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[ CAS No. 6737-42-4 ] {[proInfo.proName]}

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Chemical Structure| 6737-42-4
Chemical Structure| 6737-42-4
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Boivin, Leo ; Schlachter, Adrien ; Fortin, Daniel , et al. DOI: PubMed ID:

Abstract: The prediction of the metal cluster within a coordination polymer or complex, as well as the dimensionality of the resulting polymer or complex (i.e., 0D, 1D, 2D, or 3D), is often challenging. This is the case for Ph2P(CH2)mPPh2 ligands (1 ≤ m ≤ 8) and CuX salts, particularly for X = I. This work endeavors a systematic statistical anal. combining studies in the literature and new data, mapping the nature of the resulting CuI aggregates with eight different diphoshphines in 2:1, 3:2, 1:1, 2:3, and 1:2 CuI:Ph2P(CH2)mPPh2 molar ratios as a function of m, which lead to either pure products or mixtures Several trends are made relating stoichiometry and chain length to the CuI cluster formed (i.e., globular vs. quasi-planar). Four new X-ray structures were determined: [Cu3I2(L1)3]I, Cu3I3(L2)2, Cu2I2(L6)2, and Cu4I4(L8)2, where m is, resp., 1, 2, 6, and 8, in which the CuxIy central aggregates adopt triangular bipyramid, diamond, rhomboid, and cubane shaped motifs, resp. Photophys. measurements assisted the establishment of trends considering the paucity of the crystallog. structures. During this study, it was also found that the 0D-complex Cu2I2(Ph2P(CH2)5PPh2)2 exhibits thermally activated delayed fluorescence.

Keywords: copper(I) iodide coordination polymers ; photophysics ; TADF

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Product Details of [ 6737-42-4 ]

CAS No. :6737-42-4 MDL No. :MFCD00003050
Formula : C27H26P2 Boiling Point : -
Linear Structure Formula :(C6H5)4P2CH2CH2CH2 InChI Key :LVEYOSJUKRVCCF-UHFFFAOYSA-N
M.W : 412.44 Pubchem ID :81219
Synonyms :

Calculated chemistry of [ 6737-42-4 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 29
Num. arom. heavy atoms : 24
Fraction Csp3 : 0.11
Num. rotatable bonds : 8
Num. H-bond acceptors : 0.0
Num. H-bond donors : 0.0
Molar Refractivity : 132.56
TPSA : 27.18 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : Yes
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : Yes
Log Kp (skin permeation) : -4.39 cm/s

Lipophilicity

Log Po/w (iLOGP) : 4.41
Log Po/w (XLOGP3) : 6.23
Log Po/w (WLOGP) : 5.64
Log Po/w (MLOGP) : 6.89
Log Po/w (SILICOS-IT) : 8.54
Consensus Log Po/w : 6.34

Druglikeness

Lipinski : 1.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -6.41
Solubility : 0.000162 mg/ml ; 0.000000392 mol/l
Class : Poorly soluble
Log S (Ali) : -6.59
Solubility : 0.000107 mg/ml ; 0.000000259 mol/l
Class : Poorly soluble
Log S (SILICOS-IT) : -11.29
Solubility : 0.0000000021 mg/ml ; 0.0 mol/l
Class : Insoluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 3.0
Synthetic accessibility : 5.58

Safety of [ 6737-42-4 ]

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 [ 6737-42-4 ]

* 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 [ 6737-42-4 ]
  • Downstream synthetic route of [ 6737-42-4 ]

[ 6737-42-4 ] Synthesis Path-Upstream   1~16

  • 1
  • [ 6737-42-4 ]
  • [ 147283-85-0 ]
  • [ 52787-14-1 ]
Reference: [1] Patent: US5521179, 1996, A,
  • 2
  • [ 16524-41-7 ]
  • [ 6737-42-4 ]
YieldReaction ConditionsOperation in experiment
80% With indium(III) bromide; 1,1,3,3-Tetramethyldisiloxane In toluene at 100℃; for 22 h; Inert atmosphere; Sealed tube General procedure: In a sealed tube containing a solution of the phosphine oxide derivative (5 mmol) in anhydrous toluene (1M) was added InBr3 (1 mol percent, 0.05 mmol) and the TMDS (1.5 equiv., 7.5 mmol). The reactionnal mixture was stirred at 100 °C during 7 to 40 h depending on the substrate (the reaction was monitored by 31P NMR). After complete consumption and evaporation of toluene the phosphine was purified by flash chromatography on silica gel with pure cyclohexane) to afford the desired phosphine.
Reference: [1] Organometallics, 2014, vol. 33, # 21, p. 6171 - 6178
[2] Synlett, 2007, # 10, p. 1545 - 1548
[3] Journal of the American Chemical Society, 2012, vol. 134, # 44, p. 18325 - 18329
[4] Tetrahedron, 2012, vol. 68, # 15, p. 3151 - 3155
[5] Advanced Synthesis and Catalysis, 2016, vol. 358, # 1, p. 26 - 29
  • 3
  • [ 7439-93-2 ]
  • [ 142-28-9 ]
  • [ 603-35-0 ]
  • [ 1309391-39-6 ]
  • [ 6737-42-4 ]
YieldReaction ConditionsOperation in experiment
6.36%
Stage #1: at 50℃;
Stage #2: at 0 - 80℃;
Stage #3: With oxygen In methanol; water
General Procedure: A 2 l four-necked flask equipped with an effective condenser, a stirrer and a dropping funnel was filled with 500 ml of dry THF which was then deoxygenated for 1 h by transmitting of dry nitrogen. Then 100 g (0.382 mol) of triphenylphosphine was added, and the mixture was stirred till a clear solution was obtained, wherein 6 g (0.856 mol) of freshly prepared ultra-fine lithium flushed with THF was added a little at a time in high purity argon current. The addition rate of the lithium was limited by keeping an exothermic reaction temperature below 50 °C. When the loading of the lithium was completed, the resultant crimson solution was cooled to 0 °C, and a solution of 50 g (0.442 mol) of 1,3-dichloropropane or 62.3 g (0.442 mol) of 1,5-dichloropentane in 50 ml of THF was added by drops to the reaction mass with the temperature kept at 0 °C. When dripping was over, the color of the reaction mass turned light-brown. The mixture was boiled at the flask temperature of 80 °C for 3 h. After the mixture got self-cooled to room temperature, 750 ml of deoxygenated methanol was added to it. The mass was cooled to 0 °C, and 125 ml of oxygen-free water was rapidly added by drops into a vigorously stirred mass. The suspension of the deposited diphosphines 1 or 2 was settled at 0 °C for a short time possible, a solution was decanted from them. The residuum was filtered under nitrogen, rinsed with 5 x 25 ml of cold diethyl ether and dried in vacuum for 20 h. Obtained: 21.54 g (yield 35percent as compared with Ph3P) 1,3-bis(diphenylphosphine)propane (1) or 29.4 g (yield 35percent as compared with Ph3P) 1,5-bis(diphenylphosphine)pentane (2) in the form of white amorphous powders with melting temperatures 61-63 and 41-44 °C respectively that agreed with the literature data [24]. 1H and 31P NMR spectra corresponded to a structure of the compounds and are given in Table 3. When compound 1 was synthesized using not deoxygenated methanol and water, a by process of formation of 1,3-bis(diphenylphosphine)propanemonoxide (3) was observed. In this case a mixture of compounds 1 and 3 was a caramel-like, non-crystallizing mass which was subsequently cut by way of fractional recrystallization from the benzene/methanol mixture. Obtained: 8.4 g of compound 1 (yield 13.6percent) and 5.2 g of compound 3 (yield 6.36percent as compared with Ph3P) with melting temperatures 121-124 °C.
Reference: [1] Journal of Organometallic Chemistry, 2011, vol. 696, # 10, p. 2238 - 2251
  • 4
  • [ 109-64-8 ]
  • [ 829-85-6 ]
  • [ 6737-42-4 ]
Reference: [1] Tetrahedron Letters, 2003, vol. 44, # 46, p. 8373 - 7377
[2] Phosphorus, Sulfur and Silicon and the Related Elements, 2004, vol. 179, # 2, p. 277 - 283
[3] Phosphorus, Sulfur and Silicon and the Related Elements, 1993, vol. 81, # 1-4, p. 155 - 164
  • 5
  • [ 7439-93-2 ]
  • [ 142-28-9 ]
  • [ 603-35-0 ]
  • [ 6737-42-4 ]
YieldReaction ConditionsOperation in experiment
35%
Stage #1: at 50℃; Inert atmosphere
Stage #2: at 0 - 80℃; Inert atmosphere
General Procedure: A 2 l four-necked flask equipped with an effective condenser, a stirrer and a dropping funnel was filled with 500 ml of dry THF which was then deoxygenated for 1 h by transmitting of dry nitrogen. Then 100 g (0.382 mol) of triphenylphosphine was added, and the mixture was stirred till a clear solution was obtained, wherein 6 g (0.856 mol) of freshly prepared ultra-fine lithium flushed with THF was added a little at a time in high purity argon current. The addition rate of the lithium was limited by keeping an exothermic reaction temperature below 50 °C. When the loading of the lithium was completed, the resultant crimson solution was cooled to 0 °C, and a solution of 50 g (0.442 mol) of 1,3-dichloropropane or 62.3 g (0.442 mol) of 1,5-dichloropentane in 50 ml of THF was added by drops to the reaction mass with the temperature kept at 0 °C. When dripping was over, the color of the reaction mass turned light-brown. The mixture was boiled at the flask temperature of 80 °C for 3 h. After the mixture got self-cooled to room temperature, 750 ml of deoxygenated methanol was added to it. The mass was cooled to 0 °C, and 125 ml of oxygen-free water was rapidly added by drops into a vigorously stirred mass. The suspension of the deposited diphosphines 1 or 2 was settled at 0 °C for a short time possible, a solution was decanted from them. The residuum was filtered under nitrogen, rinsed with 5 x 25 ml of cold diethyl ether and dried in vacuum for 20 h. Obtained: 21.54 g (yield 35percent as compared with Ph3P) 1,3-bis(diphenylphosphine)propane (1) or 29.4 g (yield 35percent as compared with Ph3P) 1,5-bis(diphenylphosphine)pentane (2) in the form of white amorphous powders with melting temperatures 61-63 and 41-44 °C respectively that agreed with the literature data [24]. 1H and 31P NMR spectra corresponded to a structure of the compounds and are given in Table 3. When compound 1 was synthesized using not deoxygenated methanol and water, a by process of formation of 1,3-bis(diphenylphosphine)propanemonoxide (3) was observed. In this case a mixture of compounds 1 and 3 was a caramel-like, non-crystallizing mass which was subsequently cut by way of fractional recrystallization from the benzene/methanol mixture. Obtained: 8.4 g of compound 1 (yield 13.6percent) and 5.2 g of compound 3 (yield 6.36percent as compared with Ph3P) with melting temperatures 121-124 °C.
Reference: [1] Journal of Organometallic Chemistry, 2011, vol. 696, # 10, p. 2238 - 2251
  • 6
  • [ 109-70-6 ]
  • [ 6737-42-4 ]
Reference: [1] Patent: WO2006/84878, 2006, A1, . Location in patent: Page/Page column 19-20
  • 7
  • [ 109-64-8 ]
  • [ 4559-70-0 ]
  • [ 6737-42-4 ]
Reference: [1] Journal of the American Chemical Society, 2012, vol. 134, # 23, p. 9727 - 9732
  • 8
  • [ 67-56-1 ]
  • [ 100809-49-2 ]
  • [ 121-43-7 ]
  • [ 6737-42-4 ]
Reference: [1] Tetrahedron, 2009, vol. 65, # 32, p. 6410 - 6415
  • 9
  • [ 142-28-9 ]
  • [ 603-35-0 ]
  • [ 6737-42-4 ]
Reference: [1] Journal of the Chemical Society - Dalton Transactions, 1998, # 14, p. 2379 - 2382
  • 10
  • [ 1079-66-9 ]
  • [ 6737-42-4 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1988, p. 1787 - 1790
  • 11
  • [ 100809-49-2 ]
  • [ 64-17-5 ]
  • [ 150-46-9 ]
  • [ 6737-42-4 ]
Reference: [1] Tetrahedron, 2009, vol. 65, # 32, p. 6410 - 6415
  • 12
  • [ 100-58-3 ]
  • [ 6737-42-4 ]
Reference: [1] Organometallics, 2014, vol. 33, # 21, p. 6171 - 6178
  • 13
  • [ 142-28-9 ]
  • [ 65567-06-8 ]
  • [ 6737-42-4 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1988, p. 1787 - 1790
[2] Bulletin of the Chemical Society of Japan, 1989, vol. 62, # 11, p. 3508 - 3512
  • 14
  • [ 142-28-9 ]
  • [ 829-85-6 ]
  • [ 6737-42-4 ]
Reference: [1] J. Gen. Chem. USSR (Engl. Transl.), 1985, vol. 55, # 1, p. 8 - 22[2] Zhurnal Obshchei Khimii, 1985, vol. 55, # 1, p. 11 - 26
  • 15
  • [ 463-49-0 ]
  • [ 829-85-6 ]
  • [ 6737-42-4 ]
  • [ 15383-58-1 ]
  • [ 4559-70-0 ]
  • [ 2741-38-0 ]
Reference: [1] Journal of Organometallic Chemistry, 1991, vol. 409, # 1-2, p. 163 - 170
  • 16
  • [ 7651-83-4 ]
  • [ 6737-42-4 ]
  • [ 407623-83-0 ]
Reference: [1] Patent: US2003/186969, 2003, A1,
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