[ CAS No. 13064-64-7 ] {[proInfo.proName]}

Name: 13064-64-7|2,5-Diiodobenzene-1,4-diol|95%
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Quality Control of [ 13064-64-7 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 13064-64-7 ]

Product Details of [ 13064-64-7 ]

CAS No. :	13064-64-7	MDL No. :	MFCD09910095
Formula :	C₆H₄I₂O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	XDLGDTUOWIFMQC-UHFFFAOYSA-N
M.W :	361.90	Pubchem ID :	18504287
Synonyms :

Calculated chemistry of [ 13064-64-7 ]

Physicochemical Properties

Num. heavy atoms :	10
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	2.0
Num. H-bond donors :	2.0
Molar Refractivity :	55.92
TPSA :	40.46 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	Yes
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.73 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.81
Log Po/w (XLOGP3) :	2.51
Log Po/w (WLOGP) :	2.31
Log Po/w (MLOGP) :	2.64
Log Po/w (SILICOS-IT) :	2.83
Consensus Log Po/w :	2.42

Druglikeness

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

Water Solubility

Log S (ESOL) :	-4.11
Solubility :	0.0282 mg/ml ; 0.0000778 mol/l
Class :	Moderately soluble
Log S (Ali) :	-3.01
Solubility :	0.357 mg/ml ; 0.000987 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.1
Solubility :	0.287 mg/ml ; 0.000794 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	2.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.23

Safety of [ 13064-64-7 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 13064-64-7 ]

* 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 [ 13064-64-7 ]
Downstream synthetic route of [ 13064-64-7 ]

[ 13064-64-7 ] Synthesis Path-Upstream 1~2

1
[ 13064-64-7 ]
[ 5332-06-9 ]

Reference： [1] Patent: US2014/39132, 2014, A1, . Location in patent: Page/Page column

2
[ 13064-64-7 ]
[ 6621-59-6 ]

Reference： [1] Patent: US2014/39132, 2014, A1, . Location in patent: Page/Page column

[ 13064-64-7 ] Synthesis Path-Downstream 1~53

1
[ 51560-21-5 ]
[ 13064-64-7 ]

Yield	Reaction Conditions	Operation in experiment
90%	With boron tribromide; In dichloromethane; at -80 - 20℃; for 12h;	Example 3.3; Synthesis of 2,5-diiodo- 1 ,4-hydroquinone; A solution of 2,5-diiodo- 1,4-dimethoxybenzene (3.0Og, 7.69 mmol) in 30 ml ofAnhydrous dichloromethane was cooled to -80C and BBr3 (19 ml, 16.93 mmol) was added drop wise. The mixture was allowed to rt and stirred for additional 12h, solid precipitate was formed, collected and then crystallized from ethanol-water. The trace of solvent was evaporated at reduced pressure(2.50 g, yield 90 %).
87.1%	With boron tribromide; In dichloromethane; for 0.5h;Cooling with ice;	Compound 8 (1.0 g, 2.56 × 10 -3 mol) was dissolved in dichloromethane (20 mL) and stirred in an ice-salt bath for 30 minutes.A 1.0 M solution of BBr3 in dichloromethane (6.14 mL, 6.14 × 10 -3 mol) was added to the solution, and the mixture was stirred overnight.afterwards,After adding deionized water to the reaction mixture until no white smoke is generated,Suction filtration was performed.The obtained solid is dried under vacuum,Compound 9 was obtained as a white solid (yield 0.81 g, 87.1%).
80%		A two-neck round bottom flask (250ml) was cooled to -63 C in a liquid nitrogen/chloroform slush bath to which 1,4-diiodo 2,5-dimethoxybenzene (2.0g, 5.1mmol, 1.0 equiv) was dissolved in dichloromethane (40ml) under nitrogen. BBr3 (12ml, 1.0M, 12mmol) was then added dropwise through a septa seal using a syringe. The mixture was allowed to warm to room temperature and stirred for 24hrs and then carefully quenched with water (75ml). The aqueous layer was then extracted with ether (3 * 50ml). The combined organic phases were extracted with NaOH (150ml, 2N). The NaOH solution was then neutralized in dilute HCl in an ice bath to form a pink precipitate that was collected and dried. The resultant solid material was recrystallized from toluene to give light brown crystals, (1.48g, 80%).

	With boron tribromide; In dichloromethane; at -78 - 20℃;	Compound b is dissolved in non-water, methylene chloride, and for cooling to -78 degrees, by adding dropwise boron tribromide (in pre-dissolved in methylene chloride), in the charging process keeping the temperature at -78 degrees. After adds the bromide boron, the room temperature gradually return to the reaction system, and continuing to stir, the pink reaction liquid. Under stirring conditions, the pink solution is slowly dropped into ice water, to produce a solid immediately, filtering and collecting the solid, to obtain gray solid, compound c is obtained after drying under vacuum.
	With boron tribromide; In dichloromethane; at -78 - 20℃; for 16h;Inert atmosphere;	Under nitrogen, the 7.8g 2,5-diiodo-1,4-methoxybenzene was dissolved in 50mL of dichloromethane, and at -78 condition, to the solution was added dropwise 5.58mL three boron bromide. After completion of the dropwise addition, stirred for 16 hours at room temperature, the solid was suction filtered to produce a large number, and dried in vacuo to give a white solid which is 2,5-diiodo-1,4-bis(hydroxy)benzene. Among these, 2,5-diiodo-1,4-di(methoxybenzene, boron tribromide in methylenechloride and the molar ratio of 1: 3:40;
	With boron tribromide; In dichloromethane; at -78℃; for 16h;Inert atmosphere;	Under an argon atmosphere, 15.6 g of compound 1 was dissolved in 100 mL of dichloromethane,And 8.18 mL of boron tribromide was added dropwise to the solution at -78 C.Wherein the molar ratio of compound 1, boron tribromide and methylene chloride is 1: 2.2: 40. The reaction was stirred for 16 hours,After completion of the reaction, the reaction solution was transferred to an ice-water mixture and stirred, suction-filtered and dried in vacuo to give a white solid.
	With boron tribromide; In dichloromethane; for 96h;Cooling with acetone-dry ice;	Compound 4-1 (10.06 g, 25.8 mmol) was dissolved in 100 mL of dry dichloromethane,The reaction flask was then cooled in a dry ice acetone bath,A solution of 1 mol / L boron tribromide in dichloromethane (56.8 mL, 56.8 mmol) was slowly added dropwise,Natural warmingreaction4 days.100 mL of ice water was allowed to cool in an ice-water bath, and then the reaction solution was gradually dropped into it with stirring,Produce a lot of solid, standing. Filtered with a Buchner funnel, the solid was washed three times with ice water, dried in vacuo,To give white solid compound 5-1 (8.71 g, 24.1 mmol)Yield: 93%; characterization: white solid;
	With boron tribromide; In dichloromethane; at -78 - 20℃;	The compound was synthesized following the method described in Zhao and Schanze, Chem. Commun 2010, 46, 6075-6077, but using compound 6 as the amine. NMR (CD Cl 3, 300 MHz, 6ppm): 7.14 (s, 2H), 6.55 (br, s, 2H), 4.66 (br, s, 6H), 4.34 (s, 4H), 3.03 (m, 12H), 1.76 (m, 12H), 1.45 (m; 12H), 1.43 (s, 54H). 13C NMR (CDCh, 75 MHz, 5ppm): 166.0, 156.2, 151.7 122.7, 86.5, 79.4, 68.7, 58.9, 40.9, 32.9, 28.7, 24.2. HRMS: (ESI+) m/z calcd for CeoHiiuHNsOie [(M + H)]+ 1447.5732, found 1447.5706.

Reference： [1]Chemical Communications,2017,vol. 53,p. 7628 - 7631
[2]Chemical Communications,2002,p. 2526 - 2527
[3]Chemical Communications,2006,p. 1983 - 1985
[4]Patent: WO2008/96239,2008,A1 .Location in patent: Page/Page column 29
[5]Journal of the American Chemical Society,1997,vol. 119,p. 4622 - 4632
[6]Journal of the American Chemical Society,2001,vol. 123,p. 6714 - 6715
[7]Patent: JP2020/2024,2020,A .Location in patent: Paragraph 0092; 0093
[8]Journal of the American Chemical Society,1995,vol. 117,p. 7017 - 7018
[9]Journal of the American Chemical Society,1995,vol. 117,p. 12593 - 12602
[10]Tetrahedron Letters,2016,vol. 57,p. 1739 - 1742
[11]Macromolecules,2005,vol. 38,p. 234 - 243
[12]Chemical Communications,2003,p. 650 - 651
[13]European Journal of Organic Chemistry,1998,p. 335 - 348
[14]Organic Letters,2008,vol. 10,p. 1341 - 1344
[15]Angewandte Chemie - International Edition,2009,vol. 48,p. 6461 - 6464
Angewandte Chemie,2009,vol. 121,p. 6583 - 6586
[16]Angewandte Chemie - International Edition,2009,vol. 48,p. 9646 - 9651
[17]Polymer,2010,vol. 51,p. 3425 - 3430
[18]Chemical Communications,2012,vol. 48,p. 964 - 966
[19]Synlett,2012,vol. 23,p. 778 - 782
[20]Advanced Functional Materials,2012,vol. 22,p. 1076 - 1086
[21]Patent: WO2013/20096,2013,A2 .Location in patent: Page/Page column 19; 47
[22]Patent: CN104151174,2016,B .Location in patent: Paragraph 0011; 0016; 0017
[23]Patent: WO2016/115362,2016,A1 .Location in patent: Paragraph 0098
[24]Patent: CN104031108,2016,B .Location in patent: Paragraph 0088; 0089; 0123; 0124; 0146; 0147
[25]Patent: CN104893714,2016,B .Location in patent: Paragraph 0104-0105
[26]Chemical Communications,2017,vol. 53,p. 9414 - 9417
[27]Patent: CN106496049,2017,A .Location in patent: Paragraph 0026
[28]Patent: CN104151173,2017,B .Location in patent: Paragraph 0016; 0017
[29]Angewandte Chemie - International Edition,2017,vol. 56,p. 15649 - 15653
Angew. Chem.,2017,vol. 129,p. 15855 - 15859,5
[30]Chemistry - A European Journal,2018,vol. 24,p. 3132 - 3135
[31]Patent: WO2019/169169,2019,A1 .Location in patent: Paragraph 0041

2
[ 628-89-7 ]
[ 13064-64-7 ]
[ 173068-97-8 ]

Reference： [1]Journal of the American Chemical Society,1995,vol. 117,p. 7017 - 7018
[2]Journal of the American Chemical Society,1995,vol. 117,p. 12593 - 12602

3
[ 111-25-1 ]
[ 13064-64-7 ]
[ 357396-86-2 ]

Reference： [1]Chemistry - A European Journal,2008,vol. 14,p. 1205 - 1215
[2]Journal of the American Chemical Society,1997,vol. 119,p. 4622 - 4632
[3]Chemical Communications,2002,p. 2526 - 2527

4
[ 100-39-0 ]
[ 13064-64-7 ]
[ 203579-40-2 ]

Reference： [1]Organic Letters,2007,vol. 9,p. 595 - 598
[2]European Journal of Organic Chemistry,1998,p. 335 - 348

5
[ 13064-64-7 ]
[ 627-18-9 ]
[ 195990-28-4 ]

Yield	Reaction Conditions	Operation in experiment
74%	With potassium carbonate; sodium iodide; In butanone; at 70℃; for 24h;Inert atmosphere;	Under nitrogen protection, 2-butanone (40 mL) was added to a 100 mL round-bottom flask containing 1,4-diiodo-2,5-hydroquinone (1.53 g, 5.70 mmol), 3-bromo-1-propanol (1.74 g, 12.5 mmol), K2CO3 (6.32 g, 45.8 mmol) and NaI (0.20 g, 1.29 mmol), then the reaction mixture was stirred at 70 C for 24 h. After it was cooled to room temperature, the precipitate was filtered away and the filtrate was washed with aqueous sodium hydroxide (0.1 M), water and brine, and then dried over anhydrous sodium sulfate. After the solvent was removed, the residue was recrystallized from petroleum ether/dichloromethane (3:1) to afford white solid (2.0 g, yield: 74%). 1H NMR (400 MHz, DMSO-d6): delta (ppm) 7.05 (s, 2H), 4.07 (t, 4H, J=9.6), 3.65 (s, 2H), 3.54 (qua, 4H, J=13.8), 1.94 (m, 4H, J=19.6). Anal. Calcd for C12H16I2O4: C, 30.15; H, 3.37. Found: C, 30.28; H, 3.45.

Reference： [1]Polymer,2016,vol. 102,p. 143 - 152
[2]Tetrahedron,1997,vol. 53,p. 11899 - 11912

6
[ 13064-64-7 ]
[ 571167-64-1 ]
[ 571167-65-2 ]

Reference： [1]Tetrahedron Letters,2003,vol. 44,p. 4487 - 4490

7
[ 16728-06-6 ]
[ 13064-64-7 ]
[ 730952-19-9 ]

Reference： [1]Journal of the American Chemical Society,2004,vol. 126,p. 7460 - 7461

8
[ 59014-60-7 ]
[ 13064-64-7 ]
[ 475265-41-9 ]

Yield	Reaction Conditions	Operation in experiment
62%	With potassium hydroxide In dimethyl sulfoxide at 20℃;
0.8 g	With potassium carbonate In N,N-dimethyl-formamide at 50℃; for 12h;

Reference： [1]Lee, Dong-Chan; Chang, Bong-Jun; Morales, Gustavo M.; Jang, Young Ah; Ng, Man-Kit; Heller, Stephen T.; Yu, Luping [Macromolecules, 2004, vol. 37, # 5, p. 1849 - 1856]
[2]Chan, Eugene W. L.; Lee, Dong-Chan; Ng, Man-Kit; Wu, Guohui; Lee, Ka Yee C.; Yu, Luping [Journal of the American Chemical Society, 2002, vol. 124, # 41, p. 12238 - 12243]

9
[ 850090-13-0 ]
[ 13064-64-7 ]
[ 850090-14-1 ]

Yield	Reaction Conditions	Operation in experiment
75%	With potassium carbonate; potassium iodide In butanone for 16h; Heating;

Reference： [1]Wosnick, Jordan H.; Mello, Charlene M.; Swager, Timothy M. [Journal of the American Chemical Society, 2005, vol. 127, # 10, p. 3400 - 3405]

10
[ 850090-10-7 ]
[ 13064-64-7 ]
[ 850090-11-8 ]

Yield	Reaction Conditions	Operation in experiment
48%	With potassium carbonate; potassium iodide In butanone for 20h; Heating;

Reference： [1]Wosnick, Jordan H.; Mello, Charlene M.; Swager, Timothy M. [Journal of the American Chemical Society, 2005, vol. 127, # 10, p. 3400 - 3405]

11
2,5,8,11,15,18,21,24-octaoxapentacosan-13-yl 4-methylbenzenesulfonate [ No CAS ]
[ 13064-64-7 ]
[ 848410-53-7 ]

Reference： [1]Journal of Organic Chemistry,2013,vol. 78,p. 4949 - 4959
[2]Chemical Communications,2005,p. 584 - 586
[3]Journal of Materials Chemistry,2012,vol. 22,p. 2781 - 2790
[4]Chemical Communications,2006,p. 1983 - 1985

12
[ 5197-62-6 ]
[ 13064-64-7 ]
[ 540759-89-5 ]

Reference： [1]Journal of the American Chemical Society,2008,vol. 130,p. 6952 - 6954
[2]Chemistry - A European Journal,2004,vol. 10,p. 6247 - 6254

13
[ 14660-52-7 ]
[ 13064-64-7 ]
[ 795277-27-9 ]

Reference： [1]Analytical Chemistry,2004,vol. 76,p. 6513 - 6518

14
[ 75-77-4 ]
[ 13064-64-7 ]
[ 1046451-10-8 ]

Yield	Reaction Conditions	Operation in experiment
94%	With 1,1,1,3,3,3-hexamethyl-disilazane; In acetonitrile; at 20℃; for 16h;	Example 3.4; Synthesis of l,4-bis-0-trimethylsilyl-2,5-diiodohydroquinone.; <n="32"/>2,5-diiodo-l,4-hydroquinone (1.000 g, 2.76 mmol), chlorotrimethylsilane (0.77ml, 6.07 mmol) and 1,1,1,3,3,3-hexamethyldisilazane (1.29 ml, 6.07 mmol) were dissolved in 6 ml of dry acetonitrile. The reaction mixture was stirred under nitrogen at r.t. for 16 h, and then the solvent was removed at reduced pressure. The residue was dissolved in petroleum ether and filtered to remove precipitated salts. The solution was washed with saturated aqueous bicarbonate and brine, dried over anhydrous Na2SO4, and evaporated to dryness. 1.308 g (94% yield) of the crude product were obtained. IR (KBr): v 2959, 1461, 1347, 1252, 1204, 1046, 908, 841 cm"1; 1HNMR (500 MHz, CDCl3): delta 0.35 (s, 18H), 7.15 (s, 2H) ppm.

Reference： [1]Patent: WO2008/96239,2008,A1 .Location in patent: Page/Page column 29-30
[2]Chemical Communications,2003,p. 130 - 131

15
[ 1120-71-4 ]
[ 13064-64-7 ]
3,3'-[(2,5-diiodo-1,4-phenylene)bis(oxy)]bis-(1-propanesulfonic acid) disodium salt [ No CAS ]

Reference： [1]Chemical Communications,2002,p. 446 - 447
[2]Organic Letters,2008,vol. 10,p. 1341 - 1344

16
[ 109-64-8 ]
[ 13064-64-7 ]
1,4-bis(3-bromopropoxy)-2,5-diiodobenzene [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2000,vol. 122,p. 12389 - 12390
[2]Patent: WO2013/20096,2013,A2 .Location in patent: Page/Page column 19; 47
[3]Patent: WO2016/115362,2016,A1 .Location in patent: Paragraph 0098

17
[ 3383-83-3 ]
[ 13064-64-7 ]
[ 921869-63-8 ]

Reference： [1]Angewandte Chemie - International Edition,2006,vol. 45,p. 1548 - 1553

18
[ 18162-48-6 ]
[ 13064-64-7 ]
((2,5-diiodo-1,4-phenylene)bis(oxy))bis(tert-butyldimethylsilane) [ No CAS ]

Reference： [1]Macromolecules,2005,vol. 38,p. 4569 - 4576

19
[ 18880-00-7 ]
[ 13064-64-7 ]
[ 929803-60-1 ]