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[ CAS No. 16004-15-2 ] {[proInfo.proName]}

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Chemical Structure| 16004-15-2
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Product Citations

Product Citations

Zehuan Huang ; Xiaoyi Chen ; Stephen J. K. O’Neill , et al. DOI: PubMed ID:

Abstract: Supramolecular polymer networks are non-covalently crosslinked soft materials that exhibit unique mechanical features such as self-healing, high toughness and stretchability. Previous studies have focused on optimizing such properties using fast-dissociative crosslinks (that is, for an aqueous system, dissociation rate constant kd > 10 s−1). Herein, we describe non-covalent crosslinkers with slow, tuneable dissociation kinetics (kd < 1 s−1) that enable high compressibility to supramolecular polymer networks. The resultant glass-like supramolecular networks have compressive strengths up to 100 MPa with no fracture, even when compressed at 93% strain over 12 cycles of compression and relaxation. Notably, these networks show a fast, room-temperature self-recovery (< 120 s), which may be useful for the design of high-performance soft materials. Retarding the dissociation kinetics of non-covalent crosslinks through structural control enables access of such glass-like supramolecular materials, holding substantial promise in applications including soft robotics, tissue engineering and wearable bioelectronics.

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Product Details of [ 16004-15-2 ]

CAS No. :16004-15-2 MDL No. :MFCD00209656
Formula : C7H6BrI Boiling Point : -
Linear Structure Formula :- InChI Key :BQTRMYJYYNQQGK-UHFFFAOYSA-N
M.W : 296.93 Pubchem ID :954258
Synonyms :

Calculated chemistry of [ 16004-15-2 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 9
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.14
Num. rotatable bonds : 1
Num. H-bond acceptors : 0.0
Num. H-bond donors : 0.0
Molar Refractivity : 52.0
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) : -5.26 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.4
Log Po/w (XLOGP3) : 4.02
Log Po/w (WLOGP) : 3.03
Log Po/w (MLOGP) : 3.98
Log Po/w (SILICOS-IT) : 3.82
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) : -4.64
Solubility : 0.00679 mg/ml ; 0.0000229 mol/l
Class : Moderately soluble
Log S (Ali) : -3.72
Solubility : 0.0562 mg/ml ; 0.000189 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.59
Solubility : 0.00756 mg/ml ; 0.0000255 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.22

Safety of [ 16004-15-2 ]

Signal Word:Danger Class:8
Precautionary Statements:P280-P305+P351+P338-P310 UN#:3261
Hazard Statements:H314 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 16004-15-2 ]

* 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 [ 16004-15-2 ]
  • Downstream synthetic route of [ 16004-15-2 ]

[ 16004-15-2 ] Synthesis Path-Upstream   1~15

  • 1
  • [ 624-31-7 ]
  • [ 16004-15-2 ]
  • [ 51628-12-7 ]
YieldReaction ConditionsOperation in experiment
45% With N-Bromosuccinimide In tetrachloromethane; water; dimethyl sulfoxide Referential Example 4
[Preparation of 4-Iodophenylacetonitrile]
A mixture of p-iodotoluene (4.36 g, 20 mmol, purchased from Tokyo Kasei) and N-bromosuccinimide (3.92 g, 22 mmol, purchased from Tokyo Kasei) in 60 ml of carbontetrachloride (purchased from Wako Junyaku Kogyo) was refluxed for 4 hours under irradiation by means of an incandescent lamp to give 2.67 g (yield: 45.0percent) of 4-iodobenzyl bromide as a white crystalline.
To a hot solution (50° C.) of sodium cyanide 0.49 g, 10.0 mmom, purchased from Kokusan Kagaku) in 10 ml of dimethyl sulfoxide (purchased from Aldrich) was added the above 4-iodobenzyl bromide (1.48 g, 5.0 mmol) and the mixture was stirred for three hours at ambient temperature.
To the resultant reaction mass was added water and extracted with hexane.
The solvent was removed to give 0.84 g (yield: 69percent) of 4-iodophenylacetonitrile as a white crystalline.
Reference: [1] Patent: US5589506, 1996, A,
[2] Patent: US5589506, 1996, A,
  • 2
  • [ 16004-15-2 ]
  • [ 51628-12-7 ]
YieldReaction ConditionsOperation in experiment
56% for 1 h; Reflux General procedure: To 8 mmol of the correspondingly substituted bromomethylbenzene in 40 ml of ethanol was added 2 ml of 6 M potassium cyanide solution. The reaction mixture was refluxed for 1 h. On cooling, the mixture was concentrated by rotary evaporation under vacuum to remove the ethanol. The residue was washed with deionized water and recrystallized from ethanol/water to give the product.
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 15, p. 3341 - 3345
[2] European Journal of Medicinal Chemistry, 2013, vol. 65, p. 1 - 11
[3] Patent: WO2003/99276, 2003, A1, . Location in patent: Page 366-367
  • 3
  • [ 16004-15-2 ]
  • [ 151-50-8 ]
  • [ 51628-12-7 ]
Reference: [1] Journal of Medicinal Chemistry, 2005, vol. 48, # 5, p. 1336 - 1343
[2] Chemische Berichte, 1878, vol. 11, p. 56
  • 4
  • [ 773837-37-9 ]
  • [ 16004-15-2 ]
  • [ 51628-12-7 ]
Reference: [1] Journal of Organic Chemistry, 2017, vol. 82, # 2, p. 1114 - 1126
  • 5
  • [ 16004-15-2 ]
  • [ 1798-06-7 ]
Reference: [1] Chemische Berichte, 1878, vol. 11, p. 56
  • 6
  • [ 16004-15-2 ]
  • [ 1643-29-4 ]
Reference: [1] Journal of Organic Chemistry, 2006, vol. 71, # 12, p. 4516 - 4520
  • 7
  • [ 16004-15-2 ]
  • [ 98-80-6 ]
  • [ 2567-29-5 ]
Reference: [1] Tetrahedron Letters, 2004, vol. 45, # 37, p. 6959 - 6962
  • 8
  • [ 624-31-7 ]
  • [ 16004-15-2 ]
YieldReaction ConditionsOperation in experiment
60.3% With N-Bromosuccinimide; dibenzoyl peroxide In tetrachloromethane for 7 h; Heating / reflux; Photolysis Synthesis of Compound 1D [0026] p-Iodotoluene (Compound 1C, 25 g), N-bromosuccinimide (23.5 g) and benzoyl peroxide (375 mg) were added to carbon tetrachloride (375 ml) and refluxed with heating for 7 hours under photoirradiation. Further, the reaction mixture was stirred overnight at room temperature, then insoluble matters were removed by filtration, and the filtrate was concentrated under reduced pressure. The concentrated residue was recrystallized from ethyl acetate and hexane to obtain Compound 1D (yield: 60.3percent). [0027] NMR chemical shift, CDCl3, TMS as standard [0028] d 7.72 (d, 2H), 7.14 (d, 2H), 4.39 (s, 2H)
Reference: [1] Macromolecules, 2013, vol. 46, # 12, p. 4754 - 4763
[2] Acta Crystallographica Section C: Crystal Structure Communications, 2003, vol. 59, # 4, p. o216-o218
[3] Journal of Materials Chemistry C, 2015, vol. 3, # 4, p. 734 - 741
[4] Chemistry - An Asian Journal, 2017, vol. 12, # 6, p. 690 - 697
[5] Journal of Organic Chemistry, 2014, vol. 79, # 1, p. 223 - 229
[6] Journal of Organic Chemistry, 2017, vol. 82, # 2, p. 1114 - 1126
[7] Tetrahedron, 2003, vol. 59, # 7, p. 1021 - 1032
[8] Angewandte Chemie - International Edition, 2018, vol. 57, # 3, p. 800 - 804[9] Angew. Chem., 2018, vol. 57, # 3, p. 800 - 804,5
[10] Patent: US2004/228793, 2004, A1, . Location in patent: Page/Page column 4
[11] Journal of Medicinal Chemistry, 1989, vol. 32, # 5, p. 1057 - 1062
[12] Chemistry - A European Journal, 2012, vol. 18, # 23, p. 7229 - 7242
[13] Journal of the Chemical Society, 1949, p. 1089,1096
[14] Chem. Penicillin, &lt;Princeton 1949&gt;, S. 94,
[15] Journal of the American Chemical Society, 1948, vol. 70, p. 2310,2313
[16] American Chemical Journal, 1880, vol. 2, p. 250
[17] American Chemical Journal, 1879, vol. 1, p. 103
[18] Chemische Berichte, 1878, vol. 11, p. 55
[19] American Chemical Journal, 1908, vol. 40, p. 466
[20] Recueil des Travaux Chimiques des Pays-Bas, 1923, vol. 42, p. 522
[21] Journal of the American Chemical Society, 1949, vol. 71, p. 3360
[22] Journal of Organic Chemistry, 1949, vol. 14, p. 228,232
[23] Phosphorus, Sulfur and Silicon and the Related Elements, 1990, vol. 53, # 1-4, p. 43 - 67
[24] Tetrahedron Letters, 1994, vol. 35, # 3, p. 481 - 484
[25] Journal of the American Chemical Society, 2001, vol. 123, # 5, p. 946 - 953
[26] Advanced Synthesis and Catalysis, 2004, vol. 346, # 7, p. 767 - 776
[27] Patent: EP1647546, 2006, A1, . Location in patent: Page/Page column 54
[28] Organic Letters, 2013, vol. 15, # 16, p. 4194 - 4197
[29] European Journal of Organic Chemistry, 2014, vol. 2014, # 16, p. 3402 - 3410
  • 9
  • [ 18282-51-4 ]
  • [ 16004-15-2 ]
Reference: [1] Beilstein Journal of Organic Chemistry, 2011, vol. 7, p. 1648 - 1655
[2] Organic Letters, 2018, vol. 20, # 10, p. 3061 - 3064
[3] Journal of Medicinal Chemistry, 2006, vol. 49, # 7, p. 2155 - 2165
[4] Journal of Organic Chemistry, 1995, vol. 60, # 3, p. 523 - 528
[5] Medicinal Chemistry Research, 1995, vol. 5, # 8, p. 618 - 630
[6] Chemistry - A European Journal, 2009, vol. 15, # 10, p. 2278 - 2288
[7] Bioorganic and Medicinal Chemistry, 2007, vol. 15, # 9, p. 3187 - 3200
[8] Organic Letters, 2015, vol. 17, # 15, p. 3810 - 3813
  • 10
  • [ 624-31-7 ]
  • [ 34241-39-9 ]
  • [ 16004-15-2 ]
YieldReaction ConditionsOperation in experiment
45% With N-Bromosuccinimide In tetrachloromethane Step 1
4-Iodobenzyl bromide
A mixture of 4-iodotoluene (21.8 g, 100 mmol), N-bromosuccinimide (18.69 g, 105 mmol) and αα-azobisisobutyronitrile (100 mg) in carbon tetrachloride (100 ml) was refluxed for 20 hours.
The reaction was cooled, the precipitate filtered, washed with carbon tetrachloride (50 ml), and the filtrate evaporated.
The residue was chromatographed on silica, eluding with petrol (60°-80° C.) to give the product as a white solid (13 g, 45percent); δH (CDCl3) 4.42 (2H, ArCH2 Br), 7.11 (2H, d, J 15.3 Hz, 2-H, 6-H), 7.67 (2H, d, J 15.3 Hz, 3'-H, 5'-H).
Reference: [1] Patent: US5861407, 1999, A,
  • 11
  • [ 624-31-7 ]
  • [ 34241-39-9 ]
  • [ 16004-15-2 ]
Reference: [1] Patent: US5965738, 1999, A,
  • 12
  • [ 619-58-9 ]
  • [ 16004-15-2 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 2007, vol. 15, # 9, p. 3187 - 3200
  • 13
  • [ 18282-51-4 ]
  • [ 54589-53-6 ]
  • [ 16004-15-2 ]
Reference: [1] Beilstein Journal of Organic Chemistry, 2011, vol. 7, p. 1648 - 1655
  • 14
  • [ 506-68-3 ]
  • [ 16004-15-2 ]
  • [ 59709-66-9 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1933, vol. 507, p. 1,9
  • 15
  • [ 16004-15-2 ]
  • [ 39959-59-6 ]
Reference: [1] American Chemical Journal, 1880, vol. 2, p. 257
[2] Bioorganic and Medicinal Chemistry, 2007, vol. 15, # 9, p. 3187 - 3200
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