13358-73-1 Usage
Description
DIBUTYLCARBAMYL CHLORIDE is an organic compound that serves as a versatile reagent in the synthesis of various pharmaceutical compounds. It is known for its ability to react with different functional groups, making it a valuable component in the development of new drugs and chemical products.
Uses
Used in Pharmaceutical Industry:
DIBUTYLCARBAMYL CHLORIDE is used as a reagent for the preparation of 7-azaindole-1,3-dicarboxamide hydroxyethylamine, which has demonstrated potent BACE-1 enzyme inhibition. This application is significant in the development of treatments for neurodegenerative diseases, such as Alzheimer's, where BACE-1 inhibition plays a crucial role in reducing the formation of beta-amyloid plaques.
Used in Cancer Research:
DIBUTYLCARBAMYL CHLORIDE is also used in the preparation of copper salicylaldehyde semicarbazone complex, which has shown cytotoxicity in human cancer cells. This application highlights the potential of DIBUTYLCARBAMYL CHLORIDE in contributing to the development of novel anticancer agents, offering new therapeutic options for patients with various types of cancer.
Preparation
In a 100 mL roundbottomed flask were placed dibutylamine (6.45 g, 0.05 mol), pyridine (4.0 g, 0.05 mol), N-cyclohexyl-N0,N0,N00,N00-tetraethylguanidine (12.7 g, 0.05 mol), and toluene (40 mL). The resulting solution was cooled to 10 °C using an ice/salt bath and carbon dioxide was bubbled into the cooled solution for 30 min. After this period of time, the pre-formed carbamate solution was added in a single portion via a cannula to a cooled ( 10 °C) solution of thionyl chloride (6 g, 0.05 mol) in toluene (40 mL). The reaction mixture was stirred at 10 °C for 45 min. It was then poured into 0.1 m aq. HCl (100 mL), giving rise to two layers. The organic layer was separated, dried over anhydrous Mg2SO4, filtered, and the solvent was removed in vacuo. The residue was distilled in vacuo (1 mmHg) at 95–98 °C to give 7.62 g (79%) of N,N-dibutyl carbamoyl chloride.
Check Digit Verification of cas no
The CAS Registry Mumber 13358-73-1 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,3,3,5 and 8 respectively; the second part has 2 digits, 7 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 13358-73:
(7*1)+(6*3)+(5*3)+(4*5)+(3*8)+(2*7)+(1*3)=101
101 % 10 = 1
So 13358-73-1 is a valid CAS Registry Number.
InChI:InChI=1/C9H18ClNO/c1-3-5-7-11(9(10)12)8-6-4-2/h3-8H2,1-2H3
13358-73-1Relevant articles and documents
An improved one-pot cost-effective synthesis of N,N-disubstituted carbamoyl halides and derivatives
Adeppa,Rupainwar,Misra, Krishna
, p. 1277 - 1280 (2010)
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.
"Solvent Friction" and the Entanglement of Long Hydrocarbon Chains
Menger, F. M.,Mounier, C. E.
, p. 1655 - 1656 (1993)
Rotation about the R2N-COOR bond in carbamates with three alkyl chains (butyl through octadecyl) was investigated by NMR.Even solvents such as hexadecane and mineral oil did not substantially impede the rotation, revealing a surprising absence of "solvent friction" induced by chain entanglement.Possible explanations at the molecular level and the relevance to membrane systems are discussed.
Process for the preparation of phthalic acid dichloride
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Page/Page column 5; 6, (2008/06/13)
Preparation of phthalic acid dichloride (I) comprises reaction of phthalic acid anhydride (II) with phosgene in presence of catalyst (N,N-disubstituted formamide (III)). Preparation of phthalic acid dichloride of formula (I) comprises reaction of phthalic acid anhydride of formula (II) with phosgene in presence of catalyst (N,N-disubstituted formamide (III) of formula (HC(O)-N(R 1>)(R 2>)). R 1>, R 2>1-22C alkyl, 2-22C alkenyl, 3-8C cycloalkyl, 6-10C aryl or 7-12C arylalkyl. Where R 1>, R 2>containing 1-22C alkyl, 2-22C alkenyl amounts to total molecular weight of (III) is at least 269 g/mol. [Image].