1,10-Decanediol

1,10-Decanediol is a diol with the chemical formula C₁₀H₂₂O₂.

1,10-Decanediol

Identifiers
CAS Number	112-47-0
3D model (JSmol)	Interactive image
ChemSpider	34095
ECHA InfoCard	100.003.614
EC Number	203-975-2
PubChem CID	37153
UNII	5I577UDK52
CompTox Dashboard (EPA)	DTXSID3059420
InChI InChI=1S/C10H22O2/c11-9-7-5-3-1-2-4-6-8-10-12/h11-12H,1-10H2 Key: FOTKYAAJKYLFFN-UHFFFAOYSA-N
SMILES OCCCCCCCCCCO
Properties
Chemical formula	C10H22O2
Molar mass	174.284 g·mol−1
Appearance	White solid[1]
Density	0.891 g·cm−3 (80 °C)[1]
Melting point	72–75 °C[1] 81.7 °C[2]
Boiling point	297 °C (1013 hPa)[1] 170 °C (11 hPa)[1]
Solubility in water	Poorly soluble[3]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

It can be synthesized through the reduction of dimethyl sebacate using sodium borohydride in an ethanol medium, with cerium(III) chloride serving as the catalyst. The reaction duration is one day, resulting in a yield of 93%.^[4] The product of the reduction of diethyl dithiosebacate by tetrabutylammonium borohydride is also 1,10-decanediol.^[5] The electrochemical reduction of diethyl sebacate in liquid ammonia can yield 1,10-decanediol with an impressive efficiency of 95%.^[6]

The interaction between sebacic acid and diisopropyltitanium(III) borohydride ((ⁱPrO)₂TiBH₄), which is generated through the in situ reaction of diisopropyltitanium dichloride and benzyltriethylammonium borohydride in dichloromethane, can also facilitate the synthesis of 1,10-decanediol.^[7]

1,10-Decanediol is characterized as a white solid with limited solubility in water.^[1][3] It exhibits a melting point of 81.7 °C and a heat of fusion of 44.0 kJ·mol⁻¹ (252.6 J·g⁻¹).^[2] The molecular configuration of 1,10-decanediol is described as having a zigzag conformation.^[8] The bromination of 1,10-decanediol yields 1,10-dibromodecane,^[9] whereas the reaction with thionyl chloride results in the formation of 1,10-dichlorodecane.^[10] The reaction involving 1,10-decanediol, iodine, and ammonia results in the formation of sebaconitrile with a yield of 99%.^[11]

1,10-Decanediol, along with its isomers 1,9-decanediol and 1,2-decanediol, functions as an inhibitor of soil nitrification.^[12] This inhibition can mitigate nitrogen loss from soil and prevent the environmental issues associated with nitrification in agricultural settings.^[12] Furthermore, these diols exhibit a significant inhibitory effect on nitrite-forming microorganisms, even at low concentrations.^[12]