| Identification | More | [Name]
Tributyltin | [CAS]
688-73-3 | [Synonyms]
TIN TRIBUTYL HYDRIDE
TRIBUTYLSTANNANE
TRIBUTYLTIN HYDRIDE
TRI-N-BUTYLSTANNANE
TRI-N-BUTYLTIN
TRI-N-BUTYLTIN HYDRIDE
Stannane, tributyl-
Stannane, tri-n-butyl-, hydride
Tin, tri-n-butyl-, hydride
tributyl-stannan
Tributylstannic hydride
tributylstannichydride
tri-n-butylstannanehydride
tri-n-butyl-stannanhydride
tri-n-butyl-tihydride
Tri-n-butyltinhydride,97%
Tri-n-butyltinhydride,98+%
Tri-n-butyltinhydride,min.95%
tbth
TRIBUTYLTINHYDRIDE,TECHNICAL | [EINECS(EC#)]
211-704-4 | [Molecular Formula]
C12H28Sn | [MDL Number]
MFCD00009416 | [Molecular Weight]
291.06 | [MOL File]
688-73-3.mol |
| Chemical Properties | Back Directory | [Appearance]
clear colourless liquid | [Melting point ]
<0°C | [Boiling point ]
80 °C0.4 mm Hg(lit.) | [density ]
1.082 g/mL at 25 °C(lit.)
| [vapor pressure ]
5 hPa (20 °C) | [refractive index ]
n20/D 1.473(lit.)
| [Fp ]
104 °F
| [storage temp. ]
2-8°C
| [form ]
liquid | [color ]
colorless | [Specific Gravity]
1.103 (20℃) | [Water Solubility ]
REACTS | [Hydrolytic Sensitivity]
7: reacts slowly with moisture/water | [Sensitive ]
Air & Moisture Sensitive | [BRN ]
3587329 | [Uses]
Tributyltin hydride the most commonly used tin hydride，it is less toxic than the more volatile trierhyl and trimethyl analogues, and it is therefore the most widely used organostannane.
Tributyltin hydride, the reagent of choice for generating alkyl radical, is also widely used in aryl radical cyclization. Other reagents developed for this purpose include samarium diiodide, palladium reagents organosilanes as well as manganese triacetate and transition metals for carbocyclization. | [CAS DataBase Reference]
688-73-3(CAS DataBase Reference) | [NIST Chemistry Reference]
Tri-n-butyltin hydride(688-73-3) | [EPA Substance Registry System]
688-73-3(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
T,N,F | [Risk Statements ]
R10:Flammable.
R21:Harmful in contact with skin.
R25:Toxic if swallowed.
R36/38:Irritating to eyes and skin .
R48/23/25:Toxic: danger of serious damage to health by prolonged exposure through inhalation and if swallowed .
R50/53:Very Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment .
R15:Contact with water liberates extremely flammable gases.
R67:Vapors may cause drowsiness and dizziness.
R65:Harmful: May cause lung damage if swallowed.
R11:Highly Flammable. | [Safety Statements ]
S35:This material and its container must be disposed of in a safe way .
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) .
S60:This material and/or its container must be disposed of as hazardous waste .
S61:Avoid release to the environment. Refer to special instructions safety data sheet .
S62:If swallowed, do not induce vomiting: seek medical advice immediately and show this container or label .
S36/37:Wear suitable protective clothing and gloves .
S33:Take precautionary measures against static discharges .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S16:Keep away from sources of ignition-No smoking . | [RIDADR ]
UN 1993 3/PG 3
| [WGK Germany ]
3
| [RTECS ]
WH8675000
| [F ]
1-10 | [Autoignition Temperature]
>250 °C | [TSCA ]
Yes | [HazardClass ]
6.1 | [PackingGroup ]
II | [HS Code ]
29310095 | [Safety Profile]
Moderately toxic by
inhalation. When heated to decomposition it
emits acrid smoke and irritating fumes. See
also TIN COMPOUNDS. | [Hazardous Substances Data]
688-73-3(Hazardous Substances Data) |
| Questions And Answer | Back Directory | [Uses]
Tributyltin hydride (TBTH) is as a reagent for the reductive ionic 1,5-cyclization of 3-azamuconoates (3-azahexa-2,4-dienedioates).
Tributyltin hydride can also mediate cyclisation of unsaturated ethers and amines bearing an aldehyde or α,β-unsaturated ketone group.
Tributyltin hydride is also a reducing agent for the reduction of nitroalkenes.
|
| Hazard Information | Back Directory | [Chemical Properties]
clear colourless liquid | [Hazard]
Moderately toxic by inhalation. | [Purification Methods]
Dissolve it in Et2O, add quinol (500mg for 300mL, to stabilize it), dry over Na2SO4, filter, evaporate and distil it under dry N2. It is a clear liquid if dry and decomposes very slowly. In the presence of H2O, traces of tributyl tin hydroxide are formed in a few days. Store it in sealed glass ampoules in small aliquots. It is estimated by reaction with aqueous NaOH when H2 is liberated. CARE: stored samples may be under pressure due to liberated H2. [Van Der Kerk et al. J Appl Chem 7 366 1937, Ono et al. Tetrahedron 41 4013 1985, Neuman Synthesis 665 1987, Curran Synthesis 417 1988, Beilstein 4 IV 4312.] |
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