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145947

Sigma-Aldrich

Tetrachlorocyclopropene

98%

Synonym(s):

1,2,3,3-Tetrachlorocyclopropene, Perchlorocyclopropene, Tetrachlorocyclopropenone, Tetrachlorocycloproprene

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About This Item

Empirical Formula (Hill Notation):
C3Cl4
CAS Number:
6262-42-6
Molecular Weight:
177.84
Beilstein:
1099206
EC Number:
228-418-0
MDL number:
MFCD00001267
UNSPSC Code:
12352100
PubChem Substance ID:
24848753
NACRES:
NA.22

Assay

98%

form

liquid

refractive index

n20/D 1.507 (lit.)

bp

125-130 °C (lit.)

density

1.45 g/mL at 25 °C (lit.)

storage temp.

2-8°C

SMILES string

ClC1=C(Cl)C1(Cl)Cl

InChI

1S/C3Cl4/c4-1-2(5)3(1,6)7

InChI key

BLZOHTXDDOAASQ-UHFFFAOYSA-N

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General description

Tetrachlorocyclopropene undergoes electrochemical reductive tert-butyldimethylsilylation to yield 1,2,3-tris(tert-butyldimethylsilyl)cyclopropene. It undergoes alkylation reaction with ferrocene in dichloromethane and AlCl3 to yield 2,3-diferrocenylcyclopropenone.

Application

Tetrachlorocyclopropene was used to prepare starting reagent for synthesis of 3,3-diethyl-and 3,3-dibenzyl-1,2-diferrocenylcyclopropenes.

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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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Elena I Klimova et al.
Organic & biomolecular chemistry, 1(24), 4458-4464 (2004-01-20)
Reactions of 2,3-diferrocenylcyclopropenone 1 with ethyl- and benzylmagnesium chlorides afford 3,3-diethyl-and 3,3-dibenzyl- 1,2-diferrocenylcyclopropenes 2 and 3, respectively, and products of nucleophilic opening of the three-membered ring resulting from the addition of RMgCl to the carbonyl group, viz., saturated ketones(4,5-diferrocenylheptan-3-ones 4a,b
H A Buchholz et al.
Proceedings of the National Academy of Sciences of the United States of America, 96(18), 10003-10005 (1999-09-01)
Electrochemical reductive tert-butyldimethylsilylation of tetrachlorocyclopropene to 1,2,3-tris(tert-butyldimethylsilyl)cyclopropene, a potential strained precursor for Diels-Alder and related cycloaddition reactions, is described. By hydride abstraction with nitrosonium tetrafluoroborate, 1,2,3-tris(tert-butyldimethylsilyl)cyclopropene is ionized quantitatively to Hückeloid 2pi aromatic tris(tert-butyldimethylsilyl)cyclopropenium tetrafluoroborate.
Jesús García-Valdés et al.
Journal of inorganic biochemistry, 197, 110689-110689 (2019-05-18)
Bis-cations with two 2,3-diferrocenylcyclopropenium fragments 3a-d, and the cis-2-(1,2-diferrocenylvinyl)-2-imidazolinium tetrafluoroborates 4a, d or the cis-2-(1,2-diferrocenylvinyl)-3,4,5,6-tetrahydropyrimidin-2-ium tetrafluoroborates 4b, c were obtained by interactions of 2,3-diferrocenyl-1-ethoxycyclopropenium tetrafluoroborate 1 with bis-1,4-N,N-(2a, d) or bis-1,5-N,N-(2b, c) nucleophiles. The reactions of 3a-d with sodium azide

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