2-(Boc-amino)ethanethiol

Base Information

• Chemical Name: 2-(Boc-amino)ethanethiol
• CAS No.: 67385-09-5
• Molecular Formula: C7H15 N O2 S
• Molecular Weight: 177.268
• Hs Code.: 2930909090
• European Community (EC) Number: 628-681-5
• DSSTox Substance ID: DTXSID50986668
• Nikkaji Number: J1.347.856B
• Wikidata: Q82974670
• Mol file: 67385-09-5.mol

Synonyms:N-(tert-butoxycarbonyl)-2-aminoethanethiol;N-Boc-AET

Chemical Property of 2-(Boc-amino)ethanethiol

Chemical Property:

• Vapor Pressure: 0.0106mmHg at 25°C
• Refractive Index: n20/D 1.474(lit.)
• Boiling Point: 68 °C0.3 mm Hg(lit.)
• PKA: 9.95±0.10(Predicted)
• Flash Point: >230 °F
• PSA: 77.13000
• Density: 1.049 g/mL at 20 °C(lit.)
• LogP: 1.83180
• Storage Temp.: Hygroscopic, Refrigerator, under inert atmosphere
• Solubility.: Chloroform (Sparingly), Ethyl Acetate (Slightly)
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 177.08234989
• Heavy Atom Count: 11
• Complexity: 131

Purity/Quality:

98%,99%, ^*data from raw suppliers

2-(Boc-amino)ethanthiol(>90%) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NCCS
• Uses: 2-(Boc-amino)ethanthiol is used in the synthesis of several organic compounds including a novel, anisamide-targeted cyclodextrin nanoformulation for the delivery of siRNA to prostate cancer cells which is a potential therapeutic option. Also used in the synthesis of bifunctional azobenzene glycoconjugates for cysteine-based photosensitive cross-linking with bioactive peptides.

Technology Process of 2-(Boc-amino)ethanethiol

There total 11 articles about 2-(Boc-amino)ethanethiol 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: 98.0%

di-tert-butyl dicarbonate (24424-99-5) + Cysteamine (60-23-1) → 2-[(tert-butoxycarbonyl)amino]-1-ethanethiol (67385-09-5)

Guidance literature:

In tetrahydrofuran; water; at 20 ℃; for 4h; Inert atmosphere;

DOI:10.1002/anie.201505076

Reference yield: 96.0%

di-tert-butyl(disulfanediylbis(ethane-2,1-diyl))dicarbamate (67385-10-8) → 2-[(tert-butoxycarbonyl)amino]-1-ethanethiol (67385-09-5)

Guidance literature:

With hydrogen; rhodium hydrido (PEt₃)3 complex; In toluene; for 0.5h; Heating;

DOI:10.1016/j.tetlet.2005.06.169

Reference yield: 95.0%

di-tert-butyl dicarbonate (24424-99-5) + 2-mercaptoethylamine hydrochloride (156-57-0) → 2-[(tert-butoxycarbonyl)amino]-1-ethanethiol (67385-09-5)

Guidance literature:

2-mercaptoethylamine hydrochloride; With sodium hydride; In tetrahydrofuran; at 0 - 20 ℃;

di-tert-butyl dicarbonate; In tetrahydrofuran; at 0 - 20 ℃;

DOI:10.1081/SCC-120004152

upstream raw materials:

di-tert-butyl dicarbonate

2-mercaptoethylamine hydrochloride

2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile

Cysteamine

Downstream raw materials:

Fmoc-Tyr-D-Lys-GlyψPhe-Leu-OH

cyclo(GlyψPhe)3

tert-butyl (2-(methylthio)ethyl)carbamate

(2-{3-[3-((R)-1-Methyl-2-oxo-5-phenyl-2,3-dihydro-1H-benzo[e][1,4]diazepin-3-yl)-ureido]-benzylsulfanyl}-ethyl)-carbamic acid tert-butyl ester

Refernces

• 1、 Ishikawa, Fumihiro,Haushalter, Robert W.,Burkart, Michael D.. "Dehydratase-specific probes for fatty acid and polyketide synthases". . p. 769 - 772. Retrieved 2012.
• 2、 Wang, Yanyan,Fan, Jingwei,Darensbourg, Donald J.. "Construction of Versatile and Functional Nanostructures Derived from CO2-based Polycarbonates". . p. 10206 - 10210. Retrieved 2015.
• 3、 -. "Preparation method of benzothiazepine oxide, product prepared by preparation method and application of product". Paragraph 0058-0062; 0093; 0100. . Retrieved 2020/08/30.
• 4、 -. "A compound and use thereof". Paragraph 0048; 0049; 0050. . Retrieved 2017/02/02.