2-Methyl-2-thiopseudourea sulfate

Base Information

• Chemical Name: 2-Methyl-2-thiopseudourea sulfate
• CAS No.: 867-44-7
• Deprecated CAS: 147895-43-0
• Molecular Formula: (C2H6N2S)2^.H2SO4
• Molecular Weight: 278.378
• Hs Code.: 29309070
• European Community (EC) Number: 218-860-2,238-544-8
• NSC Number: 227845,516
• DSSTox Substance ID: DTXSID50932549
• ChEMBL ID: CHEMBL1256354
• Mol file: 867-44-7.mol

Synonyms:2-Methyl-2-thiopseudourea sulfate;14527-26-5;2260-00-6;Methyl carbamimidothioate sulfate;S-Methylthiourea sulfate;Carbamimidothioic acid, methyl ester, sulfate;Methyl thiopseudourea sulfate;S-Methylthiopseudourea sulfate;S-Methylisothioureasulfate;USAF EK-1231;2-Methyl-2-thiopeudourea sulfate;Bis(S-methylthiouronium) sulphate;S-Methylthiuronium sulfate;S-Methylthiouronium sulfate;Carbamimidothioic acid, methyl ester, sulfate (1:1);S-Methylisothiuronium sulfate;methyl carbamimidothioate;sulfuric acid;S-Methylpseudothiourea sulfate;2-Methylisothiouronium sulfate;S-Methylisothiourea sulfate (1:1);EINECS 218-860-2;EINECS 238-544-8;2-Methyl-2-thiopseudourea monosulfate;NSC 227845;2-Methylisothiouronium hydrogen sulphate;2-METHYL-2-THIOPSEUDOUREA,SULFATE;C2H6N2S.H2O4S;CHEMBL1256354;Methylisothiourea Sulfate;Pseudourea, 2-methyl-2-thio-, sulfate (1:1);Carbamimidothioic acid, methyl ester, sulfate (1:?);S-methylisothiourea hydrogen sulfate;s-methylisothiourea-sulfate;2-methylisothiourea sulfate;2-methylisothiourea sulphate;C2H6N2S.xH2O4S;Pseudourea, hydrogen sulfate;S-methyl-isothiourea sulfate;2-methyl-isothiourea sulfate;SCHEMBL18206;Pseudourea, sulfate (2:1);S-methyl-isothiourea sulphate;2-methylthiopseudourea sulfate;S-methyl-iso-thiourea sulphate;AMY304;C2H8N2O4S2;NSC516;Bis(s-methylthiouronium)sulphate;DTXSID50932549;s-methyl-2-thiopseudourea sulfate;2-methylisothiourea;s-methyl-2-thiopseudourea sulphate;2-methyl 2-thiopseudourea sulphate;2-methyl-2-thiopseudourea sulphate;S-methylisothiopseudouronium sulfate;2 -methyl-2-thiopseudourea sulfate;2-methyl-2-thio-pseudourea sulfate;BDBM50194240;NSC227845;C2-H6-N2-S.H2-O4-S;AKOS005068053;C2-H6-N2-S.x-H2-O4-S;2-Methyl-2-thiopseudourea, hemisulfate;Carbamimidothioic acid, sulfate (1:1);Carbamimidothioic acid, sulfate (2:1);NSC-227845;AS-80386;LS-126193;LS-126195;S-methylisothiopseudouronium sulfate (1:1);CS-0134406;FT-0612930;FT-0612931;(methylsulfanyl)methanimidamide;E70432;Sulfuric acid--methyl carbamimidothioate (1/1);A816279;A841823;carbamimidothioic acid methyl ester;Carbamimidothioic acid, methyl ester, sulfate (1:1) (9CI)

Chemical Property of 2-Methyl-2-thiopseudourea sulfate

Chemical Property:

• Appearance/Colour: white crystalline powder
• Melting Point: 240-241 °C (dec.)(lit.)
• Boiling Point: 138.8 °C at 760 mmHg
• PKA: pK1:9.83(＋1) (25°C)
• Flash Point: 37.7 °C
• PSA: 158.15000
• Density: 1.28 g /cm³
• LogP: 1.47090
• Storage Temp.: Store at RT
• Sensitive.: Hygroscopic
• Solubility.: H2O: 0.1 g/mL, clear, colorless
• Water Solubility.: 260 g/L (20 ºC)
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 1
• Exact Mass: 187.99254909
• Heavy Atom Count: 10
• Complexity: 124

Purity/Quality:

99% ^*data from raw suppliers

S-Methyl-isothiouroniumHemisulfate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CSC(=N)N.OS(=O)(=O)O
• Description: SMIT is a potent non-selective inhibitor of NOS isoforms in vitro but may lack good in vivo efficacy due to poor cellular penetration. The Ki values are 120, 200, and 160 nM using purified human iNOS, eNOS, and nNOS, respectively.
• Uses: Intermediate of 4-Hydroxydebrisoquine. S-Methyl-isothiouronium Hemisulfate is also a reagent used in the synthesis of strobilurin-pyrimidine derivatives for their anti-proliferative activity.

Technology Process of 2-Methyl-2-thiopseudourea sulfate

There total 4 articles about 2-Methyl-2-thiopseudourea sulfate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 80.0%

thiourea (17356-08-0) + dimethyl sulfate (77-78-1) → S-Methylisothiourea sulfate (867-44-7,147895-43-0)

Guidance literature:

In water; at 25 - 80 ℃; for 7h; Heating / reflux;

Reference yield: 25.9%

thiourea (17356-08-0) + dimethyl sulfate (77-78-1) → 2-methylisothiourea sulphate (14527-26-5,867-44-7,147895-43-0)

Guidance literature:

In water; at 80 ℃; for 6.5h; Reflux;

DOI:10.1021/acs.jmedchem.6b01576

Reference yield:

methanol (67-56-1) + thiouronium hydrogensulfate (37622-16-5) → 2-methylisothiourea sulphate (14527-26-5,867-44-7,147895-43-0)

Guidance literature:

DOI:10.1039/CT9171100650

upstream raw materials:

methanol

thiouronium hydrogensulfate

thiourea

dimethyl sulfate

Downstream raw materials:

IPRO-2

guanidinosuccinic acid

3-(2-Carboxy-2-guanidino-ethyldisulfanyl)-2-guanidino-propionic acid

C₁₀H₁₆N₄O₂

Refernces

• 1、 Huang, Ying,Zhang, Jeff,Yu, Zhengtian,Zhang, Hailong,Wang, Youzhen,Lingel, Andreas,Qi, Wei,Gu, Justin,Zhao, Kehao,Shultz, Michael D.,Wang, Long,Fu, Xingnian,Sun, Yongfeng,Zhang, Qiong,Jiang, Xiangqing,Zhang, Jiangwei,Zhang, Chunye,Li, Ling,Zeng, Jue,Feng, Lijian,Zhang, Chao,Liu, Yueqin,Zhang, Man,Zhang, Lijun,Zhao, Mengxi,Gao, Zhenting,Liu, Xianghui,Fang, Douglas,Guo, Haibing,Mi, Yuan,Gabriel, Tobias,Dillon, Michael P.,Atadja, Peter,Oyang, Counde. "Discovery of First-in-Class, Potent, and Orally Bioavailable Embryonic Ectoderm Development (EED) Inhibitor with Robust Anticancer Efficacy". supporting information. p. 2215 - 2226. Retrieved 2017/04/03.
• 2、 Qiu, Kui,Wang, Rennan. "Tert -Butyl Hypochlorite Mediated Oxidative Chlorination of S -Alkylisothiourea Salts: Synthesis of Sulfonyl Chlorides". . p. 3186 - 3190. Retrieved 2015/10/19.