Home Cart 0 Sign in  

[ CAS No. 51044-13-4 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
Chemical Structure| 51044-13-4
Chemical Structure| 51044-13-4
Structure of 51044-13-4 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Quality Control of [ 51044-13-4 ]

Related Doc. of [ 51044-13-4 ]

Alternatived Products of [ 51044-13-4 ]

Product Details of [ 51044-13-4 ]

CAS No. :51044-13-4 MDL No. :MFCD00051922
Formula : C25H21Br2P Boiling Point : -
Linear Structure Formula :- InChI Key :FQJYKXVQABPCRA-UHFFFAOYSA-M
M.W : 512.22 Pubchem ID :2724858
Synonyms :

Safety of [ 51044-13-4 ]

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:

Application In Synthesis of [ 51044-13-4 ]

* 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.

  • Upstream synthesis route of [ 51044-13-4 ]
  • Downstream synthetic route of [ 51044-13-4 ]

[ 51044-13-4 ] Synthesis Path-Upstream   1~3

  • 1
  • [ 589-15-1 ]
  • [ 603-35-0 ]
  • [ 51044-13-4 ]
YieldReaction ConditionsOperation in experiment
100% for 4 h; Heating / reflux 4-Bromobenzyl bromide (50 g, 200 mmol, 1.0 equiv), triphenylphosphine (57 g, 220mmol, 1.1 equiv), in CHC13 (400 mL, 0.5 M) was heated under reflux 4 h. The solution was cooled to room temperature and the phosphonium was crunched with Et20 (1.5 L). The crude product was diluted with CH2C12 (300 mL) and was crunched with Et20 (1.5 L) was filtered under Buchner and washed with Et20 (500 mL) to afford target compound (44) as a white solid (123 g, quant. yield).
99% at 20℃; for 12 h; Multi function cap round bottom 1-bromo-4-(bromomethyl) Benzene to 500 ml (14.0 g, 0.056 mol), Triphenylphosphine (16.162 g, 0.062 mol) has added. Herein, as a solvent at room temperature of 58 ml Acetone adaptation stirring time doesn't have any error frames, 12. 28.4 g is obtained complete after title compound. (99.0percent yield).
99% at 20℃; for 12 h; Inert atmosphere In a two-necked round bottom fask a mixture of 1-bromo-4-(bromomethyl)benzene (10g, 40mmol), triphenylphosphine (11.5g, 44mmol,1.1 eq) inacetone (42mL) was stirred atroom temperature under N2 atmospherefor 12h. The reactionmixturewasthen ltered andthewhitesolidswerecollectedwashedwithacetonebeforedrying invacuo(20.3g,99percent).
98% at 20℃; for 23 h; (i)
Synthesis of 4-bromobenzyltriphenylphosphonium bromide
25.2 g (101 mmol) of 4-bromobenzylbromide and 100 mL of acetone were put into a 200 mL conical flask, and then 29.1 g (111 mmol) of triphenylphosphine was added thereto.
Thereafter, this mixture was stirred at room temperature for 23 hours to be reacted.
After the reaction, a precipitate in the reaction mixture was collected by suction filtration.
Then, 50.5 g of objective 4-bromobenzyltriphenylphosphonium bromide was obtained as a white powdered solid in a yield of 98percent.
Synthetic scheme of 4-bromobenzyltriphenylphosphonium bromide is illustrated below (synthetic scheme a-1).
97.6% at 20℃; for 23 h; [Step 1; Synthesis of 4-bromobenzyl triphenylphosphonium bromide]
First, 25.2 g (101 mmol) of 4-bromobenzyl bromide and 100 mL of acetone were placed in a 200 mL conical flask, and 29.1 g (111 mmol) of triphenylphosphine was added thereto.
This reaction mixture was stirred at room temperature for 23 hours.
After the completion of the reaction, the precipitate in the reaction mixture was collected by suction filtration.
50.5 g of a white powdered solid, 4-bromobenzyl triphenylphosphonium bromide, which was the target substance, was obtained in a yield of 97.6percent.
A synthetic scheme (a-1) of 4-bromobenzyl triphenylphosphonium bromide is shown below.
97.6% at 20℃; for 23 h; First, 25.2 g (101 mmol) of 4-bromobenzyl bromide and 100 mL of acetone were put into a 200 mL conical flask, and 29.1 g (111 mmol) of triphenylphosphine was added thereto. The mixture was stirred for 23 hours at room temperature. After the reaction, a precipitate in the reaction mixture was collected by suction filtration to give 50.5 g of a white powdered solid of (4-bromobenzyl)triphenylphosphoniumbromide (yield: 97.6percent).
96% at 20℃; for 24 h; First, 25.36 g (101.5 mmol) of 4-bromobenzylbromide and 100 mL of acetone were put in a 100 mL conical flask, and 29.28 g (111.6 mmol) of triphenylphosphine was added thereto. The mixture was stirred for 24 hours at room temperature. After the reaction, a precipitate in the reaction mixture was collected by suction filtration, and 50 g of a white powdered solid of 4-bromobenzyltriphenylphosphoniumbromide was obtained in a yield of 96percent.
96% at 20℃; for 24 h; A 200 mL conical flask was charged with 25.36 g (101.5 mmol) of 4-bromobenzyl bromide and 100 mL of acetone. 29.28 g (111.6 mmol) of triphenylphosphine was added thereto to be stirred for about 24 hours at room temperature. After the reaction, precipitate in the reaction mixture was collected by suction filtration to obtain 50 g of white powder of 4-bromobenzyl triphenylphosphonium bromide in a yield of 96percent. A synthesis scheme of 4-bromobenzyl triphenylphosphonium bromide is shown below.
95% for 12 h; Reflux A solution of 4-bromo benzyl bromide (10.0 g, 40.0 mmol) and PPh3 (10.5 g, 40.0 mmol) in toluene (100 mL) was heated to reflux for 12 hours. After cooled to room temperature, the mixture was filtrated and the filter cake was washed with toluene (200 mL), dried over high vacuum to give compound N1 19.5 g, yield: 95percent) as a white powder which was used to next step directly.
94% for 6 h; Reflux General procedure: Triphenylphosphine (5 mmol) was added to a solution of 4-substituted-benzyl halide (5 mmol) in toluene (50 mL). The mixture was heated to reflux for 6 h and then cooled to room temperature. The precipitate was collected, recrystallized from ethanol to give the products.
93% for 10 h; Inert atmosphere; Reflux General procedure: To a solution of benzylbromide (33 mmol) in toluene (20 mL) was added a solution of triphenylphosphine (36.3 mmol) in toluene (25 mL). After being heated at reflux for 5 h, the reaction mixture was cooled at room temperature and a first crop of product was collected by filtration. The filtrate was then refluxed for additional 5 h and a second crop of product precipitated (10-20percent). The collected crops were crystallized from ethanol to give pure phosphonium bromide in high yield.
93% Reflux 4-Bromobenzyl bromide (7.07 g, 28.30 mmol) and triphenylphosphine (7.42 g, 28.30 mmol) weresuspended in 50 mL toluene and the solution was refluxed overnight. During reaction, a whiteprecipitate formed. It was filtered off, washed several times with ether and dried under vacuum(13.42 g, 93percent yield).
89% at 120℃; for 17 h; Inert atmosphere Intermediate 2 (4^Bromobenzyl)(triphenyl)phosphonium bromide To a stirred solution of 1 -bromo-4-(bromomethyl)benzene (8g, 32mmol) in toluene (160 ml) was added triphenylphosphine (8.4g, 32mmol). The reaction was stirred at 120°C under an atmoshpere of nitrogen for 17 hours after which time a white precipitate had formed. The reaction was then cooled to room temperature and the solid was collected by filtration, washing with a minimum amount of cold toluene to give (4- bromobenzyl)(triphenyl)phosphonium bromide as a white solid (15.4 g, 89 percent) lH NMR (400 MHz, DMSO-c/6) δ 7.85 - 8.01 (m, 2 H), 7.57 - 7.84 (m, 8 H), 7.33 - 7.55 (m, 1 H), 6.79 - 7.02 (m, 1 H), 5.04 - 5.28 (m, 2 H) MS ES+ 433, 435

Reference: [1] Patent: WO2005/97812, 2005, A1, . Location in patent: Page/Page column 64
[2] ACS Medicinal Chemistry Letters, 2015, vol. 6, # 8, p. 902 - 907
[3] Patent: KR2015/103967, 2015, A, . Location in patent: Paragraph 0100
[4] Dyes and Pigments, 2019, vol. 162, p. 959 - 966
[5] Patent: US2008/81934, 2008, A1, . Location in patent: Page/Page column 34
[6] Patent: US7732619, 2010, B2, . Location in patent: Page/Page column 80
[7] Patent: US7758972, 2010, B2, . Location in patent: Page/Page column 77
[8] Patent: US2007/80630, 2007, A1, . Location in patent: Page/Page column 62; 64; 66
[9] Patent: US2007/100180, 2007, A1, . Location in patent: Page/Page column 15
[10] Macromolecules, 2002, vol. 35, # 13, p. 4849 - 4851
[11] European Journal of Organic Chemistry, 2007, # 12, p. 1891 - 1904
[12] Journal of the American Chemical Society, 2012, vol. 134, # 40, p. 16671 - 16692
[13] Patent: WO2015/14993, 2015, A2, . Location in patent: Page/Page column 40
[14] European Journal of Medicinal Chemistry, 2011, vol. 46, # 7, p. 2908 - 2916
[15] Tetrahedron, 2012, vol. 68, # 20, p. 3899 - 3907
[16] Molecules, 2017, vol. 22, # 12,
[17] Journal of Fluorine Chemistry, 1996, vol. 79, # 2, p. 173 - 178
[18] Patent: WO2013/27001, 2013, A1, . Location in patent: Page/Page column 34
[19] Journal of Materials Chemistry, 2002, vol. 12, # 12, p. 3431 - 3437
[20] Journal of Pharmaceutical Sciences, 1975, vol. 64, # 7, p. 1170 - 1173
[21] Tetrahedron, 1986, vol. 42, # 15, p. 4161 - 4168
[22] Journal of Chemical Research, Miniprint, 1986, # 12, p. 3514 - 3530
[23] Journal of Medicinal Chemistry, 1994, vol. 37, # 1, p. 151 - 157
[24] Tetrahedron, 2003, vol. 59, # 7, p. 1021 - 1032
[25] New Journal of Chemistry, 2005, vol. 29, # 3, p. 479 - 484
[26] Chemistry - A European Journal, 2003, vol. 9, # 20, p. 5074 - 5084
[27] Australian Journal of Chemistry, 2006, vol. 59, # 2, p. 118 - 122
[28] Patent: US2007/78267, 2007, A1, . Location in patent: Page/Page column 18
[29] Patent: WO2008/23336, 2008, A2, . Location in patent: Page/Page column 53
[30] Tetrahedron Letters, 2013, vol. 54, # 15, p. 1991 - 1993
[31] Patent: US2013/338120, 2013, A1, . Location in patent: Paragraph 0196
[32] Chemical Communications, 2014, vol. 50, # 81, p. 12076 - 12079
[33] New Journal of Chemistry, 2015, vol. 39, # 9, p. 7472 - 7480
[34] Journal of Medicinal Chemistry, 2015, vol. 58, # 16, p. 6494 - 6506
[35] Journal of Fluorine Chemistry, 2015, vol. 179, p. 116 - 120
  • 2
  • [ 106-38-7 ]
  • [ 603-35-0 ]
  • [ 51044-13-4 ]
Reference: [1] Organic Letters, 2004, vol. 6, # 17, p. 2933 - 2936
  • 3
  • [ 106-38-7 ]
  • [ 51044-13-4 ]
Reference: [1] Tetrahedron, 1986, vol. 42, # 15, p. 4161 - 4168
[2] Journal of Pharmaceutical Sciences, 1975, vol. 64, # 7, p. 1170 - 1173
Same Skeleton Products
Historical Records