16396-49-9

Usage

Functional Groups

Hydrazine, carboxylic acid, ester, phenylmethyl

Molecular Weight

287.32 g/mol

Appearance

Colorless to pale yellow solid or liquid

Solubility

Soluble in organic solvents like ethanol, methanol, and acetone

Melting Point

Not readily available, but expected to be low due to the ester functional group

Boiling Point

Not readily available, but expected to be relatively high due to the molecular size and complexity

Density

Not readily available, but expected to be higher than water due to the molecular size and complexity

Reactivity

Reacts with nucleophiles, electrophiles, and other reagents in organic synthesis

Uses

Building block in the synthesis of various pharmaceuticals and organic molecules

Applications

Potential use in the development of new drugs and materials

Safety Precautions

Proper handling and safety measures should be followed to minimize exposure and potential hazards

Storage

Store in a cool, dry, and well-ventilated area, away from heat, sparks, and open flames

Stability

Stable under normal conditions, but may decompose upon exposure to heat, light, or strong oxidizing agents

Hazards

Potential irritant, harmful if inhaled, swallowed, or absorbed through the skin

Disposal

Dispose of in accordance with local, national, and international regulations for chemical waste

Regulatory Status

May be subject to specific regulations depending on the intended use and location

Synonyms

N-benzyl-N',N'-diethylhydrazinedicarboxamide, 1-(phenylmethyl)-1,2-hydrazinedicarboxylic acid diethyl ester

Upstream product

• 4143-61-7 diethyl diazodicarboxylate 
• 110-22-5 diacetyl peroxide 
• 110-82-7 cyclohexane 
• 108-88-3 toluene 
• 1972-28-7 diethylazodicarboxylate 
• 94-36-0 dibenzoyl peroxide 
• 100-51-6 benzyl alcohol 
• 1694-84-4 tribenzylborane 
• 868-85-9 Dimethyl phosphite 
• 4114-28-7 diethyl hydrazodicarboxylate 
• 100-39-0 benzyl bromide 

Downstream Products

• 121643-88-7 benzyl-hydrazine-N,N'-dicarboxylic acid dimethyl ester 
• 1174758-28-1 diethyl 2-benzyl-1-((R)-hydroxymethylallyl)hydrazine-1,2-dicarboxylate 

Relevant academic research and scientific papers

An unusual reaction of dimethyl azodicarboxylate with H-dimethylphosphonate

When the commonly used phosphorus components of the cocktail of the classical Mitsunobo reaction are changed from triphenylphosphine and trialkylphosphite to H-dimethylphosphonate, the course of the reaction changes and leads to products arising from the

Selective Functionalization of Hydrocarbons Using a ppm Bioinspired Molecular Tweezer via Proton-Coupled Electron Transfer

An expanded porphyrin-biscopper hexaphyrin was introduced as a bioinspired molecular tweezer to co-catalyze functionalization of C(sp3)-H bonds. Theoretical and experimental investigations suggested that the biscopper hexaphyrin served as a molecular tweezer to mimic the enzymatic orientation/proximity effect, efficiently activating the N-hydroxyphthalimide (NHPI) via light-free proton-coupled electron transfer (PCET), at an exceptionally low catalyst loading of 10 mol ppm. The resulting N-oxyl radical (PINO) was versatile for chemoselective C-H oxidation and amination of hydrocarbons.

Synthesis of benzyl hydrazine derivatives: Via amination of benzylic C(sp3)-H bonds with dialkyl azodicarboxylates

A novel synthesis of benzyl hydrazines through oxidative amination of benzylic C-H bonds has been developed. The resulting aminated products are accessed directly from the reaction of alkylarenes with dialkyl/diphenyl azodicarboxylates using Cu2O/Phen as the catalytic system. The reaction proceeded smoothly and a decent range of N-substituted hydrazides was synthesized in acceptable to good yields. Both primary and secondary sp3 C-H sources afford only monoamination products.

Convenient synthesis of monobenzylated hydrazides via aqueous zinc-mediated addition reactions

Addition of substituted benzyl bromides to dialkyl azodicarboxylates under aqueous zinc-mediated addition conditions occurs readily to afford monobenzylated hydrazides in good to excellent yields. The reaction is tolerant of a variety of substituents on the benzyl bromide ring. Several dialkyl azodicarboxylates were successfully tested under the reaction conditions. The limitations of the reaction are also addressed.

Radical amination of C(sp3)-H bonds using N -hydroxyphthalimide and dialkyl azodicarboxylate

A direct conversion of C(sp3)-H bonds to C(sp3)-N bonds has been achieved by utilizing catalytic N-hydroxyphthalimide (NHPI) and stoichiometric dialkyl azodicarboxylate. NHPI functions as a precursor of the electron-deficient phthalimide N-oxyl radical (PINO) to abstract hydrogens, and dialkyl azodicarboxylate acts as a trapping agent of the resultant carbon radical to generate the hydrazine derivatives. This C-H amination proceeds in a highly chemoselective manner with a wide applicability to functionalize benzylic, propargylic, and aliphatic C-H bonds. Furthermore, the obtained hydrazine compounds were readily converted to the corresponding carbamates or amines. Hence, the present protocol for direct introduction of the nitrogen functionality serves as a powerful tool for efficient construction of nitrogen-substituted natural products and pharmaceuticals.

Synthesis of arylhydrazines by reaction of arylbromides with DEAD via sonochemical Barbier reaction

A series of arylhydrazines was synthesized from the reaction mixture of Mg powder, 1,2-dibromoethane, aryl bromide and DEAD (diethyl azodicarboxylate) in THF under ultrasound. This sonochemical Barbier reaction provides an efficient and inexpensive prepar

Dynamic kinetic asymmetrie allylation of hydrazines and hydroxylamines

Hydrazines and hydroxylamines have been found to be excellent nucleophiles for the palladium-catalyzed dynamic asymmetric allylic amination of vinyl epoxide, with good yields and enantioselectivities of up to 97% ee. This method is applicable to acyclic a