145013-05-4

Basic information

• Product Name: N,N'-BIS-TERT-BUTOXYCARBONYLTHIOUREA
• Synonyms: N,Nμ-Di-Boc-thiourea;Diboc-thiourea;N,N'-bis(1,1-diMethylethoxycarbonyl)thiourea;N,N`-Di-Boc-thiourea,97%;1,3-Bis(tert-butoxycarbonyl)thiourea;N,N'-Di-Boc-thiourea 97%;N,N'-Di-(tert-Butoxycarbonyl)thiourea≥ 98% (HPLC);Bis-Boc-thiourea Novabiochem
• CAS NO: 145013-05-4
• Molecular Formula: C₁₁H₂₀N₂O₄S
• Molecular Weight: 276.35
• EINECS: 215-888-7
• Product Categories: Building Blocks;Chemical Synthesis;Organic Building Blocks;Sulfur Compounds;Thioureas
• Mol File: 145013-05-4.mol
• Article Data: 19

Chemical Properties

• Melting Point: 131-135 °C(lit.)
• Appearance: /
• Density: 1.152
• Storage Temp.: Store at 0-5°C
• PKA: 5.55±0.70(Predicted)
• CAS DataBase Reference: N,N'-BIS-TERT-BUTOXYCARBONYLTHIOUREA(CAS DataBase Reference)
• NIST Chemistry Reference: N,N'-BIS-TERT-BUTOXYCARBONYLTHIOUREA(145013-05-4)
• EPA Substance Registry System: N,N'-BIS-TERT-BUTOXYCARBONYLTHIOUREA(145013-05-4)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• Hazardous Substances Data: 145013-05-4(Hazardous Substances Data)

Usage

Chemical Properties

White to off-white solid

Uses

Different sources of media describe the Uses of 145013-05-4 differently. You can refer to the following data:
1. N,N′-Di-Boc-thiourea (N,N′-di-Boc-substituted thiourea), also known as di-Boc-thiourea is a thioacylating agent for preparing thiocarbonyl compounds. N,N′-Di-Boc-thiourea (di-Boc protected thiourea) may be used as a guanylating agent for the synthesis of guanidines, via guanylation of amines in the presence of Mukaiyama′s reagent as a promoter.
2. N,N''-Di(tert-butoxycarbonyl)thiourea is used in the preparation of bis-imidazoline diphenyl derivatives as α1-adrenoceptor antagonists.

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 17356-08-0 thiourea 
• 34619-03-9 tert-butyldicarbonate 

Downstream Products

• 145013-08-7 C₂₆H₄₀N₄O₈ 
• 145013-07-6 C₂₅H₃₈N₄O₈ 
• 152120-56-4 N,N′-bis(tert-butoxycarbonyl)-N′′-phenylguanidine 
• 145013-06-5 N,N′-bis(tert-butoxycarbonyl)-N′′-benzylguanidine 
• 199536-01-1 methyl 3-amino-5-cyanobenzoate 
• 183431-00-7 methyl 3-({[(tert-butoxycarbonyl)amino][(tert-butoxycarbonyl)imino]methyl}amino)-5-[(N-hydroxyimino)methyl]benzoate 
• 199535-69-8 methyl 3-({[(tert-butoxycarbonyl)amino][(tert-butoxycarbonyl)imino]methyl}amino)-4-[(methylsulfoxy)methyl]benzoate 
• 199535-84-7 methyl 3-({[(tert-butoxycarbonyl)amino][(tert-butoxycarbonyl)imino]methyl}amino)-4-[(methylsulfonyl)methyl]benzoate 
• 199536-07-7 methyl 3-({[(tert-butoxycarbonyl)amino][(tert-butoxycarbonyl)imino]methyl}amino)-5-(hydroxymethyl)benzoate 
• 199535-96-1 methyl 3-amino-5-({[(tert-butoxycarbonyl)amino][(tert-butoxycarbonyl)imino]methyl}amino)benzoate 
• 199535-55-2 methyl 3-({[(tert-butoxycarbonyl)amino][(tert-butoxycarbonyl)imino]methyl}amino)-4-(2-hydroxyethyl)benzoate 
• 714275-86-2 C₂₃H₂₉N₃O₅ 
• 628733-25-5 (+/-)-N-[1-(3-benzyl-7-chloro-4-oxo-3,4-dihydro-pyrrolo[2,1-f][1,2,4]triazin-2-yl)-propy]-N-(3-guanidino-propyl)-4-methyl-benzamide, trifluoroacetic acid salt 

Relevant articles and documents

Preparation of N,N'-bis-tert-butoxycarbonylthiourea

The preparation of N,N'-bis-tert-butoxycarbonylthiourea from thiourea and di-tert-butyl dicarbonate in tetrahydrofuran is described.

Di-aryl guanidinium derivatives: Towards improved α2-Adrenergic affinity and antagonist activity

Compounds with excellent receptor engagement displaying α2-AR antagonist activity are useful not only for therapeutic purposes (e.g. antidepressants), but also to help in the crystallization of this particular GPCR. Therefore, based on our broad experience in the topic, we have prepared eighteen di-aryl (phenyl and/or pyridin-2-yl) mono- or di-substituted guanidines and 2-aminoimidazolines. The in vitro α2-AR binding affinity experiments in human brain tissue showed the advantage of a 2-aminoimidazolinium cation, a di-arylmethylene core, a conformationally locked pyridin-2-yl-guanidine and a di-substituted guanidinium to achieve good α2-AR engagement. After different in vitro [35S]GTPγS binding experiments in human prefrontal cortex tissue, it was possible to identify that compounds 7a, 7b and 7c were α2-AR partial agonist, whereas 8h was a potent α2-AR antagonist. Docking and MD studies with a model of α2A-AR and two crystal structures suggest that antagonism is achieved by compounds carrying a di-substituted guanidine which substituent occupy a pocket adjacent to TM5 without engaging S2005.42 or S2045.46, and a mono-substituted cationic group, which favorably interacts with E942.65.

α-Amino Acid-Isosteric α-Amino Tetrazoles

The synthesis of all 20 common natural proteinogenic and 4 otherα-amino acid-isosteric α-amino tetrazoles has been accomplished, whereby the carboxyl group is replaced by the isosteric 5-tetrazolyl group. The short process involves the use of the key Ugi tetrazole reaction followed by deprotection chemistries. The tetrazole group is bioisosteric to the carboxylic acid and is widely used in medicinal chemistry and drug design. Surprisingly, several of the common α-amino acid-isosteric α-amino tetrazoles are unknown up to now. Therefore a rapid synthetic access to this compound class and non-natural derivatives is of high interest to advance the field.

INHIBITORS OF BETA-SECRETASE

The present invention relates to spirocyclic acylguanidines and their use as inhibitors of the β-secretase enzyme (BACE1) activity, pharmaceutical compositions containing the same, and methods of using the same as therapeutic agents in the treatment of neurodegenerative disorders, disorders characterized by cognitive decline, cognitive impairment, dementia and diseases characterized by production of β-amyloid aggregates.