Editing Formaldehyde (section)

{{short description|Organic compound (H–CHO); simplest aldehyde}}
{{Redirect-distinguish|Methanal|Methanol|Menthol}}
{{other uses}}
{{Chembox
| Watchedfields = changed
| verifiedrevid = 464368486
| Name = 
| ImageFile = 
| ImageFileL1 = Structural formula of formaldehyde.svg
| ImageClassL1 = skin-invert-image
| ImageFileL1_Ref = {{chemboximage|correct|??}}
| ImageNameL1 = Structural formula of formaldehyde (with hydrogens)
| ImageFileR1 = Formaldehyde-3D-vdW.png
| ImageClassR1 = bg-transparent
| ImageFileR1_Ref = {{chemboximage|correct|??}}
| ImageNameR1 = Spacefill model of formaldehyde
| ImageFile2 = Formaldehyde-3D-balls-A.png
| ImageClass2 = bg-transparent
| ImageFile2_Ref = {{chemboximage|correct|??}}
| ImageSize2 = 121
| ImageName2 = Ball and stick model of formaldehyde
| PIN = Formaldehyde<ref name=iupac2013>{{cite book | title = Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013 (Blue Book) | publisher = [[Royal Society of Chemistry]] | date = 2014 | location = Cambridge | page = 908 | doi = 10.1039/9781849733069-FP001 | isbn = 978-0-85404-182-4| chapter = Front Matter}}</ref>
| SystematicName = Methanal<ref name=iupac2013/>
| OtherNames = {{Unbulleted list|Methyl aldehyde|[[Methylene glycol]] (diol forms in aqueous solution)|Methylene oxide|Formalin (aqueous solution)|Formol|Carbonyl hydride|Methanone|Oxomethane}}
| IUPACName = 
| Section1 = {{Chembox Identifiers
| IUPHAR_ligand = 4196
| CASNo=50-00-0
| CASNo_Ref = {{cascite|correct|CAS}}
| PubChem=712
| ChemSpiderID=692
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| UNII=1HG84L3525
| UNII_Ref = {{fdacite|correct|FDA}}
| EINECS=200-001-8
| UNNumber=2209
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank=DB03843
| KEGG=D00017
| KEGG_Ref = {{keggcite|correct|kegg}}
| MeSHName=Formaldehyde
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI=16842
| ChEMBL=1255
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| RTECS=LP8925000
| Beilstein=1209228
| Gmelin=445
| 3DMet=B00018
| SMILES=C=O
| StdInChI=1S/CH2O/c1-2/h1H2
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| InChI=1/CH2O/c1-2/h1H2
| StdInChIKey=WSFSSNUMVMOOMR-UHFFFAOYSA-N
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| InChIKey=WSFSSNUMVMOOMR-UHFFFAOYAT
}}
| Section2 = {{Chembox Properties
| Properties_ref =<ref>{{RubberBible62nd|pages=C–301, E–61}}</ref>
| C=1 | H=2 | O=1
| Appearance=Colorless gas
| Density=0.8153 g/cm<sup>3</sup> (−20&nbsp;°C)<ref name=ipcs>{{cite web | title = SIDS Initial Assessment Report | url = http://www.inchem.org/documents/sids/sids/FORMALDEHYDE.pdf | publisher = International Programme on Chemical Safety | access-date = 2019-04-21 | archive-url = https://web.archive.org/web/20190328010406/http://www.inchem.org/documents/sids/sids/FORMALDEHYDE.pdf | archive-date = 2019-03-28 | url-status = dead}}</ref> (liquid)
| MeltingPtC=-92
| BoilingPtC=-19
| BoilingPt_ref = <ref name=ipcs/>
| pKa = 13.27 (hydrate)<ref>
{{cite web | url = https://pubchem.ncbi.nlm.nih.gov/compound/formaldehyde#section=Odor-Threshold | title = PubChem Compound Database; CID=712 | publisher = National Center for Biotechnology Information | access-date = 2017-07-08 | archive-url = https://web.archive.org/web/20190412235321/https://pubchem.ncbi.nlm.nih.gov/compound/formaldehyde#section=Odor-Threshold | archive-date = 2019-04-12 | url-status = live}}</ref><ref>{{cite web | title = Acidity of aldehydes | url = http://chemistry.stackexchange.com/questions/12232/acidity-of-aldehydes | publisher = Chemistry Stack Exchange | access-date = 2019-04-21 | archive-url = https://web.archive.org/web/20180901112531/https://chemistry.stackexchange.com/questions/12232/acidity-of-aldehydes | archive-date = 2018-09-01 | url-status = dead}}</ref>
| Solubility=400 g/L
| LogP=0.350
| Dipole= 2.330 D<ref>{{cite web | last1 = Nelson | first1 = R. D. Jr. | last2 = Lide | first2 = D. R. | last3 = Maryott | first3 = A. A. | year = 1967 | title = Selected Values of electric dipole moments for molecules in the gas phase (NSRDS-NBS10) | url = https://nvlpubs.nist.gov/nistpubs/Legacy/NSRDS/nbsnsrds10.pdf | access-date = 2019-04-21 | archive-url = https://web.archive.org/web/20180608004619/https://nvlpubs.nist.gov/nistpubs/Legacy/NSRDS/nbsnsrds10.pdf | archive-date = 2018-06-08 | url-status = live}}</ref>
| VaporPressure = > 1 atm<ref>{{cite journal | last1 = Spence | first1 = Robert | last2 = Wild | first2 = William | year = 1935 | title = 114. The vapour-pressure curve of formaldehyde, and some related data | journal = Journal of the Chemical Society (Resumed) | pages = 506–509 | doi = 10.1039/jr9350000506}}</ref>
| MagSus = −18.6·10<sup>−6</sup> cm<sup>3</sup>/mol
}}
| Section3 = {{Chembox Structure
| MolShape=Trigonal planar
| PointGroup = C<sub>2v</sub>
}}
| Section4 = {{Chembox Thermochemistry
| Thermochemistry_ref = <ref name="CRC97">{{Cite book |url=https://www.worldcat.org/oclc/930681942 |title=CRC handbook of chemistry and physics: a ready-reference book of chemical and physical data. |date=2016 |others=William M. Haynes, David R. Lide, Thomas J. Bruno |isbn=978-1-4987-5428-6 |edition=2016-2017, 97th |location=Boca Raton, Florida |oclc=930681942 |access-date=2022-04-12 |archive-date=2022-05-04 |archive-url=https://web.archive.org/web/20220504220656/https://www.worldcat.org/title/crc-handbook-of-chemistry-and-physics-a-ready-reference-book-of-chemical-and-physical-data/oclc/930681942 |url-status=live}}</ref>
| HeatCapacity = 35.387&nbsp;J·mol<sup>−1</sup>·K<sup>−1</sup>
| Entropy = 218.760&nbsp;J·mol<sup>−1</sup>·K<sup>−1</sup>
| DeltaHform = −108.700&nbsp;kJ·mol<sup>−1</sup>
| DeltaGfree = −102.667&nbsp;kJ·mol<sup>−1</sup>
| DeltaHcombust = 571&nbsp;kJ·mol<sup>−1</sup>
 }}
| Section5 = 
| Section6 = {{Chembox Pharmacology
| ATCvet = yes
| ATCCode_prefix = P53
| ATCCode_suffix = AX19
}}
| Section7 = {{Chembox Hazards
| ExternalSDS =[https://www.fishersci.com/shop/msdsproxy?productName=F75P1GAL&productDescription=formaldehyde--by-weight-histological-fisher-chemical&catNo=F75P-1GAL&vendorId=VN00000001&storeId=10652 MSDS]([https://web.archive.org/web/20170918021414/https://www.fishersci.com/shop/msdsproxy?productName=F75P1GAL&productDescription=formaldehyde--by-weight-histological-fisher-chemical&catNo=F75P-1GAL&vendorId=VN00000001&storeId=10652 Archived])
| GHSPictograms = {{GHS06}}{{GHS05}}{{GHS08}}<ref name="GESTIS">{{GESTIS|ZVG=10520 |CAS=50-00-0 |Name=Formaldehyde |Date=13 March 2020}}</ref>
| GHSSignalWord = '''Danger'''
| HPhrases = {{H-phrases|301+311+331|314|317|335|341|350|370}}<ref name=GESTIS/>
| PPhrases = {{P-phrases|201|280|303+361+353|304+340+310|305+351+338|308+310}}<ref name=GESTIS/>
| NFPA-H=4
| NFPA-F=4 <!-- as gas; common aqueous solution (37%) is only F=2 -->
| NFPA-R=0
| NFPA-S=COR
| FlashPtC = 64
| AutoignitionPtC = 430
| ExploLimits =7–73%
| LD50=100 mg/kg (oral, rat)<ref>{{cite web | title = Substance Name: Formaldehyde [USP] | url = https://chem.nlm.nih.gov/chemidplus/rn/50-00-0 | website= ChemlDplus|publisher= US National Library of Medicine | archive-url = https://web.archive.org/web/20170918063725/https://chem.nlm.nih.gov/chemidplus/rn/50-00-0 | archive-date = 2017-09-18 | url-status=live}}</ref>
| PEL = TWA 0.75 ppm ST 2 ppm (as formaldehyde and formalin)<ref name=PGCH>{{PGCH|0293}}</ref><ref>{{PGCH|0294}}</ref>
| IDLH = Ca [20 ppm]<ref name=PGCH/>
| REL = Ca TWA 0.016 ppm C 0.1 ppm [15-minute]<ref name=PGCH/>
| LC50 = 333 ppm (mouse, 2&nbsp;[[hour|h]])<br />815 ppm (rat, 30&nbsp;min)<ref name=IDLH>{{IDLH|50000|Formaldehyde}}</ref>
| LCLo = 333 ppm (cat, 2&nbsp;[[hour|h]])<ref name=IDLH/>
}}
| Section8 = {{Chembox Related
| OtherFunction_label =[[aldehyde]]s
| OtherFunction = {{ubl|[[Acetaldehyde]]|[[Propionaldehyde]]|[[Butyraldehyde]]|[[Pentanal]]|[[Hexanal]]|[[Heptanal]]|[[Octanal]]|[[Nonanal]]|[[Decanal]]|[[Octadecanal]]}}
| OtherCompounds = {{ubl|[[Methanol]]|[[Formic acid]]|[[Methanimine]]|[[Ethylene]]|[[Phosgene]]|[[Carbonyl fluoride]]|[[Thioformaldehyde]]}}
}}
}}

'''Formaldehyde''' ({{IPAc-en|audio=En-us-Formaldehyde2.ogg|f|ɔːr|ˈ|m|æ|l|d|ɪ|h|aɪ|d}} {{respell|for|MAL|di|hide}}, {{IPAc-en|USalso|audio=En-us-Formaldehyde.ogg|f|ə|r|-}} {{respell|fər|-}}) ([[Preferred IUPAC name|systematic name]] '''methanal''') is an [[organic compound]] with the [[chemical formula]] {{chem2|CH2O}} and structure {{chem2|H\sCHO}}, more precisely {{chem2|H2C\dO}}. The compound is a pungent, colourless gas that [[Polymerization|polymerises]] spontaneously into [[paraformaldehyde]]. It is stored as aqueous solutions ('''formalin'''), which consists mainly of the hydrate CH<sub>2</sub>(OH)<sub>2</sub>. It is the simplest of the [[aldehyde]]s ({{chem2|R\sCHO}}). As a precursor to many other materials and chemical compounds, in 2006 the global production of formaldehyde was estimated at 12&nbsp;million tons per year.<ref>{{Cite book |last=Humans |first=IARC Working Group on the Evaluation of Carcinogenic Risks to |url=https://www.ncbi.nlm.nih.gov/books/NBK326456/ |title=Summary of Data Reported and Evaluation |date=2006 |publisher=International Agency for Research on Cancer |language=en |access-date=2023-03-06 |archive-date=2024-02-02 |archive-url=https://web.archive.org/web/20240202212813/https://www.ncbi.nlm.nih.gov/books/NBK326456/ |url-status=live}}</ref> It is mainly used in the production of industrial [[resin]]s, e.g., for [[particle board]] and [[coating]]s. 

Formaldehyde also occurs naturally. It is derived from the degradation of [[serine]], [[dimethylglycine]], and [[lipid]]s.  [[Demethylase]]s act by converting N-methyl groups to formaldehyde.<ref>{{cite journal |doi=10.1038/s42004-019-0224-2 |title=How formaldehyde reacts with amino acids |date=2019 |last1=Kamps |first1=Jos J. A. G. |last2=Hopkinson |first2=Richard J. |last3=Schofield |first3=Christopher J. |last4=Claridge |first4=Timothy D. W. |journal=Communications Chemistry |volume=2 |issue=1 |page=126 |bibcode=2019CmChe...2..126K }}</ref>

Formaldehyde is classified as a group 1 [[carcinogen]]{{refn|group=note|name=carcinogen|Formaldehyde is classified as a carcinogen, according to the [[United States Environmental Protection Agency|Environmental Protection Agency]], [[International Agency for Research on Cancer|International Agency for Research on Cancer (IARC)]], and U.S. National Toxicology Program.<ref name="cancer.gov">{{cite web|url=https://www.cancer.gov/about-cancer/causes-prevention/risk/substances/formaldehyde/formaldehyde-fact-sheet|access-date=2023-09-21|archive-url=https://web.archive.org/web/20230920183106if_/https://www.cancer.gov/about-cancer/causes-prevention/risk/substances/formaldehyde/formaldehyde-fact-sheet|archive-date=2023-09-20|title=Formaldehyde and Cancer Risk|date=10 June 2011}}</ref>}}<ref>{{cite book |last1=Zhang |first1=Luoping |title=Formaldehyde: Exposure, Toxicity and Health Effects |date=2018 |publisher=Royal Society of Chemistry, The |location=Cambridge |isbn=9781782629733 |edition=1st |chapter=CH 5. Formaldehyde Carcinogenesis}}</ref> and can cause respiratory and skin [[irritation]] upon exposure.<ref name="cancer.gov" />