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Merck
CN

291536

Sigma-Aldrich

Bis(2,2,2-trichloroethyl) azodicarboxylate

≥97%

Synonym(s):

Azodicarboxylic acid bis(2,2,2-trichloroethyl ester)

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About This Item

Linear Formula:
CCl3CH2OCON=NCOOCH2CCl3
CAS Number:
38857-88-4
Molecular Weight:
380.82
Beilstein:
2141527
MDL number:
MFCD00010607
UNSPSC Code:
12352100
PubChem Substance ID:
24857539
NACRES:
NA.22

Key Documents

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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

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

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

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Certificates of Analysis (COA)

Lot/Batch Number
0000076294
0000072506
0000062995
0000049181
0000041953

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Michael C Hillier et al.
The Journal of organic chemistry, 70(21), 8385-8394 (2005-10-08)
A general asymmetric synthesis of substituted cycloalkyl[b]indoles has been accomplished. The key features of this approach are (1) the utilization of a Japp-Klingemann condensation/Fischer cyclization to prepare cycloalkyl[b]indolones, (2) the asymmetric borane reduction of these heterocyclic ketones with (S)-OAB to
A Toepfer et al.
Carbohydrate research, 247, 159-164 (1993-09-02)
In a thermal inverse-type hetero-Diels-Alder reaction of O-silyl-protected lactal 1 and bis(2,2,2-trichloroethyl) azodicarboxylate (2), the dihydrooxadiazine derivative 3 was obtained in a very high yield; transesterification with benzyl alcohol furnished the corresponding derivative 4. Treatment of 3 with methanol in
Organic Syntheses, 61, 17-17 (1983)
Pompiliu S Aburel et al.
Organic & biomolecular chemistry, 3(12), 2344-2349 (2005-07-13)
Lewis acids such as Cu(OTf)(2), Zn(OTf)(2), Yb(OTf)(3) and Nd(OTf)(3) catalyze the aza-ene reaction of alkenes with azodicarboxylates, giving the allylic amination adducts. The use of bis(2,2,2-trichloroethyl)azodicarboxylate as the amination reagent and Cu(OTf)(2) and Yb(OTf)(3) as the catalysts gave the aza-ene
Para-directed amination of electron-rich arenes with bis (2, 2, 2-trichloroethyl) azodicarboxylate.
Leblanc Y and Boudreault N.
The Journal of Organic Chemistry, 60(13), 4268-4271 (1995)

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