Methyl 4-(Chloromethyl)benzoate (CAS 58438-03-2) 97% White to Off-White Crystalline Solid | ω-Haloalkyl Aryl Ester / Alkylating Reagent for Laborato

1. Product Overview

Methyl 4-(chloromethyl)benzoate (CAS 58438-03-2) has molecular formula C₉H₉ClO₂ and MW 184.62 g/mol. It consists of a para-substituted benzoate ester bearing a benzylic chloromethyl group. The ester is stable to mild base, while the benzylic chloride undergoes SN2 displacement with amines, thiols, phenols, and carboxylates to introduce the 4-(methoxycarbonyl)phenylmethyl moiety. The methyl ester can be saponified to the corresponding benzoic acid after alkylation if desired.

2. Key Features and Benefits

• Reactive Benzylic Chloride: Displaced by N/O/S-nucleophiles under mild base (K₂CO₃, DIPEA, NaH) in DMF/DCM/MeCN.

• Ester Handle: Methoxycarbonyl group tolerates SN2 conditions; hydrolyzable to COOH with NaOH/MeOH–H₂O.

• Crystalline Solid: Easier to handle than volatile benzyl chlorides; store cold and dry.

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

3. Major Applications

• Organic Synthesis: Alkylating agent for N-alkylation of secondary amines, O-alkylation of phenols/alcohols, and S-alkylation of thiophenols → 4-(methoxycarbonyl)benzyl derivatives.

• Heterocycle Synthesis: Cyclization with diamines → substituted isoindolinones or benzazepines (methodology studies).

• Protecting Group / Linker Research: Installs a UV-active, ester-terminated benzyl group cleavable by saponification.

• Library / SAR Studies: Introduces 4-CO₂Me–benzyl pharmacophore mimetic in lead-like molecules.

• Analytical Reference: Standard for GC/HPLC method development in halogenated ester impurity profiling.

4. Technical Specifications

Item Description
Product Name Methyl 4-(Chloromethyl)benzoate
Synonyms Methyl p-(chloromethyl)benzoate; 4-(Chloromethyl)benzoic acid methyl ester
CAS Number 58438-03-2
Molecular Formula C₉H₉ClO₂
Molecular Weight 184.62 g/mol
MDL Number MFCD00017243
PubChem CID 2724335
Assay (Purity) ≥97% (GC)
Appearance White to off-white crystalline solid (may darken slightly on aging)
Melting Point 63–67 °C
Boiling Point ~298–302 °C (Estimated; decomposes)
Density ~1.23 g/cm³ (Estimated)
Calculated LogP ~2.0–2.5
Polar Surface Area (PSA) 26.3 Ų
Hydrogen Bond Donors 0
Hydrogen Bond Acceptors 2 (C=O ester ×2)
Rotatable Bonds 3
Solubility Soluble in DCM, THF, DMF, ethyl acetate, acetone  warm methanol; poorly soluble in water, hexane.
SMILES COC(=O)c1ccc(CCl)cc1
InChI Key INCHIKEY (PubChem): HQPMXYERegfWNB-UHFFFAOYSA-N — verify via database
Storage 2–8 °C, sealed, protect from light & moisture; moisture-sensitive (slow hydrolysis to alcohol). Handle in fume hood—benzylic Cl may be lachrymatory in vapor.
HS Code 2916.90.90 / 3822.90.00

5. Storage and Handling

Store in a tightly sealed container at 2–8 °C, protected from light and moisture. The benzylic chloride is moisture-sensitive (hydrolyzes to the corresponding 4-hydroxymethyl benzoate) and may be mildly lachrymatory—weigh in fume hood. Dissolve in anhydrous DCM, THF, or DMF immediately before use. Quench excess with aqueous Na₂SO₃ or NaHCO₃ prior to work-up. For ester hydrolysis: 1–2 M NaOH in MeOH–H₂O, rt to 40 °C, 1–3 h, then acidify.

6. Safety Summary

• GHS Classification: GHS05 (Corrosive/Irritant) + GHS07 – Warning

• Signal Word: Warning / Danger (per conc.)

• Hazard Statements: H315 (Causes skin irritation), H319 (Causes serious eye irritation), H335 (May cause respiratory irritation); H301 (Harmful if swallowed—some SDS label)

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