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Hexamethyldisilane

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Hexamethyldisilane Basic information

Product Name:
Hexamethyldisilane
Synonyms:
  • HEXAMETHYLDISILANE
  • HMD
  • DISILANE M6
  • (CH3)6Si2
  • 1,1,1,2,2,2-Hexamethyldisilane
  • CH7280
  • disilane,hexamethyl-
  • Hecamethyldisilane
CAS:
1450-14-2
MF:
C6H18Si2
MW:
146.38
EINECS:
215-911-0
Product Categories:
  • organosilicon compounds
  • Pharmaceutical Intermediates
  • Blocking Agents
  • Protective Agents
  • Chemical Synthesis
  • Organometallic Reagents
  • Standards for NMR
  • Silylating Agents
  • Special Silanes
  • DisilanesVapor Deposition Precursors
  • Organometallic Reagents
  • Organosilicon
  • Precursors by Metal
  • Disilanes
  • Analytical Chemistry
  • NMR Spectrometry
  • Si (Classes of Silicon Compounds)
  • Silicon Compounds (for Synthesis)
  • Si-Si Compounds
  • Synthetic Organic Chemistry
  • K00001
  • bc0001
Mol File:
1450-14-2.mol
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Hexamethyldisilane Chemical Properties

Melting point:
9-12 °C (lit.)
Boiling point:
112-114 °C (lit.)
Density 
0.715 g/mL at 25 °C (lit.)
refractive index 
n20/D 1.422(lit.)
Flash point:
29 °F
storage temp. 
Store at <= 20°C.
solubility 
sol common organic solvents; insol H2O.
form 
liquid
Specific Gravity
0.729
color 
colorless
Water Solubility 
Insoluble in water. Soluble in alcohol, ether and acetone.
Hydrolytic Sensitivity
1: no significant reaction with aqueous systems
BRN 
1633463
Stability:
Volatile
InChIKey
NEXSMEBSBIABKL-UHFFFAOYSA-N
CAS DataBase Reference
1450-14-2(CAS DataBase Reference)
NIST Chemistry Reference
Disilane, hexamethyl-(1450-14-2)
EPA Substance Registry System
Disilane, hexamethyl- (1450-14-2)
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Safety Information

Hazard Codes 
F,Xi
Risk Statements 
11-36/37-43-36/37/38
Safety Statements 
16-23-45-9-33-26-7/9
RIDADR 
UN 1993 3/PG 2
WGK Germany 
2
RTECS 
JM9170000
TSCA 
Yes
HazardClass 
3
PackingGroup 
II
HS Code 
29310095
Toxicity
LD50 orally in Rabbit: 2160 mg/kg LD50 dermal Rabbit 2160 mg/kg

MSDS

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Hexamethyldisilane Usage And Synthesis

Chemical Properties

Colorless clear liquid

Uses

Hexamethyldisilane acts as a silylating reagent for allylic acetates, aryl halides and diketones. It is a source material for vapor deposition during silicon carbide growth. It is also used in electronic and semiconducter industries.

Application

Hexamethyldisilane is an important silane protective agent, which can synthesize sodium trimethylsilane, potassium trimethylsilane and lithium trimethylsilane.
Preparation of iodotrimethylsilane.
Used as trimethylsilane anion reagent.
silylating or reducing reagent in combination with a Pd catalyst or a nucleophile.
Replaces aromatic nitriles with TMS groups in presence of [RhCl(cod)]2.
Precursor for CVD of silicon carbide.
Brings about the homocoupling of arenesulfonyl chlorides in the presence of Pd2(dba)3.
Used as a solvent for the direct borylation of fluoroaromatics.
Reacts with alkynes to form siloles.
Undergoes the silylation of acid chlorides to give acylsilanes.

Preparation

Hexamethyldisilane is produced by the reaction of methyl Grignard reagent with methylchlorodisilanes. This reaction is normally conducted in the presence of an ether such as diethyl ether, ethyl propyl ether, THF and the like.

Fire Hazard

Hexamethyldisilazane (HMDZ) is a highly flammable liquid and vapour.
HMDZ liquid is lighter than water and may float on water, spreading material during fire fighting. Leaking material or fire runoff to sewer may create fire or explosion hazard.
HMDZ vapours are heavier than air and can accumulate to form explosive concentrations. The vapours may also spread a considerable distance to a source of ignition, and flash back towards the source.
HMDZ reacts with water to form ammonia.
HMDZ is a non-conductor and, therefore, can accumulate static electrical charges when processed, handled or dispensed. HMDZ's flash point is 52 to 53°F, closed cup, for "pure" material.

Purification Methods

The most likely impurity is trimethylchlorosilane (cf boiling point). Wash it with H2O, cold conc H2SO4, H2O again, then aqueous NaHCO3, dry over CaSO4 and fractionate at atmospheric pressure. [Brown & Fowles J Chem Soc 2811 1958.] A grossly impure sample (25% impurities) was purified by repeated spinning band distillation. This lowered the impurity level to 500ppm. The main impurity was identified as 1-hydroxypentamethyldisilane. [Beilstein 4 IV 4277.]

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