Product Name

  • Name

    Triethylenethiophosphoramide

  • EINECS 200-135-7
  • CAS No. 52-24-4
  • Article Data10
  • CAS DataBase
  • Density 1.5 g/cm3
  • Solubility water: 19 g/100 mL (25 °C)
  • Melting Point 54-57 °C
  • Formula C6H12N3PS
  • Boiling Point 270.2 °C at 760 mmHg
  • Molecular Weight 189.221
  • Flash Point 117.2 °C
  • Transport Information UN 2811 6.1/PG 2
  • Appearance white crystals or powder
  • Safety 53-22-26-36/37/39-45-36/37-28
  • Risk Codes 45-46-28
  • Molecular Structure Molecular Structure of 52-24-4 (Triethylenethiophosphoramide)
  • Hazard Symbols VeryT+
  • Synonyms Phosphinesulfide, tris(1-aziridinyl)- (7CI,8CI);1,1',1''-Phosphinothioylidynetrisaziridine;AI 3-24916;CBC 806495;Girostan;N,N',N''-Triethylenethiophosphoramide;N,N',N''-Triethylenethiophosphortriamide;NCI C01649;NSC 6396;Oncotepa;Oncothio-tepa;Oncotiotepa;Phosphorothioic acid triethylenetriamide;Phosphorothioic triamide, N,N',N''-tri-1,2-ethanediyl-;SK 6882;STEPA;TESPA;TSPA;Tespamin;Tespamine;Thio-Tep;Thio-Tepa S;Thiofozil;Thiophosphamide;Thiophosphoramide, N,N',N''-tri-1,2-ethanediyl-;Thioplex;Thiotef;Thiotepa;Tio-TEF;Tiofosfamid;Tiofosyl;Tiofozil;Triethylenethiophosphoramide;Tris(1-aziridinyl)phosphine sulfide;
  • PSA 50.93000
  • LogP 0.62200

Synthetic route

ethyleneimine
151-56-4

ethyleneimine

Thiotepa
52-24-4

Thiotepa

Conditions
ConditionsYield
With trichlorothiophosphine at 16.5℃; for 0.533333h; Temperature;90.7%
With trichlorothiophosphine; triethylamine; benzene
Thiotepa
52-24-4

Thiotepa

N,N',N''-tris(β-mercaptoethyl)triamidothiophosphate
13884-58-7

N,N',N''-tris(β-mercaptoethyl)triamidothiophosphate

Conditions
ConditionsYield
With hydrogenchloride; lithium thiophosphate powder In water; N,N-dimethyl-formamide at 25℃;94%
Thiotepa
52-24-4

Thiotepa

C6H15N3O9P4S4(6-)*6Li(1+)
83822-75-7

C6H15N3O9P4S4(6-)*6Li(1+)

Conditions
ConditionsYield
With hydrogenchloride; lithium thiophosphate powder In water for 0.333333h; Ambient temperature;94%
5-nitrobarbituric acid
611-08-5

5-nitrobarbituric acid

Thiotepa
52-24-4

Thiotepa

N,N',N''-Tris<β-(5-nitro-3-uracil)ethyl>thiophosphoric acid triamide
84295-07-8

N,N',N''-Tris<β-(5-nitro-3-uracil)ethyl>thiophosphoric acid triamide

Conditions
ConditionsYield
In water at 37℃; for 288h;74.2%
Thiotepa
52-24-4

Thiotepa

acetoneberberine
39024-13-0

acetoneberberine

N',N'',N'''-Tri-<2-(N-Acetonylberberinyl)ethylamide> of thiophosphoric acid
70519-25-4

N',N'',N'''-Tri-<2-(N-Acetonylberberinyl)ethylamide> of thiophosphoric acid

Conditions
ConditionsYield
In methanol for 15h; Heating;72.4%
Thiotepa
52-24-4

Thiotepa

7,8-dihydroberberine
483-15-8

7,8-dihydroberberine

N',N'',N'''-Tri-(N-dihydroberberinylethylamide) of thiophosphoric acid
70519-22-1

N',N'',N'''-Tri-(N-dihydroberberinylethylamide) of thiophosphoric acid

Conditions
ConditionsYield
In methanol for 15h; Heating;69%
Thiotepa
52-24-4

Thiotepa

uracil
66-22-8

uracil

N,N',N''-Tris<β-(3-uracil)ethyl>thiophosphoric acid triamide trisodium salt
84295-06-7

N,N',N''-Tris<β-(3-uracil)ethyl>thiophosphoric acid triamide trisodium salt

Conditions
ConditionsYield
With sodium hydroxide at 37℃; for 168h;64.7%
Thiotepa
52-24-4

Thiotepa

acetoneberberine
39024-13-0

acetoneberberine

N',N''-Di-<2-N-(Acetonylberberinyl)ethylamide> of aziridinylthiophosphoric acid
70519-24-3

N',N''-Di-<2-N-(Acetonylberberinyl)ethylamide> of aziridinylthiophosphoric acid

Conditions
ConditionsYield
In acetone for 3h; Heating;59.5%
Thiotepa
52-24-4

Thiotepa

oxyberberine
549-21-3

oxyberberine

N',N'',N'''-Tri-(N-hydroxyberberinylethylamide) of thiophosphoric acid
79788-30-0

N',N'',N'''-Tri-(N-hydroxyberberinylethylamide) of thiophosphoric acid

Conditions
ConditionsYield
In methanol Heating;55%
Thiotepa
52-24-4

Thiotepa

acetoneberberine
39024-13-0

acetoneberberine

N'-<2-(N-Acetonylberberinyl)ethylamide> of diaziridinylthiophosphoric acid
70519-23-2

N'-<2-(N-Acetonylberberinyl)ethylamide> of diaziridinylthiophosphoric acid

Conditions
ConditionsYield
In 1,4-dioxane for 1h; Heating;51%
6-Methyluracil
626-48-2

6-Methyluracil

Thiotepa
52-24-4

Thiotepa

N,N',N''-Tris<β-(6-methyl-3-uracil)ethyl>thiophosphoric acid triamide trisodium salt
84295-08-9

N,N',N''-Tris<β-(6-methyl-3-uracil)ethyl>thiophosphoric acid triamide trisodium salt

Conditions
ConditionsYield
With sodium hydroxide at 37℃; for 168h;42.9%
picoline
108-89-4

picoline

Thiotepa
52-24-4

Thiotepa

P,P-bis(1-aziridinyl)-N-<2-(4-methylpyridinio)ethyl>phosphinimidothioate

P,P-bis(1-aziridinyl)-N-<2-(4-methylpyridinio)ethyl>phosphinimidothioate

Conditions
ConditionsYield
In diethyl ether for 3h; Heating;40.3%
pyridine
110-86-1

pyridine

Thiotepa
52-24-4

Thiotepa

P,P-bis(1-aziridinyl)-N-(2-pyridinioethyl)phosphinimidothioate

P,P-bis(1-aziridinyl)-N-(2-pyridinioethyl)phosphinimidothioate

Conditions
ConditionsYield
In diethyl ether for 3h; Heating;15.5%
Thiotepa
52-24-4

Thiotepa

C6H15Br3N3PS
57900-25-1

C6H15Br3N3PS

Conditions
ConditionsYield
With hydrogen bromide In benzene
Thiotepa
52-24-4

Thiotepa

A

N,N',N''-triethylenephosphoramide
545-55-1

N,N',N''-triethylenephosphoramide

B

C6H15Cl3N3OP
27780-83-2

C6H15Cl3N3OP

C

C6H15Cl3N3PS
93598-04-0

C6H15Cl3N3PS

D

C6H13ClN3OP
118694-55-6

C6H13ClN3OP

E

C6H13ClN3PS
90877-51-3

C6H13ClN3PS

F

C6H14Cl2N3PS
93598-03-9

C6H14Cl2N3PS

Conditions
ConditionsYield
In hydrogenchloride at 37℃; for 1h; Product distribution; different concentration of acid;
...Expand
Thiotepa
52-24-4

Thiotepa

C6H14N3OPS
121258-29-5

C6H14N3OPS

Conditions
ConditionsYield
With water at 37℃; change in the percentage of E/G (ethyleneimino groups) with time;
Thiotepa
52-24-4

Thiotepa

C6H13ClN3PS
90877-51-3

C6H13ClN3PS

Conditions
ConditionsYield
With sodium chloride at 37℃; effect of NaCl on the rate of hydrolysis; also in the presence of HCl instead of NaCl;
Thiotepa
52-24-4

Thiotepa

A

C6H13ClN3PS
90877-51-3

C6H13ClN3PS

B

C6H14Cl2N3PS
93598-03-9

C6H14Cl2N3PS

Conditions
ConditionsYield
With hydrogenchloride for 1h; Product distribution; or 37 deg C for definite times;
Thiotepa
52-24-4

Thiotepa

Chloride of thiophosphoric acid N'-<(N-acetonylberberinyl)ethylamide>-N'',N'''-di-(2-chloroethyl)diamide
79788-33-3

Chloride of thiophosphoric acid N'-<(N-acetonylberberinyl)ethylamide>-N'',N'''-di-(2-chloroethyl)diamide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 51 percent / dioxane / 1 h / Heating
2: 67.4 percent / HCl / CHCl3; benzene / 1 h / -10 - -7 °C
View Scheme
Chelidonium majus L.; alkaloids extract of

Chelidonium majus L.; alkaloids extract of

Thiotepa
52-24-4

Thiotepa

Chelidonium majus L.; alkaloids extract of; methylated by thiotepa

Chelidonium majus L.; alkaloids extract of; methylated by thiotepa

Conditions
ConditionsYield
Stage #1: Chelidonium majus L.; alkaloids extract of; Thiotepa In dichloromethane at 80℃; for 2h; Heating / reflux;
Stage #2: With hydrogenchloride In water Conversion of starting material;
Thiotepa
52-24-4

Thiotepa

(-)-11-hydroxy-5-methyl-2,3:7,8-bis(methylenedioxy)-4b,5,6,10b,11,12-hexahydrobenzo[c]phenanthridine
88200-01-5

(-)-11-hydroxy-5-methyl-2,3:7,8-bis(methylenedioxy)-4b,5,6,10b,11,12-hexahydrobenzo[c]phenanthridine

U-KRS

U-KRS

Conditions
ConditionsYield
Stage #1: Thiotepa; (-)-11-hydroxy-5-methyl-2,3:7,8-bis(methylenedioxy)-4b,5,6,10b,11,12-hexahydrobenzo[c]phenanthridine In dichloromethane at 80℃; for 2h; Heating / reflux;
Stage #2: With hydrogenchloride In water Conversion of starting material;

Triethylenethiophosphoramide Chemical Properties

IUPAC Name:IUPAC: Tris(aziridin-1-yl)-sulfanylidene-λ5-phosphane (52-24-4)
Synonyms: Triaziridinylphosphinesulfide ; Triethylenethiophosphorotriamide ; Tris(1-aziridinyl)-phosphinesulfid;tris(1-aziridinyl)phosphinesulphide ; Tris(ethylenimino)thiophosphate ; Wr-45312 ; Triethylenethiophosphoramide, 98+% ; Tris(aziridinyl)phosphinesulphide
CAS: 52-24-4
MF: C6H12N3PS
MW: 189.22
EINECS: 200-135-7
MS: 
Mol File: 52-24-4.mol
Surface Tension: 77.7 dyne/cm 
Density: 1.5 g/cm3 
Flash Point: 117.2 °C 
Enthalpy of Vaporization: 50.83 kJ/mol 
Boiling Point: 270.2 °C at 760 mmHg 
Vapour Pressure: 0.00695 mmHg at 25°C
Melting point:  54-57 °C 
Storage temp:  2-8°C
Appearance: solid
Water Solubility:  19 g/100 mL (25 ºC)
Stability: Stable. Incompatible with strong oxidizing agents.

Triethylenethiophosphoramide Toxicity Data With Reference

Organism

Test Type

Route

Reported Dose (Normalized Dose)

Effect

Source

bird - wild

LD50

oral

5620ug/kg (5.62mg/kg)

 

Archives of Environmental Contamination and Toxicology. Vol. 12, Pg. 355, 1983.

dog

LDLo

intravenous

760ug/kg (0.76mg/kg)

blood: leukopenia
blood: agranulocytosis
blood: other changes

Cancer Chemotherapy Reports, Part 2. Vol. 2, Pg. 203, 1965.

man

TDLo

parenteral

631ug/kg (0.631mg/kg)

peripheral nerve and sensation: paresthesis
blood: changes in bone marrow not included above

Cancer Vol. 38, Pg. 1471, 1976.

monkey

LDLo

intravenous

1500ug/kg (1.5mg/kg)

blood: leukopenia
blood: agranulocytosis
blood: other changes

Cancer Chemotherapy Reports, Part 2. Vol. 2, Pg. 203, 1965.

mouse

LD50

intramuscular

11500ug/kg (11.5mg/kg)

 

Pharmaceutical Chemistry Journal Vol. 17, Pg. 353, 1983.

mouse

LD50

intraperitoneal

11mg/kg (11mg/kg)

 

Fiziologicheski Aktivnye Veshchestva. Physiologically Active Substances. Vol. 22, Pg. 36, 1990.

mouse

LD50

intravenous

14500ug/kg (14.5mg/kg)

 

Journal of Antibiotics, Series A. Vol. 13, Pg. 19, 1960.

mouse

LD50

oral

38mg/kg (38mg/kg)

peripheral nerve and sensation: flaccid paralysis without anesthesia (usually neuromuscular blockage)
behavioral: ataxia
behavioral: somnolence (general depressed activity)

"Imifos," Giller, S.A., ed., Izd, Riga, USSR, 1968Vol. -, Pg. 129, 1968.

mouse

LD50

subcutaneous

16500ug/kg (16.5mg/kg)

liver: "hepatitis (hepatocellular necrosis), zonal"
blood: changes in spleen
kidney, ureter, and bladder: "changes in tubules (including acute renal failure, acute tubular necrosis)"

Farmakologiya i Toksikologiya Vol. 8, Pg. 73, 1973.

quail

LD50

oral

237mg/kg (237mg/kg)

 

Ecotoxicology and Environmental Safety. Vol. 6, Pg. 149, 1982.

rabbit

LD50

intravenous

5500ug/kg (5.5mg/kg)

liver: "hepatitis (hepatocellular necrosis), zonal"
kidney, ureter, and bladder: "changes in tubules (including acute renal failure, acute tubular necrosis)"
blood: changes in spleen

Farmakologiya i Toksikologiya Vol. 8, Pg. 73, 1973.

rat

LD50

intraarterial

8750ug/kg (8.75mg/kg)

 

Toxicology and Applied Pharmacology. Vol. 4, Pg. 344, 1962.

rat

LD50

intraperitoneal

8mg/kg (8mg/kg)

 

Clinical Proceedings of the Children's Hospital of the District of Columbia. Vol. 18, Pg. 307, 1962.

rat

LD50

intravenous

9400ug/kg (9.4mg/kg)

 

Arzneimittel-Forschung. Drug Research. Vol. 8, Pg. 1, 1958.

rat

LD50

oral

23mg/kg (23mg/kg)

 

Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 9, Pg. 759, 1967.

rat

LD50

subcutaneous

7800ug/kg (7.8mg/kg)

 

Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 9, Pg. 759,

Triethylenethiophosphoramide Safety Profile

Hazard Codes : T+
Risk Statements:  45-46-28
28:  Thiotriethylenephosphoramide (52-24-4) is Very Toxic if swallowed
45:  May cause cancer 
46: Thiotriethylenephosphoramide (52-24-4) may cause heritable genetic damage
Safety Statements:  53-22-26-36/37/39-45-28
22:  Do not breathe dust
26:  In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
28:  After contact with skin, wash immediately with plenty of ... (to be specified by the manufacturer)
45:  In case of accident or if you feel unwell, seek medical advice immediately (show label where possible)
53:  Avoid exposure - obtain special instruction before use
36/37/39:  Wear suitable protective clothing, gloves and eye/face protection
RIDADR:  UN 2811 6.1/PG 2
WGK Germany:  3
RTECS:  SZ2975000
HazardClass:  6.1(a)
PackingGroup:  II

Triethylenethiophosphoramide Specification

1.Chemical Properties:Thiotriethylenephosphoramide (52-24-4) is white crystals or powder
2.General Description: Odorless white crystalline solid.
3.Air & Water Reactions :Water soluble.
4.Reactivity Profile :Triethylenethiophosphoramide polymerizes readily upon exposure to heat or moisture, especially at acidic pH.
5.Fire Hazard :Flash point data for Triethylenethiophosphoramide are not available. 6.Triethylenethiophosphoramide is probably combustible.
 

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