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35635

Sigma-Aldrich

cis-3,4-Dichlorocyclobutene

≥95.0% (GC)

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About This Item

Empirical Formula (Hill Notation):
C4H4Cl2
CAS Number:
Molecular Weight:
122.98
Beilstein/REAXYS Number:
1236770
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:

assay

≥95.0% (GC)

refractive index

n20/D 1.503

bp

74-76 °C/55 mmHg (lit.)

density

1.302 g/mL at 20 °C (lit.)

storage temp.

2-8°C

SMILES string

Cl[C@@H]1C=C[C@@H]1Cl

InChI

1S/C4H4Cl2/c5-3-1-2-4(3)6/h1-4H/t3-,4+

InChI key

MNOAQNJDZROAPA-ZXZARUISSA-N

General description

cis-3,4-Dichlorocyclobutene is a versatile synthon in organic synthesis of natural products.[1] Infrared multiphoton excitation of cis-3,4-dichlorocyclobutene was investigated by optoacoustic detection.[2] cis-3,4-Dichlorocyclobutene undergoes 1,3-dipolar cycloaddition reaction with several nitrile oxides to yield the mixtures of syn- and anti- 4-substituted 6,7-dichloro-2-oxa-3-azabicyclo[3.2.0]hept-3-enes.[3]

Application

cis-3,4-Dichlorocyclobutene may be used in the synthesis of cyclic polyether.[1]

pictograms

Flame

signalword

Warning

hcodes

Hazard Classifications

Flam. Liq. 3

Storage Class

3 - Flammable liquids

wgk_germany

WGK 3

flash_point_f

131.0 °F - closed cup

flash_point_c

55 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter


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Optoacoustic measurements of IR multiphoton excitation of cis-3, 4-dichlorocyclobutene.
Presser N, et al.
J. Chem. Phys. , 78(5), 2163-2169 (1983)
syn-anti-Isomerism in the cycloaddition of nitrile oxides to cis-3, 4-dichlorocyclobutene.
Bianchi G, et al.
Journal of the Chemical Society. Perkin Transactions 1, 137-140 (1974)

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