13358-73-1

Basic information

• Product Name: DIBUTYLCARBAMYL CHLORIDE
• Synonyms: DIBUTYLCARBAMYL CHLORIDE;1,6-dibutyl-carbamicchlorid;dibutyl-carbamoylchlorid;dibutylcarbamoylchloride;tl459;Dibutylcarbamic acid chloride;Brn 2040828;Carbamic chloride, 1,6-dibutyl-
• CAS NO: 13358-73-1
• Molecular Formula: C9H18ClNO
• Molecular Weight: 191.7
• EINECS: 236-410-3
• Product Categories: Acid Halides;Carbonyl Compounds;Organic Building Blocks
• Mol File: 13358-73-1.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 257-260 °C(lit.)
• Flash Point: 110 °C
• Appearance: /
• Density: 0.985 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0103mmHg at 25°C
• Refractive Index: n20/D 1.456(lit.)
• PKA: -1.85±0.70(Predicted)
• CAS DataBase Reference: DIBUTYLCARBAMYL CHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: DIBUTYLCARBAMYL CHLORIDE(13358-73-1)
• EPA Substance Registry System: DIBUTYLCARBAMYL CHLORIDE(13358-73-1)

Safety Data

• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-36/37/39-45
• RIDADR: UN 3265 8/PG 3
• WGK Germany: 3
• RTECS: FD2230000
• HazardClass: IRRITANT
• Hazardous Substances Data: 13358-73-1(Hazardous Substances Data)

Usage

Uses

It is reported that Dibutylcarbamoyl Chloride is used as a reagent for the preparation of 7-azaindole-1,3-dicarboxamide hydroxyethylamine which exhibited potent BACE-1 enzyme inhibition. Also it is used for the preparation of copper salicylaldehyde semicarbazone complex which showed cytotoxicity in human cancer cells.

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.

InChI:InChI=1/C9H18ClNO/c1-3-5-7-11(9(10)12)8-6-4-2/h3-8H2,1-2H3

Upstream product

• 75-44-5 phosgene 
• 111-92-2 dibutylamine 
• 2757-23-5 chloro(chlorosulfanyl)methanone 
• 85-44-9 phthalic anhydride 
• 124-38-9 carbon dioxide 
• 32315-10-9 bis(trichloromethyl) carbonate 
• 2217-88-1 ethyl N,N-di-n-butylcarbamate 

Downstream Products

• 4559-86-8 N,N,N',N'-Tetrabutylurea 
• 17425-06-8 dibutyl-carbamic acid-(4-chloro-phenyl ester) 
• 2444-96-4 N,N-Dibutyl-thiocarbaminsaeure-S-aethylester 
• 6312-32-9 dibutyl-(2-pyridin-2-yl-ethyl)-amine 
• 85599-96-8 N,N-Dibutyl-N'-cyclohexyl-formamidine 
• 25033-65-2 N,N-dibutylbenzamide 
• 7461-43-0 4-chloro-N,N-dibutylbenzamide 
• 6315-11-3 N,N-dibutyl-4-methylbenzamide 
• 5448-40-8 N,N-dibutyl-2-methylbenzamide 
• 734-32-7 estra-4-ene-3,17-dione 

Relevant articles and documents

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.

"Solvent Friction" and the Entanglement of Long Hydrocarbon Chains

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

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].