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Sigma-Aldrich

tert-Butyl 2,2,2-trichloroacetimidate

96%

Synonym(s):

TBTA

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About This Item

Linear Formula:
CCl3C(=NH)OC(CH3)3
CAS Number:
98946-18-0
Molecular Weight:
218.51
Beilstein:
1770049
MDL number:
MFCD00077410
UNSPSC Code:
12352100
PubChem Substance ID:
24862454
NACRES:
NA.22

Assay

96%

refractive index

n20/D 1.456 (lit.)

bp

65 °C/11 mmHg (lit.)

mp

21 °C (lit.)

density

1.221 g/mL at 25 °C (lit.)

storage temp.

2-8°C

SMILES string

CC(C)(C)OC(=N)C(Cl)(Cl)Cl

InChI

1S/C6H10Cl3NO/c1-5(2,3)11-4(10)6(7,8)9/h10H,1-3H3

InChI key

CQXDYHPBXDZWBA-UHFFFAOYSA-N

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Application

tert-Butyl 2,2,2-trichloroacetimidate may be used in the synthesis of N-α-Fmoc-phospho(1-nitrophenylethyl-2-cyanoethyl)-L-serine, caged building block. It may be used in the conversion of alcohols and carboxylic acids to their respective ethers and esters.

Pictograms

FlameExclamation mark
GHS02,GHS07

Signal Word

Warning

Hazard Statements

H226,H302,H315,H319,H335

Hazard Classifications

Acute Tox. 4 Oral - Eye Irrit. 2 - Flam. Liq. 3 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

131.0 °F - closed cup

Flash Point(C)

55 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Tetrahedron Letters, 29, 2483-2483 (1988)
Journal of the Chemical Society. Perkin Transactions 1, 2247-2247 (1985)
Deborah M Rothman et al.
The Journal of organic chemistry, 68(17), 6795-6798 (2003-08-16)
Three 1-(2-nitrophenyl)ethyl-caged phospho-amino acids have been synthesized for use in standard N(alpha)-fluorenylmethoxycarbonyl-based solid-phase peptide synthesis (SPPS). The most common naturally occurring phospho-amino acids, serine, threonine, and tyrosine, were prepared as protected caged building blocks by modification with a unique phosphitylating
Maiyun Yang et al.
Nature communications, 5, 4981-4981 (2014-09-23)
Bioorthogonal reactions, especially the Cu(I)-catalysed azide-alkyne cycloaddition, have revolutionized our ability to label and manipulate biomolecules under living conditions. The cytotoxicity of Cu(I) ions, however, has hindered the application of this reaction in the internal space of living cells. By
Brett J Roberts et al.
Journal of cell science, 127(Pt 17), 3782-3793 (2014-07-09)
Desmosomes are prominent adhesive junctions found in various epithelial tissues. The cytoplasmic domains of desmosomal cadherins interact with a host of desmosomal plaque proteins, including plakophilins, plakoglobin and desmoplakin, which, in turn, recruit the intermediate filament cytoskeleton to sites of

Articles

Trichloroacetimidate Reagents

Trichloroacetimidates are also commonly employed as alcohol alkylation reagents, particularly when existing functionality is not acid sensitive.

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