19009-39-3

Basic information

• Product Name: DIISOPROPYLCARBAMOYL CHLORIDE
• Synonyms: DIISOPROPYLCARBAMOYL CHLORIDE;DIISOPROPYLCARBAMYL CHLORIDE;N,N-DIISOPROPYLCARBAMOYL CHLORIDE;Diisopropylcarbamoyl chloride, GC 98%;Bis(1-methylethyl)carbamic acid chloride;Diisopropylcarbamic acid chloride;N,N-Diisopropylcarbamic acid chloride;N,N-Diisopropylchloroformamide
• CAS NO: 19009-39-3
• Molecular Formula: C7H14ClNO
• Molecular Weight: 163.65
• EINECS: 242-743-5
• Product Categories: Acid Halides;Carbonyl Compounds;Organic Building Blocks
• Mol File: 19009-39-3.mol

Chemical Properties

• Melting Point: 57-59 °C(lit.)
• Boiling Point: 90-93 °C15 mm Hg(lit.)
• Flash Point: 82℃
• Appearance: Colorless to pale yellow or white to pale yellow/Crystalline Powder or To Low Melting Solid
• Density: 1.019
• Vapor Pressure: 0.265mmHg at 25°C
• Refractive Index: 1.5580 (estimate)
• Storage Temp.: Inert atmosphere,Store in freezer, under -20°C
• PKA: -1.97±0.70(Predicted)
• BRN: 1754834
• CAS DataBase Reference: DIISOPROPYLCARBAMOYL CHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: DIISOPROPYLCARBAMOYL CHLORIDE(19009-39-3)
• EPA Substance Registry System: DIISOPROPYLCARBAMOYL CHLORIDE(19009-39-3)

Safety Data

• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-36/37/39-45
• RIDADR: UN 3261 8/PG 2
• WGK Germany: 3
• F: 10-21
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 19009-39-3(Hazardous Substances Data)

Usage

Uses

Diisopropylcarbamoyl chloride is used as a chemical intermediate for the preparation of various N,N-diisopropylcarbamates. These carbamates are synthesized for different applications in various industries.
Used in Pharmaceutical Industry:
Diisopropylcarbamoyl chloride is used as a key intermediate for the synthesis of 1-aryl-1-alkenyl N,N-diisopropylcarbamates. These compounds are known for their potential applications in the development of new pharmaceuticals, particularly in the treatment of various diseases and conditions.
Used in Chemical Synthesis:
In the field of chemical synthesis, Diisopropylcarbamoyl chloride is used as a reagent for the preparation of 1,3-diphenylallyl carbamate and its derivatives, such as (Z)-1,3-diphenyl-1-propenyl N,N-diisopropylcarbamate and (R)-1-(2-methoxy-4-methylphenyl)ethyl diisopropyl-carbamate. These compounds are valuable for their unique chemical properties and potential applications in various chemical processes and reactions.
Overall, Diisopropylcarbamoyl chloride is a versatile chemical compound with a wide range of applications in different industries, particularly in the synthesis of various N,N-diisopropylcarbamates and their derivatives. Its unique chemical properties make it an essential component in the development of new pharmaceuticals, chemical processes, and other applications.

Synthesis Reference(s)

Synthetic Communications, 17, p. 1887, 1987 DOI: 10.1080/00397918708057799

InChI:InChI=1/C7H14ClNO/c1-5(2)9(6(3)4)7(8)10/h5-6H,1-4H3

Upstream product

• 75-44-5 phosgene 
• 108-18-9 diisopropylamine 
• 32315-10-9 bis(trichloromethyl) carbonate 
• 4136-91-8 tetraisopropylothiuram disulphide 
• 503-38-8 trichloromethyl chloroformate 
• 20652-39-5 ethyl diisopropylcarbamate 
• 2700-30-3 N,N-diisorpopylformamide 

Downstream Products

• 86429-50-7 <(Diisopropylcarbamoyl)methylen>triphenylphosphoran 
• 4164-30-1 diisopropylnitramine 
• 601-77-4 N-nitrosodiisopropylamine 
• 51861-45-1 S-(2-cyclohexenyl) N,N-diisopropylmonothiocarbamate 
• 479635-82-0 (S)-S-(2-cyclohexenyl) N,N-diisopropylmonothiocarbamate 
• 847552-63-0 (2R/S,3E)-6-(benzyloxy)-2-{[(N,N-diisopropyl)carbamoyl]oxy}hex-3-ene 
• 847552-68-5 (2S,3E)-6-(benzyloxy)-2-{[(N,N-diisopropyl)carbamoyl]oxy}hex-3-ene 
• 847552-67-4 (2R,3E)-6-(benzyloxy)-2-{[(N,N-diisopropyl)carbamoyl]oxy}hex-3-ene 
• 847552-78-7 (2R/S,3E,d3,d4)-6-(benzyloxy)-2-{[(N,N-diisopropyl)carbamoyl]oxy}hex-3-ene 
• 132464-44-9 N,N-diisopropyl-2-(naphthalen-1-yl)benzamide 
• 549503-57-3 2-(2-fluorophenyl)ethyl diisopropylcarbamate 

Relevant articles and documents

Design, Synthesis, and Biological Evaluation of Scutellarein Derivatives Based on Scutellarin Metabolic Mechanism in Vivo

Three series of scutellarein derivatives have been designed and synthesized based on metabolic mechanism of scutellarin (1) in vivo. Their thrombin inhibition activities were tested through the analyzation of prothrombin time (PT), activated partial thromboplastin time (APTT), thrombin time (TT), and fibrinogen (FIB). The antioxidant activities of these target products were assessed by 1,1-diphenyl-2-picrylhydrazyl radical (DPPH) assay and the ability to protect PC12 cells against H2O2-induced cytotoxicity, and their solubilities were evaluated by ultraviolet (UV) spectrophotometer. The results showed that the two isopropyl groups substituted derivative (18c) demonstrated stronger anticoagulant activity, better water solubility, and good antioxidant activity compared with scutellarein (2), which warrants further development of 18c as a promising agent for ischemic cerebrovascular disease treatment. Three series of scutellarein derivatives have been designed and synthesized based on metabolic mechanism of scutellarin (1) in vivo. The results of the biological evaluation showed that the two isopropyl groups substituted derivative (18c) demonstrated stronger anticoagulant activity, better water solubility, and good antioxidant activity compared with scutellarein (2), which warrants further development of 18c as a promising agent for ischemic cerebrovascular disease treatment.

Optimization of 1,2,5-thiadiazole carbamates as potent and selective ABHD6 inhibitors

At present, inhibitors of α/β-hydrolase domain 6 (ABHD6) are viewed as a promising approach to treat inflammation and metabolic disorders. This article describes the development of 1,2,5-thiadiazole carbamates as ABHD6 inhibitors. Altogether, 34 compounds were synthesized, and their inhibitory activity was tested using lysates of HEK293 cells transiently expressing human ABHD6 (hABHD6). Among the compound series, 4-morpholino-1,2,5-thiadiazol-3-yl cyclooctyl(methyl)carbamate (JZP-430) potently and irreversibly inhibited hABHD6 (IC50 = 44 nM) and showed ～ 230-fold selectivity over fatty acid amide hydrolase (FAAH) and lysosomal acid lipase (LAL), the main off-targets of related compounds. Additionally, activity-based protein profiling indicated that JZP-430 displays good selectivity among the serine hydrolases of the mouse brain membrane proteome. JZP-430 has been identified as a highly selective, irreversible inhibitor of hABHD6, which may provide a novel approach in the treatment of obesity and type II diabetes.

Enantioselective synthesis of α-phenyl- and α-(dimethylphenylsilyl)alkylboronic esters by ligand mediated stereoinductive reagent-controlled homologation using configurationally labile carbenoids

Chain extension of boronic esters by the action of configurationally labile racemic lithium carbenoids in the presence of scalemic bisoxazoline ligands was explored for the enantioselective synthesis of the two title product classes. Enantioenriched 2° carbinols generated by oxidative work-up (NaOOH) of initial α-phenylalkylboronate products were obtained in 35-83% yield and 70-96% ee by reaction of B-alkyl and B-aryl neopentyl glycol boronates with a combination of O-(α-lithiobenzyl)-N,N-diisopropylcarbamate and ligand 3,3-bis[(4S)-4,5-dihydro-4-isopropyloxazol-2-yl] pentane in toluene solvent (-78 °C to rt) with MgBr2·OEt2 additive. Enantioenriched α-(dimethylsilylphenylsilyl)alkylboronates were obtained in 35-69% yield and 9-57% ee by reaction of B-alkyl pinacol boronates with a combination of lithio(dimethylphenylsilyl)methyl 2,4,6-triisopropylbenzoate and ligand 2,2-bis[(4S)-4,5-dihydro-4-isopropyloxazol-2-yl]propane in cumene solvent (-45 °C to -95 °C to rt). The stereochemical outcome of the second type of reaction depended on the temperature history of the organolithium·ligand complex indicating that the stereoinduction mechanism in this case involves some aspect of dynamic thermodynamic resolution. This journal is

Synthesis of scutellarein derivatives to increase biological activity and water solubility

In order to improve the biological activity and water solubility of scutellarin (1), some derivatives of its main metabolite (scutellarein) were designed and synthesized. All the compounds were tested for their thrombin inhibition activity through the analyzation of thrombin time (TT), activated partial thromboplastin time (APTT), prothrombin time (PT) and fibrinogen (FIB). Their antioxidant activities were assessed by measuring their scavenging capacities toward 1,1-diphenyl-2-picrylhydrazyl radical (DPPH) and the ability to protect PC12 cells against H2O2-induced cytotoxicity, their water solubility were also assessed by ultraviolet (UV) spectrophotometer. The results showed that compound 8b demonstrated stronger anticoagulant and antioxidant activity, better water solubility compared with scutellarein (2), which warrants it as a promising agent for the treatment of ischemic cerebrovascular disease.

Synthesis of pterostilbene and resveratrol carbamate derivatives as potential dual cholinesterase inhibitors and neuroprotective agents

Pterostilbene and resveratrol carbamate derivatives were designed and synthesized by use of a multi-target directed drug-design strategy. Their acetylcholinesterase and butylcholinesterase inhibitory activity and neuroprotective effects against hydrogen peroxide-induced PC12 cell injury were evaluated in vitro. The results indicated that some of the compounds had dual inhibitory potency against acetylcholinesterase and butylcholinesterase, and potential neuroprotective effects, and could be considered as potential multi-target-directed agents.

Development of an improved method for conversion of thiuram disulfides into N,N-dialkylcarbamoyl halides and derivatives

A convenient procedure for preparing N,N-disubstituted carbamoyl halides is reported. It consists of two steps: (1) reaction of carbon disulfide and a secondary amine in the presence of a polar organic solvent and oxygen to produce the corresponding tetraalkyl thiuram disulfides and (2) reaction of tetraalkyl thiuram disulfide with a halide in the presence of an aprotic organic solvent to produce the corresponding N,N-disubstituted carbamoyl halide. Copyright Taylor & Francis Group, LLC.

Antimalarial and antitrypanosomal activity of a series of amide and sulfonamide derivatives of a 2,5-diaminobenzophenone

Here, we describe a series of readily obtainable benzophenone derivatives with antimalarial and antitrypanosomal activity. The most active compounds display submicromolar activity against Plasmodium falciparum. Micromolar activity is obtained against Trypanosoma brucei. Main problem of the compounds is low selectivity. However, there are indications that separation of antimalarial and cytotoxic activity might by possible. In addition, some compounds inhibit human ABC transporter with nanomolar activity.

CCR5 ANTAGONISTS AS THERAPEUTIC AGENTS

The present invention relates to compounds of formula (I) or pharmaceutically acceptable derivatives thereof, useful in the treatment or prophylaxis of CCR5-related diseases and disorders, for example, in the inhibition of HIV replication, the prevention or treatment of an HIV infection, and in the treatment of the resulting acquired immune deficiency syndrome (AIDS).

Importance of the lipophilic group in carbamates having histamine H3- receptor antagonist activity

In order to evaluate changes in the lipophilic part of designed carbamates concerning their potential histamine H3-receptor antagonist properties a new series of O-[3-(1H-imidazol-4-yl)propanol]carbamates was derived containing N-mono- or dialkenyl, alkynyl, cycloalkyl, or double- branched alkyl substituents. The compounds were tested in vitro for their H3-receptor antagonist activity on synaptosomes of rat cerebral cortex and shared moderate to high antagonist activity in vitro. In this series 3-(1H- imidazol-4-yl)propyl N-(4-pentenyl)carbamate (4) was the most potent compound in vitro (K(i) = 6.3 nM). H3-receptor antagonist activity in the central nervous system (CNS) was detected for most compounds in the in vivo H3- receptor assay based upon measurement of brain N(τ)-methylhistamine levels after p.o. administration to mice. The most effective carbamate in vivo, 3- (1H-imidazol-4-yl)propyl N-(allyl)carbamate (3), showed higher CNS potency (ED50 = 0.48 mg/kg p.o.) than the reference antagonist thioperamide. For some novel carbamates their histamine H1- and H2-receptor activities were determined on isolated organs of guinea-pig thereby demonstrating their high H3-receptor selectivity.

Process for the preparation of 1-4-disubstituted-5 (4H)-tetrazolinones

1,4-Disubstituted-5(4H)-tetrazolinones of the formula (I) STR1 wherein R1, R2 and R3 have the meanings given in the specification), which are known to be useful as herbicides, can be obtained in very good yields by reacting the corresponding 1-substituted-5(4H)-tetrazolinones with the corresponding carbamoyl chlorides in the presence of 4-dimethylaminopyridine.