1,3-Dichloropropan-2-ol
Names
Preferred IUPAC name
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
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard
100.002.266
EC Number
KEGG
RTECS number
UNII
UN number
2750
InChI=1S/C3H6Cl2O/c4-1-3(6)2-5/h3,6H,1-2H2
Key: DEWLEGDTCGBNGU-UHFFFAOYSA-N
Properties
C 3 H 6 Cl 2 O
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 :
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).
Chemical compound
1,3-Dichloropropan-2-ol (1,3-DCP ) is an organic compound with the formula HOCH2 CHClCH2 Cl. 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]
^ a b c d e f g h i Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health
^ "1,3-Dichloro-2-propanol". Some Chemicals Present in Industrial and Consumer Products, Food and Drinking-Water . International Agency for Research on Cancer. 2013.
^ 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 .
^ "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.
^ "List of Classifications" . International Agency for Research on Cancer.
^ 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 .
^ 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 .
^ 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 .