Iron tris(dimethyldithiocarbamate)

Iron tris(dimethyldithiocarbamate) is the coordination complex of iron with dimethyldithiocarbamate with the formula Fe(S₂CNMe₂)₃ (Me = methyl). It is marketed as a fungicide.^[3]

Iron tris(dimethyldithiocarbamate)

Names
IUPAC name Tris(dimethyldithiocarbamato)iron
Other names Ferric dimethyl dithiocarbamate, Ferbam
Identifiers
CAS Number	14484-64-1
3D model (JSmol)	coordination form: Interactive image ionic form: Interactive image
ChEBI	CHEBI:5015
ChemSpider	24884
ECHA InfoCard	100.034.970
EC Number	238-484-2
KEGG	C11223
PubChem CID	26710
RTECS number	NO8750000
UNII	SKM8W5154H
UN number	3077, 2771
CompTox Dashboard (EPA)	DTXSID8020624
InChI InChI=1S/3C3H7NS2.Fe/c3*1-4(2)3(5)6;/h3*1-2H3,(H,5,6);/q;;;+3/p-3 Key: WHDGWKAJBYRJJL-UHFFFAOYSA-K
SMILES coordination form: CN(C)C(S1)S[Fe]123(SC(S2)N(C)C)SC(S3)N(C)C ionic form: CN(C)C(=S)[S-].[Fe+3].CN(C)C(=S)[S-].CN(C)C(=S)[S-]
Properties
Chemical formula	[(CH3)2NCS2]3Fe
Molar mass	416.5 g/mol
Appearance	Dark brown to black, odorless solid[1]
Density	1.52 g/cm3
Melting point	Decomposes above 180 °C (356 °F)[1]
Boiling point	Decomposes[1]
Solubility in water	0.01% (20 °C)[1]
Hazards
Occupational safety and health (OHS/OSH):
Main hazards	Reacts with strong oxidizers, moisture[1]
Lethal dose or concentration (LD, LC):
LD50 (median dose)	3000 mg/kg (rabbit, oral) 2000 mg/kg (guinea pig, oral) 1130 mg/kg (rat, oral) 3400 mg/kg (mouse, oral)[2]
NIOSH (US health exposure limits):
PEL (Permissible)	TWA 15 mg/m3[1]
REL (Recommended)	TWA 10 mg/m3[1]
IDLH (Immediate danger)	800 mg/m3[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Synthesis, structure, bonding

Iron tris(dithiocarbamate)s are typically are prepared by salt metathesis reactions.^[3]

Iron tris(dimethyldithiocarbamate) is an octahedral coordination complex of iron(III) with D₃ symmetry.^[4]

Spin crossover (SCO) was first observed in 1931 by Cambi et al. who discovered anomalous magnetic behavior for the tris(N,N-dialkyldithiocarbamatoiron(III) complexes.^[5] The spin states of these complexes are sensitive to the nature of the amine substituents.^[6]

Reactions

Iron tris(dithiocarbamate)s react with nitric oxide to give a nitrosyl complex:

Fe(dtc)₃ + NO → Fe(dtc)₂NO + 0.5 (dtc)₂

This efficient chemical trapping reaction provides a means to detect NO.^[7]

Reflecting the strongly donating properties of dithiocarbamate ligands, iron tris(dithiocarbamate)s oxidize at relatively mild potentials to give isolable iron(IV) derivatives [Fe(S₂CNR₂)₃]⁺.^[8]

Iron tris(dithiocarbamate)s react with hydrochloric acid to give the pentacoordinate chloride:^[9]

Fe(dtc)₃ + HCl → Fe(dtc)₂Cl + Hdtc

Safety

The U.S. Occupational Safety and Health Administration (OSHA) has set the legal (permissible exposure limit) for ferbam exposure in the workplace as 15 mg/m³ over an 8-hour workday. The U.S. National Institute for Occupational Safety and Health (NIOSH) has set a recommended exposure limit (REL) of 1 mg/m³ over an 8-hour workday. At levels of 800 mg/m³, ferbam is immediately dangerous to life and health.^[1]

See also

• Zinc dimethyldithiocarbamate - a related dimethyldithiocarbamate complex of zinc
• Nickel bis(dimethyldithiocarbamate) - a related dimethyldithiocarbamate complex of nickel
• Iron tris(diethyldithiocarbamate) - a related dimethyldithiocarbamate complex of iron