Hydroxymethyl group

{{Chembox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 386006473

| OtherNames = Methanol radical

| IUPACName = Hydroxymethyl group

| ImageFile = Hydroxymethyl group skeletal.svg

| ImageSize = 200px

| ImageCaption = Hydroxymethyl group covalently bonded to an R group

| Section1 = {{Chembox Identifiers

| CASNo_Ref = {{cascite|correct|??}}

| CASNo = 2597-43-5

| PubChem = 137654

| ChemSpiderID = 121313

| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}

| SMILES = [CH2]O

| StdInChI = 1S/CH3O/c1-2/h2H,1H2

| StdInChI_Ref = {{stdinchicite|changed|chemspider}}

| StdInChIKey = CBOIHMRHGLHBPB-UHFFFAOYSA-N

| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}

}}

| Section2 = {{Chembox Properties

| Formula = {{chem2|\sCH2OH}}

| C=1|H=3|O=1

}}

| Section3 = {{Chembox Thermochemistry

| DeltaHf = −9 kJ/mol

}}

}}

The hydroxymethyl group is a substituent with the structural formula {{chem2|\sCH2\sOH}}. It consists of a methylene bridge ({{chem2|\sCH2\s}} unit) bonded to a hydroxyl group ({{chem2|\sOH}}). This makes the hydroxymethyl group an alcohol. It has the identical chemical formula with the methoxy group ({{chem2|\sO\sCH3}}) that differs only in the attachment site and orientation to the rest of the molecule. However, their chemical properties are different.{{Cite book |title=NAMING ORGANIC COMPOUNDS |url=https://www.kpu.ca/sites/default/files/downloads/sup08.pdf |url-status=dead |page=37 |archive-url=https://web.archive.org/web/20220721055000/https://www.kpu.ca/sites/default/files/downloads/sup08.pdf |archive-date=2022-07-21 |access-date=2022-08-08}}{{Cite journal |last1=Dong |first1=Hao |last2=Zheng |first2=Erjin |last3=Niu |first3=Zhiyin |last4=Zhang |first4=Xiaoyu |last5=Lin |first5=Yi-Yu |last6=Jain |first6=Priyesh |last7=Yu |first7=Qiuming |date=2020-04-15 |title=Hydroxymethyl-Functionalized PEDOT-MeOH:PSS for Perovskite Solar Cells |url=https://pubmed.ncbi.nlm.nih.gov/32204591/ |url-status=live |journal=ACS Applied Materials & Interfaces |volume=12 |issue=15 |pages=17571–17582 |doi=10.1021/acsami.0c01756 |issn=1944-8252 |pmid=32204591 |s2cid=214630308 |archive-url=https://web.archive.org/web/20220808221741/https://pubmed.ncbi.nlm.nih.gov/32204591/ |archive-date=2022-08-08 |access-date=2022-08-08}}

Hydroxymethyl is the side chain of encoded amino acid serine.{{Cite journal |last1=Perczel |first1=András |last2=Farkas |first2=Ödön |last3=Csizmadia |first3=Imre G. |date=1996-01-01 |title=Peptide Models. 18. Hydroxymethyl Side-Chain Induced Backbone Conformational Shifts of l -Serine Amide. All ab Initio Conformers of For- l -Ser-NH 2 |url=https://pubs.acs.org/doi/10.1021/ja960464q |url-status=live |journal=Journal of the American Chemical Society |language=en |volume=118 |issue=33 |pages=7809–7817 |doi=10.1021/ja960464q |issn=0002-7863 |archive-url=https://web.archive.org/web/20220808210908/https://pubs.acs.org/doi/10.1021/ja960464q |archive-date=2022-08-08 |access-date=2022-08-08|url-access=subscription }}