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107-46-0

Basic Information
CAS No.: 107-46-0
Name: Hexamethyldisiloxane
Molecular Structure:
Molecular Structure of 107-46-0 (Hexamethyldisiloxane)
Formula: C6H18OSi2
Molecular Weight: 162.38
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: FlammableF
Risk Codes: 11
Safety: 16
Transport Information: UN 1993 3/PG 2
PSA: 9.23000
LogP: 2.67280
Synthetic route
75-77-4

chloro-trimethyl-silane

107-46-0

Hexamethyldisiloxane

Conditions
ConditionsYield
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%
993-07-7

trimethylsilan

A

75-77-4

chloro-trimethyl-silane

B

107-46-0

Hexamethyldisiloxane

Conditions
ConditionsYield
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
ConditionsYield
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%
1066-40-6

Trimethylsilanol

107-46-0

Hexamethyldisiloxane

Conditions
ConditionsYield
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.;;
999-97-3

1,1,1,3,3,3-hexamethyl-disilazane

107-46-0

Hexamethyldisiloxane

Conditions
ConditionsYield
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
ConditionsYield
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
6651-36-1

1-(Trimethylsilyloxy)cyclohexene

A

107-46-0

Hexamethyldisiloxane

B

2979-36-4

<2-D>Cyclohexanone

Conditions
ConditionsYield
With hydrogen; Rh(PPh3)3Cl In water-d2 at 50℃; under 760 Torr; for 18h;A n/a
B 95%
1066-40-6

Trimethylsilanol

694-53-1

phenylsilane

A

107-46-0

Hexamethyldisiloxane

B

C9H16OSi2

Conditions
ConditionsYield
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

C

C9H16OSi2

Conditions
ConditionsYield
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
ConditionsYield
With Amberlyst-15 In acetonitrile at 20℃;
617-86-7

triethylsilane

75-77-4

chloro-trimethyl-silane

A

994-30-9

triethylsilyl chloride

B

107-46-0

Hexamethyldisiloxane

C

2652-41-7

1,1,1-triethyl-3,3,3-trimethyl-disiloxane

Conditions
ConditionsYield
With Mo(CO)5(trimethylamine); N,N-dimethyl-formamide In benzene-d6 at 20℃; for 144h; Sealed tube; Inert atmosphere;
1450-14-2

1,1,1,2,2,2-hexamethyldisilane

A

107-46-0

Hexamethyldisiloxane

B

7727-37-9

nitrogen

Conditions
ConditionsYield
With cesium fluoride; dinitrogen monoxide In dimethylsulfoxide-d6 at 20℃; under 750.075 Torr; for 4h; Reagent/catalyst;A 77 %Chromat.
B n/a
18306-29-1

bis(trimethylsilyl)sulphate

107-46-0

Hexamethyldisiloxane

Conditions
ConditionsYield
With potassium sulfate at 250℃; for 3h;82%
With sodium at 150℃;68%
With hydrogen iodide In octane at 0℃;56%
With water
1-nitro-1-phenylmethane

1-nitro-1-phenylmethane

A

107-46-0

Hexamethyldisiloxane

B

Conditions
ConditionsYield
With trimethylsilyl iodide In dichloromethane at 25℃; for 16h;A n/a
B 96%
1-methyl-2-(2-nitroethyl)benzene

1-methyl-2-(2-nitroethyl)benzene

A

107-46-0

Hexamethyldisiloxane

B

529-19-1

2-Methylbenzonitrile

Conditions
ConditionsYield
With trimethylsilyl iodide In dichloromethane at 25℃; for 16h;A n/a
B 90%
75-77-4

chloro-trimethyl-silane

A

1450-14-2

1,1,1,2,2,2-hexamethyldisilane

B

107-46-0

Hexamethyldisiloxane

C

1586-73-8

tris(trimethylsilyl)amine

D

999-97-3

1,1,1,3,3,3-hexamethyl-disilazane

Conditions
ConditionsYield
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.
1450-14-2

1,1,1,2,2,2-hexamethyldisilane

107-46-0

Hexamethyldisiloxane

Conditions
ConditionsYield
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%
420-56-4

trimethylsilyl fluoride

107-46-0

Hexamethyldisiloxane

Conditions
ConditionsYield
With potassium hydroxide Heating; Yield given;
With calcium hydroxide; potassium hydroxide In water
With calcium hydroxide; potassium hydroxide In water
38362-90-2

3-nitroxylene

A

107-46-0

Hexamethyldisiloxane

B

620-22-4

3-Methylbenzonitrile

Conditions
ConditionsYield
With trimethylsilyl iodide In dichloromethane at 25℃; for 16h;A n/a
B 93%
7575-82-8

1-nitroadamantane

A

107-46-0

Hexamethyldisiloxane

B

768-93-4

1-iodoadamantane

C

NO, 0.5I2

NO, 0.5I2

Conditions
ConditionsYield
With trimethylsilyl iodide In dichloromethane at 25℃; for 16h;A n/a
B 98%
C n/a
75-77-4

chloro-trimethyl-silane

766-77-8

Dimethylphenylsilane

A

107-46-0

Hexamethyldisiloxane

B

14920-92-4

pentamethyl(phenyl)disiloxane

C

56-33-7

1,1,3,3-tetramethyl-1,3-diphenyldisiloxane

D

768-33-2

phenyldimethylsilyl chloride

Conditions
ConditionsYield
With Mo(CO)5(trimethylamine); N,N-dimethyl-formamide In benzene-d6 at 20℃; for 192h; Sealed tube; Inert atmosphere;
617-86-7

triethylsilane

75-77-4

chloro-trimethyl-silane

A

994-30-9

triethylsilyl chloride

B

107-46-0

Hexamethyldisiloxane

C

2652-41-7

1,1,1-triethyl-3,3,3-trimethyl-disiloxane

D

994-49-0

hexaethyl disiloxane

Conditions
ConditionsYield
With Mo(CO)5(trimethylamine); N,N-dimethyl-formamide In benzene-d6 at 50℃; for 3h; Sealed tube; Inert atmosphere;
75-77-4

chloro-trimethyl-silane

776-76-1

methyldiphenylsilane

A

107-46-0

Hexamethyldisiloxane

B

1719-04-6

1,1,1,3-tetramethyl-3,3-diphenyl-disiloxane

C

144-79-6

chloromethyldiphenylsilane

D

807-28-3

1,3-Dimethyl-1,1,3,3-tetraphenyldisiloxan

Conditions
ConditionsYield
With Mo(CO)5(trimethylamine); N,N-dimethyl-formamide In benzene-d6 at 20℃; for 408h; Sealed tube; Inert atmosphere;
1122-60-7

1-nitrocyclohexane

A

100-64-1

Cyclohexanone oxime

B

107-46-0

Hexamethyldisiloxane

C

I2

I2

Conditions
ConditionsYield
With trimethylsilyl iodide In dichloromethane at 25℃; for 16h;A 84%
B n/a
C n/a
2943-69-3

1,3-bis(iodomethyl)-1,1,3,3-tetramethyl-disiloxane

149-30-4

2-Mercaptobenzothiazole

A

107-46-0

Hexamethyldisiloxane

B

2-[({3-[(1,3-benzotiazolium-2-ylsulfanyl)methyl]-1,1,3,3-tetramethyldisiloxanyl}methyl)sulfanyl]-1,3-benzotiazolium diiodide

Conditions
ConditionsYield
at 150℃; for 3h;A n/a
B 81%

75-77-4

chloro-trimethyl-silane

A

1450-14-2

1,1,1,2,2,2-hexamethyldisilane

B

107-46-0

Hexamethyldisiloxane

C

7140-91-2

Me3Si(CH2)4OSiMe3

D

999-97-3

1,1,1,3,3,3-hexamethyl-disilazane

Conditions
ConditionsYield
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.
75-77-4

chloro-trimethyl-silane

A

420-56-4

trimethylsilyl fluoride

B

107-46-0

Hexamethyldisiloxane

Conditions
ConditionsYield
With potassium fluoride; 18-crown-6 ether In water; chlorobenzene at 90 - 100℃; for 2h;A 41%
B n/a
646-14-0

1-nitrohexane

A

628-73-9

hexanenitrile

B

6033-61-0

hexanal oxime

C

107-46-0

Hexamethyldisiloxane

Conditions
ConditionsYield
With trimethylsilyl iodide In dichloromethane at 25℃; for 16h;A 10%
B 81%
C n/a
102-96-5

(2-nitroethenyl)benzene

A

107-46-0

Hexamethyldisiloxane

B

140-29-4

phenylacetonitrile

Conditions
ConditionsYield
With trimethylsilyl iodide In dichloromethane at 25℃; for 16h;A n/a
B 71%
104724-76-7

C-trimethylsiloxymethyl-C,N-bis(trimethylsilyl)ketimine

A

107-46-0

Hexamethyldisiloxane

B

96475-89-7

α-trimethylsilylacrylonitrile

Conditions
ConditionsYield
With boron trifluoride diethyl etherate In dichloromethane at -78℃; or other Lewis acids;A n/a
B 88%
107-46-0

Hexamethyldisiloxane

91258-92-3

(acetylthiomethyl)trifluorosilane

acetylthiomethyl(trimethylsiloxy)difluorosilane

Conditions
ConditionsYield
In tetrachloromethane Ambient temperature;100%
107-46-0

Hexamethyldisiloxane

91076-68-5

mono-trimethylsilylphosphite

Conditions
ConditionsYield
With phosphonic Acid Heating;100%
107-46-0

Hexamethyldisiloxane

222306-90-3

S-(tert-butyl)-S-phenylsulfoximine

222306-91-4

S-tert-butyl-N-trimethylsilyl-S-phenylsulfoximine

Conditions
ConditionsYield
at 85℃; for 0.666667h;100%
107-46-0

Hexamethyldisiloxane

4381-25-3

S-methyl-S-phenylsulfoximine

89902-44-3

S-methyl-S-phenyl-N-(trimethylsilyl)sulfoximine

Conditions
ConditionsYield
at 85℃; for 0.666667h;100%
107-46-0

Hexamethyldisiloxane

[trans-C5H8(PCy2)2Pt(CH2CMe3)H]

[trans-C5H8(PCy2)2Pt(CH2CMe3)CH2SiMe2OSiMe3]

Conditions
ConditionsYield
In neat (no solvent) byproducts: CMe4; inert atm.; stirring (67°C, several h); evapn. (vac.);100%
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Reported in EPA TSCA Inventory.

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%.
Hexamethyldisiloxane can react with 4-benzoylamino-1H-pyrimidin-2-one to get N-(2-oxo-1-trimethylsilanyl-1,2-dihydro-pyrimidin-4-yl)-benzamide

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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