| Identification | Back Directory | [Name]
1-CHLORO-1-METHYLSILACYCLOBUTANE | [CAS]
2351-34-0 | [Synonyms]
1-Chloro-1-methylsiletane
1-CHLORO-1-METHYLSILACYCLOBUTANE
Silacyclobutane, 1-chloro-1-methyl-
CYCLOTRIMETHYLENEMETHYLCHLOROSILANE
1-Chloro-1-Methylsilacyclobutane 98% | [Molecular Formula]
C4H9ClSi | [MDL Number]
MFCD00191926 | [MOL File]
2351-34-0.mol | [Molecular Weight]
120.65 |
| Chemical Properties | Back Directory | [Boiling point ]
103 °C(lit.) | [density ]
0.985 g/mL at 25 °C(lit.) | [refractive index ]
n20/D 1.45(lit.) | [Fp ]
37 °F | [solubility ]
soluble in most aprotic organic solvents. | [form ]
liquid | [Specific Gravity]
0.985 | [Hydrolytic Sensitivity]
8: reacts rapidly with moisture, water, protic solvents |
| Hazard Information | Back Directory | [Physical properties]
bp 103°C; d 0.985 g cm?3. | [Uses]
Intermediate in the formation of enoxysilacyclobutanes. | [Uses]
Siletanes (silacyclobutanes) represent a unique
class of silicon-based reagents that have enjoyed much success in
a number of synthetic applications including aldol reactions, allylations,
cross-coupling reactions, carbosilane oxidations, and ring
expansions. The manifestation of their strain in enhanced Lewis
acidity and in the ring opening to silanols accounts for their utility.
1-Chloro-1-methylsiletane can be used for the preparation of the
various siletane derivatives for these applications.
Grignard reagents react efficiently with 1-chloro-1-methylsiletane
to provide the corresponding aryl-, alkenyl-, or alkylsiletanes
(eqs 1–3).On the contrary, reactions with alkyllithiums are
limited to the reaction of 1 with a lithium acetylide (eq 4).The
reaction of 1 with an intermediate vinylalane obtained by hydroalumination
of 1-heptyne gave (E)-1-heptenylmethylsiletane
in >99/1 isomeric purity (eq 5).The reaction of 1 with LiAlD4
afforded 1-deuterio-1-methylsiletane (eq 6).
| [Preparation]
siletane can be prepared in large quantities
byWurtz coupling reaction of dichloro-3-chloropropylmethylsilane
with Mg.It is commercially available from Gelest
and Aldrich chemical company. |
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