4-(hydroxymethyl)benzoic acid

• ChemBase ID: 67379
• Molecular Formular: C8H8O3
• Molecular Mass: 152.14732
• Monoisotopic Mass: 152.04734412
• SMILES: C(=O)(c1ccc(cc1)CO)O
• Canonical SMILES: OCc1ccc(cc1)C(=O)O
• InChI: InChI=1S/C8H8O3/c9-5-6-1-3-7(4-2-6)8(10)11/h1-4,9H,5H2,(H,10,11)
• InChIKey: WWYFPDXEIFBNKE-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-(hydroxymethyl)benzoic acid
• IUPAC Traditional name: p-hydroxymethyl benzoic acid
• Synonyms: 4-(Hydroxymethyl)benzoic acid; 4-HYDROXYMETHYLBENZOIC ACID; 4-(Hydroxymethyl)benzoic acid; 4-Carboxybenzyl alcohol; HB Linker; 4-羟甲基苯甲酸; 4-(羟基甲基)苯甲酸

Database IDs

• CAS Number: 96937-45-0; 3006-96-0
• MDL Number: MFCD00017598
• Beilstein Number: 2690023
• PubChem SID: 24863906; 162033114; 24895717; 24879526
• PubChem CID: 76360

CALCULATED PROPERTIES

• Acid pKa: 4.0631037
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): -0.58552027
• LogD (pH = 7.4): -2.2582858
• Log P: 0.86347896
• Molar Refractivity: 40.1301 cm^3
• Polarizability: 15.133807 Å^3
• Polar Surface Area: 57.53 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 179-183°C; 182-185 °C; 182-185 °C(lit.)

Safety Information

• Storage Condition: 0°C
• Storage Warning: IRRITANT
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36; 26-37
• TSCA Listed: false; 否
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338; P280G-P305+P351+P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98.0% (T); 95+%; 98%; 98+%; 99%
• Grade: purum
• Linear Formula: HOCH2C6H4CO2H

DETAILS

Sigma Aldrich - 382639

Packaging
1, 10 g in glass bottle

Sigma Aldrich - 55616

Other Notes
Linkage reagent for polyamide solid phase peptide synthesis1,2

REFERENCES

• Linker for solid-phase peptide synthesis, stable to TFA but cleaved by nucleophiles: J. Chem. Soc., Perkin 1, 538 (1981).