Tert-Butyl isocyanide
Basic information
- CAS
7188-38-7- Standard SMILES
[C-]#[N+]C(C)(C)C- InChIKey
FAGLEPBREOXSAC-UHFFFAOYSA-N- Molecular formula
- C5H9N
- Average molar mass
- 83.13 g/mol
- Monoisotopic mass
- 83.07349929
Overview
Tert-butylisonitrile is an isocyanide.
Names & identifiers
- Preferred name
- Tert-Butyl isocyanide
- IUPAC
- 2-isocyano-2-methylpropane
- English name
- tert-Butyl isocyanide
- Molecular formula
- C5H9N
- Molecular weight
- 83.13
Names & synonyms
tert-BUTYL ISOCYANIDE7188-38-72-Isocyano-2-methylpropanetert-Butylisonitrilet-ButylisonitrileTBINPropane, 2-isocyano-2-methyl-t-Butyl isocyanide2-Methyl-2-isocyanopropane1,1-dimethylethyl isocyanidetert-Bu-NC22S4Z857K3
Show more names
2-ISOCYANO-2-METHYL-PROPANETERT-BUTYL ISONITRILE(CH3)3CNC2-methylpropyl cyanidet-Butylisocyanide,min.98%
NSC-141687DTXSID60222145RefChem:188204DTXCID60144636230-553-5tert-butylisocyanide2-Methylpropyl isocyanidet-butylisocyanide
Database identifiers
- CAS
7188-38-7- PubChem CID
- 23577
- DTXSID
DTXSID60222145- ChEBI
CHEBI:235305- UNII
- 22S4Z857K3
- EC Number
- 230-553-5
- Nikkaji
- J2.267.272J、J42.749G
Properties
Computed structural properties
- XLogP
- 0.9
- Topological polar surface area
- 4.4 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 1
- Rotatable bonds
- 0
- Heavy atoms
- 6
- Formal charge
- 0
- Complexity
- 77.8
Physicochemical properties
- Melting point
- 148 · 148-150 °C
- Boiling point
- 91 °C · 91 °C(lit.)
- Density
- 0.735 g/mL · 0.735 g/mL at 25 °C(lit.)
- refractive index
- 20 · n20/D 1.376(lit.)
- Flash point
- -2 °C · -2 °C
- storage temp.
- 2 · Inert atmosphere,2-8°C
- solubility
- Soluble in organic solvents such as ethanol, methanol, ether, toluene and dichloromethane.
- form
- liquid
- color
- colorless
- Specific Gravity
- 0.735 · 0.735
- BRN
- 1903156 · 1903156
- Exposure limits
- 25 mg/m3 · NIOSH: IDLH 25 mg/m3
- Stability
- store cold
- InChI
- InChI=1S/C5H9N/c1-5(2,3)6-4/h1-3H3
- InChIKey
- FAGLEPBREOXSAC-UHFFFAOYSA-N
- SMILES
- C(C)(C)(C)[N+]#[C-]
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Danger
H225 (100%): Highly Flammable liquid and vapor [Danger Flammable liquids]
P210, P233, P240, P241, P242, P243, P260, P271, P280, P284, P303+P361+P353, P304+P340, P316, P320, P370+P378, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 47 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory InformationPropane, 2-isocyano-2-methyl-: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.
Hazard Classes and CategoriesFlam. Liq. 2 (100%)
Toxicology
Treatment
Antidotes to cyanide poisoning include hydroxocobalamin and sodium nitrite, which release the cyanide from the cytochrome system, and rhodanase, which is an enzyme occurring naturally in mammals that combines serum cyanide with thiosulfate, producing comparatively harmless thiocyanate. Oxygen therapy can also be administered. (L97)
Health Effects
Exposure to high levels of cyanide for a short time harms the brain and heart and can even cause coma, seizures, apnea, cardiac arrest and death. Chronic inhalation of cyanide causes breathing difficulties, chest pain, vomiting, blood changes, headaches, and enlargement of the thyroid gland. Skin contact with cyanide salts can irritate and produce sores. (L96, L97)
Chemistry & industry
Pharmacology
Metabolism/Metabolites
Cyanide is rapidly alsorbed through oral, inhalation, and dermal routes and distributed throughout the body. Cyanide is mainly metabolized into thiocyanate by either rhodanese or 3-mercaptopyruvate sulfur transferase. Cyanide metabolites are excreted in the urine. (L96)
Applications
Descriptiontert-Butyl isocyanide is a key regent for synthesizing many heterocycles and can undergo many cyclization reactions1. It is a colorless liquid, with a strong smell, bench-stable, and soluble in most organic solvents, including methanol, ethanol, ether, toluene, and dichloromethane. Many combinations of 5-member heterocycles with C, N, S, and O atoms, and even boron-containing cycles can be done via [4+1] cycloaddition. Except for heterocyclization, the reagent can be used as a mild esterification reagent, especially in the chemistry of β-lactam antibiotics, penicillins, and cephalosporins. The Passerini reaction with α-geminal polyhalogenated aldehydes allows easy esterification of such intricate substrates.
Usestert-Butyl isocyanide is used in a tin-free procedure for alkyl radical reactions in the presence of a free-radical initiator. It is a useful intermediate in multicomponent reactions. It is also used in the synthesis of coumarines, 4H-chromenes, isoxazolines and to trap 2-cyclopropylidene-1,3-diones.
General DescriptionCarbon dative bond formation by tert-butyl isocyanide on the germanium (100) surface has been reported. It also forms complexes with metals and inserts into metal-carbon bonds to form iminoacyls.
Preparation methods
PreparationPhosgene (1.0 kg, 10.1 mol) was delivered through a wide tube into a stirred solution of N-t-butylformamide (1.01 kg, 10.0 mol) in triethylamine (1.30 kg) and o-dichlorobenzene (7.0 L) in a flask fitted with a reflux condenser charged with a freezing mixture of ice and salt (-20 C°). Water was added, the layers were separated, and the non-aqueous layer was dried over anhydrous potassium carbonate or magnesium sulfate and fractionated; bp 90–92 C°/750 mmHg; yield: 681 g (82%).
Related reactions
917 records
Compound notes
Loading…