4210-60-0 Usage
Description
TERT-BUTYLMALONONITRILE, also known as TBMN, is an organic compound that serves as a crucial intermediate in various chemical reactions and pharmaceutical processes. It is characterized by its unique molecular structure, which features a nitrile group and a tert-butyl group, making it a versatile building block for the synthesis of complex organic molecules.
Uses
Used in Organic Synthesis:
TERT-BUTYLMALONONITRILE is used as an organic synthesis intermediate for the preparation of various complex organic molecules. Its unique structure allows it to participate in a wide range of chemical reactions, making it a valuable component in the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Pharmaceutical Industry:
TERT-BUTYLMALONONITRILE is used as a pharmaceutical intermediate, playing a critical role in the development of new drugs and therapeutic agents. Its ability to form stable intermediates and participate in key chemical reactions makes it an essential component in the synthesis of various pharmaceutical compounds.
Used in Laboratory Research and Development:
TERT-BUTYLMALONONITRILE is utilized in laboratory research and development processes, where it is employed to explore new chemical reactions, synthesize novel compounds, and develop innovative drug candidates. Its versatility and reactivity make it a valuable tool for researchers working in the fields of organic chemistry and medicinal chemistry.
Used in Chemical Production Process:
TERT-BUTYLMALONONITRILE is also used in the chemical production process, where it is incorporated into the manufacturing of various chemical products. Its role as a key intermediate allows for the efficient production of a wide range of chemicals, contributing to the overall efficiency and productivity of the chemical industry.
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).
Check Digit Verification of cas no
The CAS Registry Mumber 4210-60-0 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 4,2,1 and 0 respectively; the second part has 2 digits, 6 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 4210-60:
(6*4)+(5*2)+(4*1)+(3*0)+(2*6)+(1*0)=50
50 % 10 = 0
So 4210-60-0 is a valid CAS Registry Number.
InChI:InChI=1/C7H10N2/c1-7(2,3)6(4-8)5-9/h6H,1-3H3
4210-60-0Relevant articles and documents
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Verhe,R. et al.
, p. 530 - 532 (1978)
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Sterically Demanding Oxidative Amidation of α-Substituted Malononitriles with Amines Using O2
Li, Jing,Lear, Martin J.,Hayashi, Yujiro
supporting information, p. 9060 - 9064 (2016/07/26)
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
Pakusch, Joachim,Beckhaus, Hans-Dieter,Ruechardt, Christoph
, p. 1191 - 1198 (2007/10/02)
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.