Conditions | Yield |
---|---|
With hydrogenchloride at 20℃; | 100% |
With sodium hydroxide In water at 30℃; for 0.416667h; Concentration; Temperature; | 99.97% |
With styrene type I anion exchange resin In water at 45 - 75℃; for 2.5h; Concentration; Temperature; Inert atmosphere; | 93.8% |
Conditions | Yield |
---|---|
With hydrogenchloride In diethyl ether at 100℃; for 101.5h; | A 84% B 16% |
With hydrogenchloride; diethyl ether In benzene-d6 at 100℃; Reagent/catalyst; Schlenk technique; Inert atmosphere; | A 84 %Spectr. B 16 %Spectr. |
chloro-trimethyl-silane
bis(2-chloroethyl) vinylphosphonate
A
Hexamethyldisiloxane
B
vinylphosphonic acid
Conditions | Yield |
---|---|
Stage #1: chloro-trimethyl-silane; bis(2-chloroethyl) vinylphosphonate at 0 - 170℃; under 3040.2 Torr; for 24h; Stage #2: With water for 1 - 2h; | A n/a B 95% |
Conditions | Yield |
---|---|
With 1,1,1,3,3,3-hexamethyl-disilazane; scandium tris(trifluoromethanesulfonate) In chlorobenzene at 70℃; for 1h; | 82% |
With hydrogenchloride | |
With K2CO3 or Al2O3 In neat (no solvent) react. of (CH3)3SiOH and K2CO3 or Al2O3 at room temp.;; | |
With K2CO3 or Al2O3 In neat (no solvent) react. of (CH3)3SiOH and K2CO3 or Al2O3 at room temp.;; |
Conditions | Yield |
---|---|
With ammonium sulfate; urea In 1,2-dimethoxyethane at 90℃; for 0.666667h; Temperature; Reagent/catalyst; Inert atmosphere; Large scale; | 99.7% |
With water; hydrogenchloride at 85.4℃; Mechanism; Equilibrium constant; influence of catalyst concentration; | |
With potassium dichromate; sulfuric acid; silver sulfate In water for 2h; Mechanism; Heating; other organosilicon compounds, chemical oxygen demand value, oxidizability, glass beads presence; | |
With water; scandium tris(trifluoromethanesulfonate) In chlorobenzene at 70℃; for 1h; Inert atmosphere; |
Trimethylsilanol
phenylsilane
A
1,1,1,5,5,5-hexamethyl-3-phenyl-trisiloxane
B
Hexamethyldisiloxane
Conditions | Yield |
---|---|
With nickel(II) bis(2,2,6,6-tetramethylheptane-3,5-dionate) In dichloromethane at 20℃; for 19h; Schlenk technique; Inert atmosphere; | A 74% B 0.15 mmol |
1-(Trimethylsilyloxy)cyclohexene
A
Hexamethyldisiloxane
B
<2-D>Cyclohexanone
Conditions | Yield |
---|---|
With hydrogen; Rh(PPh3)3Cl In water-d2 at 50℃; under 760 Torr; for 18h; | A n/a B 95% |
Conditions | Yield |
---|---|
With (triphenylphosphine)gold(I) chloride; tributylphosphine In tetrahydrofuran at 25℃; for 13h; Reagent/catalyst; Solvent; Inert atmosphere; | A 15% B 85% |
Trimethylsilanol
phenylsilane
A
1,1,1,5,5,5-hexamethyl-3-phenyl-trisiloxane
B
Hexamethyldisiloxane
Conditions | Yield |
---|---|
With (triphenylphosphine)gold(I) chloride; tributylphosphine In N,N-dimethyl acetamide at 25℃; for 13h; Inert atmosphere; | A 6% B 48% C 71% |
Trimethylsilanol
2-methyl a l l y l t r i s-(trimethylsiloxy)silane
A
Hexamethyldisiloxane
B
1,1,1,5,5,5-hexamethyl-3,3-bis(trimethylsiloxy)trisiloxane
Conditions | Yield |
---|---|
With Amberlyst-15 In acetonitrile at 20℃; |
triethylsilane
chloro-trimethyl-silane
A
triethylsilyl chloride
B
Hexamethyldisiloxane
C
1,1,1-triethyl-3,3,3-trimethyl-disiloxane
Conditions | Yield |
---|---|
With Mo(CO)5(trimethylamine); N,N-dimethyl-formamide In benzene-d6 at 20℃; for 144h; Sealed tube; Inert atmosphere; |
Conditions | Yield |
---|---|
With cesium fluoride; dinitrogen monoxide In dimethylsulfoxide-d6 at 20℃; under 750.075 Torr; for 4h; Reagent/catalyst; | A 77 %Chromat. B n/a |
bis(trimethylsilyl)sulphate
Hexamethyldisiloxane
Conditions | Yield |
---|---|
With potassium sulfate at 250℃; for 3h; | 82% |
With sodium at 150℃; | 68% |
With hydrogen iodide In octane at 0℃; | 56% |
With water |
Conditions | Yield |
---|---|
With trimethylsilyl iodide In dichloromethane at 25℃; for 16h; | A n/a B 96% |
Conditions | Yield |
---|---|
With trimethylsilyl iodide In dichloromethane at 25℃; for 16h; | A n/a B 90% |
chloro-trimethyl-silane
A
1,1,1,2,2,2-hexamethyldisilane
B
Hexamethyldisiloxane
C
tris(trimethylsilyl)amine
D
1,1,1,3,3,3-hexamethyl-disilazane
Conditions | Yield |
---|---|
With sodium; cis-{tungsten(dinitrogen)2(P(methyl)2Ph)4} In tetrahydrofuran at 30℃; for 4h; Further byproducts given; | A 71.8 % Chromat. B n/a C 2.9 % Chromat. D 1.6 % Chromat. |
With sodium; cis-(molybdenum-bis(dinitrogen)(PMe2Ph)4) In tetrahydrofuran at 30℃; for 15h; Further byproducts given; | A 39.0 % Chromat. B n/a C 36.6 % Chromat. D 1.1 % Chromat. |
Conditions | Yield |
---|---|
With hydrogenchloride; diethyl ether at 120℃; for 70h; Sealed tube; | 100% |
With carbon monoxide; hydrogen; nickel at 200℃; under 750.06 Torr; for 2h; | 59% |
With bromobenzene; calcium In water for 1h; Ambient temperature; | 5% |
Conditions | Yield |
---|---|
With potassium hydroxide Heating; Yield given; | |
With calcium hydroxide; potassium hydroxide In water | |
With calcium hydroxide; potassium hydroxide In water |
Conditions | Yield |
---|---|
With trimethylsilyl iodide In dichloromethane at 25℃; for 16h; | A n/a B 93% |
Conditions | Yield |
---|---|
With trimethylsilyl iodide In dichloromethane at 25℃; for 16h; | A n/a B 98% C n/a |
chloro-trimethyl-silane
Dimethylphenylsilane
A
Hexamethyldisiloxane
B
pentamethyl(phenyl)disiloxane
C
1,1,3,3-tetramethyl-1,3-diphenyldisiloxane
D
phenyldimethylsilyl chloride
Conditions | Yield |
---|---|
With Mo(CO)5(trimethylamine); N,N-dimethyl-formamide In benzene-d6 at 20℃; for 192h; Sealed tube; Inert atmosphere; |
triethylsilane
chloro-trimethyl-silane
A
triethylsilyl chloride
B
Hexamethyldisiloxane
C
1,1,1-triethyl-3,3,3-trimethyl-disiloxane
D
hexaethyl disiloxane
Conditions | Yield |
---|---|
With Mo(CO)5(trimethylamine); N,N-dimethyl-formamide In benzene-d6 at 50℃; for 3h; Sealed tube; Inert atmosphere; |
chloro-trimethyl-silane
methyldiphenylsilane
A
Hexamethyldisiloxane
B
1,1,1,3-tetramethyl-3,3-diphenyl-disiloxane
C
chloromethyldiphenylsilane
D
1,3-Dimethyl-1,1,3,3-tetraphenyldisiloxan
Conditions | Yield |
---|---|
With Mo(CO)5(trimethylamine); N,N-dimethyl-formamide In benzene-d6 at 20℃; for 408h; Sealed tube; Inert atmosphere; |
Conditions | Yield |
---|---|
With trimethylsilyl iodide In dichloromethane at 25℃; for 16h; | A 84% B n/a C n/a |
1,3-bis(iodomethyl)-1,1,3,3-tetramethyl-disiloxane
2-Mercaptobenzothiazole
A
Hexamethyldisiloxane
Conditions | Yield |
---|---|
at 150℃; for 3h; | A n/a B 81% |
chloro-trimethyl-silane
A
1,1,1,2,2,2-hexamethyldisilane
B
Hexamethyldisiloxane
C
Me3Si(CH2)4OSiMe3
D
1,1,1,3,3,3-hexamethyl-disilazane
Conditions | Yield |
---|---|
With sodium; molybdenum(V) chloride In tetrahydrofuran at 30℃; for 4h; | A 8.6 % Chromat. B n/a C 34.6 % Chromat. D 2.0 % Chromat. |
Conditions | Yield |
---|---|
With potassium fluoride; 18-crown-6 ether In water; chlorobenzene at 90 - 100℃; for 2h; | A 41% B n/a |
1-nitrohexane
A
hexanenitrile
B
hexanal oxime
C
Hexamethyldisiloxane
Conditions | Yield |
---|---|
With trimethylsilyl iodide In dichloromethane at 25℃; for 16h; | A 10% B 81% C n/a |
Conditions | Yield |
---|---|
With trimethylsilyl iodide In dichloromethane at 25℃; for 16h; | A n/a B 71% |
C-trimethylsiloxymethyl-C,N-bis(trimethylsilyl)ketimine
A
Hexamethyldisiloxane
B
α-trimethylsilylacrylonitrile
Conditions | Yield |
---|---|
With boron trifluoride diethyl etherate In dichloromethane at -78℃; or other Lewis acids; | A n/a B 88% |
Hexamethyldisiloxane
(acetylthiomethyl)trifluorosilane
Conditions | Yield |
---|---|
In tetrachloromethane Ambient temperature; | 100% |
Hexamethyldisiloxane
mono-trimethylsilylphosphite
Conditions | Yield |
---|---|
With phosphonic Acid Heating; | 100% |
Hexamethyldisiloxane
S-(tert-butyl)-S-phenylsulfoximine
S-tert-butyl-N-trimethylsilyl-S-phenylsulfoximine
Conditions | Yield |
---|---|
at 85℃; for 0.666667h; | 100% |
Hexamethyldisiloxane
S-methyl-S-phenylsulfoximine
S-methyl-S-phenyl-N-(trimethylsilyl)sulfoximine
Conditions | Yield |
---|---|
at 85℃; for 0.666667h; | 100% |
Hexamethyldisiloxane
Conditions | Yield |
---|---|
In neat (no solvent) byproducts: CMe4; inert atm.; stirring (67°C, several h); evapn. (vac.); | 100% |
The IUPAC name of Hexamethyldisiloxane is trimethyl(trimethylsilyloxy)silane. With the CAS registry number 107-46-0 and EINECS 203-492-7, it is also named as Disiloxane, hexamethyl-. The product's categories are Siloxanes; Organics; Si (Classes of Silicon Compounds); Silicon Compounds (for Synthesis); Si-O Compounds; Synthetic Organic Chemistry. It is colorless or yellowish transparent liquid which is stable, but moisture sensitive. It is also highly flammable, so people should keep it away from sources of ignition. When heated to decomposition it emits acrid smoke and fumes. Additionally, this chemical should be sealed in the container and stored in the cool, well-ventilated and dry place.
The other characteristics of Hexamethyldisiloxane can be summarized as:
(1)ACD/LogP: 4.21; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 4.2; (4)ACD/LogD (pH 7.4): 4.2; (5)ACD/BCF (pH 5.5): 923.51; (6)ACD/BCF (pH 7.4): 923.51; (7)ACD/KOC (pH 5.5): 4615.97; (8)ACD/KOC (pH 7.4): 4615.97; (9)#H bond acceptors: 1; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 2; (12)Polar Surface Area: 9.23 Å2; (13)Index of Refraction: 1.393; (14)Molar Refractivity: 49.02 cm3; (15)Molar Volume: 205.4 cm3; (16)Polarizability: 19.43×10-24 cm3; (17)Surface Tension: 15.6 dyne/cm; (18)Enthalpy of Vaporization: 32.61 kJ/mol; (19)Vapour Pressure: 41.4 mmHg at 25°C; (20)Rotatable Bond Count: 2; (21)Exact Mass: 162.089618; (22)MonoIsotopic Mass: 162.089618; (23)Topological Polar Surface Area: 9.2; (24)Heavy Atom Count: 9; (25)Complexity: 76.2.
Preparation of Hexamethyldisiloxane:
Adding 62.49g (0.575mol) trimethylchlorosilane to the solution of 72.7g (0.06mol) N, N-dimethylaniline and 7g water and refluxing 1h. Using atmospheric distillation to collect fractions of 98-101 °C. After drying. we can get 43-44g product. The yield is 92-94%. 2(CH3)3SiCl+H2O→(CH3)3SiO(CH3)3Si+2HCl
Uses of Hexamethyldisiloxane:
It is mainly used as source of the trimethylsilyl functional group (-Si(CH3)3) in organic synthesis. It is also used in liquid bandages (spray on plasters) such as cavilon spray, to protect damaged skin from irritation from other bodily fluids. What's more, it is used as a solvent and as a reagent in organic synthesis. For example: it can react with 4-benzoylamino-1H-pyrimidin-2-one to get N-(2-oxo-1-trimethylsilanyl-1,2-dihydro-pyrimidin-4-yl)-benzamide. This reaction which is a kind of alkylation needs reagent (NH4)2SO4 and solvent acetonitrile at temperature of 140 °C. The reaction time is 20 hours. The yield is 37%.
People can use the following data to convert to the molecule structure.
1. SMILES:O([Si](C)(C)C)[Si](C)(C)C
2. InChI:InChI=1/C6H18OSi2/c1-8(2,3)7-9(4,5)6/h1-6H3
3. InChIKey:UQEAIHBTYFGYIE-UHFFFAOYAL
The following are the toxicity data of Hexamethyldisiloxane:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
guinea pig | LDLo | oral | 50gm/kg (50000mg/kg) | Journal of Industrial Hygiene and Toxicology. Vol. 30, Pg. 332, 1948. | |
mouse | LD50 | intraperitoneal | 4500mg/kg (4500mg/kg) | Russian Chemical Reviws Vol. 38, Pg. 975, 1969. | |
rabbit | LD50 | skin | 16mL/kg (16mL/kg) | PERIPHERAL NERVE AND SENSATION: FLACCID PARALYSIS WITH APPROPRIATE ANESTHESIA BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) | Acute Toxicity Data. Journal of the American College of Toxicology, Part B. Vol. 12, Pg. 590, 1993. |
rat | LC50 | inhalation | 15956ppm/4H (15956ppm) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD BEHAVIORAL: ATAXIA | National Technical Information Service. Vol. OTS0573658, |
rat | LDLo | intraperitoneal | 1825mg/kg (1825mg/kg) | National Technical Information Service. Vol. OTS0572636, | |
rat | LDLo | oral | 8mL/kg (8mL/kg) | BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) | Acute Toxicity Data. Journal of the American College of Toxicology, Part B. Vol. 12, Pg. 590, 1993. |
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