63486-45-3

Basic information

• Product Name: 1,3-Cyclopentanediamine,cis-(9CI)
• Synonyms: 1,3-Cyclopentanediamine,cis-(9CI);cyclopentane-1,3-diamine;1,3-CyclopentanediaMine ,cis-;cis-1,3-Cyclopentanediamine;cis-1,3-Diaminocyclopentane;cis-Cyclopentane-1,3-diamine
• CAS NO: 63486-45-3
• Molecular Formula: C₅H₁₂N₂
• Molecular Weight: 100.16
• Product Categories: VARIOUSAMINE
• Mol File: 63486-45-3.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 172.7±8.0 °C(Predicted)
• Appearance: /
• Density: 0.964±0.06 g/cm3(Predicted)
• Storage Temp.: 2-8°C(protect from light)
• PKA: 10.84±0.40(Predicted)
• CAS DataBase Reference: 1,3-Cyclopentanediamine,cis-(9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-Cyclopentanediamine,cis-(9CI)(63486-45-3)
• EPA Substance Registry System: 1,3-Cyclopentanediamine,cis-(9CI)(63486-45-3)

Safety Data

• Hazardous Substances Data: 63486-45-3(Hazardous Substances Data)

Usage

General Description

1,3-Cyclopentanediamine, cis-(9CI) is a colorless organic compound with the chemical formula C5H10N2. It is also known as trans-1,3-diaminocyclopentane or trans-cyclopentane-1,3-diamine. This chemical is a cyclic diamine, which means it contains two amine groups attached to a five-membered ring structure. It is used in organic synthesis as a building block for the construction of various nitrogen-containing compounds. Additionally, it can be used as a ligand in coordination chemistry and in the production of polymers. 1,3-Cyclopentanediamine,cis-(9CI) is not considered to be highly toxic, but it should be handled with care and proper protective equipment due to its potential irritant properties.

Synthetic route

C13H16N4O2 → (1R,3S)-cyclopentane-1,3-diamine (63486-45-3)

Conditions	Yield
With palladium 10% on activated carbon; hydrogen In methanol at 30℃; for 16h;	93%

di-tert-butyl dicarbonate (24424-99-5) + (1R,3S)-cyclopentane-1,3-diamine (63486-45-3) + 3,6-diiodopyridazine (20698-04-8) → C24H40N6O4

Conditions	Yield
Stage #1: (1R,3S)-cyclopentane-1,3-diamine; 3,6-diiodopyridazine With potassium phosphate; copper(l) iodide; N,N-dimethyl-formamide; ethylene glycol for 12h; Heating; Stage #2: di-tert-butyl dicarbonate In ethylene glycol; ethyl acetate at 25℃; for 1h;	74%

methyl 1-(2,2-dihydroxyethyl)-4-oxo-3-[(phenylmethyl)oxy]-1,4-dihydro-2-pyridinecarboxylate (1206102-08-0) + (1R,3S)-cyclopentane-1,3-diamine (63486-45-3) → C20H21N3O3

Conditions	Yield
With acetic acid In toluene at 90℃; for 1.5h;	57%

(1R,3S)-cyclopentane-1,3-diamine (63486-45-3) + C15H14F2N6 + 1,1'-carbonyldiimidazole (530-62-1) → 1-((1R,3S)-3-aminocyclopentyl)-3-(6-((R)-2-(2,5-difluorophenyl)pyrrolidin-1-yl)-[1,2,4]triazolo[4,3-a]pyrazin-3-yl)urea

Conditions	Yield
Stage #1: C15H14F2N6; 1,1'-carbonyldiimidazole With N-ethyl-N,N-diisopropylamine In toluene at 20℃; for 1h; Stage #2: (1R,3S)-cyclopentane-1,3-diamine In toluene for 8h;	56.4%

(1R,3S)-cyclopentane-1,3-diamine (63486-45-3) → N,N'-bis-(3-amino-cyclopentyl)-pyridazine-3,6-diamine

Conditions	Yield
Multi-step reaction with 2 steps 1.1: CuI; K3PO4; DMF / ethylene glycol / 12 h / Heating 1.2: 74 percent / ethyl acetate; ethane-1,2-diol / 1 h / 25 °C 2.1: CF3CO2H / 0.5 h / 0 °C View Scheme

(1R,3S)-cyclopentane-1,3-diamine (63486-45-3) → N,N'-bis-[3-(tetrazolo[1,5-b]pyridazin-6-ylamino)-cyclopentyl]-pyridazine-3,6-diamine

Conditions	Yield
Multi-step reaction with 3 steps 1.1: CuI; K3PO4; DMF / ethylene glycol / 12 h / Heating 1.2: 74 percent / ethyl acetate; ethane-1,2-diol / 1 h / 25 °C 2.1: CF3CO2H / 0.5 h / 0 °C 3.1: 0.094 g / K2CO3 / dimethylformamide / 8 h / 95 °C View Scheme

(1R,3S)-cyclopentane-1,3-diamine (63486-45-3) → C46H80N12P2

Conditions	Yield
Multi-step reaction with 4 steps 1.1: CuI; K3PO4; DMF / ethylene glycol / 12 h / Heating 1.2: 74 percent / ethyl acetate; ethane-1,2-diol / 1 h / 25 °C 2.1: CF3CO2H / 0.5 h / 0 °C 3.1: 0.094 g / K2CO3 / dimethylformamide / 8 h / 95 °C 4.1: 60 percent / acetonitrile / 3 h / Heating View Scheme

(1R,3S)-cyclopentane-1,3-diamine (63486-45-3) → C60H86N12O8

Conditions	Yield
Multi-step reaction with 5 steps 1.1: CuI; K3PO4; DMF / ethylene glycol / 12 h / Heating 1.2: 74 percent / ethyl acetate; ethane-1,2-diol / 1 h / 25 °C 2.1: CF3CO2H / 0.5 h / 0 °C 3.1: 0.094 g / K2CO3 / dimethylformamide / 8 h / 95 °C 4.1: 60 percent / acetonitrile / 3 h / Heating 5.1: toluene / 24 h / Heating View Scheme

4,7-dichloroquinoline (86-98-6) + dimethanesulphonate + (1R,3S)-cyclopentane-1,3-diamine (63486-45-3) → cis-N,N'-bis-(7-chloroquinolin-4-yl)-cyclopentane-1,3-diamine

Conditions	Yield
With methanesulfonic acid; triethylamine In diethyl ether; acetic acid

(1R,3S)-cyclopentane-1,3-diamine (63486-45-3) + C12H8ClN3O → C17H19N5O

Conditions	Yield
With triethylamine In ethanol at 120℃; for 1h;

5-chloro-3-(4-methoxy-phenyl)-3H-[1,2,3]triazolo[4,5-d]pyrimidine (1448694-38-9) + (1R,3S)-cyclopentane-1,3-diamine (63486-45-3) → (1R,3S)-N-[3-(4-methoxyphenyl)-3H-[1,2,3]triazolo[4,5-d]pyrimidin-5-yl]cyclopentane-1,3-diamine

Conditions	Yield
In 2-methoxy-ethanol at 80℃; for 3h;

5-chloro-3-(4-methoxy-phenyl)-3H-[1,2,3]triazolo[4,5-d]pyrimidine (1448694-38-9) + (1R,3S)-cyclopentane-1,3-diamine (63486-45-3) → (1S,3R)-N-[3-(4-methoxyphenyl)-3H-[1,2,3]triazolo[4,5-d]pyrimidin-5-yl]cyclopentane-1,3-diamine

Conditions	Yield
In 2-methoxy-ethanol at 80℃; for 3h;

Upstream product

• 1013640-20-4 cyclopentane-1,3-dioxime 
• 3859-41-4 1,3-cyclopentadione 
• 59995-47-0 4-Hydroxycyclopent-2-enone 
• 98-00-0 (2-furyl)methyl alcohol 

Relevant articles and documents

Bio-based synthesis of cyclopentane-1,3-diamine and its application in bifunctional monomers for poly-condensation

A novel and green route for the synthesis of cyclopentane-1,3-diamine (CPDA) from hemicellulosic feedstock is established in this work. Through many explorations and optimizations, the single successful multi-step synthesis was found to comprise: (1) the Piancatelli rearrangement of furfuryl alcohol to 4-hydroxycyclopent-2-enone (4-HCP), (2) a highly improved isomerization of4-HCPinto cyclopentane-1,3-dione (CPDO) using the Ru Shvo catalyst, (3) conversion ofCPDOinto cyclopentane-1,3-dioxime (CPDX), and (4) a mild oxime hydrogenation ofCPDXover Rh/C to afford the desiredCPDA. In addition, diastereomerically purecis- andtrans-isomers ofCPDAwere reacted with (A) bio-based lactones, and (B) 5-(hydroxymethyl)furfural (HMF) to synthesize novel bifunctional diol monomers with internal amide and imine groups, respectively. Monomer5, derived using γ-valerolactone (GVL), was successfully applied in the synthesis of polyurethanes.

3-Anilino-2,4-diazabicyclo[3.2.1]octenes

Novel 3-anilino-2,4-diazabicyclo[3.2.1]octenes, physiologically tolerable acid addition salts thereof and method of preparing same are described. These compounds are useful as tranquilizers, diuretics and antihypertensives.