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676713

Sigma-Aldrich

1,2-Dibromo-3-chloropropane

97%

Synonym(s):

DBCP

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About This Item

Linear Formula:
CH2BrCHBrCH2Cl
CAS Number:
96-12-8
Molecular Weight:
236.33
Beilstein:
1732077
EC Number:
202-479-3
MDL number:
MFCD00039365
UNSPSC Code:
12352100
PubChem Substance ID:
24885325
NACRES:
NA.22

Quality Level

100

Assay

97%

refractive index

n/D 1.5542

bp

60-65 °C/7.5 mmHg

density

2.081 g/mL at 25 °C

functional group

bromo
chloro

SMILES string

ClCC(Br)CBr

InChI

1S/C3H5Br2Cl/c4-1-3(5)2-6/h3H,1-2H2

InChI key

WBEJYOJJBDISQU-UHFFFAOYSA-N

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Application

1,2-Dibromo-3-chloropropane can be used to prepare:
  • Tritium radiolabeled dibromochloropropane.
  • L-Glutathione conjugates, which are used to alkylate the DNA to yield N7-guanyl adducts.

Pictograms

Skull and crossbonesHealth hazard
GHS06,GHS08

Signal Word

Danger

Hazard Classifications

Acute Tox. 3 Oral - Aquatic Chronic 3 - Carc. 1B - Muta. 1B - Repr. 1A - STOT RE 2 Oral

Target Organs

Testes

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flash Point(F)

170.1 °F

Flash Point(C)

76.7 °C

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
MKCR9284
MKCF2927
MKBG6103V
17124ME

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An improved synthesis of labelled dibromochloropropane
Buchman O, et al.
Journal of Labelled Compounds & Radiopharmaceuticals, 18(12), 1713-1719 (1981)
Isolation and characterization of N7-guanyl adducts derived from 1, 2-dibromo-3-chloropropane
Humphreys WG, et al.
Chemical Research in Toxicology, 4(4), 445-453 (1991)
S Teramoto et al.
Mutation research, 221(1), 1-9 (1989-07-01)
1,2-Dibromo-3-chloropropane (DBCP) is a nematocide, which has been used extensively as a soil fumigant in agriculture. Since sterility was found among male workers involved in the manufacture of DBCP, great concern has been focused on the genetic hazards of DBCP.
T Bosma et al.
Applied and environmental microbiology, 65(10), 4575-4581 (1999-10-03)
Trihalogenated propanes are toxic and recalcitrant organic compounds. Attempts to obtain pure bacterial cultures able to use these compounds as sole carbon and energy sources were unsuccessful. Both the haloalkane dehalogenase from Xanthobacter autotrophicus GJ10 (DhlA) and that from Rhodococcus
Marvin L Meistrich et al.
Toxicological sciences : an official journal of the Society of Toxicology, 76(2), 418-426 (2003-09-30)
The exposure of men to the nematocide dibromochloropropane (DBCP) has caused prolonged oligo- and azoospermia, which occasionally reverses spontaneously. We recently demonstrated that in testes of rats treated with a dose of DBCP sufficient to reduce the percentage of tubules
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