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1,3-Dichloropropan-2-ol

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1,3-Dichloropropan-2-ol
Names
Preferred IUPAC name
1,3-Dichloropropan-2-ol
Other names
1,3-Dichloropropanol-2; 1,3-Dichloroisopropyl alcohol; 1,3-Dichloro-2-propanol; 1,3-Dichloroisopropanol; Glycerol-α,γ-dichlorohydrin; α-Dichlorohydrin; 1,3-DCP; DC2P
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.002.266 Edit this at Wikidata
EC Number
  • 202-491-9
KEGG
RTECS number
  • UB1400000
UNII
UN number 2750
  • InChI=1S/C3H6Cl2O/c4-1-3(6)2-5/h3,6H,1-2H2
    Key: DEWLEGDTCGBNGU-UHFFFAOYSA-N
  • C(C(CCl)O)Cl
Properties
C3H6Cl2O
Molar mass 128.98 g·mol−1
Appearance Colorless liquid[1]
Odor Phenol-like[1]
Density 1.39 g/cm3 (20 °C)[1]
Melting point −4 °C (25 °F; 269 K)[1]
Boiling point 175 °C (347 °F; 448 K)[1]
110 g/L (20 °C)[1]
Hazards
GHS labelling:
GHS06: ToxicGHS07: Exclamation markGHS08: Health hazard
Danger
H301, H311, H312, H336, H350, H370, H373
P201, P202, P260, P261, P264, P270, P271, P280, P281, P301+P310, P302+P352, P304+P340, P307+P311, P308+P313, P312, P314, P321, P322, P330, P361, P363, P403+P233, P405, P501
Flash point 74 °C (165 °F; 347 K)[1]
Lethal dose or concentration (LD, LC):
110 mg/kg (oral, rat)[1]
1080 mg/kg (dermal, rabbit)[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

1,3-Dichloropropan-2-ol (1,3-DCP) is an organic compound with the formula HOCH2CHClCH2Cl. It is a colorless liquid. It is an intermediate in the production of epichlorohydrin.[2][3]

1,3-DCP is a believed to be a carcinogen and mutagen.[4] The International Agency for Research on Cancer classifies it as a Group 2B carcinogen ("possibly carcinogenic to humans").[5]

Along with 3-monochloropropane-1,2-diol (3-MCPD), 1,3-DCP is found in some Asian style sauces such as soy sauce and oyster sauce.[6][7][8]

References

  1. ^ a b c d e f g h i Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health
  2. ^ "1,3-Dichloro-2-propanol". Some Chemicals Present in Industrial and Consumer Products, Food and Drinking-Water. International Agency for Research on Cancer. 2013.
  3. ^ Howard, Philip H.; Muir, Derek C. G. (2010). "Identifying New Persistent and Bioaccumulative Organics Among Chemicals in Commerce". Environmental Science & Technology. 44 (7): 2277–2285. Bibcode:2010EnST...44.2277H. doi:10.1021/es903383a. PMID 20163179.
  4. ^ "Evidence on the Carcinogenicity of 1,3-Dichloro-2-Propanol (1,3-DCP; α,γ-Dichlorohydrin)" (PDF). Reproductive and Cancer Hazard Assessment Branch Office of Environmental Health Hazard Assessment, California Environmental Protection Agency. June 2010.
  5. ^ "List of Classifications". International Agency for Research on Cancer.
  6. ^ Genualdi, Susan; Nyman, Patricia; Dejager, Lowri (2017). "Simultaneous Analysis of 3-MCPD and 1,3-DCP in Asian Style Sauces Using QuEChERS Extraction and Gas Chromatography–Triple Quadrupole Mass Spectrometry". Journal of Agricultural and Food Chemistry. 65 (4): 981–985. doi:10.1021/acs.jafc.6b05051. PMC 5450852. PMID 28064506.
  7. ^ Crews, C; Lebrun, G; Brereton, P. A (2002). "Determination of 1,3-dichloropropanol in soy sauces by automated headspace gas chromatography-mass spectrometry". Food Additives and Contaminants. 19 (4): 343–349. doi:10.1080/02652030110098580. PMID 11962691. S2CID 28748623.
  8. ^ Lee, Bai Qin; Khor, Sook Mei (2015). "3-Chloropropane-1,2-diol (3-MCPD) in Soy Sauce: A Review on the Formation, Reduction, and Detection of This Potential Carcinogen" (PDF). Comprehensive Reviews in Food Science and Food Safety. 14 (1): 48–66. doi:10.1111/1541-4337.12120. PMID 33401813.
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