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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/REAXYS Number:
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.)

functional group

chloro

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

10 - Combustible liquids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type ABEK (EN14387) respirator filter

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Certificates of Analysis (COA)

Lot/Batch Number
BGBC5574V
BGBC5573V
BGBC5187V
BGBC5186V
BGBB8204V

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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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