26385-07-9

Basic information

• Product Name: N-(2-CHLOROETHYL)BENZAMIDE
• Synonyms: IFLAB-BB F0133-0020;TIMTEC-BB SBB008196;N-(2-CHLOROETHYL)BENZAMIDE;N-(2-CHLOROETHYL)BENZENECARBOXAMIDE;Benzamide, N-(2-chloroethyl)-;N-(2-Chloroethyl)benzamide, GC 99%;N-(2-Chloroethyl)benzamide,99%;NSC 520281
• CAS NO: 26385-07-9
• Molecular Formula: C₉H₁₀ClNO
• Molecular Weight: 183.63
• EINECS: 247-641-4
• Mol File: 26385-07-9.mol
• Article Data: 19

Chemical Properties

• Melting Point: 103-106 °C(lit.)
• Boiling Point: 366.4 °C at 760 mmHg
• Flash Point: 175.4 °C
• Appearance: /
• Density: 1.1611 (rough estimate)
• Vapor Pressure: 1.47E-05mmHg at 25°C
• Refractive Index: 1.5330 (estimate)
• Storage Temp.: Room temperature.
• PKA: 13.90±0.46(Predicted)
• BRN: 1943939
• CAS DataBase Reference: N-(2-CHLOROETHYL)BENZAMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: N-(2-CHLOROETHYL)BENZAMIDE(26385-07-9)
• EPA Substance Registry System: N-(2-CHLOROETHYL)BENZAMIDE(26385-07-9)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 26385-07-9(Hazardous Substances Data)

Usage

Chemical Properties

off-white to beige crystalline powder and chunks

InChI:InChI=1/C9H10ClNO/c10-6-7-11-9(12)8-4-2-1-3-5-8/h1-5H,6-7H2,(H,11,12)

Upstream product

• 151-56-4 ethyleneimine 
• 98-88-4 benzoyl chloride 
• 75-44-5 phosgene 
• 18838-10-3 N-(2-hydroxyethyl)-benzamide 
• 60-29-7 diethyl ether 
• 72047-82-6 chloroethyl benzimidate 
• 689-98-5 chloroethylamine 
• 497-25-6 dimethylenecyclourethane 
• 870-24-6 2-chloroethanamine hydrochloride 
• 7127-19-7 2-phenyl-1,3-oxazoline 
• 7646-66-4 N-benzoylaziridine 
• 98-09-9 benzenesulfonyl chloride 
• 100-07-2 4-methoxy-benzoyl chloride 
• 100-52-7 benzaldehyde 

Downstream Products

• 79834-70-1 N-(2-chloroethyl)-benzimido chloride 
• 33545-23-2 monoethanolamine benzoate 
• 53576-42-4 S-(2-benzoylamino-ethyl)-isothiourea; hydrochloride 
• 3278-15-7 N-(4-methylphenethyl)benzamide 
• 107776-87-4 N-(2-pyridin-3-yl-ethyl)-benzamide 
• 4976-05-0 N-<(2-pyridinyl)-2-ethyl>benzamide 
• 3440-28-6 N-benzoyl-beta-alanine 
• 1088-26-2 1-(4-methoxyphenyl)-2-phenyl-4,5-dihydro-1H-imidazole 
• 24919-78-6 2-phenyl-1-(2-methylphenyl)-4,5-dihydro-1H-imidazole 
• 24924-53-6 2-phenyl-1-(4-methylphenyl)-4,5-dihydro-1H-imidazole 
• 1253480-73-7 2-phenyl-1-(diphenylmethyl)-4,5-dihydro-1H-imidazole 
• 128993-57-7 4,5-dihydro-2-phenyl-1-(phenylmethyl)-1H-imidazole 
• 1427476-02-5 3-(2-phenyl-4,5-dihydro-1H-imidazol-1-yl)pyridine 

Relevant articles and documents

Dual H-bond activation of NHC-Au(i)-Cl complexes with amide functionalized side-arms assisted by H-bond donor substrates or acid additives

Novel approach with amide-tethered H-bond donor NHC ligands enabled Au(i)-catalysis via H-bonding. The plain NHC-Au(i)-Cl complex catalysed conversions of terminal N-propynamides to oxazolines, and enyne cycloisomerization with an acid additive, in DCM at

Formamides as Lewis Base Catalysts in SNReactions—Efficient Transformation of Alcohols into Chlorides, Amines, and Ethers

A simple formamide catalyst facilitates the efficient transformation of alcohols into alkyl chlorides with benzoyl chloride as the sole reagent. These nucleophilic substitutions proceed through iminium-activated alcohols as intermediates. The novel method, which can be even performed under solvent-free conditions, is distinguished by an excellent functional group tolerance, scalability (>100 g) and waste-balance (E-factor down to 2). Chiral substrates are converted with excellent levels of stereochemical inversion (99 %→≥95 % ee). In a practical one-pot procedure, the primary formed chlorides can be further transformed into amines, azides, ethers, sulfides, and nitriles. The value of the method was demonstrated in straightforward syntheses of the drugs rac-Clopidogrel and S-Fendiline.

Sulfonimidation via ring-opening of 2-oxazolines with acidic sulfonimide nucleophiles

Acidic sulfonimide nucleophiles including dibenzenesulfonimide, o-benzenesulfonimide, dimethanesulfonimide, and N-(methylsulfonyl)-benzenesulfonamide are discovered to open a variety of alkyl-, aryl- and heteroaryl-2-oxazoline rings to provide the sulfonimidation products in refluxing 1,4-dioxane. The electron-rich 2-oxazoline substrates worked well for the nucleophilic ring-opening reactions while no reaction took place for the electron-poor 2-oxazoline substrates.