27086-19-7

Basic information

• Product Name: dipropylcarbamoyl chloride
• Synonyms: dipropylcarbamoyl chloride;Dipropylcarbamic acid chloride
• CAS NO: 27086-19-7
• Molecular Formula: C₇H₁₄ClNO
• Molecular Weight: 163.64516
• EINECS: 248-217-1
• Mol File: 27086-19-7.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 226°Cat760mmHg
• Flash Point: 90.5°C
• Appearance: /
• Density: 1.023g/cm³
• Vapor Pressure: 0.084mmHg at 25°C
• Refractive Index: 1.451
• CAS DataBase Reference: dipropylcarbamoyl chloride(CAS DataBase Reference)
• NIST Chemistry Reference: dipropylcarbamoyl chloride(27086-19-7)
• EPA Substance Registry System: dipropylcarbamoyl chloride(27086-19-7)

Safety Data

• Hazardous Substances Data: 27086-19-7(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Journal of the American Chemical Society, 81, p. 714, 1959 DOI: 10.1021/ja01512a052Synthetic Communications, 17, p. 1887, 1987 DOI: 10.1080/00397918708057799

InChI:InChI=1/C7H14ClNO/c1-3-5-9(6-4-2)7(8)10/h3-6H2,1-2H3

Upstream product

• 142-84-7 di-n-propylamine 
• 2757-23-5 chloro(chlorosulfanyl)methanone 
• 32315-10-9 bis(trichloromethyl) carbonate 
• 2556-42-5 tetrapropyl thiuram disulfide 
• 184110-00-7 ethyl 2-(dipropylamino)-2-oxoacetate 
• 70785-80-7 dipropyl-oxalamic acid 
• 759-94-4 S-ethyl N,N-di-n-propylthiocarbamate 
• 55852-80-7 S-methyl N,N-di-n-propylthiocarbamate 
• 503-38-8 trichloromethyl chloroformate 
• 75-44-5 phosgene 
• 6976-50-7 ethyl N,N-dipropylcarbamate 
• 861071-28-5 dipropyl-aminooxalyl chloride 

Downstream Products

• 1186293-02-6 N'-{[1-(4-fluorophenyl)-1H-indazol-5-yl]methyl}-N,N-dipropylurea 
• 154463-89-5 1-(2-chloro-6-methylphenyl)-4-(N,N-di-n-propylcarbamoyl)-5(4H)-tetrazolinone 
• 153231-50-6 1-(3-chloro-4-trifluoromethoxy-phenyl)-4-(N,N-dipropylcarbamoyl)-5(4H)-tetrazolinone 
• 1929-77-7 Vernolate 
• 759-94-4 S-ethyl N,N-di-n-propylthiocarbamate 
• 55852-80-7 S-methyl N,N-di-n-propylthiocarbamate 
• 621-64-7 N-nitroso-N,N-dipropylamine 
• 4164-29-8 N-nitrodipropylamine 
• 67559-82-4 dipropylammonium nitrate 
• 1186293-03-7 N-{[1-(4-fluorophenyl)-1H-indazol-5-yl]methyl}-N-methyl-N',N'-dipropylurea 

Relevant articles and documents

Synthesis and Biological Evaluation of Celastrol Derivatives with Improved Cytotoxic Selectivity and Antitumor Activities

Cdc37 associates kinase clients to Hsp90 and promotes the development of cancers. Celastrol, a natural friedelane triterpenoid, can disrupt the Hsp90-Cdc37 interaction to provide antitumor effects. In this study, 31 new celastrol derivatives, 2a - 2d , 3a - 3g , and 4a - 4t , were designed and synthesized, and their Hsp90-Cdc37 disruption activities and antiproliferative activities against cancer cells were evaluated. Among these compounds, 4f , with the highest tumor cell selectivity (15.4-fold), potent Hsp90-Cdc37 disruption activity (IC50= 1.9 μM), and antiproliferative activity against MDA-MB-231 cells (IC50= 0.2 μM), was selected as the lead compound. Further studies demonstrated 4f has strong antitumor activities both in vitro and in vivo through disrupting the Hsp90-Cdc37 interaction and inhibiting angiogenesis. In addition, 4f exhibited less toxicity than celastrol and showed a good pharmacokinetics profile in vivo. These findings suggest that 4f may be a promising candidate for development of new cancer therapies.

A novel and efficient strategy for the synthesis of various carbamates using carbamoyl chlorides under solvent-free and grinding conditions using microwave irradiation

We present an efficient, fast and simple strategy of generating the intermediate carbamoyl chlorides from secondary amines using stoichiometric amounts of bis(trichloromethyl)carbonate (BTC) in solution and solvent-free conditions with excellent yields. The results obtained showed the yield increasing on whether a base was used. Finally, an efficient and rapid synthesis of variety carbamate derivatives was developed by the reaction with a high variety of different alcohols, phenols, diols and this intermediate at room temperature with grinding and in solvent-free conditions under microwave irradiation. The presence of various safe bases is shown to be effective in reducing the reaction times, increasing the yields and easing purification. The present method does not involve any hazardous phosgene.

An improved one-pot cost-effective synthesis of N,N-disubstituted carbamoyl halides and derivatives

A convenient one-pot procedure is reported for preparing N,N-disubstituted carbamoyl chlorides by using chlorocarbonylsulfenyl chloride as a carbonylating agent. It comprises the reaction of secondary amines with chlorocarbonylsulfenyl chloride in the presence of an aprotic organic solvent to produce the corresponding N,N-disubstituted carbamoyl halides. Insertion of the carbonyl group without using phosgene is the novelty of this method.