CAS: 887144-97-0; 3,3-Dimethyl-1-(Trifluoromethyl)-1,2-Benziodoxole

该化合物是高价碘化合物,在有机合成中广泛用作三氟甲基化物剂,其主要优点包括将CF3组转移至核分裂物时具有高度的回动性和选择性,能够对藻类,和异丙烯进行高效的三氟甲基化.试剂在温和条件下运行,通常在室温下运行,并且与广泛的功能组相容. 它的稳定性和处理方便性使得它成为引入三氟甲基聚物的实用选择,这对制药,农用化学品和材料科学都很有价值. Togni的试剂在基和电益三氟化反应中都具有多功能性.

英文名称3,3-Dimethyl-1-(Trifluoromethyl)-1,2-Benziodoxole
中文名称3,3-二甲基-1-(三氟甲基)-1,2-苯并碘氧杂戊环
IUPAC名称3,3-dimethyl-1-(trifluoromethyl)-1λ3,2-benziodoxole
其它别名1-三氟甲基-3,3-二甲基-1,2-苯并碘氧杂戊环; Togni Reagent
CAS编号887144-97-0
MFCD编号:MFCD10567056
EINECS号:626-754-6
FDA UNII编号:3OK0E02MT6
分子式:C10H10F3IO
分子量:330.0846
产品CID: 1905020
产品分类有机原料→通用试剂→氧化剂→高价碘类氧化剂

相似结构搜索
InChIKey: HVAPLSNCVYXFDQ-UHFFFAOYSA-N
InChI=1S/C10H10F3IO/c1-9(2)7-5-3-4-6-8(7)14(15-9)10(11,12)13/h3-6H,1-2H3…
计算化学: 氢键受体数1.0氢键供体数0.0可旋转键数0.0

相似化合物

1391728-13-4 69352-04-1 887144-94-7

物理性质

熔点75-79°C
PSA:9.23
LogP:4.0627
溶解性Chloroform (Slightly), Methanol (Slightly)
外观形态白色至类白色粉末
储存条件2-8°C
产品应用该化合物用于三氟甲基化反应.

MSDS等安全信息

GHS象形图
GHS符号GHS02 & GHS07;
注释: Flame & Exclamation mark
危险类别易燃固体类别2
特定目标器官毒性 - 单次接触类别3
皮肤腐蚀/刺激类别2
严重眼刺激类别2
急性毒性类别3(经口)
严重眼刺激类别2A
警示词Warning(警告)
危险描述H228 |易燃固体.
H335 |可能引起呼吸道刺激.
H315 |造成皮肤刺激.
H319 |造成严重眼刺激.
H301 |吞咽会中毒.
防范说明P210-P240-P241-P261-P264-P271-P280-P302+P352-P304+P340-P362+P364-P370+P378-P405-P501
危险等级4.1
UN编号1325.0
危险品标志Xi
包装等级Ⅲ
安全声明26-36/37
危险类别码36/37/38
WGK Germany3

欧盟法规

C&L通报

上下游产品

合成工艺路线路线简述

合成目标产物 1,3-Dihydro-3,3-Dimethyl-1-(Trifluoromethyl)-1,2-Benziodoxole, Tognis Reagent 主要起始原料 Methyl 2-Iodobenzoate
81290-20-2 + 69352-04-1 = 887144-97-0
反应条件:1.1 Reagents: Potassium Acetate,Tetrabutylammonium Difluorotriphenylsilicate Solvents: Acetonitrile
标题:Electrophilic Trifluoromethylation - Approaches With Hypervalent Iodine Compounds
作者:Kieltsch,Iris
参考文献:2008]

81290-20-2 + 69352-04-1 = 887144-97-0
反应条件:1.1 Reagents: Potassium Acetate Solvents: Acetonitrile1.2 Catalysts: Tetrabutylammonium Difluorotriphenylsilicate Solvents: Acetonitrile; Rt -> -17 °C; 16 H,-17 °C; -17 °C -> -12 °C; -12 °C -> Rt; 3 H,Rt
标题:Mild Electrophilic Trifluoromethylation Of Carbon- And Sulfur-Centered Nucleophiles By A Hypervalent Iodine(Iii)-Cf3 Reagent
作者:Kieltsch,Iris; Eisenberger,Patrick; Togni,Antonio
参考文献:Angewandte Chemie 日期:2007 卷标:46(5) 页码:754-757]

81290-20-2 + 69352-04-1 = 887144-97-0
反应条件:1.1 Reagents: Potassium Fluoride Solvents: Acetonitrile; 12 H,Rt; Rt -> -10 °C1.2 1 H,-10 °C
标题:One-Pot Synthesis Of Hypervalent Iodine Reagents For Electrophilic Trifluoromethylation
作者:Matousek,Vaclav; Pietrasiak,Ewa; Schwenk,Rino; Togni,Antonio
参考文献:Journal Of Organic Chemistry 日期:2013 卷标:78(13) 页码:6763-6768]

81290-20-2 + 175786-58-0 = 887144-97-0
反应条件:1.1 Catalysts: Cesium Fluoride Solvents: Acetonitrile; 16 H,23 °C
标题:Connecting Binuclear Pd(Iii) And Mononuclear Pd(Iv) Chemistry By Pd-Pd Bond Cleavage
作者:Powers,David C.; Lee,Eunsung; Ariafard,Alireza; Sanford,Melanie S.; Yates,Brian F.; Et Al
参考文献:Journal Of The American Chemical Society 日期:2012 卷标:134(29) 页码:12002-12009]

81290-20-2 + 1391728-13-4 = 887144-97-0
反应条件:1.1 Catalysts: Tetrabutylammonium Difluorotriphenylsilicate Solvents: Acetonitrile
标题:Supramolecular Aggregation Of Perfluoroorganyl Iodane Reagents In The Solid State And In Solution
作者:Liebing,Phil; Pietrasiak,Ewa; Otth,Elisabeth; Kalim,Jorna; Bornemann,Dustin; Et Al
参考文献:European Journal Of Organic Chemistry 日期:2018 卷标:2018(27-28) 页码:3771-3781]

81290-20-2 + 69352-04-1 = 887144-97-0
反应条件:1.1 Reagents: Potassium Acetate Solvents: Acetonitrile1.2 Reagents: Tetrabutylammonium Difluorotriphenylsilicate Solvents: Acetonitrile
标题:The Development Of New Hypervalent Iodine Reagents For Electrophilic Trifluoromethylation
作者:Eisenberger,Patrick
参考文献:2007]

81290-20-2 + 69352-04-1 = 887144-97-0
反应条件:1.1 Reagents: Potassium Acetate Solvents: Acetonitrile; 1 H,Rt; Rt -> -17 °C1.2 Catalysts: Tetrabutylammonium Difluorotriphenylsilicate Solvents: Acetonitrile; -17 °C; 16 H,-17 °C; -17 °C -> -12 °C; 3 H,-12 °C -> Rt; 3 H,Rt
标题:Preparation Of A Trifluoromethyl Transfer Agent: 1-Trifluoromethyl-1,3-Dihydro-3,3-Dimethyl-1,2-Benziodoxole
作者:Eisenberger,Patrick; Kieltsch,Iris; Koller,Raffael; Stanek,Kyrill; Togni,Antonio
参考文献:Organic Syntheses 日期:2011 卷标:88 页码:168-180]

69352-04-1 = 887144-97-0
反应条件:1.1 Reagents: Hexamethylborazine,18-Crown-6 Solvents: Tetrahydrofuran; 30 Min,0 °C1.2 Reagents: (Phenylmethyl)Potassium; 2 Min,0 °C1.3 2 Min,0 °C -> Rt1.4 10 Min,Rt
标题:Borazine-Cf3- Adducts For Rapid,Room Temperature,And Broad Scope Trifluoromethylation
作者:Geri,Jacob B.; Wade Wolfe,Michael M.; Szymczak,Nathaniel K.
参考文献:Angewandte Chemie 日期:2018 卷标:57(5) 页码:1381-1385]

69352-04-1 = 887144-97-0
反应条件:1.1 Reagents: Hexamethylborazine Catalysts: 18-Crown-6 Solvents: Tetrahydrofuran; 30 Min,0 °C1.2 Reagents: (Phenylmethyl)Potassium; 2 Min,0 °C1.3 2 Min,0 °C; 0 °C -> Rt1.4 10 Min,Rt
标题:Recyclable Trifluoromethylation Reagents From Fluoroform
作者:Geri,Jacob B.; Szymczak,Nathaniel K.
参考文献:Journal Of The American Chemical Society 日期:2017 卷标:139(29) 页码:9811-9814]

81290-20-2 + 69352-04-1 = 887144-97-0
反应条件:1.1 Reagents: Potassium Fluoride Solvents: Acetonitrile; 24 H,25 °C; 25 °C -> -10 °C1.2 1 H,-10 °C; -10 °C -> 25 °C; 1 H,25 °C
标题:The 3-Position-Selective C-H Trifluoromethylation Of Pyridine Rings Based On Nucleophilic Activation
作者:Muta,Ryuhei; Torigoe,Takeru; Kuninobu,Yoichiro
参考文献:Organic Letters 日期:2022 卷标:24(44) 页码:8218-8222]

81290-20-2 + 69352-04-1 = 887144-97-0
反应条件:1.1 Reagents: Potassium Fluoride Solvents: Acetonitrile; 24 H,25 °C; 25 °C -> -10 °C1.2 1 H,-10 °C; -10 °C -> 25 °C; 1 H,25 °C
标题:3-Position-Selective C-H Trifluoromethylation Of Pyridine Rings Based On Nucleophilic Activation
作者:Muta,Ryuhei; Torigoe,Takeru; Kuninobu,Yoichiro
参考文献:Chemrxiv 日期:2022 卷标:1 页码:1-6]

81290-20-2 + 175786-58-0 = 887144-97-0
反应条件:1.1 Catalysts: Cesium Fluoride Solvents: Acetonitrile; 16 H,Rt
标题:Novel 10-I-3 Hypervalent Iodine-Based Compounds For Electrophilic Trifluoromethylation
作者:Eisenberger,Patrick; Gischig,Sebastian; Togni,Antonio
参考文献:Chemistry - A European Journal 日期:2006 卷标:12(9) 页码:2579-2586

2-(2-碘苯基)-2-丙醇置于次氯酸叔丁酯,Cesium Fluoride体系中,用乙腈作为反应溶剂,化学反应 31.0H,反应生成 3,3-二甲基-1-(三氟甲基)-1,2-苯并碘氧杂戊环
参考文献:用于亲电子三氟甲基化的新型10-I-3高价碘基化合物.
标题:用于亲电子三氟甲基化的新型10-I-3高价碘基化合物.
摘要:描述了新的10-I-3高价碘化合物家族的合成,其中cf3官能团直接参与高价键.在亚化学计量的氟化物存在下,可以使用me3Sicf3在碘上通过亲核配体取代来获得这些材料.通过x射线晶体学分析,对三种产物(1-三氟甲基-1,2-苯并三恶唑-3-(1 H)-一和两个取代的1-三氟甲基-1,3)进行了验证,得出了碘中预期的t形几何形状.-二氢-1,2-苯并恶唑).三氟甲基部分直接亲电转移到有机亲核试剂上的初步结果表明,在相对温和的条件下,在极性非质子传递溶剂中有适度的反应性.整个过程可以理解为cf3小组的正式成员.
DOI:10.1002/chem.200501052

海关参考信息

2902600000-乙苯
2902700000-异丙基苯
2905122000-异丙醇
2906210000-苄醇
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专利信息

专利号:US-2025197439-A1
优先权日:2022-03-18
标题:Decarboxylative acetoxylation using mn(ii) or mn(iii) reagent for synthesis of 4'-acetoxy-nucleoside and use thereof for synthesis of corresponding 4'-(dimethoxyphosphoryl)methoxy-nucleotide
发明人：VAGLE KURT EDRIC; BHADURI SAYANTAN; YANG GUOHAN
权利人:DICERNA PHARMACEUTICALS INC
摘要:The present invention relates to the preparation of nucleic acids, nucleosides, nucleotides, and analogues thereof useful as potent and stable RNA interference agents. The present invention provides improved yields and avoids the use of lead tetraacetate for decarboxylative acetylation which decreases the overall cost of production by removing the need for lead remediation and offers a significant reduction in the environmental costs in production.

专利号:WO-2024000920-A1
优先权日:2022-06-28
标题 :Method for preparing Î²-trifluoromethylenamine compound on basis of organic dye catalysis
发明人：CHEN XIAOYUN; TANG YISONG; ZHANG XIAOTONG; HUANG MINGYANG; QI GUANGJIE; XIANG XINRAN
权利人:UNIV JIANGSU SCIENCE & TECH
摘要:Disclosed in the present invention is a method for preparing a Î²-trifluoromethylenamine compound on the basis of organic dye catalysis. The present invention belongs to the technical fields of the synthesis of medicines, pesticide products and material intermediates. The Î²-trifluoromethylenamine compound has a structure as represented by formula (I). The preparation method of the present invention comprises: under the irradiation of environment-friendly, green and economic visible light, using a catalytic amount of a commercial organic dye Na2-Eosin Y as a photocatalyst, using CF3SO2Na which is cheap, easily available, stable and simple and convenient to operate as a trifluoromethyl source, using Na2CO3 as an additive, and using tert-butyl hydroperoxide as an initiator. The reaction has mild conditions and is insensitive to air and water, and the operation is simple and convenient, the reaction efficiency is high, and the target product is easy to purify. In addition, the present invention has a a wide reaction substrate range and good functional group tolerance, and most of the target product compounds can be obtained with good to significant yields.

专利号:EP-4493568-A1
优先权日:2022-03-18
标题 :Decarboxylative acetoxylation using mn(ii) or mn(iii) reagent for synthesis of 4'-acetoxy- nucleoside and use thereof for synthesis of corresponding 4'-(dimethoxyphosphoryl)methoxy- nucleotide

专利号:WO-2023177866-A1
优先权日:2022-03-18
标题 :Decarboxylative acetoxylation using mn(ii) or mn(iii) reagent for synthesis of 4'-acetoxy- nucleoside and use thereof for synthesis of corresponding 4'-(dimethoxyphosphoryl)methoxy- nucleotide

专利号:CN-113527264-B
优先权日:2021-06-21
标题 :Synthesis of a Class of Nitrogen-Containing Heterocyclic Fluorocarbon Surfactants and Preparation of Aqueous Micelles by Photoreaction-Click Reaction

专利号:CN-118755680-A
优先权日:2024-08-20
标题:Non-heme iron enzyme BsQueD or mutant thereof and application thereof in synthesis of ortho-trifluoromethyl substituted azide

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主要参考文献

[参考文献]: Anna E Allen, Et Al. The Productive Merger Of Iodonium Salts And Organocatalysis: A Non-Photolytic Approach To The Enantioselective Alpha-Trifluoromethylation Of Aldehydes. J Am Chem Soc. 2010 Apr 14;132(14):4986-7.
[参考文献]: Katrin Niedermann, Et Al. A Ritter-Type Reaction: Direct Electrophilic Trifluoromethylation At Nitrogen Atoms Using Hypervalent Iodine Reagents. Angew Chem Int Ed Engl. 2011 Feb 1;50(5):1059-63.
[参考文献]: Katrin Niedermann, Et Al. Direct Electrophilic N-Trifluoromethylation Of Azoles By A Hypervalent Iodine Reagent. Angew Chem Int Ed Engl. 2012 Jun 25;51(26):6511-5.
[参考文献]: Tianfei Liu, Et Al. Copper-Catalyzed Trifluoromethylation Of Aryl And Vinyl Boronic Acids With An Electrophilic Trifluoromethylating Reagent. Org Lett. 2011 May 6;13(9):2342-5.
[参考文献]: Tianfei Liu, Et Al. Highly Selective Trifluoromethylation Of 1,3-Disubstituted Arenes Through Iridium-Catalyzed Arene Borylation. Angew Chem Int Ed Engl. 2012 Jan 9;51(2):540-3.

合成参考文献

摘要:Kleoff, M.; Omoregbee, K.; Zimmer, R., Science of Synthesis Knowledge Updates, (2018) 4, 212.
摘要:Kleoff, M.; Omoregbee, K.; Zimmer, R., Science of Synthesis Knowledge Updates, (2018) 4, 218.
摘要:Kleoff, M.; Omoregbee, K.; Zimmer, R., Science of Synthesis Knowledge Updates, (2018) 4, 209.
摘要:Zhdankin, V. V., Science of Synthesis Knowledge Updates, (2015) 1, 256.
摘要:Zhdankin, V. V., Science of Synthesis Knowledge Updates, (2015) 1, 262.

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CAS: 887144-97-0; 3,3-Dimethyl-1-(Trifluoromethyl)-1,2-Benziodoxole

相似化合物

物理性质

MSDS等安全信息

欧盟法规

上下游产品

合成工艺路线路线简述

海关参考信息

专利信息

其他信息查阅

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