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[ CAS No. 16523-54-9 ] {[proInfo.proName]}

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Chemical Structure| 16523-54-9
Chemical Structure| 16523-54-9
Structure of 16523-54-9 * Storage: {[proInfo.prStorage]}
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Product Details of [ 16523-54-9 ]

CAS No. :16523-54-9 MDL No. :MFCD00014294
Formula : C12H22ClP Boiling Point : -
Linear Structure Formula :- InChI Key :AKJFBIZAEPTXIL-UHFFFAOYSA-N
M.W : 232.73 Pubchem ID :2734135
Synonyms :

Safety of [ 16523-54-9 ]

Signal Word:Danger Class:8
Precautionary Statements:P264-P280-P301+P330+P331-P303+P361+P353-P304+P340+P310-P305+P351+P338+P310-P363-P405-P501 UN#:3265
Hazard Statements:H314 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 16523-54-9 ]

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

  • Upstream synthesis route of [ 16523-54-9 ]
  • Downstream synthetic route of [ 16523-54-9 ]

[ 16523-54-9 ] Synthesis Path-Upstream   1~21

  • 1
  • [ 16523-54-9 ]
  • [ 103099-52-1 ]
Reference: [1] Patent: CN104558029, 2016, B,
  • 2
  • [ 2052-07-5 ]
  • [ 16523-54-9 ]
  • [ 247940-06-3 ]
Reference: [1] Journal of the American Chemical Society, 1999, vol. 121, # 41, p. 9550 - 9561
[2] Organic Letters, 2013, vol. 15, # 24, p. 6186 - 6189
  • 3
  • [ 251320-87-3 ]
  • [ 16523-54-9 ]
  • [ 251320-86-2 ]
Reference: [1] Journal of the American Chemical Society, 1999, vol. 121, # 41, p. 9550 - 9561
  • 4
  • [ 694-80-4 ]
  • [ 33872-80-9 ]
  • [ 16523-54-9 ]
  • [ 251320-86-2 ]
Reference: [1] Advanced Synthesis and Catalysis, 2001, vol. 343, # 8, p. 789 - 794
  • 5
  • [ 19493-31-3 ]
  • [ 16523-54-9 ]
  • [ 251320-86-2 ]
Reference: [1] European Journal of Organic Chemistry, 2012, # 11, p. 2127 - 2131
  • 6
  • [ 694-80-4 ]
  • [ 95-46-5 ]
  • [ 16523-54-9 ]
  • [ 251320-86-2 ]
Reference: [1] Organic Process Research and Development, 2004, vol. 8, # 6, p. 1065 - 1071
  • 7
  • [ 694-80-4 ]
  • [ 698-01-1 ]
  • [ 16523-54-9 ]
  • [ 213697-53-1 ]
Reference: [1] Journal of Organic Chemistry, 2000, vol. 65, # 17, p. 5334 - 5341
[2] Advanced Synthesis and Catalysis, 2006, vol. 348, # 1-2, p. 23 - 39
  • 8
  • [ 694-80-4 ]
  • [ 698-00-0 ]
  • [ 16523-54-9 ]
  • [ 213697-53-1 ]
Reference: [1] Advanced Synthesis and Catalysis, 2001, vol. 343, # 8, p. 789 - 794
  • 9
  • [ 694-80-4 ]
  • [ 16750-63-3 ]
  • [ 16523-54-9 ]
  • [ 255835-82-6 ]
Reference: [1] Journal of Organic Chemistry, 2001, vol. 66, # 11, p. 3820 - 3827
  • 10
  • [ 16523-54-9 ]
  • [ 255835-82-6 ]
Reference: [1] Patent: US6307087, 2001, B1,
[2] Patent: US2004/171833, 2004, A1,
  • 11
  • [ 101-84-8 ]
  • [ 16523-54-9 ]
  • [ 434336-16-0 ]
Reference: [1] Russian Journal of Organic Chemistry, 2001, vol. 37, # 11, p. 1583 - 1586
  • 12
  • [ 21524-34-5 ]
  • [ 16523-54-9 ]
  • [ 583-53-9 ]
  • [ 564483-18-7 ]
YieldReaction ConditionsOperation in experiment
89%
Stage #1: With n-butyllithium In tetrahydrofuran at 0℃; for 1 h; Inert atmosphere
Stage #2: at 0℃; for 1 h; Inert atmosphere
Under the protection of nitrogen, 200 ml of THF and 31g of 2, 4, 6-tri-isopropyl-bromobenzene was added to 1L three-mouth bottle. The temperature was cooled down to 0 °C, and 46 ml of 2.5M n-butyl lithiumwas added dropwise. The reaction was continued for 1 hour after the addition. At 0 °C, 24.6g O-dibromobenzene was added dropwise. The reaction was continued for 1 hour after the addition. At0 °C, 42 ml of 2.5M n-butyl lithiumwas added dropwise to the reaction liquid.After the addition, the reaction was continued for 1 hour. 26.7g of dicyclohexyl phosphine was added dropwise, and the temperature was naturally warmed to react at room temperature for 2 hours. 200 ml saturated ammonium chloride aqueous solution was added dropwsie to the reaction liquid under the ice bath to quench the reaction. After phase separation, the organic phase was precipitated, and methanol was added for crystallization. Byfiltering, 44.5g white product of 2’-dicyclohexyl phosphino-2, 4, 6-tri-isopropyl biphenyl was obtained, with a yield of 89percent.
Reference: [1] Patent: CN105273006, 2016, A, . Location in patent: Paragraph 0069; 0070
  • 13
  • [ 16523-54-9 ]
  • [ 564483-18-7 ]
YieldReaction ConditionsOperation in experiment
90%
Stage #1: at 0℃; for 1 h;
Stage #2: at 20℃; for 2 h;
At 0 °C,42 ml of 2.5M n-butyl lithium was added dropwise to the reaction liquid. After the addition, the reaction was continued for 1 hour.26.7g of dicyclohexyl phosphine was added dropwise, and the temperature was naturally warmed to react at room temperature for 2 hours. 200 ml saturated ammonium chloride aqueous solution was added dropwsie to the reaction liquid under the ice bathto quench the reaction.After phase separation, the organic phase was precipitated,and methanol was added for crystallization. Byfiltering,45g white product of 2’-dicyclohexyl phosphino-2, 4, 6-tri-isopropyl biphenyl was obtained, with a yield of 90percent.
Reference: [1] Patent: CN105273006, 2016, A, . Location in patent: Paragraph 0059
  • 14
  • [ 694-80-4 ]
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  • [ 16523-54-9 ]
  • [ 564483-18-7 ]
Reference: [1] Journal of the American Chemical Society, 2003, vol. 125, # 22, p. 6653 - 6655
[2] Chemistry - A European Journal, 2011, vol. 17, # 39, p. 10828 - 10831
[3] Organic Process Research and Development, 2004, vol. 8, # 6, p. 1065 - 1071
  • 15
  • [ 16523-54-9 ]
  • [ 870703-70-1 ]
  • [ 787618-22-8 ]
Reference: [1] Journal of the American Chemical Society, 2004, vol. 126, # 40, p. 13028 - 13032
  • 16
  • [ 16523-54-9 ]
  • [ 755017-61-9 ]
  • [ 657408-07-6 ]
Reference: [1] Angewandte Chemie - International Edition, 2009, vol. 48, # 32, p. 5841 - 5844
[2] Journal of the American Chemical Society, 2005, vol. 127, # 13, p. 4685 - 4696
  • 17
  • [ 694-80-4 ]
  • [ 151-10-0 ]
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  • [ 657408-07-6 ]
YieldReaction ConditionsOperation in experiment
36%
Stage #1: With n-butyllithium In tetrahydrofuran at 0 - 20℃; for 3.5 h;
Stage #2: at 0℃; for 0.5 h;
To a solution of 1,3-dimethoxybenzene (2 ml, 15.30 mmol) in anhydrous THF (35 ml) at 0° C., nBuLi (6.2 ml, 15.50 mmol) is added to the dropping funnel for 5 min.
The reaction medium is stirred at room temperature for 3.5 h, then 2-bromochlorobenzene (1.6 ml, 13.70 mmol) is added by syringe, dropwise, at 0° C., for 30 min.
After 15 min of stirring, the reaction medium is cooled to -78° C. and nBuLi (6.20 ml, 15.50 mmol) is added to the dropping funnel dropwise for 5 min.
After 30 min, chlorodicyclohexylphosphine (3.03 ml, 13.70 mmol) is added.
The reaction medium is maintained at -78° C. for 1 h, under rapid stirring (mechanical stirring).
After returning to room temperature, the precipitate obtained is filtered on a fritted disc containing silica topped with a layer of cellulose acetate, with 600 ml ethyl acetate.
The solvents are evaporated with a rotary evaporator, and the orange oil obtained is recrystallized in acetone to obtain S-Phos ligand in the form of white crystals with a yield of 36percent (1.22 g, 2.97 mmol).
MP: 163-165° C. (Lit.
MP 162.0-162.5° C.); TLC: (AcOEt/cyclohexane 10/90). Rf=0.65; 1H-NMR (CDCl3): δ=0.99-1.26 (m, 10H, H(Cy)), 1.60-1.77 (m, 12H, H(Cy)), 3.67 (s, 6H, Me), 6.58 (d, 2H, J=8.2 Hz, H3' and H5'), 7.15-7.18 (m, 1H, H(Ar)), 7.18-7.42 (m, 3H, H(Ar)), 7.57 (d, 1H, J=7.4 Hz, H(Ar)) ppm; 13C-NMR (CDCl3): δ=26.5, 27.3, 27.4, 27.6, 29.0, 29.1, 29.8, 30.1, 33.8, 34.0 (C(Cy)), 55.3 (Cb), 103.1 (Ca), 126.2, 128.2, 128.8 (C3', C4', C5'), 130.9, 131.00, 132.4, 135.8 (C3, C4, C5, C6), 135.8, 136.1, 142.7, 143.1, 157.4 (C2', C6') ppm; IR (KBr): υ=3000, 2923, 2851, 1588, 1471, 1442, 1428, 1108 cm-1.
Reference: [1] Patent: US2011/184059, 2011, A1, . Location in patent: Page/Page column 9
  • 18
  • [ 1380028-15-8 ]
  • [ 16523-54-9 ]
  • [ 657408-07-6 ]
Reference: [1] European Journal of Organic Chemistry, 2012, # 11, p. 2127 - 2131
  • 19
  • [ 13732-86-0 ]
  • [ 16523-54-9 ]
  • [ 657408-07-6 ]
Reference: [1] Journal of the American Chemical Society, 2014, vol. 136, # 24, p. 8568 - 8576
  • 20
  • [ 1070663-76-1 ]
  • [ 16523-54-9 ]
  • [ 1070663-78-3 ]
YieldReaction ConditionsOperation in experiment
88%
Stage #1: With n-butyllithium In tetrahydrofuran; hexane at -78℃; Inert atmosphere
Stage #2: at -78 - 20℃; Inert atmosphere
EXAMPLE TWO: General Procedure for the Synthesis of Compounds 1 through 5; An oven-dried 25 mL round bottom flask, which was equipped with a magnetic stir bar and charged with 2-iodo-2',4',6'-triisopropyl-3,6-dimethoxybiphenyl (1 g, 2.15 mmol), was evacuated and backfilled with argon (this process was repeated a total of 3 times).THF (10 mL) was added via syringe and the reaction was cooled to -78 0C and n-BuLi (2.5 M in Hexane, 940 μL, 2.36 mmol) was added dropwise over a 10 min period. The solution was stirred for 30 min and then the ClPR2 (2.26 mmol) was added dropwise over a 10 min period. The reaction was stirred for 1 h at -78 0C and then warmed slowly to room temperature and stirred for an additional 1.5 h. The solution was filtered through a plug of Celite layered on a plug of silica (eluting with EtOAc) and then concentrated on a rotary evaporator to give a white solid. The crude material was recrystallized from acetone <n="117"/>(ligands 2 through 5 were recrystallized from MeOH) to yield white crystals of the desired product.
Reference: [1] Journal of the American Chemical Society, 2008, vol. 130, # 41, p. 13552 - 13554
[2] Patent: WO2009/76622, 2009, A2, . Location in patent: Page/Page column 115-116
  • 21
  • [ 1160556-63-7 ]
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  • [ 1160556-64-8 ]
Reference: [1] Journal of the American Chemical Society, 2009, vol. 131, p. 7532 - 7533
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