MilliporeSigma
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291536

Sigma-Aldrich

Bis(2,2,2-trichloroethyl) azodicarboxylate

≥97%

Synonym(s):
Azodicarboxylic acid bis(2,2,2-trichloroethyl ester)
Linear Formula:
CCl3CH2OCON=NCOOCH2CCl3
CAS Number:
Molecular Weight:
380.82
Beilstein:
2141527
MDL number:
PubChem Substance ID:
NACRES:
NA.22

assay

≥97%

form

solid

mp

109-111 °C (lit.)

storage temp.

2-8°C

SMILES string

ClC(Cl)(Cl)COC(=O)\N=N\C(=O)OCC(Cl)(Cl)Cl

InChI

1S/C6H4Cl6N2O4/c7-5(8,9)1-17-3(15)13-14-4(16)18-2-6(10,11)12/h1-2H2/b14-13+

InChI key

LIEOEYTUTSDYKB-BUHFOSPRSA-N

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General description

Thermal inverse-type hetero-Diels-Alder reaction of O-silyl-protected lactal and bis(2,2,2-trichloroethyl) azodicarboxylate has been reported.

Application

Bis(2,2,2-trichloroethyl) azodicarboxylate has been used:
  • in the asymmetric synthesis of substituted cycloalkyl[b]indoles
  • as amination reagent during the aza-ene reaction of different alkenes to yield the corresponding allyl amines
  • in para-directed amination of C2-alkyl substituted anisole
  • in the synthesis of acid- and base-sensitive azo compounds and in Diels-Alder cycloadditions

Packaging

5 g in glass bottle

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Precautionary Statements

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificate of Analysis

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Certificate of Origin

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