3-vinylmercapto-propylamine | 64433-18-7

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 3-vinylmercapto-propylamine
• 英文别名: 1-Amino-3-vinylmercapto-propan；3-Vinylmercapto-propylamin；(3-Amino-propyl)-vinyl-sulfid；(3-Amino-propyl)-vinylsulfid；3-Ethenylsulfanylpropan-1-amine
• CAS: 64433-18-7
• 化学式: C₅H₁₁NS
• mdl: MFCD19205114
• 分子量: 117.215
• InChiKey: FHBDOBDDORWWAJ-UHFFFAOYSA-N

物化性质

• 沸点：
  68 °C(Press: 7 Torr)
• 密度：
  0.9765 g/cm3(Temp: 25 °C)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  7
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  51.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3-Aminopropyl carbamimidothioate;hydrochloride 、 乙炔 在 sodium hydroxide 作用下， 以 乙二醇二甲醚 为溶剂， 生成 3-vinylmercapto-propylamine
  参考文献：
  名称：

  Vinyl Sulfides. II. Aminoalkyl Vinyl Sulfides

  摘要：

  DOI：

  10.1021/jo01065a072

文献信息

• Amino-containing vinyl sulfides
  申请人：ROHM & HAAS

  公开号：US02816094A1

  公开（公告）日：1957-12-10

  In examples a copolymer is prepared from N.N. diethylaminoethyl vinyl sulphide, acrylonitrile, and ethyl acrylate. The copolymer may be used in the form of an aqueous dispersion for coating tiles, fibre boards and pressed boards.ALSO:Vinyl sulphides (thio ethers) having an amino group, of general formula CH2=CH-S-A-N-R1R2 where A represents a phenylene group, a phenylene group having non-functional ring substituents, or an alkylene group having at least two carbon atoms between the nitrogen and sulphur atoms, and R1 and R2 together represent a saturated divalent aliphatic chain with which the nitrogen atom forms a heterocyclic group having five or six cyclic atoms, or R1 and R2 each represent hydrogen or a C1-C5 alkyl group, are prepared by reacting acetylene and an amino-containing thiol of the formula R1R2N-A-S-H together at elevated temperature and pressure, in the presence of a strongly basic catalyst, such as potassium hydroxide, sodium ethoxide, potassium ethoxide, or potassium butoxide (1 to 10% by weight of the thiol), and an organic solvent, e.g. C1-C5 alkanols, e.g. ethoxyethanol, butoxyethanol, ethoxy ethoxy-ethanol or butoxyethoxy-ethanol, or ether alcohols alone or with, e.g., the dimethyl ether of ethylene glycol or diethyl acetal. The organic solvent used is one which is a solvent for the thiol and for the catalyst. The acetylene is passed into the solution under pressure and heated to 100-200 DEG C. at 100-700 p.s.i.g. Suitable aminocontaining thiols are substituted or unsubstituted aminobenzenethiols, aminotoluenethiols or aminoalkanethiols. Examples are given of the reaction between acetylene in the presence of potassium butoxide and n-butyl alcohol and (1) 2-aminobenzenethiol to produce 2-aminophenyl vinyl sulphide; (2) 2-aminoethanethiol to produce 2-aminoethyl vinyl sulphide; (3) b -N-N-dimethylaminoethanethiol to produce N,N-dimethylaminoethyl vinyl sulphide. Examples also describe the production of 2-morpholinoethyl vinyl sulphide from 2-morpholinoethanethiol, 2-piperidinoethyl vinyl sulphide from 2 - piperidinoethanethiol, 2 - pyrrolidinoethyl vinyl sulphide from 2-pyrrolidinoethanethiol, pyrrolidinoisopropyl vinyl sulphide from pyrrolidinoisopropanethiol, and acetylene in the presence of potassium hydroxide, butanol, and methyl formal. Other starting materials specified are N,N-dibutyl aminobenzenethiol, b -aminoethanethiol, diethyl-aminoethanethiol, dibutylaminoethanethiol, morpholinopropanethiol, pyrrolidinobutanethiol, aminobutanethiol, dimethylaminobutanethiol, diethylaminohexanethiol, dimethylaminododecanethiol, and o -aminododecanethiol.ALSO:Compounds of the general formula CH2 = CH-S-A-NR1R2 where A is a phenylene group, a phenylene group having non-functional ring substituents or an alkylene group having at least two carbon atoms between the nitrogen and sulphur atoms, and either R1 and R2 together represent a saturated divalent aliphatic chain with which the nitrogen atom forms a heterocyclic group having five or six cyclic atoms, or R1 and R2 each represent hydrogen or C1-C5 alkyl group, are subjected to polymerization treatment to form homopolymers or copolymers. The amino-containing vinyl sulphides form homopolymers under the influence of cationic agents in about molar proportions or more, e.g. boron trifluoride, and its co-ordination complexes with oxygenated organic compounds, such as ethers, alcohols, aldehydes and carboxylic acids, zinc chloride, or stannic chloride, or in the presence of relatively small amounts of azo free-radical catalysts such as azodiisobutyronitrile, dimethyl azodiisobutyrate or azodiisobutyramide. Examples are given of the polymerization of 2-aminoethyl vinyl sulphide, 2-aminophenyl vinyl sulphide and N,N-dimethylaminoethyl vinyl sulphide, and of the copolymerization of 3-aminopropyl vinyl sulphide and sulphur dioxide. The poly - (N,N - dimethylaminoethyl vinyl sulphide) is quaternized with hexamethylene dibromide to give an ion-exchange resin. The compounds of the invention may be copolymerized with, e.g., acrylonitrile, acrylamide, methyl, ethyl, butyl, octyl, dodecyl, methoxyethyl or benzyl acrylates, methacrylonitrile, methacrylamide, methyl, ethyl, butyl, cyclohexyl, benzyl, butoxyethyl, octyl or dodecyl methacrylate, ethylene diacrylate or dimethacrylate, vinyloxyethyl-acrylate or methacrylate, allyl acrylate or methacrylate, ethyl, butyl, octyl, ethoxyethyl, and ureidoisobutyl vinyl ethers, ethyl vinyloxyethylcarbamate, N-vinylpyrrolidone, alkyl vinyl sulphides, N-vinyl ethylene urea, N-vinyl succinimide, N-vinylphthalamide, styrene, p-methylstyrene, p-chlorostyrene, vinyltoluene, divinylbenzene, trivinylbenzene, vinyl acetate, vinyl propionate, dimethyl or dibutyl itaconate, dialkyl maleates, mesaconates and nitraconates. Examples are given of copolymers of b -aminoethyl vinyl sulphide and divinylbenzene (an ion-exchange resin), N,N-dimethylaminoethyl vinyl sulphide and N-vinylpyrrolidone, and of N,N-diethylaminoethyl vinyl sulphide, acrylonitrile and ethyl acrylate. The homopolymers may be used as additives to cellulose acetate spinning dopes.ALSO:A pesticidal composition comprises 2-aminophenyl vinyl sulphide incorporated in a dust in proportions of 1, 3 and 5%.

  在示例中，从N.N.二乙氨基乙烯硫醚、丙烯腈和丙烯酸乙酯制备了共聚物。 该共聚物可以以水分散形式用于涂覆瓷砖、纤维板和压制板。另外，含有氨基的乙烯硫醚（硫醚）的通用公式为CH2=CH-S-A-N-R1R2，其中A表示苯基、具有非功能性环取代基的苯基，或者氮和硫原子之间至少有两个碳原子的烷基基团，R1和R2一起表示与氮原子形成具有五个或六个环原子的杂环基团的饱和二价脂肪链，或者R1和R2分别表示氢或C1-C5烷基基团，通过在高温高压下，在强碱性催化剂的存在下（例如氢氧化钾、乙氧基钠、乙氧基钾或丁氧基钾（硫醚重量的1至10％））和有机溶剂（例如C1-C5烷醇，如乙氧乙醇、丁氧乙醇、乙氧乙氧乙醇或丁氧乙氧乙醇）的存在下，通过将乙炔和具有R1R2N-A-S-H公式的含氨硫醇反应制备。 使用的有机溶剂是对硫醇和催化剂的溶剂。 乙炔在压力下通入溶液中，并加热至100-200摄氏度，在100-700磅力/平方英寸的压力下。 适用的含氨硫醇是取代或未取代的氨基苯硫醇、氨基甲苯硫醇或氨基烷硫醇。 例如，在存在氢氧化钾和正丁醇的情况下，给出了乙炔与（1）2-氨基苯硫醇反应以产生2-氨基苯基乙烯硫醚；（2）2-氨基乙硫醇反应以产生2-氨基乙基乙烯硫醚；（3）b-N-N-二甲基氨基乙硫醇反应以产生N,N-二甲基氨基乙基乙烯硫醚。 例如还描述了从2-吗啉乙硫醇制备2-吗啉基乙基乙烯硫醚，从2-哌啶乙硫醇制备2-哌啶基乙基乙烯硫醚，从2-吡咯烷基乙硫醇制备2-吡咯烷基乙基乙烯硫醚，从吡咯烷基异丙基硫醇制备吡咯烷基异丙基乙烯硫醚，以及乙炔在氢氧化钾、丁醇和甲醛存在下的情况下。 指定的其他起始材料包括N,N-二丁基氨基苯硫醇、b-氨基乙硫醇、二乙基氨基乙硫醇、二丁基氨基乙硫醇、吗啉丙硫醇、吡咯丁硫醇、氨基丁硫醇、二甲基氨基丁硫醇、二乙基氨基己硫醇、二甲基氨基十二烷硫醇和o-氨基十二烷硫醇。 此外，通用公式 =CH-S-A-NR1R2的化合物，其中A是苯基、具有非功能性环取代基的苯基或者氮和硫原子之间至少有两个碳原子的烷基基团，R1和R2要么一起表示与氮原子形成具有五个或六个环原子的杂环基团的饱和二价脂肪链，要么R1和R2分别表示氢或C1-C5烷基基团，经过聚合处理形成均聚物或共聚物。 含氨基的乙烯硫醚在阳离子剂的影响下形成均聚物，例如三氟化硼及其与含氧有机化合物（例如醚、醇、醛和羧酸）、氯化锌或氯化锡的配位络合物，或在相对少量的自由基偶氮催化剂的存在下（例如偶氮异丁腈、偶氮异丁酸二酯或偶氮异丁酰胺）。 给出了2-氨基乙基乙烯硫醚、2-氨基苯基乙烯硫醚和N,N-二甲基氨基乙基乙烯硫醚的聚合反应示例，以及3-氨基丙基乙烯硫醚和二氧化硫的共聚合反应。 聚N,N-二甲基氨基乙基乙烯硫醚与六亚甲基二溴化合物季铵化，形成离子交换树脂。 本发明的化合物可以与丙烯腈、丙烯酰胺、甲基、乙基、丁基、辛基、十二烷基、甲氧基乙基或苄基丙烯酸酯、甲基丙烯腈、甲基丙烯酰胺、甲基、乙基、丁基、环己基、苄基、乙氧基乙基、辛基或十二烷基甲基丙烯酸酯、乙烯二丙烯酸酯或二甲基丙烯酸酯、乙烯氧基乙基丙烯酸酯或甲基丙烯酸酯、烯丙酸酯或甲基丙烯酸酯、乙基、丁基、辛基、乙氧基乙基、尿素异丁基乙烯醚、乙基乙烯氧乙基碳酸酯、N-乙烯吡咯酮、烷基乙烯硫醚、N-乙烯乙烯脲、N-乙烯丁二酰亚胺、N-乙烯邻苯二甲酰胺、苯乙烯、对甲基苯乙烯、对氯苯乙烯、甲苯乙烯、二乙烯基苯、三乙烯基苯、乙酸乙烯酯、丙酸乙烯酯、顺丁烯二酸二乙酯、二烷基马来酸酯、丙烯酸马来酸酯和丙烯酸硝基酯等共聚。 给出了b-氨基乙基乙烯硫醚和二乙烯基苯（离子交换树脂）、N,N-二甲基氨基乙基乙烯硫醚和N-乙烯吡咯酮的共聚物，以及N,N-二乙氨基乙基乙烯硫醚、丙烯腈和丙烯酸乙酯的共聚物的示例。 这些均聚物可以用作纤维素醋酸纤维纺丝浆的添加剂。 此外，一种杀虫剂组合物包括以1％、3％和5％的比例掺入的2-氨基苯基乙烯硫醚。