What molecule am I?
Epichlorohydrin, aka 2-(chloromethyl)oxirane, is a hazardous bifunctional liquid with a chloroform-like odor. The article of commerce is normally a racemic mixture of its two enantiomers; the 3-D image shown here is the (+)-isomer1.
In 1848, the pioneering French chemist Marcellin Berthelot鈥攁t the age of 21鈥攚as the first to describe epichlorohydrin. He prepared it by treating glycerol with hydrogen chloride gas. Berthelot鈥檚 synthesis has since been refined and is the basis of the modern manufacturing process. An alternative method is the epoxidation of allyl chloride. Current worldwide production is estimated to be >2 million tonnes.
By far the largest use of epichlorohydrin is in the production of epoxy resins. It is most often combined with bisphenol A in a base-catalyzed condensation reaction to produce the resin bisphenol A diglycidyl ether2. It is also used as a reagent for chemical and polymer synthesis and as a solvent for resins and coatings.
The health hazards associated with epichlorohydrin, bisphenol A, and epoxy resins require the use of protective equipment and adequate ventilation.
1. CAS Reg. No. 67843-74-7.
2. CAS Reg. No. 1675-54-3.
(卤)-贰辫颈肠丑濒辞谤辞丑测诲谤颈苍聽hazard information*
| Hazard class** | GHS code and hazard statement | |
|---|---|---|
| Flammable liquids, category 3 | H226鈥擣lammable liquid and vapor |  |
| Acute toxicity, oral, category 3 | H301鈥擳oxic if swallowed |  |
| Acute toxicity, dermal, category 3 | H311鈥擳oxic in contact with skin | |
| Skin corrosion/irritation, category 1B | H314鈥擟auses severe skin burns and eye damage |  |
| Skin sensitization, category 1 | H317鈥擬ay cause an allergic skin reaction |  |
| Serious eye damage/eye irritation, category 1 | H318鈥擟auses serious eye damage | |
| Acute toxicity, inhalation, category 3 | H331鈥擳oxic if inhaled | |
| Specific target organ toxicity, single exposure, respiratory tract irritation, category 3 | H335鈥擬ay cause respiratory irritation | |
| Carcinogenicity, category 1A | H350鈥擬ay cause cancer |  |
Short-term (acute) aquatic hazard, category 3 | H402鈥擧armful to aquatic life | |
*Compilation of two safety data sheets; other data sheets list additional hazards.
**Globally Harmonized System (GHS) of Classification and Labeling of Chemicals.聽.
Molecules from the journals
Harmaline1 (4,9-dihydro-7-methoxy-1-methyl-3H-pyrido[3,4-b]indole) is a fluorescent indole alkaloid that was by F. Goebel of Dorpat (now Tartu), Estonia, from the seeds of Peganum harmala, or Syrian rue, a Mediterranean herb. It has since been found in other plants. It is a central nervous system inhibitor and an amine oxidase inhibitor that is psychoactive in humans and prohibited or controlled in some countries.
This past April, Adela M. S谩nchez-Moreiras and collaborators at the University of Vigo (Spain) and the University of Milan (Italy) reported that harmaline may be a useful natural herbicide. In a search for herbicides with modes of action different from current ones to which weeds have developed resistance, the researchers used the common weed Arabidopsis thaliana as a model target to test the potency of harmaline, which had shown phytotoxicity in earlier studies. They demonstrated that harmaline is phytotoxic to adult A. thaliana plants at .
Morin2 [2-(2,4-dihydroxyphenyl)-3,5,7-trihydroxy-4H-1-benzopyran-4-one] is a flavonol and natural yellow dye that was isolated in 1895 by Arthur George Perkin* and Frank Pate at Yorkshire College (now the University of Leeds, UK) from the heartwood of the jack-fruit tree (Artocarpus integrifolia). The same year, the Perkin鈥揚ate group and Charles S. Boyer of Camden, NJ, isolated it from other trees, including old fustic (Maclura tinctoria).
Chemists synthesized morin as early as 1906; but its value in dyeing and electroplating鈥攁nd as a potential anticancer agent鈥攃alled for improved production methods. In April, Thomas Lindel and coauthors at the Technical University of Braunschweig and ORSATec (Bobigen, both in Germany) that does not require chromatographic separation of the product. Starting from phloroglucinol3 and 2,4-dimethoxybenzaldehyde4, they produced morin on a 40-g scale in 18% overall yield.
1. CAS Reg. No. 304-21-2.
2. CAS Reg. No. 480-16-0.
3. CAS Reg. No. 108-73-6.
4. CAS Reg. No. 613-45-6 .
Molecules from the Journals
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(卤)-贰辫颈肠丑濒辞谤辞丑测诲谤颈苍
fast facts
| CAS Reg. No. | 106-89-8 (racemic) |
| SciFinder nomenclature | Oxirane, 2-(chloromethyl)- |
| Empirical formula | C3H5ClO |
| Molar mass | 92.52 g/mol |
| Appearance | Colorless liquid |
| Boiling point | 118 掳C |
| Water solubility | 60 g/L (20 掳C) |
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