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749648

Sigma-Aldrich

2-[2-(Boc-amino)ethoxy]ethanol

97%

Synonym(s):

2-(2-tert-Butoxycarbonylaminoethoxy)ethanol, N-[2-(2-Hydroxyethoxy)ethyl]carbamic acid tert-butyl ester, tert-Butyl[2-(2-hydroxyethoxy)ethyl]carbamate, [2-(2-Hydroxyethoxy)ethyl]carbamic acid 1,1-dimethylethyl ester

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About This Item

Empirical Formula (Hill Notation):
C9H19NO4
CAS Number:
139115-91-6
Molecular Weight:
205.25
MDL number:
MFCD04038542
UNSPSC Code:
12352100
PubChem Substance ID:
329766008
NACRES:
NA.22

Assay

97%

form

liquid

refractive index

n20/D 1.454

density

1.061 g/mL at 25 °C

functional group

amine
ether
hydroxyl

SMILES string

CC(C)(C)OC(=O)NCCOCCO

InChI

1S/C9H19NO4/c1-9(2,3)14-8(12)10-4-6-13-7-5-11/h11H,4-7H2,1-3H3,(H,10,12)

InChI key

KSFVNEXYCULLEJ-UHFFFAOYSA-N

Related Categories

Application

2-[2-(Boc-amino)ethoxy]ethanol is N-terminal protected 2-(2-aminoethoxy)ethanol. It is generally used as a molecular spacer/linker. Some of such applications are:
  • Synthesis of biotinylated HaloLigands to prepare quantum dot adducts for HaloTag protein-mediated specific labeling of live cells.
  • It is one of the key precursors for the total synthesis of tyroscherin and photo-activatable tyroscherin-based affinity reagent used for identification of tyroscherin binding proteins.
  • It can be used to link HaloTag enzyme with fluorescent zinc indicator, ZIMIR to monitor the dynamics of regulated secretion of zinc in real time.
  • It can also be used to synthesize amphiphiles for DNA and siRNA delivery.

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H301,H315,H319

Hazard Classifications

Acute Tox. 3 Oral - Eye Irrit. 2 - Skin Irrit. 2

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
MKCV3627
MKCT5118
MKCL8243
MKCC4845
MKBZ3466V

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Total synthesis and biological evaluation of tyroscherin.
Tae H S, et al.
Organic Letters, 12(19), 4308-4311 (2010)
Genetic targeting of a small fluorescent zinc indicator to cell surface for monitoring zinc secretion.
Li D, et al.
ACS Chemical Biology, 10(4), 1054-1063 (2015)
HaloTag protein-mediated specific labeling of living cells with quantum dots.
So M K, et al.
Biochemical and Biophysical Research Communications, 374(3), 419-423 (2008)
The effect of charge-reversal amphiphile spacer composition on DNA and siRNA delivery.
Zhang X X, et al.
Bioconjugate Chemistry, 21(5), 988-993 (2010)

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