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| CAS No.: | 107-46-0 |
|---|---|
| Name: | Hexamethyldisiloxane |
| Molecular Structure: | |
|
|
|
| Formula: | C6H18OSi2 |
| Molecular Weight: | 78.218 |
| Synonyms: | hexamethyl-Disiloxane;Hexamethyldisiloxane(HMDO);Disiloxane,hexamethyl-;Disiloxane, hexamethyl-;Silane, oxybis(trimethyl-;Oxybis (trimethylsilane);Oxybis(trimethylsilane);Bis(trimethylsilyl) oxide;Bis(trimethylsilyl)oxide;OS 10 (siloxane);Bistrimethylsilyl ether;Hexamethyldisiloxane (MM);Hexamethyldisiloxane (HMDSO);Bis(trimethylsilyl) ether;trimethyl-trimethylsilyloxy-silane;Bis-trimethylsilyl oxide;Hexamethyl disiloxane;Silane, oxybis(trimethyl)-;Bis(trimethylsilyl)ether; |
| EINECS: | 203-492-7 |
| Density: | 0.79 g/cm3 |
| Melting Point: | -59 °C |
| Boiling Point: | 100.9 °C at 760 mmHg |
| Flash Point: | 7.7 °C |
| Solubility: | insoluble in water |
| Appearance: | Colorless or yellowish transparent liquid |
| Hazard Symbols: |
 F
|
| Risk Codes: | 11 |
| Safety: | 16 |
| Transport Information: | UN 1993 3/PG 2 |
| PSA: | 9.23000 |
| LogP: | 2.67280 |
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| 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. |
- 75-77-4
chloro-trimethyl-silane
- 115-98-0
bis(2-chloroethyl) vinylphosphonate
A
- 107-46-0
Hexamethyldisiloxane
B
- 1746-03-8
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; |
- 1066-40-6
Trimethylsilanol
- 694-53-1
phenylsilane
A
- 27991-58-8
1,1,1,5,5,5-hexamethyl-3-phenyl-trisiloxane
B
- 107-46-0
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 |
| 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% |
- 1066-40-6
Trimethylsilanol
- 694-53-1
phenylsilane
A
- 27991-58-8
1,1,1,5,5,5-hexamethyl-3-phenyl-trisiloxane
B
- 107-46-0
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% |
- 1066-40-6
Trimethylsilanol
- 37611-52-2
2-methyl a l l y l t r i s-(trimethylsiloxy)silane
A
- 107-46-0
Hexamethyldisiloxane
B
- 3555-47-3
1,1,1,5,5,5-hexamethyl-3,3-bis(trimethylsiloxy)trisiloxane
| Conditions | Yield |
|---|---|
| With Amberlyst-15 In acetonitrile at 20℃; |
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Consensus Reports
Specification
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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