125735-40-2

Basic information

• Product Name: 1-Benzhydryl-3-iodoazetidine
• Synonyms: 1-Benzhydryl-3-iodoazetidine;N-Benzhydryl-3-iodoazetidine;Azetidine, 1-(diphenylMethyl)-3-iodo-;3-Iodo-N-benzhydrylazetidine
• CAS NO: 125735-40-2
• Molecular Formula: C₁₆H₁₆IN
• Molecular Weight: 349.22
• Mol File: 125735-40-2.mol
• Article Data: 5

Chemical Properties

• Melting Point: 101～102℃
• Boiling Point: 377℃
• Flash Point: 182℃
• Appearance: /
• Density: 1.55
• Storage Temp.: 2-8°C(protect from light)
• PKA: 6.16±0.10(Predicted)
• CAS DataBase Reference: 1-Benzhydryl-3-iodoazetidine(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Benzhydryl-3-iodoazetidine(125735-40-2)
• EPA Substance Registry System: 1-Benzhydryl-3-iodoazetidine(125735-40-2)

Safety Data

• Hazardous Substances Data: 125735-40-2(Hazardous Substances Data)

Usage

Uses

1-Benzhydryl-3-iodoazetidine is a useful research reagent used in the synthetic preparation of other pharmacologically active molecules.

Upstream product

• 18621-17-5 1-(diphenylmethyl)-3-hydroxyazetidine 
• 33301-41-6 1-benzhydryl-3-azetidinyl methanesulfonate 

Downstream Products

• 231953-75-6 3-(3-(Trifluoromethyl)phenyl)-1-(diphenylmethyl)azetidine 

Relevant articles and documents

Counterion-Induced Asymmetric Control in Ring-Opening of Azetidiniums: Facile Access to Chiral Amines

Counterion-induced stereocontrol is a powerful tool in organic synthesis. However, such enantiocontrol on tetrahedral ammonium cations remains challenging. Described here is the first example of using chiral anion phase-transfer catalysis to achieve intermolecular ring-opening of azetidiniums with excellent enantioselectivity (up to 97 % ee). Precise control over the formation and reaction of the chiral ion pair as well as inhibition of the background reaction by the biphasic system is key to the success of the reaction.

Substituted benzoylpiperidine derivatives and their use as Neurokinin antagonists

The present invention provides a compound of the formula:- or a pharmaceutically acceptable acid addition salt thereof, whereinAr is phenyl substituted by 1 or 2 substituent(s) each independently selected from fluoro and chloro;X is NSO2(C1-C4 alkyl), NSO2(halo(C1-C4 alkyl)) or O;m is 0 or 1 ;n is 1 or 2;p is 1 or 2;q is 1 or 2; and r is 1 or 2, together with processes for the preparation of, intermediates used in the preparation of, compositions containing and uses of, such derivatives. The compounds have tachykinin receptor antagonist activity.

Synthesis and X-ray Crystal Structure of 1,3,3-Trinitroazetidine

1,3,3-Trinitroazetidine (1) was synthesized and its structure elucidated by X-ray crystallography.Reaction of 1-tert-butyl-3-((methylsulfonyl)oxy)azetidine (3a) with sodium nitrite gave 1-tert-butyl-3-nitroazetidine (4a), which was converted to 1-tert-butyl-3,3-dinitroazetidine (5a) by oxidative nitration.Nitrolysis of 5a with acetyl nitrate gave 1. 1-Benzhydryl-3,3-dinitroazetidine (5b) did not undergo a similar nitrolysis.Single-crystal X-ray analysis of 1 showed that the ring is puckered, with a dihedral angle of 13.6(5) deg between the C-C-C and C-N-C planes, and that the nitramino group exhibits an unusually high (39.4 deg) out-of-plane deformation.A structural optimization with MNDO reproduced the ring pucker and the nitramino bend to within 5 deg.The large bend at the ring nitrogen atom indicates sp3 rather than sp2 for its hybridization.However, the N-N bond length, 1.351(6) Angstroem, falls in the normal range for planar (sp2) nitramines and is ca. 0.1 Angstroem shorter than N-N bonds previously observed in bent nitramines.