7188-38-7 Usage
Chemical Properties
clear colorless liquid
Uses
tert-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.
Preparation
Different sources of media describe the Preparation of 7188-38-7 differently. You can refer to the following data:
1. CAUTION: Use a well-ventilated hood and observe all precautions when using hydrogen cyanide.To a 1-1, stainless steel Hoke pressure cylinder in a well-ventilated hood is added 196 gm (3.5 moles) of isobutene, 95 gm (3.5 moles) of hydrogen cyanide, and 100 gm (0.7 mole) or cuprous bromide. The cylinder is closed, shaken for 15 hr at 70°C, cooled to room temperature, and vented cautiously in the hood, and the viscous residue is poured slowly into aqueous potassium cyanide (260 gm in 100 ml of water) to decompose the cuprous complex, liberating an organic layer. The organic layer is separated, dried, and distilled under reduced pressure to afford 97 gm, b.p. 60-63°C (314 mm Hg), ng 1.3749, IR 2143 s, 1472 m, 1368 m, 1230 m, 1208 m, 855 w c m - 1; yield, 33% based on starting isobutylene; 16% based on CuBr.
2. Phosgene (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%).
General Description
Carbon 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.
Check Digit Verification of cas no
The CAS Registry Mumber 7188-38-7 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 7,1,8 and 8 respectively; the second part has 2 digits, 3 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 7188-38:
(6*7)+(5*1)+(4*8)+(3*8)+(2*3)+(1*8)=117
117 % 10 = 7
So 7188-38-7 is a valid CAS Registry Number.
InChI:InChI=1/C5H10N/c1-5(2,3)6-4/h4H,1-3H3/q+1
7188-38-7Relevant articles and documents
Facile Synthesis of Cyanide and Isocyanides from CO
Grimme, Stefan,Kooij, Bastiaan,Lin, Jack H.,Qu, Zheng-Wang,Stephan, Douglas W.,Wang, Tongtong,Xu, Maotong
supporting information, p. 16965 - 16969 (2021/06/28)
The reaction of K[N(SiMe3)2] with 13CO proceeds in C6D6 or THF affording K13CN and O(SiMe3)2 under mild conditions as confirmed by crystallographic characterization of K(18-crown-6)CN. Similarly reaction of the alkali metal amides, M[N(SiR3)R′] (M=Li, K; R=Ph, Me; R′=alkyl, aryl) provides the corresponding 13C labeled isocyanide RN13C and MOSiR3, generally in high yields. In some instances, the use of the sterically bulky Ph3Si-substituent is required to preclude 1,2-silyl migration affording the silylcarbamoyl salt M[Me3SiC(O)NR′]. These reactions have been used to obtain 19 examples of 13C labelled isocyanides, and several examples of gram scale reactions are reported. The mechanism of the reactions is probed via reliable DFT calculations.
Facile, catalyst-free cascade synthesis of sulfonyl guanidines: Via carbodiimide coupling with amines
Hazarika, Debojit,Borah, Arun Jyoti,Phukan, Prodeep
supporting information, p. 1418 - 1421 (2019/02/05)
An expeditious catalyst-free cascade coupling of N,N-dibromoarylsulfonamides with isonitriles and amines via carbodiimide intermediates has been developed. The protocol represents an elegant pathway for sulfonyl guanidines at room temperature within a short time with high yields and wide substrate scope. The carbodiimide intermediate could also be isolated in an appreciable yield.
Odorless Isocyanide Chemistry: One-Pot Synthesis of Heterocycles via the Passerini and Postmodification Tandem Reaction Based on the in Situ Capture of Isocyanides
Liu, Na,Chao, Fei,Liu, Ming-Guo,Huang, Nian-Yu,Zou, Kun,Wang, Long
, p. 2366 - 2371 (2019/05/16)
This paper reports the tandem reaction strategy of the Passerini/Staudinger/aza-Wittig reaction based on the in situ capture of isocyanides. According to this strategy, isocyanides are synthesized in situ and immediately work as the substrate for the Passerini reaction and postmodification tandem reaction in one pot. In addition, two types of new compounds, 5-oxo-3,5-dihydrobenzo[e][1,4]oxazepines and 6-oxo-5,6-dihydro-2H-1,4-oxazines, were synthesized using the tandem reaction strategy that includes five-step transformations in one pot.
