4475-95-0

Basic information

• Product Name: 2-amino-2-methylbutyronitrile
• Synonyms: 2-amino-2-methylbutyronitrile;2-Amino-2-methylbutanenitrile.;2-Methyl-2-aminobutyronitrile;Butanenitrile, 2-amino-2-methyl-;Butyronitrile, 2-amino-2-methyl-;Einecs 224-752-6;(DL)-2-aMino-2-Methylbutanenitrile
• CAS NO: 4475-95-0
• Molecular Formula: C₅H₁₀N₂
• Molecular Weight: 98.1463
• EINECS: 224-752-6
• Mol File: 4475-95-0.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 87.5-88.5℃ (55 Torr)
• Flash Point: 70.7°C
• Appearance: /
• Density: 0.907g/cm³
• Vapor Pressure: 1.883mmHg at 25°C
• Refractive Index: 1.4302 (589.3 nm 20℃)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• CAS DataBase Reference: 2-amino-2-methylbutyronitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 2-amino-2-methylbutyronitrile(4475-95-0)
• EPA Substance Registry System: 2-amino-2-methylbutyronitrile(4475-95-0)

Safety Data

• Hazardous Substances Data: 4475-95-0(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Journal of the American Chemical Society, 82, p. 696, 1960 DOI: 10.1021/ja01488a049

General Description

A yellow liquid with an ammonia-like odor. Flash point 35°F. About the same density as water and insoluble in water. Toxic by ingestion, absorption and inhalation. May irritate eyes. Produces toxic fumes during combustion. Used to make other chemicals.

Air & Water Reactions

Highly flammable. Insoluble in water.

Health Hazard

TOXIC; may be fatal if inhaled, ingested or absorbed through skin. Inhalation or contact with some of these materials will irritate or burn skin and eyes. Fire will produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or suffocation. Runoff from fire control or dilution water may cause pollution.

Fire Hazard

HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. Vapors may form explosive mixtures with air. Vapors may travel to source of ignition and flash back. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapor explosion and poison hazard indoors, outdoors or in sewers. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids are lighter than water.

InChI:InChI=1/C5H10N2/c1-3-5(2,7)4-6/h3,7H2,1-2H3

Upstream product

• 78-93-3 butanone 
• 77287-34-4 formamide 
• 4111-08-4 2-hydroxy-2-methyl-butyronitrile 
• 143-33-9 sodium cyanide 
• 773837-37-9 sodium cyanide 

Downstream Products

• 104740-98-9 N-(toluene-4-sulfonyl)-isovaline nitrile 
• 1381803-13-9 4-amino-5-ethyl-5-methyl-3-phenyl-1H-pyrrol-2(5H)-one 
• 1251238-27-3 C₁₃H₁₆N₂O 
• 1184397-84-9 2-((4-methoxyphenyl)amino)-2-methylbutanenitrile 

Relevant articles and documents

Titanium-Catalyzed Cyano-Borrowing Reaction for the Direct Amination of Cyanohydrins with Ammonia

α-Aminonitrile was an important building block in natural products and key intermedia in organic chemistry. Herein, the direct amination of cyanohydrins with the partner of ammonia to synthesis N-unprotected α-aminonitriles is developed. The reaction proceeds via titanium-catalyzed cyano-borrowing reaction, which features high atom economy and simple operation. A broad range of ketone or aldehyde cyanohydrins was tolerated with ammonia, and the N-unprotected α-aminonitriles were synthesis with moderate to high yields under mild reaction conditions.

Approaches to the construction of substituted 4-amino-1 H -pyrrol-2(5 H)-ones

Fully substituted 4-aminopyrrolones are easily accessed via simple routes starting from imines, ketones, or α-bromophenyl acetonitriles. Imines were reacted with KCN/NH4Cl in aqueous ethanol to produce α-arylamino benzyl cyanides. On the other hand, ketones were transformed to the desired α-amino nitriles using a modified Strecker reaction. Then, α-amino nitrile precursors were allowed to react with a suitable acyl halide to produce the corresponding amides. Further treatment of these amides with ethanolic KOH converted them to highly substituted 4-amino-1H-pyrrol-2(5H)- one derivatives in moderate to excellent yields.

An automatic solid-phase synthesis of peptaibols

An automated approach to peptaibols using microwave-assisted solid-phase peptide synthesis is demonstrated with a combination of HBTU and acid fluoride mediated couplings for normal and α,α-dialkylated amino acids, respectively. The method is utilized for