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CAS 13674-87-8 | TDCPP

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Common Name	TDCPP
CAS Number	13674-87-8	Molecular Weight	430.905
Density	1.5±0.1 g/cm3	Boiling Point	457.4±40.0 °C at 760 mmHg
Molecular Formula	C₉H₁₅Cl₆O₄P	Melting Point	-64°C
MSDS	ChineseUSA	Flash Point	377.7±35.0 °C
Symbol	GHS08, GHS09	Signal Word	Warning

Names

Name	Phosphoric Acid Tris(1,3-Dichloro-2-Propyl) Ester
Synonym	More Synonyms

TDCPP BiologicalActivity

Description	TDCPP is a chlorinated analog of tris(2,3-dibromopropyl)phosphate (Tris) which is one of the most detected organophosphorus flame retardants (OPFRs) in the environment.
Related Catalog	Signaling Pathways >>Others >>OthersResearch Areas >>Cancer
In Vitro	Exposure to TDCPP does not significantly affect cell viability until at concentration >68 μg/mL. HCECs show a 16% cell viability loss after exposing to 136 μg/mL TDCPP. Moreover, TDCPP induces a sharp decrease in viable cells (87%) after exposing to ≥272 μg/mL TDCPP. Based on cell viability, the LC50 value for TDCPP is 202 μg/mL using a nonlinear regression. Compare to controls, TDCPP-exposed cells exhibit a concentration-dependent increase in apoptosis. Anti-apoptotic Bcl-2 protein expression is increased to 1.4 fold after exposing to 2 μg/mL TDCPP, 1.2-folds at 20 μg/mL but dynamically decreased to 0.4 fold at 200 μg/mL compare to control. The caspase-3 activity is increased to 2.1 folds of the control at 200 μg/mL TDCPP[1]. TDCPP inhibits cell growth at lower concentrations (IC50 of 27 μM), while cell viability and toxicity are affected at higher concentrations (IC50 of 171 μM and 168 μM, respectively)[2].
Kinase Assay	The cellular ATP contents are determined in HCECs grown in DMEM containing 0, 2, 20, or 200 μg/mL TDCPP using a luciferase-based ATP assay kit according to the manufacturer's guideline. Briefly, after 24 h exposure, HCECs are lysed with lysis buffer. Lysates are then centrifuged at 12,000 g at 4°C for 5 min. Then, 100 μL of supernatant is mixed with 100 μL ATP detection working dilution. Luminance is examined by an fluorescence microplate reader[1].
Cell Assay	To examine the effects of TDCPP on cell viability, HCECs are planted into 96-well plate (100 μL/well) at density of 1×105 cells/mL overnight. Then, the medium is changed into fresh medium containing 0.034, 0.34, 3.4, 34, 68, 136, 272, or 340 μg/mL of TDCPP and solvent vehicle (0.1%, v/v) and incubated for 24 h. Cell viability is detected using CCK-8 cell viability assay kit according to the manufacturer's instructions. After exposure, cellular morphology is observed and recorded by an inverted microscopy[1].
References	[1]. Xiang P, et al. Effects of organophosphorus flame retardant TDCPP on normal human corneal epithelial cells: Implications for human health. Environ Pollut. 2017 Nov;230:22-30. [2]. Killilea DW, et al. Flame retardant tris(1,3-dichloro-2-propyl)phosphate (TDCPP) toxicity is attenuated by N-acetylcysteine in human kidney cells. Toxicol Rep. 2017 May 17;4:260-264.

Chemical & Physical Properties

Density	1.5±0.1 g/cm3
Boiling Point	457.4±40.0 °C at 760 mmHg
Melting Point	-64°C
Molecular Formula	C₉H₁₅Cl₆O₄P
Molecular Weight	430.905
Flash Point	377.7±35.0 °C
Exact Mass	427.883911
PSA	54.57000
LogP	1.79
Vapour Pressure	0.0±1.1 mmHg at 25°C
Index of Refraction	1.497
InChIKey	ASLWPAWFJZFCKF-UHFFFAOYSA-N
SMILES	O=P(OC(CCl)CCl)(OC(CCl)CCl)OC(CCl)CCl
Water Solubility	<0.1 g/100 mL at 24 ºC

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: UB1473000

CAS REGISTRY NUMBER :: 13674-87-8

BEILSTEIN REFERENCE NO. :: 1715458

LAST UPDATED :: 199710

DATA ITEMS CITED :: 17

MOLECULAR FORMULA :: C9-H15-Cl6-O4-P

MOLECULAR WEIGHT :: 430.91

WISWESSER LINE NOTATION :: G1Y1GOPO&OY1G1GOY1G1G

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 1850 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 2250 mg/kg

TOXIC EFFECTS :: Sense Organs and Special Senses (Eye) - effect, not otherwise specified Behavioral - tremor Behavioral - convulsions or effect on seizure threshold

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Administration onto the skin

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: >23700 mg/kg

TOXIC EFFECTS :: Behavioral - irritability Gastrointestinal - hypermotility, diarrhea Biochemical - Enzyme inhibition, induction, or change in blood or tissue levels - true cholinesterase

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 15561 mg/kg/13W-C

TOXIC EFFECTS :: Gastrointestinal - tumors Kidney, Ureter, Bladder - tumors Blood - pigmented or nucleated red blood cells

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: 16800 mg/kg/12W-I

TOXIC EFFECTS :: Liver - changes in liver weight Kidney, Ureter, Bladder - changes in bladder weight

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Bird - chicken

DOSE/DURATION :: 24 gm/kg/5D-C

TOXIC EFFECTS :: Related to Chronic Data - death

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 58400 mg/kg/2Y-C

TOXIC EFFECTS :: Tumorigenic - Carcinogenic by RTECS criteria Liver - tumors

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 3600 mg/kg

SEX/DURATION :: female 7-15 day(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - litter size (e.g. # fetuses per litter; measured before birth) Reproductive - Effects on Embryo or Fetus - fetal death

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 3600 mg/kg

SEX/DURATION :: female 7-15 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Embryo or Fetus - fetal death

MUTATION DATA

TYPE OF TEST :: Morphological transformation

TEST SYSTEM :: Rodent - hamster Embryo

DOSE/DURATION :: 20 umol/L

REFERENCE :: APTOA6 Acta Pharmacologica et Toxicologica. (Copenhagen, Denmark) V.1-59, 1945-86. For publisher information, see PHTOEH Volume(issue)/page/year: 56,20,1985 *** REVIEWS *** TOXICOLOGY REVIEW CTOXAO Clinical Toxicology. (New York, NY) V.1-18, 1968-81. For publisher information, see JTCTDW. Volume(issue)/page/year: 17,101,1980

Safety Information

Symbol	GHS08, GHS09
Signal Word	Warning
Hazard Statements	H351-H411
Precautionary Statements	P273-P281
Personal Protective Equipment	Eyeshields;Faceshields;full-face respirator (US);Gloves;multi-purpose combination respirator cartridge (US);type ABEK (EN14387) respirator filter
Hazard Codes	Xn: Harmful;N: Dangerous for the environment;
Risk Phrases	R20/21/22
Safety Phrases	S26-S36/37/39-S61
RIDADR	UN 3082 9/PG 3
RTECS	UB1473000
HS Code	2919900090

Customs

HS Code	2919900090
Summary	2919900090 other phosphoric esters and their salts, including lactophosphates; their halogenated, sulphonated, nitrated or nitrosated derivatives。supervision conditions:AB(certificate of inspection for goods inward,certificate of inspection for goods outward)。VAT:17.0%。tax rebate rate:9.0%。MFN tariff:6.5%。general tariff:30.0%

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Synonyms

Phosphoric Acid Tris(1,3-dichloro-2-propyl) Ester

Tris(1,3-dichloro-2-propanyl) phosphate

Tri(β,β'-dichloroisopropyl) phosphate

MFCD00083121

Tris(1,3-dichloropropan-2-yl) phosphate

TDCPP

Tris(1,3-dichloroisopropyl) phosphate

EINECS 237-159-2

Tris(1,3-dichloro-2-propyl) phosphate

1,3-Dichloro-2-propanol phosphate (3:1)

Phosphoric acid, tris(1,3-dichloro-2-propyl) ester

G1Y1GOPO&OY1G1G&OY1G1G

1,3-Dichloro-2-propanol phosphate (Phosphoric acid tris(1,3-dichloro-2-propyl ester)

Tris(2,2′-dichloroisopropyl) phosphate

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