CAS: 80-48-8; Methyl 4-Methylbenzenesulfonate

该化合物是甲苯的全氟辛烷磺酸衍生物,通常用作有机合成中的烷基剂,其主要优点包括核循环替代反应中的高度反应性,能够有效地将四甲基苯基磺酰氟(Tosyl)组引入目标分子;该化合物在标准储存条件下具有良好稳定性,确保合成应用的一贯性能;对于准备受保护的中间体以及作为制药和精美化学制造的先质特别有用;甲基酯会提高有机溶剂的溶解性,便利其在同质反应系统中的使用;建议适当处理,因为其潜在的乳液和刺激性能.

英文名称Methyl 4-Methylbenzenesulfonate
中文名称对甲苯磺酸甲酯
IUPAC名称methyl 4-methylbenzenesulfonate
其它别名对甲基磺酸甲苯; P-Toluenesulfonic Acid Methyl Ester
CAS编号80-48-8
MFCD编号:MFCD00008417
EINECS号:201-283-5
FDA UNII编号:4SU69KI68L
分子式:C8H10O3S
分子量:186.23
产品CID: 1800152
产品分类有机原料→分子砌块→芳环类化合物→苯类化合物

相似结构搜索
InChIKey: VUQUOGPMUUJORT-UHFFFAOYSA-N
InChI=1S/C8H10O3S/c1-7-3-5-8(6-4-7)12(9,10)11-2/h3-6H,1-2H3…
计算化学: 氢键受体数3.0氢键供体数0.0可旋转键数2.0

物理性质

熔点25-28 °C
沸点291.8°C at 760 mmHg
闪点>110°C
密度1.2±0.1 g/cm3
PSA:43.37
LogP:1.33012
折射率1.517
蒸汽压0.0±0.6 mmHg at 25°C
溶解性Chloroform (Slightly), Methanol (Slightly)
敏感性易受潮
外观形态白色至黄色液体或低熔点固体
储存条件2-8°C
产品应用在有机合成反应中作甲基化剂.
性质描述白色结晶.熔点28-29°C,沸点292°C,146-147°C(1.2kPa),相对密度1.231(20/4°C).易溶于乙醇,乙醚,苯,不溶于水.具吸湿性.

MSDS等安全信息

GHS象形图
GHS符号GHS07 & GHS05;
注释: Exclamation mark & Corrosion
危险类别急性毒性类别4(经口)
皮肤腐蚀类别1C
严重眼损伤类别1
皮肤致敏类别1B
皮肤腐蚀类别1
皮肤腐蚀/刺激类别2
严重眼刺激类别2
皮肤致敏类别1
皮肤腐蚀类别1B
特定目标器官毒性 - 单次接触类别3
皮肤致敏类别1A
急性毒性类别4(吸入)
急性毒性类别4(经皮)
皮肤腐蚀类别1A
金属腐蚀物类别1
致癌性类别2
致突变性类别2
急性毒性类别3(经皮)
水生慢性毒性类别2
警示词Danger(危险)
危险描述H302 |吞咽有害.
H314 |造成严重皮肤灼伤和眼损伤.
H318 |造成严重眼损伤.
H317 |可能引起皮肤过敏反应.
H315 |造成皮肤刺激.
H319 |造成严重眼刺激.
H335 |可能引起呼吸道刺激.
H332 |吸入有害.
H312 |皮肤接触有害.
H290 |可能对金属造成腐蚀.
H351 |怀疑致癌.
H341 |怀疑导致遗传缺陷.
H311 |皮肤接触会中毒.
H411 |对水生生物有毒并具有长期持续影响.
防范说明P260-P261-P264-P270-P272-P273-P280-P301+P330+P331-P302+P352-P303+P361+P353-P304+P340-P305+P351+P338-P330-P362+P364-P363-P405-P501
危险等级8
UN编号3261.0
危险品标志C,Xn
包装等级Ⅱ
安全声明26-36/37/39-45-24
危险类别码22-34-43-40-36/37/38
WGK Germany3

欧盟法规

REACH注册ECHA物质C&L通报REACH预注册

上下游产品

合成工艺路线路线简述

合成目标产物 Methyl P-Toluenesulfonate 主要起始原料 Trimethyl Orthoacetate And P-Toluenesulfonic Acid
824-79-3 = 80-48-8
反应条件:1.1 Reagents: Iodobenzene Diacetate; 15 Min,Rt
标题:Rapid Transformation Of Sulfinate Salts Into Sulfonates Promoted By A Hypervalent Iodine(Iii) Reagent
作者:Deruer,Elsa; Et Al
参考文献:Beilstein Journal Of Organic Chemistry 日期:2018 卷标:14 页码:1203-1207]

= 80-48-8
反应条件:1.1 Solvents: Methanol,Tetrahydrofuran; 5 °C; 12 H,Rt
标题:Anchored Block-Copolymer Surfactants For The Synthesis Of Redispersible Polystyrene Latexes
作者:Keerthika,Nagarajan; Et Al
参考文献:Journal Of Applied Polymer Science 日期:2020 卷标:137(29)]

104-15-4 + 143674-36-6 = 80-48-8
反应条件:1.1 Reagents: M-Chloroperbenzoic Acid Solvents: Dichloromethane; -78 °C; 10 Min,0 °C; 4 H,Reflux
标题:A New Preparative Method Of Aryl Sulfonate Esters By Using Cyclic Organobismuth Reagents
作者:Sakurai,Naoto; Et Al
参考文献:Heterocycles 日期:2007 卷标:74 页码:771-790]

104-15-4 + 398477-62-8 = 80-48-8
反应条件:1.1 Solvents: Dichloromethane
标题:Synthesis Of Alkyl Sulfonates From Sulfonic Acids Or Sodium Sulfonates Using Solid-Phase Bound Reagents
作者:Vignola,N.; Et Al
参考文献:Tetrahedron Letters 日期:2001 卷标:42(44) 页码:7833-7836]

= 80-48-8
反应条件:1.1 Reagents: Hydrochloric Acid,Oxygen,1,4-Diazoniabicyclo[2.2.2]Octane,1,4-Disulfino-,Bis(Inner Salt) Catalysts: Cuprous Iodide Solvents: Dichloromethane,Water; 4 H,Rt
标题:Visible-Light-Induced One-Pot Synthesis Of Sulfonic Esters Via Multicomponent Reaction Of Arylazo Sulfones And Alcohols
作者:Luu,Truong Giang; Et Al
参考文献:Rsc Advances 日期:2022 卷标:12(27) 页码:17499-17504]

104-15-4 = 80-48-8
反应条件:1.1 Solvents: Toluene
标题:Reaction Of Phosphorus Oxyacid Esters With P-Toluenesulfonic Acid
作者:Nitta,Yoshihiro; Et Al
参考文献:Chemical & Pharmaceutical Bulletin 日期:1986 卷标:34(7) 页码:2710-18]

104-15-4 = 80-48-8 [标题:Reaction Conditions
标题:Esterification Of Aliphatic Sulfonic Acids With Dimethyl Sulfate
作者:Forbes,C. P.; Et Al
参考文献:Cellulose Chemistry And Technology 日期:1981 卷标:15(6) 页码:691-3]

1067-52-3 = 80-48-8 [标题:Reaction Conditions
标题:The Reactions Of Trialkyl(Alkoxy)Stannane With Sulfonyl,Sulfinyl,And Sulfenyl Chlorides
作者:Kozuka,Seizi; Et Al
参考文献:Memoirs Of The Faculty Of Engineering 日期:1978 卷标:19 页码:181-3]

= 80-48-8
反应条件:1.1 Reagents: Oxygen Catalysts: Acridinium,10-Methyl-9-(2,4,6-Trimethylphenyl)-,Perchlorate (1:1) Solvents: Methanol; 36 H,Rt
标题:Photoinduced Oxidative Cross-Coupling For O-S Bond Formation: A Facile Synthesis Of Alkyl Benzenesulfonates
作者:Singh,Atul K.; Et Al
参考文献:Synlett 日期:2017 卷标:28(13) 页码:1558-1563]

70-55-3 = 80-48-8
反应条件:1.1 Reagents: Trifluoroacetic Acid,Tert-Butyl Nitrite,Magnesium Chloride Solvents: Acetonitrile; 7 H,50 °C1.2 Reagents: Triethylamine Solvents: Acetonitrile; 40 Min,Rt
标题:Diazotization-Enabled Deaminative Late-Stage Functionalization Of Primary Sulfonamides
作者:Li,Jiang-Sheng; Et Al
参考文献:Organic Letters 日期:2023 卷标:25(46) 页码:8263-8268]

80-11-5 = 80-48-8
反应条件:1.1 Solvents: Tert-Butanol,Pentane
标题:Sulfonylnitrosamides. Iv. Thermal Rearrangement Of Sulfonylmethylnitrosamides
作者:De Boer,Th. J.
参考文献:Recueil Des Travaux Chimiques Des Pays-Bas Et De La Belgique 日期:1954 卷标:73 页码:677-85]

104-15-4 = 80-48-8
反应条件:1.1 Reagents: Silica Solvents: Toluene; 5 Min,120 °C
标题:Direct Synthesis Of Sulfonates Of Alcohol,Oxyma-O-Sulfonates And Oxime-O-Sulfonates Under Microwave Irradiation
作者:Chandra,Jyoti; Et Al
参考文献:Chemistryselect 日期:2017 卷标:2(27) 页码:8471-8477]

104-15-4 = 80-48-8
反应条件:1.1 Reagents: Iron (Exchanged Montmorillonite Clay) Solvents: 1,2-Dichloroethane
标题:Montmorillonite Clay Catalyzed Tosylation Of Alcohols And Selective Monotosylation Of Diols With P-Toluenesulfonic Acid: An Enviro-Economic Route
作者:Choudary,B. M.; Et Al
参考文献:Tetrahedron 日期:2000 卷标:56(37) 页码:7291-7298]

824-79-3 = 80-48-8
反应条件:1.1 Reagents: Styrene,Trimethylsilyl Triflate Solvents: Acetic Acid,Acetonitrile; 12 H,25 - 35 °C
标题:Photo-Induced Stereo- And Regiospecific Sulfonylation Of C-C Multiple Bonds Exploiting The Dual Reactivity Of Sulfonium Iodate(I) Species
作者:Gurawa,Aakanksha; Et Al
参考文献:Organic Chemistry Frontiers 日期:2023 卷标:10(19) 页码:4918-4926]

824-79-3 = 80-48-8
反应条件:1.1 Reagents: Ferric Nitrate Solvents: Methanol; 2 H,Rt
标题:Iron(Iii)-Mediated Oxy-Sulfonylation Of Enamides With Sodium And Lithium Sulfinates
作者:Kramer,Philipp; Et Al
参考文献:Journal Of Organic Chemistry 日期:2020 卷标:85(5) 页码:3617-3637]

= 80-48-8
反应条件:1.1 Reagents: Triethylamine Catalysts: Trimethylammonium Chloride Solvents: Toluene; Cooled1.2 Solvents: Toluene; 10 Min,Cooled; 1 H,0 °C
标题:Efficient,Scalable And Economical Preparation Of Tris(Deuterium)- And 13C-Labelled N-Methyl-N-Nitroso-P-Toluenesulfonamide (Diazald) And Their Conversion To Labelled Diazomethane
作者:Shields,Samuel W. J.; Et Al
参考文献:Journal Of Labelled Compounds And Radiopharmaceuticals 日期:2014 卷标:57(12) 页码:674-679]

= 80-48-8
反应条件:1.1 Reagents: Methane,Nitro-,Ion(1-),Sodium Solvents: Methanol
标题:Pathways In The Reactions Of Nitronate Ions With Sulfonyl Halides
作者:Pigou,Paul E.; Et Al
参考文献:Journal Of The Chemical Society 日期:1988 卷标:(5) 页码:725-30]

= 80-48-8
反应条件:1.1 Solvents: Pyridine
标题:Piperidine Derivatives. Xxvi. 1-Methyl-3-Benzylidene-4-Piperidone Dimer
作者:Mcelvain,S. M.; Et Al
参考文献:Journal Of The American Chemical Society 日期:1955 卷标:77 页码:492-3]

657-84-1 = 80-48-8
反应条件:1.1 Reagents: Triphenylphosphine,Chlorine Solvents: Acetonitrile1.2 Reagents: Pyridine1.3 Reagents: Water
标题:Preparation Of Sulfonamides From Sodium Sulfonates. Ph3Pbr2 And Ph3Pcl2 As A Mild Halogenating Reagent For Sulfonyl Bromides And Sulfonyl Chlorides
作者:Kataoka,Tadashi; Et Al
参考文献:Synthesis 日期:1998 卷标:(4) 页码:423-426]

657-84-1 = 80-48-8
反应条件:1.1 Reagents: Boron Trifluoride Etherate,Hydrochloric Acid Solvents: Methanol
标题:Sulfinic Acids And Related Compounds. 15. Convenient Methods For Esterifying Sensitive Sulfinic Acid Salts
作者:Srivastava,Pramod K.; Et Al
参考文献:Phosphorus And Sulfur And The Related Elements 日期:1985 卷标:25(2) 页码:161-5]

1825-61-2 = 80-48-8
反应条件:1.1 Catalysts: Tin Tetrachloride
标题:Synthesis Of Organosulfur Compounds Via Silicon-Containing Reagents
作者:Mizhiritskii,M. D.; Et Al
参考文献:Zhurnal Obshchei Khimii 日期:1986 卷标:56(7) 页码:1547-58]

104-15-4 + 512-56-1 = 80-48-8
反应条件:1.1 Solvents: Toluene
标题:Reaction Of Phosphorus Oxyacid Esters With P-Toluenesulfonic Acid
作者:Nitta,Yoshihiro; Et Al
参考文献:Chemical & Pharmaceutical Bulletin 日期:1986 卷标:34(7) 页码:2710-18]

104-15-4 + 512-56-1 = 80-48-8 [标题:Reaction Conditions
标题:Product Subclass 2: Arenesulfonic Acid Derivatives
作者:Shcherbakova,I.
参考文献:Science Of Synthesis 日期:2007 卷标:31 页码:775-832]

104-15-4 + 398477-62-8 = 80-48-8
反应条件:1.1 Solvents: Dichloromethane; 4 H,Rt
标题:Efficient Synthesis Of Sulfonic,Phosphoric,And Phosphinic Esters Employing Alkylating Polymer-Bound Reagents
作者:Vignola,Nicola; Et Al
参考文献:Journal Of Combinatorial Chemistry 日期:2003 卷标:5(2) 页码:138-144]

104-15-4 + 398477-62-8 = 80-48-8 [标题:Reaction Conditions
标题:Product Subclass 2: Arenesulfonic Acid Derivatives
作者:Shcherbakova,I.
参考文献:Science Of Synthesis 日期:2007 卷标:31 页码:775-832]

4124-41-8 = 80-48-8 [标题:Reaction Conditions
标题:Sulfonic Acid-Induced Fragmentation Of Dialkyl Acylphosphonates,Formation Of Alkyl Carboxylates And Alkyl Sulfonates
作者:Breuer,Eli; Et Al
参考文献:Journal Of The Chemical Society 日期:1988 卷标:(12) 页码:2029-34

对甲苯二硫醚置于sodium Hypochlorite Pentahydrate体系中,用甲醇作为反应溶剂,化学反应 3.0H,以35%的收率获得产物对甲苯磺酸甲酯
参考文献:一种制备磺酰氯的有效方法:二硫化物或硫醇与五水次氯酸钠 (Naocl.5H2O) 晶体的反应
标题:一种制备磺酰氯的有效方法:二硫化物或硫醇与五水次氯酸钠 (Naocl.5H2O) 晶体的反应
摘要:二硫化物或硫醇与五水合次氯酸钠在乙酸中的反应有效地以高产率提供了相应的磺酰氯.
DOI:10.1246/cl.140899

海关参考信息

2902300000-甲苯
2905110000-甲醇
2904100000-仅含磺基的衍生物及其盐和乙酯
💡 提示：海关信息按照顺序优先匹配，如需确认的海关信息，请参考相关资料。
详情请参考：📖 海关编码查询和海关进出口税则

专利信息

专利号:US-8461357-B2
优先权日:2008-09-19
标题 :Expeditious synthesis of gibberellin A5 and esters thereof
发明人：FAIRWEATHER KELLY A; MANDER LEWIS N; PHARIS RICHARD P
权利人:FAIRWEATHER KELLY A; MANDER LEWIS N; PHARIS R P; UTI LIMITED PARTNERSHIP
摘要:An expeditious synthesis of gibberellin A 5 (GA 5 ) esters is presented, from which GA 5 may be prepared. The synthesis offers an inexpensive route of few steps to these compounds, starting from gibberellin A 3 (GA 3 ) esters in the presence of a metal hydride.

专利号:US-8058414-B2
优先权日:2008-04-29
标题 :Unnatural polymerase substrates that can sustain enzymatic synthesis of double stranded nucleic acids from a nucleic acid template and methods of use
发明人：MENCHEN STEVEN; ROSENBLUM BARNETT; KENNEY PAUL; KHAN SHOEB; MA ZHAOCHUN; CHEN JER-KANG; LAM JOE Y; HUANG BOLI
权利人:MENCHEN STEVEN; ROSENBLUM BARNETT; KENNEY PAUL; KHAN SHOEB; MA ZHAOCHUN; CHEN JER-KANG; LAM JOE Y; HUANG BOLI; LIFE TECHNOLOGIES CORP
摘要:Nucleotide analogs that can sustain the enzymatic synthesis of double-stranded nucleic acid from a nucleic template are described. The nucleotide analogs include: (i) a base selected from the group consisting of adenine, guanine, cytosine, thymine, uracil and their analogs; (ii) a label attached to the base or analog of the base via a cleavable linker; (iii) a deoxyribose; and (iv) one or more phosphate groups. The linker and/or the label inhibits template directed polymerase incorporation of a further nucleotide substrate onto an extended primer strand. In addition, cleavage of the linker leaves a residue attached to the base which is not present in the natural nucleotide and which does not inhibit extension of the primer strand. The nucleotide analogs can therefore be used as reversible terminators in sequencing by synthesis methods without blocking the 3â€² hydroxyl group. Methods of sequencing DNA using the substrates are also described.

专利号:US-9085538-B2
优先权日:2010-07-26
标题:Process for the preparation of key intermediates for the synthesis of statins or pharmaceutically acceptable salts thereof
发明人：CASAR ZDENKO; STERK DAMJAN; JUKIC MARKO
权利人:CASAR ZDENKO; STERK DAMJAN; JUKIC MARKO; LEK PHARMACEUTICALS
摘要:The invention relates to commercially viable process for the synthesis of key intermediates for the preparation of statins, in particular Rosuvastatin and Pitavastatin or respective pharmaceutically acceptable salts thereof. A new simple and short synthetic route for key intermediates is presented which benefits from the use of cheap and readily available starting materials, by which the conventionally most frequently used DIBAL-H as reducing agent can be avoided.

专利号:US-11512062-B2
优先权日:2018-10-15
标题:Process for the synthesis of piperazinyl-ethoxy-bromophenyl derivates and their application in the production of compounds containing them
发明人：BEAUREGARD LOUIS-PHILIPPE; BERTRAND MARTIAL; GIGUERE PASCALL; HARDOUIN CHRISTOPHE; SCHIAVI BRUNO
权利人:SERVIER LAB
摘要:Process for the industrial synthesis of the compound of formula (I):

专利号:US-4756739-A
优先权日:1985-12-21
标题 :Pyridine derivatives and the N-oxides thereof, and the use thereof as intermediates for the synthesis of plant protecting agents
发明人：FUSS ANDREAS; KOCH VOLKER
权利人:HOECHST AG
摘要:The compounds of the formula I (I) in which A denotes N or N->O, Z denotes O or NH, R denotes H, (halo)alkyl, (halo)alkenyl, (halo)alkynyl or alkoxycarbonyl, R1 denotes hydrogen, halogen, amino, -NHOH, hydroxyl, (substituted) phenylazo or a radical of the formulae Y=C=N-, Y1Y2C=N-, Y3NH- or K denotes 0 or 1, and m and n, independently of one another, denote a number from 1 to 4, with the proviso that, when Z-R denotes OH or NH2, (R1)n denotes at least one radical of the formula or represents two radicals, in the 5 or 6 position of the heterocyclic ring, which, in the 5 position, denote halogen and, in the 6 position, denote a radical of the group comprising halogen, amino, hydroxyl or phenylazo, which may be substituted as specified above, are valuable intermediates in the synthesis of plant protection agents.

专利号:US-4237054-A
优先权日:1979-05-18
标题 :Total synthesis of (1RS,4SR,5RS)-4-(4,8-dimethyl-5-hydroxy-7-nonenyl)-4-methyl-3,8-dioxabicyclo[3.2.1] octane-1-acetic acid
发明人：CHEN ROBERT H K
权利人:ORTHO PHARMA CORP
摘要:A method for the total synthesis of (1RS,4SR,5RS)-4-(4,8-dimethyl-5-hydroxy-7-nonenyl)-4-methyl-3,8-dioxabicyclo [3.2.1] octane-1-acetic acid is described. The compound is active as a utero-evacuant agent.

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主要参考文献

[参考文献]: Tian Guo, Et Al. Rapid And Simultaneous Determination Of Sulfonate Ester Genotoxic Impurities In Drug Substance By Liquid Chromatography Coupled To Tandem Mass Spectrometry: Comparison Of Different Ionization Modes. J Chromatogr A. 2014 Aug 15:1355:73-9.

合成参考文献

摘要:Haino, T.; Iwamoto, H., Science of Synthesis, (2010) 45, 1210.
摘要:Hlina, J. A., Science of Synthesis Knowledge Updates, (2021) 1, 82.
摘要:Schnürch, M.; Hämmerle, J.; Stanetty, P., Science of Synthesis Knowledge Updates, (2010) 1, 199.
摘要:Shu, X.-Z.; Pang, X., Science of Synthesis: Special Topics, (2022) 1, 416.
摘要:Prehled Prumyslove Toxikologie; Organicke Latky, Marhold, J., Prague, Czechoslovakia, Avicenum, 1986, -(1067), 1986