[ CAS No. 13674-84-5 ] {[proInfo.proName]}

Name: 13674-84-5|Tris(1-Chloro-2-Propyl) Phosphate|98% mixture of isomers
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3d Animation Molecule Structure of 13674-84-5

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Quality Control of [ 13674-84-5 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 13674-84-5 ]

SDS Specification

Alternatived Products of [ 13674-84-5 ]

Product Details of [ 13674-84-5 ]

CAS No. :	13674-84-5	MDL No. :	MFCD00040408
Formula :	C₉H₁₈Cl₃O₄P	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	KVMPUXDNESXNOH-UHFFFAOYSA-N
M.W :	327.57	Pubchem ID :	26176
Synonyms :

Calculated chemistry of [ 13674-84-5 ]

Physicochemical Properties

Num. heavy atoms :	17
Num. arom. heavy atoms :	0
Fraction Csp3 :	1.0
Num. rotatable bonds :	9
Num. H-bond acceptors :	4.0
Num. H-bond donors :	0.0
Molar Refractivity :	71.68
TPSA :	54.57 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	Yes
Log Kp (skin permeation) :	-6.46 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.95
Log Po/w (XLOGP3) :	2.59
Log Po/w (WLOGP) :	4.03
Log Po/w (MLOGP) :	2.23
Log Po/w (SILICOS-IT) :	3.21
Consensus Log Po/w :	3.0

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	0.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-2.91
Solubility :	0.404 mg/ml ; 0.00123 mol/l
Class :	Soluble
Log S (Ali) :	-3.38
Solubility :	0.135 mg/ml ; 0.000412 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.46
Solubility :	0.113 mg/ml ; 0.000344 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	2.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	4.93

Safety of [ 13674-84-5 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 13674-84-5 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 13674-84-5 ]
Downstream synthetic route of [ 13674-84-5 ]

[ 13674-84-5 ] Synthesis Path-Upstream 1~4

1
[ 75-56-9 ]
[ 13674-84-5 ]

Yield	Reaction Conditions	Operation in experiment
98.1%	at 20 - 65℃; Large scale	In a 5000 L stirred phosphorus oxychloride metering kettle equipped with a solid feeder, 4600 kg of phosphorus oxychloride was pumped first,Then add 15 kg of anhydrous aluminum trichloride catalyst through a solid feeder,Stirring at room temperature,Dissolved in phosphorus oxychloride solution,Propylene oxide continuously packed with a dehydrating agent calcium oxide dehydration tower and collected in a metering tank 10000L CCP 5300 kg,Detected by the water content of propylene oxide in the measuring tank is 28PPM,10000L simultaneously to the kettle and a solution of phosphorus oxychloride was added after the dehydration catalyst comprising propylene oxide,Feed process control reaction temperature at 65 ,Feed process control both the feed rate,Make it the weight ratio of phosphorus oxychloride:propylene oxide = 1: 1.152,Add the material in proportion at the same time continue to 65 insulation until the reaction is complete,The reaction will be good crude TCPP 16000L washing tank,Add 5000 kg of 1percent strength sodium hydroxide solution,At a temperature of 70 ° C,Stirred for 1 hour,Standing,Points to the base layer,Then add 5000 kg of deionized water,At a temperature of 70 ° C,Stirred for 1 hour,Standing,Points to the water layer,The washed TCPP crude into the dehydration kettle,Heating vacuum dehydration,The final product filter 9715 kg,The yield was 98.1percent;By GC analysis, TCPP ether content: 226PPM.

Reference： [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

2
[ 75-56-9 ]
[ 13674-84-5 ]
[ 76025-08-6 ]
[ 76649-15-5 ]

Reference： [1] Patent: US2008/227997, 2008, A1, . Location in patent: Page/Page column 3

3
[ 75-56-9 ]
[ 6145-73-9 ]
[ 14250-96-5 ]
[ 13674-84-5 ]
[ 76025-08-6 ]
[ 76649-15-5 ]

Reference： [1] Patent: US2008/227997, 2008, A1, . Location in patent: Page/Page column 3-4
[2] Patent: US2008/227997, 2008, A1, . Location in patent: Page/Page column 3-4

4
[ 75-56-9 ]
[ 6145-73-9 ]
[ 13674-84-5 ]
[ 76025-08-6 ]
[ 76649-15-5 ]

Reference： [1] Patent: US2008/227997, 2008, A1, . Location in patent: Page/Page column 3

[ 13674-84-5 ] Synthesis Path-Downstream 1~7

1
[ 75-56-9 ]
[ 13674-84-5 ]

Yield	Reaction Conditions	Operation in experiment
98.1%	With aluminum (III) chloride; calcium oxide; trichlorophosphate; at 20 - 65℃;Large scale;	In a 5000 L stirred phosphorus oxychloride metering kettle equipped with a solid feeder, 4600 kg of phosphorus oxychloride was pumped first,Then add 15 kg of anhydrous aluminum trichloride catalyst through a solid feeder,Stirring at room temperature,Dissolved in phosphorus oxychloride solution,Propylene oxide continuously packed with a dehydrating agent calcium oxide dehydration tower and collected in a metering tank 10000L CCP 5300 kg,Detected by the water content of propylene oxide in the measuring tank is 28PPM,10000L simultaneously to the kettle and a solution of phosphorus oxychloride was added after the dehydration catalyst comprising propylene oxide,Feed process control reaction temperature at 65 ,Feed process control both the feed rate,Make it the weight ratio of phosphorus oxychloride:propylene oxide = 1: 1.152,Add the material in proportion at the same time continue to 65 insulation until the reaction is complete,The reaction will be good crude TCPP 16000L washing tank,Add 5000 kg of 1% strength sodium hydroxide solution,At a temperature of 70 C,Stirred for 1 hour,Standing,Points to the base layer,Then add 5000 kg of deionized water,At a temperature of 70 C,Stirred for 1 hour,Standing,Points to the water layer,The washed TCPP crude into the dehydration kettle,Heating vacuum dehydration,The final product filter 9715 kg,The yield was 98.1%;By GC analysis, TCPP ether content: 226PPM.

Reference： [1]Patent: CN105085568,2017,B .Location in patent: Paragraph 0031-0038
[2]Journal of general chemistry of the USSR,1966,vol. 36,p. 1461 - 1464
Zhurnal Obshchei Khimii,1966,vol. 36,p. 1454 - 1459

3
[ 75-56-9 ]
[ 6145-73-9 ]
[ 14250-96-5 ]
[ 13674-84-5 ]
[ 76025-08-6 ]
[ 76649-15-5 ]

Yield	Reaction Conditions	Operation in experiment
	With trichlorophosphate;aluminum (III) chloride; at 40 - 65℃; for 6.0h;Product distribution / selectivity;	Example 2; Synthesis of tris(chloropropyl) phosphate (TCPP)The reactor (FIG. 2) charged with tris(chloropropyl) phosphate was fed continuously with propylene oxide (52.5 ml/h) and the catalyst titanium tetrachloride or aluminium chloride, in solution in phosphorus oxychloride (21.6 ml/h). The reaction was carried out with a pump circulation rate of 1638 ml/h in reactor 1. The catalyst concentration was varied, as was the reaction temperature. After 6 h in each case a sample of 250 ml of tris(chloropropyl) phosphate was taken. Following removal of volatile constituents under reduced pressure on a rotary evaporator (80 C., 15 mbar, 0.5 h), the product composition was analysed by gas chromatography (GC) (Table 2).Subsequently the products were purified in a three-stage water scrub. This was done by combining the sample of 250 ml of 5-molar HCl in a vol/vol ratio of 1:1 at 90 C. Following phase separation, the organic phase was washed with water, 0.2 m aqueous sodium hydroxide solution, and again with water, in each case in a vol/vol ratio of 1:1 at 90 C. After phase separation, the products were dried on a rotary evaporator for 2 h at 80 C. and 15 mbar and were analysed by gas chromatography, and their physical parameters were ascertained as well (Table 3).
	With trichlorophosphate;titanium tetrachloride; at 40 - 65℃; for 6.0h;Product distribution / selectivity;	Example 2; Synthesis of tris(chloropropyl) phosphate (TCPP)The reactor (FIG. 2) charged with tris(chloropropyl) phosphate was fed continuously with propylene oxide (52.5 ml/h) and the catalyst titanium tetrachloride or aluminium chloride, in solution in phosphorus oxychloride (21.6 ml/h). The reaction was carried out with a pump circulation rate of 1638 ml/h in reactor 1. The catalyst concentration was varied, as was the reaction temperature. After 6 h in each case a sample of 250 ml of tris(chloropropyl) phosphate was taken. Following removal of volatile constituents under reduced pressure on a rotary evaporator (80 C., 15 mbar, 0.5 h), the product composition was analysed by gas chromatography (GC) (Table 2).Subsequently the products were purified in a three-stage water scrub. This was done by combining the sample of 250 ml of 5-molar HCl in a vol/vol ratio of 1:1 at 90 C. Following phase separation, the organic phase was washed with water, 0.2 m aqueous sodium hydroxide solution, and again with water, in each case in a vol/vol ratio of 1:1 at 90 C. After phase separation, the products were dried on a rotary evaporator for 2 h at 80 C. and 15 mbar and were analysed by gas chromatography, and their physical parameters were ascertained as well (Table 3).

Reference： [1]Patent: US2008/227997,2008,A1 .Location in patent: Page/Page column 3-4
[2]Patent: US2008/227997,2008,A1 .Location in patent: Page/Page column 3-4

4
[ 75-56-9 ]
[ 6145-73-9 ]
[ 13674-84-5 ]
[ 76025-08-6 ]
[ 76649-15-5 ]

Yield	Reaction Conditions	Operation in experiment
	With trichlorophosphate;aluminum (III) chloride; at 50 - 95℃; for 6.0h;Product distribution / selectivity;	Example 1; Synthesis of tris(chloropropyl) phosphate (TCPP)The reactor (FIG. 2) charged with tris(chloropropyl) phosphate was fed continuously with propylene oxide (52.5 ml/h) and aluminium trichloride in solution in phosphorus oxychloride (21.6 ml/h). The reaction was carried out with a pump circulation rate of 1638 ml/h. The catalyst concentration was varied, as was the reaction temperature. After a run time of 6 h, samples of the tris(chloropropyl) phosphate discharged were taken, and the product composition was analysed by gas chromatography. Table 1 shows the conversion of the reaction, measured as residual propylene oxide (GC%), and the isomer composition, both as a function of the catalyst concentration and the reaction temperature. A depiction of the propylene conversion from Table 1 in graph form can be seen in FIG. 1.

Reference： [1]Patent: US2008/227997,2008,A1 .Location in patent: Page/Page column 3

5
[ 75-56-9 ]
[ 13674-84-5 ]
[ 76025-08-6 ]
[ 76649-15-5 ]

Yield	Reaction Conditions	Operation in experiment
	With trichlorophosphate;aluminum (III) chloride; at 25 - 75℃; for 6.0h;Product distribution / selectivity;	Example 1; Synthesis of tris(chloropropyl) phosphate (TCPP)The reactor (FIG. 2) charged with tris(chloropropyl) phosphate was fed continuously with propylene oxide (52.5 ml/h) and aluminium trichloride in solution in phosphorus oxychloride (21.6 ml/h). The reaction was carried out with a pump circulation rate of 1638 ml/h. The catalyst concentration was varied, as was the reaction temperature. After a run time of 6 h, samples of the tris(chloropropyl) phosphate discharged were taken, and the product composition was analysed by gas chromatography. Table 1 shows the conversion of the reaction, measured as residual propylene oxide (GC%), and the isomer composition, both as a function of the catalyst concentration and the reaction temperature. A depiction of the propylene conversion from Table 1 in graph form can be seen in FIG. 1.

Reference： [1]Patent: US2008/227997,2008,A1 .Location in patent: Page/Page column 3

6
[ 13674-84-5 ]
[ 5536-61-8 ]
C₁₃H₂₃Cl₂O₆P [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With 4-(benzyloxycarbonyl)-2,2,6,6-tetramethylpiperidine-1-oxyl; tetramethlyammonium chloride; In N,N-dimethyl-formamide; at 100℃; for 36.0h;	General procedure: A 2000 ml four-necked flask was equipped with a Three-one motor and Teflon stirring blades,TMCPP (tris (beta-chloropropyl) phosphate)600 g (1.832 mol),DMF 600 g, as a polymerization inhibitor0.0102 g of BTOX (4-benzoyloxy-2,2,6,6-tetramethylpiperidine-N-oxyl)Sodium methacrylate 14.85 g (0.137 mol)And the mixture was stirred, dipped in an oil bath and heating was started.For prevention of polymerization, the reaction was carried out while supplying air at an amount of 50 ml / h into the kettle. Four hours after the internal temperature reached 100 C.,After 8 hours and 12 hours, 14.85 g (0.137 mol) of sodium methacrylate was added additionally. The total input amount of sodium methacrylate was 59.4 g (0.546 mol). Heating was stopped after 16 hours, after the internal temperature was sufficiently cooled, it was transferred to a 2000 ml separating funnel, 253 g of toluene and 759 g of pure water were added and the liquid separation operation was carried out.After standing for about 10 minutes, the upper layer (aqueous layer) was separated. Subsequently, 749 g of 0.5% aqueous solution of sodium bicarbonate was added to 954 g of the organic layer in the lower layer, and a liquid separation operation was performed. After standing for about 10 minutes, the upper layer (aqueous layer) was separated. Subsequently, 107 g of toluene and 749 g of pure water were charged into 848 g of the organic layer in the lower layer, and a liquid separation operation was performed. After allowing to stand for about 15 minutes, the upper layer (aqueous layer) was separated, sodium sulfate was added to the toluene layer to perform a dehydration operation, toluene was removed using an evaporator and a vacuum pump,585.6 g of a light brown liquid was obtained. As a result of GC analysis,The proportion of the compound of n = 0 in the formula (1) was 76.0%The proportion of the compound with n = 1 was 20.0%The proportion of the compound with n = 2 was 1.3%Compounds with n = 3 were undetected.

Reference： [1]Patent: JP2016/196434,2016,A .Location in patent: Paragraph 0053

7
[ 13674-84-5 ]
[ 849585-22-4 ]
[ 57-55-6 ]
[ 14807-82-0 ]
[ 1611-31-0 ]
[ 513-02-0 ]
[ 16136-84-8 ]
[ 124-38-9 ]
[ 86119-84-8 ]
bis(1-hydroxypropan-2-yl) hydrogenphosphate [ No CAS ]
[ 16887-00-6 ]
[ 144-62-7 ]
hydrogen cation [ No CAS ]
[ 14265-44-2 ]
[ 67-63-0 ]
[ 10294-56-1 ]

Reference： [1]Chemosphere,2019,vol. 236

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P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
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P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
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P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
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P337 + P313	IF eye irritation persists: Get medical advice/attention.
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H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
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H204	Fire or projection hazard
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H221	Flammable gas
H222	Extremely flammable aerosol
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H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
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H281	Contains refrigerated gas; may cause cryogenic burns or injury
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Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
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H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
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H316	Causes mild skin irritation
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H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
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Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 13674-84-5 ] {[proInfo.proName]}

Quality Control of [ 13674-84-5 ]

Related Doc. of [ 13674-84-5 ]

Product Details of [ 13674-84-5 ]

Calculated chemistry of [ 13674-84-5 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 13674-84-5 ]

Application In Synthesis of [ 13674-84-5 ]

[ 13674-84-5 ] Synthesis Path-Upstream 1~4

[ 13674-84-5 ] Synthesis Path-Downstream 1~7

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry