Article · Wikipedia archive · Last revised Jun 18, 2026

Hydroxymethyl group

The hydroxymethyl group is a substituent with the structural formula −CH2−OH. It consists of a methylene bridge bonded to a hydroxyl group. This makes the hydroxymethyl group a primary alcohol. It is a constitutional isomer of the methoxy group, differing only in the attachment site and orientation to the rest of the molecule. However, their chemical properties are different for an alcohol as opposed to an ether.

Last revised
Jun 18, 2026
Read time
≈ 1 min
Length
261 w
Citations
3
Source
Wikipedia ↗
Hydroxymethyl group
source ↗
Hydroxymethyl group covalently bonded to an R group
Names
IUPAC name
Hydroxymethyl group
Other names
Methanol radical
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=1S/CH3O/c1-2/h2H,1H2 ☒N
    Key: CBOIHMRHGLHBPB-UHFFFAOYSA-N ☒N
  • [CH2]O
Properties
−CH2OH
Molar mass 31.034 g·mol−1
Thermochemistry
−9 kJ/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

The hydroxymethyl group is a substituent with the structural formula −CH2−OH. It consists of a methylene bridge (−CH2− unit) bonded to a hydroxyl group (−OH). This makes the hydroxymethyl group a primary alcohol. It is a constitutional isomer of the methoxy group (−O−CH3), differing only in the attachment site and orientation to the rest of the molecule. However, their chemical properties are different for an alcohol as opposed to an ether.12

Hydroxymethyl is the side chain of encoded amino acid serine.3

References

References

  1. NAMING ORGANIC COMPOUNDS (PDF). p. 37. Archived from the original (PDF) on 2022-07-21. Retrieved 2022-08-08.
  2. Dong, Hao; Zheng, Erjin; Niu, Zhiyin; Zhang, Xiaoyu; Lin, Yi-Yu; Jain, Priyesh; Yu, Qiuming (2020-04-15). "Hydroxymethyl-Functionalized PEDOT-MeOH:PSS for Perovskite Solar Cells". ACS Applied Materials & Interfaces. 12 (15): 17571–17582. doi:10.1021/acsami.0c01756. ISSN 1944-8252. PMID 32204591. S2CID 214630308.
  3. Perczel, András; Farkas, Ödön; Csizmadia, Imre G. (1996-01-01). "Peptide Models. 18. Hydroxymethyl Side-Chain Induced Backbone Conformational Shifts of L-Serine Amide. All ab Initio Conformers of For L-Ser-NH2". Journal of the American Chemical Society. 118 (33): 7809–7817. doi:10.1021/ja960464q. ISSN 0002-7863.
External links