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| CAS No.: | 594-27-4 |
|---|---|
| Name: | TETRAMETHYLTIN |
| Article Data: | 232 |
| Molecular Structure: | |
|
|
|
| Formula: | C4H12Sn |
| Molecular Weight: | 178.849 |
| Synonyms: | Tin,tetramethyl- (6CI);Tetramethylstannane; |
| EINECS: | 209-833-6 |
| Density: | 1.291 g/mL at 25 °C(lit.) |
| Melting Point: | -54 °C(lit.) |
| Boiling Point: | 74.499 °C at 760 mmHg |
| Flash Point: | -12.778 °C |
| Solubility: | Insoluble in water. Soluble in organic solvents |
| Appearance: | clear colorless liquid |
| Hazard Symbols: |
 N;  T+
|
| Risk Codes: | 26/27/28-50/53 |
| Safety: | 26-27-28-45-60-61 |
| Transport Information: | UN 3384 6.1/PG 1 |
| PSA: | 0.00000 |
| LogP: | 1.95440 |
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| Conditions | Yield |
|---|---|
| With {(C2H5)4N}Br In acetonitrile Electrolysis; Sn-cathode, 50°C; | 100% |
| With {(C2H5)4N}Br In acetonitrile Electrolysis; Sn-cathode, 50°C; | 100% |
| In water; acetonitrile Electrolysis; Sn-cathode, Pt-anode, 0.25 M Et4NClO4 in MeCN/water=7:1, 25°C, 10mA/cm**(-2); gas chromy.; |
| Conditions | Yield |
|---|---|
| In benzene molar ratio 2 : 1, room temp.; | 100% |
| In benzene molar ratio 2 : 1, room temp.; | 100% |
| Conditions | Yield |
|---|---|
| 80°C; | 99% |
| 80°C; | 99% |
| Conditions | Yield |
|---|---|
| In neat (no solvent) stirring under N2, helding at room temp. for 4 h; destilling Me3SnCl and Me4Sn off under reduced pressure, recrystn. from ethanol, elem. anal.; | A 96% B n/a |
| Conditions | Yield |
|---|---|
| In further solvent(s) equimolar NaCl-AlCl3 melt, 220°C; | 95% |
| In further solvent(s) equimolar NaCl-AlCl3 melt, 220°C; | 95% |
| Conditions | Yield |
|---|---|
| In dichloromethane N2-atmosphere; refluxing for 72 h; evapn., addn. of hexane, collection (filtration), drying (vac.); elem. anal.; | A 95% B n/a |
| Conditions | Yield |
|---|---|
| In neat (no solvent) stirring under N2, room temp., 6 h.; Evapn., recrystn. (ethanol). Elem. anal.; | A 93.5% B n/a |
| Conditions | Yield |
|---|---|
| In diethyl ether | A 92% B n/a C n/a |
| In diethyl ether | A 92% B n/a C n/a |
- 36333-59-2
1,3-dimethyl-2-(trimethylstannyl)-2-bora-1,3-diazacyclopentane
- 15630-15-6
dimethyl(1,2-bis(dimethylphosphino)ethane)palladium(II)
A
- 29173-12-4
1,2,3-trimethyl-[1,3,2]diazaborolidine
C
- 594-27-4
tetramethylstannane
| Conditions | Yield |
|---|---|
| In benzene-d6 130°C (17 h); recrystn. (toluene / pentane = 1 : 4); elem. anal.; | A 91% B 68% C 84% |
| Conditions | Yield |
|---|---|
| In dibutyl ether | 90% |
| In dibutyl ether | 90% |
| In dibutyl ether | 89% |
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Consensus Reports
Reported in EPA TSCA Inventory.
Standards and Recommendations
OSHA PEL: TWA 0.1 mg(Sn)/m3 (skin)
ACGIH TLV: TWA 0.1 mg(Sn)/m3; STEL 0.2 mg(Sn)/m3 (skin).
NIOSH REL: (Organotin Compounds) TWA 0.1 mg(Sn)/m3
Analytical Methods
For occupational chemical analysis use NIOSH: Organotin Compounds 5504.
Specification
The IUPAC name of this chemical is Tetramethylstannane. With the CAS registry number 594-27-4 and EINECS registry number 209-833-6, it is also named as stannane, tetramethyl-. In addition, the molecular formula is C4H12Sn and the molecular weight is 178.85. It is a kind of clear colorless liquid and belongs to the classes of Alkyl Metals; Classes of Metal Compounds; Grignard Reagents & Alkyl Metals; Sn (Tin) Compounds; Synthetic Organic Chemistry; Typical Metal Compounds.
Physical properties about this chemical are: (1)ACD/LogP: 3.49; (2)ACD/LogD (pH 5.5): 3.49; (3)ACD/LogD (pH 7.4): 3.49; (4)ACD/BCF (pH 5.5): 262.8; (5)ACD/BCF (pH 7.4): 262.8; (6)ACD/KOC (pH 5.5): 1877.48; (7)ACD/KOC (pH 7.4): 1877.48; (8)Flash Point: °C; (9)Enthalpy of Vaporization: 30.26 kJ/mol; (10)Boiling Point: 74.5 °C at 760 mmHg; (11)Vapour Pressure: 120 mmHg at 25°C.
Preparation of Tetramethylstannane: it can be prepared by methylmagnesium iodide and tin tetrachloride, which is synthesized by reacting tin metal with chlorine gas. The equation is as follows: 4CH3MgI + SnCl4 → (CH3)4Sn + 4MgICl.
Uses of Tetramethylstannane: its liquid is useful for transition-metal mediated conversion of acid chlorides to methyl ketones and aryl halides to aryl methyl ketones. It can react with SnMe4 to get Me3SnCl at temperatures between 100 °C and 200 °C. The equation is as follows: SnCl4 + 3SnMe4 → 4 Me3SnCl. In addition, it can react with 1-iodo-4-nitro-benzeneto give 1-methyl-4-nitro-benzene. This reaction will need reagent PhPdI(PPh3)2 and solvent hexamethylphosphoric acid triamide. The reaction time is 0.5 hour at reaction temperature of 70 °C. The yield is about 87%.
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When you are using this chemical, please be cautious about it as the following:
This chemical is very Toxic by inhalation, in contact with skin and if swallowed. And it is very Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment. During using it, you should avoid release to the environment. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. If contact it with your skin, wash it immediately with plenty of ... (to be specified by the manufacturer). Moreover, take off immediately all contaminated clothing. In case of accident or if you feel unwell, seek medical advice immediately (show label where possible). This material and/or its container must be disposed of as hazardous waste. And you can refer to special instructions safety data sheet.
You can still convert the following datas into molecular structure:
(1)SMILES: C[Sn](C)(C)C
(2)InChI: InChI=1/4CH3.Sn/h4*1H3;/rC4H12Sn/c1-5(2,3)4/h1-4H3
(3)InChIKey: VXKWYPOMXBVZSJ-RMHPNCEBAE
The toxicity data is as follows:
| Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
|---|---|---|---|---|---|
| mouse | LCLo | inhalation | 2550mg/m3/10M (2550mg/m3) | SENSE ORGANS AND SPECIAL SENSES: LACRIMATION: EYE BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD LUNGS, THORAX, OR RESPIRATION: DYSPNEA | National Defense Research Committee, Office of Scientific Research and Development, Progress Report.Vol. NDCrc-132, Pg. FEB1942, |
| mouse | LD50 | intraperitoneal | 18mg/kg (18mg/kg) | "Prehled Prumyslove Toxikologie; Organicke Latky," Marhold, J., Prague, Czechoslovakia, Avicenum, 1986Vol. -, Pg. 1245, 1986. |