CAS: 80-11-5; N-Methyl-N-Nitrosotoluene-4-Sulfonamide

该化合物是一种化学化合物,属于硝胺类,以其潜在的致癌性而闻名;该物质的特征是存在一个硝酸盐组(-NO),该组附属于磺酰胺结构,特别是p-toluenesulfonide,该组有助于其化学反应和生物活动;该组通常在室内温度下为黄色至褐色的固体,可溶于有机溶剂;该组主要用于研究环境,特别是与其生物效应和行动机制有关的研究;由于其硝胺结构,必须谨慎处理该物质,因为硝酸胺可能具有危险性,并因其潜在的健康风险而需接受监管审查;适当的安全措施,包括使用个人防护设备和遵守危险材料准则,在与该化合物合作时至关重要.

英文名称N-Methyl-N-Nitrosotoluene-4-Sulfonamide
中文名称N-甲基-N-亚硝基甲苯-4-磺酰胺
IUPAC名称N,4-dimethyl-N-nitrosobenzenesulfonamide
其它别名N-Methyl-N-(p-tolylsulfonyl)nitrosamide; Diazald; p-Tolylsulfomethylnitrosamide
CAS编号80-11-5
MFCD编号:MFCD00002050
EINECS号:201-252-6
分子式:C8H10N2O3S
分子量:214.24
产品CID: 2362150
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: FFKZOUIEAHOBHW-UHFFFAOYSA-N
InChI=1S/C8H10N2O3S/c1-7-3-5-8(6-4-7)14(12,13)10(2)9-11/h3-6H,1-2H3…
计算化学: 氢键受体数5.0氢键供体数0.0可旋转键数2.0

物理性质

熔点~58 °C
沸点320.5±35.0 °C(预测)
闪点147.6 °C
密度1.3844 (粗估)
pKa:-19.25±0.70(预测)
PSA:75.19
LogP:2.3777
折射率1.5690 (估算)
蒸汽压0.00000479 [mmHg]
溶解性Chloroform (Slightly), Dichloromethane (Sparingly), DMSO (Slightly), Ethyl Acetate
外观形态淡黄色至黄色固体
储存条件2-8°C
产品应用用于制备重氮甲烷.
性质描述黄色结晶.熔点62°C.溶于醚,苯,氯仿,甲氯化碳,不溶于水.

MSDS等安全信息

GHS象形图
GHS符号GHS02 & GHS07;
注释: Flame & Exclamation mark
危险类别Self-react. C
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
皮肤致敏类别1
致癌性类别1A
急性毒性类别4(吸入)
急性毒性类别4(经皮)
警示词Danger(危险)
危险描述H242 |加热可能引起火灾.
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.
H317 |可能引起皮肤过敏反应.
H350 |可能致癌.
H332 |吸入有害.
H312 |皮肤接触有害.
防范说明P210-P234-P235-P240-P261-P264-P271-P272-P280-P302+P352-P304+P340-P305+P351+P338-P362+P364-P370+P378-P403-P403+P233-P405-P420-P501
危险等级4.1
UN编号3224.0
危险品标志E,Xi,Xn
包装等级III
安全声明15-26-35-36/37-36
危险类别码2-36/37/38-43-20/21/22
WGK Germany2

欧盟法规

ECHA物质C&L通报REACH预注册

上下游产品

p-toluenesulfonyl chloride methylamine cyclopentyl nitrite N-methyl-p-toluenesulfonylamidemethyl p-toluene sulfonate cis-1,2-Dimethyl-cycloheptan trans-1,2-Dimethylcycloheptan (Z)-potassium methanediazotate

合成工艺路线路线简述

合成目标产物 N-Methyl-N-Nitrosotoluene-4-Sulphonamide 主要起始原料 N-Methyl-P-Toluenesulfonamide
640-61-9 = 80-11-5
反应条件:1.1 Reagents: Sodium Nitrite,Hydrochloric Acid Solvents: Diethyl Ether,Water; 5 Min,0 °C; 4 H,Rt
标题:Controllable Z/e-Selective Synthesis Of α-Amino-Ketoximes From N-Nitrososulfonamides And Aryl Alkenes Under Neutral Conditions
作者:Yuan,Pan-Feng; Et Al
参考文献:Organic Chemistry Frontiers 日期:2021 卷标:8(20) 页码:5785-5792]

640-61-9 = 80-11-5
反应条件:1.1 Reagents: Sodium Nitrite,Hydrochloric Acid Solvents: Diethyl Ether,Water
标题:Photochemical Activities Of N-Nitroso Carboxamides And Sulfoximides And Their Application To Dna Cleavage
作者:Hwu,Jih Ru; Et Al
参考文献:Chemistry - A European Journal 日期:2009 卷标:15(35) 页码:8742-8750]

= 80-11-5
反应条件:1.1 -1.2 Reagents: Sodium Nitrite Solvents: Acetic Acid
标题:N-Methyl-N-Nitroso-P-Toluenesulfonamide
作者:Terao,Yoshiyasu; Et Al
参考文献:E-Eros Encyclopedia Of Reagents For Organic Synthesis 日期:2016 卷标:1 页码:1-2]

640-61-9 = 80-11-5
反应条件:1.1 Solvents: Acetic Acid,Water; Rt -> 115 °C; 115 °C -> 0 °C1.2 Reagents: Sodium Nitrite; 10 Min,0 °C; 1 H,0 °C
标题:Safe And Reliable Synthesis Of Diazoketones And Quinoxalines In A Continuous Flow Reactor
作者:Martin,Laetitia J.; Et Al
参考文献:Organic Letters 日期:2011 卷标:13(2) 页码:320-323]

22547-51-9 = 80-11-5
反应条件:1.1 Reagents: Nitrous Acid
标题:Carbonyl Regeneration From P-Toluenesulfonylhydrazones,N-Methyl-N-(P-Toluenesulfonyl)Hydrazones,And 2,4-Dinitrophenylhydrazones
作者:Caglioti,L.; Et Al
参考文献:Synthesis 日期:1979 卷标:(3) 页码:207-8]

63383-06-2 = 80-11-5
反应条件:1.1 Reagents: Sodium Nitrite Catalysts: Trifluoroacetic Acid
标题:Carbonyl Regeneration From P-Toluenesulfonylhydrazones,N-Methyl-N-(P-Toluenesulfonyl)Hydrazones,And 2,4-Dinitrophenylhydrazones
作者:Caglioti,L.; Et Al
参考文献:Synthesis 日期:1979 卷标:(3) 页码:207-8]

19816-88-7 = 80-11-5
反应条件:1.1 -2.1 Reagents: Sodium Nitrite Catalysts: Trifluoroacetic Acid
标题:Carbonyl Regeneration From P-Toluenesulfonylhydrazones,N-Methyl-N-(P-Toluenesulfonyl)Hydrazones,And 2,4-Dinitrophenylhydrazones
作者:Caglioti,L.; Et Al
参考文献:Synthesis 日期:1979 卷标:(3) 页码:207-8]

= 80-11-5
反应条件:1.1 -2.1 Reagents: Sodium Nitrite Catalysts: Trifluoroacetic Acid
标题:Carbonyl Regeneration From P-Toluenesulfonylhydrazones,N-Methyl-N-(P-Toluenesulfonyl)Hydrazones,And 2,4-Dinitrophenylhydrazones
作者:Caglioti,L.; Et Al
参考文献:Synthesis 日期:1979 卷标:(3) 页码:207-8]

7318-33-4 = 80-11-5
反应条件:1.1 -2.1 Reagents: Sodium Nitrite Catalysts: Trifluoroacetic Acid
标题:Carbonyl Regeneration From P-Toluenesulfonylhydrazones,N-Methyl-N-(P-Toluenesulfonyl)Hydrazones,And 2,4-Dinitrophenylhydrazones
作者:Caglioti,L.; Et Al
参考文献:Synthesis 日期:1979 卷标:(3) 页码:207-8]

= 80-11-5
反应条件:1.1 Solvents: Dimethylformamide,Water; 25 H,Rt2.1 Solvents: Acetic Acid,Water; Rt -> 115 °C; 115 °C -> 0 °C2.2 Reagents: Sodium Nitrite; 10 Min,0 °C; 1 H,0 °C
标题:Safe And Reliable Synthesis Of Diazoketones And Quinoxalines In A Continuous Flow Reactor
作者:Martin,Laetitia J.; Et Al
参考文献:Organic Letters 日期:2011 卷标:13(2) 页码:320-323]

56805-36-8 = 80-11-5
反应条件:1.1 Reagents: Trifluoroacetic Acid; 0 °C; 0 °C -> 23 °C; 1 H,23 °C1.2 Solvents: Acetic Acid; 23 °C -> 5 °C1.3 Reagents: Sodium Acetate,Sodium Nitrite,Sodium Chloride Solvents: Water; 15 Min,< 7 °C1.4 Solvents: Water; 5 Min,Cooled
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]

640-61-9 = 80-11-5
反应条件:1.1 Reagents: Sodium Nitrite,Hydrochloric Acid Solvents: Acetonitrile,Water; < 10 Min,< 30 °C
标题:Continuous Production Of The Diazomethane Precursor N-Methyl-N-Nitroso-P-Toluenesulfonamide: Batch Optimization And Transfer Into A Microreactor Setup
作者:Struempel,Michael; Et Al
参考文献:Organic Process Research & Development 日期:2009 卷标:13(5) 页码:1014-1021]

= 80-11-5
反应条件:1.1 Solvents: Acetonitrile,Water; 2 H,Rt1.2 Reagents: Sodium Hydroxide Solvents: Water; Rt1.3 Reagents: Acetic Acid,Sodium Nitrite Solvents: Water; 0 - 5 °C
标题:Continuous In-Situ Generation,Separation,And Reaction Of Diazomethane In A Dual-Channel Microreactor
作者:Maurya,Ram Awatar; Et Al
参考文献:Angewandte Chemie 日期:2011 卷标:50(26) 页码:5952-5955]

= 80-11-5
反应条件:1.1 Reagents: Sodium Hydroxide,Sodium Nitrite Solvents: Acetic Acid,Water
标题:P-Tolylsulfonylmethylnitrosamide
作者:De Boer,Th. J.; Et Al
参考文献:Organic Syntheses 日期:1954 卷标:34 页码:96-100]

15934-23-3 + 7783-99-5 = 80-11-5
反应条件:1.1 Solvents: Acetonitrile
标题:Reactions Of Imidoyl Chlorides With Silver Nitrite And Silver Nitrate. A Simple Synthesis Of N-Nitroso And N-Nitro Amides Using Imidate Ester Methodology
作者:De Carvalho,Emilia; Et Al
参考文献:Journal Of Chemical Research 日期:1985 卷标:(4) 页码:132-3]

63383-17-5 = 80-11-5
反应条件:1.1 Reagents: Sodium Nitrite Catalysts: Trifluoroacetic Acid
标题:Carbonyl Regeneration From P-Toluenesulfonylhydrazones,N-Methyl-N-(P-Toluenesulfonyl)Hydrazones,And 2,4-Dinitrophenylhydrazones
作者:Caglioti,L.; Et Al
参考文献:Synthesis 日期:1979 卷标:(3) 页码:207-8]

= 80-11-5
反应条件:1.1 Reagents: Sodium Nitrite Catalysts: Trifluoroacetic Acid
标题:Carbonyl Regeneration From P-Toluenesulfonylhydrazones,N-Methyl-N-(P-Toluenesulfonyl)Hydrazones,And 2,4-Dinitrophenylhydrazones
作者:Caglioti,L.; Et Al
参考文献:Synthesis 日期:1979 卷标:(3) 页码:207-8]

= 80-11-5
反应条件:1.1 Reagents: Sodium Nitrite Catalysts: Trifluoroacetic Acid
标题:Carbonyl Regeneration From P-Toluenesulfonylhydrazones,N-Methyl-N-(P-Toluenesulfonyl)Hydrazones,And 2,4-Dinitrophenylhydrazones
作者:Caglioti,L.; Et Al
参考文献:Synthesis 日期:1979 卷标:(3) 页码:207-8]

18303-04-3 + 80-48-8 = 80-11-5
反应条件:1.1 Reagents: Potassium Carbonate Solvents: Acetonitrile; 18 H,Rt -> 80 °C2.1 Reagents: Trifluoroacetic Acid; 0 °C; 0 °C -> 23 °C; 1 H,23 °C2.2 Solvents: Acetic Acid; 23 °C -> 5 °C2.3 Reagents: Sodium Acetate,Sodium Nitrite,Sodium Chloride Solvents: Water; 15 Min,< 7 °C2.4 Solvents: Water; 5 Min,Cooled
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]

41780-53-4 = 80-11-5
反应条件:1.1 -2.1 Reagents: Sodium Nitrite Catalysts: Trifluoroacetic Acid
标题:Carbonyl Regeneration From P-Toluenesulfonylhydrazones,N-Methyl-N-(P-Toluenesulfonyl)Hydrazones,And 2,4-Dinitrophenylhydrazones
作者:Caglioti,L.; Et Al
参考文献:Synthesis 日期:1979 卷标:(3) 页码:207-8]

24424-99-5 + 70-55-3 = 80-11-5
反应条件:1.1 Reagents: Triethylamine Catalysts: 4-(Dimethylamino)Pyridine Solvents: Dichloromethane; 25 Min,Rt; 2 H,Rt2.1 Reagents: Potassium Carbonate Solvents: Acetonitrile; 18 H,Rt -> 80 °C3.1 Reagents: Trifluoroacetic Acid; 0 °C; 0 °C -> 23 °C; 1 H,23 °C3.2 Solvents: Acetic Acid; 23 °C -> 5 °C3.3 Reagents: Sodium Acetate,Sodium Nitrite,Sodium Chloride Solvents: Water; 15 Min,< 7 °C3.4 Solvents: Water; 5 Min,Cooled
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]

= 80-11-5
反应条件:1.1 Reagents: Triethylamine Catalysts: Trimethylammonium Chloride Solvents: Toluene; Cooled1.2 Solvents: Toluene; 10 Min,Cooled; 1 H,0 °C2.1 Reagents: Potassium Carbonate Solvents: Acetonitrile; 18 H,Rt -> 80 °C3.1 Reagents: Trifluoroacetic Acid; 0 °C; 0 °C -> 23 °C; 1 H,23 °C3.2 Solvents: Acetic Acid; 23 °C -> 5 °C3.3 Reagents: Sodium Acetate,Sodium Nitrite,Sodium Chloride Solvents: Water; 15 Min,< 7 °C3.4 Solvents: Water; 5 Min,Cooled
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]

= 80-11-5
反应条件:1.1 Reagents: Ammonium Hydroxide Solvents: Ethanol,Tetrahydrofuran,Water; 5 Min,Rt; 1 D,Rt2.1 Reagents: Triethylamine Catalysts: 4-(Dimethylamino)Pyridine Solvents: Dichloromethane; 25 Min,Rt; 2 H,Rt3.1 Reagents: Potassium Carbonate Solvents: Acetonitrile; 18 H,Rt -> 80 °C4.1 Reagents: Trifluoroacetic Acid; 0 °C; 0 °C -> 23 °C; 1 H,23 °C4.2 Solvents: Acetic Acid; 23 °C -> 5 °C4.3 Reagents: Sodium Acetate,Sodium Nitrite,Sodium Chloride Solvents: Water; 15 Min,< 7 °C4.4 Solvents: Water; 5 Min,Cooled
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

甲基(甲苯磺酰基)酰胺置于nitrosonium Perchlorate体系中,用乙腈作为反应溶剂,化学反应生成 N-甲基-N-亚硝基对甲苯磺酰胺
参考文献:N-甲基-N-亚硝基苯磺酰胺在乙腈中n-No键解离能的测定及其在no转移机理分析中的应用
标题:N-甲基-N-亚硝基苯磺酰胺在乙腈中n-No键解离能的测定及其在no转移机理分析中的应用
摘要:七种取代的 N-甲基-N-亚硝基苯磺酰胺(简称 G-Mnbs,G = P-och(3),P-Ch(3),Ph,P-Cl,P-Br,2,5-2Cl,M-No(2)) 在乙腈溶液中首次使用滴定量热法和相对热力学循环根据赫斯定律进行评估.结果表明,G-Mnbs 在乙腈溶液中的异裂和均裂 N-No 键解离能的能量标度分别涵盖了中性 G-Mnbs 的 44.3 至 49.5 和 33.0 至 34.9 Kcal/mol 的范围,其中表明 N-甲基-N-亚硝基苯磺酰胺比释放 No 阳离子 (No(+)) 更容易释放 No 自由基 (No(*)).乙腈溶液中七个 G-Mnbs 自由基阴离子的异裂和均裂 (N-No)(-)(*) 键解离能的估计给出了-15.8 至-12.9 和-3.1 至 1.8 Kcal/mol 的能量范围对于 (N-No)(-)(*) 键均裂和异裂,这意示 G-Mnbs
DOI:10.1021/ja0443676