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HomeProduct name list1,1-DIBROMO-2,2-BIS(CHLOROMETHYL)CYCLOPROPANE

1,1-DIBROMO-2,2-BIS(CHLOROMETHYL)CYCLOPROPANE

  • CAS NO.:98577-44-7
  • Empirical Formula: C5H6Br2Cl2
  • Molecular Weight: 296.82
  • MDL number: MFCD00101445
  • EINECS: 627-508-0
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2023-12-28 18:13:10
1,1-DIBROMO-2,2-BIS(CHLOROMETHYL)CYCLOPROPANE Structural

What is 1,1-DIBROMO-2,2-BIS(CHLOROMETHYL)CYCLOPROPANE?

The Uses of 1,1-DIBROMO-2,2-BIS(CHLOROMETHYL)CYCLOPROPANE

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.

What are the applications of Application

1,1-Dibromo-2,2-bis(chloromethyl)cyclopropane is a synthesis reagent

Preparation

1000 ml 1,1-bis(chloromethyl)-2,2-dibromocyclopropane was added  to a vigorously stirred mixture within 10-15 min, which contains bromoform (370 ml, 4.24 mol), 3-chloro-2-chloromethyl-1-propane (250 g, 2.0 mol), 10 g benzyltriethylammonium chloride, 8 ml ethanol and 200 ml methylene chloride . The temperature was maintained between 25°-35° C. After overnight stirring, 500 ml methylene chloride was added and the thick black mixture was allowed to separate into layers. The top aqueous layer was removed and the bottom layer was gently washed with water (500 ml). 500 ml water was then added and well shaken. Separated the organic phase, treated the residual emulsion with solid sodium chloride and filtered through Celite. All aqueous layers were washed with methylene chloride. The organic extracts were combined, dried over magnesium sulfate, and filtered through Celite. Concentration and vacuum distillation gave the mixture of starting material and black-brown residue which was distilled on a Kugel-Rohr giving  semicrystalline fraction containing the product. Crystallization from 400 ml of pentane from a dry ice-acetone bath gave the white wet crystals. The crude product was dissolved in 400 ml of penfane, then 7.5 g silica gel was added.  Filtered and low temperature recrystallized again. Finally, obtain the product (1,1-DIBROMO-2,2-BIS(CHLOROMETHYL)CYCLOPROPANE )

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.

Properties of 1,1-DIBROMO-2,2-BIS(CHLOROMETHYL)CYCLOPROPANE

Melting point: 48-50 °C (lit.)
Boiling point: 277.1±10.0 °C(Predicted)
Density  2.065±0.06 g/cm3 (20 ºC 760 Torr)
storage temp.  Inert atmosphere,Room Temperature
form  powder to crystal
color  White to Orange to Green
InChI InChI=1S/C5H6Br2Cl2/c6-5(7)1-4(5,2-8)3-9/h1-3H2

Safety information for 1,1-DIBROMO-2,2-BIS(CHLOROMETHYL)CYCLOPROPANE

Signal word Warning
Pictogram(s)
ghs
Exclamation Mark
Irritant
GHS07
GHS Hazard Statements H315:Skin corrosion/irritation
H319:Serious eye damage/eye irritation
H335:Specific target organ toxicity, single exposure;Respiratory tract irritation
Precautionary Statement Codes P261:Avoid breathing dust/fume/gas/mist/vapours/spray.
P264:Wash hands thoroughly after handling.
P264:Wash skin thouroughly after handling.
P271:Use only outdoors or in a well-ventilated area.
P280:Wear protective gloves/protective clothing/eye protection/face protection.
P302+P352:IF ON SKIN: wash with plenty of soap and water.
P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

Computed Descriptors for 1,1-DIBROMO-2,2-BIS(CHLOROMETHYL)CYCLOPROPANE

InChIKey RCRVZCIUKQNOIS-UHFFFAOYSA-N
SMILES C1(Br)(Br)CC1(CCl)CCl

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