291536
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:
Molecular Weight:
380.82
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
MDL number:
Beilstein/REAXYS Number:
2141527
Assay:
≥97%
Form:
solid
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+
SMILES string
ClC(Cl)(Cl)COC(=O)\N=N\C(=O)OCC(Cl)(Cl)Cl
InChI key
LIEOEYTUTSDYKB-BUHFOSPRSA-N
assay
≥97%
form
solid
storage temp.
2-8°C
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
signalword
Warning
hcodes
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
target_organs
Respiratory system
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
dust mask type N95 (US), Eyeshields, Gloves
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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)
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
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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