163229-43-4

Basic information

• Product Name: CARBAMIC ACID, (2-CYANOPHENYL)-, 1,1-DIMETHYLETHYL ESTER
• Synonyms: CARBAMIC ACID, (2-CYANOPHENYL)-, 1,1-DIMETHYLETHYL ESTER;Carbamic acid, (2-cyanophenyl)-, 1,1-dimethylethyl ester (9CI);(2-Cyanophenyl)carbamic acid 1,1-dimethylethyl ester;2-(tert-Butoxycarbonylamino)benzonitrile;N-Boc-2-aminobenzonitrile
• CAS NO: 163229-43-4
• Molecular Formula: C12H14N2O2
• Molecular Weight: 218.25
• Product Categories: N-BOC
• Mol File: 163229-43-4.mol

Chemical Properties

• Melting Point: 74-77°C
• Boiling Point: 165 °C(Press: 2 Torr)
• Appearance: /
• Density: 1.12±0.1 g/cm3(Predicted)
• PKA: 12.77±0.70(Predicted)
• CAS DataBase Reference: CARBAMIC ACID, (2-CYANOPHENYL)-, 1,1-DIMETHYLETHYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: CARBAMIC ACID, (2-CYANOPHENYL)-, 1,1-DIMETHYLETHYL ESTER(163229-43-4)
• EPA Substance Registry System: CARBAMIC ACID, (2-CYANOPHENYL)-, 1,1-DIMETHYLETHYL ESTER(163229-43-4)

Safety Data

• Hazard Codes: Xi,N
• Statements: 36-38-51/53
• Safety Statements: 26-61
• RIDADR: UN 3077 9 / PGIII
• WGK Germany: 3
• Hazardous Substances Data: 163229-43-4(Hazardous Substances Data)

Upstream product

• 3422-01-3 tert-butyl phenylcarbamate 
• 1122-85-6 phenyl cyanate 
• 507243-19-8 (4-chloro-4,4-difluoro-3-oxo-but-1-enyl)-(2-cyano-phenyl)-carbamic acid tert-butyl ester 
• 75-65-0 tert-butyl alcohol 
• 762241-88-3 2,3-indoledione-3-oxime O-acetate 
• 607-28-3 Isatin-3-oxime 
• 24424-99-5 di-tert-butyl dicarbonate 
• 1885-29-6 anthranilic acid nitrile 
• 7321-55-3 2,2-dimethylmalononitrile 
• 36016-38-3 tert-Butyl N-hydroxycarbamate 

Relevant articles and documents

A new efficient synthesis of ortho-cyanoarenes via directed lithiation followed by electrophilic cyanation

A one-pot procedure for the conversion of mono-substituted arenes into the ortho-cyano derivatives was accomplished through directed lithiation followed by electrophilic cyanation with phenyl cyanate.

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Base-Mediated Intramolecular Decarboxylative Synthesis of Alkylamines from Alkanoyloxycarbamates

A general and effective method for the synthesis of alkylamine via intramolecular decarboxylation of alkanoyloxycarbamates is described. The alkanoyloxycarbamates are readily prepared with alkyl carboxylic acids and hydroxylamine. The reaction shows a broad range of substrates (primary and secondary alkyl) with functional tolerance, and the corresponding products were obtained in good yields under mild conditions.

Transnitrilation from Dimethylmalononitrile to Aryl Grignard and Lithium Reagents: A Practical Method for Aryl Nitrile Synthesis

An electrophilic cyanation of aryl Grignard or lithium reagents, generated in situ from the corresponding aryl bromides or iodides, by a transnitrilation with dimethylmalononitrile (DMMN) was developed. DMMN is a commercially available, bench-stable solid. The transnitrilation with DMMN avoids the use of toxic reagents and transition metals and occurs under mild reaction conditions, even for extremely sterically hindered substrates. The transnitrilation of aryllithium species generated by directed ortho-lithiation enabled a net C-H cyanation. The intermediacy of a Thorpe-type imine adduct in the reaction was supported by isolation of the corresponding ketone from the quenched reaction. Computational studies supported the energetic favorability of retro-Thorpe fragmentation of the imine adduct. (Chemical Equation Presented).

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An efficient synthesis of cyanoarenes and cyanoheteroarenes via lithiation followed by electrophilic cyanation

A one-pot procedure for the conversion of mono-substituted arenes and heteroarenes into the ortho-cyano derivatives was achieved through directed lithiation followed by electrophilic cyanation with phenyl cyanate. This reaction method proved to be applicable to halogen-lithium exchanged intermediates, so especially useful for the synthesis of benzonitriles. The scope of the reaction sequence was explored using a number of substrates.

Indium-mediated reformatsky-type reaction of β-aminovinyl chlorodifluoromethyl ketones with heteroaryl aldehydes

Indium can efficiently mediate the Reformatsky-type reaction between some β-aminovinyl chlorodifluoromethyl ketones and a series of heteroaryl aldehydes, to afford the corresponding difluoromethylene compounds in good to high yields.