765-30-0 Usage
Description
Cyclopropylamine is an organic compound with the chemical formula C3H7NH2. It is a colorless liquid with a strong, fishy odor and is highly reactive due to the presence of the cyclopropane ring and the amine group. Cyclopropylamine is a versatile building block in organic synthesis and has various applications in different industries.
Uses
Used in Pharmaceutical Industry:
Cyclopropylamine is used as a key intermediate in the synthesis of various pharmaceutical compounds. It is used in the preparation of N-[4-(4-fluoro)phenyl-2-aminothiazol-5-yl]pyrimidin-2-yl-alkylamine derivatives, which are potential therapeutic agents with potential applications in the treatment of various diseases.
Used in Chemical Industry:
Cyclopropylamine is used as a reagent in the synthesis of various organic compounds, including pharmaceuticals, agrochemicals, and other specialty chemicals. Its unique cyclopropane ring and amine group make it a valuable building block for the development of new molecules with specific properties and applications.
Used in Coordination Chemistry:
Cyclopropylamine is used in the preparation of coordination complexes, such as Pt(CPA)2(bismethylthiomethylenepropanedioate) and Pt(CPA)2(bisethylthiomethylenepropanedioate). These complexes have potential applications in various fields, including catalysis, materials science, and medicinal chemistry, due to their unique structural and electronic properties.
Preparation
Cyclopropylamine is synthesized from 1,3-propanediol by bromination, cyanation, cyclization, amidation, and Hoffmann rearrangement. It is also synthesized with γ-butyrolactone and isopropanol by five steps of ring-opening esterification, cyclization, hydrolysis, acylation and Hofmann degradation.
Biochem/physiol Actions
Cyclopropylamine inactivates cytochrome P450 enzymes by a mechanism involving initial one-electron oxidation at nitrogen followed by scission of the cyclopropane ring leading to covalent modification of the enzyme. It is a mechanism-based inhibitor of quinoprotein methylamine dehydrogenase from Paracoccus denitrificans.
Purification Methods
It has been isolated as the benzamide m 100.6-101.0o (from aqueous EtOH). It forms a picrate m 149o (from EtOH/pet ether) from which the free base can be recovered using a basic ion-exchange resin and can then be distilled through a Todd column (p 11) using an automatic still head which only collects products boiling below 51o/atm. Polymeric materials if present will boil above this temperature. The hydrochloride has m 85-86o [Roberts & Chambers J Am Chem Soc 73 5030 1951, Jones J Org Chem 9 484 1944, Emmons J Am Chem Soc 79 6522 1957]. [Beilstein 12 IV 3.]
Check Digit Verification of cas no
The CAS Registry Mumber 765-30-0 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 7,6 and 5 respectively; the second part has 2 digits, 3 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 765-30:
(5*7)+(4*6)+(3*5)+(2*3)+(1*0)=80
80 % 10 = 0
So 765-30-0 is a valid CAS Registry Number.
InChI:InChI=1/C3H7N/c4-3-1-2-3/h3H,1-2,4H2
765-30-0Relevant articles and documents
The Insertion Reaction of NH Singlet Radicals into the C-H Bonds of Cyclopropane and Isobutane in the Liquid Phase
Hamada, Jun-ich,Tsunashima, Shigeru,Sato, Shin
, p. 1739 - 1742 (1982)
Hydrogen azide was photolyzed in liquid cyclopropane at the temperature of Dry Ice-methanol.The main products observed were nitrogen, cyclopropylamine, and ammonia.The relative yields of the products depended slightly on the concentration of hydrogen azide.The results were then compared with those obtained with paraffin and olefin.The isobutane solution of hydrogen azide was photolyzed at 0 deg C.The products observed were the same as those obtained at the temperature of Dry-Ice-methanol.The relative yields of the products and the concentration dependence, however, were different.
Method for preparing amine through catalytic reduction of nitro compound by cyclic (alkyl) (amino) carbene chromium complex
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Paragraph 0015, (2021/04/17)
The cyclic (alkyl) (amino) carbene chromium complex is prepared from corresponding ligand salt, alkali and CrCl3 and used for catalyzing pinacol borane to reduce nitro compounds in an ether solvent under mild conditions to generate corresponding amine. The method for preparing amine has the advantages of cheap and accessible raw materials, mild reaction conditions, wide substrate application range, high selectivity and the like, and is simple to operate.
NHC-based coordination polymers as solid molecular catalysts for reductive amination of biomass levulinic acid
Sun, Zheming,Chen, Jiangbo,Tu, Tao
, p. 789 - 794 (2017/08/18)
A class of robust solid molecular NHC-based catalysts were readily fabricated via self-assembly from a p-phenylene-bridged bis-benzimidazolium salt with selected metal precursors. Among them, the NHC-Ru polymer demonstrated high catalytic activity and excellent stability as a solid molecular catalyst for the solvent-free reductive amination of biomass levulinic acid with inexpensive ammonium formate, furnishing a challenging unprotected 5-methyl-2-pyrrolidone quantitatively at a 0.15 mol% catalyst loading. The solid catalyst was readily recovered and reused for 37 runs without obvious loss of activity. Remarkably, a TON value up to 6.7 × 104 was achieved in a molar-scale reaction with a catalyst loading at 0.001 mol%. Inspired by the results of a preliminary mechanistic study, notably, one-pot tandem reductive reactions of LA with aldehydes or ketones were successfully developed, affording a variety of structurally intriguing and functional N-substituted 5-methyl-2-pyrrolidones in high chemo-selectivity with good to excellent yields.
