[ CAS No. 70127-50-3 ] {[proInfo.proName]}

Name: 70127-50-3|(2-Hydroxybenzyl)diphenylphosphine oxide|98%
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Quality Control of [ 70127-50-3 ]

COA NMR CNMR HPLC LC-MS

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Product Details of [ 70127-50-3 ]

CAS No. :	70127-50-3	MDL No. :	MFCD00406515
Formula :	C₁₉H₁₇O₂P	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	NQWHOPCJTGVYOX-UHFFFAOYSA-N
M.W :	308.31	Pubchem ID :	796918
Synonyms :

Safety of [ 70127-50-3 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P301+P312-P302+P352-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 70127-50-3 ]

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

Downstream synthetic route of [ 70127-50-3 ]

[ 70127-50-3 ] Synthesis Path-Downstream 1~50

1
[ 1112-37-4 ]
[ 70127-50-3 ]
[ 156422-11-6 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine In benzene for 1h; from RT to reflux;

Reference： [1]Bovin, Alexander N.; Yarkevich, Alla N.; Kharitonov, Alexander V.; Tsvetkov, Eugene N. [Journal of the Chemical Society. Chemical communications, 1994, # 8, p. 973 - 974]

2
[ 683-16-9 ]
[ 70127-50-3 ]
[ 156422-13-8 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine In benzene for 1h; from RT to reflux;

Reference： [1]Bovin, Alexander N.; Yarkevich, Alla N.; Kharitonov, Alexander V.; Tsvetkov, Eugene N. [Journal of the Chemical Society. Chemical communications, 1994, # 8, p. 973 - 974]

3
[ 13482-64-9 ]
[ 70127-50-3 ]
[ 156422-16-1 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine In benzene for 1h; from RT to reflux;

Reference： [1]Bovin, Alexander N.; Yarkevich, Alla N.; Kharitonov, Alexander V.; Tsvetkov, Eugene N. [Journal of the Chemical Society. Chemical communications, 1994, # 8, p. 973 - 974]

4
[ 90-02-8 ]
[ 829-85-6 ]
[ 70127-50-3 ]

Yield	Reaction Conditions	Operation in experiment
86%	With hydrogenchloride 1) 15 min, 80-90 deg C, 2) 70 deg C;
68%	With hydrogenchloride; acetic acid for 13h; Heating;

Reference： [1]Evreinov,V. I.; Baulin, V. E.; Vostroknutova, Z. N.; Bondarenko, N. A.; Syundyukova, V. Kh.; Tsvetkov, E. N. [Bulletin of the Academy of Sciences of the USSR Division of Chemical Science, 1989, vol. 38, # 91, p. 1828 - 1834][Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1989, # 9, p. 1990 - 1997]
[2]Kron, T. E.; Sinyavskaya, E. I.; Tsvetkov, E. N. [Bulletin of the Academy of Sciences of the USSR Division of Chemical Science, 1986, vol. 35, # 11, p. 2241 - 2246][Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1986, # 11, p. 2451 - 2456]

5
[ 70127-50-3 ]
[ 55-86-7 ]
[ 209346-62-3 ]

Yield	Reaction Conditions	Operation in experiment
76%	With caesium carbonate In 1,4-dioxane for 14h; Heating;

Reference： [1]Solov'ev, Vitaly P.; Baulin, Vladimir E.; Strakhova, Nadezhda N.; Kazachenko, Vladimir P.; Belsky, Vitaly K.; Varnek, Alexandre A.; Volkova, Tatiana A.; Wipff, Georges [Journal of the Chemical Society. Perkin Transactions 2 (2001), 1998, # 6, p. 1489 - 1498]

6
[ 70127-50-3 ]
[ 817-09-4 ]
[ 177740-09-9 ]

Yield	Reaction Conditions	Operation in experiment
90%	With caesium carbonate In 1,4-dioxane for 14h; Heating;

7
2-methoxybenzyl diphenylphosphinite [ No CAS ]
[ 70127-50-3 ]
[ 159386-46-6 ]

Yield	Reaction Conditions	Operation in experiment
1: 77% 2: 9%	With trimethylsilyl bromide at 80℃; for 2h;

Reference： [1]Renard, Pierre-Yves; Vayron, Philippe; Mioskowski, Charles [Organic Letters, 2003, vol. 5, # 10, p. 1661 - 1664]

8
[ 89-95-2 ]
[ 829-85-6 ]
[ 70127-50-3 ]

Yield	Reaction Conditions	Operation in experiment
70%	With toluene-4-sulfonic acid In Dimethyl ether at 20℃; for 48h;

Reference： [1]Chikkali, Samir; Gudat, Dietrich [European Journal of Inorganic Chemistry, 2006, # 15, p. 3005 - 3009]

9
[ 70127-50-3 ]
[ 74-88-4 ]
C₂₀H₂₀O₂P⁽¹⁺⁾*I^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In tetrahydrofuran at 20℃; for 2h;

Reference： [1]Chikkali, Samir; Gudat, Dietrich [European Journal of Inorganic Chemistry, 2006, # 15, p. 3005 - 3009]

10
[ 70127-50-3 ]
2-[(diphenylphosphanyl)methyl]phenol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: tetrahydrofuran / 2 h / 20 °C 2: LiAlH₄ / tetrahydrofuran

Reference： [1]Chikkali, Samir; Gudat, Dietrich [European Journal of Inorganic Chemistry, 2006, # 15, p. 3005 - 3009]

11
[ 70127-50-3 ]
Diphenyl-phosphinic acid 2-(diethyl-phosphinoylmethyl)-phenyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: NEt₃ / benzene / 1 h / from RT to reflux 2: 75 percent / LiN(SiMe₃)2 / diethyl ether; tetrahydrofuran / -50 - 20 °C 3: 85 percent Spectr_. / pyridine / benzene / 2 h / 100 °C

Reference： [1]Bovin, Alexander N.; Yarkevich, Alla N.; Kharitonov, Alexander V.; Tsvetkov, Eugene N. [Journal of the Chemical Society. Chemical communications, 1994, # 8, p. 973 - 974]

12
[ 70127-50-3 ]
[ 156422-20-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: NEt₃ / benzene / 1 h / from RT to reflux 2: 75 percent / LiN(SiMe₃)2 / diethyl ether; tetrahydrofuran / -50 - 20 °C

Reference： [1]Bovin, Alexander N.; Yarkevich, Alla N.; Kharitonov, Alexander V.; Tsvetkov, Eugene N. [Journal of the Chemical Society. Chemical communications, 1994, # 8, p. 973 - 974]

13
[ 70127-50-3 ]
Diphenyl-phosphinic acid 2-(dipropyl-phosphinoylmethyl)-phenyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: NEt₃ / benzene / 1 h / from RT to reflux 2: 63 percent / LiN(SiMe₃)2 / diethyl ether; tetrahydrofuran / -50 - 20 °C 3: 84 percent Spectr_. / pyridine / benzene / 0.5 h / Heating

Reference： [1]Bovin, Alexander N.; Yarkevich, Alla N.; Kharitonov, Alexander V.; Tsvetkov, Eugene N. [Journal of the Chemical Society. Chemical communications, 1994, # 8, p. 973 - 974]

14
[ 70127-50-3 ]
2-[(Bis-chloromethyl-phosphinoyl)-(diphenyl-phosphinoyl)-methyl]-phenol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: NEt₃ / benzene / 1 h / from RT to reflux 2: 10 percent / LiN(SiMe₃)2 / diethyl ether; tetrahydrofuran / -50 - 20 °C

Reference： [1]Bovin, Alexander N.; Yarkevich, Alla N.; Kharitonov, Alexander V.; Tsvetkov, Eugene N. [Journal of the Chemical Society. Chemical communications, 1994, # 8, p. 973 - 974]

15
[ 70127-50-3 ]
[ 156422-21-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: NEt₃ / benzene / 1 h / from RT to reflux 2: 63 percent / LiN(SiMe₃)2 / diethyl ether; tetrahydrofuran / -50 - 20 °C

Reference： [1]Bovin, Alexander N.; Yarkevich, Alla N.; Kharitonov, Alexander V.; Tsvetkov, Eugene N. [Journal of the Chemical Society. Chemical communications, 1994, # 8, p. 973 - 974]

16
[ 70127-50-3 ]
2-[(Diphenyl-phosphinoyl)-(methyl-phenyl-phosphinoyl)-methyl]-phenol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: NEt₃ / benzene / 1 h / from RT to reflux 2: 75 percent / LiN(SiMe₃)2 / diethyl ether; tetrahydrofuran / -50 - 20 °C

Reference： [1]Bovin, Alexander N.; Yarkevich, Alla N.; Kharitonov, Alexander V.; Tsvetkov, Eugene N. [Journal of the Chemical Society. Chemical communications, 1994, # 8, p. 973 - 974]

17
[ 70127-50-3 ]
Diphenyl-phosphinic acid 2-(dibutyl-phosphinoylmethyl)-phenyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: NEt₃ / benzene / 1 h / from RT to reflux 2: 75 percent / LiN(SiMe₃)2 / diethyl ether; tetrahydrofuran / -50 - 20 °C 3: 90 percent Spectr_. / propan-2-ol / 10 h / 100 °C

Reference： [1]Bovin, Alexander N.; Yarkevich, Alla N.; Kharitonov, Alexander V.; Tsvetkov, Eugene N. [Journal of the Chemical Society. Chemical communications, 1994, # 8, p. 973 - 974]

18
[ 70127-50-3 ]
Diphenyl-phosphinic acid 2-(methyl-phenyl-phosphinoylmethyl)-phenyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: NEt₃ / benzene / 1 h / from RT to reflux 2: 75 percent / LiN(SiMe₃)2 / diethyl ether; tetrahydrofuran / -50 - 20 °C 3: 35 percent Spectr_. / pyridine / benzene / 1.5 h / Heating

Reference： [1]Bovin, Alexander N.; Yarkevich, Alla N.; Kharitonov, Alexander V.; Tsvetkov, Eugene N. [Journal of the Chemical Society. Chemical communications, 1994, # 8, p. 973 - 974]

19
[ 70127-50-3 ]
[ 156422-22-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: NEt₃ / benzene / 1 h / from RT to reflux 2: 75 percent / LiN(SiMe₃)2 / diethyl ether; tetrahydrofuran / -50 - 20 °C

Reference： [1]Bovin, Alexander N.; Yarkevich, Alla N.; Kharitonov, Alexander V.; Tsvetkov, Eugene N. [Journal of the Chemical Society. Chemical communications, 1994, # 8, p. 973 - 974]

20
[ 70127-50-3 ]
[ 156422-24-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: NEt₃ / benzene / 1 h / from RT to reflux 2: 25 percent / LiN(SiMe₃)2 / diethyl ether; tetrahydrofuran / -50 - 20 °C

Reference： [1]Bovin, Alexander N.; Yarkevich, Alla N.; Kharitonov, Alexander V.; Tsvetkov, Eugene N. [Journal of the Chemical Society. Chemical communications, 1994, # 8, p. 973 - 974]

21
[ 70127-50-3 ]
Diphenyl-phosphinic acid 2-(chloromethyl-phenyl-phosphinoylmethyl)-phenyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: NEt₃ / benzene / 1 h / from RT to reflux 2: 25 percent / LiN(SiMe₃)2 / diethyl ether; tetrahydrofuran / -50 - 20 °C 3: 15 percent Spectr_. / butan-2-one / 0.5 h / Heating

Reference： [1]Bovin, Alexander N.; Yarkevich, Alla N.; Kharitonov, Alexander V.; Tsvetkov, Eugene N. [Journal of the Chemical Society. Chemical communications, 1994, # 8, p. 973 - 974]

22
[ 70127-50-3 ]
[ 156422-19-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: NEt₃ / benzene / 1 h / from RT to reflux 2: 86 percent / LiN(SiMe₃)2 / diethyl ether; tetrahydrofuran / -50 - 20 °C

Reference： [1]Bovin, Alexander N.; Yarkevich, Alla N.; Kharitonov, Alexander V.; Tsvetkov, Eugene N. [Journal of the Chemical Society. Chemical communications, 1994, # 8, p. 973 - 974]

23
[ 70127-50-3 ]
[ 156422-32-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: NEt₃ / benzene / 1 h / from RT to reflux 2: 86 percent / LiN(SiMe₃)2 / diethyl ether; tetrahydrofuran / -50 - 20 °C 3: 96 percent / pyridine / 3 h / 20 °C

Reference： [1]Bovin, Alexander N.; Yarkevich, Alla N.; Kharitonov, Alexander V.; Tsvetkov, Eugene N. [Journal of the Chemical Society. Chemical communications, 1994, # 8, p. 973 - 974]

24
[ 70127-50-3 ]
2-[(Bis-phenoxymethyl-phosphinoyl)-(diphenyl-phosphinoyl)-methyl]-phenol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: NEt₃ / benzene / 1 h / from RT to reflux 2: 41 percent / LiN(SiMe₃)2 / diethyl ether; tetrahydrofuran / -50 - 20 °C

Reference： [1]Bovin, Alexander N.; Yarkevich, Alla N.; Kharitonov, Alexander V.; Tsvetkov, Eugene N. [Journal of the Chemical Society. Chemical communications, 1994, # 8, p. 973 - 974]

25
[ 719-80-2 ]
[ 90-01-7 ]
[ 70127-50-3 ]

Yield	Reaction Conditions	Operation in experiment
73%	In tetrahydrofuran	R.1 Synthesis of o-(diphenylphosphinylmethyl)phenol REFERENCE EXAMPLE 1 Synthesis of o-(diphenylphosphinylmethyl)phenol In a reactor equipped with a thermometer, a stirrer and a condenser were placed 99.2 g of o-(hydroxymethyl)phenol and 400 ml of tetrahydrofuran. They were made into a uniform solution. Thereto was added 184 g of ethyldiphenylphosphinite. The resulting mixture was subjected to reaction for 3 hr with heating and stirring. The reaction mixture was cooled and the resulting white crystal precipitate was separated by filtration and then dried to obtain 180 g of o-(diphenylphosphinylmethyl)phenol. Yield: 73% Melting point: 179° C.

Reference： [1]Current Patent Assignee: SUMITOMO CHEMICAL COMPANY LIMITED; Sumitomo Chemical (w/o Dongwoo Fine-Chem) - US4621123, 1986, A

26
2-[(diphenylphosphanyl)methyl]phenol [ No CAS ]
[ 70127-50-3 ]

Yield	Reaction Conditions	Operation in experiment
	With dihydrogen peroxide In water; acetonitrile at 20℃; for 0.166667h; Inert atmosphere;

Reference： [1]Wang, Feijun; Qu, Mingliang; Chen, Feng; Xu, Qin; Shi, Min [Chemical Communications, 2012, vol. 48, # 68, p. 8580 - 8582]

27
[ 108-86-1 ]
[ 14707-41-6 ]
[ 70127-50-3 ]

Yield	Reaction Conditions	Operation in experiment
53%	Stage #1: bromobenzene With magnesium In tetrahydrofuran Stage #2: 2-ethoxy-2,3-dihydro-[d][1,2]oxaphosphole 2-oxide In tetrahydrofuran for 2h; Reflux; Inert atmosphere; Stage #3: With sulfuric acid In tetrahydrofuran; water	Synthesis of dialkyl(diaryl)(2-hydroxybenzyl)phosphine oxides (general procedure) General procedure: Benzophosphole 1, 5 g (0.025 mol), was added dropwise to a Grignard reagent prepared by standard procedure from 0.063 mol of alkyl(aryl) bromide and 1.5 g (0.063 mol) of Mg in 30 mL of THF. The mixture was refluxed with stirring under argon for 2 h, let to cool to room temperature, and hydrolyzed with a solution of 0.063 mol of H2SO4 in 30 mL of water. The aqueous layer was extracted with CH2Cl2 (3 × 50 mL), the solvent was removed, and the residue was washed with diethyl ether

Reference： [1]Tatarinov; Kuznetsov; Kostin; Mironov [Russian Journal of General Chemistry, 2016, vol. 86, # 3, p. 530 - 533][Zh. Obshch. Khim., 2016, vol. 86, # 3, p. 386 - 390,5]

28
[ 54535-06-7 ]
[ 70127-50-3 ]
1,2-bis[2-((2-diphenyldiphenylphosphorylmethyl)phenoxy)ethoxy]benzene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
68%	Stage #1: diphenyl(2-hydroxyphenylmethyl)phosphine oxide With sodium hydroxide In 1,4-dioxane for 0.5h; Heating; Stage #2: bis(o-phenylene)glycol ditosylate In 1,4-dioxane for 10h; Heating;	1,2-Bis[2-((2-diphenylphosphorylmethyl)phenoxy)ethoxy]benzene (L2) was prepared analogously to L from a suspension of 2-diphenylphosphorylmethylphenol Ia (5.0 g, 16.2 mmol) in 40 mL of dry dioxane,finely ground sodium hydroxide (0.64 g, 16.4 mmol),and 1,2-bis[O,O'-di(2-oxyethyl)-1,2-benzene)]-4-methylbenzenesulfonate (4.11 g, 8.12 mmol). The residue obtained after evaporation of the chloroform extract was purified by column chromatography onsilica gel with CHCl3 and CHCl3-i-PrOH (10 : 1) as eluents. The yield was 4.30 g, 68%; mp = 73-75°(diethyl ether-acetone).For C48H44O6P2 anal. calcd. (%): C, 74.03; H, 5.69;P, 12.33.Found (%): C, 73.96 and 73.80; H, 5.59 and 5.61;P, 12.30 and 12.24.1H NMR (δ, ppm, CDCl3): 2.08 m (4,2P(O)H2Ar), 4.18 m (4, OCH2CH2), 4.42 m (4,OCH2CH2), 6.87 m (2, Ar-H), 7.15 m (2, Ar-H),7.38 m (2, Ar-H), 7.64 m (14, Ar-H), 7.96 m (8,Ar-H).31 NMR (δ, ppm, CDCl3): 31.60.

Reference： [1]Krivorot’ko; Polyakova; Ivanova; Pyatova; Baulin; Galkina; Dorokhov; Tsivadze, A. Yu. [Russian Journal of Inorganic Chemistry, 2016, vol. 61, # 10, p. 1241 - 1251][Zh. Neorg. Khim., 2016, vol. 61, # 10, p. 1298 - 1308,11]

29
[ 70127-50-3 ]
1,2-bis[O,O'-di(2-oxyethyl)-1,2-cyclohexanediol]-4-methylbenzenesulfonate [ No CAS ]
1,2-bis[2-((2-diphenylphosphorylmethyl)phenoxy)ethoxy]cyclohexane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
56%	Stage #1: diphenyl(2-hydroxyphenylmethyl)phosphine oxide With sodium hydroxide In 1,4-dioxane for 0.5h; Heating; Stage #2: 1,2-bis[O,O'-di(2-oxyethyl)-1,2-cyclohexanediol]-4-methylbenzenesulfonate In 1,4-dioxane for 10h; Heating;	1,2-Bis[2-((2-diphenylphosphorylmethyl)phenoxy)ethoxy]cyclohexane (L). Finely ground NaOH (0.62 g,15.4 mmol) was added to a suspension of 2-diphenylphosphorylmethylphenol Ia [6] (4.73 g, 15.4 mmol)in 35 mL of dioxane. The reaction mixture was heated to boiling and stirred for 0.5 h. 1,2-Bis[,'-di(2-oxyethyl)-1,2-cyclohexanediol)]-4-methylbenzenesulfonate[18] (3.83 g, 7.70 mmol) was then added to the mixture. The reaction mixture was boiled for 10 h and evaporated in a vacuum. The residue was treated with 100 mL of water, the solution was acidified to pH 1 with concentrated HCl, and the mixture was extracted with CHCl3 (3 × 40 mL). The extract was washed with water (3 × 40 mL) and evaporated in a vacuum. The residue was purified by column chromatography on silica gel with HCl3 and HCl3-i-PrOH (10 : 1) as eluents. The yield of L was 3.40 g, 56%; mp = 121-123° (diethyl ether-acetone).For C48H50O6P2 anal. calcd. (%): C, 73.45; H, 6.42;P, 7.89.Found (%): C, 73.24 and 73.43; H, 6.41 and 6.53;P, 8.05 and 8.10.1H NMR (δ, ppm, CDCl3): 1.34 m (4, 1,2-cyclohexyl),1.76 m (2, 1,2- cyclohexyl), 2.12 m (2, 1,2-cyclohexyl), 3.35 m (2, 1,2-cyclohexyl), 3.82 m(12, 222 + 22()), 6.72 d (2, 2JH-H =8.2 Hz, Ar-H), 7.20 t (2, 2, 3JH-H = 8.0 Hz, Ar-H),7.37 m (2, Ar-H), 7.55 m (12, Ar-H), 7.78 m (8,Ar-H).31 NMR (δ, ppm, CDCl3): 31.52.

30
[ 70127-50-3 ]
[ 112-26-5 ]
C₄₄H₄₄O₆P₂*NaI [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
77%		A suspension of4.5 g (14 mmol) of 2-diphenylphosphorylmethylphenol[12] and 0.56 g (14 mmol) of finely divided NaOHin 35 mL of dry dioxane was stirred for 0.5 h at 95C,next 1.3 g (7 mmol) of 1,8-dichloro-3,6-dioxaoctanewas added, the mixture was refluxed for 8 h, concentratedunder reduced pressure, 50 mL of water wasadded to the residue, the mixture was acidified withconcentrated HCl to pH 1 and extracted with CHCl3(3 × 25 mL). The extract was washed with diluted (1 : 2)HCl (2 × 30 mL), water (2 × 30 mL), and concentratedunder reduced pressure. The residue was dissolvedin 40 mL of anhydrous acetonitrile, 2.25 g (15 mmol) ofdry NaI was added, the mixture was refluxed for 1 h,cooled to 8C, the precipitate was separated by filtration,washed with boiling acetonitrile (10 mL) anddried in a vacuum. The precipitate was identified as a1 : 1 complex of L with NaI. Yield 4.3 g, 77%. ForC44H44INaO6P2 anal. calcd. (%): C, 60.01; H, 5.04; P,7.03. Found (%): C, 59.81, 59.73; H, 4.52, 4.90;P, 6.63, 6.91.

Reference： [1]Russian Journal of Inorganic Chemistry,2019,vol. 64,p. 1178 - 1185
Zh. Neorg. Khim.,2019,vol. 64,p. 997 - 1005,9

31
[ 70127-50-3 ]
[ 62-53-3 ]
2-[(diphenylphosphoryl)methyl]-4-(phenyldiazenyl)phenol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
48%	Stage #1: aniline With hydrogenchloride; sodium nitrite In water at 2 - 5℃; Stage #2: diphenyl(2-hydroxyphenylmethyl)phosphine oxide With sodium hydride In 1,4-dioxane; water; mineral oil at 0 - 20℃; for 2h;	2-(Diphenylphosphoryl)-4-(phenyldiazenyl)phenol (13) General procedure: Phenol 1, 3.60 g (12.4 mmol), was dispersed in 30 mL of anhydrous dioxane, 0.54 g (12.40 mmol) of a 55% suspension of sodium hydride in mineral oil was added, and the mixture was refluxed for 0.5 h. The mixture was cooled to 0°C and added to a solution of benzenediazonium salt prepared from 4.70 g (50.00 mmol) of aniline, 3.50 g (50.00 mmol) of sodium nitrite, and 20 mL of 35% aqueous HCl, maintaining the temperature at 2-5°C. The mixture was stirred for 2 h at room temperature, and the precipitate was filtered off, washed with dilute aqueous HCl (1 : 3, 3 * 30 mL), and dried. Yield 2.27 g (46%), mp 193-195°C (from EtOH).

Reference： [1]Rogacheva, Yu. I.; Baulin; Baulin; Tsivadze, A. Yu. [Russian Journal of General Chemistry, 2019, vol. 89, # 8, p. 1595 - 1603][Zh. Obshch. Khim., 2019, vol. 89, # 8, p. 1206 - 1215,10]

32
[ 70127-50-3 ]
2-[(diphenylphosphoryl)methyl]-4-nitrophenol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
58%	With nitric acid In acetonitrile at 60℃; for 0.5h;	2-(Diphenylphosphoryl)-4-nitrophenol (5) General procedure: Phenol 1, 1.00 g (3.40 mmol), was dissolved in 10 mL of acetonitrile, 0.23 mL of nitric acid (d = 1.5 g/mL) was added, and the mixture was stirred for 30 min at 60°C and poured onto ice. The precipitate was filtered off and purified by column chromatography using chloroform as eluent. Yield 0.58 g (50%), mp 243-245°C (from EtOH).

33
[ 70127-50-3 ]
2,4-dibromo-6-[(diphenylphosphoryl)methyl]phenol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
51%	With bromine; iron In tetrachloromethane at 25 - 50℃; for 5h;	4-Bromo-2-(diphenylphosphoryl)phenol (9) General procedure: Bromine, 1.20 g (6.80 mmol), was added to a suspension of 2.00 g (6.80 mmol) of 2-(diphenylphosphoryl)phenol (1) and 0.10 g (0.18 mmol) of iron powder in 15 mL of anhydrous carbon tetrachloride. The mixture was stirred for 3 h at 50°C and for 2 h at 25°C, poured into 100 mL of water, and extracted with chloroform (3 * 30 mL). The extract was dried over Na2SO4, and the solvent was removed under reduced pressure. The residue was treated with 25 mL of diethyl ether, and the precipitate was filtered off and dried. Yield 1.06 g (42%), mp 218-220°C (from benzene).

34
[ 70127-50-3 ]
4-bromo-2-[(diphenylphosphoryl)methyl]phenol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
44%	With bromine; iron In tetrachloromethane at 25 - 50℃; for 5h;	4-Bromo-2-(diphenylphosphoryl)phenol (9) General procedure: Bromine, 1.20 g (6.80 mmol), was added to a suspension of 2.00 g (6.80 mmol) of 2-(diphenylphosphoryl)phenol (1) and 0.10 g (0.18 mmol) of iron powder in 15 mL of anhydrous carbon tetrachloride. The mixture was stirred for 3 h at 50°C and for 2 h at 25°C, poured into 100 mL of water, and extracted with chloroform (3 * 30 mL). The extract was dried over Na2SO4, and the solvent was removed under reduced pressure. The residue was treated with 25 mL of diethyl ether, and the precipitate was filtered off and dried. Yield 1.06 g (42%), mp 218-220°C (from benzene).

35
[ 70127-50-3 ]
[ 33730-69-7 ]
(2-((diphenylphosphoryl)methoxy)benzyl)diphenylphosphine oxide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
77%	With caesium carbonate In 1,4-dioxane at 100℃; for 8h;	(2-((diphenylphosphoryl)methoxy)benzyl)diphenylphosphineoxide (VI) A mixture of 3.22 g (10.00mmol) 2-(hydroxybenzyl)diphenylphosphine oxide 3.86 g(10.00 mmol) (diphenylphosphoryl)methyl-4-methylbenzenesulphonate and 2.26 g (10.00 mmol) anhydrous cesium carbonate in 35 mL of dry dioxane was heated and stirred at 100 ° for 8 h. 36 The reaction mixture was diluted by 75 mL of water, acidified by adding concentrated HCl to pH 1, and extracted by CHCl3 (3 × 25 mL). The organic layer was separated, washed with water, and evaporated under reduced pressure to give crude product VI. It was purified by column chromatography on silica gel 100-160 mm, the eluents CHCl3 and CHCl3/i-PrOH (10:1 ).The yield of VI was 4.04 g (77 %), m.p. 168-169.5 °. Anal.Calcd. for C32H28O3P2 (%): C, 73.56; H, 5.40; P 11.86.Found (%): C, 73.40; H, 5.34; P, 11.69. 1H NMR (CDCl3):δ: 3. 81 (2H, d, 2JH-P = 7.10 Hz, ArCH2P), 4.49 (2, d,2JH-P = 5.18 Hz, 2(O), 7.00-7.32 (2, m, Ar-H),7.35-7.56 (12, m, Ar-H), 7.61-7.92 (10, m, Ar-H). 31PNMR (CDCl3): δ: 28.15, 32.15.

Reference： [1]Baulin, Dmitriy Vladimirovich; Baulin, Vladimir Evgenevich; Karandashev, Vasilii Konstantinovich; Tsivadze, Aslan Yusupovich; Turanov, Alexander Nikolaevich [Acta Chimica Slovenica, 2020, vol. 67, # 1, p. 246 - 252]

36
[ 14707-41-6 ]
[ 70127-50-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: sodium bromide / dichloromethane / 2 h / 20 °C / Inert atmosphere 2: water / Inert atmosphere 3: thionyl chloride / neat (no solvent) / 10 h / Inert atmosphere; Reflux 4: thionyl chloride / neat (no solvent) / 10 h / Inert atmosphere; Reflux 5: magnesium / benzene; tetrahydrofuran / 0.5 h / Inert atmosphere

Reference： [1]Lyubina, Anna P.; Mironov, Vladimir F.; Pashirova, Tatiana N.; Sapunova, Anastasiia S.; Shaihutdinova, Zukhra M.; Tatarinov, Dmitry A.; Terekhova, Natalia V.; Voloshina, Alexandra D.; Zakharova, Lucia Ya. [Bioorganic and medicinal chemistry letters, 2020, vol. 30, # 13]

37
[ 108-86-1 ]
2-chloro-3H-benzo[d][1,2]oxaphosphole-2-oxide [ No CAS ]
[ 70127-50-3 ]

Yield	Reaction Conditions	Operation in experiment
95%	Stage #1: bromobenzene; 2-chloro-3H-benzo[d][1,2]oxaphosphole-2-oxide With magnesium In tetrahydrofuran; benzene for 0.5h; Inert atmosphere; Stage #2: With sulfuric acid; water	(2-Hydroxybenzyl)diphenylphosphine oxide 2⁵ A solution of 2-chloro-3H-benzo[d][1,2]oxaphosphole 2-oxide 3 (1 g, 5.3 mmol) in 2 mL of benzene was added dropwise to a Grignard reagent prepared by standard procedure from bromobenzene (1.4 mL, 2.1 g, 13.3 mmol) and magnesium turnings (0.32 g, 13.3 mmol) in 5 mL of THF. The mixture was stirred under argon for 30 min and then hydrolyzed with a solution of H2SO4 (1.3 g, 0.71 mL, 13.3 mmol) in 5 mL of water. The aqueous layer was extracted with CH2Cl2 (3 × 10 mL), the solvent was removed, and the residue was washed with diethyl ether to give (2-hydroxybenzyl)diphenylphosphine oxide as a white powder. Yield 1.55 g (95 %).

38
[ 17045-27-1 ]
[ 70127-50-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: thionyl chloride / neat (no solvent) / 10 h / Inert atmosphere; Reflux 2: thionyl chloride / neat (no solvent) / 10 h / Inert atmosphere; Reflux 3: magnesium / benzene; tetrahydrofuran / 0.5 h / Inert atmosphere

39
C₇H₇O₃P [ No CAS ]
[ 70127-50-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: thionyl chloride / neat (no solvent) / 10 h / Inert atmosphere; Reflux 2: magnesium / benzene; tetrahydrofuran / 0.5 h / Inert atmosphere

40
C₁₀H₁₇O₄PSi [ No CAS ]
[ 70127-50-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: water / Inert atmosphere 2: thionyl chloride / neat (no solvent) / 10 h / Inert atmosphere; Reflux 3: thionyl chloride / neat (no solvent) / 10 h / Inert atmosphere; Reflux 4: magnesium / benzene; tetrahydrofuran / 0.5 h / Inert atmosphere

41
[ 70127-50-3 ]
2,2-diphenyl-2,3-dihydrobenzo[d][1,2]oxaphosphol-2-ium chloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With thionyl chloride In dichloromethane for 0.25h; Inert atmosphere;	2.3 General procedure for synthesis of phosphonium salts 6.⁶ (2-Hydroxybenzyl)diphenylphosphine oxide (150 mg, 0.48 mmol) dissolved in 2 mL of CH2Cl2 was treated with Thionyl chloride SOCl2 0.05 mL (85.7 mg, 0.7 mmol) and stirred for 15 min. Then all volatiles were removed in vacuum. The crude product was dissolved in 2 mL of THF and the Grignard reagent prepared of appropriate alkyl bromide (0.7 mmol) and magnesium turnings (24 mg, 1 mmol) in 1 mL of THF was added to the suspension of quasiphosphonium salt 5 while cooling with water bath. The mixture was stirred for 1 hour then hydrolyzed with a solution of hydrochloric acid (NH4Cl for unsaturated derivatives) and extracted with CH2Cl2 (3×10 mL). The organic layer was dried over Na2SO4. The products were purified by a silica gel flash-chromatography (ethyl acetate for impurities and ethanol for salts). After evaporation corresponding salts 6 were obtained as solids. 2,2-Diphenyl-2,3-dihydrobenzo[d][1,2]oxaphosphol-2-ium chloride (5 1916ClOP). Dark-brown oily liquid, yield 0.138 g (99%); 1H NMR (CDCl3, 400 MHz) δ: 8.03 (dd, 4H, J = 14.8 Hz, J = 7.6 Hz, H9); 7.65 (br.td, 2H, J = 7.1 Hz, J = 1.6 Hz, H11); 7.54 (td, 4H, J = 7.6 Hz, J = 4.6 Hz, H10); 7.42 (d, 1H, J = 7.6 Hz, H4); 7.23 (t, 1H, J = 7.9 Hz, H6); 7.06 (t, 1H, J = 7.5 Hz, H5); 7.00 (d, 1H, J = 8.2 Hz, H7; 4.91 (d, 2H, JPH = 13.6 Hz, H3) ppm. 13C NMR (CDCl3, 100.6 MHz) δ: 154.8 (d, JPC = 5.0 Hz, C7a), 134.5 (d, JPC = 3.0 Hz, C11), 132.2 (d, JPC = 12.3 Hz, C9), 129.9 (s, C6), 129.2 (d, JPC = 15.0 Hz, C10), 126.8 (d, JPC = 17.4 Hz, C4), 124.6 (d, JPC = 116.9 Hz, C8), 124.2 (s, C5), 120.5 (d, JPC = 3.0 Hz, C3a), 113.3 (d, JPC = 8.4 Hz, C7), 35.0 (d, JPC = 71.2 Hz, C3) ppm. 31P{1H} NMR (CDCl3, 202.4 MHz) δ: 78 ppm.

42
[ 70127-50-3 ]
(2-hydroxybenzyl)(octadecyl)diphenylphosphonium chloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: thionyl chloride / dichloromethane / 0.25 h / Inert atmosphere 2.1: magnesium / tetrahydrofuran / Inert atmosphere 2.2: Inert atmosphere

43
[ 70127-50-3 ]
(Z)-(2-hydroxybenzyl)(octadec-9-en-1-yl)diphenylphosphonium chloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: thionyl chloride / dichloromethane / 0.25 h / Inert atmosphere 2.1: magnesium / tetrahydrofuran / Inert atmosphere 2.2: Inert atmosphere

44
[ 70127-50-3 ]
hex-5-en-1-yl(2-hydroxybenzyl)diphenylphosphonium chloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: thionyl chloride / dichloromethane / 0.25 h / Inert atmosphere 2.1: magnesium / tetrahydrofuran / Inert atmosphere 2.2: Inert atmosphere

45
[ 70127-50-3 ]
[ 19259-70-2 ]
hexyl(2-hydroxybenzyl)diphenylphosphonium chloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: thionyl chloride / dichloromethane / 0.25 h / Inert atmosphere 2.1: magnesium / tetrahydrofuran / Inert atmosphere 2.2: Inert atmosphere

46
[ 70127-50-3 ]
heptyl(2-hydroxybenzyl)diphenylphosphonium chloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: thionyl chloride / dichloromethane / 0.25 h / Inert atmosphere 2.1: magnesium / tetrahydrofuran / Inert atmosphere 2.2: Inert atmosphere

47
[ 70127-50-3 ]
decyl(2-hydroxybenzyl)diphenylphosphonium chloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: thionyl chloride / dichloromethane / 0.25 h / Inert atmosphere 2.1: magnesium / tetrahydrofuran / Inert atmosphere 2.2: Inert atmosphere

48
[ 70127-50-3 ]
dodecyl(2-hydroxybenzyl)diphenylphosphonium chloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: thionyl chloride / dichloromethane / 0.25 h / Inert atmosphere 2.1: magnesium / tetrahydrofuran / Inert atmosphere 2.2: Inert atmosphere

49
[ 70127-50-3 ]
(2-hydroxybenzyl)diphenyl(tetradecyl)phosphonium chloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: thionyl chloride / dichloromethane / 0.25 h / Inert atmosphere 2.1: magnesium / tetrahydrofuran / Inert atmosphere 2.2: Inert atmosphere

50
[ 70127-50-3 ]
hexadecyl(2-hydroxybenzyl)diphenylphosphonium chloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: thionyl chloride / dichloromethane / 0.25 h / Inert atmosphere 2.1: magnesium / tetrahydrofuran / Inert atmosphere 2.2: Inert atmosphere

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H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
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H204	Fire or projection hazard
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H221	Flammable gas
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H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
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H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
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H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
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H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
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Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

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[ 70127-50-3 ] Synthesis Path-Downstream 1~50

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