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458910

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

Quality Level

100

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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

FSL

Group 4: Flammable liquids
Type 3 petroleums
Hazardous rank III
Water insoluble liquid

JAN Code

458910-25ML:
458910-VAR:
458910-BULK:
458910-5ML:

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Certificates of Analysis (COA)

Lot/Batch Number
MKCP9774
MKCM6255
MKCF6498
MKCC4515
MKBX6597V

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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
Binoy Maiti et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 23(60), 15156-15165 (2017-08-30)
Poly[2-(methacryloyloxy)ethyl oleate-co-pentafluorophenyl methacrylate] [P(MAEO-co-PFPMA)] random copolymers with oleate and pentafluorophenyl side-chain pendants were synthesized. These copolymers were utilized as dual-reactive polymeric scaffolds in a range of post-polymerization modification strategies involving thiol-ene and para-fluoro-thiol substitution, amidation, trans-esterification, and epoxidation followed by
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
Anne Müller et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 21(39), 13723-13731 (2015-08-08)
Azobenzene linker molecules can be utilized to control peptide/protein function when they are ligated to appropriately spaced amino acid side chains of the peptide. This is because the photochemical E/Z isomerization of the azobenzene N=N double bond allows to switch
Josiane P Lafleur et al.
Lab on a chip, 15(10), 2162-2172 (2015-04-09)
A novel, rapid and simple method for the preparation of emulsion-templated monoliths in microfluidic channels based on thiol-ene chemistry is presented. The method allows monolith synthesis and anchoring inside thiol-ene microchannels in a single photoinitiated step. Characterization by scanning electron

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