| Identification | More | [Name]
1,2-Bis(dimethylsilyl)benzene | [CAS]
17985-72-7 | [Synonyms]
1,2-BIS(DIMETHYLSILYL)BENZENE
1,2-PHENYLENEBIS(DIMETHYLSILANE)
O-PHENYLEN-BIS-(DIMETHYLSILAN)
Silane, 1,2-phenylenebisdimethyl-
o-phenylenebis(dimethylsilane)
1,2-BIS(DIMETHYLSILYL)BENZENE 98% | [Molecular Formula]
C10H18Si2 | [MDL Number]
MFCD00142462 | [Molecular Weight]
194.42 | [MOL File]
17985-72-7.mol |
| Chemical Properties | Back Directory | [Appearance]
clear colorless liquid | [Melting point ]
<25°C | [Boiling point ]
101 °C13 mm Hg(lit.) | [density ]
0.898 g/mL at 25 °C(lit.)
| [refractive index ]
n20/D 1.51(lit.)
| [Fp ]
158 °F
| [storage temp. ]
Inert atmosphere,Room Temperature | [form ]
Liquid | [color ]
Colorless to Light yellow | [Specific Gravity]
0.898 | [Water Solubility ]
insoluble | [Hydrolytic Sensitivity]
3: reacts with aqueous base | [BRN ]
2937027 | [InChI]
InChI=1S/C10H18Si2/c1-11(2)9-7-5-6-8-10(9)12(3)4/h5-8,11-12H,1-4H3 | [InChIKey]
QAUCEYVYCBYVDK-UHFFFAOYSA-N | [SMILES]
C1([SiH](C)C)=CC=CC=C1[SiH](C)C | [CAS DataBase Reference]
17985-72-7(CAS DataBase Reference) |
| Safety Data | Back Directory | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S23:Do not breathe gas/fumes/vapor/spray (appropriate wording to be specified by the manufacturer) .
S24/25:Avoid contact with skin and eyes . | [WGK Germany ]
3
| [F ]
10 | [TSCA ]
No | [HS Code ]
2931.90.9010 |
| Hazard Information | Back Directory | [Chemical Properties]
clear colorless liquid | [Uses]
1,2-Bis(dimethylsilyl)benzene is a protecting group-reagent for amines and amino acids forming "benzostabase" derivatives. It is an important raw material and in organic synthesis. | [Synthesis]
General procedure for the synthesis of 1,2-bis(dimethylsilyl)benzene from dimethylmonochlorosilane and 1,2-dibromobenzene: a condenser was assembled in a dry 50 mL two-necked flask, and stirring bars, magnesium powder (99.9%, 24 mmol), lithium chloride (24 mmol), N,N'-dimethylimidazolidinone (DMI, 20 mL) and chlorodimethylsilane ( 48 mmol). After stirring the reaction mixture for 15 minutes at room temperature, 1,2-dibromobenzene (3 mmol) was added and stirring was continued for 4 hours. After completion of the reaction, the reaction was quenched with saturated sodium bicarbonate solution. The sodium bicarbonate and the resulting precipitate were removed by filtration. The filtrate was extracted with hexane (3 x 20 mL), the organic phases were combined, washed with saturated brine, dried over anhydrous sodium sulfate and concentrated by rotary evaporation. The crude product was purified by silica gel column chromatography, and the eluent was pure hexane or hexane/dichloromethane mixed solvent. | [References]
[1] Synthesis (Germany), 2017, vol. 49, # 11, p. 2495 - 2500
[2] Tetrahedron Letters, 2000, vol. 41, # 34, p. 6611 - 6614
[3] Tetrahedron, 1993, vol. 49, # 43, p. 9855 - 9866
[4] Journal of Organometallic Chemistry, 2018, vol. 854, p. 76 - 86
[5] Tetrahedron, 1991, vol. 47, # 47, p. 9807 - 9822 |
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