(4-methoxyphenyl)methanol

• ChemBase ID: 78360
• Molecular Formular: C8H10O2
• Molecular Mass: 138.1638
• Monoisotopic Mass: 138.06807956
• SMILES: O(c1ccc(cc1)CO)C
• Canonical SMILES: OCc1ccc(cc1)OC
• InChI: InChI=1S/C8H10O2/c1-10-8-4-2-7(6-9)3-5-8/h2-5,9H,6H2,1H3
• InChIKey: MSHFRERJPWKJFX-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4-methoxyphenyl)methanol
• IUPAC Traditional name: P-methoxybenzyl alcohol
• Synonyms: (4-methoxyphenyl)methanol; ANISYL ALCOHOL; Anisyl alcohol; p-Anisyl alcohol; 4-Methoxybenzyl alcohol 98%; 4-Methoxybenzyl alcohol; 4-Methoxybenzyl alcohol; Anis alcohol; Anise alcohol; p-ANISYL ALCOHOL; 4-Methoxyphenylmethanol; 4-甲氧基苄醇; 对甲氧基苄醇; 对甲氧基苄醇; 对茴香醇; 茴香醇; 4-甲氧基苄醇

Database IDs

• CAS Number: 105-13-5
• EC Number: 203-273-6
• MDL Number: MFCD00004653
• Beilstein Number: 636654
• Merck Index: 14604
• PubChem SID: 24900860; 24900859; 162043129; 24848301; 24883578
• PubChem CID: 7738
• FEMA ID: 2099
• Council of Europe Number: 66
• Flavis Number: 2.128

CALCULATED PROPERTIES

• Acid pKa: 15.022862
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 1.0482248
• LogD (pH = 7.4): 1.0482248
• Log P: 1.0482248
• Molar Refractivity: 39.3371 cm^3
• Polarizability: 15.297958 Å^3
• Polar Surface Area: 29.46 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 22-25 °C(lit.); 22-25°C; 22-25°C
• Boiling Point: 258-260°C; 259 °C(lit.); 259°C
• Flash Point: 110°C; 113 °C; 113°C(235°F); 235.4 °F
• Density: 1.108; 1.110; 1.113 g/mL at 25 °C(lit.)
• Refractive Index: 1.5450; n20/D 1.544(lit.)
• Organoleptic: caramel; chocolate; hyacinth; floral; fruity; sweet; vanilla; honey; floral; sweet; vanilla

Safety Information

• Storage Warning: Harmful/Irritant/Corrosive
• RTECS: DO8925000
• European Hazard Symbols: X; Harmful (Xn)
• German water hazard class: 1; 3
• Risk Statements: 22-36/37/38; R:22
• Safety Statements: 26-36; 26-36/37; S:36/37/39
• TSCA Listed: 是
• GHS Pictograms: GHS06; GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H301-H315-H319-H335; H302-H315-H319-H335
• GHS Precautionary statements: P261-P301+P310-P305+P351+P338-P302+P352-P405-P501A; P261-P305 + P351 + P338
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• Regulation Compliance: EU Regulation 1334/2008 & 178/2002; FCC; FDA 21 CFR (172.515)

Pharmacology Properties

• Allergens: no known allergens

Product Information

• Purity: ≥98%; ≥98.0% (GC); 98%
• Grade: FG; Halal; Kosher; natural; NI; purum
• Linear Formula: CH3OC6H4CH2OH
• Classification: Genuine Natural Compounds

DETAILS

MP Biomedicals - 02150381

Used for preparation of p-methoxy-benzyl-protected amino acids

MP Biomedicals - 05210707

MP Biomedicals Rare Chemical collection

Sigma Aldrich - W209910

General description
Natural Occurrence: Anise, honey, bourbon, vanilla.
Packaging
1 kg in glass bottle
1 sample in glass bottle
100 g in glass bottle
5 kg in poly drum

Sigma Aldrich - W209902

Packaging
1 kg in glass bottle
1 sample in glass bottle
10, 25 kg in poly drum

Sigma Aldrich - 136905

Packaging
5, 100, 500 g in glass bottle

Sigma Aldrich - 64840

Other Notes
Provides temporary protection of the anomeric OH-group in carbohydrates1

REFERENCES

• Carboxyl protection agent giving the 4-methoxybenzyl (PMB; 4-methoxyphenylmethyl; MPM) ester, e.g. by reaction with the 4-nitrophenyl ester. The group is stable to 0.5N HCl in MeOH which readily cleaves Boc groups, but can be removed by TFA, leaving Cbz-groups unaffected: Austr. J. Chem., 21, 2543 (1968). For cleavage using AcOH at 90^o, see: Synth. Commun., 24, 1151 (1994). For cleavage with Cerium(III) chloride heptahydrate, A12947, in the presence of NaI, see: J. Org. Chem., 64, 5696 (1999). See Appendix 6.
• Has also been used, in the presence of TFA, to protect thiols: Tetrahedron Lett., 35, 1631 (1994). Cleavage is by refluxing with TFA: Bull. Chem. Soc. Jpn., 37, 433 (1964); Bioorg. Chem. Med. Lett., 3, 739 (1993), or Hg(II) salts: Chem. Pharm. Bull., 26, 1576 (1978); J. Med. Chem., 31, 2199 (1988); J. Org. Chem., 52, 4420 (1987).