Tert-butyl 2-(triphenyl-lambda5-phosphanylidene)acetate
C24H25O2P
tert-butyl 2-(triphenyl-lambda5-phosphanylidene)acetate
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Identification
- CAS Number
- 35000-38-5
- EC Number
- 412-880-7
- UN Number
- 3464
- Index Number
- 015-175-00-9
- PubChem CID
- 256127
Physical-chemical properties
- Molecular Formula
- C24H25O2P
- Molar Mass
- 376.40 g/mol
- IUPAC Name
- tert-butyl 2-(triphenyl-lambda5-phosphanylidene)acetate
Chemical Identifiers
- InChI
- InChI=1S/C24H25O2P/c1-24(2,3)26-23(25)19-27(20-13-7-4-8-14-20,21-15-9-5-10-16-21)22-17-11-6-12-18-22/h4-19H,1-3H3
- InChI Key
- ZWZUFQPXYVYAFO-UHFFFAOYSA-N
Overview
Tert-butyl 2-(triphenyl-lambda5-phosphanylidene)acetate (CAS 35000-38-5) is an organophosphorus compound with ylide functionality used primarily in organic synthesis applications. This specialized phosphorus ylide represents an important class of reagents in modern synthetic chemistry, characterized by its unique molecular structure featuring a triphenylphosphine group bonded to an acetate moiety. With the molecular formula C24H25O2P and a molecular weight of 376.4 g/mol, this compound exhibits the typical reactivity patterns associated with phosphorus ylides while offering enhanced stability through its tert-butyl ester protection. The compound presents significant safety considerations that require careful handling protocols. Classified under ADR Class 6.1 with a "Danger" signal word, it exhibits acute toxicity (Category 3), specific target organ toxicity following repeated exposure (Category 2), eye irritation potential, and skin sensitization properties. The GHS pictograms GHS06, GHS08, and GHS09 indicate its toxic, health hazard, and environmental hazard classifications respectively. Unlike some related organophosphorus compounds such as those derived from N-methylaniline systems, this ylide maintains relatively predictable reactivity patterns under controlled conditions. Primary industrial applications include its use as a key intermediate in pharmaceutical synthesis, particularly in Wittig-type reactions for carbon-carbon bond formation. The compound serves as an effective reagent in the preparation of α,β-unsaturated esters and plays a crucial role in the synthesis of complex organic molecules requiring precise stereochemical control. Additionally, it finds application in fine chemical manufacturing where selective olefination reactions are required. OYSI maintains reliable supply chains for tert-butyl 2-(triphenyl-lambda5-phosphanylidene)acetate, supporting European customers with technical-grade material suitable for research and industrial applications.
Safety & Classification
Acute Tox. 3 *; STOT RE 2 *; Eye Irrit. 2; Skin Sens. 1; Aquatic Chronic 2
GHS Pictograms
HHazard Statements (H-Statements)
Describe the nature and severity of the hazard
Classification according to CLP Regulation (EC) No 1272/2008. The complete list of hazard and precautionary statements can be found in the Safety Data Sheet (SDS).
First Aid Measures
Skin Contact
Measures if substance contacts the skin
First Aid Actions
- +P302IF ON SKIN:
- +P352Wash with plenty of water.
- +P361Take off immediately all contaminated clothing.
- +P313Get medical advice/attention.
Related hazard statements:
Eye Contact
Measures if substance gets into the eyes
First Aid Actions
- +P305IF IN EYES:
- +P351Rinse cautiously with water for several minutes.
- +P338Remove contact lenses, if present and easy to do. Continue rinsing.
- +P313Get medical advice/attention.
Related hazard statements:
Ingestion
Measures if substance is accidentally swallowed
First Aid Actions
- +P301IF SWALLOWED:
- +P330Rinse mouth.
- +P331Do NOT induce vomiting.
- +P310Immediately call a POISON CENTER/doctor.
Related hazard statements:
General Measures
Emergency 112 | Poison Control: +49 30 19240 (DE), +33 1 45 42 59 59 (FR), +31 30 274 88 88 (NL)
First aid measures are based on CLP classification and associated P-statements. They do not replace the Safety Data Sheet (SDS). In case of emergency, always consult the full SDS and a physician.
Transport (ADR)
| UN Number | 3464 |
| ADR Class | 6.1 |
| Packing Group | II |
| Tunnel Code | D/E |
| Proper Shipping Name | tert-Butyl-(triphenylphosphoranyliden)acetat |
| Marine Pollutant | No |
Frequently Asked Questions
What is tert-butyl 2-(triphenyl-lambda5-phosphanylidene)acetate?
Tert-butyl 2-(triphenyl-lambda5-phosphanylidene)acetate is an organophosphorus compound with the molecular formula C24H25O2P and CAS number 35000-38-5. This chemical substance has a molecular weight of 376.4 g/mol and belongs to the class of phosphonium ylides. It is classified as a dangerous substance requiring careful handling due to its acute toxicity and potential for causing specific target organ toxicity through repeated exposure.
What are the physicochemical properties of tert-butyl 2-(triphenyl-lambda5-phosphanylidene)acetate?
Tert-butyl 2-(triphenyl-lambda5-phosphanylidene)acetate is a solid organophosphorus compound at room temperature with a molecular weight of 376.4 g/mol. The substance contains both aromatic triphenylphosphine groups and aliphatic tert-butyl ester functionality. Its exact physical appearance, solubility, and stability characteristics should be confirmed through technical specifications, as these properties can vary depending on purity and crystalline form.
What is tert-butyl 2-(triphenyl-lambda5-phosphanylidene)acetate used for?
Tert-butyl 2-(triphenyl-lambda5-phosphanylidene)acetate is primarily used as a reagent in organic synthesis, particularly in Wittig-type reactions for carbon-carbon bond formation. This phosphonium ylide serves as an important intermediate in pharmaceutical and fine chemical manufacturing. It enables the formation of alkenes through reaction with carbonyl compounds, making it valuable in the synthesis of complex organic molecules in research and industrial applications.
How to handle tert-butyl 2-(triphenyl-lambda5-phosphanylidene)acetate safely?
Tert-butyl 2-(triphenyl-lambda5-phosphanylidene)acetate requires careful handling due to its Acute Tox. 3 classification and skin sensitization potential. Essential safety measures include wearing appropriate personal protective equipment such as chemical-resistant gloves, safety goggles, and protective clothing. Work should be conducted in well-ventilated areas or under fume hoods to prevent inhalation exposure. Avoid skin and eye contact, and ensure personnel are trained in proper handling procedures for toxic substances.
How to store tert-butyl 2-(triphenyl-lambda5-phosphanylidene)acetate correctly?
Tert-butyl 2-(triphenyl-lambda5-phosphanylidene)acetate should be stored in tightly sealed containers in a cool, dry, and well-ventilated area away from heat sources and incompatible materials. The storage area must be secure and accessible only to authorized personnel due to its toxic classification. Containers should be properly labeled with hazard information, and storage conditions should prevent degradation while minimizing exposure risks to personnel and the environment.
What to do in case of contact with tert-butyl 2-(triphenyl-lambda5-phosphanylidene)acetate?
In case of skin contact with tert-butyl 2-(triphenyl-lambda5-phosphanylidene)acetate, immediately remove contaminated clothing and wash the affected area thoroughly with soap and water for at least 15 minutes. For eye contact, rinse immediately with plenty of clean water for 15 minutes and seek medical attention. If inhaled, move the person to fresh air and seek medical advice if symptoms persist. Always consult safety data sheets for complete first aid procedures.
How to dispose of tert-butyl 2-(triphenyl-lambda5-phosphanylidene)acetate properly?
Tert-butyl 2-(triphenyl-lambda5-phosphanylidene)acetate must be disposed of according to local, national, and international regulations for hazardous waste. This toxic substance cannot be disposed of with regular waste and requires specialized hazardous waste treatment facilities. Contact licensed waste disposal companies experienced in handling organophosphorus compounds. Ensure all containers are properly labeled and documented for waste tracking compliance with environmental regulations.
How to transport tert-butyl 2-(triphenyl-lambda5-phosphanylidene)acetate?
Tert-butyl 2-(triphenyl-lambda5-phosphanylidene)acetate is classified under ADR Class 6.1 (toxic substances), Packing Group II, indicating significant toxicity requiring special transport precautions. Transportation must comply with dangerous goods regulations including proper packaging, labeling with appropriate hazard pictogrammes (GHS06, GHS08, GHS09), and documentation. Only certified carriers authorized to transport Class 6.1 substances should handle shipments, following all applicable ADR transport requirements.
Is tert-butyl 2-(triphenyl-lambda5-phosphanylidene)acetate subject to specific regulations?
Tert-butyl 2-(triphenyl-lambda5-phosphanylidene)acetate is subject to REACH registration requirements and CLP classification regulations in Europe. The substance is classified with hazard classes including Acute Tox. 3, STOT RE 2, Eye Irrit. 2, Skin Sens. 1, and Aquatic Chronic 2, requiring compliance with corresponding labeling and safety requirements. While not currently listed as an SVHC, users must comply with all applicable chemical safety legislation and workplace exposure limits.
Where to buy tert-butyl 2-(triphenyl-lambda5-phosphanylidene)acetate in Europe?
Tert-butyl 2-(triphenyl-lambda5-phosphanylidene)acetate is available through OYSI, a specialized European distributor of chemical products with expertise in organophosphorus compounds. OYSI provides reliable supply chains across Europe with proper documentation, safety data sheets, and regulatory compliance support. As an established chemical distributor, OYSI ensures quality products meeting European standards while providing technical support for safe handling and application of this specialized reagent.
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Tert-butyl 2-(triphenyl-lambda5-phosphanylidene)acetate is a dangerous good. We support you with labeling, packaging, and transport documentation.
Data Sources
Classification per CLP Regulation (EC) No 1272/2008. Data from ECHA and PubChem.