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[ CAS No. 624-38-4 ] {[proInfo.proName]}

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Chemical Structure| 624-38-4
Chemical Structure| 624-38-4
Structure of 624-38-4 * Storage: {[proInfo.prStorage]}
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Product Details of [ 624-38-4 ]

CAS No. :624-38-4 MDL No. :MFCD00001054
Formula : C6H4I2 Boiling Point : -
Linear Structure Formula :- InChI Key :LFMWZTSOMGDDJU-UHFFFAOYSA-N
M.W :329.90 Pubchem ID :12208
Synonyms :

Calculated chemistry of [ 624-38-4 ]

Physicochemical Properties

Num. heavy atoms : 8
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 0.0
Num. H-bond donors : 0.0
Molar Refractivity : 51.88
TPSA : 0.0 Ų

Pharmacokinetics

GI absorption : Low
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.39 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.32
Log Po/w (XLOGP3) : 4.11
Log Po/w (WLOGP) : 2.9
Log Po/w (MLOGP) : 4.1
Log Po/w (SILICOS-IT) : 3.83
Consensus Log Po/w : 3.45

Druglikeness

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

Water Solubility

Log S (ESOL) : -5.03
Solubility : 0.00308 mg/ml ; 0.00000934 mol/l
Class : Moderately soluble
Log S (Ali) : -3.82
Solubility : 0.0504 mg/ml ; 0.000153 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.27
Solubility : 0.0177 mg/ml ; 0.0000537 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.31

Safety of [ 624-38-4 ]

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 [ 624-38-4 ]

* 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 [ 624-38-4 ]
  • Downstream synthetic route of [ 624-38-4 ]

[ 624-38-4 ] Synthesis Path-Upstream   1~26

  • 1
  • [ 75-77-4 ]
  • [ 624-38-4 ]
  • [ 13183-70-5 ]
  • [ 17881-56-0 ]
Reference: [1] Organometallics, 2017, vol. 36, # 20, p. 3981 - 3986
  • 2
  • [ 591-50-4 ]
  • [ 513-36-0 ]
  • [ 624-38-4 ]
  • [ 35779-04-5 ]
Reference: [1] Bulletin de la Societe Chimique de France, 1906, vol. <3> 35, p. 826
  • 3
  • [ 1112-55-6 ]
  • [ 624-38-4 ]
  • [ 105-06-6 ]
  • [ 2351-50-0 ]
YieldReaction ConditionsOperation in experiment
80% With potassium fluoride; Pd (1.09 wt%)/TiO2 In N,N-dimethyl-formamide at 130℃; for 1.5 h; Inert atmosphere General procedure: A mixture of diiodobenzene (1i-j) (0.25mmol), vinysilane 2c (0.15mmol), potassium fluoride (1.2mmol), and supported palladium NPs catalyst (Pd/substrate ratio 1molpercent) was suspended in DMF (1ml). Then, the flask was evacuated under vacuum and refilled with argon. The evacuation/refilling cycle was repeated three times (pressure 2bar). The reaction mixture was stirred at 130°C, and the reaction was monitored by GC and GC–MS, for 3h. During this time, all the initial compounds 3i′-j′ formed arising from the replacement of a single iodide are reacted to obtain the maximum yield of products 3i-j.
Reference: [1] Journal of Catalysis, 2013, vol. 302, p. 49 - 57
  • 4
  • [ 624-38-4 ]
  • [ 1826-67-1 ]
  • [ 105-06-6 ]
  • [ 2351-50-0 ]
Reference: [1] Organic Letters, 2003, vol. 5, # 26, p. 4963 - 4966
  • 5
  • [ 624-38-4 ]
  • [ 754-05-2 ]
  • [ 16029-98-4 ]
  • [ 107-46-0 ]
  • [ 2351-50-0 ]
  • [ 106-99-0 ]
Reference: [1] Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation), 1984, vol. 33, # 10, p. 2139 - 2140[2] Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1984, # 10, p. 2342 - 2343
  • 6
  • [ 7486-35-3 ]
  • [ 88016-29-9 ]
  • [ 624-38-4 ]
  • [ 2351-50-0 ]
Reference: [1] Tetrahedron Letters, 1996, vol. 37, # 21, p. 3723 - 3726
  • 7
  • [ 624-38-4 ]
  • [ 171364-83-3 ]
  • [ 29170-08-9 ]
  • [ 3282-11-9 ]
Reference: [1] Journal of Organic Chemistry, 2005, vol. 70, # 9, p. 3730 - 3733
  • 8
  • [ 624-38-4 ]
  • [ 122-39-4 ]
  • [ 38257-52-2 ]
YieldReaction ConditionsOperation in experiment
85% With copper(l) iodide; 1,7-phenanthroline; potassium hydroxide In toluene at 120℃; for 12 h; Inert atmosphere To a mixture of 1,4-diiodobenzene (396 mg, 1.2 mmol), diphenylamine(169 mg, 1 mmol), CuI (19 mg, 0.1 mmol), phenanthroline(28.2 mg, 0.12 mmol) and potassium hydroxide (224 mg,4 mol), dry toluene (20 mL) was added under the protection ofnitrogen. Then mixture was heated to 120 C and kept at this temperaturefor about 12 h. After then, the reaction was quenched bythe addition of water (30 ml). The reaction mixture was extractedwith CH2Cl2 (30 ml) for three times and the combined organic extractswere dried over anhydrous magnesium sulfate for overnight.Then the organic solvent was evaporated under reduced pressure.The residue was purified by column chromatography on silica gelusing petroleum ether as eluent. N-(4-iodophenyl)-N-pheny-benzenamine(6) was obtained as a white powder (315.4 mg, 85percent).Mp > 300 C; 1H NMR (300 MHz, CDCl3): 7.58 (d, 2H), 7.28 (m,4H), 7.08 (m, 6H), 6.83 (d, 2H). MS (ESI): m/z, calculated forC18H14IN: 371.21, found: 372.02 [M + H]+.
Reference: [1] Tetrahedron, 2014, vol. 70, # 10, p. 1903 - 1909
[2] Journal of Molecular Structure, 2014, vol. 1056-1057, # 1, p. 339 - 346
[3] Journal of Polymer Science, Part A: Polymer Chemistry, 2011, vol. 49, # 2, p. 392 - 402
[4] Journal of the American Chemical Society, 2006, vol. 128, # 11, p. 3789 - 3799
[5] Angewandte Chemie - International Edition, 2013, vol. 52, # 48, p. 12696 - 12700[6] Angew. Chem., 2013, vol. 125, # 48, p. 12928 - 12932
[7] Patent: US2018/212158, 2018, A1, . Location in patent: Paragraph 0546
  • 9
  • [ 624-38-4 ]
  • [ 38257-52-2 ]
YieldReaction ConditionsOperation in experiment
66% With potassium fluoride In dimethyl sulfoxide at 130℃; Intermediate 15-1 (10.3 g, 0.035 mol), 1,4-diiodobenzene (11.3 g, 0.035 mol),Catalyst Copper (II) (0.40 g, 0.0029 mol),Potassium fluoride (2.05 g, 0.029 mol)DMSO 400mlAnd the reaction was carried out at 130 ° C.After cooling the reaction mixture, the crude product was added by the amount of the reaction solvent, and after extraction, column purification (n-Hexane: methylene chloride) was conducted to obtain 8.6 g (yield 66percent) of intermediate 15-2.
Reference: [1] Patent: KR101527181, 2015, B1, . Location in patent: Paragraph 0213; 0214; 0215
  • 10
  • [ 624-38-4 ]
  • [ 90-30-2 ]
  • [ 38257-52-2 ]
Reference: [1] Journal of the American Chemical Society, 1987, vol. 109, # 5, p. 1496 - 1502
  • 11
  • [ 624-38-4 ]
  • [ 122-39-4 ]
  • [ 14118-16-2 ]
  • [ 38257-52-2 ]
Reference: [1] Chemistry - A European Journal, 2018, vol. 24, # 18, p. 4519 - 4522
  • 12
  • [ 624-38-4 ]
  • [ 5467-74-3 ]
  • [ 17788-94-2 ]
YieldReaction ConditionsOperation in experiment
84% With sodium carbonate In toluene (1)
Synthesis of 4,4"-dibromo-p-terphenyl
Toluene 600 ml and a 2M sodium carbonate aqueous solution 300 ml were added to 1,4-diiodobenzene 33.0 g, 4-bromophenylboronic acid 48.2 g and tetrakis(triphenylphosphine)palladium (0) 4.62 g under argon atmosphere, and the mixture was refluxed for 10 hours under heating.
After finishing the reaction, the mixture was immediately filtered, and the aqueous layer was removed.
The organic layer was dried on sodium sulfate and then concentrated.
A solid matter thus obtained was recrystallized from toluene to obtain 32.6 g of white crystal of 4,4"-dibromo-p-terphenyl (yield: 84percent)
Reference: [1] Patent: WO2006/114921, 2006, A1, . Location in patent: Page/Page column 45-48
[2] Patent: US2006/232198, 2006, A1,
  • 13
  • [ 3435-51-6 ]
  • [ 624-38-4 ]
  • [ 13001-40-6 ]
Reference: [1] Journal of the American Society for Mass Spectrometry, 2017, vol. 28, # 12, p. 2548 - 2560
  • 14
  • [ 624-38-4 ]
  • [ 109-94-4 ]
  • [ 591-50-4 ]
  • [ 51934-41-9 ]
YieldReaction ConditionsOperation in experiment
69%
Stage #1: With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5 h;
Stage #2: at -78℃; for 3 h;
Stage #3: With ethanol; iodine; potassium carbonate In tetrahydrofuran; hexane at -78 - 20℃; for 16 h;
General procedure: n-BuLi (1.67 M solution in hexane, 1.32 mL, 2.2 mmol) was added dropwise into a solution of p-bromochlorobenzene (383 mg, 2.0 mmol) in THF (3 mL) at -78 °C for 30 min. Then, ethyl formate (1.6 mL, 20 mmol) was added to the mixture and the obtained mixture was stirred at -78 °C. After 3 h at the same temperature, I2 (1523 mg, 6 mmol), K2CO3 (1382 mg, 10 mmol) and EtOH (3 mL) were added at -78 °C and the mixture was stirred for 14 h at rt. The reaction mixture was quenched with satd aq Na2SO3 (5 mL) and was extracted with CHCl3 (3.x.20 mL). The organic layer was washed with brine and dried over Na2SO4 to provide ethyl 4-chlorobenzoate in 77percent yield. If necessary, the product was purified by short column chromatography (SiO2:hexane:EtOAc=9:1) to give pure ethyl 4-chloro-1-benzoate as a colorless oil.
Reference: [1] Tetrahedron, 2012, vol. 68, # 24, p. 4701 - 4709
  • 15
  • [ 624-38-4 ]
  • [ 131379-16-3 ]
  • [ 37527-56-3 ]
  • [ 47230-38-6 ]
  • [ 51934-41-9 ]
Reference: [1] Bulletin of the Chemical Society of Japan, 2001, vol. 74, # 12, p. 2415 - 2420
  • 16
  • [ 624-38-4 ]
  • [ 766-99-4 ]
Reference: [1] Organic Letters, 2007, vol. 9, # 5, p. 737 - 740
[2] Journal of the American Chemical Society, 2013, vol. 135, # 4, p. 1264 - 1267
[3] Chemistry - A European Journal, 2013, vol. 19, # 48, p. 16240 - 16247
[4] Angewandte Chemie - International Edition, 2017, vol. 56, # 49, p. 15649 - 15653[5] Angew. Chem., 2017, vol. 129, p. 15855 - 15859,5
  • 17
  • [ 624-38-4 ]
  • [ 74-88-4 ]
  • [ 35371-03-0 ]
Reference: [1] Dyes and Pigments, 2011, vol. 89, # 3, p. 246 - 253
[2] Chemistry - A European Journal, 2001, vol. 7, # 23, p. 5118 - 5134
  • 18
  • [ 688-74-4 ]
  • [ 624-38-4 ]
  • [ 5122-99-6 ]
Reference: [1] Journal of the American Chemical Society, 1955, vol. 77, p. 4834,4837
  • 19
  • [ 624-38-4 ]
  • [ 5122-99-6 ]
Reference: [1] Journal of the Chemical Society [Section] C: Organic, 1966, p. 566 - 571
  • 20
  • [ 624-38-4 ]
  • [ 4151-80-8 ]
Reference: [1] Journal of the Chemical Society [Section] C: Organic, 1966, p. 566 - 571
  • 21
  • [ 383-63-1 ]
  • [ 624-38-4 ]
  • [ 23516-84-9 ]
Reference: [1] Journal of Medicinal Chemistry, 2006, vol. 49, # 7, p. 2200 - 2209
[2] Journal of Medicinal Chemistry, 2012, vol. 55, # 14, p. 6554 - 6565
[3] Nucleosides and Nucleotides, 1998, vol. 17, # 7, p. 1163 - 1175
  • 22
  • [ 624-38-4 ]
  • [ 1066-54-2 ]
  • [ 134856-58-9 ]
Reference: [1] Chemistry - A European Journal, 2017, vol. 23, # 7, p. 1623 - 1633
[2] Journal of Organic Chemistry, 1999, vol. 64, # 6, p. 1968 - 1971
[3] Chemistry - A European Journal, 2013, vol. 19, # 48, p. 16240 - 16247
[4] European Journal of Organic Chemistry, 2006, # 14, p. 3087 - 3096
[5] Organic Letters, 2007, vol. 9, # 5, p. 737 - 740
[6] Tetrahedron Letters, 2008, vol. 49, # 16, p. 2569 - 2574
[7] Journal of the American Chemical Society, 2013, vol. 135, # 4, p. 1264 - 1267
[8] Chemical Communications, 2016, vol. 52, # 90, p. 13237 - 13240
[9] Angewandte Chemie - International Edition, 2017, vol. 56, # 49, p. 15649 - 15653[10] Angew. Chem., 2017, vol. 129, p. 15855 - 15859,5
  • 23
  • [ 624-38-4 ]
  • [ 1066-54-2 ]
  • [ 17938-13-5 ]
  • [ 134856-58-9 ]
Reference: [1] Green Chemistry, 2009, vol. 11, # 11, p. 1821 - 1825
[2] Journal of Molecular Structure, 2009, vol. 938, # 1-3, p. 245 - 253
  • 24
  • [ 624-38-4 ]
  • [ 63697-96-1 ]
Reference: [1] Tetrahedron Letters, 2007, vol. 48, # 33, p. 5817 - 5820
[2] Chemistry - A European Journal, 2001, vol. 7, # 23, p. 5118 - 5134
  • 25
  • [ 624-38-4 ]
  • [ 77123-57-0 ]
Reference: [1] Tetrahedron Letters, 2007, vol. 48, # 33, p. 5817 - 5820
[2] Chemistry - A European Journal, 2001, vol. 7, # 23, p. 5118 - 5134
[3] European Journal of Organic Chemistry, 2016, vol. 2016, # 1, p. 17 - 21
  • 26
  • [ 624-38-4 ]
  • [ 1692-15-5 ]
  • [ 113682-56-7 ]
  • [ 83420-59-1 ]
YieldReaction ConditionsOperation in experiment
51% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; methanol at 95℃; for 12 h; Inert atmosphere General procedure: To a solution of diiodarene 1 or 5a–c (0.306mmol) in 1,4-dioxane/MeOH (2:1, 10mL) K2CO3 (126mg, 0.918mmol) was added. The mixture was degassed by bubbling nitrogen gas through it for 15min. Pd(PPh3)4 (17mg, 0.015mmol) was added and the solution was heated to 95°C. A solution of the boronic acid (0.275mmol) in 1,4-dioxane (5mL) was added dropwise to the reaction mixture for 10h using a syringe pump. After the addition was complete, the reaction mixture was stirred at 95°C for an additional 2h. It was then allowed to cool to room temperature, the solvent was removed under reduced pressure, the residue dispersed in CH2Cl2 (10mL). This suspension was washed with water, upon which the organic phase cleared up. It was dried dried over anhydrous CaCl2, filtered and concentrated to dryness. The desired product was purified by chromatography on silica gel using 0→5percent CH2Cl2 in cyclohexane as eluent.
Reference: [1] Tetrahedron Letters, 2018, vol. 59, # 20, p. 1948 - 1951
Same Skeleton Products
Historical Records

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[ 624-38-4 ]

Chemical Structure| 1246817-17-3

A1267778[ 1246817-17-3 ]

1,4-Diiodobenzene-13C6

Reason: Stable Isotope