[ CAS No. 1638-86-4 ]

Name: 1638-86-4|Diethyl phenylphosphonite|98% GC
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Product Details of [ 1638-86-4 ]

CAS No. :	1638-86-4	MDL No. :	MFCD00009086
Formula :	C₁₀H₁₅O₂P	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	RVDJLKVICMLVJQ-UHFFFAOYSA-N
M.W :	198.20 g/mol	Pubchem ID :	74225
Synonyms :

Safety of [ 1638-86-4 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P301+P312-P302+P352-P304+P340-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 1638-86-4 ]

* 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 [ 1638-86-4 ]

[ 1638-86-4 ] Synthesis Path-Downstream 1~59

1
[ 506-68-3 ]
[ 1638-86-4 ]
[ 120232-75-9 ]

Yield	Reaction Conditions	Operation in experiment
89%	In diethyl ether for 1h; Ambient temperature;

Reference： [1]Neidlein, R.; Buseck, S. [Monatshefte fur Chemie, 1993, vol. 124, # 3, p. 309 - 318] Buseck; Neidlein [Archiv der Pharmazie, 1993, vol. 326, # 4, p. 193 - 197]
[2]Current Patent Assignee: BAYER AG - DE938187, 1952, C

2
[ 1638-86-4 ]
[ 172487-18-2 ]

Yield	Reaction Conditions	Operation in experiment
80%	With silica gel In benzene
	With water
10.8 g	With hydrogenchloride; water In tetrahydrofuran at 20℃; for 0.333333h; Inert atmosphere;

Reference： [1]Abdulganeeva, S. A.; Erzhanov, K. B.; Sadykov, T. S. [Journal of general chemistry of the USSR, 1986, vol. 56, p. 1100 - 1104][Zhurnal Obshchei Khimii, 1986, vol. 56, # 6, p. 1249 - 1254]
[2]Koehler; Michaelis [Chemische Berichte, 1877, vol. 10, p. 811,815]
[3]Location in patent: experimental part Volle, Jean-Noel; Filippini, Damien; Midrier, Camille; Sobecki, Michal; Drag, Marcin; Virieux, David; Pirat, Jean-Luc [Synthesis, 2011, # 15, p. 2490 - 2494]

3
[ 64-17-5 ]
[ 644-97-3 ]
[ 1638-86-4 ]

Yield	Reaction Conditions	Operation in experiment
95.5%	With <i>N</i>,<i>N</i>-dimethyl-aniline In pentane for 0.5h; Ambient temperature;
87.5%	at 0 - 45℃; for 2.5h; Alkaline conditions; Sealed tube;	2.2 (2) Synthesis of diethyl phenylphosphonate In the electric liquid seal stirring device, constant pressure dropping funnel,In a 250-ml four-necked flask with a thermometer and a bulb-type condenser tube (upper section equipped with a drying tube), 0.4 mol of absolute ethanol and 10 ml of basic ionic liquid were added. Add 0.1 mol of phenylphosphonium dichloride to the constant pressure dropping funnel with stirring, use the ice water bath and adjust the dropping speed of phenylphosphine dichloride, The reaction temperature was controlled at about 0C, and after completion of the dropwise addition, the mixture was stirred at about 45C for 2.5 hours. After the reaction is completed, the reaction solution is poured into a beaker, cooled and filtered to obtain a solid crude product of diethyl phenylphosphonate. The product was recrystallized from a mixture of petroleum ether and dichloromethane to obtain a pure product with a yield of 87.5%.
86%	With pyridine In diethyl ether for 1h; Ambient temperature;

75%	With amine
71%	Stage #1: Dichlorophenylphosphine With pyridine In hexane Inert atmosphere; Cooling with ice; Stage #2: ethanol In hexane at 0 - 26℃; for 17h; Inert atmosphere;
65%	at 20 - 25℃;
58%	With N,N-diethylaniline In diethyl ether at 5 - 20℃;
	With <i>N</i>,<i>N</i>-dimethyl-aniline
	With <i>N</i>,<i>N</i>-dimethyl-aniline In diethyl ether Ambient temperature;
	With sodium ethanolate
	With pyridine
	With pyridine In hexane for 3h; Ambient temperature;
70 g	In toluene
	With triethylamine
	With pyridine In Petroleum ether
	In diethyl ether at -20℃; for 2h; Inert atmosphere;
	With pyridine In tetrahydrofuran at 20℃; for 12h; Inert atmosphere;

Reference： [1]Boetzel, Ruth; Haegele, Gerhard [Journal of Fluorine Chemistry, 1994, vol. 68, # 1, p. 11 - 14]
[2]Current Patent Assignee: CHANGZHOU VOCATIONAL INSTITUTE OF ENGINEERING - CN107501322, 2017, A Location in patent: Paragraph 0042; 0044; 0045; 0062
[3]Germanaud, Laurent; Brunel, Sylvian; Chevalier, Yves; Le Perchec, Pierre [Bulletin de la Societe Chimique de France, 1988, # 4, p. 699 - 704]
[4]Blazewska, Katarzyna M. [Journal of Organic Chemistry, 2014, vol. 79, # 1, p. 408 - 412]
[5]Bagi, Péter; Fogassy, Elemér; Herbay, Réka; Holczbauer, Tamás; Keglevich, György; Mátravölgyi, Béla; Madarász, János; Székely, György; Varga, Bence [European Journal of Organic Chemistry, 2020]
[6]Location in patent: experimental part Krutikova; Krutikov; Erkin [Russian Journal of General Chemistry, 2010, vol. 80, # 3, p. 428 - 433]
[7]Kaźmierczak, Aleksandra; Kusy, Damian; Niinivehmas, Sanna P.; Gmach, Joanna; Joachimiak, Łukasz; Pentikäinen, Olli T.; Gendaszewska-Darmach, Edyta; Błazewska, Katarzyna M. [Journal of Medicinal Chemistry, 2017, vol. 60, # 21, p. 8781 - 8800]
[8]Kamai [Zhurnal Obshchei Khimii, 1948, vol. 18, p. 443,445,446][Chem.Abstr., 1948, p. 7723]
[9]Coskran,K.J. et al. [Journal of the American Chemical Society, 1968, vol. 90, p. 5437 - 5442]
[10]Green,M.; Hudson,R.F. [Journal of the Chemical Society, 1963, p. 540 - 547]
[11]Siddall,T.H.; Prohaska,C.A. [Journal of the American Chemical Society, 1962, vol. 84, p. 3467 - 3473] Chernyshev,E.A. et al. [Doklady Chemistry, 1962, vol. 147, p. 967 - 968][Doklady Akademii Nauk SSSR, 1962, vol. 147, p. 117 - 118]
[12]Collins, David J.; Drygala, Peter F.; Swan, John M. [Australian Journal of Chemistry, 1983, vol. 36, # 10, p. 2095 - 2110]
[13]Wieczorek, J. S.; Boduszek, B.; Wielkopolski, W. A.; Gancarz, R.; Jaskulska, E. [Journal fur praktische Chemie (Leipzig 1954), 1987, vol. 329, # 1, p. 165 - 170]
[14]Morise, Xavier; Savignac, Philippe; Denis, Jean-Marc [Journal of the Chemical Society. Perkin transactions I, 1996, # 17, p. 2179 - 2185]
[15]Chaudhry, Amirah; Hargcr, Martin J. P.; Shuff, Philippa; Thompson, Alison [Journal of the Chemical Society. Perkin transactions I, 1999, # 10, p. 1347 - 1352]
[16]Zhang, Dapeng; Lian, Mingming; Liu, Jia; Tang, Shukun; Liu, Guangzhi; Ma, Cunfei; Meng, Qingwei; Peng, Haisheng; Zhu, Daling [Organic Letters, 2019, vol. 21, # 8, p. 2597 - 2601]
[17]Xu, Shipan; Xie, Jun; Liu, Yu; Xu, Weifeng; Tang, Ke-Wen; Xiong, Biquan; Wong, Wai-Yeung [Journal of Organic Chemistry, 2021, vol. 86, # 21, p. 14983 - 15003]

4
[ 13508-53-7 ]
[ 1638-86-4 ]
[ 839-43-0 ]

Reference： [1]Doklady Chemistry,1962,vol. 147,p. 967 - 968
Doklady Akademii Nauk SSSR,1962,vol. 147,p. 117 - 118

5
[ 1638-86-4 ]
[ 75-03-6 ]
[ 2227-43-2 ]

Yield	Reaction Conditions	Operation in experiment
91%	at 26 - 80℃; for 21.5h; Inert atmosphere;
	In benzene at 85℃; for 60h;

Reference： [1]Bagi, Péter; Fogassy, Elemér; Herbay, Réka; Holczbauer, Tamás; Keglevich, György; Mátravölgyi, Béla; Madarász, János; Székely, György; Varga, Bence [European Journal of Organic Chemistry, 2020]
[2]Green,M.; Hudson,R.F. [Journal of the Chemical Society, 1963, p. 540 - 547]
[3]Pikul, Stanislaw; McDow Dunham, Kelly L.; Almstead, Neil G.; De, Biswanath; Natchus, Michael G.; Anastasio, Melanie V.; McPhail, Sara J.; Snider, Catherine E.; Taiwo, Yetunde O.; Chen, Longyin; Dunaway, C. Michelle; Gu, Fei; Mieling, Glen E. [Journal of Medicinal Chemistry, 1999, vol. 42, # 1, p. 87 - 94]

6
[ 3167-63-3 ]
[ 1638-86-4 ]
[ 81073-28-1 ]

Reference： [1]Journal of Medicinal Chemistry,1992,vol. 35,p. 4885 - 4892

7
[ 10586-45-5 ]
[ 1638-86-4 ]
[ 91270-79-0 ]

Yield	Reaction Conditions	Operation in experiment
81%	With nickel dibromide In water at 160 - 180℃;

Reference： [1]Horner, Leopold; Flemming, Hans-Wolfram [Phosphorus and Sulfur and the Related Elements, 1984, vol. 19, p. 345 - 362]

8
[ 1638-86-4 ]
[ 74924-95-1 ]
[ 91270-82-5 ]

Yield	Reaction Conditions	Operation in experiment
67%	With nickel dibromide In water at 160 - 180℃;
57%	With nickel dibromide at 175℃; for 2h;

Reference： [1]Horner, Leopold; Flemming, Hans-Wolfram [Phosphorus and Sulfur and the Related Elements, 1984, vol. 19, p. 345 - 362]
[2]Horner, Leopold; Lindel, Hans [Chemische Berichte, 1985, vol. 118, # 2, p. 676 - 682]

9
[ 1638-86-4 ]
[ 39181-18-5 ]

Yield	Reaction Conditions	Operation in experiment
91%	With selenium In benzene for 24h; Ambient temperature;
51.6%	With selenium at 140℃; for 2h;

Reference： [1]Bhardwaj, Raj K.; Davidson, R. Stephen [Tetrahedron, 1987, vol. 43, # 19, p. 4473 - 4480]
[2]Bayandina, E. V.; Sadkova, D. N.; Osankina, E. I.; Nuretdinov, I. A. [Journal of general chemistry of the USSR, 1989, vol. 59, # 91, p. 1792 - 1795][Zhurnal Obshchei Khimii, 1989, vol. 59, # 9, p. 1999 - 2003]

10
[ 1638-86-4 ]
[ 762-42-5 ]
[ 113345-30-5 ]

Yield	Reaction Conditions	Operation in experiment
92%	In toluene at -50℃; 30 min at -50 deg C, then room temperature;
	In toluene at -70℃; for 0.5h; to room t.;

Reference： [1]Caesar, Julian C.; Griffiths, D. Vaughan; Tebby, John C. [Phosphorus and Sulfur and the Related Elements, 1987, vol. 29, p. 123 - 128]
[2]Caesar, Julian C.; Griffiths, D. Vaughan; Tebby, John C. [Journal of the Chemical Society. Perkin transactions I, 1988, p. 175 - 178]

11
[ 1638-86-4 ]
[ 71-43-2 ]
[ 1733-55-7 ]

Reference： [1]Phosphorus and Sulfur and the Related Elements,1980,vol. 8,p. 55 - 58

12
[ 1638-86-4 ]
[ 18171-19-2 ]
[3-(Dimethoxy-methyl-silanyl)-propyl]-phenyl-phosphinic acid ethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Yield given;

Reference： [1]Skvortsov, N. K.; Voloshina, N. F.; Moldavskaya, N. A.; Reikhsfel'd, V. O. [Journal of general chemistry of the USSR, 1988, vol. 58, # 8, p. 1634 - 1642][Zhurnal Obshchei Khimii, 1988, vol. 58, # 8, p. 1831 - 1840]

13
[ 51333-90-5 ]
[ 1638-86-4 ]
[2-(2-Oxo-pyrrolidin-1-yl)-ethyl]-phenyl-phosphinic acid ethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
56%

Reference： [1]Gurevich, P. A.; Klimentova, G. Yu.; Moskva, V. V.; Zykova, T. V.; Shagvaleev, F. Sh.; Kiselev, V. V. [Journal of general chemistry of the USSR, 1987, vol. 57, p. 2071 - 2074][Zhurnal Obshchei Khimii, 1987, vol. 57, # 10, p. 2316 - 2319]

14
[ 75-11-6 ]
[ 1638-86-4 ]
[ 2129-78-4 ]

Yield	Reaction Conditions	Operation in experiment
92%	at 110℃; for 14h; Inert atmosphere; Schlenk technique;
	at 140 - 170℃;

Reference： [1]Lutter, Michael; Jurkschat, Klaus [European Journal of Inorganic Chemistry, 2018, vol. 2018, # 30, p. 3481 - 3490]
[2]Henning,H.-G. [Journal fur praktische Chemie (Leipzig 1954), 1965, vol. 29, p. 93 - 100]

15
[ 1638-86-4 ]
[ 2227-43-2 ]

Yield	Reaction Conditions	Operation in experiment
78%	With ethyl iodide at 95℃; for 48h;
68%	With trimethylsilyl trifluoromethanesulfonate In chloroform at 60℃; for 72h;
42%	With trimethylsilyl bromide at 80℃; for 120h;

With diiodomethane at 140 - 170℃;

Reference： [1]Nowlan, Charity; Li, Yingchun; Hermann, Johannes C.; Evans, Timothy; Carpenter, Joseph; Ghanem, Eman; Shoichet, Brian K.; Raushel, Frank M. [Journal of the American Chemical Society, 2006, vol. 128, # 49, p. 15892 - 15902]
[2]Renard, Pierre-Yves; Vayron, Philippe; Leclerc, Eric; Valleix, Alain; Mioskowski, Charles [Angewandte Chemie - International Edition, 2003, vol. 42, # 21, p. 2389 - 2392]
[3]Renard, Pierre-Yves; Vayron, Philippe; Mioskowski, Charles [Organic Letters, 2003, vol. 5, # 10, p. 1661 - 1664]
[4]Henning,H.-G. [Journal fur praktische Chemie (Leipzig 1954), 1965, vol. 29, p. 93 - 100]

16
[ 1638-86-4 ]
[ 39069-02-8 ]
dimethyl 1,10-phenanthroline-2,9-diyldimethylenebis(phenylphosphinate) [ No CAS ]

Reference： [1]Journal of the Chemical Society, Dalton Transactions,1996,p. 2693 - 2698

17
[ 67-56-1 ]
[ 1638-86-4 ]
[ 366-18-7 ]
[ 1754-49-0 ]
[ 61733-60-6 ]
[ 2240-41-7 ]

Reference： [1]Chemische Berichte,1997,vol. 130,p. 1699 - 1707

18
[ 1638-86-4 ]
[ 1754-49-0 ]

Yield	Reaction Conditions	Operation in experiment
60%	With pyridine; water; iodine In tetrahydrofuran at -45 - 20℃; for 0.333333h;
	With tris(1,10-phenanthroline)iron(III) tris(hexafluorophosphate); ethanol In acetonitrile at 25℃;
	With rhodamine 6G In water; acetonitrile at 25℃; Irradiation;

	With p-nitrostilbene dibromide In methanol; acetonitrile at 25℃;
	Multi-step reaction with 2 steps 1: 71 percent / cumene / standard deoxygenation route 2: 21 percent Spectr_. / 0.17 h / 600 °C / 0 - 0.01 Torr / other time (80 min)
	Multi-step reaction with 2 steps 1: 91 percent / selenium / benzene / 24 h / Ambient temperature 2: 64 percent / di-n-hexyl sulphide / CHCl₃; methanol / 1 h / Irradiation; other reagents
	With 3,6-bis(ethylamino)-9-[2-(methoxycarbonyl)phenyl]-xanthylium chloride In water; acetonitrile Irradiation;

Reference： [1]Blazewska, Katarzyna M. [Journal of Organic Chemistry, 2014, vol. 79, # 1, p. 408 - 412]
[2]Yasui, Shinro; Itoh, Kenji; Tsujimoto, Munekazu; Ohno, Atsuyoshi [Chemistry Letters, 1998, # 10, p. 1019 - 1020]
[3]Yasui, Shinro; Tsujimoto, Munekazu; Itoh, Kenji; Ohno, Atsuyoshi [Journal of Organic Chemistry, 2000, vol. 65, # 15, p. 4715 - 4720]
[4]Yasui, Shinro [Heteroatom Chemistry, 2001, vol. 12, # 4, p. 217 - 222]
[5]Cadogan, J. I. G.; Husband, James B.; McNab, Hamish [Journal of the Chemical Society. Perkin transactions I, 1983, # 7, p. 1489 - 1495]
[6]Bhardwaj, Raj K.; Davidson, R. Stephen [Tetrahedron, 1987, vol. 43, # 19, p. 4473 - 4480]
[7]Yasui, Shinro; Tsujimoto, Munekazu [Journal of Physical Organic Chemistry, 2013, vol. 26, # 12, p. 1090 - 1097]

19
[ 75-61-6 ]
[ 1638-86-4 ]
Ethyl (1-bromo-1,1-difluoromethyl)-phenylphosphinate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
99%	at 20℃; for 2h;
58%	In diethyl ether at 20℃; Inert atmosphere;	4.5.3. Preparation of ethyl bromodifluoromethylphenylphosphinate 16 Diethyl phenylphosphonite (11.6 g, 0.059 mol) and diethyl ether (125 ml) were combined in a 250 ml round bottom flask equipped with a water condensor topped by a glass tee leading to a source of dry nitrogen and a mineral oil bubbler. After cooling the flask in an ice bath, 1 (15 g, 0.07 mol) was added. The reaction mixture was stirred overnight at ambient temperature. The ether was removed by rotary evaporation at aspirator pressure and the residue distilled to give 16 in 58% yield (bp = 109-111 °C/ 0.6 mm Hg). 19F NMR (CDCl3) (ppm): ABX pattern δ (F1) = -62.5; δ (F2) = -62.1 (2JPF1 = 2JPF2 = 82 Hz; 2JF1F2 = 180 Hz); (31P NMR (CDCl3) (ppm): δ = 20.9 (t, 2JPF = 82 Hz); 13C NMR (CDCl3) (ppm): δ = 120.2 (td, 1JCF = 333 Hz, 1JCP = 150 Hz), d = 64. (2JCP = 7.4 Hz), d = 16.5 (3JCP = 5.9 Hz) and for the ring carbons, d = 123.5 (d, 1JCP = 146 Hz, a-carbon of ring), d = 128.9 (d, 1JCP = 13.2 Hz, m-ring carbons), d = 133.4 (d, 1JCP = 10.3 Hz, o-ring carbons), d = 134 (d, 1JCP = 2.9 Hz, p-ring carbon); 1H NMR (CDCl3) (ppm): δ = 1.45 (t, 3JHH = 7 Hz), d = 4.45 (qd, 3JHH = 7 Hz, 3JHP = 7.5 Hz), d = 7.5-8.0 (unresolved multiplet). GC-MS, m/z (relative intensity): 169 (57), 141 (100), 77 (64), 51 (34), 47 (15), 31 (22), 29 (34); no molecular ion observed: IR (P=O) 1252 cm-1: Anal. Calcd. for C8H10O2PCF2Br: C, 36.12%; H, 3.34%. Found C, 36.13%; H, 3.25%.

Reference： [1]Vayron, Philippe; Renard, Pierre-Yves; Valleix, Alain; Mioskowski, Charles [Chemistry - A European Journal, 2000, vol. 6, # 6, p. 1050 - 1063]
[2]Location in patent: experimental part Flynn, Richard M.; Burton, Donald J. [Journal of Fluorine Chemistry, 2011, vol. 132, # 10, p. 815 - 828]

20
[ 1638-86-4 ]
[ 272789-47-6 ]
[ 272789-48-7 ]

Yield	Reaction Conditions	Operation in experiment
99%	In toluene for 18h; Heating;

Reference： [1]Vayron, Philippe; Renard, Pierre-Yves; Valleix, Alain; Mioskowski, Charles [Chemistry - A European Journal, 2000, vol. 6, # 6, p. 1050 - 1063]

21
[ 1638-86-4 ]
[ 284025-85-0 ]
C₇₆H₈₄N₄O₁₈P₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
58%	In tetrahydrofuran at 70℃; for 48h;

Reference： [1]Arduini, Arturo; Boehmer, Volker; Delmau, Laetitia; Desreux, Jean-Francois; Dozol, Jean-Francois; Garcia Carrera, M. Alejandro; Lambert, Bernard; Musigmann, Christian; Pochini, Andrea; Shivanyuk, Alexander; Ugozzoli, Franco [Chemistry - A European Journal, 2000, vol. 6, # 12, p. 2135 - 2144]

22
[ 36309-68-9 ]
[ 1638-86-4 ]
Te-p-methoxyphenyl O-ethyl phenylphosphonotellurate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87%	With triethylamine In dichloromethane at 20℃; for 0.333333h;

Reference： [1]Hayashi, Minoru; Miura, Toshiyuki; Matsuchika, Keiji; Watanabe, Yutaka [Synthesis, 2004, # 9, p. 1481 - 1485]

23
[ 1638-86-4 ]
[ 80078-56-4 ]
(+/-)-(2R_P,3R)-5,7-di-tert-butyl-3-(4-methoxyphenyl)-2-phenylbenzo[d]-1,2-oxaphosphole 2-oxide [ No CAS ]
(+/-)-(2R_P,3S)-5,7-di-tert-butyl-3-(4-methoxyphenyl)-2-phenylbenzo[d]-1,2-oxaphosphole 2-oxide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1: 48% 2: 37%	Stage #1: <3,5-bis(1,1,-dimethylethyl)-2-hydroxyphenyl>(4-methoxyphenyl)methanol With hydrogen bromide; phosphorus tribromide In toluene at -30 - 20℃; for 0.5h; Stage #2: diethyl phenylphosphonite In toluene at 25℃; for 6h; Stage #3: With sodium hydroxide In toluene

Reference： [1]Perez-Prieto, Julia; Galian, Raquel E.; Miranda, Miguel Angel; Catalina, Fernando; Martin-Vargas, Nuria; Lopez-Ortiz, Fernando [Organic Letters, 2004, vol. 6, # 4, p. 561 - 564]

24
[ 1638-86-4 ]
[ 70484-01-4 ]
[ 724425-61-0 ]

Reference： [1]Helvetica Chimica Acta,2004,vol. 87,p. 825 - 844

25
[ 1198-51-2 ]
[ 1638-86-4 ]
[ 862094-28-8 ]

Reference： [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 1727 - 1730

26
[ 1638-86-4 ]
(R)-4-acetylphenyl ethyl(phenyl)phosphinate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: 78 percent / ethyl iodide / 48 h / 95 °C 2: oxalyl chloride / 0.67 h / 20 °C 3: triethylamine / diethyl ether / 24 h / 20 °C 4: bacterial phosphotriesterase G₆₀A mutant / various solvent(s) / pH 9.0
	Multi-step reaction with 4 steps 1: 78 percent / ethyl iodide / 48 h / 95 °C 2: oxalyl chloride / 0.67 h / 20 °C 3: triethylamine / diethyl ether / 24 h / 20 °C 4: bacterial phosphotriesterase I₁₀₆G, F₁₃₂G, S₃₀₈A mutant / various solvent(s) / pH 9.0

Reference： [1]Nowlan, Charity; Li, Yingchun; Hermann, Johannes C.; Evans, Timothy; Carpenter, Joseph; Ghanem, Eman; Shoichet, Brian K.; Raushel, Frank M. [Journal of the American Chemical Society, 2006, vol. 128, # 49, p. 15892 - 15902]
[2]Nowlan, Charity; Li, Yingchun; Hermann, Johannes C.; Evans, Timothy; Carpenter, Joseph; Ghanem, Eman; Shoichet, Brian K.; Raushel, Frank M. [Journal of the American Chemical Society, 2006, vol. 128, # 49, p. 15892 - 15902]

27
[ 1638-86-4 ]
(S)-4-acetylphenyl ethyl(phenyl)phosphinate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: 78 percent / ethyl iodide / 48 h / 95 °C 2: oxalyl chloride / 0.67 h / 20 °C 3: triethylamine / diethyl ether / 24 h / 20 °C 4: bacterial phosphotriesterase I₁₀₆G, F₁₃₂G, S₃₀₈A mutant / various solvent(s) / pH 9.0

28
[ 1638-86-4 ]
[ 918660-73-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 78 percent / ethyl iodide / 48 h / 95 °C 2: oxalyl chloride / 0.67 h / 20 °C 3: triethylamine / diethyl ether / 24 h / 20 °C

29
[ 1638-86-4 ]
[ 13317-44-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: 78 percent / ethyl iodide / 48 h / 95 °C 2: oxalyl chloride / 0.67 h / 20 °C 3: triethylamine / diethyl ether / 24 h / 20 °C 4: bacterial phosphotriesterase G₆₀A mutant / various solvent(s) / pH 9.0
	Multi-step reaction with 4 steps 1: 78 percent / ethyl iodide / 48 h / 95 °C 2: oxalyl chloride / 0.67 h / 20 °C 3: triethylamine / diethyl ether / 24 h / 20 °C 4: bacterial phosphotriesterase I₁₀₆G, F₁₃₂G, S₃₀₈A mutant / various solvent(s) / pH 9.0

Reference： [1]Nowlan, Charity; Li, Yingchun; Hermann, Johannes C.; Evans, Timothy; Carpenter, Joseph; Ghanem, Eman; Shoichet, Brian K.; Raushel, Frank M. [Journal of the American Chemical Society, 2006, vol. 128, # 49, p. 15892 - 15902]
[2]Nowlan, Charity; Li, Yingchun; Hermann, Johannes C.; Evans, Timothy; Carpenter, Joseph; Ghanem, Eman; Shoichet, Brian K.; Raushel, Frank M. [Journal of the American Chemical Society, 2006, vol. 128, # 49, p. 15892 - 15902]

30
[ 1638-86-4 ]
[ 1499-22-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 78 percent / ethyl iodide / 48 h / 95 °C 2: oxalyl chloride / 0.67 h / 20 °C
	Multi-step reaction with 2 steps 1: benzene / 60 h / 85 °C 2: oxalyl chloride / benzene / 3 h / Ambient temperature
	Multi-step reaction with 2 steps 2: COCl₂

Reference： [1]Nowlan, Charity; Li, Yingchun; Hermann, Johannes C.; Evans, Timothy; Carpenter, Joseph; Ghanem, Eman; Shoichet, Brian K.; Raushel, Frank M. [Journal of the American Chemical Society, 2006, vol. 128, # 49, p. 15892 - 15902]
[2]Pikul, Stanislaw; McDow Dunham, Kelly L.; Almstead, Neil G.; De, Biswanath; Natchus, Michael G.; Anastasio, Melanie V.; McPhail, Sara J.; Snider, Catherine E.; Taiwo, Yetunde O.; Chen, Longyin; Dunaway, C. Michelle; Gu, Fei; Mieling, Glen E. [Journal of Medicinal Chemistry, 1999, vol. 42, # 1, p. 87 - 94]
[3]Green,M.; Hudson,R.F. [Journal of the Chemical Society, 1963, p. 540 - 547]

31
[ 1638-86-4 ]
[ 93383-27-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 25 °C 2: Fe, NH₄Cl / H₂O / Heating

Reference： [1]Kyba, Evan P.; Clubb, Clyde N.; Larson, Steven B.; Schueler, Victor J.; Davis, E. Raymond [Journal of the American Chemical Society, 1985, vol. 107, p. 2141 - 2148]

32
[ 1638-86-4 ]
[ 94890-96-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: 25 °C 2: Fe, NH₄Cl / H₂O / Heating 4: 76 percent

Reference： [1]Kyba, Evan P.; Clubb, Clyde N.; Larson, Steven B.; Schueler, Victor J.; Davis, E. Raymond [Journal of the American Chemical Society, 1985, vol. 107, p. 2141 - 2148]

33
[ 1638-86-4 ]
[ 93383-23-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 25 °C 2: Fe, NH₄Cl / H₂O / Heating

Reference： [1]Kyba, Evan P.; Clubb, Clyde N.; Larson, Steven B.; Schueler, Victor J.; Davis, E. Raymond [Journal of the American Chemical Society, 1985, vol. 107, p. 2141 - 2148]

34
[ 1638-86-4 ]
[ 94890-97-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: 25 °C 2: Fe, NH₄Cl / H₂O / Heating 4: 76 percent 5: 96 percent / 2.64 M n-butyllithium / hexane; tetrahydrofuran / -78 °C

Reference： [1]Kyba, Evan P.; Clubb, Clyde N.; Larson, Steven B.; Schueler, Victor J.; Davis, E. Raymond [Journal of the American Chemical Society, 1985, vol. 107, p. 2141 - 2148]

35
[ 1638-86-4 ]
[ 94890-94-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: 25 °C 2: Fe, NH₄Cl / H₂O / Heating 4: 1.80 M n-butyllithium / hexane; tetrahydrofuran / -78 °C

Reference： [1]Kyba, Evan P.; Clubb, Clyde N.; Larson, Steven B.; Schueler, Victor J.; Davis, E. Raymond [Journal of the American Chemical Society, 1985, vol. 107, p. 2141 - 2148]

36
[ 1638-86-4 ]
[ 94890-92-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: 25 °C 2: Fe, NH₄Cl / H₂O / Heating 4: 60.5 percent / 2.80 M n-butyllithium / diethyl ether / from -78 deg C to r.t.

Reference： [1]Kyba, Evan P.; Clubb, Clyde N.; Larson, Steven B.; Schueler, Victor J.; Davis, E. Raymond [Journal of the American Chemical Society, 1985, vol. 107, p. 2141 - 2148]

37
[ 1638-86-4 ]
[ 94904-40-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 7 steps 1: 25 °C 2: Fe, NH₄Cl / H₂O / Heating 4: 76 percent 5: 96 percent / 2.64 M n-butyllithium / hexane; tetrahydrofuran / -78 °C 6: potassium hydroxide / tetrahydrofuran; aq. ethanol / 106 h / Ambient temperature 7: sodium butylthiolate / dimethylformamide / 9 h / 80 °C
	Multi-step reaction with 5 steps 1: 25 °C 2: Fe, NH₄Cl / H₂O / Heating 4: potassium hydroxide / tetrahydrofuran; aq. ethanol / 106 h / Ambient temperature 5: sodium butylthiolate / dimethylformamide / 9 h / 80 °C

Reference： [1]Kyba, Evan P.; Clubb, Clyde N.; Larson, Steven B.; Schueler, Victor J.; Davis, E. Raymond [Journal of the American Chemical Society, 1985, vol. 107, p. 2141 - 2148]
[2]Kyba, Evan P.; Clubb, Clyde N.; Larson, Steven B.; Schueler, Victor J.; Davis, E. Raymond [Journal of the American Chemical Society, 1985, vol. 107, p. 2141 - 2148]

38
[ 1638-86-4 ]
[ 94890-93-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: 25 °C 2: Fe, NH₄Cl / H₂O / Heating 4: 92 percent / potassium hydroxide / methanol; tetrahydrofuran / 1 h / -78 °C

Reference： [1]Kyba, Evan P.; Clubb, Clyde N.; Larson, Steven B.; Schueler, Victor J.; Davis, E. Raymond [Journal of the American Chemical Society, 1985, vol. 107, p. 2141 - 2148]

39
[ 1638-86-4 ]
[ 94890-98-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1: 25 °C 2: Fe, NH₄Cl / H₂O / Heating 4: 76 percent 5: 96 percent / 2.64 M n-butyllithium / hexane; tetrahydrofuran / -78 °C 6: potassium hydroxide / tetrahydrofuran; aq. ethanol / 106 h / Ambient temperature
	Multi-step reaction with 4 steps 1: 25 °C 2: Fe, NH₄Cl / H₂O / Heating 4: potassium hydroxide / tetrahydrofuran; aq. ethanol / 106 h / Ambient temperature

40
[ 1638-86-4 ]
[ 94890-99-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 8 steps 1: 25 °C 2: Fe, NH₄Cl / H₂O / Heating 4: 76 percent 5: 96 percent / 2.64 M n-butyllithium / hexane; tetrahydrofuran / -78 °C 6: potassium hydroxide / tetrahydrofuran; aq. ethanol / 106 h / Ambient temperature 7: sodium butylthiolate / dimethylformamide / 9 h / 80 °C 8: potassium hydroxide, / tetrahydrofuran; aq. ethanol / -78 °C
	Multi-step reaction with 6 steps 1: 25 °C 2: Fe, NH₄Cl / H₂O / Heating 4: potassium hydroxide / tetrahydrofuran; aq. ethanol / 106 h / Ambient temperature 5: sodium butylthiolate / dimethylformamide / 9 h / 80 °C 6: potassium hydroxide, / tetrahydrofuran; aq. ethanol / -78 °C

41
[ 1638-86-4 ]
[ 94890-89-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 8 steps 1: 25 °C 2: Fe, NH₄Cl / H₂O / Heating 4: 76 percent 5: 96 percent / 2.64 M n-butyllithium / hexane; tetrahydrofuran / -78 °C 6: potassium hydroxide / tetrahydrofuran; aq. ethanol / 106 h / Ambient temperature 7: sodium butylthiolate / dimethylformamide / 9 h / 80 °C 8: 1.) potassium hydroxide; 2.) lithium diisopropylamide / 1.) THF, aq. EtOH, -78 deg C; 2.) THF, 0 deg C, hexane
	Multi-step reaction with 6 steps 1: 25 °C 2: Fe, NH₄Cl / H₂O / Heating 4: potassium hydroxide / tetrahydrofuran; aq. ethanol / 106 h / Ambient temperature 5: sodium butylthiolate / dimethylformamide / 9 h / 80 °C 6: 1.) potassium hydroxide; 2.) lithium diisopropylamide / 1.) THF, aq. EtOH, -78 deg C; 2.) THF, 0 deg C, hexane

42
[ 1638-86-4 ]
[ 94890-88-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: 25 °C 2: Fe, NH₄Cl / H₂O / Heating 4: 60.5 percent / 2.80 M n-butyllithium / diethyl ether / from -78 deg C to r.t. 5: 3.7 percent / KH / tetrahydrofuran

Reference： [1]Kyba, Evan P.; Clubb, Clyde N.; Larson, Steven B.; Schueler, Victor J.; Davis, E. Raymond [Journal of the American Chemical Society, 1985, vol. 107, p. 2141 - 2148]

43
[ 1638-86-4 ]
[ 94890-88-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: 25 °C 2: Fe, NH₄Cl / H₂O / Heating 4: 60.5 percent / 2.80 M n-butyllithium / diethyl ether / from -78 deg C to r.t. 5: 33.6 percent / KH / tetrahydrofuran

Reference： [1]Kyba, Evan P.; Clubb, Clyde N.; Larson, Steven B.; Schueler, Victor J.; Davis, E. Raymond [Journal of the American Chemical Society, 1985, vol. 107, p. 2141 - 2148]

44
[ 1638-86-4 ]
[ 94942-82-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: 25 °C 2: Fe, NH₄Cl / H₂O / Heating 4: 1.80 M n-butyllithium / hexane; tetrahydrofuran / -78 °C 5: 22 percent / 1.80 M n-butyllithium / hexane; tetrahydrofuran / -78 °C

Reference： [1]Kyba, Evan P.; Clubb, Clyde N.; Larson, Steven B.; Schueler, Victor J.; Davis, E. Raymond [Journal of the American Chemical Society, 1985, vol. 107, p. 2141 - 2148]

45
[ 1638-86-4 ]
[ 94890-91-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: 25 °C 2: Fe, NH₄Cl / H₂O / Heating 4: 1.80 M n-butyllithium / hexane; tetrahydrofuran / -78 °C 5: 5 percent / 1.80 M n-butyllithium / hexane; tetrahydrofuran / -78 °C

Reference： [1]Kyba, Evan P.; Clubb, Clyde N.; Larson, Steven B.; Schueler, Victor J.; Davis, E. Raymond [Journal of the American Chemical Society, 1985, vol. 107, p. 2141 - 2148]

46
[ 1638-86-4 ]
[ 1089-77-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 2: concentrated aqueous HCl

Reference： [1]Mastalerz [Roczniki Chemii, 1959, vol. 33, p. 985,989][Chem.Abstr., 1960, p. 6602]

47
[ 106-38-7 ]
[ 1638-86-4 ]
[ 4294-57-9 ]
[ 29865-23-4 ]

Yield	Reaction Conditions	Operation in experiment
	With sulfuric acid; sodium hydrogencarbonate	6 p-Tolylphenylphosphine oxide EXAMPLE 6 p-Tolylphenylphosphine oxide A solution of p-tolylmagnesium bromide [prepared from p-bromotoluene (29.1 g, 0.16 mol) and magnesium (4.38 g, 0.18 g-atom)] in ether (100 mL) was treated with a solution of ethyl phenylphosphonite (13,6 g, 0.08 mol) in ether (50 mL) with vigorous mechanical stirring. The mixture was heated at reflux for 1/2 hr., then 100 mL of 25% sulfuric acid was added cautiously. Three layers formed; the bottom (aqueous) layer was extracted with toluene. Addition of NaHCO3 to the combined upper layers produced a vigorous reaction and a single organic phase. The organic phase was washed with water and with saturated NaCl, dried and evaporated to give an oil (14 g). Kugelrohr distillation at 120°-160° C. (0.1 mmHg) followed by chromatography on silica gel (CHCl3), then 10% MeOH--CHCl3) gave 7.1 g of an oil. This was distilled in the Kugelrohr again (150° C., 0.1 mmHg) to give 6.2 g of product which appears to be pure by NMR and crystallized on standing. 1 H NMR (CDCl3) δ8.0-7.2 (m, 9H), 8.08 (d, J=480 Hz, 1H), 2.42 (s, 3H).

Reference： [1]Current Patent Assignee: HONEYWELL INTERNATIONAL INC - US4574060, 1986, A

48
[ 1638-86-4 ]
ethyl(oxo-oxetan-4-ylmethyl)phenylphoshinate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With dibenzoyl peroxide	24 EXAMPLE 24 EXAMPLE 24 A mixture of 8.4 parts of diketene, 2.5 parts of benzoyl peroxide and 20.0 parts of ethyl phenylphosponite were added dropwise over 1 hr to 48.1 parts of vigorously stirred ethyl phenylphosphonite which was heated at 120° C. in an atmosphere of nitrogen. The excess phosphonite was removed by passing the reaction mixture down a wiped wall still at 80° C. at a pressure of 0.013 mb. The residue was distilled on a wiped wall still at a temperature of 110° C. and a pressure of 0.013 mb and the product, ethyl(2-oxo-4-oxetanylmethyl)phenylphosphinate, was obtained as a colourless oil which was shown by 31 P NMR to be a nearly equal mixture of diastereoisomers having chemical shifts at δ-37.5 and δ-37.7 and which had the following elemental analysis by weight. Calculated for C12 H15 O4 P C, 56.69; H, 5.95; P, 12.18: Found C, 56.15; H, 6.25; P, 12.06.

Reference： [1]Current Patent Assignee: NOVARTIS AG; Novartis (w/o Sandoz) - US4384966, 1983, A

49
[ 1638-86-4 ]
[ 75-03-6 ]
[ 1499-22-5 ]
[ 2227-43-2 ]

Yield	Reaction Conditions	Operation in experiment
	In benzene	9 EXAMPLE 9 EXAMPLE 9 Ethyl ethylphenylphosphinate: A mixture of diethyl phenyl phosphonite (4.5g, 22.70mmol), ethyl iodide (0.24mL, 3mmol) and benzene (100mL) is stirred and heated at 85°C for 24 hours. The reaction is 30% complete as indicated by tlc. Another portion of ethyl iodide (0.30mL, 3.75mmol) is added and the reaction is stirred for additional 36 hours at 85°C when it appears complete by tic. The volatiles are removed on a rotary evaporater to give ethyl ethylphenylphosphinate as an oil. Ethylphenylphosphinic chloride:

Reference： [1]Current Patent Assignee: PROCTER & GAMBLE CO - EP925303, 2002, B1

50
[ 16971-33-8 ]
[ 1638-86-4 ]
[ 86494-67-9 ]

Yield	Reaction Conditions	Operation in experiment
61%	With NaB(C₆H₅)4 In ethanol; benzene Ru(II) complex and a ligand in a mixt. of EtOH-C6H6 heating under reflux for 2 h under N2, soln. filtering, treating with NaB(C6H5)4 in EtOH, concg., standing overnight, ppt. filtering off, washing with EtOH and light petroleum, drying in vacuo; puirified by recrystallisation from CH2Cl2-EtOH; identified by elem. anal., IR and NMR spectra;

Reference： [1]Creswell, Clifford J.; Robinson, Stephen D.; Sahajpal, Arvind [Polyhedron, 1983, vol. 2, p. 517 - 522]

51
chloro(1,5-cyclooctadiene)iridium(I) dimer [ No CAS ]
[ 1638-86-4 ]
[ 144497-19-8 ]

Yield	Reaction Conditions	Operation in experiment
78%	With carbon monoxide In hexane (N2), soln. of the P-compd. added dropwise to a suspn. of the Ir-complex in hexane over 1 h, treated with a stream of CO for 40 min; filtered, concd. in vacuo, cooled to -78°C, pptn. filtered off, washed 3 times with cold heptane, dried in vacuo, elem. anal.;

Reference： [1]Luo, Xiao-Liang; Michos, Demetrius; Crabtree, Robert H.; Hall, Michael B. [Inorganica Chimica Acta, 1992, vol. 198 - 200, p. 429 - 436]

52
{Ir(C₈H₁₂)I}2 [ No CAS ]
[ 1638-86-4 ]
[ 144497-24-5 ]

Yield	Reaction Conditions	Operation in experiment
66%	With carbon monoxide In hexane (N2), soln. of the P-compd. added dropwise to a suspn. of the Ir-complexin hexane over 1 h, treated with a stream of CO for 40 min; evapd. in vacuo, cooled to -78°C, filtered off, washed 3 times with cold heptane, dried in vacuo, elem. anal.;

Reference： [1]Luo, Xiao-Liang; Michos, Demetrius; Crabtree, Robert H.; Hall, Michael B. [Inorganica Chimica Acta, 1992, vol. 198 - 200, p. 429 - 436]

53
[ 227751-39-5 ]
[ 1638-86-4 ]
[ 227751-41-9 ]

Yield	Reaction Conditions	Operation in experiment
90%	In dichloromethane byproducts: PhCN; 3 equiv. of phosphite, stirring for 5 h at room temp.; evapn., trituration (EtOH), collection (filtration), crystn. (CH2Cl2:EtOH); elem. anal.;

Reference： [1]Albertin, Gabriele; Antoniutti, Stefano; Bordignon, Emilio; Carlon, Michela [Organometallics, 1999, vol. 18, # 11, p. 2052 - 2054]

54
[ 15746-57-3 ]
[ 1638-86-4 ]
Δ-(R)/Λ-(S)-[Ru(bipyridine)2(PhP(OH)(OEt))(Cl)]Cl [ No CAS ]
Δ-(S)/Λ-(R)-[Ru(bipyridine)2(PhP(OH)(OEt))(Cl)]Cl [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With water In ethanol EtOH/H2O (85::15 v/v), 70°C, 20 h; chromy. in the dark;

Reference： [1]Hesek; Hembury; Drew; Taniguchi; Inoue [Journal of the American Chemical Society, 2000, vol. 122, # 41, p. 10236 - 10237]

55
[ 15746-57-3 ]
[ 1638-86-4 ]
cis-Δ/Λ-[Ru(bipyridine)2(PhP(OEt)2)(Cl)]Cl [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
96%	In ethanol EtOH (abs.), 70°C, 3 h; chromy. in the dark;

Reference： [1]Hesek; Hembury; Drew; Taniguchi; Inoue [Journal of the American Chemical Society, 2000, vol. 122, # 41, p. 10236 - 10237]

56
[ 17857-24-8 ]
[ 1638-86-4 ]
[ 214973-78-1 ]

Yield	Reaction Conditions	Operation in experiment
85%	In not given inert atmosphere; 5 h (according to Brunet et al., Inorg. Synth. 1992, 29, 156); extn. with petroleum ether:C6H6=4:1, crystn. (to give oil);

Reference： [1]Albertin, Gabriele; Antoniutti, Stefano; Bacchi, Alessia; Barbera, Davide; Bordignon, Emilio; Pelizzi, Giancarlo; Ugo, Paolo [Inorganic Chemistry, 1998, vol. 37, # 21, p. 5602 - 5610]

57
[ 105063-69-2 ]
[ 1638-86-4 ]
[ 143-66-8 ]
[ 710279-85-9 ]

Yield	Reaction Conditions	Operation in experiment
75%	With Zn In ethanol under Ar; PPh(OEt)2 (excess) added to suspn. of Os complex and Zn dust (excess) in EtOH; refluxed; filtered; filtrate evapd. to dryness; oil triturated with EtOH contg. NaBPh4 (excess); elem. anal.;

Reference： [1]Albertin, Gabriele; Antoniutti, Stefano; Pizzol, Sonia [Journal of Organometallic Chemistry, 2004, vol. 689, # 9, p. 1639 - 1647]

58
4-dimethylaminocarbonyl-3-methyl-1-aminocarbonyl-1,2-diaza-1,3-butadiene [ No CAS ]
[ 1638-86-4 ]
[ 1045710-67-5 ]

Yield	Reaction Conditions	Operation in experiment
88%	Stage #1: 4-dimethylaminocarbonyl-3-methyl-1-aminocarbonyl-1,2-diaza-1,3-butadiene; diethyl phenylphosphonite at 20℃; for 0.5h; Stage #2: In tetrahydrofuran at 20℃; for 1h; Further stages.;

Reference： [1]Attanasi, Orazio A.; Baccolini, Graziano; Boga, Carla; De Crescentini, Lucia; Filippone, Paolino; Mantellini, Fabio [Tetrahedron, 2008, vol. 64, # 28, p. 6724 - 6732]

59
[ 1006033-77-7 ]
[ 1638-86-4 ]
[ 1045710-69-7 ]

Yield	Reaction Conditions	Operation in experiment
93%	Stage #1: methyl 3-[(aminocarbonyl)diazenyl]pent-2-enoate; diethyl phenylphosphonite at 20℃; for 0.5h; Stage #2: In tetrahydrofuran at 20℃; for 2h; Further stages.;

Reference： [1]Attanasi, Orazio A.; Baccolini, Graziano; Boga, Carla; De Crescentini, Lucia; Filippone, Paolino; Mantellini, Fabio [Tetrahedron, 2008, vol. 64, # 28, p. 6724 - 6732]

Related Products

Historical Records

Ghs Precautionary Statements

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

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
{[ item.p_purity ]}	{[ item.pr_size ]}	{[ getRatePrice(item.pr_usd, 1,1) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]}	{[ getRatePrice(item.pr_usd, 1,1) ]}	{[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} {[ getRatePrice(item.pr_usd,1,item.mem_rate) ]}	{[ item.pr_usastock ]}	Inquiry -	{[ item.pr_chinastock ]}	Inquiry -

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

[ CAS No. 1638-86-4 ]

Quality Control of [ 1638-86-4 ]

Related Doc. of [ 1638-86-4 ]

Product Details of [ 1638-86-4 ]

Safety of [ 1638-86-4 ]

Application In Synthesis of [ 1638-86-4 ]

[ 1638-86-4 ] Synthesis Path-Downstream 1~59

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry