PCC
Pyridinium chlorochromate
CAS: 26299-14-9
Molecular Formula: C5H6ClCrNO3
PCC - Names and Identifiers
| Name | Pyridinium chlorochromate |
| Synonyms | PCC pyridinium Urine Luck PYRIDINIUM CHLOROCHROMATE Pyridinium chlorochromate Pyridine, chlorotrioxochromate(1-) pyridinium chloro(oxido)dioxochromium Pyridine, (T-4)-chlorotrioxochromate(1-) |
| CAS | 26299-14-9 |
| EINECS | 247-595-5 |
| InChI | InChI=1/C5H5N.ClH.Cr.3O/c1-2-4-6-5-3-1;;;;;/h1-5H;1H;;;;/q;;+1;;;-1/rC5H5N.ClCrO3/c1-2-4-6-5-3-1;1-2(3,4)5/h1-5H;/q;-1/p+1 |
| InChIKey | LEHBURLTIWGHEM-UHFFFAOYSA-N |
PCC - Physico-chemical Properties
| Molecular Formula | C5H6ClCrNO3 |
| Molar Mass | 215.55 |
| Melting Point | 205-208°C(lit.) |
| Boling Point | 115.3℃ at 760 mmHg |
| Solubility | Partly miscible with water. |
| Appearance | Orange crystal |
| Color | Orange |
| Exposure Limit | OSHA: Ceiling 0.1 mg/m3NIOSH: IDLH 15 mg/m3; TWA 0.0002 mg/m3 |
| Merck | 14,7974 |
| BRN | 7054643 |
| Storage Condition | Inert atmosphere,Room Temperature |
| Stability | Stable. May react with easily oxidized materials. Incompatible with reducing agents, combustible material, metals, strong reducing agents. |
| Sensitive | Moisture Sensitive |
| MDL | MFCD00013106 |
| Physical and Chemical Properties | Compared with other commonly used chromium-containing oxidants such as jons reagent and Colljn reagent, PCC has the characteristics of strong oxidation ability, good selectivity, and the alkene bond of the substrate molecule is not affected in the oxidation process, and easy to operate. In addition, the acidity of the daughter P CC is weak, so those groups that are unstable to the acid can still be preserved during oxidation. |
| Use | Usually used to oxidize an allylic methylene group. |
PCC - Risk and Safety
| Risk Codes | R49 - May cause cancer by inhalation R8 - Contact with combustible material may cause fire R43 - May cause sensitization by skin contact R50/53 - Very toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment. R20/21/22 - Harmful by inhalation, in contact with skin and if swallowed. |
| Safety Description | S53 - Avoid exposure - obtain special instructions before use. 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. S37 - Wear suitable gloves. S24 - Avoid contact with skin. S17 - Keep away from combustible material. S44 - S36/37/39 - Wear suitable protective clothing, gloves and eye/face protection. S22 - Do not breathe dust. |
| UN IDs | UN 1479 5.1/PG 2 |
| WGK Germany | 2 |
| TSCA | Yes |
| HS Code | 29333990 |
| Hazard Class | 5.1 |
| Packing Group | III |
PCC - Introduction
Used to oxidize an allylic methylene group in a synthesis of α,β-unsaturated lactones from D-glucose using Grubbs-catalyzed ring-closing metathesis. A stable versatile oxidizing agent for mild and selective oxidation of alcohols.
Last Update：2022-10-16 17:24:07
PCC - Reference Information
| EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
| Overview | Pyridine chlorochromate, molecular formula C5H4N · HCrO3Cl, abbreviated as PCC, is the abbreviation of Pyridinium chlorochromate, and the Chinese alias is Salit (Sarrett) reagent. PCC was first a new selective oxidant discovered by E.J.Corey after developmental research in 1975. Mainly used for the oxidation of alcohols to aldehydes/ketones, local selective oxidation of carbohydrates, oxidation of borane and oxime (deoxime reaction) to carboxyl compounds, and direct oxidation of alkenyl tertiary alcohols to unsaturated aldehydes; It can also make enols directly oxidized to esters or lactones. |
| application | pyridinium chlorochromate, commonly abbreviated as NBS, is a mild oxidant, orange-yellow crystal. Used to oxidize alcohols to aldehydes to a limited extent. The disadvantages of using PCC are that the reaction time is too long and PCC is toxic. The reagent itself is weakly acidic, so it is often used with buffers such as sodium acetate. |
| preparation | usually chromium trioxide is reacted with hydrochloric acid to form chlorochromic acid, and then pyridine is added at 0 ℃ to obtain orange stable pyridine chlorochromate solid: specific reaction steps: chromium trioxide (100g, 1 mol) is rapidly added to 6 N hydrochloric acid (184 ml, 1.1 mol) under stirring, after 5 minutes, when the uniform solution is cooled to 0 ℃, pyridine (79.1g, 1 mol) is carefully added within 10 minutes. The solution is re-cooled to 0 ℃ to obtain orange solid, the solid is collected on a sintered glass funnel for filtration, and dried in vacuum for 1 hour with a yield of 250.5g and 54%. |
| use | high-efficiency oxidant. It can be applied to large-scale oxidation reaction process, especially it can oxidize hydroxyl group to aldehyde group under room temperature and neutral conditions, and the reaction condition is mild. It is an oxidant worthy of popularization and application. In the process of synthesizing lactone natural products, we need to oxidize lactone alcohol to lactone aldehyde, but the lactone ring is easily destroyed under strong conditions, so PCC is selected to carry out this kind of oxidation reaction under suitable conditions. Oxidant, selective oxidation of alcohol. In the Grubbs-catalyzed closed-loop decomposition of D-glucose synthesis of unsaturated lactones for the oxidation of allylmethylene groups. PCC is an effective alcohol oxidant; allyl, benzyl methylene oxidant; aryl substituted olefin oxidative cracking agent; in D-glucose synthesis unsaturated lactone Grubbs catalytic closed-loop decomposition, used to oxidize allyl methylene; under mild conditions, for alcohols, stable, multifunctional selective oxidant. |
| production method | under stirring, add 100g (1 mol) of chromium trioxide in 184 ml of 6M hydrochloric acid 1.1 mol). After 5 minutes, the homogeneous solution is cooled to 0C, 79.1 grams (1 mole) of pyridine is carefully added within at least 10 minutes, and then cooled to 0°C to produce a yellow-orange solid, which is filtered with a glass core funnel. The product was dried under vacuum for 1 hour. Get 180.8 grams (84%). This solid is not significantly deliquescent and can be stored at room temperature for a period of time. |
Last Update：2024-04-10 22:29:15
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