu, Sudipta; Chhabria, Dimple; Deepshikha; Kirubakaran, Sivapriya; Mishra, Tripti [Bioorganic and Medicinal Chemistry, 2022, vol. 64]

87
C₂₄H₂₅BrClNO₄ [ No CAS ]
[ 1038-95-5 ]
C₄₅H₄₆ClNO₄P⁽¹⁺⁾ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%	With sodium iodide In acetonitrile for 24h; Reflux;	Synthesis of compound 5b: In a 25 mL round bottom flask, compound 3 (50 mg, 0.099 mmol) and sodium iodide (60 mg, 0.297 mmol) were dissolved in acetonitrile 3 mL. The resulting reaction mixture was stirred under reflux for 15 minutes. Tris(p-tolyl) phosphine (90.4 mg, 0.297 mmol) was then added to the solution. The reaction was kept stirring for additional 24 hours under reflux conditions. After completion of the reaction, (monitored by TLC in 5% DCM in methanol) acetonitrile was removed under reduced pressure, and resulted residue was purified by column chromatography on silica gel (100-200 mesh) eluting with DCM:MeOH:AcOH (97:2.5:0.5) solvent system.Yield = 78%.
78%	With sodium iodide In acetonitrile for 24h; Reflux;	Synthesis of compound 5b: In a 25 mL round bottom flask, compound 3 (50 mg, 0.099 mmol) and sodium iodide (60 mg, 0.297 mmol) were dissolved in acetonitrile 3 mL. The resulting reaction mixture was stirred under reflux for 15 minutes. Tris(p-tolyl) phosphine (90.4 mg, 0.297 mmol) was then added to the solution. The reaction was kept stirring for additional 24 hours under reflux conditions. After completion of the reaction, (monitored by TLC in 5% DCM in methanol) acetonitrile was removed under reduced pressure, and resulted residue was purified by column chromatography on silica gel (100-200 mesh) eluting with DCM:MeOH:AcOH (97:2.5:0.5) solvent system.Yield = 78%.

Reference： [1]Bajpai, Aman; Basu, Sudipta; Chhabria, Dimple; Deepshikha; Kirubakaran, Sivapriya; Mishra, Tripti [Bioorganic and Medicinal Chemistry, 2022, vol. 64]
[2]Bajpai, Aman; Basu, Sudipta; Chhabria, Dimple; Deepshikha; Kirubakaran, Sivapriya; Mishra, Tripti [Bioorganic and Medicinal Chemistry, 2022, vol. 64]

88
[ 115262-01-6 ]
[ 1038-95-5 ]
C₂₃H₂₃F₄P [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%	With sodium tetrahydridoborate; Potassium bicarbonate In dichloromethane; lithium hydroxide monohydrate at 20℃; Inert atmosphere; Sealed tube;	2 Example 2 The product prepared by the present embodiment, the structure is:The preparation method of the present embodiment is as follows: under a nitrogen atmosphere, in a 10 mL sealed tube equipped with a magnetron, add tri(p-methylphenyl)phosphine (30.4 mg, 0.1 mmol), potassium bicarbonate (50 mg, 0.5 mmol) and Sodium borohydride (11.35 mg, 0.2 mmol), dichloromethane (1 mL), bromodifluoromethyltrimethylsilane (45 μL, 0.4 mmol) and water (7.2 μL, 0.4 mmol) were added to the reaction, respectively .After sealing the reaction tube, it was transferred to room temperature and stirred to carry out the reaction, and the reaction progress was detected by TLC plate.After the reaction was complete, the reaction mixture was filtered, washed with dichloromethane to remove the filter residue, the dichloromethane mixture was distilled under reduced pressure, the solvent was evaporated, and the solvent was evaporated under reduced pressure to obtain the crude reaction product, which was separated by column chromatography to obtain fluorine-containing Pentavalent phosphorus compound, white solid 3ab (31.5 mg, 76%).

Reference： [1]Current Patent Assignee: UNIV XI AN JIAOTONG - CN114249765, 2022, A Location in patent: Paragraph 0059-0065

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
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CAS No. :	1038-95-5	MDL No. :	MFCD00008542
Formula :	C₂₁H₂₁P	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	WXAZIUYTQHYBFW-UHFFFAOYSA-N
M.W :	304.37	Pubchem ID :	13956
Synonyms :

Num. heavy atoms :	22
Num. arom. heavy atoms :	18
Fraction Csp3 :	0.14
Num. rotatable bonds :	3
Num. H-bond acceptors :	0.0
Num. H-bond donors :	0.0
Molar Refractivity :	100.05
TPSA :	13.59 Å²

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	Yes
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-4.11 cm/s

Log Po/w (iLOGP) :	4.05
Log Po/w (XLOGP3) :	5.7
Log Po/w (WLOGP) :	4.37
Log Po/w (MLOGP) :	5.85
Log Po/w (SILICOS-IT) :	6.99
Consensus Log Po/w :	5.39

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Safety of [ 1038-95-5 ]

Application In Synthesis of [ 1038-95-5 ]

[ 1038-95-5 ] Synthesis Path-Downstream 1~88

Related Functional Groups of
[ 1038-95-5 ]

Aryls

Phosphoruses

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Lipinski :	1.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	2.0
Bioavailability Score :	0.55

Log S (ESOL) :	-5.73
Solubility :	0.000573 mg/ml ; 0.00000188 mol/l
Class :	Moderately soluble
Log S (Ali) :	-5.75
Solubility :	0.000539 mg/ml ; 0.00000177 mol/l
Class :	Moderately soluble
Log S (SILICOS-IT) :	-8.69
Solubility :	0.000000621 mg/ml ; 0.000000002 mol/l
Class :	Poorly soluble

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	3.99

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

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

[ CAS No. 1038-95-5 ] {[proInfo.proName]}

Quality Control of [ 1038-95-5 ]

Related Doc. of [ 1038-95-5 ]

Product Details of [ 1038-95-5 ]

Calculated chemistry of [ 1038-95-5 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 1038-95-5 ]

Application In Synthesis of [ 1038-95-5 ]

[ 1038-95-5 ] Synthesis Path-Downstream 1~88

Related Functional Groups of [ 1038-95-5 ]

Aryls

Phosphoruses

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 1038-95-5 ]