| Identification | More | [Name]
1,3-DICHLORO-1,1,3,3-TETRAISOPROPYLDISILOXANE | [CAS]
69304-37-6 | [Synonyms]
1,1,3,3-TETRAISOPROPYL-1,3-DICHLORODISILOXANE
1,3-DICHLORO-1,1,3,3-TETRAISOPROPYL-1,3-DISILOXANE
1,3-DICHLORO-1,1,3,3-TETRAISOPROPYLDISILOXANE
1,3-DICHLOROTETRAISOPROPYLDISILOXANE
1,3-DICHLOROTETRAISOPROPYLSILOXANE
TIPDSICL2
TIPSCL
1,1,3,3-Tetraisopropyl-1,3-dichlorosiloxane
chloro-(chloro-dipropan-2-yl-silyl)oxy-dipropan-2-yl-silane
1,3-DICHLORO-1,1,3,3-TETRAISOPROPYL-
Disiloxane, 1,3-dichloro-1,1,3,3-tetrakis(1-methylethyl)-
1,3-Dichloro-1,1,3,3-tetraisopropoxydisiloxane
1,3-Dichloro-1,1,3,3-tetraisopropyldisiloxane [Hydroxyl Protecting Agent]
1,1,3,3-Tetraisopropyl-1,3-dichloropropanedisiloxane
1,3-Dichloro-1,1,3,3-tetraisopropylpropanedisiloxane
2,6-Dimethyl-3,5-dichloro-3,5-diisopropyl-4-oxa-3,5-disilaheptane
Bis(chlorodiisopropylsilyl) ether | [EINECS(EC#)]
629-558-9 | [Molecular Formula]
C12H28Cl2OSi2 | [MDL Number]
MFCD00009655 | [Molecular Weight]
315.43 | [MOL File]
69304-37-6.mol |
| Chemical Properties | Back Directory | [Appearance]
Colorless liquid | [Boiling point ]
70 °C0.5 mm Hg(lit.)
| [density ]
0.986 g/mL at 25 °C(lit.)
| [refractive index ]
n20/D 1.454(lit.)
| [Fp ]
>230 °F
| [storage temp. ]
2-8°C
| [solubility ]
Miscible with dimethylformamide, hexane, ethyl acetate, chloroform and dichloromethane. | [form ]
Oil | [color ]
Colourless | [Specific Gravity]
0.986 | [Hydrolytic Sensitivity]
8: reacts rapidly with moisture, water, protic solvents | [Sensitive ]
Moisture Sensitive | [BRN ]
1934216 | [InChI]
InChI=1S/C12H28Cl2OSi2/c1-9(2)16(13,10(3)4)15-17(14,11(5)6)12(7)8/h9-12H,1-8H3 | [InChIKey]
DDYAZDRFUVZBMM-UHFFFAOYSA-N | [SMILES]
[Si](Cl)(C(C)C)(C(C)C)O[Si](Cl)(C(C)C)C(C)C | [CAS DataBase Reference]
69304-37-6(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
C | [Risk Statements ]
R34:Causes burns. | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S27:Take off immediately all contaminated clothing .
S28:After contact with skin, wash immediately with plenty of ... (to be specified by the manufacturer) .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) . | [RIDADR ]
UN 3265 8/PG 2
| [WGK Germany ]
3
| [F ]
10-21 | [Hazard Note ]
Corrosive | [TSCA ]
No | [HazardClass ]
8 | [PackingGroup ]
II | [HS Code ]
29319090 |
| Hazard Information | Back Directory | [Description]
1,3-Dichloro-1,1,3,3-tetraisopropyldisiloxane is a moisture-sensitive, colourless, transparent, corrosive liquid that is miscible with a wide range of organic solvents but insoluble in water. It can be used to protect the two hydroxyl groups in nucleoside and carbohydrate substrates simultaneously. It can also be used as a solvent for chromatography and as a reagent for polymer synthesis. In addition, it is a stabiliser for polymers and a surfactant for emulsions. | [Chemical Properties]
Colorless liquid | [Physical properties]
bp 70°C/0.5 mmHg; d 0.986 g cm?3. | [Uses]
1,3-Dichloro-1,1,3,3-tetraisopropyldisiloxane can be used as simultaneous protection of the 3'- and 5'-hydroxyl functions of
furanose nucleosides;protecting group for carbohydrates;3,4
protecting group reagent for open-chain polyhydroxy compounds;
preparation of cyclic bridged peptides.
The reagent
design was based upon the fact that triisopropylsilyl chloride
reacts 1000 times faster with primary alcohols than secondary
alcohols. Thus in the case of 3',5'-dihydroxy nucleosides the
reagent initially silylates at the 5'-position. This is then followed
by intramolecular reaction with the secondary alcohol at the
3'-position to give the doubly protected derivative (eq 1).
| [Uses]
1,3-Dichloro-1,1,3,3-tetraisopropyldisiloxane is used in the analysis of Watson-Crick and Hoogstein base pairing in nucleotides. Also used in the formation of ribavirin chemical delivery systems. | [Preparation]
can be prepared starting from trichlorosilane
by treatment with i-PrMgCl, H2O, and acetyl chloride.
Alternatively, it can be prepared by the reaction of 1,1,3,3-
tetraisopropyldisiloxane with CCl4 in the presence of catalytic
PdCl2.This method is also suitable for its in situ preparation. | [Hazard]
1,3-Dichloro-1,1,3,3-tetraisopropyldisiloxane is a silane-based reagent that is irritating to the eyes on contact and corrosive to the skin, causing burns; inhalation can cause corrosive damage to the upper respiratory tract and lungs. | [Synthesis]
General procedure for the synthesis of 1,3-dichloro-1,1,3,3-tetraisopropyldisiloxane from 1,1,3,3-tetraisopropyldisiloxane: The chlorination reaction needs to be carried out in THF, making sure that all Si-H bonds are chlorinated, using an excess of TCCA (molar ratio 1:1, TCCA to siloxane). This was done as follows: 1,1,3,3-tetraisopropyldisiloxane and THF (ratio 20 mL THF/g raw material) were added to the reaction flask and the mixture was cooled to -20 °C. TCCA was added in batches with vigorous stirring, and after the addition of TCCA, stirring was continued for 15 min, after which the cooling bath was removed and the reaction mixture was allowed to warm slowly to room temperature. It should be noted that the chain length, substituent or Si-H bond position of the siloxanes may affect the subsequent separation and characterization methods. Upon completion of the reaction, THF and unreacted TCCA need to be removed immediately to prevent denaturation of the product after several days. | [References]
[1] Synthetic Communications, 1987, vol. 17, # 11, p. 1299 - 1308
[2] Journal of Organometallic Chemistry, 2018, vol. 875, p. 1 - 4
[3] Tetrahedron Letters, 1999, vol. 40, # 6, p. 1197 - 1200
[4] Synthetic Communications, 1999, vol. 29, # 20, p. 3499 - 3501
[5] Journal of the American Chemical Society, 1983, vol. 105, # 12, p. 4059 - 4065 |
| Spectrum Detail | Back Directory | [Spectrum Detail]
1,3-DICHLORO-1,1,3,3-TETRAISOPROPYLDISILOXANE(69304-37-6)1HNMR
1,3-DICHLORO-1,1,3,3-TETRAISOPROPYLDISILOXANE(69304-37-6)IR
1,3-DICHLORO-1,1,3,3-TETRAISOPROPYLDISILOXANE(69304-37-6)Raman
1,3-DICHLORO-1,1,3,3-TETRAISOPROPYLDISILOXANE(69304-37-6)FT-IR
|
| Well-known Reagent Company Product Information | Back Directory | [Acros Organics]
1,3-Dichloro-1,1,3,3-tetraisopropyldisiloxane, 96%(69304-37-6) | [Alfa Aesar]
1,3-Dichloro-1,1,3,3-tetraisopropyldisiloxane, 97%(69304-37-6) | [Sigma Aldrich]
69304-37-6(sigmaaldrich) | [TCI AMERICA]
1,3-Dichloro-1,1,3,3-tetraisopropyldisiloxane [Hydroxyl Protecting Agent],>97.0%(GC)(69304-37-6) |
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