Benzyltriphenylphosphonium chloride
[CAS# 1100-88-5]

Identification

• Classification: Organic raw materials >> Organic phosphine compound
• Name: Benzyltriphenylphosphonium chloride
• Synonyms: BTPPC
• Molecular Formula: C₂₅H₂₂P.Cl
• Molecular Weight: 388.87
• CAS Registry Number: 1100-88-5
• EC Number: 214-154-3
• SMILES: C1=CC=C(C=C1)C[P+](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC=C4.[Cl-]

Properties

• Melting point: 330 °C (Expl.)
• Flash point: 300 °C (Expl.)
• Water solubility: SOLUBLE

Safety Data

• Hazard Symbols: GHS05;GHS06;GHS07;GHS08;GHS09 Danger
• Risk Statements: H300-H301-H310-H315-H318-H319-H330-H331-H335-H372-H400-H410
• Safety Statements: P260-P261-P262-P264-P264+P265-P270-P271-P273-P280-P284-P301+P316-P302+P352-P304+P340-P305+P351+P338-P305+P354+P338-P316-P317-P319-P320-P321-P330-P332+P317-P337+P317-P361+P364-P362+P364-P391-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	2	H300
Acute toxicity	Acute Tox.	2	H330
Specific target organ toxicity - single exposure	STOT SE	3	H335
Serious eye damage	Eye Dam.	1	H318
Specific target organ toxicity - repeated exposure	STOT RE	1	H372
Eye irritation	Eye Irrit.	2	H319
Acute toxicity	Acute Tox.	3	H311
Acute toxicity	Acute Tox.	3	H331
Acute hazardous to the aquatic environment	Aquatic Acute	1	H400
Chronic hazardous to the aquatic environment	Aquatic Chronic	1	H410
Acute toxicity	Acute Tox.	3	H301
Skin irritation	Skin Irrit.	2	H315
Chronic hazardous to the aquatic environment	Aquatic Chronic	2	H411
Acute toxicity	Acute Tox.	2	H310
Chronic hazardous to the aquatic environment	Aquatic Chronic	3	H412
Acute toxicity	Acute Tox.	1	H330
Acute toxicity	Acute Tox.	1	H300

• Transport Information: UN 2811

Discovery and Applications

Benzyltriphenylphosphonium chloride is an organic compound with the chemical formula C19H18ClP. It consists of a benzyl group (C6H5CH2) attached to a triphenylphosphonium cation (C6H5)3P+, along with a chloride anion (Cl−). This compound is typically synthesized by the reaction of triphenylphosphine with benzyl chloride in the presence of a base.

Benzyltriphenylphosphonium chloride is widely used in organic synthesis and catalysis. One of its key applications is in the Wittig reaction, a well-known method for the synthesis of alkenes from aldehydes or ketones. In this reaction, the phosphonium cation acts as a precursor to the phosphonium ylide, which reacts with carbonyl compounds to form alkenes. The Wittig reaction is a powerful tool for the creation of carbon-carbon double bonds, making benzyltriphenylphosphonium chloride an important reagent in the field of synthetic chemistry.

Additionally, benzyltriphenylphosphonium chloride is employed in other organic transformations that involve the formation of phosphonium ylides, which can be used in reactions such as the synthesis of epoxides, enones, and other valuable compounds. Its ability to generate phosphonium ylides makes it a versatile intermediate in many synthetic pathways.

Benzyltriphenylphosphonium chloride is also useful in the preparation of other phosphonium salts and as a reagent for the modification of various organic molecules. Due to its strong electrophilic nature, the compound can also be used in the synthesis of complex organic structures that require specific reactivity or functionalization of a carbon atom.

In summary, benzyltriphenylphosphonium chloride is a crucial reagent in organic chemistry, particularly for applications involving the Wittig reaction and the formation of phosphonium ylides. It is widely used in the synthesis of alkenes, epoxides, and other organic compounds, making it an important tool in the field of synthetic chemistry.

References

2017. Ionic salt (4-ethoxybenzyl)-triphenylphosphonium bromide as a green corrosion inhibitor on mild steel in acidic medium: experimental and theoretical evaluation. RSC Advances, 7(51).
DOI: 10.1039/C6RA27526E

1998. Flash vacuum pyrolysis of stabilised phosphorus ylides. Part 12. Extrusion of Ph3P from sulfonyl ylides and reactivity of the resulting sulfonyl carbenes. Journal of the Chemical Society, Perkin Transactions 1, (7).
DOI: 10.1039/A707948F

1997. Flash vacuum pyrolysis of stabilised phosphorus ylides. Part 10. Generation of 2-methylstyrylalkynes and their thermal cyclisation to 2-alkenylnaphthalenes. Journal of the Chemical Society, Perkin Transactions 1, (17).
DOI: 10.1039/A701427I