CAS 14542-93-9 1,1,3,3-Tetramethylbutyl isocyanide (HCID 26725)

Names & identifiers

Preferred name: 1,1,3,3-Tetramethylbutyl isocyanide
IUPAC: 2-isocyano-2,4,4-trimethylpentane
English name: 1,1,3,3-Tetramethylbutyl isocyanide
Molecular formula: C9H17N
Molecular weight: 139.24

Names & synonyms

1,1,3,3-Tetramethylbutyl isocyanidePentane, 2-isocyano-2,4,4-trimethyl-Walborsky's reagent1,1,3,3-TetramethylbutylisonitrileNSC 141688Butyl isocyanide, 1,1,3,3-tetramethyl-EINECS 238-577-8DTXSID9065784tertOctyl isocyanidetertOctyl isonitrileRefChem:4096332Isocyano2,4,4trimethylpentane

Show more names

2-isocyano-2,4,4-triMethylpentaneWALBORSKY REAGENTTERT-OCTYLISONITRILETERT-OCTYL ISOCYANIDE2-isocyano-2,4,4-trimethyl-pentan1,1,3,3-TETRAMETHYLBUTYL ISOCYANIDE FOR

DTXCID4034730Pentane, 2isocyano2,4,4trimethyl1,1,3,3Tetramethylbutylisonitrile1,1,3,3Tetramethylbutyl isocyanateButyl isocyanide, 1,1,3,3tetramethylButyl isocyanide, 1,1,3,3tetramethyl (8CI)Butyl isocyanide, 1,1,3,3-tetramethyl-(8CI)14542-93-9

Database identifiers

CAS: 14542-93-9
PubChem CID: 26725
DTXSID: DTXSID9065784
ChEMBL: CHEMBL5567109
UNII: 9EVN2N5TVN
Nikkaji: J108.673A

Properties

Computed structural properties

XLogP: 2.6
Topological polar surface area: 4.4 Å²
Hydrogen bond donors: 0
Hydrogen bond acceptors: 1
Rotatable bonds: 2
Heavy atoms: 10
Formal charge: 0
Complexity: 151

Experimental & physicochemical properties

Chemical ClassesNitrogen Compounds -> Other Nitrogen Compounds

Physical DescriptionClear colorless liquid; [Acros Organics MSDS]

Physicochemical properties

Boiling point: 55 · 55-57 °C11 mm Hg(lit.)
Density: 0.794 g/mL · 0.794 g/mL at 25 °C(lit.)
refractive index: 20 · n20/D 1.422(lit.)
Flash point: 125 °F · 125 °F
storage temp.: 2 · 2-8°C
solubility: insol water; sol common organic solvents
form: clear liquid
color: Colorless to Almost colorless
BRN: 2076559 · 2076559
InChI: InChI=1S/C9H17N/c1-8(2,3)7-9(4,5)10-6/h7H2,1-5H3
InChIKey: YVPXQMYCTGCWBE-UHFFFAOYSA-N
SMILES: C(C(C)(C)C)C(C)(C)[N+]#[C-]
CAS DataBase Reference: 14542 · 14542-93-9(CAS DataBase Reference)
FDA UNII: 9 EVN2N5TVN · 9EVN2N5TVN
EPA Substance Registry System: 2 · Pentane, 2-isocyano-2,4,4-trimethyl- (14542-93-9)
UNSPSC Code: 12352117 · 12352117
NACRES: 22 · NA.22
Symbol(GHS): 2 · GHS02
Signal word: Warning
Hazard statements: 226 · H226
Precautionary statements: 210 · P210-P370+P378
PPE: Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
Hazard Codes: Xn
Risk Statements: 10 · 10-20/21/22
Safety Statements: 23 · 23-36/37
RIDADR: 1993 · UN 1993 3/PG 3
WGK Germany: 3 · 3
F: 10 · 10-21
TSCA: TSCA listed
HS Code: 2929 · 2929 90 00
HazardClass: 3.2 · 3.2
PackingGroup: III
Storage Class: 3 · 3 - Flammable liquids
Hazard Classifications: 3 · Flam. Liq. 3

Safety & regulation

Hazard information

Regulatory Information1,1,3,3-Tetramethylbutyl isocyanide: Does not have an individual approval but may be used under an appropriate group standard

Hazards SummaryAn irritant; Harmful by ingestion, inhalation, and skin absorption (may be metabolized to cyanide); [Acros Organics MSDS] See Ethyl isocyanide.

Safety data

F: 10-21
PPE: Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
wgk: 3
tsca: TSCA listed
ridadr: UN 1993 3/PG 3
hs_code: 2929 90 00
risk_code: 10-20/21/22
Signal word: Warning
Symbol(GHS): GHS02
hazard_code: Xn
safety_code: 23-36/37
hazard_class: 3.2
Storage Class: 3 - Flammable liquids
packing_group: III
Hazard statements: H226
Hazard Classifications: Flam. Liq. 3
Precautionary statements: P210-P370+P378

Chemistry & industry

Uses & manufacturing

General Manufacturing InformationPentane, 2-isocyano-2,4,4-trimethyl-: INACTIVE

Applications

Uses1,1,3,3-Tetramethylbutyl isocyanide was used in the synthesis of substituted furans and imides.

Preparation methods · 1 item

PreparationTo a stirred solution of 83.0 g (0.528 mole) of N-(l,l,3,3-tetramethylbutyl) formamide in 11 of DMF was added dropwise, under a nitrogen atmosphere, a solution made up of thionyl chloride (40.3 ml, 0.55 mole) dissolved in 150 ml of DMF. The addition was at such a rate that the temperature did not exceed -50°C. After the addition, the cooling bath was removed momentarily to allow the temperature to increase to -35°C and then it was replaced while 118.0 g (1.11 mole) of sodium carbonate (anhydrous grade) was added. Then the cooling bath was removed and the reaction mixture was diluted with ice-cold water in a separatory funnel and then extracted with pentane. The pentane extract was dried over sodium sulfate and concentrated, and the product distilled to yield 68.4 g (93% yield), b.p. 55.5-56.6°C (11 mm). Infrared spectrum (neat) 2110 c m " 1 (s); nmr (neat) 51.08 [s, 9, C(CH3) 2] , 1.43 [t, 6, J = 2Hz, C(CH3) 2] , 1.58 (t, 2, J = 2.3 Hz, CH2).