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Tetramethylsuccinonitrile

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Tetramethylsuccinonitrile
Partially condensed, skeletal formula of tetramethylsuccinonitrile
Partially condensed, skeletal formula of tetramethylsuccinonitrile
Ball-and-stick model of the tetramethylsuccinonitrile molecule
Names
Preferred IUPAC name Tetramethylbutanedinitrile
Other names Butanedinitrile, 2,2,3,3-tetramethyl
Identifiers
CAS Number
3D model (JSmol)
Abbreviations TMSN
ChemSpider
ECHA InfoCard 100.129.378 Edit this at Wikidata
MeSH tetramethylsuccinonitrile
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C8H12N2/c1-7(2,5-9)8(3,4)6-10/h1-4H3Key: ZVQXQPNJHRNGID-UHFFFAOYSA-N
SMILES
  • CC(C)(C#N)C(C)(C)C#N
Properties
Chemical formula C8H12N2
Molar mass 136.198 g·mol
Appearance Colourless crystals
Odor odorless
Density 1.07 g mL
Melting point 169.1 °C; 336.3 °F; 442.2 K
Boiling point sublimes
Thermochemistry
Std enthalpy of
formation (ΔfH298) 		13.6–16.2 kJ mol
Std enthalpy of
combustion (ΔcH298) 		−4.8767–−4.8793 MJ mol
Hazards
GHS labelling:
Pictograms GHS06: ToxicGHS07: Exclamation markGHS08: Health hazard
Signal word Danger
Hazard statements H300, H310, H315, H319, H330, H370, H372, H412
Precautionary statements P260, P262, P264, P270, P271, P273, P280, P284, P301+P310, P302+P350, P302+P352, P304+P340, P305+P351+P338, P307+P311, P310, P314, P320, P321, P322, P330, P332+P313, P337+P313, P361, P362, P363, P403+P233, P405, P501
Lethal dose or concentration (LD, LC):
LD50 (median dose) 38.9 mg/kg (rat, oral)
LCLo (lowest published) 28 ppm (mouse, 3 hr)
6 ppm (rat, 30 hr)
NIOSH (US health exposure limits):
PEL (Permissible) TWA 3 mg/m (0.5 ppm)
REL (Recommended) TWA 3 mg/m (0.5 ppm)
IDLH (Immediate danger) 5 ppm
Safety data sheet (SDS) ICSC 1121
Related compounds
Related alkanenitriles
Related compounds DBNPA
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

Tetramethylsuccinonitrile or TMSN is an organic compound with the formula (C(CH3)2CN)2, classified as a dinitrile, and a colorless and odorless solid derived from 2,2'-azobis-isobutyronitrile, a common radical initiator in the manufacture of PVC:

[(CH3)2C(CN)]2N2 → [(CH3)2C(CN)]2 + N2.

Because PVC is pervasive and can contain TMSN, the safety aspects of this dinitrile has generated interest.

In regards to occupational exposures, the U.S. Occupational Safety and Health Administration and the U.S. National Institute for Occupational Safety and Health have set limits for dermal exposure at 3 mg/m over an eight-hour time-weighted average.

References

  1. "TETRAMETHYL SUCCINONITRILE". International Chemistry Safety Cards. ILO and WHO. Retrieved 27 November 2023.
  2. "Tetramethyl succinonitrile". Royal Society of Chemistry. Retrieved 21 October 2015.
  3. ^ "Tetramethyl succinonitrile". NIOSH Pocket Guide to Chemical Hazards. Centers for Disease Control and Prevention. Retrieved 15 November 2013.
  4. ^ NIOSH Pocket Guide to Chemical Hazards. "#0604". National Institute for Occupational Safety and Health (NIOSH).
  5. ^ "Tetramethyl succinonitrile". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
  6. Polymeric Materials Encyclopedia, Joseph C. Salamone, 1996, CRC Press, ISBN 0-8493-2470-X
  7. Ishiwata, H; Inoue T; Yoshihira K. (July 1987). "Tetramethylsuccinonitrile in polyvinyl chloride products for food and its release into food-simulating solvents". Zeitschrift für Lebensmittel-Untersuchung und -Forschung. 185 (1): 39–42. doi:10.1007/BF01083339. PMID 3617937. S2CID 2337990.
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