Chemical Name | Tetrabutylammonium Fluoride |
MDL Number | MFCD00011747 |
PubChem Substance ID | 2724141 |
CAS Number | 429-41-4 |
Reaxys-RN | 3570522 |
Merck Number | 9187 |
Beilstein Registry Number | 3762762 |
Synonym |
Tetrabutylammonium (fluoride)
{LY} Tetrabutylammonium (fluoride)
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EC Number | 207-057-2 |
Chemical Name Translation | 四丁基氟化铵 |
LabNetwork Molecule ID | LN00163257 |
InChI | InChI=1S/C16H36N.FH/c1-5-9-13-17(14-10-6-2,15-11-7-3)16-12-8-4;/h5-16H2,1-4H3;1H/q+1;/p-1 |
Canonical SMILES | CCCC[N+](CCCC)(CCCC)CCCC.[F-] |
WGK Germany | 3 |
GHS Symbol
Precautionary statements | |
- P210 Keep away from heat/sparks/open flames/hot surfaces. — No smoking. 远离热源/火花/明火/热的表面。——禁止吸烟。
- P233 Keep container tightly closed. ?保持容器密闭。
- P240 Ground/bond container and receiving equipment. 与地面接触/连接集装箱和接受设备。
- P241+P242+P243
- P260 Do not breathe dust/fume/gas/mist/vapours/spray. 不要吸入粉尘/烟/气体/烟雾/蒸汽/喷雾。
- P261 Avoid breathing dust/fume/gas/mist/vapours/spray. 避免吸入粉尘/烟/气体/烟雾/蒸汽/喷雾。
- P264 Wash hands thoroughly after handling. 处理后要彻底洗净双手。
- P270 Do not eat, drink or smoke when using this product. 使用本产品时不要吃东西,喝水或吸烟。
- P271 Use only outdoors or in a well-ventilated area.? 只能在室外或通风良好的地方使用。
- P280 Wear protective gloves/protective clothing/eye protection/face protection. 戴防护手套/防护服/眼睛的保护物/面部保护物。
- P301+P330+P331
- P301+P330+P331+P310
- P303+P361+P353+P310+P363
- P304+P340+P310
- P305+
- P305+P351+P338
- P305+P351+P338+P310
- P308+P311
- P310 Immediately call a POISON CENTER or doctor/physician. 立即呼救解毒中心或医生/医师。
- P370+P378
- P403 Store in a well-ventilated place. 储存在通风良好的地方。
- P403+P233
- P403+P235
- P405 Store locked up. 上锁保管。
- P501 Dispose of contents/container to..… 处理内容物/容器.....
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Hazard statements | |
- H314 Causes severe skin burns and eye damage 导致严重的皮肤灼伤和眼睛损伤
- H351 Suspected of causing cancer 怀疑致癌
- H225 Highly flammable liquid and vapour 高度易燃液体和蒸气
- H335 May cause respiratory irritation 可能导致呼吸道刺激
- H302+H312+H332
- H302 Harmful if swallowed 吞食有害
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Hazard Codes |
3
F,C |
Personal Protective Equipment |
Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
Faceshields, full-face respirator (US), Gloves, Goggles, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter |
Signal word |
Danger |
UN Number |
1759
2924
UN2924 |
Safety Statements | |
- S16 Keep away from sources of ignition - No smoking 远离火源,禁止吸烟;
- S26 In case of contact with eyes, rinse immediately with plenty of water and seek medical advice 眼睛接触后,立即用大量水冲洗并征求医生意见;
- S27 Take off immediately all contaminated clothing 立即脱掉全部污染的衣服;
- S33 Take precautionary measures against static discharges 对静电采取预防措施;
- S36/37/39 Wear suitable protective clothing, gloves and eye/face protection 穿戴适当的防护服、手套和眼睛/面保护;
- S45 In case of accident or if you feel unwell seek medical advice immediately (show the label where possible) 发生事故时或感觉不适时,立即求医(可能时出示标签);
- S60 This material and its container must be disposed of as hazardous waste 该物质及其容器必须作为危险废物处置;
- S9 Keep container in a well-ventilated place 保持容器在通风良好的场所;
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Packing Group | II |
Risk Statements | |
- R11 Highly flammable 非常易燃
- R19 May form explosive peroxides 可能生成易爆的过氧化物质
- R34 Causes burns 会导致灼伤
- R37 Irritating to respiratory system 刺激呼吸道
- R40 Limited evidence of a carcinogenic effect 有限证据表明其致癌作用
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Storage condition |
2-8°C
{LY} 2-8°C
Hygroscopic
Store at room temperature
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Hazard Class | 3/8 |
用于酰基化,硅化反应和硅醚解理的催化剂
{ALF} Fluoride ion as a base in organic synthesis: Chem. Rev., 80, 429 (1980). Synthetic aspects of the use of organosilicon compounds under nucleophilic catalysis conditions: Tetrahedron, 44, 2675 (1988). For a brief feature on uses of TBAF, see: Syn
{ALF} For the cleavage of disilanes to give "metal-free" silyl anions, see Hexamethyl­disilane, A13155.
{ALD} Merck: 14,9187
{ALF} For nucleophilic displacement of halide or tosylate by TBAF in the preparation of alkyl and acyl fluorides, see: J. Org. Chem., 49, 3216 (1984); Org. Synth. Coll., 8, 258 (1993).
{ALF} Mild catalyst for the silylation of OH by silazanes: Tetrahedron Lett., 35, 8409 (1994), or by hydrosilanes and disilanes: Tetrahedron Lett., 35, 8413 (1994). See Appendix 4.
{ALF} Ester enolates can be displaced from silicon, and trapped by reaction with carbonyl compounds without ɑ-hydrogens: Tetrahedron Lett., 1699 (1976). Under similar conditions, ketones with ɑ-hydrogens are converted under kinetic control to their silyl enol ethers with high (Z)-stereoselectivity (see Ethyl­ (trimethyl­silyl)­acetate, A17707): J. Am. Chem. Soc., 98, 2346 (1976); Org. Synth. Coll., 7, 512 (1990):
{ALF} Reagent for deprotection of N-Boc groups under mild conditions: Tetrahedron Lett., 43, 589 (2002).
{ALF} Promotes the directed aldol condensation of silyl enol ethers with aldehydes at low temperatures under very mild conditions: J. Org. Chem., 48, 932 (1983); alkali metal fluorides give poor results.
{ALF} Many other examples exist where the reagent acts as a base in organic synthesis:
{ALF} Specific reagent for the cleavage of silyl ethers, including TBDMS: J. Am. Chem. Soc., 94, 6190 (1972), (see tert-Butyl­dimethyl­chlorosilane, A13064), as well as the more stable TBDPS: Org. Synth. Coll., 9, 4 (1998), and TIPS: J. Org. Chem., 45, 4797 (1980); (see also tert-Butyl­diphenyl­chlorosilane, A12721 and Chlorotriisopropyl­silane, A17376).
{ALF} Reviews: