Formaldehyde

Formaldehyde
Names
	Preferred IUPAC name Formaldehyde
	Systematic IUPAC name Methanal
	Other names Methyl aldehyde; Methylene glycol (diol forms in aqueous solution); Methylene oxide; Formalin (aqueous solution); Formol; Carbonyl hydride; Methanone; Oxomethane; Formic aldehyde;
Identifiers
CAS Number	50-00-0 ;
3D model (JSmol)	Interactive image;
Beilstein Reference	1209228
ChEBI	CHEBI:16842 ;
ChEMBL	ChEMBL1255 ;
ChemSpider	692 ;
DrugBank	DB03843 ;
ECHA InfoCard	100.000.002
EC Number	200-001-8;
E number	E240 (preservatives)
Gmelin Reference	445
IUPHAR/BPS	4196;
KEGG	D00017 ;
MeSH	Formaldehyde
PubChem CID	712;
RTECS number	LP8925000;
UNII	1HG84L3525 ;
UN number	2209
CompTox Dashboard (EPA)	DTXSID7020637 ;
	InChI InChI=1S/CH2O/c1-2/h1H2 Key: WSFSSNUMVMOOMR-UHFFFAOYSA-N ; InChI=1/CH2O/c1-2/h1H2 Key: WSFSSNUMVMOOMR-UHFFFAOYAT;
	SMILES C=O;
Properties
Chemical formula	CH2O
Molar mass	30.026 g·mol−1
Appearance	Colorless gas
Density	0.8153 g/cm3 (−20 °C) (liquid)
Melting point	−92 °C (−134 °F; 181 K)
Boiling point	−19 °C (−2 °F; 254 K)
Solubility in water	400 g/L
log P	0.350
Vapor pressure	> 1 atm
Acidity (pKa)	13.27 (hydrate)
Magnetic susceptibility (χ)	−18.6·10−6 cm3/mol
Dipole moment	2.330 D
Structure
Point group	C2v
Molecular shape	Trigonal planar
Thermochemistry
Heat capacity (C)	35.387 J·mol−1·K−1
Std molar; entropy (S⦵298)	218.760 J·mol−1·K−1
Std enthalpy of; formation (ΔfH⦵298)	−108.700 kJ·mol−1
Gibbs free energy (ΔfG⦵)	−102.667 kJ·mol−1
Std enthalpy of; combustion (ΔcH⦵298)	571 kJ·mol−1
Pharmacology
ATCvet code	QP53AX19 (WHO)
Hazards
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H301+H311+H331, H314, H317, H335, H341, H350, H370
Precautionary statements	P201, P280, P303+P361+P353, P304+P340+P310, P305+P351+P338, P308+P310
NFPA 704 (fire diamond)	4 4 0 COR
Flash point	64 °C (147 °F; 337 K)
Autoignition; temperature	430 °C (806 °F; 703 K)
Explosive limits	7–73%
	Lethal dose or concentration (LD, LC):
LD50 (median dose)	100 mg/kg (oral, rat)
LC50 (median concentration)	333 ppm (mouse, 2 h); 815 ppm (rat, 30 min)
LCLo (lowest published)	333 ppm (cat, 2 h)
	NIOSH (US health exposure limits):
PEL (Permissible)	TWA 0.75 ppm ST 2 ppm (as formaldehyde and formalin)
REL (Recommended)	Ca TWA 0.016 ppm C 0.1 ppm [15-minute]
IDLH (Immediate danger)	Ca [20 ppm]
Safety data sheet (SDS)	MSDS(Archived)
Related compounds
Related aldehydes	Acetaldehyde; Propionaldehyde; Butyraldehyde; Pentanal; Hexanal; Heptanal; Octanal; Nonanal; Decanal; Octadecanal;
Related compounds	Methanol; Formic acid; Methanimine; Ethylene; Phosgene; Carbonyl fluoride; Thioformaldehyde;
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Formaldehyde (/fɔːrˈmældɪhaɪd/ ^ⓘ for-MAL-di-hide, US also /fər-/ ^ⓘ fər-) (systematic name methanal) is an organic compound with the chemical formula CH₂O and structure H₂C=O. The compound is a pungent, colourless gas that polymerises spontaneously into paraformaldehyde. It is stored as aqueous solutions (formalin), which consists mainly of the hydrate CH₂(OH)₂. It is the simplest of the aldehydes (R−CHO). As a precursor to many other materials and chemical compounds, in 2006 the global production of formaldehyde was estimated at 12 million tons per year.^[14] It is mainly used in the production of industrial resins, e.g., for particle board and coatings.

Formaldehyde also occurs naturally. It is derived from the degradation of serine, dimethylglycine, and lipids. Demethylases act by converting N-methyl groups to formaldehyde.^[15]

Formaldehyde is classified as a group 1 carcinogen^{[note 1]}^[17] and can cause respiratory and skin irritation upon exposure.^[16]

^ ^a ^b "Front Matter". Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: Royal Society of Chemistry. 2014. p. 908. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4.
^ ^a ^b "SIDS Initial Assessment Report" (PDF). International Programme on Chemical Safety. Archived from the original (PDF) on 2019-03-28. Retrieved 2019-04-21.
^ Spence, Robert; Wild, William (1935). "114. The vapour-pressure curve of formaldehyde, and some related data". Journal of the Chemical Society (Resumed): 506–509. doi:10.1039/jr9350000506.
^ "PubChem Compound Database; CID=712". National Center for Biotechnology Information. Archived from the original on 2019-04-12. Retrieved 2017-07-08.
^ "Acidity of aldehydes". Chemistry Stack Exchange. Archived from the original on 2018-09-01. Retrieved 2019-04-21.
^ Nelson, R. D. Jr.; Lide, D. R.; Maryott, A. A. (1967). "Selected Values of electric dipole moments for molecules in the gas phase (NSRDS-NBS10)" (PDF). Archived (PDF) from the original on 2018-06-08. Retrieved 2019-04-21.
^ Weast, Robert C., ed. (1981). CRC Handbook of Chemistry and Physics (62nd ed.). Boca Raton, Florida: CRC Press. pp. C–301, E–61. ISBN 0-8493-0462-8.
^ CRC handbook of chemistry and physics: a ready-reference book of chemical and physical data. William M. Haynes, David R. Lide, Thomas J. Bruno (2016-2017, 97th ed.). Boca Raton, Florida. 2016. ISBN 978-1-4987-5428-6. OCLC 930681942.{{cite book}}: CS1 maint: location missing publisher (link) CS1 maint: others (link)
^ ^a ^b ^c Record of Formaldehyde in the GESTIS Substance Database of the Institute for Occupational Safety and Health, accessed on 13 March 2020.
^ ^a ^b ^c NIOSH Pocket Guide to Chemical Hazards. "#0293". National Institute for Occupational Safety and Health (NIOSH).
^ NIOSH Pocket Guide to Chemical Hazards. "#0294". National Institute for Occupational Safety and Health (NIOSH).
^ "Substance Name: Formaldehyde [USP]". ChemlDplus. US National Library of Medicine. Archived from the original on 2017-09-18.
^ ^a ^b "Formaldehyde". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
^ Humans, IARC Working Group on the Evaluation of Carcinogenic Risks to (2006). Summary of Data Reported and Evaluation. International Agency for Research on Cancer. Archived from the original on 2024-02-02. Retrieved 2023-03-06.
^ Kamps, Jos J. A. G.; Hopkinson, Richard J.; Schofield, Christopher J.; Claridge, Timothy D. W. (2019). "How formaldehyde reacts with amino acids". Communications Chemistry. 2 (1): 126. Bibcode:2019CmChe...2..126K. doi:10.1038/s42004-019-0224-2.
^ ^a ^b "Formaldehyde and Cancer Risk". 10 June 2011. Archived from the original on 2023-09-20. Retrieved 2023-09-21.
^ Zhang, Luoping (2018). "CH 5. Formaldehyde Carcinogenesis". Formaldehyde: Exposure, Toxicity and Health Effects (1st ed.). Cambridge: Royal Society of Chemistry, The. ISBN 9781782629733.

Cite error: There are <ref group=note> tags on this page, but the references will not show without a {{reflist|group=note}} template (see the help page).

[iupac2013-1] "Front Matter". Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: Royal Society of Chemistry. 2014. p. 908. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4.

[ipcs-2] "SIDS Initial Assessment Report" (PDF). International Programme on Chemical Safety. Archived from the original (PDF) on 2019-03-28. Retrieved 2019-04-21.

[3] Spence, Robert; Wild, William (1935). "114. The vapour-pressure curve of formaldehyde, and some related data". Journal of the Chemical Society (Resumed): 506–509. doi:10.1039/jr9350000506.

[4] "PubChem Compound Database; CID=712". National Center for Biotechnology Information. Archived from the original on 2019-04-12. Retrieved 2017-07-08.

[5] "Acidity of aldehydes". Chemistry Stack Exchange. Archived from the original on 2018-09-01. Retrieved 2019-04-21.

[6] Nelson, R. D. Jr.; Lide, D. R.; Maryott, A. A. (1967). "Selected Values of electric dipole moments for molecules in the gas phase (NSRDS-NBS10)" (PDF). Archived (PDF) from the original on 2018-06-08. Retrieved 2019-04-21.

[7] Weast, Robert C., ed. (1981). CRC Handbook of Chemistry and Physics (62nd ed.). Boca Raton, Florida: CRC Press. pp. C–301, E–61. ISBN 0-8493-0462-8.

[CRC97-8] CRC handbook of chemistry and physics: a ready-reference book of chemical and physical data. William M. Haynes, David R. Lide, Thomas J. Bruno (2016-2017, 97th ed.). Boca Raton, Florida. 2016. ISBN 978-1-4987-5428-6. OCLC 930681942.{{cite book}}: CS1 maint: location missing publisher (link) CS1 maint: others (link)

[GESTIS-9] Record of Formaldehyde in the GESTIS Substance Database of the Institute for Occupational Safety and Health, accessed on 13 March 2020.

[PGCH-10] NIOSH Pocket Guide to Chemical Hazards. "#0293". National Institute for Occupational Safety and Health (NIOSH).

[11] NIOSH Pocket Guide to Chemical Hazards. "#0294". National Institute for Occupational Safety and Health (NIOSH).

[12] "Substance Name: Formaldehyde [USP]". ChemlDplus. US National Library of Medicine. Archived from the original on 2017-09-18.

[IDLH-13] "Formaldehyde". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).

[14] Humans, IARC Working Group on the Evaluation of Carcinogenic Risks to (2006). Summary of Data Reported and Evaluation. International Agency for Research on Cancer. Archived from the original on 2024-02-02. Retrieved 2023-03-06.

[15] Kamps, Jos J. A. G.; Hopkinson, Richard J.; Schofield, Christopher J.; Claridge, Timothy D. W. (2019). "How formaldehyde reacts with amino acids". Communications Chemistry. 2 (1): 126. Bibcode:2019CmChe...2..126K. doi:10.1038/s42004-019-0224-2.

[cancer.gov-16] "Formaldehyde and Cancer Risk". 10 June 2011. Archived from the original on 2023-09-20. Retrieved 2023-09-21.

[18] Zhang, Luoping (2018). "CH 5. Formaldehyde Carcinogenesis". Formaldehyde: Exposure, Toxicity and Health Effects (1st ed.). Cambridge: Royal Society of Chemistry, The. ISBN 9781782629733.

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