Adiponitrile

Adiponitrile
Names
	Preferred IUPAC name Hexanedinitrile
	Other names Adipic acid dinitrile; Adipic acid nitrile; Adipyldinitrile; 1,4-Dicyanobutane; Hexanedioic acid dinitrile; Nitrile adipico; Tetramethylene cyanide; Tetramethylene dicyanide;
Identifiers
CAS Number	111-69-3 ;
3D model (JSmol)	Interactive image;
Beilstein Reference	1740005
ChemSpider	13876621 ;
ECHA InfoCard	100.003.543
EC Number	203-896-3;
MeSH	adiponitrile
PubChem CID	8128;
RTECS number	AV2625000;
UNII	SYT33B891I ;
UN number	2205
CompTox Dashboard (EPA)	DTXSID3021936 ;
	InChI InChI=1S/C6H8N2/c7-5-3-1-2-4-6-8/h1-4H2 Key: BTGRAWJCKBQKAO-UHFFFAOYSA-N ;
	SMILES N#CCCCCC#N;
Properties
Chemical formula	C6H8N2
Molar mass	108.144 g·mol−1
Appearance	Colourless liquid
Density	951 mg mL−1
Melting point	1 to 3 °C; 34 to 37 °F; 274 to 276 K
Boiling point	295.1 °C; 563.1 °F; 568.2 K
Solubility in water	50 g/L (20 °C)
Vapor pressure	300 mPa (at 20 °C)
Refractive index (nD)	1.438
Thermochemistry
Std enthalpy of; formation (ΔfH⦵298)	84.5–85.3 kJ mol−1
Hazards
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H301, H315, H319, H330, H335
Precautionary statements	P260, P284, P301+P310, P305+P351+P338, P310
NFPA 704 (fire diamond)	4 2 0
Flash point	93 °C; 199 °F; 366 K (open cup)
Autoignition; temperature	550 °C (1,022 °F; 823 K)
Explosive limits	1.7–4.99%
	Lethal dose or concentration (LD, LC):
LD50 (median dose)	155 mg kg−1 (oral, rat)
	NIOSH (US health exposure limits):
PEL (Permissible)	none
REL (Recommended)	TWA 4 ppm (18 mg/m3)
IDLH (Immediate danger)	N.D.
Related compounds
Related alkanenitriles	Glutaronitrile
Related compounds	hexanedioic acid; hexanedihydrazide; hexanedioyl dichloride; hexanediamide; 1,4-diisocyanobutane
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Adiponitrile is an organic compound with the chemical formula (CH₂)₄(CN)₂. This viscous, colourless dinitrile is an important precursor to the polymer nylon 66. In 2005, about one million tonnes of adiponitrile were produced.^[4]

^ "adiponitrile - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 26 March 2005. Identification. Retrieved 15 June 2012.
^ ^a ^b ^c ^d NIOSH Pocket Guide to Chemical Hazards. "#0015". National Institute for Occupational Safety and Health (NIOSH).
^ "Archived copy". Archived from the original on 2015-04-02. Retrieved 2015-03-26.{{cite web}}: CS1 maint: archived copy as title (link)
^ M. T. Musser, "Adipic Acid" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2005. doi:10.1002/14356007.a01_269

[1] "adiponitrile - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 26 March 2005. Identification. Retrieved 15 June 2012.

[NIOSH-2] NIOSH Pocket Guide to Chemical Hazards. "#0015". National Institute for Occupational Safety and Health (NIOSH).

[3] "Archived copy". Archived from the original on 2015-04-02. Retrieved 2015-03-26.{{cite web}}: CS1 maint: archived copy as title (link)

[Ullmann-4] M. T. Musser, "Adipic Acid" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2005. doi:10.1002/14356007.a01_269

[1]

[2]

[4]

Names


Preferred IUPAC name Hexanedinitrile^[1]
Other names Adipic acid dinitrile Adipic acid nitrile Adipyldinitrile 1,4-Dicyanobutane Hexanedioic acid dinitrile Nitrile adipico Tetramethylene cyanide Tetramethylene dicyanide
Identifiers
CAS Number	111-69-3^Y
3D model (JSmol)	Interactive image
Beilstein Reference	1740005
ChemSpider	13876621^Y
ECHA InfoCard	100.003.543
EC Number	203-896-3
MeSH	adiponitrile
PubChem CID	8128
RTECS number	AV2625000
UNII	SYT33B891I^N
UN number	2205
CompTox Dashboard (EPA)	DTXSID3021936
InChI InChI=1S/C6H8N2/c7-5-3-1-2-4-6-8/h1-4H2^Y Key: BTGRAWJCKBQKAO-UHFFFAOYSA-N^Y
SMILES N#CCCCCC#N
Properties
Chemical formula	C₆H₈N₂
Molar mass	108.144 g·mol⁻¹
Appearance	Colourless liquid
Density	951 mg mL⁻¹
Melting point	1 to 3 °C; 34 to 37 °F; 274 to 276 K
Boiling point	295.1 °C; 563.1 °F; 568.2 K
Solubility in water	50 g/L (20 °C)
Vapor pressure	300 mPa (at 20 °C)
Refractive index (n_D)	1.438
Thermochemistry
Std enthalpy of formation (Δ_fH^⦵₂₉₈)	84.5–85.3 kJ mol⁻¹
Hazards
GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H301, H315, H319, H330, H335
Precautionary statements	P260, P284, P301+P310, P305+P351+P338, P310
NFPA 704 (fire diamond)	4 2 0
Flash point	93 °C; 199 °F; 366 K (open cup)^[2]
Autoignition temperature	550 °C (1,022 °F; 823 K)
Explosive limits	1.7–4.99%
Lethal dose or concentration (LD, LC):
LD₅₀ (median dose)	155 mg kg⁻¹ (oral, rat)
NIOSH (US health exposure limits):
PEL (Permissible)	none^[2]
REL (Recommended)	TWA 4 ppm (18 mg/m³)^[2]
IDLH (Immediate danger)	N.D.^[2]
Related compounds
Related alkanenitriles	Glutaronitrile
Related compounds	hexanedioic acid hexanedihydrazide hexanedioyl dichloride hexanediamide 1,4-diisocyanobutane
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is ^YN ?) Infobox references