1,2-Dibromo-3-chloropropane

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1,2-Dibromo-3-chloropropane[edit | edit source]

Structural formula of 1,2-Dibromo-3-chloropropane
3D model of 1,2-Dibromo-3-chloropropane

1,2-Dibromo-3-chloropropane (DBCP) is a halogenated hydrocarbon with the chemical formula C_H_Br_Cl. It is a colorless liquid that was primarily used as a soil fumigant and nematocide in agriculture.

Chemical Properties[edit | edit source]

1,2-Dibromo-3-chloropropane is a member of the organohalogen compound family. It is characterized by the presence of two bromine atoms and one chlorine atom attached to a three-carbon propane backbone. The compound is known for its high density and low solubility in water, but it is soluble in organic solvents.

Synthesis[edit | edit source]

The synthesis of 1,2-Dibromo-3-chloropropane typically involves the halogenation of allyl chloride with bromine. This reaction results in the addition of bromine atoms across the double bond of allyl chloride, forming the dibromo derivative.

Uses[edit | edit source]

1,2-Dibromo-3-chloropropane was widely used as a soil fumigant and nematocide to control nematodes in agricultural settings. Its use was particularly prevalent in the cultivation of crops such as pineapples, soybeans, and tomatoes.

Health Effects[edit | edit source]

Exposure to 1,2-Dibromo-3-chloropropane has been associated with adverse health effects. It is known to be a carcinogen and can cause reproductive harm. Workers exposed to DBCP in manufacturing and agricultural settings reported cases of sterility and other reproductive issues.

Regulation[edit | edit source]

Due to its toxicological profile, the use of 1,2-Dibromo-3-chloropropane has been heavily restricted or banned in many countries. In the United States, the Environmental Protection Agency (EPA) banned its use in 1979, except for certain limited applications.

Environmental Impact[edit | edit source]

DBCP is persistent in the environment and can contaminate groundwater. Its use has led to concerns about long-term environmental and health impacts, prompting regulatory actions to limit its application.

Gallery[edit | edit source]

  • (R)-1,2-Dibromo-3-chloropropane

  • (S)-1,2-Dibromo-3-chloropropane

Related Pages[edit | edit source]

  • 1,2-Dibromo-3-chloropropane structural formula

  • 1,2-Dibromo-3-chloropropane 3D model

  • (R)-1,2-Dibromo-3-chloropropane

  • (S)-1,2-Dibromo-3-chloropropane

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Contributors: Prab R. Tumpati, MD