Tetramethylsuccinonitrile

Tetramethylsuccinonitrile[1]
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 [2]
Identifiers
CAS Number
  • 3333-52-6 ☒N
3D model (JSmol)
  • Interactive image
Abbreviations TMSN[3]
ChemSpider
  • 17700 checkY
ECHA InfoCard 100.129.378 Edit this at Wikidata
MeSH tetramethylsuccinonitrile
PubChem CID
  • 18745
UNII
  • 116XMU2GHK checkY
CompTox Dashboard (EPA)
  • DTXSID0026125 Edit this at Wikidata
InChI
  • InChI=1S/C8H12N2/c1-7(2,5-9)8(3,4)6-10/h1-4H3 checkY
    Key: ZVQXQPNJHRNGID-UHFFFAOYSA-N checkY
  • CC(C)(C#N)C(C)(C)C#N
Properties
Chemical formula
 C8H12N2
Molar mass 136.198 g·mol−1
Appearance Colourless crystals
Odor odorless[4]
Density 1.07 g mL−1
Melting point 169.1 °C; 336.3 °F; 442.2 K
Boiling point sublimes[4]
Thermochemistry
Std enthalpy of
formation (ΔfH⦵298)
 13.6–16.2 kJ mol−1
Std enthalpy of
combustion (ΔcH⦵298)
 −4.8767–−4.8793 MJ mol−1
Hazards
GHS labelling:
Pictograms
 GHS06: ToxicGHS07: Exclamation markGHS08: Health hazard
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):
38.9 mg/kg (rat, oral)[5]
28 ppm (mouse, 3 hr)
6 ppm (rat, 30 hr)[5]
NIOSH (US health exposure limits):
PEL (Permissible)
 TWA 3 mg/m3 (0.5 ppm) [skin][4]
REL (Recommended)
 TWA 3 mg/m3 (0.5 ppm) [skin][4]
IDLH (Immediate danger)
 5 ppm[4]
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 [77 °F], 100 kPa).
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Infobox references
Chemical compound

Tetramethylsuccinonitrile or TMSN is an organic compound with the formula (C(CH3)2CN)2, classified as a dinitrile. It is a colorless and odorless solid. TMSN is the byproduct from the use of some radical initiators used in polymer manufacture.[6]

TMSN is derived from 2,2'-azobis-isobutyronitrile:

(NC(CH3)2CN)2 → (C(CH3)2CN)2 + N2

AIBN is a common radical initiator in the manufacture of polyvinyl chloride polymers.

Safety considerations

Because PVC is pervasive and can contain TMSN, the safety aspects of this dinitrile has generated interest.[7]

Symptoms of large or short exposure to this substance include convulsions, dizziness, headache, nausea, vomiting or even unconsciousness, hence affects central nervous system.

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/m3 over an eight-hour time-weighted average.[3]

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. ^ a b "Tetramethyl succinonitrile". NIOSH Pocket Guide to Chemical Hazards. Centers for Disease Control and Prevention. Retrieved 15 November 2013.
  4. ^ a b c d e NIOSH Pocket Guide to Chemical Hazards. "#0604". National Institute for Occupational Safety and Health (NIOSH).
  5. ^ a b "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.