3085-76-5

Usage

Chemical Properties

clear colorless to yellow liquid

InChI:InChI=1/C7H14N2/c1-6(2)9(5-8)7(3)4/h6-7H,1-4H3

Upstream product

• 2700-30-3 N,N-diisorpopylformamide 
• 53249-10-8 [1-Chloro-1-diisopropylamino-meth-(Z)-ylidene]-phosphoramidic acid diisobutyl ester 
• 420-04-2 CYANAMID 
• 75-26-3 isopropyl bromide 
• 24948-81-0 chloro-diisopropyl-amine 
• 74-90-8 hydrogen cyanide 
• 119072-55-8 tert-butylisonitrile 
• 77464-05-2 N,N-diisopropylurea 
• 506-68-3 bromocyane 
• 108-18-9 diisopropylamine 
• 20611-81-8 disodium cyanamide 
• 1192-27-4 5-diazo-1,3-cyclopentadiene 
• 128871-10-3 2-(Diisopropylamino)-1λ³-phosphaethin 
• 22293-10-3 (1-diazoethyl)benzene 

Downstream Products

• 6280-36-0 5-diisopropylaminotetrazole 
• 23547-16-2 N_.N-Diisopropyl-N'-(2-chlor-cyclohexyl)-harnstoff 
• 53400-61-6 8-Cyano-5,6,7,8-tetrahydroquinoline 
• 76098-46-9 C₁₇H₁₉ClN₂O₂ 
• 104132-53-8 N-(4-Chlorphenylglyoxyloyl)(diisopropylamino)formimidoylchlorid 
• 104132-55-0 N-(4-Bromphenylglyoxyloyl)(diisopropylamino)formimidoylchlorid 
• 162789-68-6 dimethyl 2-(N,N-diisopropylamino)-5-ethoxyfuran-3,4-dicarboxylate 

Relevant academic research and scientific papers

1-Aza-3,4-diptiospholenes by [3 + 2] cycloaddition of 2-(diisopropylamino)phosphaethyne to diazo derivatives R1R2C=N2

The reaction of the (diisopropylamino)phosphaethyne (1) with diazo compounds of the type R1R2C=N2 (2a-2c) unexpectedly leads in high yields (60-90%) to the 1-aza-3,4-diphospholene derivatives 3a-3c, a new class of heterocycles. NMR investigations of the analogous reaction of 1 with diazocyclopentadiene 2d show that the multi-step formation of 3a-3c proceeds via the 1-aza-3,4-diphospholes 6a-6d as intermediates. VCH Verlagsgesellschaft mbH, 1996.

Preparation method of cyano tertiary amine

The invention relates to the technical field of organic synthesis methods, in particular to a preparation method of N, N-disubstituted cyanamide. According to the invention, secondary amine and 2-bromo-1, 3, 4-thiadiazole, 2, 5-dibromo-1, 3, 4-thiadiazole or 2-bromo-5-methyl-1, 3, 4-thiadiazole are used as raw materials to prepare N, N-disubstituted cyano tertiary amine under the catalysis of a metal salt; the synthetic process is simple, the yield is high, the toxicity of the raw materials is extremely low, the reaction temperature is low, the reaction time is sort, the aftertreatment is simple, and the preparation process is a green preparation process with universality. The method for preparing N, N-disubstituted cyanamide solves the problems of low yield, high toxicity of raw materials, no universality, difficulty in asymmetric disubstituted synthesis and the like in the existing preparation process, and has industrial large-scale application prospects.

A allyl uncle amine compound by one-step synthesis method of cyano uncle amine compound (by machine translation)

The invention relates to a one-step synthesis of amine compound allyl unclecyano uncle amine compounds, which belongs to the technical field of organic synthetic method. The method specific synthetic process is as follows: in the airtight reaction environment, to the anhydrous organic solvent is added in the cyanogen bromide, under protection of inert gas, and then added dropwise to the solution in the allylic and high yield amine compound, to obtain allyl uncle amine compound concentration is 0.8 - 1 mol/L solution, at room temperature the reaction 16 - 24 hours later, after column chromatography separation and purification, to obtain a corresponding cyano uncle amine compound. The method to get rid of the expensive deallylation use of the catalyst, the synthesis step is less, raw materials are easy, cheap, mild reaction conditions, the operation is simple, easy to craft and industrialization. Yield 50% - 80% between. (by machine translation)

Synthesis of Cyanamides from Cyanogen Bromide under Mild Conditions through N-Cyanation of Allylic Tertiary Amines

Cyanamides were selectively formed through a one-step nucleophilic substitution reaction of allylic tertiary amines with cyanogen bromide. Because of the mild reaction conditions and good yields of the reaction, as well as the commercial availability of the starting materials, this new method represents a valuable tool for the synthesis of cyan-amides through an N-deallylation reaction and an N-cyanation reaction in one pot.

5,6,7,8-Tetrahydroquinolines. Part 7. Synthesis of 8-Cyano-5,6,7,8-tetrahydroquinolines; Di-isopropylcyanamide, a New Reagent for Cyanation of Organometallics

Di-isopropylcyanamide (1) is an effective reagent for the conversion of 8-lithio-5,6,7,8-tetrahydroquinolines into 8-cyano-5,6,7,8-tetrahydroquinolines. 8,8-Dicyano derivatives are not formed.A convenient synthesis of the reagent from disodium cyanamide is described.

Metal Complexes of Cyanamides and their Alkylation to Cyanamidium Salts. A General Synthesis of Highly Substituted Ureas, Isoureas, and Guanidines

The complexes 3a - p were prepared from disubstituted cyanamides and Lewis acids.According to a X-ray structural analysis, the antimony pentachloride complex 3a is neither a ? nor a ? complex ( CN-Sb 133 deg).The complexes 3 with SbCl5 and FeCl3 can be alkylated with tertiary alkyl chlorides, affording crystalline cyanamidium salts (5a - m) which were characterized by reactions with water, primary or secondary alcohols to give ureas (11) and uronium salts (8a - z), respectively.The guanidinium salts 9a - s were obtained with ammonia, primary and secondary amines.

2-(N,N-Disubstituted Amino)thiazoles with Electron-withdrawing Groups at Position 5: Prepaeation and Investigation on Structural Features

A convenient procedure for preparing N-mono- and NN-di-substituted cyanamides from cyanogen bromide has been developed.N,N-Disubstituted thioureas, obtained from the cyanamides, were condensed with α-bromo-α-cyanoketones to give 5-cyano-2-(N,N-disubstituted amino)thiazoles and with α-bromo-ketones to give 2-(N,N-disubstituted amino)thiazoles.Substitution in the latter products afforded 5-trifluoroacetyl- and 5-nitro-2-(N,N-disubstituted amino)thiazoles; nitration is greatly facilitated by the presence of a 4-aryl group.The average values of the barriers of rotation of the barriers to rotation of the 2-NR2 groups (ΔG298) in the 5-substituted thiazoles were established by variable temperature 1H n.m.r. spectrometry to be 57.4 kJ mol -1 (5-NO2), 56.2 (5-COCF3), and 51.5 (5-CN).I.r. examination showed that the 5-trifluoroacetyl compounds adopt one rotational form preferentially; this is probably the carbonyl O,S-syn-conformation.

The Dehydration of Ureas by Two-Phase Dichlorocarbene Reaction, a Synthetic Access to Substituted Cyanamides

A wide variety of N,N-disubstituted ureas are dehydrated in the CHCl3/NaOH catalytic two-phase system under mild conditions.The sequence of urea-transamidation and dehydration thus offers a profitable approach to aprotic cyanamides.Among various tested PT-catalysts tertiary amines prove to be the most efficient and favourable ones.Tertiary amines may also be used advantageously in the transformation of carboxylic amides and thioamides to the corresponding nitriles.The application of the same technique is less suitable in the case of N-mono-substituted ureas, N,N'-disubstituted ureas as well as N(dialkylaminomethylidene)ureas, because consequent reactions of the primarily formed cyanamides predominate.Problems concerning the dehydration mechanism are elucidated in terms of HMO-perturbation theory.

Cyanamidium Salts from Isocyanides and N-Chloroamines

Cyanamidium hexachloroantimonates (2a - g) are isolated in 60 - 80percent yield from the reaction of aryl or alkyl isocyanides (6) with N-chlorodialkylamines (5) and antimony pentachloride at low temperature.Polymerization of the isocyanides which is catalysed by antimony pentachloride is avoided through complexation with zinc- or mercury(II) chloride.The cyanamidium salts (2) react with alcohols to give tetrasubstituted uronium hexachloroantimonates (15a - s) from which isoureas (17) are obtained with base.Uronium salts (15) are also prepared from the reaction ofisocyanide dichlorides (18) with N-chloroamines (5), antimony pentachloride and alcohols.Tetra- and pentasubstituted guanidinium hexachloroantimonates (16a - r) are obtained from cyanamidium salts (2) and primary or secondary amines.

Some Extensions of von Braun (BrCN) Reaction on Organic Bases: Part II

Extensions of von Braun Cyanogen bromide reaction on Ephedra alkaloids and simpler bases have resulted in synthesis of substituted oxazolidines and a whole series of nitrogen analogues of ephedrine, desoxy ephedrine and simpler amines.The general applicability and limitations of such extension of the reaction are also discussed. - Key words: von Braun Cyanogen Bromide Reaction