|Preferred IUPAC name
3D model (JSmol)
CompTox Dashboard (EPA)
|Molar mass||147.00 g·mol−1|
|Density||1.25 g/cm3, solid|
|Melting point||53.5 °C (128.3 °F; 326.6 K)|
|Boiling point||174 °C (345 °F; 447 K)|
|10.5 mg/100 mL (20 °C)|
|Vapor pressure||1.3 mmHg (20 °C)|
|Occupational safety and health (OHS/OSH):|
|H302, H315, H317, H319, H332, H335, H351, H410|
|P201, P202, P261, P264, P270, P271, P272, P273, P280, P281, P301+P312, P302+P352, P304+P312, P304+P340, P305+P351+P338, P308+P313, P312, P321, P330, P332+P313, P333+P313, P337+P313, P362, P363, P391, P403+P233, P405, P501|
|NFPA 704 (fire diamond)|
|Flash point||66 °C (151 °F; 339 K)|
|Lethal dose or concentration (LD, LC):|
LD50 (median dose)
|500 mg/kg (rat, oral)|
2950 mg/kg (mouse, oral)
2512 mg/kg (rat, oral)
2830 mg/kg (rabbit, oral)
LDLo (lowest published)
|857 mg/kg (human, oral)|
4000 mg/kg (rat, oral)
2800 mg/kg (guinea pig, oral)
|NIOSH (US health exposure limits):|
|TWA 75 ppm (450 mg/m3)|
IDLH (Immediate danger)
|Ca [150 ppm]|
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
|what is ?)(|
1,4-Dichlorobenzene (1,4-DCB, p-DCB, or para-dichlorobenzene, sometimes abbreviated as PDCB or para) is an organic compound with the formula C6H4Cl2. This colorless solid has a strong odor. The molecule consists of a benzene ring with two chlorine atoms (replacing hydrogen atoms) on opposing sites of the ring.
It is used as a disinfectant, pesticide, and deodorant, most familiarly in mothballs in which it is a replacement for the more traditional naphthalene because of naphthalene's greater flammability (though both chemicals have the same NFPA 704 rating). It is also used as a precursor in the production of the chemically and thermally resistant polymer poly(p-phenylene sulfide).
The chief impurity is the 1,2 isomer. The compound can be purified by fractional crystallization, taking advantage of its relatively high melting point of 53.5 °C; the isomeric dichlorobenzenes and chlorobenzene melt well below room temperature.
p-DCB is used to control moths, molds, and mildew. It also finds use as a disinfectant in waste containers and restrooms and is the characteristic smell associated with urinal cakes. Its usefulness for these applications arises from p-DCB's low solubility in water and its relatively high volatility: it sublimes readily near room temperature.
Nitration gives 1,4-dichloronitrobenzene, a precursor to commercial dyes and pigments. The chloride sites on p-DCB can be substituted with hydroxylamine and sulfide groups. In a growing application, p-DCB is the precursor to the high performance polymer poly(p-phenylene sulfide):
The United States Department of Health and Human Services (DHHS) and the International Agency for Research on Cancer (IARC) have determined that p-DCB may reasonably be anticipated to be a carcinogen. This has been indicated by animal studies, although a full-scale human study has not been done.
The United States Environmental Protection Agency (EPA) has set a target maximum contaminant level of 75 micrograms of p-DCB per liter of drinking water (75 μg/L), but publishes no information on the cancer risk. p-DCB is also an EPA-registered pesticide. The United States Occupational Safety and Health Administration (OSHA) has set a maximum level of 75 parts of p-DCB per million parts air in the workplace (75 ppm) for an 8-hour day, 40-hour workweek.
Under California's Proposition 65, p-DCB is listed as "known to the State to cause cancer". A mechanism for the carcinogenic effects of mothballs and some types of air fresheners containing p-DCB has been identified in roundworms.