Isopropyl-hydrazine

• CAS: 2257-52-5
• Catalog Number: ACM2257525
• Category: Other Products; Main Products
• Molecular Weight: 74.13
• Molecular Formula: C₃H₁₀N₂
• Synonyms: N-isopropylhydrazine; Isopropyl-hydrazin; prop-2-ylhydrazine; 1-Isopropylhydrazine; isopropyl hydrazine
• IUPAC Name: propan-2-ylhydrazine
• SMILES: CC(C)NN
• InChI Key: KJAQRHMKLVGSCG-UHFFFAOYSA-N
• Boiling Point: 120.1ºC at 760mmHg
• Flash Point: 24.8ºC
• Appearance: Liquid
• Exact Mass: 74.08440
• H-Bond Acceptor: 2
• H-Bond Donor: 2

Case Study

Isopropyl-hydrazine in the Convergent Synthesis of a Dual 5HT7/5HT2 Antagonist

Liang, Jimmy T., et al. Organic Process Research & Development 15.4 (2011): 876-882.

Developing efficient routes to complex pharmaceuticals like 3-(4-fluorophenyl)-2-isopropyl-2,4,5,6,7,8-hexahydropyrazolo[3,4-d]azepine (1), a potent 5HT7/5HT2 dual antagonist, requires strategic reagent selection. Isopropyl-hydrazine proved critical for constructing a key tetra-substituted pyrazole intermediate.
Overall Synthetic Strategy
Key aspects of this route include: (a) the regioselective synthesis of tetra-substituted pyrazole 6a through the reaction of an N-monosubstituted hydrazone 4a with a complex nitroolefin 5b, and (b) an innovative Pd-catalyzed hydrogenation technique that executes the four-step, ring-closing reductive amination process in a remarkable one-pot operation, resulting in compound 1 with outstanding overall yields.
Synthesis Details of Hydrazone 4a from Isopropyl Hydrazine
To a solution of isopropyl hydrazine hydrochloride (92.4 g, 0.84 mol) and benzyl (3-oxopropyl)carbamate (173 g, 0.84 mol) in isopropyl alcohol (1.7 L) was added triethylamine (140 mL, 1.0 mol) dropwise over 20 min to form a thick paste of white solids. This was heated to reflux for 3 h. Upon cooling and concentration in vacuo (30 Torr, 40°C) the residue was diluted with ethyl acetate (700 mL), extracted with water (3 × 500 mL) and brine (300 mL), dried over MgSO4 and filtered. Solvent removal yielded the product hydrazone 4a as a light-yellow oil in 98% yield (216 g, 0.82 mol).

Application of Isopropyl hydrazine in the Synthesis of Pyrazolo[3,4-d]Pyrimidine RET Inhibitors

Wang, Chengyan, et al. Bioorganic & medicinal chemistry letters 27.11 (2017): 2544-2548.

This work reported the synthesis of three series of pyrazolo[3,4-d]pyrimidine derivatives and evaluates their role as RET kinase inhibitors. Among them, isopropyl hydrazine hydrochloride was used as one of the key raw materials for the synthesis of compounds 21a-o.
4-Amino-6-chloropyrimidine-5-carbonitrile reacts with isopropyl hydrazine hydrochloride to generate compound 20. 20 is acylated with the corresponding acyl chloride to obtain 21a-o.
Compounds 21a-o comprise a set of 1H-pyrazolo[3,4-d]pyrimidines with a C3-amido group. As indicated in Table 2, cyclopropanecarboxamides 21a-c exhibited minimal activity against RET. Benzamide 21d also demonstrated a lack of potency, while heterocyclic amides 21e-i showed moderate activity, with approximately 50% inhibition at 10 nM concentrations. Carboxamides containing five-membered heterocycles were slightly more effective than their six-membered counterparts (21f, g, i, j vs. 21a-e). Compounds 21j (5-cyclopropylisoxazole) and 21l (furan-isoxazole) maintained significant inhibition of RET. The diminished activity of benzo[d]isoxazole 21k and 5-phenylisoxazoles 21m-o suggested that RET kinase's hydrophobic pocket is somewhat narrow, accommodating only a limited range of substituents.

Custom Q&A

What is the molecular formula of Isopropyl-hydrazine?

The molecular formula of Isopropyl-hydrazine is C3H10N2.

What are the synonyms for Isopropyl-hydrazine?

The synonyms for Isopropyl-hydrazine include isopropylhydrazine, 1-Isopropylhydrazine, and propan-2-ylhydrazine.

What is the molecular weight of Isopropyl-hydrazine?

The molecular weight of Isopropyl-hydrazine is 74.13 g/mol.

When was Isopropyl-hydrazine created?

Isopropyl-hydrazine was created on March 26, 2005.

What is the IUPAC name of Isopropyl-hydrazine?

The IUPAC name of Isopropyl-hydrazine is propan-2-ylhydrazine.

What is the InChI key of Isopropyl-hydrazine?

The InChI key of Isopropyl-hydrazine is KJAQRHMKLVGSCG-UHFFFAOYSA-N.

What is the Canonical SMILES of Isopropyl-hydrazine?

The Canonical SMILES of Isopropyl-hydrazine is CC(C)NN.

What is the CAS number of Isopropyl-hydrazine?

The CAS number of Isopropyl-hydrazine is 2257-52-5.

What is the UNII of Isopropyl-hydrazine?

The UNII of Isopropyl-hydrazine is W2Q1ED74SJ.

What is the XLogP3-AA value of Isopropyl-hydrazine?

The XLogP3-AA value of Isopropyl-hydrazine is -0.2.