24948-81-0

Basic information

• Product Name: N-chloro-N,N-diisopropylamine
• Synonyms: N-chloro-N,N-diisopropylamine;Chlorodiisopropylamine;N-Chlorodi(1-methylethyl)amine;N-Chlorodiisopropylamine;N-Chloro-N-(1-methylethyl)-1-methylethan-1-amine
• CAS NO: 24948-81-0
• Molecular Formula: C₆H₁₄ClN
• Molecular Weight: 135.63506
• EINECS: 246-543-9
• Mol File: 24948-81-0.mol

Chemical Properties

• Boiling Point: 132.6°Cat760mmHg
• Flash Point: 34°C
• Appearance: /
• Density: 0.922g/cm³
• Vapor Pressure: 8.78mmHg at 25°C
• Refractive Index: 1.434
• PKA: -0.49±0.70(Predicted)
• CAS DataBase Reference: N-chloro-N,N-diisopropylamine(CAS DataBase Reference)
• NIST Chemistry Reference: N-chloro-N,N-diisopropylamine(24948-81-0)
• EPA Substance Registry System: N-chloro-N,N-diisopropylamine(24948-81-0)

Safety Data

• Hazardous Substances Data: 24948-81-0(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
N-chloro-N,N-diisopropylamine is used as a chlorinating reagent for its ability to efficiently chlorinate a wide range of substrates. This makes it a valuable tool in the synthesis of various chemical compounds, contributing to the development of new organic molecules with potential applications in different fields.
Used in Pharmaceutical Production:
In the pharmaceutical industry, N-chloro-N,N-diisopropylamine serves as an intermediate. Its role in the synthesis process is crucial for the production of various medications, highlighting its importance in the development of new drugs and therapeutic agents.
Used in Agrochemical Production:
Similarly, in the agrochemical sector, N-chloro-N,N-diisopropylamine is utilized as an intermediate. It plays a key part in the synthesis of compounds used in agriculture to protect crops and enhance yields, underlining its contribution to food security and agricultural productivity.
It is important to handle N-chloro-N,N-diisopropylamine with care due to its hazardous nature if not properly managed and stored, ensuring safety in laboratories and industrial settings where it is used.

InChI:InChI=1/C6H14ClN/c1-5(2)8(7)6(3)4/h5-6H,1-4H3

Upstream product

• 108-18-9 diisopropylamine 
• 17425-88-6 N,N-diisopropyl-1,1,1-trimethylsilylamine 
• 777851-20-4 N-chloro-p-nitrobenzenesulfonamide 

Downstream Products

• 3424-21-3 triisopropylamine 
• 95-29-4 N,N-diisopropylbenzothiazole-2-sulphenamide 
• 4164-30-1 diisopropylnitramine 
• 80-16-0 N-chlorobenzenesulfonamide 
• 108-18-9 diisopropylamine 
• 3085-76-5 diisopropylcyanamide 
• 507-20-0 tertiary butyl chloride 
• 777851-20-4 N-chloro-p-nitrobenzenesulfonamide 
• 144-86-5 N-chloro-4-methylbenzenesulfonamide 
• 148115-72-4 bis(diethylamino)chlorophosphonium diphenylmethylide 
• 172909-37-4 tetraisopropylhydrazine 

Relevant articles and documents

Highly ortho-Selective Chlorination of Anilines Using a Secondary Ammonium Salt Organocatalyst

An organocatalytic, highly facile, efficient, and regioselective ortho-chlorination of anilines is described. A secondary ammonium chloride salt has been employed as the catalyst and the reaction can be conducted at room temperature without protection from air and moisture. In addition, the reaction is readily scalable and the catalyst can be recycled and reused. This catalytic protocol has been applied to the efficient synthesis of a highly potent c-Met kinase inhibitor. Mechanistic studies revealed that unique structural features of the secondary ammonium chloride salt are important for both the catalysis and regioselectivity of the electrophilic ortho-chlorination.

An insight of the reactions of amines with trichloroisocyanuric acid

The reaction between amines or α-aminoacids with trichloroisocyanuric acid is studied under various conditions: N,N-dichloroamines, nitriles and ketones can be obtained from primary amines, while free aminoacids undergo oxidative decarboxylation to the corresponding nitrile of one less carbon atom.

Oxidation of aliphatic amines by aqueous chlorine

The oxidation of aliphatic amines by aqueous chlorine has been studied. The kinetic behaviour is similar for primary, secondary and tertiary aliphatic amines the elementary stop being the transfer of chlorine from the hypochlorous acid molecule to the nitrogen of the free amine group. Chlorination of aliphatic primary and secondary amines involves some water molecules in the transition state. Inductive effects are also discussed.

REACTION OF TERVALENT PHOSPHORUS COMPOUNDS WITH STERICALLY HINDERED N-CHLOROAMINES

Reaction of tervalent phosphorus compounds with sterically hindered N-halogenoamines (1,2) proceeds via the formation of halogenophosphonium intermediates (3), containing an anion R2N-.Intermediates react with alcohols to afford alkoxyphosphonium salts (6), transform into halogenophosphonium salts (4) or P-halogenoylids.Sterical hindrances at the nitrogen atom of intermediates (3) favour the formation of P-halogenoylids.The P-chloroylid (10) exists in the chlorotropic equilibrium with the α-chloroalkylphosphine (16). Key words: Sterical hindered N-halogenoamines, N-chlorodiisopropylamine, N-chloro-trimethylsilyl-tert-butylamine, alkoxyphosphonium salts, P-chloroylids, 1,2-CP-chlorotropy, positive halogen, NMR spectra, halogenophilic substitution.

Structure-activity considerations in kinetics and mechanism of chlorine exchange between chloramine-T and secondary amines

To study the mechanism of N-chlorination of secondary amines by chloramine-T, the kinetics of the reactions of some aromatic-substituted analogues of N-chlorobenzenesulfonamide with various secondary amines were determined. The importance of amine basicity and reactivity of the N-Cl bond of the N-chlorobenzenesulfonamide was also assessed. The results indicate that a mechanism involving the un-ionized species of both reactants (i.e., a molecular mechanism), rather than an ionic mechanism, is operating and that the reaction most likely proceeds via a six-membered-ring transition state that incorporates a water molecule.

Kinetics and mechanism of chlorine exchange between chloramine-T and secondary amines

The kinetics and mechanisms of chlorine transfer from chloramine-T (CAT) to several amines are second order and independent of p-toluenesulfonamide concentration; thus, the reaction does not involve disproportionation of CAT to dichloramine-T. From the profile of pH versus rate, the following mechanisms were proposed: (1) reaction of the ionized species of CAT with the ionized amine (ionic mechanism) and (2) reaction of the un-ionized species of CAT with the un-ionized amine (nonionic mechanism). The second-order, pH- independent rate constants calculated for the ionic and nonionic mechanisms were 1.6 and 5 x 106 M-1 s-1, respectively. Although these two mechanisms are kinetically indistinguishable, the rate constant for the nonionic mechanism is of the same order of magnitude as those calculated for similar chlorination reactions involving nonionizable chloramines, such as N- chlorosuccinimide, N-chloroquinuclidine, and N-chloro-N- methylbenzenesulfonamide. The proposed mechanism for the chlorine exchange involves a molecule of water in a cyclic, six-membered transition state.

Process for the preparation of N,N-diisopropylbenzothiazyl-2-sulfenamide

There is disclosed a process for the preparation of N,N-diisopropylbenzothiazyl-2-sulfenamide which comprises contacting an aqueous mixture of diisopropylamine and 2-mercaptobenzothiazole with an oxidizing agent in the presence of sufficient acid to neutralize the excess base, if any, in the oxidizing agent wherein the molar ratio of diisopropylamine to 2-mercaptobenzothiazole is at least 1.5 to 1.

HIGH ORTHO-SELECTIVITY IN THE CHLORINATION OF PHENOLS WITH N-CHLORODIALKYLAMINES IN THE PRESENCE OF SILICA.

Phenols are readily chlorinated by N-chlorodialkylamines in the presence of silica.Furthermore, this approach allows greater selectivity for mono:di and ortho: para chlorination than is possible with many other approaches.

Electron-gain and Electron-loss Centres derived from Chloro Amines

Exposure of dilute solutions of various dialkyl and cyclic N-chloro amines in trichlorofluoromethane to (60)Co γ-rays at 77 K gave the corresponding cations, R2N.Cl, characterised by (14)N, (35)Cl, and (1)H hyperfine coupling.The results suggest that these radicals are essentially planar at nitrogen, the SOMO being the N-Cl ?* orbital.Similar treatment of dilute solutions in methanol or methyltetrahydrofuran gave the corresponding amino radicals, R2N., also characterised by their e.s.r. spectra.There was no evidence for the formation of the parent radical anions.These results are contrasted with those for N-halogeno imides and the formation of ?* radicals from the cations R3N. and halide ions.