Home Cart 0 Sign in  
X

[ CAS No. 133-91-5 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
3d Animation Molecule Structure of 133-91-5
Chemical Structure| 133-91-5
Chemical Structure| 133-91-5
Structure of 133-91-5 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Search after Editing

* Storage: {[proInfo.prStorage]}

* Shipping: {[proInfo.prShipping]}

Quality Control of [ 133-91-5 ]

Related Doc. of [ 133-91-5 ]

Alternatived Products of [ 133-91-5 ]
Product Citations

Product Details of [ 133-91-5 ]

CAS No. :133-91-5 MDL No. :MFCD00002444
Formula : C7H4I2O3 Boiling Point : -
Linear Structure Formula :I2C6H2(OH)CO2H InChI Key :DHZVWQPHNWDCFS-UHFFFAOYSA-N
M.W : 389.91 Pubchem ID :8631
Synonyms :

Calculated chemistry of [ 133-91-5 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 3.0
Num. H-bond donors : 2.0
Molar Refractivity : 60.86
TPSA : 57.53 Ų

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) : -5.44 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.54
Log Po/w (XLOGP3) : 4.56
Log Po/w (WLOGP) : 2.3
Log Po/w (MLOGP) : 2.77
Log Po/w (SILICOS-IT) : 2.69
Consensus Log Po/w : 2.77

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.85

Water Solubility

Log S (ESOL) : -5.43
Solubility : 0.00143 mg/ml ; 0.00000368 mol/l
Class : Moderately soluble
Log S (Ali) : -5.49
Solubility : 0.00126 mg/ml ; 0.00000323 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -3.03
Solubility : 0.366 mg/ml ; 0.00094 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 1.85

Safety of [ 133-91-5 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302+H312+H332-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 133-91-5 ]

* 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.

  • Downstream synthetic route of [ 133-91-5 ]

[ 133-91-5 ] Synthesis Path-Downstream   1~100

  • 1
  • [ 133-91-5 ]
  • [ 42016-91-1 ]
YieldReaction ConditionsOperation in experiment
With phosphorus pentachloride; benzene at 60℃;
With thionyl chloride; Petroleum ether
With thionyl chloride; N,N-dimethyl-formamide In benzene at 60℃; for 1h;
With thionyl chloride at 120℃; for 0.666667h;
With phosphorus trichloride In chlorobenzene for 0.5h; Heating;
With thionyl chloride; N,N-dimethyl-formamide In toluene at 90℃; for 1.5h;
With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 0 - 25℃; for 2h; Inert atmosphere;
With thionyl chloride for 7h; Inert atmosphere; Reflux;
With thionyl chloride In dichloromethane at 40℃; for 1h;
With thionyl chloride for 7h; Reflux; Compounds 7e-i and 8 were synthesized according to published procedure.2 Briefly. 3,5-diiodosalicylic acid (or 3.5-dichlorosalicylic acid, 1 eq) was heated to reflux with SOCb(5 eq)for 7 h, and thereafter concentrated under reduced pressure. The corresponding acyl chloride product was precipitated with cold hexanes, filtered and air-dried. Coupling with the respective amine (1 eq) was performed in DMF in the presence of DIPEA (3 eq) at rt for 1 h. All salicylanilide products were purified by preparative HPLC. Reagents and solvents were obtained from commercial sources, and reactions were carried out using technique known to those having ordinary skill in the art.
With oxalic acid In dichloromethane at 20℃; for 3h; A.4 Commercially available 3,5-diiodosalysilic acid (20 g) was dissolved in DCM (150 ml). Oxalyl chloride (1.2 equivalents) and anhydrous DMF (3 drops) were added. The reaction mixture was stirred at room temperature for 3 hours, evaporated and co- evaporated with DCM, yielding 17.80 g of intermediate (27).
With thionyl chloride; N,N-dimethyl-formamide In dichloromethane for 6h; Reflux;
With thionyl chloride; N,N-dimethyl-formamide In dichloromethane at 60℃; for 6h; General Procedure for Path B. General procedure: Thionyl chloride (3 eq) was added dropwise to a suspension of carboxylic acid (1 eq) in anhydrous dichloromethane with vigorous stirring. Then a catalytic amount of DMF (100 pL for 1 g of carboxylic acid) was added and the reaction mixture was refluxed for 6 h. The organic solvent and excess thionyl chloride were evaporated under reduced pressure to afford the acyl chloride.
With thionyl chloride; N,N-dimethyl-formamide at 0 - 60℃; for 6h; Inert atmosphere; 2.1.2.2 Synthesis of 1,2-diacylhydrazines 3 1,2-Diacylhydrazines 3 were prepared by a two-step procedure from appropriate 4-substituted benzohydrazides and 3,5-diiodosalicylic acid.29 3,5-Diiodosalicylic acid (389.9 mg, 0.001 mol) was dissolved in thionyl chloride (7 mL) and after cooling to 0°C, 3 drops of N,N-dimethylformamide (DMF) were added. The mixture was to let stir without external cooling and then heated to 60°C under nitrogen atmosphere. After six hours, it was evaporated to dryness under reduced pressure. Crude 3,5-diiodosalicyloyl chloride was used further without any purification. It was added into dry tetrahydrofuran (THF; 7 mL) under nitrogen atmosphere, and under vigorous stirring, a solution composed of 1 mmol of 4-substituted benzohydrazide, 4 mmol of triethylamine (558 µL) and 7 mL of THF was added dropwise. Alternatively (3j), the hydrazide was added as a solid together with 2 equivalents of potassium carbonate. The mixture was stirred for 24 h at room temperature. Then, it was evaporated to dryness and using ethyl acetate, water and 0.1 M hydrochloric acid, it was transferred into a separation funnel. The organic phase was washed with 0.1 M aqueous hydrochloric acid, 5% aqueous sodium bicarbonate, 0.1 M hydrochloric acid again, followed by saturated brine. The organic phase was dried over anhydrous sodium sulfate. The filtrate was concentrated under reduced pressure and n-hexane was added to start precipitation. After 24 h at+4°C, the suspension was filtered off to give required derivatives 3 that were purified using crystallization from ethyl acetate, a mixture of THF/acetonitrile or column chromatography with the mixture of toluene with ethyl acetate 4:0.3 (v/v).

Reference: [1]Anschuetz,R. [Chemische Berichte, 1897, vol. 30, p. 222] Anschuetz,R.; Robitsek; Schmitz [Justus Liebigs Annalen der Chemie, 1906, vol. 346, p. 333,334] Current Patent Assignee: Akt.-Ges. f. Anilinf. - DE92537, 1800, C [Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 4, p. 157][Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 4, p. 157]
[2]Current Patent Assignee: BAYER AG - US2750393, 1954, A
[3]Macielag, Mark J.; Demers, James P.; Fraga-Spano, Stephanie A.; Hlasta, Dennis J.; Johnson, Sigmond G.; Kanojia, Ramesh M.; Russell, Ronald K.; Sui, Zhihua; Weidner-Wells, Michele A.; Werblood, Harvey; Foleno, Barbara D.; Goldschmidt, Raul M.; Loeloff, Michael J.; Webb, Glenda C.; Barrett, John F. [Journal of Medicinal Chemistry, 1998, vol. 41, # 16, p. 2939 - 2945]
[4]Cogswell III, Lawrence P.; Raines, Douglas E.; Parekh, Sonali; Jonas, Oliver; Maggio, John E.; Strichartz, Gary R. [Journal of Pharmaceutical Sciences, 2001, vol. 90, # 9, p. 1407 - 1423]
[5]Gong, Denghuang; Li, Jiafeng; Yuan, Chengye; Yuan, Junying [Synthetic Communications, 2005, vol. 35, # 1, p. 55 - 66]
[6]Location in patent: scheme or table Liu, Yaya; Donner, Pamela L.; Pratt, John K.; Jiang, Wen W.; Ng, Teresa; Gracias, Vijaya; Baumeister, Steve; Wiedeman, Paul E.; Traphagen, Linda; Warrior, Usha; Maring, Clarence; Kati, Warren M.; Djuric, Stevan W.; Molla, Akhteruzzaman [Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 11, p. 3173 - 3177]
[7]Location in patent: experimental part Garner, Amanda L.; Gloeckner, Christian; Tricoche, Nancy; Zakhari, Joseph S.; Samje, Moses; Cho-Ngwa, Fidelis; Lustigman, Sara; Janda, Kim D. [Journal of Medicinal Chemistry, 2011, vol. 54, # 11, p. 3963 - 3972]
[8]Gooyit, Major; Tricoche, Nancy; Lustigman, Sara; Janda, Kim D. [Journal of Medicinal Chemistry, 2014, vol. 57, # 13, p. 5792 - 5799]
[9]Wang, Shengzheng; Fang, Kun; Dong, Guoqiang; Chen, Shuqiang; Liu, Na; Miao, Zhenyuan; Yao, Jianzhong; Li, Jian; Zhang, Wannian; Sheng, Chunquan [Journal of Medicinal Chemistry, 2015, vol. 58, # 16, p. 6678 - 6696]
[10]Current Patent Assignee: SCRIPPS RESEARCH - WO2018/13890, 2018, A1 Location in patent: Page/Page column 14
[11]Current Patent Assignee: JOHNSON & JOHNSON INC - WO2008/152081, 2008, A2 Location in patent: Page/Page column 14
[12]Mondal, Santanu; Gong, Xuefeng; Zhang, Xiaoqian; Salinger, Ari J.; Zheng, Li; Sen, Sudeshna; Weerapana, Eranthie; Zhang, Xuesen; Thompson, Paul R. [Angewandte Chemie - International Edition, 2019, vol. 58, # 36, p. 12476 - 12480][Angew. Chem., 2019, vol. 131, # 36, p. 12606 - 12610,5]
[13]Current Patent Assignee: UNIVERSITY OF MASSACHUSETTS - WO2021/3078, 2021, A1 Location in patent: Paragraph 00177; 00179
[14]Krátký, Martin; Konečná, Klára; Brablíková, Michaela; Janoušek, Jiří; Pflégr, Václav; Maixnerová, Jana; Trejtnar, František; Vinšová, Jarmila [Bioorganic and Medicinal Chemistry, 2021, vol. 41]
  • 2
  • [ 133-91-5 ]
  • [ 108-24-7 ]
  • [ 36415-60-8 ]
YieldReaction ConditionsOperation in experiment
In pyridine at 20℃; for 10h;
  • 3
  • [ 133-91-5 ]
  • [ 62-53-3 ]
  • [ 19503-64-1 ]
YieldReaction ConditionsOperation in experiment
With diethyl ether
With phosphorus trichloride In toluene at 150℃; for 0.166667h; microwave irradiation;
  • 4
  • [ 69-72-7 ]
  • [ 133-91-5 ]
YieldReaction ConditionsOperation in experiment
95.9% With dihydrogen peroxide; iodine; trichloroacetic acid In methanol at 45 - 66℃; for 6h; 2 A 2L round bottom flask equipped with a mechanical stirrer, a thermometer and a condenser tube,138.1 g (1.00 mol) of salicylic acid, 261.4 g (1.03 mol) of iodine,(0.04 mol) of trichloroacetic acid was dissolved in methanol (500 ml), the temperature was raised to 45 ° C, and 175 g (1.5 mol) of 30 wt% hydrogen peroxide was added dropwise,The dropping temperature was controlled at 60-65 ° C and the dropping time was 1 hour. After the dropwise addition, the mixture was incubated at 66 ° C for 5 hours.Add water 500g, water bath to room temperature, filtration, drying that was 3,5-diiodosalic acid 374.1g, the yield of 95.9%.
95% With N-iodo-succinimide In water; acetonitrile at 25 - 30℃; for 0.333333h; General procedure for the diiodination reaction General procedure: To a solution of 4-nitroaniline, 1a (1.0 g, 7.2 mmol) and 0.01 mL water, sulfated polyborate (0.025 g, 2.5 wt%) in 7 mL anhyd. MeCN in a round bottom flask was added NIS solution (3.26 g, 14.4 mmol in 4.0 mL anhyd. MeCN) dropwise. The reaction mixture was stirred for 15 minutes at 25-30 °C, monitored by GC. After completion of the reaction, MeCN was distilled under vacuum at 40-45 °C. The residue was treated with 10 mL each of MDC and water, stirred for the mixture for 10-15 minutes; MDC layer was separated, washed with 1% sodium thiosulphate, dried over sodium sulfate, and evaporated under vacuum to obtain 2,6-diiodo-4-nitroaniline, 3a, 2.8 g (92% yield, 99% purity)
94% With N-chloro-N-(benzenesulfonyl)benzenesulfonamide; potassium iodide In N,N-dimethyl-formamide at 45 - 50℃; for 0.666667h;
91% With sodium hydrogencarbonate; N,N,N-trimethylbenzenemethanaminium dichloroiodate In methanol; dichloromethane for 7h; Ambient temperature;
91% With benzyltriphenylphosphonium dichloroiodate; sodium hydrogencarbonate In methanol; dichloromethane at 20℃; for 0.5h;
87% With sodium periodate; sulfuric acid; iodine; potassium iodide; sodium sulfite In water; acetic acid at 25℃; for 2h; Iodination of phenol (1d) in the presence of Na2SO3 (typical procedure). General procedure: Iodination of phenol (1d) in the presence of Na2SO3 (typical procedure). A 100-mL round-bottom flask was charged with a solution of 3 mmol of phenol in 10 mL of acetic acid, and a solution of KI3 and Na2SO3 (prepared preliminarily by addition of 3 mmol of iodine and 3 mmol of Na2SO3 to a solution of 3 mmol of potassium iodide in 3 mL of water) was added rapidly. At the same time, a solution of 3 mmol of NaIO4 in 5 mL of water was added, and 0.5 mL of sulfuric acid was rapidly added using a pressure-equalizing dropping funnel. The mixture was stirred at 25°C, the progress of the reaction being monitored by TLC. When the reaction was complete, the mixture was poured into ice-cold water, and the solid product was separated by vacuum filtration, washed twice with deionized water, and dried.
With carbon disulfide; iodine
With ethanol; iodine; mercury(II) oxide
With Iodine monochloride; acetic acid man verduennt das Reaktionsgemisch mit Wasser;
With ethanol; sulfuric acid; dihydrogen peroxide; iodine
With iodine; ethylenediamine; potassium iodide
With methyl N,N-dichlorocarbamate; acetic acid; sodium iodide
With sulfuric acid; mercury(II) sulfate Erwaermen des Reaktionsprodukts mit Jod in Methanol;
With iodine
With water; iodine; iodic acid

Reference: [1]Current Patent Assignee: ZHEJIANG KEYUAN CHEMICAL - CN103772080, 2016, B Location in patent: Paragraph 0040
[2]Misal, Balu; Palav, Amey; Ganwir, Prerna; Chaturbhuj, Ganesh [Tetrahedron Letters, 2021, vol. 74]
[3]Palav, Amey; Misal, Balu; Chaturbhuj, Ganesh [Journal of Organic Chemistry, 2021, vol. 86, # 17, p. 12467 - 12474]
[4]Kajigaeshi, Shoji; Kakinami, Takaaki; Yamasaki, Hiromichi; Fujisaki, Shizuo; Kondo, Manabu; Okamoto, Tsuyoshi [Chemistry Letters, 1987, p. 2109 - 2112]
[5]Location in patent: experimental part Imanieh, Hossein; Ghammamy, Shahriar; Nikje, Mir Mohammad Alavi; Hosseini, Farhang; Aghbolagh, Zahra Shokri; Fun, Hoong-Kun; Khavasi, Hamid Reza; Kia, Reza [Helvetica Chimica Acta, 2011, vol. 94, # 12, p. 2248 - 2255]
[6]Sharma; Srivastava; Agarwal; Diwedi [Russian Journal of Organic Chemistry, 2016, vol. 52, # 3, p. 433 - 436][Zh. Org. Khim., 2016, vol. 52, # 3, p. 433 - 436,4]
[7]Oechsner de Coninck; Gerard [Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1915, vol. 160, p. 628][Bulletin de la Societe Chimique de France, 1915, vol. <4> 17, p. 284]
[8]Brenans; Girod [Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1928, vol. 186, p. 1852]
[9]Cofman [Gazzetta Chimica Italiana, 1920, vol. 50 II, p. 299] Woollett; Johnson [Organic Syntheses, 1934, vol. 14, p. 52; Coll. Vol. II <1943>, 343]
[10]Jurd [Australian Journal of Scientific Research, Series A: Physical Sciences, 1950, vol. <A> 3, p. 587,590]
[11]Potts [Journal of the Chemical Society, 1953, p. 3711]
[12]Baudouin et al. [Bulletin de la Societe Chimique de France, 1954, p. 226]
[13]Ukai et al. [Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1955, vol. 75, p. 280,282][Chem.Abstr., 1956, p. 1665]
[14]Kekule [Justus Liebigs Annalen der Chemie, 1864, vol. 131, p. 223] Lautemann [Justus Liebigs Annalen der Chemie, 1861, vol. 120, p. 301]
[15]Kekule [Justus Liebigs Annalen der Chemie, 1864, vol. 131, p. 223] Demole [Chemische Berichte, 1874, vol. 7, p. 1437] Liechti [Justus Liebigs Annalen der Chemie, 1870, vol. Suppl.7, p. 150]
  • 5
  • [ 133-91-5 ]
  • [ 14056-07-6 ]
YieldReaction ConditionsOperation in experiment
With lithium aluminium tetrahydride In diethyl ether for 2h; Heating;
  • 6
  • [ 133-91-5 ]
  • [ 13862-13-0 ]
YieldReaction ConditionsOperation in experiment
With lithium aluminium tetrahydride In diethyl ether for 2h; Heating;
  • 7
  • [ 635-22-3 ]
  • [ 133-91-5 ]
  • [ 128126-92-1 ]
YieldReaction ConditionsOperation in experiment
83% With trichlorophosphate In toluene
  • 8
  • [ 1135-14-4 ]
  • [ 133-91-5 ]
  • [ 128126-94-3 ]
  • 9
  • [ 833-63-6 ]
  • [ 133-91-5 ]
  • [ 128127-05-9 ]
YieldReaction ConditionsOperation in experiment
60% With trichlorophosphate In toluene
  • 10
  • [ 5307-14-2 ]
  • [ 133-91-5 ]
  • [ 128126-84-1 ]
  • 11
  • [ 22865-52-7 ]
  • [ 133-91-5 ]
  • [ 128126-95-4 ]
YieldReaction ConditionsOperation in experiment
62% With trichlorophosphate In toluene
  • 12
  • [ 13194-68-8 ]
  • [ 133-91-5 ]
  • [ 90426-00-9 ]
YieldReaction ConditionsOperation in experiment
91% With phosphorus trichloride In xylene at 140℃; for 4h;
  • 13
  • [ 133-91-5 ]
  • [ 367-25-9 ]
  • [ 79402-06-5 ]
YieldReaction ConditionsOperation in experiment
84% With phosphorus trichloride In xylene at 140℃; for 4h;
  • 14
  • [ 133-91-5 ]
  • [ 53065-28-4 ]
  • [ 128126-87-4 ]
YieldReaction ConditionsOperation in experiment
70% With trichlorophosphate In toluene at 140℃;
  • 15
  • [ 133-91-5 ]
  • [ 52329-60-9 ]
  • [ 128126-88-5 ]
YieldReaction ConditionsOperation in experiment
58% With trichlorophosphate In toluene
  • 16
  • [ 133-91-5 ]
  • [ 106-47-8 ]
  • [ 14437-46-8 ]
YieldReaction ConditionsOperation in experiment
80% With trichlorophosphate In toluene
With phosphorus trichloride In toluene at 150℃; for 0.166667h; microwave irradiation;
Stage #1: 3,5-diiodosalicylic acid With N-ethyl-N,N-diisopropylamine; bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate In dichloromethane at 25℃; for 0.333333h; Stage #2: 4-chloro-aniline With dmap In dichloromethane at 25℃;
  • 17
  • [ 133-91-5 ]
  • [ 150-13-0 ]
  • [ 128160-32-7 ]
YieldReaction ConditionsOperation in experiment
80% With trichlorophosphate In toluene
  • 18
  • [ 133-91-5 ]
  • [ 100-01-6 ]
  • [ 19503-66-3 ]
YieldReaction ConditionsOperation in experiment
88% With trichlorophosphate In toluene
  • 19
  • [ 133-91-5 ]
  • [ 137-07-5 ]
  • [ 90481-45-1 ]
YieldReaction ConditionsOperation in experiment
90% With phosphorus trichloride In toluene for 4h; Heating;
  • 20
  • [ 133-91-5 ]
  • [ 77-78-1 ]
  • [ 121789-21-7 ]
YieldReaction ConditionsOperation in experiment
100% With potassium carbonate In acetone for 16h; Heating / reflux; 31.A [00715] Example 31. Preparation of methyl 5-(2,4-dioxo-3,4-dihydropyrimidin-l(2H)-yl)-2-methoxy-3- (6-(methylsulfonamido)naphthalen-2-yl)benzoate (compound IB-LO-2.72).[00716] ; Part A. Preparation of methyl 3,5-diiodo-2-methoxybenzoate.; [00717] A mixture of 2-hydroxy-3,5-diiodobenzoic acid (3.9g, lO.Ommol) potassium carbonate (4.15g,30.0mmol) and dimethyl sulfate (2.77g, 22.0mmol) in acetone (33ml) was heated at reflux for 16h, cooled and concentrated. The residue was dissolved in EtOAc and washed with water, brine, dried (Na2SO4), filtered and concentrated to give an off-white solid (4.2g, quantitative yield).
96% With potassium carbonate In acetone for 6h; Heating;
95% With potassium carbonate Inert atmosphere;
93% With potassium carbonate In acetone for 12h; Heating;
With potassium carbonate In acetone Heating; Yield given;

  • 21
  • [ 133-91-5 ]
  • [ 94-09-7 ]
  • [ 128126-93-2 ]
YieldReaction ConditionsOperation in experiment
75% With trichlorophosphate In toluene
  • 22
  • [ 133-91-5 ]
  • [ 101-79-1 ]
  • [ 128126-96-5 ]
  • 23
  • [ 100-97-0 ]
  • [ 119-30-2 ]
  • [ 133-91-5 ]
  • [ 685870-21-7 ]
YieldReaction ConditionsOperation in experiment
Stage #1: hexamethylenetetramine; 2-hydroxy-5-iodobenzoic acid With trifluoroacetic acid at 90℃; Stage #2: With hydrogenchloride for 5h; Title compound not separated from byproducts;
  • 24
  • [ 133-91-5 ]
  • 3,5-diiodo-2-hydroxy-N-(3-phenylsulfonylphenyl)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: phosphorus trichloride / chlorobenzene / 0.5 h / Heating 2: 58 percent / chlorobenzene / 5 h / Heating
  • 25
  • [ 133-91-5 ]
  • 3,5-diiodo-2-hydroxy-N-((4-chloro-3-phenylsulfonyl)phenyl)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: phosphorus trichloride / chlorobenzene / 0.5 h / Heating 2: 49 percent / chlorobenzene / 5 h / Heating
  • 26
  • [ 133-91-5 ]
  • 3,5-diiodo-2-hydroxy-N-(3-(4-chlorophenylsulfonyl)phenyl)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: phosphorus trichloride / chlorobenzene / 0.5 h / Heating 2: 52 percent / chlorobenzene / 5 h / Heating
  • 27
  • [ 133-91-5 ]
  • 2-hydroxy-3,5-diiodo-N-[2-(diethylamino)ethyl]benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: SOCl2 / 0.67 h / 120 °C 2: 8.0 g / dioxane / 1 h / 20 °C
  • 28
  • [ 133-91-5 ]
  • [ 90272-02-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: pyridine / 10 h / 20 °C 2: SOCl2; urea / toluene / 3 h / 100 - 110 °C
  • 29
  • [ 133-91-5 ]
  • [ 367526-65-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: pyridine / 10 h / 20 °C 2.1: SOCl2; urea / toluene / 3 h / 100 - 110 °C 3.1: Mg; EtOH / CCl4; toluene / 1 h / Heating 3.2: CCl4; toluene / 0.5 h / 20 °C
  • 31
  • [ 133-91-5 ]
  • N-[5-chloro-4-(4-chlorobenzoyl)-2-methylphenyl]-3,5-diiodo-2-hydroxybenzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: SOCl2, DMF / benzene / 1 h / 60 °C 2: dioxane / 1 h / 50 °C
  • 33
  • [ 133-91-5 ]
  • N-{4-[2-amino-1-(4-chlorophenyl)ethyl]-5-chloro-2-methylphenyl}-3,5-diiodo-2-hydroxybenzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: SOCl2, DMF / benzene / 1 h / 60 °C 2: dioxane / 1 h / 50 °C 3: TFA, anisole / CH2Cl2 / 0.5 h
  • 34
  • [ 133-91-5 ]
  • [ 97028-79-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: POCl3 / toluene 2: 60 percent / H2 / Raney nickel / ethanol / 1838.8 Torr 3: 75 percent / aq. HCl / 6 h / Heating
  • 35
  • [ 133-91-5 ]
  • [ 128126-90-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: POCl3 / toluene 2: 60 percent / H2 / Raney nickel / ethanol / 1838.8 Torr
  • 36
  • [ 133-91-5 ]
  • 2,4-Diiodobenzimidazo<2,3-b>-1,3-benzoxazin-11-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: POCl3 / toluene 2: 60 percent / H2 / Raney nickel / ethanol / 1838.8 Torr 3: 70 percent / Et3N / acetone / 4 h / Heating
  • 37
  • [ 133-91-5 ]
  • [ 128126-85-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 83 percent / POCl3 / toluene 2: 80 percent / NH3 / H2O / 36 h / 140 °C 3: 55 percent / H2 / Raney nickel / ethanol / 12 h / 1838.8 Torr
Multi-step reaction with 2 steps 1: 75 percent / POCl3 / toluene / 8 h / 140 °C 2: 55 percent / H2 / Raney nickel / ethanol / 12 h / 1838.8 Torr
  • 38
  • [ 133-91-5 ]
  • [ 128127-03-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 80 percent / POCl3 / toluene 2: 70 percent / tetrahydrofuran
  • 39
  • [ 133-91-5 ]
  • [ 128126-84-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 83 percent / POCl3 / toluene 2: 80 percent / NH3 / H2O / 36 h / 140 °C
  • 40
  • [ 133-91-5 ]
  • [ 128127-06-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 60 percent / POCl3 / toluene 2: 55 percent / H2 / Raney nickel / ethanol / 1838.8 Torr
  • 41
  • [ 133-91-5 ]
  • [ 128127-07-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 60 percent / POCl3 / toluene 2: 55 percent / H2 / Raney nickel / ethanol / 1838.8 Torr 3: 75 percent / acetone / 6 h / Heating
  • 42
  • [ 133-91-5 ]
  • [ 128127-10-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 60 percent / POCl3 / toluene 2: 55 percent / H2 / Raney nickel / ethanol / 1838.8 Torr 3: 59 percent / acetone
  • 43
  • [ 133-91-5 ]
  • [ 128126-86-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 83 percent / POCl3 / toluene 2: 80 percent / NH3 / H2O / 36 h / 140 °C 3: 55 percent / H2 / Raney nickel / ethanol / 12 h / 1838.8 Torr 4: 50 percent / ethanol / 24 h / Heating
Multi-step reaction with 3 steps 1: 75 percent / POCl3 / toluene / 8 h / 140 °C 2: 55 percent / H2 / Raney nickel / ethanol / 12 h / 1838.8 Torr 3: 50 percent / ethanol / 24 h / Heating
  • 44
  • [ 133-91-5 ]
  • [ 128127-08-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 60 percent / POCl3 / toluene 2: 55 percent / H2 / Raney nickel / ethanol / 1838.8 Torr 3: 60 percent / acetone / 2 h / Ambient temperature
  • 45
  • [ 133-91-5 ]
  • [ 128127-09-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 60 percent / POCl3 / toluene 2: 55 percent / H2 / Raney nickel / ethanol / 1838.8 Torr 3: 55 percent / acetone
  • 46
  • [ 133-91-5 ]
  • [ 439107-30-9 ]
YieldReaction ConditionsOperation in experiment
26% With diphenylphosphoranyl azide; triethylamine In methanol; water; ethyl acetate; SiO2; toluene 3.59 5,7-Diiodo-3H-benzooxazol-2one (92LH49) 3.59 5,7-Diiodo-3H-benzooxazol-2one (92LH49) A 4 ml vial was charged with 2-hydroxy-3,5-diiodobenzoic acid (0.780 g, 2.00 mmol), diphenylphosphoryl azide (0.202 g, 1.99 mmol), triethylamine (0.550 g, 2.00 mmol), and toluene (4 ml). The mixture was shaken at 110° under an Argon atmosphere for 20 h. The reaction mixture was cooled to r.t., water added (1 ml), and the product was extracted into ethyl acetate (2*1 ml). The combined org. layer was concentrated in vacuo before being purified twice by flash CC (SiO2; DCM/MeOH 9:1 and then n-heptan/EtOAc 1:1) to give the title compound (92LH49) (0.205 g, 26%). 1-NMR (DMSO) δ7.34-7.32 (m, 1 H), 7.71-7.70 (m, 1 H), 11.96 (br. s, 1 H); 13C-NMR (DMSO) δ75.3, 88.0, 117.7, 131.6, 136.8, 144.9, 152.6.
26% With diphenylphosphoranyl azide; triethylamine In methanol; water; ethyl acetate; SiO2; toluene 3 Synthetic Procedures 3.59 5,7-Diiodo-3H-benzooxazol-2one (92LH49) A 4 ml vial was charged with 2-hydroxy-3,5-diiodobenzoic acid (0.780 g, 2.00 mmol), diphenylphosphoryl azide (0.202 g, 1.99 mmol), triethylamine (0.550 g, 2.00 mmol), and toluene (4 ml). The mixture was shaken at 110° under an Argon atmosphere for 20 h. The reaction mixture was cooled to r.t., water added (1 ml), and the product was extracted into ethyl acetate (2*1 ml). The combined org. layer was concentrated in vacuo before being purified twice by flash CC (SiO2; DCM/MeOH 9:1 and then n-heptan/EtOAc 1:1) to give the title compound (92LH49) (0.205 g, 26%). 1-NMR (DMSO) δ 7.34-7.32 (m, 1H), 7.71-7.70 (m, 1H), 11.96 (br. s, 1H); 13C-NMR (DMSO) δ 75.3, 88.0, 117.7, 131.6, 136.8, 144.9, 152.6.
26% With diphenylphosphoranyl azide; triethylamine In toluene at 110℃; for 20h; 3.59 3.59 5,7-Diiodo-3H-benzooxazol-2one (92LH49) 3.59 5,7-Diiodo-3H-benzooxazol-2one (92LH49) A 4 ml vial was charged with 2-hydroxy-3,5-diiodobenzoic acid (0.780 g, 2.00 mmol), diphenylphosphoryl azide (0.202 g, 1.99 mmol), triethylamine (0.550 g, 2.00 mmol), and toluene (4 ml). The mixture was shaken at 110° under an Argon atmosphere for 20 h. The reaction mixture was cooled to r.t., water added (1 ml), and the product was extracted into ethyl acetate (2*1 ml). The combined org. layer was concentrated in vacuo before being purified twice by flash CC (SiO2; DCM/MeOH 9:1 and then n-heptan/EtOAc 1:1) to give the title compound (92LH49) (0.205 g, 26%). 1-NMR (DMSO) δ 7.34-7.32 (m, 1H), 7.71-7.70 (m, 1H), 11.96 (br. s, 1H); 13C-NMR (DMSO) δ 75.3, 88.0, 117.7, 131.6, 136.8, 144.9, 152.6.
  • 47
  • 1-(4-aminophenyl)-1-phenylethylene hydrochloride [ No CAS ]
  • [ 60-29-7 ]
  • [ 133-91-5 ]
  • [ 99-92-3 ]
  • [ 873-77-8 ]
  • N-[4-[1-(4-chlorophenyl)-ethenyl]phenyl]-2-hydroxy-3,5-diiodobenzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; anhydrous phosphorus trichloride In ethanol; dichloromethane; chlorobenzene 2 EXAMPLE 2 EXAMPLE 2 A mixture of 400 ml of ethyl ether containing 0.5 mole of 4-chlorophenylmagnesium bromide was added over 1 hour to a mixture of 13.5 g of 4-aminoacetophenone in 500 ml of ether under nitrogen. After heating at reflux for 3 hours, the cooled mixture was quenched with 250 ml of saturated ammonium chloride solution. The dried ethereal layer was evaporated. The residual oil was mixed with 250 ml of 3N hydrochloric acid. After heating on the steam bath for 3 hours, the cooled mixture was separated from a soft solid. The product was taken up in 100 ml of ethanol. Ether (600 ml) was added to give a solid, 14.3 g of 1-(4-aminophenyl)-1-phenylethylene hydrochloride, m.p. 181°-183°. A mixture of 5.06 g (0.013 mole) of 3,5-diiodosalicylic acid and 3.5 g (0.013 mole) of the amine salt in 125 ml of chlorobenzene was heated at reflux. Phosphorus trichloride (1.5 ml) was added over 45 minutes. After heating at reflux for 2 hours, the mixture was cooled and stripped to give a residue. The solid was extracted with 250 ml of methylene chloride and filtered through a filter aid. The extract was washed, dried and evaporated. The residue, in methylene chloride, was passed over a silica gel column with a methylene chloride/n-hexane eluant to give 2.23 g of white solid; N-[4-[1-(4-chlorophenyl)-ethenyl]phenyl]-2-hydroxy-3,5-diiodobenzamide, m.p. 181°-184°. Anal. Calcd. for C21 H14 ClI2 NO2: C, 41.93; H, 2.35; N, 2.33. Found: C, 41.81; H, 2.71; N, 2.23.
  • 48
  • [ 133-91-5 ]
  • [ 46407-51-6 ]
  • N-[4-(1-phenylethenyl)phenyl]-2-hydroxy-3,5-diiodobenzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With anhydrous phosphorus trichloride In dichloromethane; water; chlorobenzene 5 EXAMPLE 5 EXAMPLE 5 To a refluxing solution of 7.9 g (0.02 mole) of 3,5-diiodosalicylic acid and 4.6 g (0.02 mole) of 1-(4-aminophenyl)-1-phenylethylene in 125 ml of chlorobenzene was added 3 g (0.022 mole) of phosphorus trichloride over a 1 hour period. The resulting mixture was refluxed for 2 hours, cooled, diluted with 100 ml of methylene chloride. The organic phase was washed with 250 ml of water and dried. The extract was evaporated to dryness. After redissolving the residue in minimum amount of methylene chloride, the solution was flash-chromatographed on a silica gel column. The desired component was eluted with 2 liters of methylene chloride/n-hexane. Evaporation of its solvent gave 4.9 g of N-[4-(1-phenylethenyl)phenyl] -2-hydroxy-3,5-diiodobenzamide. Recrystallization from aqueous ethanol gave 4.2 g of purified product, m.p. 173°-174°.
  • 49
  • 1-(4-amino-2-chloro-6-methylphenyl)-1-(4-chlorophenyl)ethylene [ No CAS ]
  • [ 133-91-5 ]
  • N-[3-chloro-5-methyl-4-[1-(4-chlorophenyl)ethenyl]phenyl]-3,5-diiodo-2-hydroxybenzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
6 EXAMPLE 6 EXAMPLE 6 Using the reaction sequence of Example 4, 3,5-diiodosalicylic acid is reacted with 1-(4-amino-2-chloro-6-methylphenyl)-1-(4-chlorophenyl)ethylene in the presence of phosphorus trichloride to give N-[3-chloro-5-methyl-4-[1-(4-chlorophenyl)ethenyl]phenyl]-3,5-diiodo-2-hydroxybenzamide.
  • 50
  • [ 769-92-6 ]
  • [ 133-91-5 ]
  • C17H17I2NO2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With phosphorus trichloride In toluene at 150℃; for 0.166667h; microwave irradiation;
  • 51
  • [ 372-16-7 ]
  • [ 133-91-5 ]
  • C14H8F3I2NO2S [ No CAS ]
  • 52
  • [ 133-91-5 ]
  • [ 2106-05-0 ]
  • C13H7ClFI2NO2 [ No CAS ]
  • 53
  • [ 133-91-5 ]
  • [ 37529-27-4 ]
  • C20H23I2NO2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With phosphorus trichloride In toluene at 150℃; for 0.166667h; microwave irradiation;
  • 54
  • [ 133-91-5 ]
  • [ 371-40-4 ]
  • [ 79402-05-4 ]
YieldReaction ConditionsOperation in experiment
With phosphorus trichloride In toluene at 150℃; for 0.166667h; microwave irradiation;
  • 55
  • [ 133-91-5 ]
  • [ 106-40-1 ]
  • [ 14437-47-9 ]
YieldReaction ConditionsOperation in experiment
With phosphorus trichloride In toluene at 150℃; for 0.166667h; microwave irradiation;
  • 56
  • [ 133-91-5 ]
  • [ 6376-14-3 ]
  • [ 1000397-73-8 ]
YieldReaction ConditionsOperation in experiment
With phosphorus trichloride In toluene at 150℃; for 0.166667h; microwave irradiation;
  • 57
  • Iron(III) nitrate nonahydrate [ No CAS ]
  • [ 133-91-5 ]
  • Fe(3,5-diiodosalicylate)3*2.5H2O [ No CAS ]
YieldReaction ConditionsOperation in experiment
35% With NaOH In water addn. of Fe-salt in water to filtered soln. of acid in hot water and NaOH;; filtration; washing; elem. anal.;
  • 58
  • [Na4(cucurbituril)2(H2O)16]Cl4/water (1/6) [ No CAS ]
  • [ 84-88-8 ]
  • [ 133-91-5 ]
  • [ 7647-14-5 ]
  • copper dichloride [ No CAS ]
  • [Na2(cucurbituril)(H2O)2][copper(II)(3,5-diiodosalicylate)(8-hydroxyquinoline-5-sulfonate)]/water (1/6.5) [ No CAS ]
YieldReaction ConditionsOperation in experiment
40% In water (C72H104N48Na4O40)Cl4*6H2O dissolved in aq. soln. of NaCl; added dropwise to aq. mixt. of CuCl2, I2C6H2(OH)CO2H, and C9H5N(OH)(SO3H) at pH 6 under stirring; further educt: H2O; filtered, slowly evapd. over 2 wk; elem. anal.;
  • 60
  • [ 133-91-5 ]
  • [ 95-79-4 ]
  • [ 100462-85-9 ]
YieldReaction ConditionsOperation in experiment
Stage #1: 3,5-diiodosalicylic acid With N-ethyl-N,N-diisopropylamine; bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate In dichloromethane at 25℃; for 0.333333h; Stage #2: 5-chloro-2-methyl-benzenamine With dmap In dichloromethane at 25℃;
  • 61
  • [ 133-91-5 ]
  • [ 30575-42-9 ]
  • [ 1194667-44-1 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate In N,N-dimethyl-formamide at 70 - 80℃;
  • 63
  • [ 133-91-5 ]
  • methyl 2-methoxy-5-(1,1,2,2,3,3,4,4,5,5,6,6,6-tridecafluorohexyl)benzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium carbonate / Inert atmosphere 2: copper; [2,2]bipyridinyl / dimethyl sulfoxide; Hexafluorobenzene / 72 h / 80 °C / Inert atmosphere; Schlenk technique
Multi-step reaction with 3 steps 1: potassium carbonate / Inert atmosphere 2: copper; [2,2]bipyridinyl / dimethyl sulfoxide; Hexafluorobenzene / 72 h / 80 °C / Inert atmosphere; Schlenk technique 3: copper; [2,2]bipyridinyl / dimethyl sulfoxide; Hexafluorobenzene / 72 h / 80 °C / Inert atmosphere; Schlenk technique
  • 64
  • [ 133-91-5 ]
  • 2-methoxy-5-(1,1,2,2,3,3,4,4,5,5,6,6,6-tridecafluorohexyl)benzyl alcohol [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: potassium carbonate / Inert atmosphere 2: copper; [2,2]bipyridinyl / dimethyl sulfoxide; Hexafluorobenzene / 72 h / 80 °C / Inert atmosphere; Schlenk technique 3: lithium aluminium tetrahydride / diethyl ether / 0.5 h / 0 °C / Inert atmosphere
Multi-step reaction with 4 steps 1: potassium carbonate / Inert atmosphere 2: copper; [2,2]bipyridinyl / dimethyl sulfoxide; Hexafluorobenzene / 72 h / 80 °C / Inert atmosphere; Schlenk technique 3: copper; [2,2]bipyridinyl / dimethyl sulfoxide; Hexafluorobenzene / 72 h / 80 °C / Inert atmosphere; Schlenk technique 4: lithium aluminium tetrahydride / diethyl ether / 0.5 h / 0 °C / Inert atmosphere
  • 65
  • [ 133-91-5 ]
  • [ 19094-55-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: potassium carbonate / acetone / 3 h / 20 °C / Inert atmosphere 2.1: potassium hydroxide / water; methanol / Inert atmosphere; Reflux 2.2: Inert atmosphere
Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 12 h / 90 °C 2: lithium hydroxide / tetrahydrofuran; methanol; water / 2 h / 25 °C
Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 12 h / 90 °C / Sealed tube 2: lithium hydroxide; water / tetrahydrofuran; methanol / 2 h / 25 °C
  • 66
  • [ 133-91-5 ]
  • [ 74-88-4 ]
  • [ 121789-21-7 ]
YieldReaction ConditionsOperation in experiment
89% With potassium hydroxide In N,N-dimethyl-formamide at 0 - 20℃; Inert atmosphere; Synthesis of methyl 3,5-diiodo-2-methoxybenzoate (2d) 3,5-Diiodosalicylic acid (3.90 g, 10.0 mmol) was dissolved in DMF (20 mL). KOH (1.68 g, 30 mmol) and MeI (1.9 mL) were added at 0 °C and the reaction solution was allowed to warm to room temperature overnight. After work-up, the crude product was purified via column chromatography (isohexane, Rf = 0.57) to give the product 2d (3.73 g, 8.92 mmol, 89%) as a white solid. M.p. (°C): 83-85. 1H-NMR (400 MHz, CDCl3, ppm) δ = 8.24 (d, J = 2.2 Hz, 1H), 8.07 (d, J = 2.2 Hz, 1H), 3.92(s, 3H), 3.87 (s, 3H). 13C-NMR (101 MHz, CDCl3, ppm) δ = 166.6, 156.1, 140.9, 132.2, 129.3, 126.0, 85.5, 62.7,14.3. IR (ATR, cm-1) ν = 2944, 1728, 1410, 1273, 1206, 990. MS (EI, 70 eV, %) m/z = 418 (55), 389 (100), 387 (44), 386 (16), 385 (75), 372 (17), 357 (19),343 (71), 276 (17), 262 (28), 260 (18), 245 (50), 217 (71), 189 (34), 76 (11). HRMS (EI, 70 eV) m/z: calc. for C9H8I2O3: 417.8563; found: 417.8593.
With potassium carbonate In acetone at 20℃; for 3h; Inert atmosphere;
With potassium carbonate In N,N-dimethyl-formamide at 90℃; for 12h;
With potassium carbonate In N,N-dimethyl-formamide at 90℃; for 12h; Sealed tube; Synthesis of 27. Methyl iodide (0.18 mL, 2.9 mmol) was added dropwise to a suspension of 3,5- diiodosalicylic acid (DISA) (0.5 g, 1.3 mmol) and potassium carbonate (0.45 g, 3.3 mmol) in anhydrous DMF. The mixture was heated in a sealed tube at 90 °C for 12 h followed by pouring into water to precipitate compound 26, which was recovered by vacuum filtration, washed with water and dried in vacuo. Crude compound 26 (0.22 g, 0.53 mmol) was then dissolved in 1 : 1 THF/MeOH (10 mL) and was treated with 1 M aqueous lithium hydroxide solution (5.3 mL). The mixture was allowed to stir for 2 h at 25 °C and the organic solvents were removed under reduced pressure. The mixture was then acidified with 2 M aqueous hydrochloric acid and was extracted twice with excess diethyl ether. The combined ether extracts were washed with water, dried over anhydrous sodium sulphate and concentrated in vacuo to afford 27 as an off-white solid. Crude 27 was purified by column chromatography using hexane/ethyl acetate as the eluent and was characterized by 'H, 13C NMR spectroscopy and mass spectrometry. Overall yield: 60%.

  • 67
  • [ 4894-26-2 ]
  • [ 133-91-5 ]
  • 1,3-diiodo-7,8,13,13b-tetrahydro-5H-benzo[5',6'][1,3]oxazino[3',2':1,2]pyrido[3,4-b]indol-5-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
52% In dichloromethane at 20℃; for 12h;
  • 68
  • [ 133-91-5 ]
  • [ 22706-11-2 ]
  • 2,4-diiodo-6-(3-phenyl-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazol-6yl)phenol [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% With trichlorophosphate In N,N-dimethyl-formamide for 10h; Reflux;
  • 69
  • [ 133-91-5 ]
  • [ 22706-11-2 ]
  • 2-hydroxy-3,5-diiodo-N-(3-phenyl-5-thioxo-1H-1,2,4-triazol-4(5H)-yl)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
84% Stage #1: 3,5-diiodosalicylic acid With benzotriazol-1-ol; 1,2-dichloro-ethane In N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: 3-phenyl-4-amino-5-mercapto-1,2,4-triazole In N,N-dimethyl-formamide for 2h;
  • 70
  • [ 133-91-5 ]
  • [ 107-07-3 ]
  • [ 75-50-3 ]
  • C12H16Cl2NO3(1+)*Cl(1-) [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 3,5-diiodosalicylic acid With oxalyl dichloride In tetrahydrofuran at 4℃; for 4h; Inert atmosphere; Stage #2: 2-chloro-ethanol at 30℃; for 10h; Stage #3: trimethylamine In tetrahydrofuran at 20℃; 2 Preparation of choline chloride (2-hydroxy-3,5-dichlorophenyl)carboxylate 2 g of 2-hydroxy-3,5-diiodobenzoic acid was placed in a 100 ml three-necked flask, dissolved in 10 ml of THF', protected with N2, and stirred.7.4 g of oxalyl chloride was added dropwise at 4 ° C, and the reaction was stirred for 4 hours. Evaporate to dryness under reduced pressure.Add 10 ml of 2-chloroethanol to the residue and stir at 30 ° CThe reaction was stirred for 10 hours and evaporated to dryness under reduced pressure.The residue was dissolved in 40 ml of THF, and 12 ml of a 2M trimethylamine THF solution was added thereto, and the mixture was stirred at room temperature to precipitate a solid, which was filtered and dried.
  • 71
  • [ 133-91-5 ]
  • [ 1093097-72-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: oxalic acid / N,N-dimethyl-formamide / dichloromethane / 3 h / 20 °C 2: 1,4-dioxane
  • 72
  • [ 133-91-5 ]
  • [ 1093097-71-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: oxalic acid / N,N-dimethyl-formamide / dichloromethane / 3 h / 20 °C 2: 1,4-dioxane
  • 73
  • [ 24900-79-6 ]
  • [ 133-91-5 ]
  • [ 22662-39-1 ]
  • 74
  • [ 24900-79-6 ]
  • [ 133-91-5 ]
  • C19H13Cl2I2NO2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; benzotriazol-1-ol / dichloromethane / 14 h / 20 °C 2.1: tris(pentafluorophenyl)borate; methylphenylsilane / toluene / 25 h / 27 - 50 °C / Inert atmosphere; Sealed tube 2.2: 1 h / 0 - 27 °C / Inert atmosphere; Sealed tube
  • 75
  • [ 133-91-5 ]
  • C20H20FI2N5O2*C2HF3O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: thionyl chloride; N,N-dimethyl-formamide / dichloromethane / 6 h / Reflux 2: triethylamine / tetrahydrofuran; water / 12 h / 25 °C 3: dichloromethane / 1 h / 25 °C 4: triethylamine / methanol / 4 h / 25 °C
Multi-step reaction with 4 steps 1: thionyl chloride; N,N-dimethyl-formamide / dichloromethane / 6 h / 60 °C 2: triethylamine / tetrahydrofuran; water / 12 h / 25 °C 3: dichloromethane / 1 h / 20 °C 4: triethylamine / methanol / 4 h / 25 °C
  • 76
  • [ 133-91-5 ]
  • C18H18I2N4O2*C2HF3O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: thionyl chloride; N,N-dimethyl-formamide / dichloromethane / 6 h / Reflux 2: triethylamine / tetrahydrofuran; water / 12 h / 25 °C 3: dichloromethane / 1 h / 25 °C
Multi-step reaction with 3 steps 1: thionyl chloride; N,N-dimethyl-formamide / dichloromethane / 6 h / 60 °C 2: triethylamine / tetrahydrofuran; water / 12 h / 25 °C 3: dichloromethane / 1 h / 20 °C
  • 77
  • [ 1635-31-0 ]
  • [ 133-91-5 ]
  • 2-hydroxy-3,5-diiodo-N-(2-oxo-2H-chromen-3-yl)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% With phosphorus trichloride In acetonitrile Reflux; 4.1.3 General procedure for the synthesis of compounds 5a-p General procedure: The 3-aminocoumarin 3 (1mmol) and appropriate carboxylic acid 4a-p (1.1mmol) were dissolved in 3mL CH3CN and the mixture was stirred at room temperature for half an hour. The PCl3 (1mmol) was added dropwise in the reaction mixture and the reaction mixture was again refluxed for 5-6h but in case of compounds 5c and 5p 8h refluxing was required. After completion the reaction was quenched by adding ice cold water (5mL) and the solvent was evaporated under reduced pressure. The residue was dissolved in chloroform (10mL) and washed twice with water (2×20mL) and then with saturated NaHCO3 solution (10mL) and finally with brine (20mL). The organic layer was dried over Na2SO4 and the solvent was evaporated under vacuum. The solid products obtained in case of compounds 5a, 5b, 5d, 5f, 5h, and 5p were recrystallized from acetone while those in case of compounds 5c, 5i and 5l were recrystallized in acetone and DMSO mixture (3:1). The crude products obtained in case of compounds 5e, 5g, 5j, 5k and 5m-5o were purified by silica gel column using chloroform:methanol (9:1) as eluent.
  • 78
  • [ 69-72-7 ]
  • [ 119-30-2 ]
  • [ 520-79-6 ]
  • [ 133-91-5 ]
YieldReaction ConditionsOperation in experiment
General procedure: To a solution of 4-fluoro-2-hydroxybenzoic acid (780.6 mg, 5 mmol) in MeCN (10 mL) was added con. H2SO4 (285 muL, 1.05 equiv.) at room temperature, the mixture was stirred for 5 min. Then, NBS (934.4 mg, 1.05 equiv.) was added to the mixture. The reaction was monitored using TLC analysis. The mixture was evaporated to dryness and MeCN (1 mL) was added to the flask. The mixture was stirred for 10 min and filtered. The filter cake was washed by water and dried to obtain the product as a white solid; yield: 85% (0.99 g).
  • 79
  • [ 504-15-4 ]
  • [ 133-91-5 ]
  • [ 39156-34-8 ]
YieldReaction ConditionsOperation in experiment
55% With methanesulfonic acid; phosphorus pentoxide at 90℃; 3.2. General procedure for preparation of substituted 1-hydroxy-3-methylxanthones General procedure: A mixture of phosphorus pentoxide (0.36 g, 2.5 mmol) and methanesulfonic acid(10 ml) was heated at 110 C until a clear solution was obtained. The temperature wasthen lowered to 90 C and a mixture of 3,5-dihydroxytoluene (0.13 g, 1.0 mmol) andsubstituted salicylic acid (1.0 mmol) was added. Heating was then continued for severalhours. The reaction progress was monitored by thin-layer chromatography (TLC)until the reaction was balanced, then the reaction mixture was poured into icedwater.The crude product was collected by filtration or extracted with ethyl acetate,washed with water, dried, and purified by medium pressure preparative chromatographywith ethyl acetate/petroleum ether to afford the target xanthone.
  • 80
  • [ 108-99-6 ]
  • zinc(II) nitrate hexahydrate [ No CAS ]
  • [ 133-91-5 ]
  • [(3-methylpyridine)2Zn(3,5-iodosalicylate)2] [ No CAS ]
YieldReaction ConditionsOperation in experiment
79% In ethanol Preparation of 1-5 General procedure: 70 mg (0.18 mmol) of DISA were dissolvedin 3 ml of ethanol, followed by addition of 0.36 mmol of corresponding substituted pyridine (35, 35, 40, 41 or 35 μl, respectively), and mixed with solution of Zn(NO3)2*6H2O (27 mg,0.09 mmol) in 3 ml of ethanol. In all cases, slow evaporation of solvent results in formation of colorless crystals of 1-5. The yields and element analysis data are given in SI (Table S2).
  • 81
  • [ 108-89-4 ]
  • zinc(II) nitrate hexahydrate [ No CAS ]
  • [ 133-91-5 ]
  • [(4-methylpyridine)2Zn(3,5-iodosalicylate)2] [ No CAS ]
YieldReaction ConditionsOperation in experiment
83% In ethanol Preparation of 1-5 General procedure: 70 mg (0.18 mmol) of DISA were dissolvedin 3 ml of ethanol, followed by addition of 0.36 mmol of corresponding substituted pyridine (35, 35, 40, 41 or 35 μl, respectively), and mixed with solution of Zn(NO3)2*6H2O (27 mg,0.09 mmol) in 3 ml of ethanol. In all cases, slow evaporation of solvent results in formation of colorless crystals of 1-5. The yields and element analysis data are given in SI (Table S2).
  • 82
  • [ 591-22-0 ]
  • zinc(II) nitrate hexahydrate [ No CAS ]
  • [ 133-91-5 ]
  • [(3,5-dimethylpyridine)2Zn(3,5-iodosalicylate)2] [ No CAS ]
YieldReaction ConditionsOperation in experiment
83% In ethanol Preparation of 1-5 General procedure: 70 mg (0.18 mmol) of DISA were dissolvedin 3 ml of ethanol, followed by addition of 0.36 mmol of corresponding substituted pyridine (35, 35, 40, 41 or 35 μl, respectively), and mixed with solution of Zn(NO3)2*6H2O (27 mg,0.09 mmol) in 3 ml of ethanol. In all cases, slow evaporation of solvent results in formation of colorless crystals of 1-5. The yields and element analysis data are given in SI (Table S2).
  • 83
  • [ 583-58-4 ]
  • zinc(II) nitrate hexahydrate [ No CAS ]
  • [ 133-91-5 ]
  • [(3,4-dimethylpyridine)2Zn(3,5-iodosalicylate)2] [ No CAS ]
YieldReaction ConditionsOperation in experiment
87% In ethanol Preparation of 1-5 General procedure: 70 mg (0.18 mmol) of DISA were dissolvedin 3 ml of ethanol, followed by addition of 0.36 mmol of corresponding substituted pyridine (35, 35, 40, 41 or 35 μl, respectively), and mixed with solution of Zn(NO3)2*6H2O (27 mg,0.09 mmol) in 3 ml of ethanol. In all cases, slow evaporation of solvent results in formation of colorless crystals of 1-5. The yields and element analysis data are given in SI (Table S2).
  • 84
  • [ 626-55-1 ]
  • zinc(II) nitrate hexahydrate [ No CAS ]
  • [ 133-91-5 ]
  • [(3-bromopyridine)2Zn(3,5-iodosalicylate)2] [ No CAS ]
YieldReaction ConditionsOperation in experiment
87% In ethanol Preparation of 1-5 General procedure: 70 mg (0.18 mmol) of DISA were dissolvedin 3 ml of ethanol, followed by addition of 0.36 mmol of corresponding substituted pyridine (35, 35, 40, 41 or 35 μl, respectively), and mixed with solution of Zn(NO3)2*6H2O (27 mg,0.09 mmol) in 3 ml of ethanol. In all cases, slow evaporation of solvent results in formation of colorless crystals of 1-5. The yields and element analysis data are given in SI (Table S2).
  • 85
  • [ 133-91-5 ]
  • [ 541-41-3 ]
  • C10H8I2O5 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 3,5-diiodosalicylic acid With triethylamine In acetone at 0℃; for 0.25h; Stage #2: chloroformic acid ethyl ester In acetone for 1h; General procedure: Appropriate carboxylic acid, (0.01 mol) was dissolved in anhydrousacetone (50 mL) and triethylamine (1.42 mL, 0.01 mol). After 15 min at0 °C, ethyl chloroformate (0.97 mL, 0.01 mol) was added dropwise andthe reaction was kept for 60 min, followed by addition of 4-(2-aminoethyl)-N-(cyclohexylcarbamoyl)benzenesulfonamide (4) (3.25 g,0.01 mol) and triethylamine (1.42 mL, 0.01 mol) in anhydrous acetone(20 mL). The resulting mixture was stirred for 4 h at room temperature.Acetone was removed under reduced pressure, and the residue wasacidified with 5% HCl to pH ≈ 5. White solid product was collected andwashed with water and dried at 65 °C.
  • 86
  • [ 133-91-5 ]
  • [ 36209-50-4 ]
  • 2,4-diiodo-6-(3-(4-nitrophenyl)-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazol-6-yl)phenol [ No CAS ]
YieldReaction ConditionsOperation in experiment
With trichlorophosphate at 80℃; for 8h;
  • 87
  • [ 133-91-5 ]
  • [ 87239-96-1 ]
  • 2-(3-(3-bromophenyl)-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazol-6-yl)-4,6-diiodophenol [ No CAS ]
YieldReaction ConditionsOperation in experiment
With trichlorophosphate at 80℃; for 8h;
  • 88
  • [ 133-91-5 ]
  • [ 117320-66-8 ]
  • 2-(3-(3-chlorophenyl)-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazol-6-yl)-4,6-diiodophenol [ No CAS ]
YieldReaction ConditionsOperation in experiment
With trichlorophosphate at 80℃; for 8h;
  • 89
  • [ 133-91-5 ]
  • [ 68468-95-1 ]
  • 2,4-diiodo-6-(3-(4-chlorophenyl)-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazol-6-yl)phenol [ No CAS ]
YieldReaction ConditionsOperation in experiment
With trichlorophosphate at 80℃; for 8h;
  • 90
  • [ 133-91-5 ]
  • [ 13229-01-1 ]
  • 2,4-diiodo-6-(3-(p-tolyl)-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazol-6-yl)phenol [ No CAS ]
YieldReaction ConditionsOperation in experiment
With trichlorophosphate at 80℃; for 8h;
  • 91
  • [ 133-91-5 ]
  • C28H30NO2(1+) [ No CAS ]
  • C35H33INO5(1+) [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine In N,N-dimethyl-formamide at 85℃; for 10h; Inert atmosphere; 1 Example 1 Compound 1 (1mmol) was added to a round-bottom flask, and N,N-dimethylformamide (13mL) was slowly added under the protection of nitrogen. After stirring until completely dissolved, under the protection of nitrogen, triethylamine ( 4mmol), continue to stir for 15min, slowly add 3,5-diiodosalicylic acid (4mmol) under the protection of nitrogen, and stir until completely dissolved. The above system is stirred and heated to 85°C in an oil bath, and reacted for 10 hours. After the solution turns dark blue, cool the system, pour the reaction liquid in the round bottom flask into a separatory funnel and add dichloromethane and distilled water , Shake well, let the separatory funnel stand still, and after the solution in the separatory funnel separates, remove the lower organic layer. The above operation was repeated three times, and the organic layers were combined. The obtained solution was concentrated under reduced pressure and freeze-dried to obtain a dark blue solid, which was the target probe (NRh-DIOH).
  • 92
  • [ 1122-58-3 ]
  • [ 133-91-5 ]
  • C7H10N2*C7H4I2O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
83% In methanol e. (4- dimethylaminopyridine) : (3,5-diiodosalicylic acid) [(HDMAP + ) •(ddsal -), ddsal -= 3,5-diiodosalicylate] (5) 4-dimethylaminopyridine (12.2 mg, 0.10 mmol) was dissolved in 3 mL methanol. To this solution was added 3,5-diiodosalicylic acid (38.9 mg, 0.1 mmol) in 12 mL methanol. Colorless prisms were afforded after 16 days of slow evaporation of the solvent (yield: 42.5 mg, 83.00%). mp 205.3-207.7 °C. Elem. Anal.: Calc. for C 14 H 14 I 2 N 2 O 3 (512.07): C, 32.81; H, 2.73; N, 5.47. Found: C, 32.75; H, 2.66; N, 5.39. Infrared spectrum (KBr disc, cm -1 ): 3645s( (OH)), 3416s( as (NH)), 3336s( s (NH)), 3240m, 3166m, 3082m, 2966m, 2875w, 1598s( as (COO -)), 1556m, 1513m, 1470w, 1430m, 1388s( s (COO -)), 1345m, 1304m, 1260m, 1216m, 1174m, 1130m, 1086m, 1046m, 1004m, 960m, 916m, 872m, 828m, 784m, 740m, 696m, 658m, 625m, 614m
  • 93
  • [ 133-91-5 ]
  • 4-nitrophenyl bis(carboethoxy) benzylylide [ No CAS ]
  • 3,5-diiodo-2-hydroxybenzoic acid benzyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
91% With 2,6-di-tert-butyl-4-methylpyridinium trifluoromethanesulfonate In dichloromethane at 20℃; for 1h; Molecular sieve; General Procedure A: ylide 2i mediated benzylation General procedure: To the mixture of nucleophile 5 and ylide 2i in CH2Cl2 (c = 0.1 M) in the presence of 4 Å MS (50 mg/mL), TfOH·DTBMP in CH2Cl2 was added. The reaction mixture was stirred at room temperature until the reaction was completed. The reaction mixture was quenched with saturated aqueous NaHCO3, filtered through Celite and extracted with EtOAc. The organic phase was washed with brine, dried over Na2SO4, concentrated, and purified by silica gel flash column chromatography.
  • 94
  • [ 133-91-5 ]
  • tert-butyl 2-(benzyloxy)-3,5-diiodobenzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: dicyclohexyl-carbodiimide; dmap / tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere 2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 °C / Schlenk technique; Inert atmosphere 2.2: 0 - 20 °C / Schlenk technique; Inert atmosphere
  • 95
  • [ 133-91-5 ]
  • tert-butyl 3,5-diiodo-2-((4-methoxybenzyl)oxy)benzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: dicyclohexyl-carbodiimide; dmap / tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere 2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 °C / Schlenk technique; Inert atmosphere 2.2: 0 - 20 °C / Schlenk technique; Inert atmosphere
  • 96
  • [ 133-91-5 ]
  • methyl 5-Iodo-2-methoxy-3-(2-methylallyl)benzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: potassium hydroxide / N,N-dimethyl-formamide / 0 - 20 °C / Inert atmosphere 2.1: pTol2Zn·2LiO(CH2)2N(Me)(CH2)2N(Me)2 / toluene / 0.33 h / 0 °C / Schlenk technique; Inert atmosphere 2.2: 20 °C / Schlenk technique; Inert atmosphere
  • 97
  • [ 133-91-5 ]
  • tert-butyl 2-(Benzyloxy)-5-iodo-3-(2-methylallyl)benzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: dicyclohexyl-carbodiimide; dmap / tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere 2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 °C / Schlenk technique; Inert atmosphere 2.2: 0 - 20 °C / Schlenk technique; Inert atmosphere 3.1: pTol2Zn·2LiO(CH2)2N(Me)(CH2)2N(Me)2 / toluene / 0.33 h / 0 °C / Schlenk technique; Inert atmosphere 3.2: 20 °C / Schlenk technique; Inert atmosphere
  • 98
  • [ 133-91-5 ]
  • tert-butyl 5-iodo-2-((4-methoxybenzyl)oxy)-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-3-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: dicyclohexyl-carbodiimide; dmap / tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere 2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 °C / Schlenk technique; Inert atmosphere 2.2: 0 - 20 °C / Schlenk technique; Inert atmosphere 3.1: pTol2Zn·2LiO(CH2)2N(Me)(CH2)2N(Me)2 / toluene / 0.17 h / 25 °C / Schlenk technique; Inert atmosphere 3.2: 0 - 20 °C / Schlenk technique; Inert atmosphere
  • 99
  • [ 133-91-5 ]
  • [ 75-65-0 ]
  • tert-butyl 2-hydroxy-3,5-diiodobenzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
94% With dmap; dicyclohexyl-carbodiimide In tetrahydrofuran at 20℃; for 0.5h; Inert atmosphere; Synthesis of tert-butyl 2-hydroxy-3,5-diiodobenzoate N,N’-dicyclohexylcarbodiimide (DCC, 8.00 g, 39 mmol) was dissolved in dry THF (50 mL) and added dropwise over 30 min to a stirred suspension of 3,5-diiodosalicylic acid (14.1 g, 36.1mmol) and N,N-dimethylaminopyridine (DMAP, 170 mg, 1.4 mmol) in tert-butyl alcohol (125 mL). The mixture was stirred at room temperature overnight and then concentrated. The residue was stirred in diethyl ether (50 mL), and oxalic acid (5.3 g, 5.9 mmol) was introduced in portions to decompose excess DCC and precipitate DMAP. The mixture was filtered, and the filtrate was washed with aq. NaHCO3 (0.30 M, 3 x 40 mL) and dried over MgSO4. The solvent was evaporated and the crude product was purified via column chromatography (isohexane:ethyl acetate = 9:1, Rf = 0.70) to give the product (15.2 g, 34.1 mmol, 94 %) as a white solid. M.p. (°C): 137-139. 1H-NMR (400 MHz, CDCl3, ppm) δ = 11.92 (s, 1H), 8.14 (d, J = 2.2 Hz, 1H), 8.01 (d, J = 2.2Hz, 1H), 1.60 (s, 9H). 13C-NMR (101 MHz, CDCl3, ppm) δ = 168.1, 160.4, 151.6, 138.7, 115.8, 87.0, 84.7, 80.6, 28.2. IR (ATR, cm-1) ν = 2976, 1675, 1430, 1327, 1158, 790. MS (EI, 70 eV, %) m/z = 390 (100), 373 (22), 372 (98), 57 (17). HRMS (EI, 70 eV) m/z: calc. for C11H12I2O3: 445.8876; found: 445.8862.
  • 100
  • [ 133-91-5 ]
  • [ 107037-95-6 ]
  • 20(S)-hydroxydammar-24-ene-3-oximyl [2-hydroxy-3,5-diiodobenzoate] [ No CAS ]
YieldReaction ConditionsOperation in experiment
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 5h;
Recommend Products
Same Skeleton Products
Historical Records

Related Functional Groups of
[ 133-91-5 ]

Aryls

Chemical Structure| 1015937-56-0

[ 1015937-56-0 ]

Potassium 2-hydroxy-3,5-diiodobenzoate

Similarity: 0.98

Chemical Structure| 520-79-6

[ 520-79-6 ]

2-Hydroxy-3-iodobenzoic acid

Similarity: 0.98

Chemical Structure| 6083-00-7

[ 6083-00-7 ]

2-Hydroxy-3-iodo-5-methylbenzoic acid

Similarity: 0.98

Chemical Structure| 1121-90-0

[ 1121-90-0 ]

2,4-Dihydroxy-5-iodobenzoic acid

Similarity: 0.96

Chemical Structure| 119-30-2

[ 119-30-2 ]

2-Hydroxy-5-iodobenzoic acid

Similarity: 0.93

Carboxylic Acids

Chemical Structure| 520-79-6

[ 520-79-6 ]

2-Hydroxy-3-iodobenzoic acid

Similarity: 0.98

Chemical Structure| 6083-00-7

[ 6083-00-7 ]

2-Hydroxy-3-iodo-5-methylbenzoic acid

Similarity: 0.98

Chemical Structure| 1121-90-0

[ 1121-90-0 ]

2,4-Dihydroxy-5-iodobenzoic acid

Similarity: 0.96

Chemical Structure| 119-30-2

[ 119-30-2 ]

2-Hydroxy-5-iodobenzoic acid

Similarity: 0.93

Chemical Structure| 618-76-8

[ 618-76-8 ]

4-Hydroxy-3,5-diiodobenzoic acid

Similarity: 0.91

Iodides

Chemical Structure| 1015937-56-0

[ 1015937-56-0 ]

Potassium 2-hydroxy-3,5-diiodobenzoate

Similarity: 0.98

Chemical Structure| 520-79-6

[ 520-79-6 ]

2-Hydroxy-3-iodobenzoic acid

Similarity: 0.98

Chemical Structure| 6083-00-7

[ 6083-00-7 ]

2-Hydroxy-3-iodo-5-methylbenzoic acid

Similarity: 0.98

Chemical Structure| 1121-90-0

[ 1121-90-0 ]

2,4-Dihydroxy-5-iodobenzoic acid

Similarity: 0.96

Chemical Structure| 119-30-2

[ 119-30-2 ]

2-Hydroxy-5-iodobenzoic acid

Similarity: 0.93