Tetramethylsuccinonitrile

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Tetramethylsuccinonitrile [1]
Partially condensed, skeletal formula of tetramethylsuccinonitrile Tetramethylsuccinonitrile Structural Formula V1.svg
Partially condensed, skeletal formula of tetramethylsuccinonitrile
Tetramethylsuccinonitrile 3D ball.png
Names
Preferred IUPAC name
Tetramethylbutanedinitrile
Other names
Butanedinitrile, 2,2,3,3-tetramethyl [2]
Identifiers
3D model (JSmol)
AbbreviationsTMSN [3]
ChemSpider
ECHA InfoCard 100.129.378 OOjs UI icon edit-ltr-progressive.svg
MeSH tetramethylsuccinonitrile
PubChem CID
UNII
  • InChI=1S/C8H12N2/c1-7(2,5-9)8(3,4)6-10/h1-4H3 Yes check.svgY
    Key: ZVQXQPNJHRNGID-UHFFFAOYSA-N Yes check.svgY
  • CC(C)(C#N)C(C)(C)C#N
Properties
C8H12N2
Molar mass 136.198 g·mol−1
AppearanceColourless 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
13.6–16.2 kJ mol−1
−4.8767–−4.8793 MJ mol−1
Hazards
GHS labelling:
GHS-pictogram-skull.svg GHS-pictogram-exclam.svg GHS-pictogram-silhouette.svg
Danger
H300, H310, H315, H319, H330, H370, H372, H412
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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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:

(NC(CH3)2CN)2 → (C(CH3)2CN)2 + N2. [6]

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

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]

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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. 1 2 "Tetramethyl succinonitrile". NIOSH Pocket Guide to Chemical Hazards. Centers for Disease Control and Prevention. Retrieved 15 November 2013.
  4. 1 2 3 4 5 NIOSH Pocket Guide to Chemical Hazards. "#0604". National Institute for Occupational Safety and Health (NIOSH).
  5. 1 2 "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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