1,2-Dibromo-3-chloropropane

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"DBCP" redirects here. For the database connection pool implementation, see Apache Commons.
1,2-Dibromo-3-chloropropane
Names
Preferred IUPAC name
1,2-Dibromo-3-chloropropane
Other names
Dibromochloropropane
Identifiers
3D model (
JSmol
)
Abbreviations DBCP
ChemSpider
ECHA InfoCard
 100.002.255 Edit this at Wikidata
KEGG
UNII
  • InChI=1S/C3H5Br2Cl/c4-1-3(5)2-6/h3H,1-2H2 checkY
    Key: WBEJYOJJBDISQU-UHFFFAOYSA-N checkY
  • InChI=1/C3H5Br2Cl/c4-1-3(5)2-6/h3H,1-2H2
    Key: WBEJYOJJBDISQU-UHFFFAOYAN
  • BrC(CBr)CCl
Properties
C3H5Br2Cl
Molar mass 236.33 g/mol
Appearance Dense colorless liquid
Odor pungent odor at high concentrations
Density 2.05 g/mL
Melting point 6.1 °C (43.0 °F; 279.2 K)
Boiling point 195.5 °C (383.9 °F; 468.6 K)
0.1%[1]
Vapor pressure 0.8 mmHg (20 °C)[1]
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 carcinogen[1]
GHS labelling:
GHS06: ToxicGHS08: Health hazard[2]
H301, H340, H350, H360, H373, H412[2]
P201, P273, P301+P310, P308+P313[2]
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 1: Normally stable, but can become unstable at elevated temperatures and pressures. E.g. calciumSpecial hazards (white): no code
2
1
1
Flash point 76.7 °C (170.1 °F; 349.8 K)
NIOSH (US health exposure limits):
PEL (Permissible)
 TWA 0.001 ppm [1]
REL (Recommended)
 Ca[1]
IDLH
(Immediate danger)
 Ca, N.D.[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

1,2-Dibromo-3-chloropropane (dibromochloropropane), better known as DBCP, is the organic compound with the formula BrCH(CH2Br)(CH2Cl). It is a dense colorless liquid although commercial samples often appear amber or even brown. It is the active ingredient in the nematicide Nemagon, also known as Fumazone.

It is a soil

ground water
remains a problem for many communities for years after end of use.

Stereoisomerism

1,2-Dibromo-3-chloropropane
(2 stereoisomers)
(R)-1,2-Dibrom-3-chlorpropan
(R)-configuration 		(S)-1,2-Dibrom-3-chlorpropan
(S)-configuration

Uses

Sources and potential exposure

Human exposure to DBCP could result from the ingestion of contaminated drinking water and food. Exposure could also result from inhalation and/or skin contact with a product containing DBCP.

In the past, release of DBCP to the environment occurred primarily from its fumigant and nematocide uses; because of the cancellation of all DBCP uses, environmental exposure is expected to decline with time.

Examples of persistence

DBCP residues have persisted in

wells had to be shut down at that time.[5]

Lawsuits

Workers at the

Dow Chemical plant producing DBCP were made sterile by exposure to DBCP. These male reproductive effects were consistent with animal experiments showing that DBCP sterilizes rabbits. One contract worker at the production plant successfully sued the company. Most workers remained with the company and in a company sponsored medical program until the facility was sold in 1987. At that time, some of the workers did file suit against the company. However, the suit was denied due to statute of limitations
issues.

Most uses of the chemical in the United States were banned in 1977. Amid growing concerns over DBCP's effects on male workers, Dow ceased production and reclaimed DBCP that had been shipped to its users.

However, despite warnings from Dow about its health effects, the

billion in judgments in similar lawsuits.[10]

Workers in

Dole Food Company, who used it on overseas crops, but never used it in Côte d'Ivoire. The United States Court of Appeals for the Ninth Circuit ruled against the workers in September 2008, stating that the plaintiffs did not show that the defendants had "specific intent" to intend harm against the workers and the citizens of the country. To be found guilty of genocide the defendant must have knowingly set out to commit the offense.[11][12]

Safety

DBCP causes a dramatic decrease in male fertility, ranging from oligospermia (low sperm count) to azoospermia (lack of sperm).[13]

References

  1. ^ a b c d e f NIOSH Pocket Guide to Chemical Hazards. "#0184". National Institute for Occupational Safety and Health (NIOSH).
  2. ^ a b c Sigma-Aldrich Co., 1,2-Dibromo-3-chloropropane. Retrieved on 2013-07-20.
  3. ^ Hazard Summary Archived 2016-03-22 at the Wayback Machine. - United States Environmental Protection Agency. - EPA.gov.
  4. ^ Spano, John. - "Dole Must Pay $2.5 Million in Punitive Damages". - Los Angeles Times. - November 15, 2007.
  5. ^ "Environmental Screening Analysis, Tully Road Properties, Turlock, California". - Earth Metrics Incorporated. - Report 7826, San Mateo, California. - March, 1989
  6. ^ "U.S. Court Refuses To Enforce Nicaragua Judgment Against Dole Food - Update" Archived 2015-12-08 at the Wayback Machine. - rttnews.com. - October 26, 2009
  7. ^ Spano, John. - "Dole must pay farmworkers $3.2 million" Archived 2019-08-21 at the Wayback Machine. - Los Angeles Times. - November 6, 2007.
  8. FoxNews.com
    . - July 15, 2010
  9. ^ Hallman, Ben. - "Finding Plaintiffs Lawyers Committed Fraud, Judge Dismisses Tort Cases Against Dole and Dow Chemical" Archived 2012-11-08 at the Wayback Machine. - The American Lawyer. - April 27, 2009.
  10. ^ Keating, Gina. - "Judge throws out Dole "bananeros" cases, citing fraud"[dead link]. - Forbes. - April 24, 2009.
  11. ^ Abagninin v. AMVAC Chemical Corp. Archived 2008-11-06 at the Wayback Machine. - United States Court of Appeals for the Ninth Circuit. - September 24, 2008. - (Adobe Acrobat *.PDF document).
  12. ^ Williams, Carol J. - "Appeals Court Rules Against Ivory Coast Farm Workers". - Los Angeles Times. - September 24, 2008.
  13. PMID 19092487
    .

External links
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