| Identification | More | [Name]
Iodoacetonitrile | [CAS]
624-75-9 | [Synonyms]
AKOS 91685
IODOACETONITRILE
Acetonitrile, iodo-
Iodoacetonitrile,97%
10doacetonitrile
iodomethyl cyanide
2-Iodoacetonitrile
Cyanoiodomethane
Cyanomethyl iodide | [EINECS(EC#)]
210-860-0 | [Molecular Formula]
C2H2IN | [MDL Number]
MFCD00001886 | [Molecular Weight]
166.95 | [MOL File]
624-75-9.mol |
| Chemical Properties | Back Directory | [Appearance]
clear red to brown liquid | [Boiling point ]
182-184 °C/720 mmHg (lit.) | [density ]
2.307 g/mL at 25 °C(lit.)
| [refractive index ]
n20/D 1.574(lit.)
| [RTECS ]
AM0740000 | [Fp ]
187 °F
| [storage temp. ]
0-6°C | [solubility ]
Chloroform, Methanol (Slightly) | [form ]
Liquid | [color ]
Clear red to brown | [Specific Gravity]
2.307 | [Water Solubility ]
Soluble in benzene, alcohol, acetone, ether. Slightly soluble in water. Insoluble in hexane. | [Sensitive ]
Light Sensitive | [BRN ]
1734628 | [Exposure limits]
NIOSH: IDLH 25 mg/m3 | [Stability:]
Light Sensitive | [CAS DataBase Reference]
624-75-9(CAS DataBase Reference) | [NIST Chemistry Reference]
Iodoacetonitrile(624-75-9) | [EPA Substance Registry System]
624-75-9(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
C,T | [Risk Statements ]
R22:Harmful if swallowed.
R34:Causes burns.
R36/37/38:Irritating to eyes, respiratory system and skin .
R23/24/25:Toxic by inhalation, in contact with skin and if swallowed . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
S24/25:Avoid contact with skin and eyes . | [RIDADR ]
UN 3265 8/PG 2
| [WGK Germany ]
3
| [F ]
8-10-19-21 | [HazardClass ]
8 | [PackingGroup ]
II | [HS Code ]
29269090 |
| Hazard Information | Back Directory | [Chemical Properties]
clear red to brown liquid | [Uses]
Iodoacetonitrile is used for alkylation of nucleophiles. It undergoes Reformatsky and Wittig-type reactions with aldehydes. | [Synthesis]
Step 2. The method followed the synthesis of literature S5: 2,6-piperidinedimethanol (3.80 g, 26.21 mmol), iodoacetonitrile (5.24 g, 31.45 mmol), triethylamine (Et3N, 4.38 mL, 31.45 mmol) and anhydrous N,N-dimethylformamide (DMF, 20 mL) were added to the reaction system. Upon completion of the reaction, the product was purified by fast column chromatography using a solvent mixture of dichloromethane (CH2Cl2) and methanol (CH3OH) (9:1, v/v) as eluent to afford iodoacetonitrile as a straw-colored oily substance (2.5 g, 53% yield). the molecular ion peak m/z (M + H)+ was determined by FAB MS to be 185. iodoacetonitrile was prepared using the Finkelstein reaction: Bromoacetonitrile (BrCH2CN, 3.77 g, 0.0314 mmol) was added dropwise to an acetone solution of sodium iodide (NaI, 4.71 g, 0.031 mmol) under stirring. A precipitate of sodium bromide (NaBr) was produced within a few minutes of the reaction, indicating that a halogen exchange reaction had occurred. The sodium bromide was removed by filtration and the acetone was subsequently evaporated under vacuum to give the crude product iodoacetonitrile (5.24 g, 100% yield). | [References]
[1] Patent: WO2005/61453, 2005, A1. Location in patent: Page/Page column 15
[2] Journal of the American Chemical Society, 1980, vol. 102, # 4, p. 1367 - 1371 |
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