Name: 28322-40-9|Isopentyltriphenylphosphonium bromide|98%
Brand: Ambeed
SKU: A232989
Price: 11.0 USD
Availability: InStock
Rating: 90 (30 reviews)

1
[ 603-35-0 ]
[ 107-82-4 ]
[ 28322-40-9 ]

Yield	Reaction Conditions	Operation in experiment
96.6%	for 18h; Heating;
81%	In acetonitrile for 120h; Heating;
81%	In acetonitrile for 120h; Heating;

81%	In toluene for 120h; Heating;
32%	In toluene at 100℃; for 24h;
	In N,N-dimethyl-formamide Heating;
	In benzene
	In xylene Heating;
	In acetonitrile Heating;
	at 100℃; for 24h;
	In neat (no solvent) at 100℃; for 15h;
	In acetonitrile Reflux;
300 g	In toluene at 90℃; for 10h; Inert atmosphere;	1-2 At room temperature, put 190g of triphenylphosphine into the reaction flask,120g of bromoisopentane, 200ml of toluene,Stir for 10min, replace with nitrogen,Warm up to 90°C for reaction, monitored by TLC,The reaction is completed in about 10 hours, filtered, and the solid is rinsed with toluene.The filter cake was dried at 50°C to obtain 300 g of isoamyltriphenylphosphonium bromide.

Reference： [1]Buss, Antony D.; Warren, Stuart [Journal of the Chemical Society. Perkin transactions I, 1985, p. 2307 - 2326]
[2]Shioiri, Takayuki; Terao, Yoshihiro; Irako, Naoko; Aoyama, Toyohiko [Tetrahedron, 1998, vol. 54, # 51, p. 15701 - 15710]
[3]Shioiri, Takayuki; Irako, Naoko [Tetrahedron, 2000, vol. 56, # 46, p. 9129 - 9142]
[4]Bergstroem, Moa Andresen; Luthman, Kristina; Nilsson, J. Lars G.; Karlberg, Ann-Therese [Chemical Research in Toxicology, 2006, vol. 19, # 6, p. 760 - 769]
[5]Werner, Markus; Stephenson, David S.; Szeimies, Guenter [Liebigs Annalen, 1996, # 11, p. 1705 - 1715]
[6]Hutchins,R.F.N. et al. [Steroids, 1970, vol. 15, p. 113 - 130] Inhoffen et al. [Chemische Berichte, 1959, vol. 92, p. 1772,1785]
[7]Zell [Helvetica Chimica Acta, 1979, vol. 62, # 2, p. 474 - 480]
[8]Davis,J.B. et al. [Journal of the Chemical Society C: Organic, 1966, p. 2154 - 2165]
[9]Mori,K. et al. [Tetrahedron, 1979, vol. 35, p. 833 - 837]
[10]Irako, Naoko; Shioiri, Takayuki [Tetrahedron Letters, 1998, vol. 39, # 32, p. 5793 - 5796]
[11]Mai, Enzo; Schneider, Christoph [Chemistry - A European Journal, 2007, vol. 13, # 9, p. 2729 - 2741]
[12]Noguchi, Taro; Oishi, Shinya; Honda, Kaori; Kondoh, Yasumitsu; Saito, Tamio; Ohno, Hiroaki; Osada, Hiroyuki; Fujii, Nobutaka [Chemical Communications, 2016, vol. 52, # 49, p. 7653 - 7656]
[13]Current Patent Assignee: ALBERTA RES CHEMICALS - WO2020/82162, 2020, A1 Location in patent: Paragraph 0050
[14]Current Patent Assignee: HUNAN KEREY PHARMACEUTICAL - CN112358523, 2021, A Location in patent: Paragraph 0107-0108; 0110-0111

2
[ 28322-40-9 ]
[ 46941-66-6 ]

Yield	Reaction Conditions	Operation in experiment
77.6%	With sodium hydroxide In water Heating;

Reference： [1]Buss, Antony D.; Warren, Stuart [Journal of the Chemical Society. Perkin transactions I, 1985, p. 2307 - 2326]

3
[ 28322-40-9 ]
[ 39110-24-2 ]

Yield	Reaction Conditions	Operation in experiment
	With n-butyllithium In hexane; toluene Yield given;
	With n-butyllithium In hexane; toluene at 25℃; for 1h;

Reference： [1]Furst; Labler; Meier [Helvetica Chimica Acta, 1982, vol. 65, # 5, p. 1499 - 1521]
[2]Shea, Regan G.; Fitzner, Jeffrey N.; Fankhauser, John E.; Spaltenstein, Andreas; Carpino, Philip A.; et al. [Journal of Organic Chemistry, 1986, vol. 51, # 26, p. 5243 - 5252]

4
[ 28322-40-9 ]
[ 93495-41-1 ]

Yield	Reaction Conditions	Operation in experiment
87%	With hydrogen In ethanol

Reference： [1]Kryshtal', G. V.; Zhdankina, G. M.; Serebryakov, E. P. [Russian Chemical Bulletin, 1993, vol. 42, # 12, p. 2039 - 2042][Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1993, # 12, p. 2126 - 2129]

5
[ 28322-40-9 ]
[ 165960-95-2 ]
[ 212838-91-0 ]

Yield	Reaction Conditions	Operation in experiment
85%	With n-butyllithium for 1h; Ambient temperature;
85%	With n-butyllithium In tetrahydrofuran at 20℃; for 1h;
	With n-butyllithium In tetrahydrofuran at 20℃; for 1h;

Reference： [1]Irako, Naoko; Shioiri, Takayuki [Tetrahedron Letters, 1998, vol. 39, # 32, p. 5793 - 5796]
[2]Shioiri, Takayuki; Irako, Naoko [Tetrahedron, 2000, vol. 56, # 46, p. 9129 - 9142]
[3]Current Patent Assignee: ALBERTA RES CHEMICALS - WO2020/82162, 2020, A1 Location in patent: Paragraph 0050

6
[ 28322-40-9 ]
[ 165960-95-2 ]
14-benzyloxy-2-methyl-4-tetradecene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With n-butyllithium In tetrahydrofuran; hexane at -10 - 20℃; for 1h;

Reference： [1]Shioiri, Takayuki; Terao, Yoshihiro; Irako, Naoko; Aoyama, Toyohiko [Tetrahedron, 1998, vol. 54, # 51, p. 15701 - 15710]

7
[ 28322-40-9 ]
[ 106673-33-0 ]
[ 326794-23-4 ]

Yield	Reaction Conditions	Operation in experiment
92%	With n-butyllithium In tetrahydrofuran at 20℃; for 1h;

Reference： [1]Shioiri, Takayuki; Irako, Naoko [Tetrahedron, 2000, vol. 56, # 46, p. 9129 - 9142]

8
[ 28322-40-9 ]
[ 131118-61-1 ]
[ 331822-45-8 ]

Yield	Reaction Conditions	Operation in experiment
54%	Stage #1: isoamyltriphenylphosphonium bromide With sodium hexamethyldisilazane In tetrahydrofuran for 1h; Heating; Stage #2: 3'-tert-butyldimethylsilylthymidine 5'-carboxaldehyde In tetrahydrofuran at -78 - 20℃; for 16h;

Reference： [1]Trafelet, Huldreich; Stulz, Eugen; Leumann, Christian [Helvetica Chimica Acta, 2001, vol. 84, # 1, p. 87 - 105]

9
[ 24589-99-9 ]
[ 28322-40-9 ]
[ 259819-17-5 ]

Yield	Reaction Conditions	Operation in experiment
99%	Stage #1: methyl 3-formyl-4-hydroxybenzoate With n-butyllithium; 1,1,1,3,3,3-hexamethyl-disilazane In tetrahydrofuran; hexane at 0℃; for 0.5h; Stage #2: isoamyltriphenylphosphonium bromide With n-butyllithium; 1,1,1,3,3,3-hexamethyl-disilazane In tetrahydrofuran; hexane for 3h; Further stages.;

Reference： [1]Lindsley, Craig W.; Chan, Lawrence K.; Goess, Brian C.; Joseph, Reni; Shair, Matthew D. [Journal of the American Chemical Society, 2000, vol. 122, # 2, p. 422 - 423]

10
[ 28322-40-9 ]
[ 20194-47-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 85 percent / n-BuLi / tetrahydrofuran / 1 h / 20 °C 2: H₂ / 5 percent Pd/C / ethyl acetate / 3 h / 20 °C
	Multi-step reaction with 2 steps 1: 85 percent / n-BuLi / 1 h / Ambient temperature 2: 100 percent / H₂ / 5percent Pd/C / ethyl acetate / 3 h / Ambient temperature
	Multi-step reaction with 2 steps 1: 85 percent / n-BuLi / tetrahydrofuran; hexane / 1 h / -10 - 20 °C 2: H₂ / Pd/C / ethyl acetate / 3 h / Ambient temperature

Multi-step reaction with 2 steps 1: n-butyllithium / tetrahydrofuran / 1 h / 20 °C 2: 5%-palladium/activated carbon; hydrogen / ethyl acetate

Reference： [1]Shioiri, Takayuki; Irako, Naoko [Tetrahedron, 2000, vol. 56, # 46, p. 9129 - 9142]
[2]Irako, Naoko; Shioiri, Takayuki [Tetrahedron Letters, 1998, vol. 39, # 32, p. 5793 - 5796]
[3]Shioiri, Takayuki; Terao, Yoshihiro; Irako, Naoko; Aoyama, Toyohiko [Tetrahedron, 1998, vol. 54, # 51, p. 15701 - 15710]
[4]Current Patent Assignee: ALBERTA RES CHEMICALS - WO2020/82162, 2020, A1

11
[ 28322-40-9 ]
[ 75853-51-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 85 percent / n-BuLi / tetrahydrofuran / 1 h / 20 °C 2: H₂ / 5 percent Pd/C / ethyl acetate / 3 h / 20 °C 3: 87 percent / PCC / CH₂Cl₂ / 2 h / 20 °C
	Multi-step reaction with 3 steps 1: 85 percent / n-BuLi / 1 h / Ambient temperature 2: 100 percent / H₂ / 5percent Pd/C / ethyl acetate / 3 h / Ambient temperature 3: 87 percent / PCC / 2 h / Ambient temperature
	Multi-step reaction with 3 steps 1: n-butyllithium / tetrahydrofuran / 1 h / 20 °C 2: 5%-palladium/activated carbon; hydrogen / ethyl acetate 3: dipyridinium dichromate

Reference： [1]Shioiri, Takayuki; Irako, Naoko [Tetrahedron, 2000, vol. 56, # 46, p. 9129 - 9142]
[2]Irako, Naoko; Shioiri, Takayuki [Tetrahedron Letters, 1998, vol. 39, # 32, p. 5793 - 5796]
[3]Current Patent Assignee: ALBERTA RES CHEMICALS - WO2020/82162, 2020, A1

12
[ 28322-40-9 ]
[ 21834-92-4 ]

Reference： [1]Journal of the Chemical Society. Perkin Transactions 1 (2001),2000,p. 2073 - 2078

13
[ 28322-40-9 ]
[ 252234-11-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: HN(TMS)2; n-butyl lithium / tetrahydrofuran; hexane / 0.5 h / 0 °C 1.2: 99 percent / HN(TMS)2; n-butyl lithium / tetrahydrofuran; hexane / 3 h 2.1: 63 percent / KOH / methanol; H₂O / 65 °C

Reference： [1]Lindsley, Craig W.; Chan, Lawrence K.; Goess, Brian C.; Joseph, Reni; Shair, Matthew D. [Journal of the American Chemical Society, 2000, vol. 122, # 2, p. 422 - 423]

14
[ 28322-40-9 ]
[ 252234-28-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: HN(TMS)2; n-butyl lithium / tetrahydrofuran; hexane / 0.5 h / 0 °C 1.2: 99 percent / HN(TMS)2; n-butyl lithium / tetrahydrofuran; hexane / 3 h 2.1: 63 percent / KOH / methanol; H₂O / 65 °C 3.1: 80 percent / PyBOP; diisopropylethylamine / dimethylformamide; CH₂Cl₂ / 0 - 20 °C

Reference： [1]Lindsley, Craig W.; Chan, Lawrence K.; Goess, Brian C.; Joseph, Reni; Shair, Matthew D. [Journal of the American Chemical Society, 2000, vol. 122, # 2, p. 422 - 423]

15
[ 28322-40-9 ]
(1S,2S,6aS,11bR,11cR)-2-(3-[(2-Hydroxy-ethylcarbamoyl)-methyl]-carbamoyl}-propyl)-1-isobutyl-6a-methoxy-4-oxo-1,2,4,6a,11b,11c-hexahydro-benzo[kl]xanthene-10-carboxylic acid 4-bromo-benzylamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: HN(TMS)2; n-butyl lithium / tetrahydrofuran; hexane / 0.5 h / 0 °C 1.2: 99 percent / HN(TMS)2; n-butyl lithium / tetrahydrofuran; hexane / 3 h 2.1: 63 percent / KOH / methanol; H₂O / 65 °C 3.1: 80 percent / PyBOP; diisopropylethylamine / dimethylformamide; CH₂Cl₂ / 0 - 20 °C 4.1: PhI(OAc)2 / CH₂Cl₂; tetrahydrofuran / 2 h / 25 °C 4.2: HF-pyridine / tetrahydrofuran / 2 h / 25 °C 4.3: 78 percent / TMSOMe / tetrahydrofuran / 2 h

Reference： [1]Lindsley, Craig W.; Chan, Lawrence K.; Goess, Brian C.; Joseph, Reni; Shair, Matthew D. [Journal of the American Chemical Society, 2000, vol. 122, # 2, p. 422 - 423]

16
[ 28322-40-9 ]
[ 70680-15-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 2: H₂ / 10 percent Pd/C / ethanol / 2327.17 Torr
	Multi-step reaction with 2 steps 1: 1.) n-butyllithium / 1.) ether, 25 deg C, 2 h, 2.) ether, 25 deg C, 18 h 2: 71 percent / H₂, trifluoroacetic acid / Pd on carbon / ethanol / 24 h / 2327.2 Torr

Reference： [1]Huffman, John W.; Lainton, Julia A. H.; Dai, Dong; Jordan, Robert D.; Duncan, Sammy G. [Life Sciences, 1995, vol. 56, # 23/24, p. 2021 - 2024]
[2]Huffman, John W.; Lainton, Julia A.H.; Banner, W. Kenneth; Duncan Jr., Sammy G.; Jordan, Robert D.; Yu, Shu; Dai, Dong; Martin, Billy R.; Wiley, Jenny L.; Compton, David R. [Tetrahedron, 1997, vol. 53, # 5, p. 1557 - 1576]

17
[ 28322-40-9 ]
[ 860504-71-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 2: H₂ / 10 percent Pd/C / ethanol / 2327.17 Torr 3: BBr₃ / CH₂Cl₂
	Multi-step reaction with 3 steps 1: 1.) n-butyllithium / 1.) ether, 25 deg C, 2 h, 2.) ether, 25 deg C, 18 h 2: 71 percent / H₂, trifluoroacetic acid / Pd on carbon / ethanol / 24 h / 2327.2 Torr 3: boron tribromide / CH₂Cl₂ / 0 - 25 °C

Reference： [1]Huffman, John W.; Lainton, Julia A. H.; Dai, Dong; Jordan, Robert D.; Duncan, Sammy G. [Life Sciences, 1995, vol. 56, # 23/24, p. 2021 - 2024]
[2]Huffman, John W.; Lainton, Julia A.H.; Banner, W. Kenneth; Duncan Jr., Sammy G.; Jordan, Robert D.; Yu, Shu; Dai, Dong; Martin, Billy R.; Wiley, Jenny L.; Compton, David R. [Tetrahedron, 1997, vol. 53, # 5, p. 1557 - 1576]

18
[ 28322-40-9 ]
4'-methyl-Δ⁸-THC [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 2: H₂ / 10 percent Pd/C / ethanol / 2327.17 Torr 3: BBr₃ / CH₂Cl₂ 4: HOTs / benzene
	Multi-step reaction with 4 steps 1: 1.) n-butyllithium / 1.) ether, 25 deg C, 2 h, 2.) ether, 25 deg C, 18 h 2: 71 percent / H₂, trifluoroacetic acid / Pd on carbon / ethanol / 24 h / 2327.2 Torr 3: boron tribromide / CH₂Cl₂ / 0 - 25 °C 4: 56 percent / p-toluenesulfonic acid monohydrate / benzene / 2.5 h / 80 °C

Reference： [1]Huffman, John W.; Lainton, Julia A. H.; Dai, Dong; Jordan, Robert D.; Duncan, Sammy G. [Life Sciences, 1995, vol. 56, # 23/24, p. 2021 - 2024]
[2]Huffman, John W.; Lainton, Julia A.H.; Banner, W. Kenneth; Duncan Jr., Sammy G.; Jordan, Robert D.; Yu, Shu; Dai, Dong; Martin, Billy R.; Wiley, Jenny L.; Compton, David R. [Tetrahedron, 1997, vol. 53, # 5, p. 1557 - 1576]

19
[ 28322-40-9 ]
[ 82903-20-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 7 steps 1: 2.4 N butylithium / diethyl ether / 1 h / Ambient temperature 2: benzyltriethylammonium chloride, 50 percent sodium hydroxide / H₂O / 72 h / 0 °C 3: 1.) Li; 2.) PTSA / 1.) NH₃(liquid); 2.) dioxane/water 4: p-toluenesulfonic acid / dioxane; H₂O / 1 h / Heating 5: 99 percent Chromat_. / pyridine 6: 5 percent trifluoroacetic acid / benzene / 72 h 7: 5 percent KOH / methanol / 1 h / Heating

Reference： [1]Zimmerman, Mary P.; Li, Hui-ting; Duax, William L.; Weeks, Charles M.; Djerassi, Carl [Journal of the American Chemical Society, 1984, vol. 106, # 19, p. 5602 - 5612]

20
[ 28322-40-9 ]
[ 71932-06-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 7 steps 1: 2.4 N butylithium / diethyl ether / 1 h / Ambient temperature 2: benzyltriethylammonium chloride, 50 percent sodium hydroxide / H₂O / 72 h / 0 °C 3: 1.) Li; 2.) PTSA / 1.) NH₃(liquid); 2.) dioxane/water 4: p-toluenesulfonic acid / dioxane; H₂O / 1 h / Heating 5: 99 percent Chromat_. / pyridine 6: 5 percent trifluoroacetic acid / benzene / 72 h 7: 5 percent KOH / methanol / 1 h / Heating

Reference： [1]Zimmerman, Mary P.; Li, Hui-ting; Duax, William L.; Weeks, Charles M.; Djerassi, Carl [Journal of the American Chemical Society, 1984, vol. 106, # 19, p. 5602 - 5612]

21
[ 28322-40-9 ]
[ 75871-95-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1: 2.4 N butylithium / diethyl ether / 1 h / Ambient temperature 2: MCPBA / CH₂Cl₂ / 7 h / Ambient temperature 3: 1.) lithium diphenylphosphide; 2.) methyl iodide / 1.) THF, 12 h; 2.) 30 min 4: benzyltriethylammonium chloride, 50 percent sodium hydroxide / H₂O / 72 h / 0 °C 5: 1.) Li; 2.) PTSA / 1.) NH₃(liquid); 2.) dioxane/water 6: p-toluenesulfonic acid / dioxane; H₂O / 1 h / Heating
	Multi-step reaction with 4 steps 1: 2.4 N butylithium / diethyl ether / 1 h / Ambient temperature 2: benzyltriethylammonium chloride, 50 percent sodium hydroxide / H₂O / 72 h / 0 °C 3: 1.) Li; 2.) PTSA / 1.) NH₃(liquid); 2.) dioxane/water 4: p-toluenesulfonic acid / dioxane; H₂O / 1 h / Heating

Reference： [1]Zimmerman, Mary P.; Li, Hui-ting; Duax, William L.; Weeks, Charles M.; Djerassi, Carl [Journal of the American Chemical Society, 1984, vol. 106, # 19, p. 5602 - 5612]
[2]Zimmerman, Mary P.; Li, Hui-ting; Duax, William L.; Weeks, Charles M.; Djerassi, Carl [Journal of the American Chemical Society, 1984, vol. 106, # 19, p. 5602 - 5612]

22
[ 28322-40-9 ]
[ 80227-02-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: 2.4 N butylithium / diethyl ether / 1 h / Ambient temperature 2: benzyltriethylammonium chloride, 50 percent sodium hydroxide / H₂O / 72 h / 0 °C 3: 1.) Li; 2.) PTSA / 1.) NH₃(liquid); 2.) dioxane/water 4: p-toluenesulfonic acid / dioxane; H₂O / 1 h / Heating

Reference： [1]Zimmerman, Mary P.; Li, Hui-ting; Duax, William L.; Weeks, Charles M.; Djerassi, Carl [Journal of the American Chemical Society, 1984, vol. 106, # 19, p. 5602 - 5612]

23
[ 28322-40-9 ]
[ 80227-03-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: 2.4 N butylithium / diethyl ether / 1 h / Ambient temperature 2: benzyltriethylammonium chloride, 50 percent sodium hydroxide / H₂O / 72 h / 0 °C 3: 1.) Li; 2.) PTSA / 1.) NH₃(liquid); 2.) dioxane/water 4: p-toluenesulfonic acid / dioxane; H₂O / 1 h / Heating

Reference： [1]Zimmerman, Mary P.; Li, Hui-ting; Duax, William L.; Weeks, Charles M.; Djerassi, Carl [Journal of the American Chemical Society, 1984, vol. 106, # 19, p. 5602 - 5612]

24
[ 28322-40-9 ]
[ 75917-89-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1: 2.4 N butylithium / diethyl ether / 1 h / Ambient temperature 2: MCPBA / CH₂Cl₂ / 7 h / Ambient temperature 3: 1.) lithium diphenylphosphide; 2.) methyl iodide / 1.) THF, 12 h; 2.) 30 min 4: benzyltriethylammonium chloride, 50 percent sodium hydroxide / H₂O / 72 h / 0 °C 5: 1.) Li; 2.) PTSA / 1.) NH₃(liquid); 2.) dioxane/water 6: p-toluenesulfonic acid / dioxane; H₂O / 1 h / Heating
	Multi-step reaction with 4 steps 1: 2.4 N butylithium / diethyl ether / 1 h / Ambient temperature 2: benzyltriethylammonium chloride, 50 percent sodium hydroxide / H₂O / 72 h / 0 °C 3: 1.) Li; 2.) PTSA / 1.) NH₃(liquid); 2.) dioxane/water 4: p-toluenesulfonic acid / dioxane; H₂O / 1 h / Heating

Reference： [1]Zimmerman, Mary P.; Li, Hui-ting; Duax, William L.; Weeks, Charles M.; Djerassi, Carl [Journal of the American Chemical Society, 1984, vol. 106, # 19, p. 5602 - 5612]
[2]Zimmerman, Mary P.; Li, Hui-ting; Duax, William L.; Weeks, Charles M.; Djerassi, Carl [Journal of the American Chemical Society, 1984, vol. 106, # 19, p. 5602 - 5612]

25
[ 28322-40-9 ]
[ 25819-80-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 2.4 N butylithium / diethyl ether / 1 h / Ambient temperature 2: MCPBA / CH₂Cl₂ / 7 h / Ambient temperature 3: 1.) lithium diphenylphosphide; 2.) methyl iodide / 1.) THF, 12 h; 2.) 30 min

Reference： [1]Zimmerman, Mary P.; Li, Hui-ting; Duax, William L.; Weeks, Charles M.; Djerassi, Carl [Journal of the American Chemical Society, 1984, vol. 106, # 19, p. 5602 - 5612]

26
[ 28322-40-9 ]
2-Isobutyl-3-[(S)-1-((1aR,3aR,3bS,5aS,6R,8aS,8bS,10R,10aR)-10-methoxy-3a,5a-dimethyl-hexadecahydro-cyclopenta[a]cyclopropa[2,3]cyclopenta[1,2-f]naphthalen-6-yl)-ethyl]-oxirane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 2.4 N butylithium / diethyl ether / 1 h / Ambient temperature 2: MCPBA / CH₂Cl₂ / 7 h / Ambient temperature

Reference： [1]Zimmerman, Mary P.; Li, Hui-ting; Duax, William L.; Weeks, Charles M.; Djerassi, Carl [Journal of the American Chemical Society, 1984, vol. 106, # 19, p. 5602 - 5612]

27
[ 28322-40-9 ]
(1aR,3aR,3bS,5aR,6R,8aS,8bS,10R,10aR)-6-[(R)-1-((1R,2R)-2-Isobutyl-cyclopropyl)-ethyl]-10-methoxy-3a,5a-dimethyl-hexadecahydro-cyclopenta[a]cyclopropa[2,3]cyclopenta[1,2-f]naphthalene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: 2.4 N butylithium / diethyl ether / 1 h / Ambient temperature 2: MCPBA / CH₂Cl₂ / 7 h / Ambient temperature 3: 1.) lithium diphenylphosphide; 2.) methyl iodide / 1.) THF, 12 h; 2.) 30 min 4: benzyltriethylammonium chloride, 50 percent sodium hydroxide / H₂O / 72 h / 0 °C 5: 1.) Li; 2.) PTSA / 1.) NH₃(liquid); 2.) dioxane/water
	Multi-step reaction with 3 steps 1: 2.4 N butylithium / diethyl ether / 1 h / Ambient temperature 2: benzyltriethylammonium chloride, 50 percent sodium hydroxide / H₂O / 72 h / 0 °C 3: 1.) Li; 2.) PTSA / 1.) NH₃(liquid); 2.) dioxane/water

Reference： [1]Zimmerman, Mary P.; Li, Hui-ting; Duax, William L.; Weeks, Charles M.; Djerassi, Carl [Journal of the American Chemical Society, 1984, vol. 106, # 19, p. 5602 - 5612]
[2]Zimmerman, Mary P.; Li, Hui-ting; Duax, William L.; Weeks, Charles M.; Djerassi, Carl [Journal of the American Chemical Society, 1984, vol. 106, # 19, p. 5602 - 5612]

28
[ 28322-40-9 ]
(1aR,3aR,3bS,5aR,6R,8aS,8bS,10R,10aR)-6-[(R)-1-((1R,2S)-2-Isobutyl-cyclopropyl)-ethyl]-10-methoxy-3a,5a-dimethyl-hexadecahydro-cyclopenta[a]cyclopropa[2,3]cyclopenta[1,2-f]naphthalene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 2.4 N butylithium / diethyl ether / 1 h / Ambient temperature 2: benzyltriethylammonium chloride, 50 percent sodium hydroxide / H₂O / 72 h / 0 °C 3: 1.) Li; 2.) PTSA / 1.) NH₃(liquid); 2.) dioxane/water

Reference： [1]Zimmerman, Mary P.; Li, Hui-ting; Duax, William L.; Weeks, Charles M.; Djerassi, Carl [Journal of the American Chemical Society, 1984, vol. 106, # 19, p. 5602 - 5612]

29
[ 28322-40-9 ]
(1aR,3aR,3bS,5aR,6R,8aS,8bS,10R,10aR)-6-[(R)-1-((1S,2R)-2-Isobutyl-cyclopropyl)-ethyl]-10-methoxy-3a,5a-dimethyl-hexadecahydro-cyclopenta[a]cyclopropa[2,3]cyclopenta[1,2-f]naphthalene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 2.4 N butylithium / diethyl ether / 1 h / Ambient temperature 2: benzyltriethylammonium chloride, 50 percent sodium hydroxide / H₂O / 72 h / 0 °C 3: 1.) Li; 2.) PTSA / 1.) NH₃(liquid); 2.) dioxane/water

Reference： [1]Zimmerman, Mary P.; Li, Hui-ting; Duax, William L.; Weeks, Charles M.; Djerassi, Carl [Journal of the American Chemical Society, 1984, vol. 106, # 19, p. 5602 - 5612]

30
[ 28322-40-9 ]
(1aR,3aR,3bS,5aR,6R,8aS,8bS,10R,10aR)-6-[(R)-1-((1S,2S)-2-Isobutyl-cyclopropyl)-ethyl]-10-methoxy-3a,5a-dimethyl-hexadecahydro-cyclopenta[a]cyclopropa[2,3]cyclopenta[1,2-f]naphthalene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: 2.4 N butylithium / diethyl ether / 1 h / Ambient temperature 2: MCPBA / CH₂Cl₂ / 7 h / Ambient temperature 3: 1.) lithium diphenylphosphide; 2.) methyl iodide / 1.) THF, 12 h; 2.) 30 min 4: benzyltriethylammonium chloride, 50 percent sodium hydroxide / H₂O / 72 h / 0 °C 5: 1.) Li; 2.) PTSA / 1.) NH₃(liquid); 2.) dioxane/water
	Multi-step reaction with 3 steps 1: 2.4 N butylithium / diethyl ether / 1 h / Ambient temperature 2: benzyltriethylammonium chloride, 50 percent sodium hydroxide / H₂O / 72 h / 0 °C 3: 1.) Li; 2.) PTSA / 1.) NH₃(liquid); 2.) dioxane/water

Reference： [1]Zimmerman, Mary P.; Li, Hui-ting; Duax, William L.; Weeks, Charles M.; Djerassi, Carl [Journal of the American Chemical Society, 1984, vol. 106, # 19, p. 5602 - 5612]
[2]Zimmerman, Mary P.; Li, Hui-ting; Duax, William L.; Weeks, Charles M.; Djerassi, Carl [Journal of the American Chemical Society, 1984, vol. 106, # 19, p. 5602 - 5612]

31
[ 28322-40-9 ]
[ 80227-06-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 2.4 N butylithium / diethyl ether / 1 h / Ambient temperature 2: benzyltriethylammonium chloride, 50 percent sodium hydroxide / H₂O / 72 h / 0 °C

Reference： [1]Zimmerman, Mary P.; Li, Hui-ting; Duax, William L.; Weeks, Charles M.; Djerassi, Carl [Journal of the American Chemical Society, 1984, vol. 106, # 19, p. 5602 - 5612]

32
[ 28322-40-9 ]
[ 91237-13-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: 2.4 N butylithium / diethyl ether / 1 h / Ambient temperature 2: MCPBA / CH₂Cl₂ / 7 h / Ambient temperature 3: 1.) lithium diphenylphosphide; 2.) methyl iodide / 1.) THF, 12 h; 2.) 30 min 4: benzyltriethylammonium chloride, 50 percent sodium hydroxide / H₂O / 72 h / 0 °C
	Multi-step reaction with 2 steps 1: 2.4 N butylithium / diethyl ether / 1 h / Ambient temperature 2: benzyltriethylammonium chloride, 50 percent sodium hydroxide / H₂O / 72 h / 0 °C

Reference： [1]Zimmerman, Mary P.; Li, Hui-ting; Duax, William L.; Weeks, Charles M.; Djerassi, Carl [Journal of the American Chemical Society, 1984, vol. 106, # 19, p. 5602 - 5612]
[2]Zimmerman, Mary P.; Li, Hui-ting; Duax, William L.; Weeks, Charles M.; Djerassi, Carl [Journal of the American Chemical Society, 1984, vol. 106, # 19, p. 5602 - 5612]

33
[ 28322-40-9 ]
[ 80227-07-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: 2.4 N butylithium / diethyl ether / 1 h / Ambient temperature 2: MCPBA / CH₂Cl₂ / 7 h / Ambient temperature 3: 1.) lithium diphenylphosphide; 2.) methyl iodide / 1.) THF, 12 h; 2.) 30 min 4: benzyltriethylammonium chloride, 50 percent sodium hydroxide / H₂O / 72 h / 0 °C
	Multi-step reaction with 2 steps 1: 2.4 N butylithium / diethyl ether / 1 h / Ambient temperature 2: benzyltriethylammonium chloride, 50 percent sodium hydroxide / H₂O / 72 h / 0 °C

Reference： [1]Zimmerman, Mary P.; Li, Hui-ting; Duax, William L.; Weeks, Charles M.; Djerassi, Carl [Journal of the American Chemical Society, 1984, vol. 106, # 19, p. 5602 - 5612]
[2]Zimmerman, Mary P.; Li, Hui-ting; Duax, William L.; Weeks, Charles M.; Djerassi, Carl [Journal of the American Chemical Society, 1984, vol. 106, # 19, p. 5602 - 5612]

34
[ 28322-40-9 ]
[ 80186-24-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 2.4 N butylithium / diethyl ether / 1 h / Ambient temperature 2: benzyltriethylammonium chloride, 50 percent sodium hydroxide / H₂O / 72 h / 0 °C

Reference： [1]Zimmerman, Mary P.; Li, Hui-ting; Duax, William L.; Weeks, Charles M.; Djerassi, Carl [Journal of the American Chemical Society, 1984, vol. 106, # 19, p. 5602 - 5612]

35
[ 28322-40-9 ]
[ 91157-14-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1: 2.4 N butylithium / diethyl ether / 1 h / Ambient temperature 2: benzyltriethylammonium chloride, 50 percent sodium hydroxide / H₂O / 72 h / 0 °C 3: 1.) Li; 2.) PTSA / 1.) NH₃(liquid); 2.) dioxane/water 4: p-toluenesulfonic acid / dioxane; H₂O / 1 h / Heating 5: 99 percent Chromat_. / pyridine 6: 5 percent trifluoroacetic acid / benzene / 72 h

Reference： [1]Zimmerman, Mary P.; Li, Hui-ting; Duax, William L.; Weeks, Charles M.; Djerassi, Carl [Journal of the American Chemical Society, 1984, vol. 106, # 19, p. 5602 - 5612]

36
[ 28322-40-9 ]
[ 91157-06-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 7 steps 1: 2.4 N butylithium / diethyl ether / 1 h / Ambient temperature 2: MCPBA / CH₂Cl₂ / 7 h / Ambient temperature 3: 1.) lithium diphenylphosphide; 2.) methyl iodide / 1.) THF, 12 h; 2.) 30 min 4: benzyltriethylammonium chloride, 50 percent sodium hydroxide / H₂O / 72 h / 0 °C 5: 1.) Li; 2.) PTSA / 1.) NH₃(liquid); 2.) dioxane/water 6: p-toluenesulfonic acid / dioxane; H₂O / 1 h / Heating 7: 99 percent Chromat_. / pyridine
	Multi-step reaction with 5 steps 1: 2.4 N butylithium / diethyl ether / 1 h / Ambient temperature 2: benzyltriethylammonium chloride, 50 percent sodium hydroxide / H₂O / 72 h / 0 °C 3: 1.) Li; 2.) PTSA / 1.) NH₃(liquid); 2.) dioxane/water 4: p-toluenesulfonic acid / dioxane; H₂O / 1 h / Heating 5: 99 percent Chromat_. / pyridine

Reference： [1]Zimmerman, Mary P.; Li, Hui-ting; Duax, William L.; Weeks, Charles M.; Djerassi, Carl [Journal of the American Chemical Society, 1984, vol. 106, # 19, p. 5602 - 5612]
[2]Zimmerman, Mary P.; Li, Hui-ting; Duax, William L.; Weeks, Charles M.; Djerassi, Carl [Journal of the American Chemical Society, 1984, vol. 106, # 19, p. 5602 - 5612]

37
[ 28322-40-9 ]
[ 91199-77-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 7 steps 1: 2.4 N butylithium / diethyl ether / 1 h / Ambient temperature 2: MCPBA / CH₂Cl₂ / 7 h / Ambient temperature 3: 1.) lithium diphenylphosphide; 2.) methyl iodide / 1.) THF, 12 h; 2.) 30 min 4: benzyltriethylammonium chloride, 50 percent sodium hydroxide / H₂O / 72 h / 0 °C 5: 1.) Li; 2.) PTSA / 1.) NH₃(liquid); 2.) dioxane/water 6: p-toluenesulfonic acid / dioxane; H₂O / 1 h / Heating 7: 99 percent Chromat_. / pyridine
	Multi-step reaction with 5 steps 1: 2.4 N butylithium / diethyl ether / 1 h / Ambient temperature 2: benzyltriethylammonium chloride, 50 percent sodium hydroxide / H₂O / 72 h / 0 °C 3: 1.) Li; 2.) PTSA / 1.) NH₃(liquid); 2.) dioxane/water 4: p-toluenesulfonic acid / dioxane; H₂O / 1 h / Heating 5: 99 percent Chromat_. / pyridine

Reference： [1]Zimmerman, Mary P.; Li, Hui-ting; Duax, William L.; Weeks, Charles M.; Djerassi, Carl [Journal of the American Chemical Society, 1984, vol. 106, # 19, p. 5602 - 5612]
[2]Zimmerman, Mary P.; Li, Hui-ting; Duax, William L.; Weeks, Charles M.; Djerassi, Carl [Journal of the American Chemical Society, 1984, vol. 106, # 19, p. 5602 - 5612]

38
Boc-cyclohexylalanine methyl ester [ No CAS ]
[ 28322-40-9 ]
[ 999-97-3 ]
[ 119618-56-3 ]

Yield	Reaction Conditions	Operation in experiment
16.5 g (38%)	With diisobutylaluminium hydride In tetrahydrofuran; dimethyl sulfoxide; toluene	1 2(S)-t-Butyloxycarbonylamino-1-cyclohexyl-6-methylhept-3-ene EXAMPLE 1 2(S)-t-Butyloxycarbonylamino-1-cyclohexyl-6-methylhept-3-ene To a stirred -78° C. solution of Boc-cyclohexylalanine methyl ester (40 g, 140 mmol) in anhydrous toluene (250 ml) was added diisobutylaluminum hydride (130M %, 1.5M solution in toluene, 121.4 ml) at a rate to keep the internal temperature below -60° C. After stirring for an additional 20 minutes at -78° C., the aldehyde solution is used immediately as described below. To a potassium hydride (35% dispersion in oil, 32.09 g) suspension in a 0° C. mixture of anhydrous THF/DMSO (1000 ml/200 ml) under dry N2 was added 1,1,1,3,3,3-hexamethyldisilazane (209M %, 49.07 g) dropwise. After stirring at 0° C. for 1 hour, the resulting solution was added via cannula to a 0° C. flask containing isopentyltriphenylphosphonium bromide (209M %, 125.66 g). The mixture was stirred vigorously for 1 hour at which time it was cooled to -78° C. The -78° C. aldehyde solution prepared above was then added via cannula. After stirring at -78° C. for 15 minutes, the mixture was allowed to slowly warm to room temperature and then heated to 40° C. for 12 hours. The mixture was then cooled to room temperature and quenched with methanol (7.65 ml) followed by aqueous Rochelle salts (100 ml saturated solution and 500 ml H2 O). The mixture was then extracted with ethyl acetate (2*). The combined extracts were washed with water and brine. Drying (MgSO4) and evaporating provided crude alkene which was chromatographed on silica gel (ether/hexane) to give 16.5 g (38%) of the desired compound as an 85:15 mixture of cis:trans isomers. m.p.=53°-55° C. Mass spectrum: M+ =309. Anal. Calcd. for C19 H35 NO2: C, 73.7; H, 11.4; N, 4.5. Found: C, 73.8; H, 11.4; N, 4.5.
16.5 g (38%)	With diisobutylaluminium hydride In tetrahydrofuran; dimethyl sulfoxide; toluene	19 2(S)-t-Butyloxycarbonylamino-1-cyclohexyl-6-methylhept-3-ene EXAMPLE 19 2(S)-t-Butyloxycarbonylamino-1-cyclohexyl-6-methylhept-3-ene To a stirred -78° C. solution of Boc-cyclohexylalanine methyl ester (40 g, 140 mmol) in anhydrous toluene (250 ml) was added diisobutylaluminum hydride (130M %, 1.5M solution in toluene, 121.4 ml) at a rate to keep the internal temperature below -60° C. After stirring for an additional 20 minutes at -78° C., the aldehyde solution is used immediately as described below. To a potassium hydride (35% dispersion in oil, 32.09 g) suspension in a 0° C. mixture of anhydrous THF/DMSO (1000 ml/200 ml) under dry N2 was added 1,1,1,3,3,3-hexamethyldisilazane (209M %, 49.07 g) dropwise. After stirring at 0° C. for 1 hour, the resulting solution was added via cannula to a 0° C. flask containing isopentyltriphenylphosphonium bromide (209M %, 125.66 g). The mixture was stirred vigorously for 1 hour at which time it was cooled to -78° C. The -78° C. aldehyde solution prepared above was then added via cannula. After stirring at -78° C. for 15 minutes, the mixture was allowed to slowly warm to room temperature and then heated to 40° C. for 12 hours. The mixture was then cooled to room temperature and quenched with methanol (7.65 ml) followed by aqueous Rochelle salts (100 ml saturated solution and 500 ml H2 O). The mixture was then extracted with ethyl acetate (2x). The combined extracts were washed with water and brine. Drying (MgSO4) and evaporating provided crude alkene which was chromatographed on silica gel (ether/hexane) to give 16.5 g (38%) of the desired compound as an 85:15 mixture of cis:trans isomers. Mp=53°-55° C. Mass spectrum: M+ =309. Anal Calcd. for C19 H35 NO2: C, 73.7; H, 11.4; N, 4.5. Found: C, 73.8; H, 11.4; N, 4.5.

Reference： [1]Current Patent Assignee: ABBOTT LABORATORIES INC - US5164388, 1992, A
[2]Current Patent Assignee: ABBOTT LABORATORIES INC - US4994477, 1991, A

39
Boc-cyclohexylalanine methyl ester [ No CAS ]
[ 7732-18-5 ]
[ 28322-40-9 ]
[ 999-97-3 ]
[ 119618-56-3 ]

Yield	Reaction Conditions	Operation in experiment
16.5 g (38%)	With diisobutylaluminium hydride In dimethyl sulfoxide; toluene	11.c c. c. 2(S)-t-Butyloxycarbonylamino-1-cyclohexyl-6-methylhept-3-ene To a stirred -78° C. solution of Boc-cyclohexylalanine methyl ester (40 g, 140 mmol) in anhydrous toluene (250 mL) was added diisobutylaluminum hydride (130 M %, 1 5 M solution in toluene, 121.4 mL) at a rate to keep the internal temperature below -60° C. After stirring for an additional 20 minutes at -78° C., the aldehyde solution is used immediately as described below. To a potassium hydride (35% dispersion in oil, 32.09 g) suspension in a 0° C. mixture of anhydrous THF/DMSO (1000 mL/200 mL) under dry N added 1,1,1,3,3,3-hexamethyldisilazane (209 M %, 49.07 g) dropwise. After stirring at 0° C. for 1 hour, the resulting solution was added via cannula to a 0° C. flask containing isopentyltriphenylphosphonium bromide (209 M %, 125.66 g). The mixture was stirred vigorously for 1 hour at which time it was cooled to -78° C. The -78° C. aldehyde solution prepared above was then added via cannula. After stirring at -78° C. for 15 minutes, the mixture was allowed to slowly warm to room temperature and then heated to 40° C. for 12 hours. The mixture was then cooled to room temperature and quenched with methanol (7.65 mL) followed by aqueous Rochelle salts (100 mL saturated solution and 500 mL H2 O). The mixture was then extracted with ethyl acetate (2*). The combined extracts were washed with water and brine. Drying (MgSO4) and evaporating provided crude alkene which was chromatographed on silica gel (ether/hexane) to give 16.5 g (38%) of the desired compound as an 85:15 mixture of cis:trans isomers. Mp=53-55° C. Mass spectrum: M+ =309. Analysis calculated for C19 H35 NO2: C, 73.7; H, 11.4; N, 4.5. Found: C, 73.8; H, 11.4; N, 4.5.
16.5 g (38%)	With diisobutylaluminium hydride In tetrahydrofuran; dimethyl sulfoxide; toluene	11.c c. c. 2(S)-t-Butyloxycarbonylamino-1-cyclohexyl-6-methylhept-3-ene To a stirred -78° C. solution of Boc-cyclohexylalanine methyl ester (40 g, 140 mmol) in anhydrous toluene (250 mL) was added diisobutylaluminum hydride (130M %, 1.5M solution in toluene, 121.4 mL) at a rate to keep the internal temperature below -60° C. After stirring for an additional 20 minutes at -78° C., the aldehyde solution is used immediately as described below. To a potassium hydride (35% dispersion in oil, 32.09 g) suspension in a 0° C. mixture of anhydrous THF/DMSO (1000 mL/200 mL) under dry N2 was added 1,1,1,3,3,3-hexamethyldisilazane (209M %, 49.07 g) dropwise. After stirring at 0° C. for 1 hour, the resulting solution was added via cannula to a 0° C. flask containing isopentyltriphenylphosphonium bromide (209 M %, 125.66 g). The mixture was stirred vigorously for 1 hour at which time it was cooled to -78° C. The -78° C. aldehyde solution prepared above was then added via cannula. After stirring at -78° C. for 15 minutes, the mixture was allowed to slowly warm to room temperature and then heated to 40° C. for 12 hours. The mixture was then cooled to room temperature and quenched with methanol (7.65 mL) followed by aqueous Rochelle salts (100 mL saturated solution and 500 mL H2 O). The mixture was then extracted with ethyl acetate (2*). The combined extracts were washed with water and brine. Drying (MgSO4) and evaporating provided crude alkene which was chromatographed on silica gel (ether/hexane) to give 16.5 g (38%) of the desired compound as an 85:15 mixture of cis:trans isomers. Mp=53°-55° C. Mass spectrum: M+ =309. Analysis calculated for C19 H35 NO2: C, 73.7; H, 11.4; N, 4.5. Found: C, 73.8; H, 11.4; N, 4.5.
16.5 g (38%)	With diisobutylaluminium hydride In tetrahydrofuran; dimethyl sulfoxide; toluene	17 (2S)-t-Butyloxycarbonylamino-1-cyclohexyl-6-methylhept-3-ene EXAMPLE 17 (2S)-t-Butyloxycarbonylamino-1-cyclohexyl-6-methylhept-3-ene To a stirred -78° C. solution of Boc-cyclohexylalanine methyl ester (40 g, 140 mmol) in anhydrous toluene (250 ml) was added diisobutylaluminum hydride (130M %, 1.5M solution in toluene, 121.4 ml) at a rate to keep the internal temperature below -60° C. After stirring for an additional 20 minutes at -78° C., the aldehyde solution is used immediately as described below. To a potassium hydride (35% dispersion in oil, 32.09 g) suspension in a 0° C. mixture of anhydrous THF/DMSO (1000 ml/200 ml) under dry N2 was added 1,1,1,3,3,3-hexamethyldisilazane (209M %, 49.07 g) dropwise. After stirring at 0° C. for 1 hour, the resulting solution was added via cannula to a 0° C. flask containing isopentyltriphenylphosphonium bromide (209M %, 125.66 g). The mixture was stirred vigorously for 1 hour at which time it was cooled to -78° C. The -78° C. aldehyde solution prepared above was then added via cannula. After stirring at -78° C. for 15 minutes, the mixture was allowed to slowly warm to room temperature and then heated to 40° C. for 12 hours. The mixture was then cooled to room temperature and quenched with methanol (7.65 ml) followed by aqueous Rochelle salts (100 ml saturated solution and 500 ml H2 O). The mixture was then extracted with ethyl acetate (2x). The combined extracts were washed with water and brine. Drying (MgSO4) and evaporating provided crude alkene which was chromatographed on silica gel (ether/hexane) to give 16.5 g (38%) of the desired compound as an 85:15 mixture of cis:trans isomers. Mp=53°-55° C. Mass spectrum: M+ =309. Anal. calcd. for C19 H35 NO2: C, 73.7; H, 11.4; N, 4.5. Found: C, 73.8; H, 11.4; N, 4.5.

Reference： [1]Current Patent Assignee: ABBOTT LABORATORIES INC - US4927807, 1990, A
[2]Current Patent Assignee: ABBOTT LABORATORIES INC - US5036051, 1991, A
[3]Current Patent Assignee: ABBOTT LABORATORIES INC - US4725583, 1988, A

40
[ 112-54-9 ]
[ 28322-40-9 ]
[ 1226754-94-4 ]

Yield	Reaction Conditions	Operation in experiment
56%	Stage #1: isoamyltriphenylphosphonium bromide With sodium hexamethyldisilazane In tetrahydrofuran; diethyl ether at 0℃; Inert atmosphere; Stage #2: Dodecanal In tetrahydrofuran; diethyl ether at 0 - 20℃; Inert atmosphere; optical yield given as %de;

Reference： [1]Mundal, Devon A.; Avetta Jr., Christopher T.; Thomson, Regan J. [Nature Chemistry, 2010, vol. 2, # 4, p. 294 - 297]

41
[ 1252023-86-1 ]
[ 28322-40-9 ]
5α-cholesta-9(11),22-dien-3β-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
47%	Stage #1: isoamyltriphenylphosphonium bromide With n-butyllithium In tetrahydrofuran; hexane at 0℃; Stage #2: C₂₂H₃₄O₂ In tetrahydrofuran; hexane at 0 - 20℃;

Reference： [1]Location in patent: experimental part Kongkathip, Boonsong; Hasakunpaisarn, Anuch; Boonananwong, Suthinee; Kongkathip, Ngampong [Steroids, 2010, vol. 75, # 12, p. 834 - 847]

42
[ 28322-40-9 ]
[ 107-02-8 ]
[ 2783-11-1 ]

Yield	Reaction Conditions	Operation in experiment
55%	With potassium hexamethylsilazane In tetrahydrofuran at -78 - 20℃; for 2h; Inert atmosphere;

Reference： [1]Kliman, Laura T.; Mlynarski, Scott N.; Ferris, Grace E.; Morken, James P. [Angewandte Chemie - International Edition, 2012, vol. 51, # 2, p. 521 - 524]

43
[ 3391-87-5 ]
[ 28322-40-9 ]
[ 1374645-89-2 ]

Yield	Reaction Conditions	Operation in experiment
65%	Stage #1: isoamyltriphenylphosphonium bromide With potassium <i>tert</i>-butylate In tetrahydrofuran at 20℃; for 0.5h; Inert atmosphere; Stage #2: l-menthone In tetrahydrofuran at 80℃; for 48h; Inert atmosphere;

Reference： [1]Location in patent: experimental part Fernandes, Rodney A.; Chaudhari, Dipali A. [European Journal of Organic Chemistry, 2012, # 10, p. 1945 - 1952]

44
[ 28322-40-9 ]
[ 100-52-7 ]
[ 54624-34-9 ]

Yield	Reaction Conditions	Operation in experiment
92%	Stage #1: isoamyltriphenylphosphonium bromide With potassium <i>tert</i>-butylate In tetrahydrofuran; toluene for 4h; Inert atmosphere; Stage #2: benzaldehyde In tetrahydrofuran; toluene at -78 - 20℃; for 3h; Inert atmosphere;

Reference： [1]Bess, Elizabeth N.; Deluca, Ryan J.; Tindall, Daniel J.; Oderinde, Martins S.; Roizen, Jennifer L.; Du Bois; Sigman, Matthew S. [Journal of the American Chemical Society, 2014, vol. 136, # 15, p. 5783 - 5789]

45
silver(I) bromide [ No CAS ]
[ 28322-40-9 ]
[Ph₃P(i-Am)]₂[(silver)₂(bromide)₄] [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
79%	In dimethyl sulfoxide at 20℃; for 24h;	General procedure: A mixture of ethylenebis(triphenylphosphonium) dichloride (0.623 g, 1.00mmol) and silver chloride (0.286 g, 2.00 mmol) in dimethylsulfoxide (10 mL) was allowed to stand at 20°C for 24 h. After the solvent was slowly evaporated, colorless crystals of complex I

Reference： [1]Sharutin; Sharutina; Senchurin; Neudachina [Russian Journal of Inorganic Chemistry, 2016, vol. 61, # 4, p. 451 - 460][Zh. Neorg. Khim., 2016, vol. 61, # 4, p. 472 - 481,10]

46
C₂₄H₃₆O₄ [ No CAS ]
[ 28322-40-9 ]
C₂₉H₄₆O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
4.5 g	Stage #1: isoamyltriphenylphosphonium bromide With n-butyllithium In tetrahydrofuran at -78℃; for 1h; Inert atmosphere; Stage #2: C₂₄H₃₆O₄ In tetrahydrofuran at -78 - 20℃; Inert atmosphere;	19 4.19 (4S,5S)-4-((Benzyloxy)methyl)-2,2-dimethyl-5-((1Z,4Z)-7-methylocta-1,4-dien-1-yl)-1,3-dioxolane (30) 4.19 (4S,5S)-4-((Benzyloxy)methyl)-2,2-dimethyl-5-((1Z,4Z)-7-methylocta-1,4-dien-1-yl)-1,3-dioxolane (30) To the alcohol 31 (5.0 g, 12.8 mmol) dissolved in a solvent mixture THF:DMSO (1:1, 60 mL), was added at once IBX (5.38 g, 19.2 mmol) and stirred for 2 h at room temperature. The reaction mixture was diluted with ice cold water (70 mL) and extracted with CH2Cl2 (5*50 mL). Combined organic layers were washed with saturated NaHCO3 (120 mL), dried over anhydrous Na2SO4 and concentrated under reduced pressure yielded the crude aldehyde (5.0 g, 12.8 mmol) which was directly used for further step without purification. (3-methyl)butyl triphenyl phosphonium bromide (15.9 g, 38.6 mmol) was dissolved in dry THF (90 mL) and cooled to -78 °C. To this n-BuLi (13.9mL, 34.7mmol, 2.5M) was added drop wise and stirred for 1h at the same temperature. During this time reaction color was changed from colorless to brick red. To this, the crude aldehyde dissolved in anhydrous THF (30mL) was added drop wise and stirred for overnight after allowing the reaction mixture to warm to room temperature. The reaction mixture was quenched with saturated ammonium chloride 30mL) at 0°C. The reaction mixture was extracted with ethyl acetate (5×30mL), dried over anhydrous Na2SO4 and concentrated under reduced pressure. The resulting crude was purified through silica gel (60-120mesh) column chromatography to afford compound (30) as colorless liquid (4.5g, 10.2mmol, 81% over two steps). Rf=0.75 (20% EtOAc-Hexane). [α]D25=+4.98 (c, 1.08, CHCl3). IR νmax: 2925, 2857, 1733, 1457, 1372, 1219, 1165, 1080, 1027, 914, 862, 745, 698cm-1. 1H NMR (300MHz, CDCl3): δ 7.35-7.26 (m, 5H), 5.70-5.63 (m, 1H), 5.42-5.33 (m, 3H), 4.66-4.61 (m, 1H), 4.59 (s, 2H), 3.86 (dt, J=5.4, 3.0Hz, 1H), 3.62-3.58 (m, 1H), 3.56-3.52 (m, 1H), 2.15-2.07 (m, 1H), 2.05-1.97 (m, 3H), 1.93-1.89 (m, 2H), 1.63-1.55 (m, 1H), 1.44 (s, 6H), 1.36-1.19 (m, 16H), 0.89 (d, 6H, J=6.4Hz) ppm. 13C NMR (75MHz, CDCl3): δ 137.93, 136.31, 130.45, 128.44, 128.22, 127.51, 126.04, 109.07, 80.36, 73.47, 73.36, 69.13, 36.29, 29.66, 29.52, 29.40, 29.36, 29.23, 29.14, 28.60, 27.66, 27.21, 27.11, 26.91, 22.32ppm. MS (ESI): m/z 465 [M+Na]+. HRMS (ESI) m/z calculated for C29H46NaO3 465.3339, found 465.3374.

Reference： [1]Gangadhar, Pamarthi; Sathish Reddy; Srihari, Pabbaraja [Tetrahedron, 2016, vol. 72, # 38, p. 5807 - 5817]

47
ruthenium(III) chloride trihydrate [ No CAS ]
[ 28322-40-9 ]
isoamyltriphenylphosphonium perruthenate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
94%	Stage #1: ruthenium(III) chloride trihydrate With sodium bromate; sodium carbonate In water at 20℃; for 2h; Stage #2: isoamyltriphenylphosphonium bromide In water at 20℃; for 0.05h;
	Stage #1: ruthenium(III) chloride trihydrate With sodium bromate; sodium carbonate In water at 20℃; for 2h; Stage #2: isoamyltriphenylphosphonium bromide In water at 20℃; for 0.05h;

Reference： [1]Moore, Peter W.; Read, Christopher D. G.; Bernhardt, Paul V.; Williams, Craig M. [Chemistry - A European Journal, 2018, vol. 24, # 18, p. 4556 - 4561]
[2]Dallaston, Madeleine A.; Bettencourt, Christian J.; Chow, Sharon; Gebhardt, Joshua; Spangler, Jordan; Johnston, Martin R.; Wall, Craig; Brusnahan, Jason S.; Williams, Craig M. [Chemistry - A European Journal, 2019, vol. 25, # 41, p. 9614 - 9618]

48
[ 2960-66-9 ]
[ 28322-40-9 ]
[ 62903-88-2 ]

Yield	Reaction Conditions	Operation in experiment
86%	Stage #1: isoamyltriphenylphosphonium bromide With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Inert atmosphere; Stage #2: 4-oxo-but-2-enoic acid ethyl ester In tetrahydrofuran; hexane at 20℃; for 0.5h;	64.1 Step 1. Synthesis of (2E,4E)-ethyl 7-methylocta-2,4-dienoate (64-1) n-BuLi (14.5 mL, 36.29 mmol, 2.5 M in 44 n-hexane) was added into a solution of 400 isopentyltriphenylphosphonium bromide (15.0 g, 36.29 mmol) in 26 THF (50 mL) at -78°C in a nitrogen atmosphere, after which a resulting mixture was stirred at the same temperature for 1 hour. 401 Ethyl 4-oxobut-2-enoate (1.55 g, 12.09 mmol) was slowly added dropwise into the resulting mixture, after which the resulting mixture was stirred for 30 minutes with a temperature rising to room temperature. A reaction mixture was cooled at 0°C, after which a saturated solution of 320 ammonium chloride was added dropwise into a resulting product, so as to complete a reaction and perform an extraction with diethyl ether. An organic layer was dried over anhydrous MgSO4, filtered and concentrated under reduced pressure. A resulting concentrate was purified by means of a silica gel column chromatography, so as to obtain the 402 title compound (64-1) (1.89 g, 10.37 mmol, 86%). (0433) 1HNMR(400 MHz, CDCl3); 5.60 (dd, J = 15.2, 11.2 Hz, 1H), 6.17 (t, J = 11.2 Hz, 1H), 5.91-5.84 (m, 2H), 4.21 (q, J = 7.2 Hz, 2H), 2.20 (t, J = 7.2 Hz, 2H), 1.72-1.65 (m, 1H), 1.29 (t, J = 7.2 Hz, 3H), 0.93 (d, J = 6.8 Hz, 6H)

Reference： [1]Current Patent Assignee: JEIL PHARMA HOLDINGS INC - EP3404033, 2018, A1 Location in patent: Paragraph 0431-0433

49
[ 28322-40-9 ]
[ 100-52-7 ]
(4-methylpent-1-en-1-yl)benzene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: isoamyltriphenylphosphonium bromide With n-butyllithium In tetrahydrofuran; cyclohexane at 0℃; for 1h; Schlenk technique; Inert atmosphere; Stage #2: benzaldehyde In tetrahydrofuran; cyclohexane at 20℃; for 18h; Schlenk technique; Inert atmosphere;
	Stage #1: isoamyltriphenylphosphonium bromide With n-butyllithium In tetrahydrofuran at -78 - 20℃; for 3h; Inert atmosphere; Stage #2: benzaldehyde In tetrahydrofuran at 20℃; for 5h; Inert atmosphere;	General procedure A General procedure: To a suspension of butyltriphenylphosphonium (10 mmol, 1.0 eq) in THF (30 mL) were added nBuLi (1.2 eq) at -78 °C, and the resulting mixture was stirred at ambient temperature for 3h. Then, the corresponding aldehyde (10 mmol) was added and stirred for 5 h. The mixture was quenched with saturated aqueous NH4Cl and extracted with ethyl acetate. The combined organic layer was dried over anhydrous Na2SO4 and concentrated under reduced pressure. The residue was purified by flash column chromatography on silica gel to afford the corresponding alkenes. 1a2, 1c, 1d3, 1e, 1f, 1g, 1h4, 1i5, 1j6, 1k7, 1l8,1m9, 1n9, 1o, 1p, 1q, 1u10, 1v11, 1w12, 1x13and 1y13 were prepared according to general procedure A. 1b14were prepared using NaH instead of nBuLi. The data are in accordance with the literatures.

Reference： [1]Bosnidou, Alexandra E.; Muñiz, Kilian [Angewandte Chemie - International Edition, 2019, vol. 58, # 22, p. 7485 - 7489][Angew. Chem., 2019, vol. 131, p. 7564 - 7568,5]
[2]Yang, Hongxuan; Dong, Wenke; Wang, Wencan; Li, Tao; Zhao, Wanxiang [Synthesis, 2020, vol. 52, # 19, p. 2833 - 2840]

50
[ 119-61-9 ]
[ 28322-40-9 ]
[ 19988-49-9 ]

Yield	Reaction Conditions	Operation in experiment
62%	Stage #1: isoamyltriphenylphosphonium bromide With n-butyllithium In tetrahydrofuran; hexane at 0℃; for 0.333333h; Stage #2: benzophenone In tetrahydrofuran; hexane at 0 - 20℃;

Reference： [1]Ludwig, Jacob R.; Simmons, Eric M.; Wisniewski, Steven R.; Chirik, Paul J. [Organic Letters, 2021, vol. 23, # 3]

51
C₂₄H₃₈O₃ [ No CAS ]
[ 28322-40-9 ]
C₂₉H₄₈O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: isoamyltriphenylphosphonium bromide With potassium <i>tert</i>-butylate In dimethyl sulfoxide at 50℃; Inert atmosphere; Stage #2: C₂₄H₃₈O₃ In dimethyl sulfoxide at 30℃; for 2h; Inert atmosphere;	1-2 At room temperature, add 150g of isoamyltriphenylphosphonium bromide into the reaction flask,DMSO 250ml, replace with nitrogen while stirring,Add 40g potassium tert-butoxide,Warm up to 50°C for 2-3hThen the temperature is reduced to about 30°C,Add 50g of the compound of formula I under the protection of nitrogen,Keep the reaction at about 30 degrees, and monitor the reaction by TLC,The reaction is complete in about 2h;After the reaction, 300ml of water was added dropwise to the reaction flask to quench the reaction.At the same time, a large amount of solids are precipitated, filtered,Dry the solid at 50°C;Add 5v acetone to the solid at room temperature and stir to dissolve it.Then the temperature is reduced to about 5°C,Slowly add 1v of water dropwise to it (1h dropwise),Will precipitate a lot of solids,After dripping, continue to stir at about 5°C for 1 hour,Filter and wash with a small amount of ice (acetone/water=5/1, volume ratio),After drying at 50°C, the compound of formula II is obtained.

Reference： [1]Current Patent Assignee: HUNAN KEREY PHARMACEUTICAL - CN112358523, 2021, A Location in patent: Paragraph 0107-0113

52
[ 28322-40-9 ]
[ 6630-33-7 ]
1-bromo-2-[(Z/E)-4-methylpent-1-enyl]benzene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
93%	Stage #1: 3-methylbutyl-triphenylphosphonium bromide With n-butyllithium In tetrahydrofuran; hexane at -78 - 0℃; for 0.5h; Stage #2: ortho-bromobenzaldehyde In tetrahydrofuran; hexane at 20℃; for 1h;	69.1 Step 1: 4,4,5,5-Tetramethyl-2-[2-[(Z/E)-4-methylpent-1-enyl]phenyl]-1,3,2- dioxaborolane Stage 1: To a THF (5 mL) suspension of isopentyl(triphenyl)phosphonium bromide (1.6807 g, 4.066 mmol) at -78 °C was added nBuLi (1.5 mL of 2.5 M in hexanes, 3.750 mmol). The reaction mixture was warmed to 0 °C and stirred for 30 minutes and then treated with 2- bromobenzaldehyde (499.6 mg, 2.700 mmol). The reaction mixture was warmed to ambient temperature and stirred for 1 hour and then cooled to 0 °C and treated with HCl (4 mL of 1 M, 4.000 mmol) and diethyl ether (15 mL). The organic layer was separated, dried with anhydrous sodium sulfate, filtered, and concentrated to minimal volumes (~2-3 mL) and then cooled to 0 °C and stirred for 15 minutes upon which the triphenylphosphine oxide precipitated out. The solid was filtered off and the filtrate was concentrated in vacuo to minimal volumes (~2-3 mL) and the trituration was repeated once again. The ether filtrate was concentrated in vacuo to give 1-bromo-2-[(Z/E)-4-methylpent-1-enyl]benzene (1:1 mixture of isomers, 597.5 mg, 93%).1H NMR (400 MHz, Chloroform-d) δ 7.61 - 7.40 (m, 2H), 7.29 - 7.26 (m, 1H), 7.15 - 7.01 (m, 1H), 6.69 (dd, J = 15.7, 1.6 Hz, 0.4H, isomer 1), 6.48 (dt, J = 11.6, 1.8 Hz, 0.5H, isomer 2), 6.15 (dt, J = 15.6, 7.3 Hz, 0.4H, isomer 1), 5.79 (dt, J = 11.6, 7.4 Hz, 0.5H, isomer 2), 2.19 - 2.02 (m, 2H), 1.83 - 1.63 (m, 1H), 0.93 (dd, J = 27.3, 6.7 Hz, 6H). (some triphenylphosphine oxide impurities in the aromatic region). ESI-MS m/z calc.238.0357, Retention time: 0.9 minutes; LC method D.

Reference： [1]Current Patent Assignee: VERTEX PHARMACEUTICALS (OLD) - WO2022/76627, 2022, A1 Location in patent: Paragraph 00288

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CAS No. :	28322-40-9	MDL No. :	MFCD00031594
Formula :	C₂₃H₂₆BrP	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	GZLGTVRDLCJQTO-UHFFFAOYSA-M
M.W :	413.33	Pubchem ID :	2759379
Synonyms :

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
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Prevention
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P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
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P342	If experiencing respiratory symptoms:
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P353	Rinse skin with water/shower.
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P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
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P378
P380	Evacuate area.
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P391	Collect spillage. Hazardous to the aquatic environment
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P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
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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.
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P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
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P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
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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:
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P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
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P401
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Physical hazards
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H261	In contact with water releases flammable gas
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Health hazards
Code	Phrase
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H310	Fatal in contact with skin
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H370	Causes damage to organs
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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

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[ 28322-40-9 ] Synthesis Path-Downstream 1~52

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