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13674-87-8

13674-87-8 structure
13674-87-8 structure
  • Name: TDCPP
  • Chemical Name: Phosphoric Acid Tris(1,3-Dichloro-2-Propyl) Ester
  • CAS Number: 13674-87-8
  • Molecular Formula: C9H15Cl6O4P
  • Molecular Weight: 430.905
  • Catalog: Catalysts and additives Plastic rubber additive
  • Create Date: 2018-05-25 08:00:00
  • Modify Date: 2025-08-22 18:52:26
  • 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.
Name Phosphoric Acid Tris(1,3-Dichloro-2-Propyl) Ester
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
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
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.
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
Water Solubility <0.1 g/100 mL at 24 ºC

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
Symbol GHS08 GHS09
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
96-23-1 structure

96-23-1

~%

13674-87-8 structure

13674-87-8

Literature: Journal of the Chemical Society, , p. 826
106-89-8 structure

106-89-8

~%

13674-87-8 structure

13674-87-8

Literature: J. Gen. Chem. USSR (Engl. Transl.), , vol. 36, # 8 p. 1454 - 1459,1461 - 1464
Precursor  2

DownStream  0

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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