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10497-05-9

10497-05-9 Structure

10497-05-9 Structure
IdentificationMore
[Name]

TRIS(TRIMETHYLSILYL) PHOSPHATE
[CAS]

10497-05-9
[Synonyms]

PHOSPHORIC ACID TRIS(TRIMETHYLSILYL) ESTER
TIMTEC-BB SBB001292
TRIS(TRIMETHYLSILYL) PHOSPHATE
ester
Phosphoric acid, TMS
Phosphoric acid, tristrimethylsilyl
Phosphoric acid, triTMS
Silanol, trimethyl-, phosphate (3:1)
Silanol,trimethyl-,phosphate(3:1)
trimethyl-silanophosphate(3:1)
Tris-(trimethylsilyl)fosfat
Phosphoricacidtrimethylsilylester
[EINECS(EC#)]

234-028-1
[Molecular Formula]

C9H27O4PSi3
[MDL Number]

MFCD00008267
[Molecular Weight]

314.54
[MOL File]

10497-05-9.mol
Chemical PropertiesBack Directory
[Melting point ]

3-4 °C (lit.)
[Boiling point ]

228-229 °C/720 mmHg (lit.)
[density ]

0.945 g/mL at 25 °C(lit.)
[vapor pressure ]

23.3hPa at 20℃
[refractive index ]

n20/D 1.409(lit.)
[Fp ]

76 °F
[storage temp. ]

Inert atmosphere,2-8°C
[form ]

liquid
[pka]

23-25(at 25℃)
[color ]

Colorless to Light yellow to Light orange
[Specific Gravity]

0.959
[Water Solubility ]

935.5μg/L at 20℃
[Hydrolytic Sensitivity]

8: reacts rapidly with moisture, water, protic solvents
[BRN ]

1794624
[InChI]

1S/C9H27O4PSi3/c1-15(2,3)11-14(10,12-16(4,5)6)13-17(7,8)9/h1-9H3
[InChIKey]

QJMMCGKXBZVAEI-UHFFFAOYSA-N
[SMILES]

C[Si](C)(C)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C
[LogP]

4.72 at 20℃
[CAS DataBase Reference]

10497-05-9(CAS DataBase Reference)
[EPA Substance Registry System]

Silanol, trimethyl-, phosphate (3:1) (10497-05-9)
Safety DataBack Directory
[Symbol(GHS) ]

Flame (GHS02)Exclamation Mark (GHS07)
GHS02,GHS07
[Signal word ]

Danger
[Hazard statements ]

H225-H315-H319-H335
[Precautionary statements ]

P210-P302+P352-P305+P351+P338
[Hazard Codes ]

F,Xi
[Risk Statements ]

R11:Highly Flammable.
R36/37/38:Irritating to eyes, respiratory system and skin .
[Safety Statements ]

S16:Keep away from sources of ignition-No smoking .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing .
[RIDADR ]

UN 1993 3/PG 2
[WGK Germany ]

2
[RTECS ]

TC9700000
[F ]

10-21
[TSCA ]

Yes
[HS Code ]

2931.90.9010
[REACH Registrations]

Active
[HazardClass ]

3.2
[PackingGroup ]

III
[Storage Class]

3 - Flammable liquids
[Hazard Classifications]

Eye Irrit. 2
Flam. Liq. 2
Skin Irrit. 2
STOT SE 3
Hazard InformationBack Directory
[Chemical Properties]

Colorless liquid
[Uses]

Tris(trimethylsilyl) phosphite (TMSPi) is a film-forming additive for high voltage cathode material in lithium-ion batteries. Tris (trimethylsilyl) phosphate is cleaved by alkali-metal fluorides, nitrates, and acetates at give the trimethylsilyl esters of the corresponding acids.
[Definition]

ChEBI: Tris(trimethylsilyl) phosphate is an organosilicon compound that is phosphoric acid in which the three hydroxy groups are substituted by (trimethylsilyl)oxy groups. It is a phosphoric acid derivative and an organosilicon compound.
[Preparation]

Tris(trimethylsilyl)phosphine is prepared by treating trimethylsilyl chloride, white phosphorus, and sodium-potassium alloy:
1/4 P4 + 3 Me3SiCl + 3 K → P(SiMe3)3 + 3 KCl
[General Description]

Tris(trimethylsilyl) phosphate has been investigated as a novel film-forming additive for LiNi0.5Co0.2Mn0.3O2 cycling at high cut-off potential in LiPF6-based electrolyte. Tris(trimethylsilyl) phosphate [Tris(trimethylsilyl) ester of phosphoric acid] undergoes dealkylsilylation reaction with alumazene to yield heteroadamantane molecule.
[Reactivity Profile]

Tris(trimethylsilyl)phosphine and its more reactive derivative lithium bis-(trimethylsilyl)phosphide·2tetrahydrofuran are very useful reagents for the preparation of compounds with a single or a multiple element phosphorus bond. They react readily with various element halides, with carboxylic acid chlorides, and with carboxylic esters, as well as with other organic electrophiles via a substitution of lithium and/or a cleavage of the weak polar Si-P bonds.
[Flammability and Explosibility]

Notclassified
[Synthesis]

Chlorotrimethylsilane

75-77-4

Tris(trimethylsilyl)phosphate

10497-05-9

General procedure for the synthesis of tris(trimethylsilyl)phosphorus from trimethylchlorosilane: In a 1000 ml three-necked flask equipped with a thermometer and a reflux condenser, 352 g (3.24 mol) of trimethylchlorosilane and 115 g (1 mol) of ammonium dihydrogen phosphate were added. The reaction mixture was heated to 78 °C under stirring conditions and maintained for 3 hours. After completion of the reaction, the reaction mixture was filtered and the resulting filtrate was the crude product of tris(trimethylsilyl) phosphate. Subsequently, the crude product was subjected to vacuum distillation and the fraction at 125-128 °C/30 mmHg was collected to obtain 282 g of tris(trimethylsilyl) phosphate in 89.6% yield. Throughout the reaction, an exhaust gas absorption unit needs to be connected to the outlet of the reflux condenser to absorb the hydrogen chloride gas generated in the reaction with water.

[References]

[1] Inorganic Chemistry, 2018, vol. 57, # 15, p. 9348 - 9353
[2] Patent: CN105949233, 2016, A. Location in patent: Paragraph 0018; 0019; 0021; 0023; 0025; 0027; 0029
[3] Zhurnal Obshchei Khimii, 1957, vol. 27, p. 1476,1479, 1480; engl.Ausg.S. 1550, 1553
[4] Journal of Organometallic Chemistry, 2014, vol. 749, p. 197 - 203
[5] Inorganic Chemistry, 2017, vol. 56, # 17, p. 10699 - 10705
Spectrum DetailBack Directory
[Spectrum Detail]

Tris(trimethylsilyl)phosphate(10497-05-9)MS
Tris(trimethylsilyl)phosphate(10497-05-9)1HNMR
Tris(trimethylsilyl)phosphate(10497-05-9)13CNMR
Tris(trimethylsilyl)phosphate(10497-05-9)IR1
Tris(trimethylsilyl)phosphate(10497-05-9)Raman
Well-known Reagent Company Product InformationBack Directory
[Sigma Aldrich]

10497-05-9(sigmaaldrich)
[TCI AMERICA]

Tris(trimethylsilyl) Phosphate,>98.0%(GC)(10497-05-9)
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