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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/REAXYS Number:
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

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

10 - Combustible liquids

wgk_germany

WGK 3

flash_point_f

228.2 °F - closed cup

flash_point_c

109 °C - closed cup

ppe

Eyeshields, Gloves, type ABEK (EN14387) respirator filter

Certificates of Analysis (COA)

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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)
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)
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
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
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