4755-50-4

Basic information

• Product Name: 4-DIMETHYLAMINOBENZOYL CHLORIDE
• Synonyms: 4-DIMETHYLAMINOBENZOYL CHLORIDE;4-(Dimethylamino)benzoic acid chloride;p-(Dimethylamino)benzoyl chloride;4-(Dimethylamino)benzoyl chloride,97%;4-(Dimethylamino)benzoyl chloride, 95%, 95%;[4-(diMethylaMino)phenyl]carbonylchloranuide;Benzoyl chloride,4-(diMethylaMino)-;4-(Chlorocarbonyl)-N,N-dimethylaniline, 4-(Chloroformyl)-N,N-dimethylaniline
• CAS NO: 4755-50-4
• Molecular Formula: C₉H₁₀ClNO
• Molecular Weight: 183.63
• Product Categories: Carbonyl Chlorides;Phenyls & Phenyl-Het;Carbonyl Chlorides;Phenyls & Phenyl-Het;Acid Halides;Carbonyl Compounds;Organic Building Blocks
• Mol File: 4755-50-4.mol

Chemical Properties

• Melting Point: 145-149 °C(lit.)
• Boiling Point: 180℃ (15 Torr)
• Flash Point: 122.5 °C
• Appearance: White to tan crystalline powder
• Density: 1.193 g/cm³
• Vapor Pressure: 0.00412mmHg at 25°C
• Refractive Index: 1.574
• PKA: 0.98±0.12(Predicted)
• Water Solubility: Reacts with water.
• Sensitive: Moisture Sensitive
• BRN: 1100858
• CAS DataBase Reference: 4-DIMETHYLAMINOBENZOYL CHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-DIMETHYLAMINOBENZOYL CHLORIDE(4755-50-4)
• EPA Substance Registry System: 4-DIMETHYLAMINOBENZOYL CHLORIDE(4755-50-4)

Safety Data

• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-36/37/39-45
• RIDADR: UN 3261 8/PG 2
• WGK Germany: 3
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 4755-50-4(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
4-Dimethylaminobenzoyl chloride is used as a key intermediate for the synthesis of various organic compounds. Its unique chemical structure allows it to participate in a range of reactions, making it a versatile building block in the creation of new molecules.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 4-Dimethylaminobenzoyl chloride is used as a starting material for the development of new drugs. Its reactivity and functional groups enable the formation of a wide array of medicinal compounds, contributing to the advancement of pharmaceutical research and drug discovery.
Used in Agrochemicals:
4-Dimethylaminobenzoyl chloride is also utilized in the agrochemical sector as a precursor for the synthesis of various agrochemical products. Its role in creating effective and targeted compounds helps improve crop protection and management strategies.

InChI:InChI=1/C9H10ClNO/c1-11(2)8-5-3-7(4-6-8)9(10)12/h3-6H,1-2H3

Upstream product

• 157119-18-1 (4-dimethylamino-phenyl)-oxoacetyl chloride 
• 619-84-1 p-N,N-dimethylaminobenzoic acid 
• 75-44-5 phosgene 
• 121-69-7 N,N-dimethyl-aniline 
• 698-70-4 4-Iodo-N,N-dimethylaniline 
• 141-75-3 butyryl chloride 
• 150-13-0 4-amino-benzoic acid 
• 79-37-8 oxalyl dichloride 
• 89165-28-6 1-(p-dimethylamino)benzoyl-3-methylimidazolium chloride 

Downstream Products

• 32987-59-0 4,4'-bis-dimethylamino-2-methyl-benzophenone 
• 860563-96-8 4-dimethylamino-4'-phenyl-benzophenone 
• 93808-08-3 4-dimethylamino-benzoic acid-(3-dimethylamino-propyl ester) 
• 77016-80-9 dodecyl 4-(N,N-dimethylamino)benzoate 
• 125628-90-2 n-hexadecyl 4-dimethylaminobenzoate 
• 15024-12-1 phenyl 4-(N,N-dimethylamino)benzoate 
• 63193-70-4 4-dimethylamino-benzoyl isothiocyanate 
• 6083-47-2 4-(dimethylamino)benzamide 
• 619-84-1 p-N,N-dimethylaminobenzoic acid 
• 1230-64-4 4-(dimethylamino)-N-(4-(dimethylamino)phenyl)benzamide 
• 21566-11-0 N,N-dimethyl-p-(dimethylamino)benzamide 
• 3765-62-6 4-(dimethylamino)-N-phenylbenzamide 
• 55198-74-8 4-dimethylamino-2'-methylbenzanilide 
• 20934-81-0 4-(benzo[d]oxazol-2-yl)aniline 

Relevant articles and documents

Synthesis and activity of four (N,N-dimethylamino)benzamide non-steroidal anti-inflammatory drugs based on thiazole and thiazoline

Four compounds derived from 2-aminothiazole and 2-amino-2-thiazoline were prepared by coupling the respective bases with the acid chlorides of either 3- or 4-(N,N-dimethylamino)benzoic acid. Products were identified using infrared spectroscopy. 1/su

Circular dichroism studies of molecular recognition with cyclophane hosts in aqueous media

Circular dichroism (CD) methods have been employed to study molecular recognition phenomena in water soluble cyclophane hosts such as 1 and 2. The CD method is well suited to these systems and produces results that complement and expand upon previous NMR

Ni-Catalyzed Direct Carboxylation of Aryl C?H Bonds in Benzamides with CO2

The direct carboxylation of inert aryl C?H bond catalyzed by abundant and cheap nickel is still facing challenge. Herein, we report the Ni-catalyzed direct carboxylation of aryl C?H bonds in benzamides under 1 atm of CO2 to afford various methyl carboxylates or phthalimides, dealing with different post-processing. The reaction displays excellent functional group tolerance and affords moderate to high carboxylation yields under mild conditions. Detail mechanistic studies suggest that a Ni(0)?Ni(II)?Ni(I) catalytic cycle may be involved in this reaction. (Figure presented.).

Systematic Evaluation of 1,2-Migratory Aptitude in Alkylidene Carbenes

Alkylidene carbenes undergo rapid inter- and intramolecular reactions and rearrangements, including 1,2-migrations of β-substituents to generate alkynes. Their propensity for substituent migration exerts profound influence over the broader utility of alkylidene carbene intermediates, yet prior efforts to categorize 1,2-migratory aptitude in these elusive species have been hampered by disparate modes of carbene generation, ultrashort carbene lifetimes, mechanistic ambiguities, and the need to individually prepare a series of 13C-labeled precursors. Herein we report on the rearrangement of 13C-alkylidene carbenes generated in situ by the homologation of carbonyl compounds with [13C]-Li-TMS-diazomethane, an approach that obviates the need for isotopically labeled substrates and has expedited a systematic investigation (13C{1H} NMR, DLPNO-CCSD(T)) of migratory aptitudes in an unprecedented range of more than 30 alkylidene carbenes. Hammett analyses of the reactions of 26 differentially substituted benzophenones reveal several counterintuitive features of 1,2-migration in alkylidene carbenes that may prove of utility in the study and synthetic application of unsaturated carbenes more generally.

Biocatalytic Strategy for the Highly Stereoselective Synthesis of CHF2-Containing Trisubstituted Cyclopropanes

The difluoromethyl (CHF2) group has attracted significant attention in drug discovery and development efforts, owing to its ability to serve as fluorinated bioisostere of methyl, hydroxyl, and thiol groups. Herein, we report an efficient biocat

Design, synthesis, biological evaluation and pharmacophore model analysis of novel tetrahydropyrrolo[3,4-c]pyrazol derivatives as potential TRKs inhibitors

The tropomyosin receptor kinases TRKs are responsible for different tumor types which caused by NTRK gene fusion, and have been identified as a successful target for anticancer therapeutics. Herein, we report a potent and selectivity TRKs inhibitor 19m through rational drug design strategy from a micromolar potency hit 17a. Compound 19m significantly inhibits the proliferation of TRK-dependent cell lines (Km-12), while it has no inhibitory effect on TRK-independent cell lines (A549 and THLE-2). Furthermore, kinases selectivity profiling showed that in addition to TRKs, compound 19m only displayed relatively strong inhibitory activity on ALK. These data may indicate that compound 19m has a good drug safety. Partial ADME properties were evaluated in vitro and in vivo. Compound 19m exhibited a good AUC values and volume of distribution and low clearance in the pharmacokinetics experiment of rats. Finally, a pharmacophore model guided by experimental results is proposed. We hope this theoretical model can help researchers find type I TRK inhibitors more efficiently.

AMINE CO-INITIATOR MIXTURE

The invention relates to a co-initiator comprising the aminobenzoate derivative according to Formula (I) and at least one ancillary amine, wherein the reactivity and solubility of said co-imitator in UV-curable resins is sufficiently high that the co-initiator can be used in UV radiation curing processes. Formula (I) wherein R1 and R2 independently represent methyl or ethyl groups; and j, k, l and m are independently 0 to 20.

Microwave-promoted synthesis of highly luminescent s-tetrazine-1,3,4-oxadiazole and s-tetrazine-1,3,4-thiadiazole hybrids

Two series of new s-tetrazine derivatives containing 1,3,4-oxadiazole and 1,3,4-thiadiazole rings were synthesized from s-tetrazine-3,6-dicarbohydrazide, triethyl orthoesters and aroyl chlorides. Cyclocondensation reactions for both groups of conjugated arrangements proceeded rapidly and efficiently under microwave irradiation. The obtained compounds exhibited luminescence properties and large quantum yield of emitted photons.

Nickel-Catalyzed Deaminative Acylation of Activated Aliphatic Amines with Aromatic Amides via C-N Bond Activation

Deaminative functionalization of aliphatic primary amines has great synthetic utility. Herein, we describe a Ni-catalyzed reductive deaminative cross-electrophile coupling reaction between Katritzky salts and aromatic amides. This work provides examples of the synthesis of various ketones from alkylpyridinium salts, including both primary and secondary alkylamines. Given its mild reaction conditions and high functional group tolerance, this cross-coupling strategy is expected to be useful for late-stage functionalization of complex compounds.

Palladium-Catalyzed Chlorocarbonylation of Aryl (Pseudo)Halides Through In Situ Generation of Carbon Monoxide

An efficient palladium-catalyzed chlorocarbonylation of aryl (pseudo)halides that gives access to a wide range of carboxylic acid derivatives has been developed. The use of butyryl chloride as a combined CO and Cl source eludes the need for toxic, gaseous carbon monoxide, thus facilitating the synthesis of high-value products from readily available aryl (pseudo)halides. The combination of palladium(0), Xantphos, and an amine base is essential to promote this broadly applicable catalytic reaction. Overall, this reaction provides access to a great variety of carbonyl-containing products through in situ transformation of the generated aroyl chloride. Combined experimental and computational studies support a reaction mechanism involving in situ generation of CO.