CAS Number: 2767-70-6
Chemical Name: (4-Nitrobenzyl)triphenylphosphonium bromide
IUPAC Name: (4-Nitrobenzyl)triphenylphosphanium bromide
Synonyms:
p-Nitrobenzyltriphenylphosphonium bromide;
4-Nitrobenzyltriphenylphosphonium bromide;
(4-Nitrophenylmethyl)triphenylphosphonium bromide
Molecular Formula: C₂₅H₂₁BrNO₂P
Molecular Weight: ~478.32 g/mol
Appearance: Yellow to pale orange crystalline powder
Physical State: Solid
Melting Point: Typically reported in the range of 250–260 °C (may vary depending on purity)
Boiling Point: Not applicable (decomposes before boiling)
Solubility:
Soluble in polar organic solvents such as methanol, ethanol, acetonitrile, and DMSO; limited solubility in water
Stability:
Stable under standard laboratory conditions; sensitive to strong oxidizing agents and excessive moisture
Functional Groups:
Quaternary phosphonium group (–P⁺(C₆H₅)₃)
Nitro group (–NO₂)
Aromatic benzene rings
Benzyl linkage
Chemical Class:
Quaternary phosphonium salt / Organophosphorus compound
SMILES (representative):
[Br-].O=N+C1=CC=C(C=C1)CP+(C3=CC=CC=C3)C4=CC=CC=C4
InChI Key (representative):
(Varies by database; available from chemical registries)
2767-70-6 is widely used as a precursor in the preparation of Wittig reagents, which are essential in organic synthesis for:
Carbon–carbon double bond formation
Alkene synthesis
Stereoselective organic transformations
The phosphonium salt can be converted into a corresponding ylide, enabling key reactions in synthetic chemistry.
Used in the synthesis of advanced pharmaceutical intermediates
Building block for biologically active molecules
Intermediate in specialty chemical manufacturing
Its phosphonium functionality makes it particularly valuable in constructing complex molecular frameworks.
Commonly employed in:
Academic organic chemistry laboratories
Medicinal chemistry research
Development of novel synthetic methodologies
Structure–activity relationship (SAR) studies
The presence of both nitro and phosphonium groups enhances its versatility for multi-step synthesis.
GHS Classification (typical for similar compounds):
Harmful if swallowed
Causes skin and eye irritation
May cause respiratory irritation
Common Hazard Statements:
H302: Harmful if swallowed
H315: Causes skin irritation
H319: Causes serious eye irritation
H335: May cause respiratory irritation
Precautionary Statements:
P261: Avoid breathing dust
P280: Wear protective gloves and eye protection
P305 + P351 + P338: IF IN EYES, rinse cautiously with water and remove contact lenses
P301 + P312: IF SWALLOWED, call a doctor if you feel unwell
Handle in a well-ventilated area using appropriate personal protective equipment (PPE).
Typical Purity: 97–99% (Research and Industrial Grade)
Storage Conditions:
Store in a tightly sealed container
Keep in a cool, dry, and well-ventilated area
Protect from moisture and direct sunlight
Keep away from strong oxidizing agents
Commercial Use:
Available from specialty chemical manufacturers for research and industrial organic synthesis applications.
Not intended for direct pharmaceutical, food, or diagnostic use without proper regulatory compliance.
2767-70-6 ((4-NITROBENZYL)TRIPHENYLPHOSPHONIUM BROMIDE) is an important quaternary phosphonium salt widely utilized in organic synthesis, particularly in Wittig reactions for carbon–carbon bond formation. Its unique combination of phosphonium and nitro functional groups makes it a valuable intermediate in pharmaceutical, fine chemical, and advanced research applications.
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