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13674-84-5

13674-84-5 Structure

13674-84-5 Structure
IdentificationMore
[Name]

Phosphoric acid tris(2-chloro-1-methylethyl) ester
[CAS]

13674-84-5
[Synonyms]

Phosphoric acid tris(2-chloro-1-methylethyl) ester
TCPP
TRIS(1-CHLORO-2-PROPYL) PHOSPHATE
TRIS(1-CHLOROPROPYL)PHOSPHATE
TRIS(2-CHLORO-1-METHYLETHYL) PHOSPHATE
TRIS(CHLOROISOPROPYL)PHOSPHATE
TRIS(MONOCHLOROPROPYL) PHOSPHATE
1-Chloro-2-propanolphosphate(3:1)
1-chloro-2-propanophosphate(3:1)
2-propanol,1-chloro,phosphate
2-propanol,1-chloro,phosphate(3:1)
2-Propanol,1-chloro-,phosphate(3:1)
amgardtmcp
hostaflamop820
tri-(2-chloroisopropyl)phosphate
tris(2-chloroisopropyl)phosphate
TCPP (FYROL PCF)
TRIS(2-CHLOROPROPYL)PHOSPHATE (TCPP)
TcppTris(1-Chloro-2-Propyl)Phosphate]
TRIS-(1-CHLORO-2-PROPYL)PHOSPHATE (TCPP)
[EINECS(EC#)]

237-158-7
[Molecular Formula]

C9H18Cl3O4P
[MDL Number]

MFCD00040408
[Molecular Weight]

327.57
[MOL File]

13674-84-5.mol
Chemical PropertiesBack Directory
[Melting point ]

-39.9°C
[Boiling point ]

270°C
[density ]

1.28
[refractive index ]

1.460~1.466 (20℃/D)
[Fp ]

-218 °C
[storage temp. ]

Sealed in dry,Room Temperature
[solubility ]

DMSO (Slightly), Methanol (Slightly)
[form ]

liquid
[color ]

Clear Colourless
[Odor]

mild odor
[Water Solubility ]

<0.1 g/100 mL at 19.5 ºC
[BRN ]

1842347
[Henry's Law Constant]

1.6×102 mol/(m3Pa) at 25℃, HSDB (2015)
[Stability:]

Moisture Sensitive
[Major Application]

agriculture
[InChI]

1S/C9H18Cl3O4P/c1-7(4-10)14-17(13,15-8(2)5-11)16-9(3)6-12/h7-9H,4-6H2,1-3H3
[InChIKey]

KVMPUXDNESXNOH-UHFFFAOYSA-N
[SMILES]

CC(CCl)OP(=O)(OC(C)CCl)OC(C)CCl
[CAS DataBase Reference]

13674-84-5(CAS DataBase Reference)
[NIST Chemistry Reference]

2-Propanol, 1-chloro-, phosphate (3:1)(13674-84-5)
[EPA Substance Registry System]

13674-84-5(EPA Substance)
Safety DataBack Directory
[Symbol(GHS) ]

Exclamation Mark (GHS07)
GHS07
[Signal word ]

Warning
[Hazard statements ]

H302
[Precautionary statements ]

P301+P312+P330
[Hazard Codes ]

Xn
[Risk Statements ]

R22:Harmful if swallowed.
R37:Irritating to the respiratory system.
[WGK Germany ]

1
[RTECS ]

TC9000000
[TSCA ]

TSCA listed
[REACH Registrations]

Inactive
[Storage Class]

10 - Combustible liquids
[Hazard Classifications]

Acute Tox. 4 Oral
[Hazardous Substances Data]

13674-84-5(Hazardous Substances Data)
Hazard InformationBack Directory
[General Description]

Clear colorless viscous liquid.
[Reactivity Profile]

TRIS(1-CHLORO-2-PROPYL) PHOSPHATE(13674-84-5) may hydrolyze under acidic or alkaline conditions.
[Air & Water Reactions]

Insoluble in water.
[Health Hazard]

ACUTE/CHRONIC HAZARDS: When heated to decomposition this chemical emits very toxic fumes.
[Fire Hazard]

This compound is probably combustible.
[Chemical Properties]

Tris(2-chloro-1-methylethyl) phosphate is clear colorless oily liquid with high water solubility and low lipophilicity (as indicated by logKOW). This substance ismanufactured as a reactionmixture, which contains four isomers. It is the primary isomer in the mixture at 50–85% weight/weight (w/w), followed by bis(1- chloro-2-propyl)-2-chloropropyl phosphate [15–40% (w/w); CASRN: 76025-08-6], bis(2-chloropropyl)-1-chloro-2-propyl phosphate [<15% (w/w); CASRN: 76649-15-5], and tris(2- chloropropyl) phosphate [<1% (w/w); CASRN: 6145-73-9] (EURAR, 2008).
[Uses]

Tris(1-chloro-2-propyl) Phosphate is a flame retardant of low hydrolytic stability, used in polyurethane (PU) rigid and flexible foam, PVC, EVA and phenolics and epoxy resin.
[Definition]

ChEBI:Tris(1-chloropropan-2-yl) phosphate is a trialkyl phosphate.
[Toxicology]

Tris(1-Chloro-2-Propyl) Phosphate (TCPP) is considered a suspected carcinogenic, suspected reprotoxic, and suspected PBT (persistent, bioaccumulative and toxic) and is a potential endocrine disruptor (ECHA, 2019).  Thus, the presence of TCPP in the receiving water can affect aquatic organisms and potentially affect human health.
[Synthesis]

Propylene oxide

75-56-9

Tris(1-Chloro-2-Propyl) Phosphate

13674-84-5

In a 5000 L stirred reactor equipped with a solid feeder, 4600 kg of phosphorous trichloride was first added, followed by 15 kg of anhydrous aluminum trichloride as a catalyst through the solid feeder and stirred at room temperature until complete dissolution. The propylene oxide was continuously dewatered by passing it through a dewatering tower equipped with a dewatering agent, calcium oxide, and then collected in a 10,000 L metering tank, and the water content was measured to be 28 PPM. 5,300 kg of the dewatered propylene oxide was added to the reactor and mixed with the trichlorophosphorus solution. The reaction temperature was controlled to be 65°C and the feed rate was adjusted to maintain the weight ratio of phosphorous trichloride to propylene oxide at 1:1.152. After the materials were added proportionally, the reaction was held at 65°C until the reaction was completed. At the end of the reaction, the crude product TCPP 16000L was transferred to a washing tank, 5000kg of 1% sodium hydroxide solution was added, stirred at 70℃ for 1 hour, and the lower layer was removed after standing and stratifying. Then add 5000kg of deionized water, stir for 1 hour at 70°C, and remove the water layer after static stratification. The washed TCPP crude product was transferred to a dehydration kettle for heating vacuum dehydration. Finally, 9715 kg of product was obtained by filtration with a yield of 98.1%. After GC analysis, the ether content in TCPP was 226PPM.

[storage]

Store at -20°C
[References]

[1] Patent: CN105085568, 2017, B. Location in patent: Paragraph 0031-0038
[2] J. Gen. Chem. USSR (Engl. Transl.), 1966, vol. 36, # 8, p. 1461 - 1464
[3] Zhurnal Obshchei Khimii, 1966, vol. 36, # 8, p. 1454 - 1459
Material Safety Data Sheet(MSDS)Back Directory
[msds information]

Phosphoric acid tris(2-chloro-1-methylethyl) ester(13674-84-5).msds
Well-known Reagent Company Product InformationBack Directory
[Sigma Aldrich]

13674-84-5(sigmaaldrich)
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