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393665

Sigma-Aldrich

1,1-Dibromo-2,2-bis(chloromethyl)cyclopropane

90%, technical grade

Synonym(s):

1,1-Dibromo-2,2-bis(chloromethyl)cyclopropane

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About This Item

Linear Formula:
Br2C3H2(CH2Cl)2
CAS Number:
98577-44-7
Molecular Weight:
296.82
MDL number:
MFCD00101445
UNSPSC Code:
12352100
PubChem Substance ID:
24864531
NACRES:
NA.22

grade

technical grade

Quality Level

100

Assay

90%

form

solid

mp

48-50 °C (lit.)

functional group

bromo
chloro

SMILES string

ClCC1(CCl)CC1(Br)Br

InChI

1S/C5H6Br2Cl2/c6-5(7)1-4(5,2-8)3-9/h1-3H2

InChI key

RCRVZCIUKQNOIS-UHFFFAOYSA-N

Related Categories

General description

1,1-Dibromo-2,2-bis(chloromethyl)cyclopropane is a halogenated cyclopropane derivative. It has been reported to be synthesized from 3-chloro-2-(chloromethyl)-1-propene. It is formed as an intermediate during the synthesis of [1.1.1]propellane by Szeimies method.

Application

1,1-Dibromo-2,2-bis(chloromethyl)cyclopropane may be used as a starting material in the synthesis of [1.1.1]-propellane and ((3-ethynylbicyclo[1.1.1]pentan-1-yl)ethynyl)trimethylsilane.

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
STBK9437
STBK4263
STBG4724V
STBG3458V
STBG2376V

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[1.1. 1] Propellane: Reaction with Singlet Dihalocarbene.
Lee WB, et al.
Bull. Korean Chem. Soc., 19(3), 367-369 (1998)
Improved Preparations of 3-Chloro-2-(chloromethyl)-1-propene and 1, 1-Dibromo-2, 2-bis (chloromethyl) cyclopropane: Intermediates in the Synthesis of [1.1. 1] Propellane.
Lynch KM and Dailey WP
The Journal of Organic Chemistry, 60(14), 4666-4668 (1995)
Concerning the synthesis of [1.1. 1] propellane.
Belzner J, et al.
Chemische Berichte, 122(2), 397-398 (1989)
Cyprien Lemouchi et al.
Journal of the American Chemical Society, 135(25), 9366-9376 (2013-06-04)
The rod-like molecule bis((4-(4-pyridyl)ethynyl)bicyclo[2.2.2]oct-1-yl)buta-1,3-diyne, 1, contains two 1,4-bis(ethynyl)bicyclo[2.2.2]octane (BCO) chiral rotators linked by a diyne fragment and self-assembles in a one-dimensional, monoclinic C2/c centrosymmetric structure where two equilibrium positions with large occupancy imbalance (88% versus 12%) are identified on a

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