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Sigma-Aldrich

2-(Boc-amino)ethanethiol

97%

Synonym(s):

tert-Butyl N-(2-mercaptoethyl)carbamate

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About This Item

Linear Formula:
HSCH2CH2NHCO2C(CH3)3
CAS Number:
67385-09-5
Molecular Weight:
177.26
Beilstein:
2243173
MDL number:
MFCD00274335
UNSPSC Code:
12352105
PubChem Substance ID:
24869348
NACRES:
NA.22

Assay

97%

reaction suitability

reagent type: cross-linking reagent

refractive index

n20/D 1.474 (lit.)

bp

68 °C/0.3 mmHg (lit.)

density

1.049 g/mL at 20 °C (lit.)

functional group

Boc
amine
thiol

SMILES string

SCCNC(OC(C)(C)C)=O

InChI

1S/C7H15NO2S/c1-7(2,3)10-6(9)8-4-5-11/h11H,4-5H2,1-3H3,(H,8,9)

InChI key

GSJJCZSHYJNRPN-UHFFFAOYSA-N

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General description

2-(Boc-amino)ethanethiol also known as tert-butyl N-(2-mercaptoethyl)carbamate, is a cross linking reagent which can be utilized in various organic syntheses.

Application

2-(Boc-amino)ethanethiol is used to introduce the amine functional group for the surface functionalization of cross-linked polymer films by thiol-ene click chemistry reactions. Additionally, it participates in the thiol-ene reaction to achieve amine functionalization of polyglobalide(PGI).

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

228.2 °F - closed cup

Flash Point(C)

109 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Terpolymerization of propylene oxide and vinyl oxides with CO 2: copolymer cross-linking and surface modification via thiol-ene click chemistry.
DJ Darensbourg, et al.
Polym. Chem., 1768-1776 (2015)
Poly (amino acid)-grafted polymacrolactones. Synthesis, self-assembling and ionic coupling properties
E Tinajero-Diaz, et al.
Reactive and Functional Polymers, 143, 104316-104316 (2019)
Ernesto Tinajero-Díaz et al.
Polymers, 12(4) (2020-04-30)
The enzymatic ring-opening copolymerization (eROP) of globalide (Gl) and pentadecalactone (PDL) was performed in solution from mixtures of the two macrolactones at ratios covering the whole range of comonomeric compositions. The resulting P(Glx-r-PDLy) random copolyesters were aminofunctionalized by thiol-ene reaction
T M Winger et al.
Bioconjugate chemistry, 6(3), 323-326 (1995-05-01)
The derivatization of poly(p-(chloromethyl)styrene-co-divinylbenzene) (Merrifield resin) with N-(tert-butoxycarbonyl)-2-aminoethanethiol is presented as a convenient route for the generation of thiol terminated peptides using a solid phase methodology. Maximum resin substitution reached 92% (773 mumol/g) after 24 h. However, at 30 min
Louise Stjern et al.
International journal of pharmaceutics, 531(2), 595-605 (2017-05-31)
Cyclodextrins (CDs) and mesoporous silica particles (MSPs) have been combined as composite carriers for controlled antibiotic release. CDs were employed as "gatekeeper" agents and grafted onto MSPs to retain drug molecules inside the MSP carrier. A variety of CDs (unfunctionalized
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