Methylenebis(dibutyldithiocarbamate)

Methylenebis(dibutyldithiocarbamate)
Names
	Preferred IUPAC name Methylene bis(dibutylcarbamodithioate)
	Other names Methylene Dibutyldithiocarbamate
Identifiers
CAS Number	10254-57-6 ;
3D model (JSmol)	Interactive image;
ChemSpider	74450;
EC Number	233-593-1;
PubChem CID	82496;
UNII	8074XM58IX ;
	InChI InChI=1S/C19H38N2S4/c1-5-9-13-20(14-10-6-2)18(22)24-17-25-19(23)21(15-11-7-3)16-12-8-4/h5-17H2,1-4H3 Key: LMODBLQHQHXPEI-UHFFFAOYSA-N;
	SMILES CCCCN(CCCC)C(=S)SCSC(=S)N(CCCC)CCCC;
Properties
Chemical formula	C19H38N2S4
Molar mass	422.77 g·mol−1
Hazards
	GHS labelling:
Pictograms
Hazard statements	H413
Precautionary statements	P273, P501
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Methylenebis(dibutyldithiocarbamate) is the organosulfur compound with the formula CH₂(SC(S)NBu₂)₂ (Bu = C4H9). It is a derivative of dibutyldithiocarbamate that is used as an additive to various lubricants, both as an antioxidant and a preservative for metal surfaces.^[2] It is prepared by alkylation of the dithiocarbamate with dichloromethane.^[3] Although it is described as colored, simple esters of dithiocarbamate are typically colorless.^[4]

References

^ "Dibutyl-carbamodithioic acid, methylene ester". pubchem.ncbi.nlm.nih.gov.
^ Theo Mang; Jürgen Braun; Wilfried Dresel; Jürgen Omeis (2011). "Lubricants, 2. Components". Ullmanns Encyclopedia of Industrial Chemistry. Wiley-VCH. doi:10.1002/14356007.o15_o04. ISBN 978-3-527-30673-2.
^ Cespedes, Carlos; Vega, Juan C. (1994). "Reactions of Dichloromethane with Thioanions. 1. Preparation of Bis(N,N-dialkylthiocarbamoylthio)methanes". Phosphorus, Sulfur and Silicon and the Related Elements. 90 (1–4): 155–8. doi:10.1080/10426509408016397.
^ John R. Grunwell (1970). "Reaction of Grignard reagents with tetramethylthiuram disulfide [yielding dithiocarbamates]". J. Org. Chem. 35 (5): 1500–1501. doi:10.1021/jo00830a052.

[1] "Dibutyl-carbamodithioic acid, methylene ester". pubchem.ncbi.nlm.nih.gov.

[Ullmann-2] Theo Mang; Jürgen Braun; Wilfried Dresel; Jürgen Omeis (2011). "Lubricants, 2. Components". Ullmanns Encyclopedia of Industrial Chemistry. Wiley-VCH. doi:10.1002/14356007.o15_o04. ISBN 978-3-527-30673-2.

[3] Cespedes, Carlos; Vega, Juan C. (1994). "Reactions of Dichloromethane with Thioanions. 1. Preparation of Bis(N,N-dialkylthiocarbamoylthio)methanes". Phosphorus, Sulfur and Silicon and the Related Elements. 90 (1–4): 155–8. doi:10.1080/10426509408016397.

[4] John R. Grunwell (1970). "Reaction of Grignard reagents with tetramethylthiuram disulfide [yielding dithiocarbamates]". J. Org. Chem. 35 (5): 1500–1501. doi:10.1021/jo00830a052.

[1]

[2]

[3]

[4]