LITHIUM SEC-BUTYL
sec-Butyllithium
CAS: 598-30-1
Molecular Formula: C4H9Li
LITHIUM SEC-BUTYL - Names and Identifiers
| Name | sec-Butyllithium |
| Synonyms | S-BULI S-BUTYLLITHIUM s-Butyllithium SEC-BUTYLLITHIUM sec-Butyllithium butan-2-yllithium LITHIUM SEC-BUTYL LITHIUM-2-BUTANIDE lithium butan-2-ide (2-methylpropyl)lithium sec-Butyllithium solution Sec-butyllithium 1.4M in cyclohexane ButyllithiumincyclohexanecaMcolorlesslightyellow sec-Butyllithium, 1.0 M solution in Hexane, HySeal |
| CAS | 598-30-1 |
| EINECS | 209-927-7 |
| InChI | InChI=1/C4H9.Li/c1-4(2)3;/h4H,1H2,2-3H3;/rC4H9Li/c1-4(2)3-5/h4H,3H2,1-2H3 |
| InChIKey | VATDYQWILMGLEW-UHFFFAOYSA-N |
LITHIUM SEC-BUTYL - Physico-chemical Properties
| Molecular Formula | C4H9Li |
| Molar Mass | 64.06 |
| Density | 0.769g/mLat 25°C |
| Flash Point | 1°F |
| Appearance | Liquid |
| Color | Clear colorless |
| Exposure Limit | ACGIH: TWA 100 ppmOSHA: TWA 300 ppm(1050 mg/m3)NIOSH: IDLH 1300 ppm; TWA 300 ppm(1050 mg/m3) |
| BRN | 3587206 |
| Storage Condition | 2-8°C |
| Sensitive | Air & Moisture Sensitive |
LITHIUM SEC-BUTYL - Risk and Safety
| Risk Codes | R11 - Highly Flammable R15 - Contact with water liberates extremely flammable gases R17 - Spontaneously flammable in air R34 - Causes burns R50/53 - Very toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment. R65 - Harmful: May cause lung damage if swallowed R67 - Vapors may cause drowsiness and dizziness R66 - Repeated exposure may cause skin dryness or cracking R51/53 - Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment. R14/15 - |
| Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S36/37/39 - Wear suitable protective clothing, gloves and eye/face protection. S43 - In case of fire use ... (there follows the type of fire-fighting equipment to be used.) S45 - In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) S60 - This material and its container must be disposed of as hazardous waste. S61 - Avoid release to the environment. Refer to special instructions / safety data sheets. S62 - If swallowed, do not induce vomitting; seek medical advice immediately and show this container or label. S33 - Take precautionary measures against static discharges. S16 - Keep away from sources of ignition. |
| UN IDs | UN 3394 4.2/PG 1 |
| WGK Germany | 2 |
| FLUKA BRAND F CODES | 1-10 |
| TSCA | Yes |
| HS Code | 29319090 |
| Hazard Class | 4.3 |
| Packing Group | I |
LITHIUM SEC-BUTYL - Reference Information
| EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
| appearance | colorless or yellowish transparent liquid. |
| product quality standard | the product should be insulated from air and water to the maximum extent during the activation process, and should be frozen and stored at -7 ℃ ~-4 ℃, preferably at one time. If it is found that there is color difference or trace precipitation in this product, it will not affect the performance of the product. Quality standard: alkaline impurities ≤ 1.0%(max) (calculated as sec-butoxy) covalent chlorine and Cl- ≤ 0.1%(max). |
| use | 1. lidisant. Polymerization of isoprene and butadiene. Preparation of lithium hydride, tetrahydrofuran, and benzyl lithium compounds. 2. Compared with n-butyl lithium, isobutyl lithium has stronger alkalinity, higher metallization activity and worse nucleophilicity. Therefore, for the lithiation reaction of weakly acidic substrates that n-butyl lithium cannot act, such as the preparation of aryl, vinyl, and allyl lithium reagents, and when weak nucleophilic lithiation reagents are required, isobutyl Lithium is a good choice. Similar to n-butyl lithium, the reaction involving isobutyl lithium should also be carried out in electron donating solvents such as ether, THF and dimethyl ethane (DME), with the purpose of promoting the aggregation of low-order organic lithium. When combined with tertiary polyamine ligands such as HMPA, TMEDA or DABCO, isobutyllithium is more active. For example, s-BuLi/TMEDA complex is a highly reactive lithiating reagent, which can effectively deprotonate with inert substrates such as benzene, TMS and propylene (Formula 1). The lithiation reaction of heteroatom compounds involved in isobutyl lithium can obtain good regioselectivity, because heteroatoms such as oxygen, nitrogen, sulfur, phosphorus and halogen can activate α-through induction or conjugation effects. Or the hydrogen atom at the β-position. For example, the α-lithiation reaction of vinyl sulfide, vinyl chloride or vinyl thioester participating in isobutyl lithium at low temperature (Formula 2). Organic catalytic reaction. sec-butyl lithium solution is widely used in pharmaceutical intermediates, liquid crystal monomers, pesticides and organic reactions of rubber synthesis. |
| quenching method | slowly pour into tetrahydrofuran with a small amount of dry ice, slowly add twice the excess amount of ethanol, then add water to dilute, finally add dilute HCl until the solution becomes clear, and pour into the corresponding waste liquid barrel in the floor fume hood. Problems to be considered in quenching treatment: 1) Choose a suitable quenching reagent, and fully consider the stability of the product and the difficulty of post-treatment; 2) If the quenching process will release a lot of heat, it must be quenched under cooling; 3) Don't rely too much on the literature without monitoring the reaction. Only when TLC or other analytical means show the end of the reaction can the reaction be quenched; 4) If possible, post-treatment should be carried out as soon as possible after quenching. |
Last Update：2024-04-10 22:29:15
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