Name | Sodium cyclopentadienide |
Synonyms | NACP CYCLOPENTADIENYLSODIUM SODIUM CYCLOPENTADIENIDE Sodium cyclopentadienide Sodiumcyclopentadienylide SODIUM CYCLOPENTADIENYLIDE Sodium cyclopentadienylide sodium cyclopenta-2,4-dienide cyclopenta-1,3-dien-1-ylsodium Cyclopentadienylsodium solution CYCLOPENTADIENYLSODIUM SOLUTION, ~2 M IN THF SODIUM CYCLOPENTADIENIDE, 2.0M SOLUTION IN TETRAHYDROFURAN |
CAS | 4984-82-1 |
EINECS | 225-636-8 |
InChI | InChI=1/C5H5.Na/c1-2-4-5-3-1;/h1-3H,4H2;/rC5H5Na/c6-5-3-1-2-4-5/h1-3H,4H2 |
InChIKey | PDTZVKVFAJGNRV-UHFFFAOYSA-N |
Molecular Formula | C5H5Na |
Molar Mass | 88.08 |
Density | 0.946g/mLat 20°C |
Melting Point | 172 °C |
Flash Point | 1°F |
Water Solubility | Reacts with water. |
Appearance | Liquid |
Color | dark red |
Exposure Limit | ACGIH: TWA 50 ppm; STEL 100 ppm (Skin)OSHA: TWA 200 ppm(590 mg/m3)NIOSH: IDLH 2000 ppm; TWA 200 ppm(590 mg/m3); STEL 250 ppm(735 mg/m3) |
BRN | 969542 |
Storage Condition | 2-8°C |
Sensitive | Air & Moisture Sensitive |
Risk Codes | R11 - Highly Flammable R19 - May form explosive peroxides R34 - Causes burns R40 - Limited evidence of a carcinogenic effect R37 - Irritating to the respiratory system R14/15 - |
Safety Description | S16 - Keep away from sources of ignition. 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. S45 - In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) S43 - In case of fire use ... (there follows the type of fire-fighting equipment to be used.) |
UN IDs | UN 1993 3/PG 2 |
WGK Germany | 3 |
FLUKA BRAND F CODES | 1-10 |
TSCA | Yes |
HS Code | 29319090 |
Hazard Class | 4.3 |
Packing Group | II |
EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
Study on the alkaline synthesis of sodium cyclopentadienyl | Cyclopentadienyl sodium (CPD-Na) has a 6π electron π bond and is highly stable (in inert gas It is a stable organometallic compound below 300 ℃) and easy to react, so it is an important intermediate for the synthesis of a variety of cyclopentadiene (CPD) derivatives. Cyclopentadiene (1,3-cyclopentadiene is abbreviated as CPD in English, abbreviated as "Mao" in Chinese), is a colorless flammable liquid with a boiling point of 41.5 ℃, insoluble in water, and easily soluble in ethanol, ether, Organic solvents such as carbon tetrachloride. Cyclopentadiene usually exists in the form of dimers (dicyclopentadiene is generally represented by DCPD). The methylene group in the cyclopentadiene molecule is more active due to the influence of the conjugated double bond in the two rings., Has a certain acidity, so it can be replaced by sodium metal to generate sodium cyclopentadienyl [1] 〕. (Cyclopentadienyl sodium is also called sodium metallocene, which is represented by CPD-Na below). Cyclopentadiene can also react with strong bases to form cyclopentadienyl anions. Cyclopentadienyl anion has a certain aromaticity, it is a relatively stable carbanion. Since cyclopentadienyl anions are non-benzene aromatic hydrocarbons, their electrophilic substitution reactions (SE) have been studied more [2] 〕. But cyclopentadienyl anion is a carbanion after all, it should have the property of nucleophilic substitution reaction (SN) with other compounds as a nucleophile [3] 〕. If the cyclopentadienyl anion and the R-X can smoothly undergo SN reaction, we can use this reaction to introduce various hydrocarbon groups to the metallocene ring, which will be useful for the synthesis of various cyclopentadienyl derivatives and New thermoplastic covalent crosslinked elastomers are of great significance [4] 〕. Therefore, we prepared CPD-Na by reacting CPD with NaOH, and prepared 1,2-dicyclopentadienyl ethane by reacting CPD-Na with BrCH2CH2Br, which proves that the above idea is feasible. author: Liu Changxin, Liu Siquan, School of Chemical Engineering, Jinan University, Yang Xiaofeng |