{"id":48880,"date":"2024-05-17T15:00:49","date_gmt":"2024-05-17T07:00:49","guid":{"rendered":"http:\/\/www.newtopchem.com\/archives\/48880"},"modified":"2024-05-17T15:00:49","modified_gmt":"2024-05-17T07:00:49","slug":"4-hydroxy-2-mercapto-6-methylpyrimidine","status":"publish","type":"post","link":"http:\/\/www.newtopchem.com\/archives\/48880","title":{"rendered":"4-hydroxy-2-mercapto-6-methylpyrimidine","gt_translate_keys":[{"key":"rendered","format":"text"}]},"content":{"rendered":"<p><img decoding=\"async\" loading=\"lazy\" class=\"alignnone size-full wp-image-48879\" src=\"http:\/\/www.newtopchem.com\/wp-content\/uploads\/2024\/05\/aa6a0f42323040f7a82a81ee04ba839a.gif\" width=\"146\" height=\"227\" alt=\"4-hydroxy-2-mercapto-6-methylpyrimidine structural formula\" \/><\/p>\n<p>Structural formula<\/p>\n<table class=\"summary-table table table-striped table-bordered\">\n<col width=\"90\" \/>\n<tbody>\n<tr>\n<th scope=\"row\">Business number<\/th>\n<td>0173<\/td>\n<\/tr>\n<tr>\n<th scope=\"row\">Molecular formula<\/th>\n<td>C5H6N2OS<\/td>\n<\/tr>\n<tr>\n<th scope=\"row\">Molecular weight<\/th>\n<td>142.18<\/td>\n<\/tr>\n<tr>\n<th scope=\"row\">label<\/th>\n<td>\n<p>                         6-Methyl-2-thiouracil,<\/p>\n<p>                         MZU<\/p>\n<\/td>\n<\/tr>\n<\/tbody>\n<\/table>\n<ul class=\"nav nav-tabs\">\n<li class=\"active\"><a href=\"#bh\">Numbering system<\/a><\/li>\n<li><a href=\"#wx\">Physical property data<\/a><\/li>\n<li><a href=\"#dl\">Toxicological data<\/a><\/li>\n<li><a href=\"#st\">Ecological data<\/a><\/li>\n<li><a href=\"#fz\">Molecular structure data<\/a><\/li>\n<li><a href=\"#js\">Computing chemical data<\/a><\/li>\n<li class=\"dropdown pull-right\">\n                     <a href=\"\" class=\"dropdown-toggle\">More <span class=\"caret\"><\/span><\/a><\/p>\n<ul class=\"dropdown-menu\" role=\"menu\">\n<li><a href=\"#xz\">Properties and Stability<\/a><\/li>\n<li><a href=\"#zc\">Storage method<\/a><\/li>\n<li><a href=\"#hc\">Synthesis method<\/a><\/li>\n<li><a href=\"#yt\">Purpose<\/a><\/li>\n<\/ul>\n<\/li>\n<\/ul>\n<h2 id=\"bh\">Numbering system<\/h2>\n<p><b>CAS number:<\/b>56-04-2<\/p>\n<p><b>MDL number:<\/b>MFCD00006040<\/p>\n<p><b>EINECS number:<\/b>200-252-3<\/p>\n<p><b>RTECS number:<\/b>YR0875000<\/p>\n<p><b>BRN number:<\/b>115648<\/p>\n<p><b>PubChem number:<\/b>24895573<\/p>\n<h2 id=\"wx\">Physical property data<\/h2>\n<p>\n     <P class=\"MsoNormal\" align=\"left\"><SPAN><SPAN>1.<SPAN> <\/SPAN>  <\/SPAN><\/SPAN><SPAN>Character:<\/SPAN><SPAN>White crystal.  in<\/SPAN><SPAN>326-331<\/SPAN><SPAN>\u2103 decomposition.  Saturated aqueous solution is neutral or slightly acidic to litmus.  Odorless, bitter, easy to sublime.  <\/SPAN><SPAN>  <\/SPAN><\/P><br \/>\n <P class=\"MsoNormal\" align=\"left\"><SPAN><SPAN>2.<SPAN> <\/SPAN>  <\/SPAN><\/SPAN><SPAN>Density (<\/SPAN><SPAN>g\/mL,25\/4<\/SPAN><SPAN>\u2103<\/SPAN><SPAN>): <\/SPAN><SPAN> <\/SPAN><SPAN>Unknown  OK<\/SPAN><SPAN><\/SPAN><\/P><br \/>\n <P class=\"MsoNormal\" align=\"left\"><SPAN><SPAN>3.<SPAN> <\/SPAN>  <\/SPAN><\/SPAN><SPAN>Relative vapor density (<\/SPAN><SPAN>g\/mL,<\/SPAN><SPAN>AIR<\/SPAN><SPAN>=1<\/SPAN><SPAN>): Undetermined<\/SPAN><SPAN><\/SPAN><\/P><br \/>\n <P class=\"MsoNormal\" align=\"left\"><SPAN><SPAN>4.<SPAN> <\/SPAN>  <\/SPAN><\/SPAN><SPAN>Melting point (<\/SPAN><SPAN>\u00baC<\/SPAN><SPAN>):<\/SPAN><SPAN>330<\/SPAN><SPAN>\u2103<\/SPAN><SPAN><\/SPAN><\/P><br \/>\n <P class=\"MsoNormal\" align=\"left\"><SPAN><SPAN>5.<SPAN> <\/SPAN>  <\/SPAN><\/SPAN><SPAN>Boiling point (<\/SPAN><SPAN>\u00baC,<\/SPAN><SPAN>Normal pressure): Undetermined<\/SPAN><SPAN><\/SPAN><\/P><br \/>\n <P class=\"MsoNormal\" align=\"left\"><SPAN><SPAN>6.<SPAN> <\/SPAN>  <\/SPAN><\/SPAN><SPAN>Boiling point (<\/SPAN><SPAN>\u00baC,<\/SPAN><SPAN> 1.60kPa<\/SPAN><SPAN>): <\/SPAN><SPAN> <\/SPAN><SPAN>Undetermined.<\/SPAN><SPAN><\/SPAN><\/P><br \/>\n <P class=\"MsoNormal\" align=\"left\"><SPAN><SPAN>7.<SPAN> <\/SPAN>  <\/SPAN><\/SPAN><SPAN>Refractive index: Undetermined<\/SPAN><SPAN><\/SPAN><\/P><br \/>\n <P class=\"MsoNormal\" align=\"left\"><SPAN><SPAN>8.<SPAN> <\/SPAN>  <\/SPAN><\/SPAN><SPAN>Flash Point (<\/SPAN><SPAN>\u00baC<\/SPAN><SPAN>): Undetermined<\/SPAN><SPAN><\/SPAN><\/P><br \/>\n <P class=\"MsoNormal\" align=\"left\"><SPAN><SPAN>9.<SPAN> <\/SPAN>  <\/SPAN><\/SPAN><SPAN>Specific optical rotation (<\/SPAN><SPAN>\u00ba<\/SPAN><SPAN>): Undetermined<\/SPAN><SPAN><\/SPAN><\/P><br \/>\n <P class=\"MsoNormal\" align=\"left\"><SPAN><SPAN>10.<SPAN> <\/SPAN>  <\/SPAN><\/SPAN><SPAN>Autoignition point or ignition temperature (<\/SPAN><SPAN>\u00baC<\/SPAN><SPAN>): Undetermined<\/SPAN><SPAN><\/SPAN><\/P><br \/>\n <P class=\"MsoNormal\" align=\"left\"><SPAN><SPAN>11.<SPAN> <\/SPAN>  <\/SPAN><\/SPAN><SPAN>Vapor pressure (<\/SPAN><SPAN>kPa,25\u00baC<\/SPAN><SPAN>): Undetermined<\/SPAN><SPAN>  <\/SPAN><\/P><br \/>\n <P class=\"MsoNormal\" align=\"left\"><SPAN><SPAN>12.<SPAN> <\/SPAN>  <\/SPAN><\/SPAN><SPAN>Saturated vapor pressure (<\/SPAN><SPAN>kPa,60\u00baC<\/SPAN><SPAN>): Undetermined<\/SPAN><SPAN><\/SPAN><\/P><br \/>\n <P class=\"MsoNormal\" align=\"left\"><SPAN><SPAN>13.<SPAN> <\/SPAN>  <\/SPAN><\/SPAN><SPAN>Heat of combustion (<\/SPAN><SPAN>KJ\/mol<\/SPAN><SPAN>): Undetermined<\/SPAN><SPAN><\/SPAN><\/P><br \/>\n <P class=\"MsoNormal\" align=\"left\"><SPAN><SPAN>14.<SPAN> <\/SPAN>  <\/SPAN><\/SPAN><SPAN>Critical temperature (<\/SPAN><SPAN>\u00baC<\/SPAN><SPAN>): Undetermined<\/SPAN><SPAN><\/SPAN><\/P><br \/>\n <P class=\"MsoNormal\" align=\"left\"><SPAN><SPAN>15.<SPAN> <\/SPAN>  <\/SPAN><\/SPAN><SPAN>Critical pressure (<\/SPAN><SPAN>KPa<\/SPAN><SPAN>): Undetermined<\/SPAN><SPAN><\/SPAN><\/P><br \/>\n <P class=\"MsoNormal\" align=\"left\"><SPAN><SPAN>16.<SPAN> <\/SPAN>  <\/SPAN><\/SPAN><SPAN>Oil and water (octanol<\/SPAN><SPAN>\/<\/SPAN><SPAN>Log value of water) partition coefficient: Undetermined<\/SPAN><SPAN><\/SPAN><\/P><br \/>\n <P class=\"MsoNormal\" align=\"left\"><SPAN><SPAN>17.<SPAN> <\/SPAN>  <\/SPAN><\/SPAN><SPAN>Explosion limit (<\/SPAN><SPAN>%,V\/V<\/SPAN><SPAN>): Undetermined<\/SPAN><SPAN><\/SPAN><\/P><br \/>\n <P class=\"MsoNormal\" align=\"left\"><SPAN><SPAN>18.<SPAN> <\/SPAN>  <\/SPAN><\/SPAN><SPAN>Lower explosion limit (<\/SPAN><SPAN>%,V\/V<\/SPAN><SPAN>): Undetermined<\/SPAN><SPAN><\/SPAN><\/P><br \/>\n <P class=\"MsoNormal\" align=\"left\"><SPAN><SPAN>19.<SPAN> <\/SPAN>  <\/SPAN><\/SPAN><SPAN>Solubility:<\/SPAN><SPAN>Easily soluble in ammonia solution and sodium hydroxide solution, slightly soluble in alcohol and acetone, very slightly soluble in water and ether, insoluble in benzene and chloroform.  <\/SPAN><SPAN><\/SPAN>  <\/P>\n     <\/p>\n<h2 id=\"dl\">Toxicological data<\/h2>\n<p>\n     None\n     <\/p>\n<h2 id=\"st\">Ecological data<\/h2>\n<p>\n     None\n     <\/p>\n<h2 id=\"fz\">Molecular structure data<\/h2>\n<p>\n     <P class=\"MsoNormal\" align=\"left\"><SPAN> <\/SPAN><\/P><br \/>\n <P class=\"MsoNormal\" align=\"left\"><SPAN><SPAN>1. <SPAN> <\/SPAN><\/SPAN><\/SPAN><SPAN>Molar refractive index: <\/SPAN>  <SPAN>37.31<\/SPAN><\/P><br \/>\n <P class=\"MsoNormal\" align=\"left\"><SPAN><SPAN>2. <SPAN><\/SPAN><\/SPAN><\/SPAN><SPAN>Molar volume (<\/SPAN><SPAN>m<SUP>3<\/SUP>\/  mol<\/SPAN><SPAN>):<\/SPAN><SPAN>103.1<\/SPAN><\/P><br \/>\n <P class=\"MsoNormal\" align=\"left\"><SPAN><SPAN>3. <SPAN> <\/SPAN><\/SPAN><\/SPAN><SPAN>isotonic specific volume (<\/SPAN><SPAN>90.2K<\/SPAN><SPAN>):<\/SPAN><SPAN>296.7<\/SPAN><\/P><br \/>\n <P class=\"MsoNormal\" align=\"left\"><SPAN><SPAN>4. <SPAN> <\/SPAN><\/SPAN><\/SPAN><SPAN>Surface Tension (<\/SPAN><SPAN>dyne\/cm<\/SPAN><SPAN>):<\/SPAN><SPAN>68.3<\/SPAN><\/P><br \/>\n <P class=\"MsoNormal\" align=\"left\"><SPAN><SPAN>5. <SPAN> <\/SPAN><\/SPAN><\/SPAN><SPAN>Polarizability<\/SPAN><SPAN>\uff08<\/SPAN><SPAN>10<SUP>-24<\/SUP>cm<SUP>3<\/SUP><\/SPAN><SPAN>):<\/SPAN><SPAN>14.79<\/SPAN><\/P><br \/>\n <P class=\"MsoNormal\" align=\"left\"><SPAN><SPAN> <\/SPAN><\/SPAN><\/P>\n     <\/p>\n<h2 id=\"js\">Compute chemical data<\/h2>\n<p>\n     <P class=\"MsoNormal\" align=\"left\"><SPAN><SPAN>1. <SPAN> <\/SPAN><\/SPAN><\/SPAN>  <SPAN>Reference value for hydrophobic parameter calculation (<SPAN>XlogP<\/SPAN>):<SPAN>-0.2<\/SPAN><\/SPAN><SPAN><\/SPAN><\/P><br \/>\n <P class=\"MsoNormal\" align=\"left\"><SPAN><SPAN>2. <SPAN> <\/SPAN><\/SPAN><\/SPAN><SPAN>Number of hydrogen bond donors: <SPAN>2<\/SPAN><\/SPAN><SPAN><\/SPAN><\/P><br \/>\n <P class=\"MsoNormal\" align=\"left\"><SPAN><SPAN>3. <SPAN> <\/SPAN><\/SPAN><\/SPAN>  <SPAN>Number of hydrogen bond acceptors: <SPAN>1<\/SPAN><\/SPAN><SPAN><\/SPAN><\/P><br \/>\n <P class=\"MsoNormal\" align=\"left\"><SPAN><SPAN>4. <SPAN> <\/SPAN><\/SPAN><\/SPAN>  <SPAN>Number of rotatable chemical bonds: <SPAN>0<\/SPAN><\/SPAN>  <SPAN><\/SPAN><\/P><br \/>\n <P class=\"MsoNormal\" align=\"left\"><SPAN><SPAN>5. <SPAN> <\/SPAN><\/SPAN><\/SPAN>  <SPAN>Number of tautomers: <SPAN>6<\/SPAN><\/SPAN><SPAN><\/SPAN><\/P><br \/>\n <P class=\"MsoNormal\" align=\"left\"><SPAN><SPAN>6. <SPAN> <\/SPAN><\/SPAN><\/SPAN>  <SPAN>Topological molecular polar surface area (<SPAN>TPSA<\/SPAN>):<SPAN>41.1<\/SPAN><\/SPAN><SPAN><\/SPAN><\/P><br \/>\n <P class=\"MsoNormal\" align=\"left\"><SPAN><SPAN>7. <SPAN> <\/SPAN><\/SPAN><\/SPAN>  <SPAN>Number of heavy atoms: <SPAN>9<\/SPAN><\/SPAN><SPAN><\/SPAN><\/P><br \/>\n <P class=\"MsoNormal\" align=\"left\"><SPAN><SPAN>8. <SPAN> <\/SPAN><\/SPAN><\/SPAN>  <SPAN>Surface charge: <SPAN>0<\/SPAN><\/SPAN><SPAN>  <\/SPAN><\/P><br \/>\n <P class=\"MsoNormal\" align=\"left\"><SPAN><SPAN>9. <SPAN> <\/SPAN><\/SPAN><\/SPAN><SPAN>Complexity: <SPAN>197<\/SPAN><\/SPAN><SPAN><\/SPAN><\/P><br \/>\n <P class=\"MsoNormal\" align=\"left\"><SPAN><SPAN>10. <\/SPAN><\/SPAN><SPAN>Number of isotope atoms: <SPAN>0<\/SPAN><\/SPAN><\/P><br \/>\n <P class=\"MsoNormal\" align=\"left\"><SPAN><SPAN>11. <\/SPAN><\/SPAN><SPAN>Determine the number of atomic stereocenters: <SPAN>0<\/SPAN><\/SPAN><\/P><br \/>\n <P class=\"MsoNormal\" align=\"left\"><SPAN><SPAN>12. <\/SPAN><\/SPAN><SPAN>The number of uncertain atomic stereocenters: <SPAN>0<\/SPAN><\/SPAN><\/P><br \/>\n <P class=\"MsoNormal\" align=\"left\"><SPAN><SPAN>13. <\/SPAN><\/SPAN><SPAN>Determine the number of stereocenters of chemical bonds: <SPAN>0<\/SPAN><\/SPAN><\/P><br \/>\n <P class=\"MsoNormal\" align=\"left\"><SPAN><SPAN>14. <\/SPAN><\/SPAN><SPAN>Uncertain number of chemical bond stereocenters: <SPAN>0<\/SPAN><\/SPAN><\/P><br \/>\n <P class=\"MsoNormal\" align=\"left\"><SPAN><SPAN>15. <\/SPAN><\/SPAN><SPAN>Number of covalent bond units: <SPAN>1<\/SPAN><\/SPAN><\/P>\n     <\/p>\n<h2 id=\"xz\">Properties and stability<\/h2>\n<p>\n     None\n     <\/p>\n<h2 id=\"zc\">Storage method<\/h2>\n<p>\n     None\n     <\/p>\n<h2 id=\"hc\">Synthesis method<\/h2>\n<p>\n     <SPAN><SPAN>It is derived from the reaction of ethyl acetoacetate and thiourea.  Dissolve thiourea in sodium hydroxide solution, add ethyl acetoacetate dropwise, and control the temperature at <SPAN>37<\/SPAN><\/SPAN><SPAN>\u2103<\/SPAN><\/SPAN><SPAN>below.  After reacting <SPAN>2h<\/SPAN>, add water and activated carbon, stir at <SPAN>70-80<\/SPAN><\/SPAN><SPAN>\u2103<\/SPAN><SPAN>Decolorization<SPAN>  0.5h<\/SPAN>.  Filter, acidify the filtrate with hydrochloric acid to <SPAN>pH4-5<\/SPAN>, cool to room temperature, filter and wash.  The filter cake is recrystallized with water to obtain the finished product.  The yield is <SPAN>66%<\/SPAN>.  During production, ethyl acetoacetate and thiourea can also be mixed first, and then sodium oxide solution is added dropwise; anhydrous sodium carbonate can also be used instead of sodium hydroxide, and the yield is roughly the same.  <SPAN><\/SPAN><\/SPAN>\n     <\/p>\n<h2 id=\"yt\">Purpose<\/h2>\n<p>\n     <SPAN>Intermediate of cardiovascular drug dipyridamole<\/SPAN>\n     <\/p>\n<p>     extended-reading:<a href=\"https:\/\/www.bdmaee.net\/cas-818-08-6\/\">https:\/\/www.bdmaee.net\/cas-818-08-6\/<\/a><\/br>extended-reading:<a href=\"https:\/\/www.newtopchem.com\/archives\/42992\">https:\/\/www.newtopchem.com\/archives\/42992<\/a><\/br>extended-reading:<a href=\"https:\/\/www.bdmaee.net\/dibutyl-tin-bis-1-thioglycerol\/\">https:\/\/www.bdmaee.net\/dibutyl-tin-bis-1-thioglycerol\/<\/a><\/br>extended-reading:<a href=\"https:\/\/www.bdmaee.net\/toyocat-te-tertiary-amine-catalyst-tosoh\/\">https:\/\/www.bdmaee.net\/toyocat-te-tertiary-amine-catalyst-tosoh\/<\/a><\/br>extended-reading:<a href=\"https:\/\/www.bdmaee.net\/dinbutyltindichloride\/\">https:\/\/www.bdmaee.net\/dinbutyltindichloride\/<\/a><\/br>extended-reading:<a href=\"https:\/\/www.cyclohexylamine.net\/metal-catalyst-heat-sensitive-metal-catalyst\/\">https:\/\/www.cyclohexylamine.net\/metal-catalyst-heat-sensitive-metal-catalyst\/<\/a><\/br>extended-reading:<a href=\"https:\/\/www.newtopchem.com\/archives\/44515\">https:\/\/www.newtopchem.com\/archives\/44515<\/a><\/br>extended-reading:<a href=\"https:\/\/www.bdmaee.net\/n-dimethylcyclohexylamine\/\">https:\/\/www.bdmaee.net\/n-dimethylcyclohexylamine\/<\/a><\/br>extended-reading:<a href=\"https:\/\/www.bdmaee.net\/niax-a-2420-foaming-catalyst-momentive\/\">https:\/\/www.bdmaee.net\/niax-a-2420-foaming-catalyst-momentive\/<\/a><\/br>extended-reading:<a href=\"https:\/\/www.newtopchem.com\/archives\/214\">https:\/\/www.newtopchem.com\/archives\/214<\/a><\/p>\n","protected":false,"gt_translate_keys":[{"key":"rendered","format":"html"}]},"excerpt":{"rendered":"<p>Structural formula Business number 0173 Molecular formu&#8230;<\/p>\n","protected":false,"gt_translate_keys":[{"key":"rendered","format":"html"}]},"author":1,"featured_media":48879,"comment_status":"closed","ping_status":"closed","sticky":false,"template":"","format":"standard","meta":[],"categories":[6],"tags":[15334],"gt_translate_keys":[{"key":"link","format":"url"}],"_links":{"self":[{"href":"http:\/\/www.newtopchem.com\/wp-json\/wp\/v2\/posts\/48880"}],"collection":[{"href":"http:\/\/www.newtopchem.com\/wp-json\/wp\/v2\/posts"}],"about":[{"href":"http:\/\/www.newtopchem.com\/wp-json\/wp\/v2\/types\/post"}],"author":[{"embeddable":true,"href":"http:\/\/www.newtopchem.com\/wp-json\/wp\/v2\/users\/1"}],"replies":[{"embeddable":true,"href":"http:\/\/www.newtopchem.com\/wp-json\/wp\/v2\/comments?post=48880"}],"version-history":[{"count":0,"href":"http:\/\/www.newtopchem.com\/wp-json\/wp\/v2\/posts\/48880\/revisions"}],"wp:featuredmedia":[{"embeddable":true,"href":"http:\/\/www.newtopchem.com\/wp-json\/wp\/v2\/media\/48879"}],"wp:attachment":[{"href":"http:\/\/www.newtopchem.com\/wp-json\/wp\/v2\/media?parent=48880"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"http:\/\/www.newtopchem.com\/wp-json\/wp\/v2\/categories?post=48880"},{"taxonomy":"post_tag","embeddable":true,"href":"http:\/\/www.newtopchem.com\/wp-json\/wp\/v2\/tags?post=48880"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}