4-Biphenyl Carbinyl Bromide (CAS 1670-46-8) 97% White to Light Yellow Crystalline Solid | Benzylic Alkylating Reagent for Laboratory Synthesis

1. Product Overview

4-Biphenyl Carbinyl Bromide (CAS 1670-46-8), molecular formula C₁₃H₁₁Br, MW 247.13 g/mol, is a para-substituted benzylic bromide bearing a biphenyl scaffold. The reactive benzylic bromide undergoes SN2 displacement with amines, thiols, phenols, and carboxylates, making it a versatile alkylating agent for introducing the biphenylmethyl moiety in synthetic research and library construction.

2. Key Features and Benefits

• Reactive Benzylic Bromide: Readily displaced by N-, O-, S-nucleophiles under mild base (K₂CO₃, DIPEA) in aprotic solvents.

• Biphenyl Scaffold Introduction: Used to append a rigid biphenyl group in ligand design and SAR studies.

• Crystalline Solid: Easier to handle than volatile benzyl bromides; store cold and protected from light.

• High Purity: Supplied ≥97% (GC), suitable for multi-step synthesis.

3. Major Applications

• Organic Synthesis: Alkylating agent for N-alkylation of secondary amines, O-alkylation of phenols/alcohols, and S-alkylation of thiophenols.

• Medicinal Chemistry Research: Introduces biphenylmethyl pharmacophore into lead compounds via parallel synthesis.

• Material / Polymer Science: Used as a functional monomer precursor for biphenyl-containing architectures.

• Protecting Group Studies: Employed to install the 4-biphenylmethyl group on carboxylates or amines (cleavable by hydrogenolysis).

4. Technical Specifications

Item Description
Product Name 4-Biphenyl Carbinyl Bromide (4-(Bromomethyl)biphenyl)
Synonyms 4-Biphenylmethyl bromide; p-(Bromomethyl)biphenyl; (4-Biphenylyl)methyl bromide
CAS Number 1670-46-8
Molecular Formula C₁₃H₁₁Br
Molecular Weight 247.13 g/mol
Assay (Purity) ≥97% (GC)
Appearance White to light yellow crystalline solid (darkens on aging/light exposure)
Melting Point 102–106 °C
Boiling Point ~350–360 °C (Decomposes, Predicted)
Density ~1.38 g/cm³ (Predicted)
Calculated LogP ~4.2–4.6
Polar Surface Area (PSA) 0 Ų
Hydrogen Bond Donors 0
Hydrogen Bond Acceptors 0
Solubility Soluble in dichloromethane, ethyl acetate, toluene, and DMF; slowly hydrolyzes in aqueous media.
SMILES BrCc1ccc(c2ccccc2)cc1
InChI Key XZPQKJQJQYXSKW-UHFFFAOYSA-N
Storage 2–8 °C, sealed, under inert atmosphere (N₂/Ar), protect from light & moisture
HS Code 2903.69.90 / 3822.90.00

5. Storage and Handling

Store in a tightly sealed container at 2–8 °C, under inert atmosphere, protected from light and moisture. The benzylic bromide is moisture-sensitive (hydrolyzes to the corresponding benzyl alcohol) and may act as a lachrymator—handle in a fume hood. Dissolve in anhydrous dichloromethane, THF, or DMF immediately before use. Quench excess reagent with aqueous sodium sulfite or sodium bicarbonate prior to work-up.

6. Safety Summary

• GHS Classification: GHS05 (Corrosive) + GHS07 (Warning)

• Signal Word: Warning / Danger (per supplier SDS)

• Hazard Statements: H314 (Causes severe skin burns and eye damage), H315 (Skin irritation), H319 (Eye irritation), H335 (Respiratory irritation)

• Precautionary Statements: P260, P261, P264, P271, P280 (face shield + nitrile gloves + lab coat in fume hood), P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P310, P405, P501

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