4210-60-0

Basic information

• Product Name: TERT-BUTYLMALONONITRILE
• Synonyms: RARECHEM AQ A3 0176;TERT-BUTYLMALONITRILE;TERT-BUTYLMALONONITRILE;NISTC4210600;2-tert-butylmalononitrile;2-tert-butylpropanedinitrile;tert-Butylmalononitrile
• CAS NO: 4210-60-0
• Molecular Formula: C₇H₁₀N₂
• Molecular Weight: 122.17
• Product Categories: Dinitriles;Dinitriles & Trinitriles
• Mol File: 4210-60-0.mol
• Article Data: 4

Chemical Properties

• Melting Point: 84 °C
• Boiling Point: 217.8 °C at 760 mmHg
• Flash Point: 87.1 °C
• Appearance: /
• Density: 0.93 g/cm³
• Vapor Pressure: 0.13mmHg at 25°C
• Refractive Index: 1.434
• Solubility: soluble in Methanol
• CAS DataBase Reference: TERT-BUTYLMALONONITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: TERT-BUTYLMALONONITRILE(4210-60-0)
• EPA Substance Registry System: TERT-BUTYLMALONONITRILE(4210-60-0)

Safety Data

• Statements: 23/24/25
• Safety Statements: 26-36/37/39
• RIDADR: 3276
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 4210-60-0(Hazardous Substances Data)

Usage

Uses

TERT-BUTYLMALONONITRILE can be used as organic synthesis intermediate and pharmaceutical intermediate, mainly used in laboratory research and development process and chemical production process.

Synthesis

The reaction was carried out under nitrogen. To the solution of aluminum chloride (14.5 g, 100 mmol) in 40 mL of nitromethane was added malonodinitrile 26 (6.6 g, 100 mmol). The temperature of the reaction mixture was kept between -15 and -20 °C, and tert-butyl bromide (22 g, 160 mmol) was added over a period of 30-45 min. The reaction mixture was allowed to warm to 0-5 °C and was maintained at that temperature. The reaction was monitored by TLC; the eluent was 30% EA/hexane. More tert-butyl bromide was added to complete the reaction. The reaction was worked up after 15 h by addition of a saturated solution of sodium bicarbonate to neutralize the HBr produced. The reaction mixture was extracted with methylene chloride. The organic layer was dried over anhydrous sodium sulfate and concentrated over vacuum. The 27 obtained (8.5 g, 70% yield) can be used for the next step without purification. t-Butylmalonodinitrile 27, yield (8.5 g, 70%) 1H NMR (300 MHz, CDCl3): δ 3.42(s, H), 1.24 (s, 9H).

InChI:InChI=1/C7H10N2/c1-7(2,3)6(4-8)5-9/h6H,1-3H3

Upstream product

• 130933-89-0 1,1,2,2-Tetracyan-1,2-di-tert-butylethan 
• 128672-18-4 2-tert-Butyl-2-cyano-malononitrile 
• 507-19-7 t-butyl bromide 
• 109-77-3 malononitrile 
• 507-20-0 tertiary butyl chloride 
• 353-61-7 tert-butylfluoride 
• 558-17-8 tert-Butyl iodide 
• 54879-22-0 2-bromo-2-methylpropylidenemalononitrile 
• 75-16-1 methylmagnesium bromide 
• 13166-10-4 isopropylidenemalonodinitrile 

Downstream Products

• 29097-88-9 2,5-Dicyano-1,4-bis(tert-butyldicyanomethyl)benzol 
• 55740-28-8 2-(tert-butyl)malonaldehyde 
• 29097-89-0 2,5-dicyano-3,6-difluoro-1,4,-bis(tert-butyldicyanomethyl)benzene 
• 2094-69-1 benzyl pivalate 
• 133271-21-3 5-tert-butylpyrimidin-2(1H)-one 
• 156777-81-0 5-tert-butyl-2-chloropyrimidine 
• 243653-96-5 cyano-[4-(1,1-dicyano-2,2-dimethyl-propyl)-phenyl]-acetic acid ethyl ester 
• 243653-98-7 2-tert-butyl-2-(4-cyanomethyl-phenyl)-malononitrile 
• 243653-94-3 2-tert-butyl-2-(4-iodo-phenyl)-malononitrile 
• 243653-92-1 2-tert-butyl-2-(4-nitro-phenyl)-malononitrile 
• 101225-80-3 2-tert-Butyl-2-(4-nitro-phenylazo)-malononitrile 
• 29097-86-7 2,3,5,6-Tetrafluor-1,4-bis(tert.-butyldicyanomethyl)benzol 
• 73551-24-3 N-benzyl-N,2,2-trimethylpropanamide 
• 15030-76-9 (S)-methyl 3-phenyl-2-pivalamidopropanoate 

Relevant articles and documents

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Sterically Demanding Oxidative Amidation of α-Substituted Malononitriles with Amines Using O2

An efficient amidation method between readily available 1,1-dicyanoalkanes and either chiral or nonchiral amines was realized simply with molecular oxygen and a carbonate base. This oxidative protocol can be applied to both sterically and electronically challenging substrates in a highly chemoselective, practical, and rapid manner. The use of cyclopropyl and thioether substrates support the radical formation of α-peroxy malononitrile species, which can cyclize to dioxiranes that can monooxygenate malononitrile α-carbanions to afford activated acyl cyanides capable of reacting with amine nucleophiles.

Resonanzstabilisierung von Alkylradikalen durch zwei geminale Cyangruppen

Effects of Substituents on the Strength of C-C bonds, 10. - Resonance Stabilization of Alkyl Radicals by Two Geminal Cyano groups The activation parameters of the homolytic cleavage of the Cq-Cq bonds of several dialkylated malonodinitriles (2-5) and of 1,1,2,2-tetracyanoethane (7) and the heat of dissociation of 6 in solution have been determined.Together with the ground state strain of the radical precursor (obtained from the heats of combustion or EFF calculations) the steric influence on the dissociation process has been determined.The resonancestabilization energy of α,α'-dicyanoalkyl radicals then calculated was (12.4 +/- 0.9) kcal/mol.This result is discussed within the concept of capto-dative stabilization.The destabilizing interaction of two geminal cyano groups is apparently the same in the ground state of 2-7 and the radicals generated from them.