Name: Dichlorodiphenylsilane
SKU: 80-10-4

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Basic Information

Molecular Structure:
CAS No.:	80-10-4
Name:	Dichlorodiphenylsilane
Article Data:	67

Formula:	C₁₂H₁₀Cl₂Si
Molecular Weight:	253.203
Synonyms:	Silane,dichlorodiphenyl- (8CI,9CI);Diphenyldichlorosilane;Diphenylsilicon dichloride;Diphenylsilyl dichloride;NSC 77110;TSL 8062;
EINECS:	201-251-0
Density:	1.21 g/cm³
Melting Point:	-22 °C
Boiling Point:	305 °C at 760 mmHg
Flash Point:	131.7 °C
Solubility:	decomposes in water
Appearance:	Colorless transparent liquid
Hazard Symbols:	C,T
Risk Codes:	34-24-22
Safety:	26-36/37/39-45-28A
Transport Information:	UN 1769 8/PG 2
PSA:	0.00000
LogP:	2.72060

Synthetic route

: 775-12-2
diphenylsilane

: 80-10-4
diphenylsilyl dichloride

Conditions

Conditions	Yield
With tellurium tetrachloride In benzene for 3h; Heating;	95%
With copper(l) iodide; copper dichloride In diethyl ether at 20℃; for 4h; Inert atmosphere;	94.1%
With dichloromethane; eosin y at 50℃; Temperature; Reagent/catalyst; Flow reactor; Inert atmosphere; Irradiation;	99 %Spectr.

: 24388-23-6
2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole

: 98-13-5
Phenyltrichlorosilane

A: 76-86-8
Triphenylsilyl chloride

B: 80-10-4
diphenylsilyl dichloride

Conditions

Conditions	Yield
Stage #1: 2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole With bis(tricyclohexylphosphine)nickel(II) dichloride; triethylaluminum; dimethylaluminum chloride In 1,4-dioxane; hexane; 1,3,5-trimethyl-benzene at 90℃; for 0.5h; Stage #2: Phenyltrichlorosilane In hexane; toluene; 1,3,5-trimethyl-benzene at 90℃; for 24h;	A n/a B 88%

...Expand

: 108-86-1
bromobenzene

: 80-10-4
diphenylsilyl dichloride

Conditions

Conditions	Yield
Stage #1: bromobenzene With n-butyllithium In diethyl ether; hexane Stage #2: With tetrachlorosilane In diethyl ether; hexane at 0 - 5℃;
Stage #1: bromobenzene With n-butyllithium In diethyl ether at -78℃; Stage #2: With tetrachlorosilane In diethyl ether at 0 - 20℃;

: 98-13-5
Phenyltrichlorosilane

: 108-90-7
chlorobenzene

A: 4206-75-1
phenylchlorosilane

B: 80-10-4
diphenylsilyl dichloride

Conditions

Conditions	Yield
Stage #1: Phenyltrichlorosilane With hydrogenchloride In water at 350 - 400℃; under 1500.15 Torr; for 3h; Stage #2: chlorobenzene at 350 - 480℃; under 1500.15 Torr; for 10h; Reagent/catalyst; Temperature;

...Expand

: 98-13-5
Phenyltrichlorosilane

: 108-90-7
chlorobenzene

: 80-10-4
diphenylsilyl dichloride

Conditions

Conditions	Yield
With magnesium at 185℃; for 17.5h; Inert atmosphere;	68%

: 98-13-5
Phenyltrichlorosilane

: 108-90-7
chlorobenzene

A: 76-86-8
Triphenylsilyl chloride

B: 80-10-4
diphenylsilyl dichloride

Conditions

Conditions	Yield
With magnesium at 155℃; Inert atmosphere;	A 67.2% B 31.4%

...Expand

: 1631-83-0
diphenylsilyl chloride

: 80-10-4
diphenylsilyl dichloride

Conditions

Conditions	Yield
With hexachloroethane; palladium dichloride at 20℃; for 1h;	89%
With hydrogenchloride; ether adduct of tris(pentafluorophenyl)boron In toluene at 20℃; for 150h; Schlenk technique; Inert atmosphere; Cooling with liquid nitrogen;	61 %Spectr.
With dichloromethane; eosin y at 20℃; for 4h; Reagent/catalyst; Inert atmosphere; Irradiation; Green chemistry;	99 %Spectr.

: 108-90-7
chlorobenzene

A: 98-13-5
Phenyltrichlorosilane

B: 80-10-4
diphenylsilyl dichloride

Conditions

Conditions	Yield
With silicon-copper at 400℃;
With silver; silicon at 400℃;
With iron; silicon at 550℃;
With silicon-copper at 420℃;

: 108-90-7
chlorobenzene

: 7440-21-3
silicon

A: 92-52-4
biphenyl

B: 98-13-5
Phenyltrichlorosilane

C: 80-10-4
diphenylsilyl dichloride

Conditions

Conditions	Yield
tin at 450℃; under 0.1 Torr; for 1h; Product distribution / selectivity;
tin; copper; zinc at 480℃; Product distribution / selectivity;
tin; copper at 450℃; under 0.1 Torr; for 1h; Product distribution / selectivity;

...Expand

: 108-90-7
chlorobenzene

A: 92-52-4
biphenyl

B: 98-13-5
Phenyltrichlorosilane

C: 80-10-4
diphenylsilyl dichloride

Conditions

Conditions	Yield
With silicon; tin(ll) chloride at 450 - 500℃; for 2h; Product distribution / selectivity;
With silicon; tin; copper; zinc at 450℃; Product distribution / selectivity;
With silicon; tin; zinc at 450℃; Product distribution / selectivity;
With silicon; tin at 450℃; Product distribution / selectivity;

...Expand

Raw Materials

591-51-5

98-88-4

Downstream Products

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Consensus Reports

Reported in EPA TSCA Inventory.

Standards and Recommendations

DOT Classification: 8; Label: Corrosive

Specification

The IUPAC name of this chemical is dichloro(diphenyl)silane. With the CAS registry number 80-10-4, it is also named as Benzene, 1,1'-(dichlorosilylene)bis-. The product's categories are Silicon Compounds; Organosilicon Reagents; Dichlorosilanes; Dichlorosilanes (for Polysilanes); Functional Materials; Reagent for High-Performance Polymer Research; Si-Cl Compounds; Phenyl Silanes. It is colorless transparent liquid with a pungent odor that is corrosive to metals and tissue. In addition, this chemical will burn though it may require some effort to ignite. When heated to decomposition or on contact with acid or acid fumes it emits toxic fumes of Cl^-. So the storage environment should be ventilate, low-temperature and dry.

The other characteristics of this product can be summarized as: (1)ACD/LogP: 6.69; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): 6.69; (4)ACD/LogD (pH 7.4): 6.69; (5)#H bond acceptors: 0; (6)#H bond donors: 0; (7)#Freely Rotating Bonds: 2; (8)Index of Refraction: 1.582; (9)Molar Refractivity: 69.88 cm³; (10)Molar Volume: 209.2 cm³; (11)Polarizability: 27.7×10^-24 cm³; (12)Surface Tension: 36.7 dyne/cm; (13)Enthalpy of Vaporization: 52.36 kJ/mol; (14)Boiling Point: 305 °C at 760 mmHg; (15)Vapour Pressure: 0.00152 mmHg at 25°C; (16)Rotatable Bond Count: 2; (17)Exact Mass: 251.992882; (18)MonoIsotopic Mass: 251.992882; (19)Heavy Atom Count: 15; (20)Complexity: 174.

Preparation of Dichloro diphenylsilane: The crude monomer can be obtained by chlorobenzene and silica powder in the presence of copper catalyst. Then we can get trichloro(phenyl)silane and dichloro diphenylsilane by rectification.

Uses of Dichloro diphenylsilane: It is used as raw materials of silicone oil and silicone. it is also used in the production of silicone and siloxanes and silicones, methyl phenyl. In addition, it can react with biphenyl-2,2'-diol to get 6,6-diphenyl-dibenzo[d,f][1,3,2]dioxasilepine. This reaction needs solvent benzene by heating.

When you are using this chemical, please be cautious about it as the following:
It is not only harmful if swallowed, but also toxic in contact with skin. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. After contact with skin, wash immediately with plenty of soap-suds. If you want to contact this product, you must wear suitable protective clothing, gloves and eye/face protection. In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)

People can use the following data to convert to the molecule structure.
1. SMILES:Cl[Si](Cl)(c1ccccc1)c2ccccc2
2. InChI:InChI=1/C12H10Cl2Si/c13-15(14,11-7-3-1-4-8-11)12-9-5-2-6-10-12/h1-10H

The following are the toxicity data which has been tested.

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
rabbit	LD50	skin	100uL/kg (0.1mL/kg)	BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE"	National Technical Information Service. Vol. OTS0571886,