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(1S,6R)-8-Boc-3,8-diazabicyclo[4.2.0]octane is a bicyclic organic compound characterized by its molecular formula C12H22N2O2. It features a diazabicyclo[4.2.0]octane ring system with a tert-butoxycarbonyl (Boc) protecting group on the eighth carbon. (1S,6R)-8-Boc-3,8-diazabicyclo[4.2.0]octane's chiral nature, due to the asymmetric carbon centers (1S and 6R), makes it a valuable tool in the synthesis of enantiomerically pure compounds. Its versatility in organic synthesis is further enhanced by the Boc protecting group, which allows for selective manipulation in chemical reactions.

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  • 851526-80-2 Structure
  • Basic information

    1. Product Name: (1S,6R)-8-Boc-3,8-diazabicyclo[4.2.0]octane
    2. Synonyms: (1S,6R)-8-Boc-3,8-diazabicyclo[4.2.0]octane;tert-butyl (1S,6R)-3,8-diazabicyclo[4.2.0]octane-8-carboxylate;(1S,6R)-3,8-Diaza-bicyclo[4.2.0]octane-8-carboxylic acid tert-butyl ester
    3. CAS NO:851526-80-2
    4. Molecular Formula: C11H20N2O2
    5. Molecular Weight: 212.2887
    6. EINECS: N/A
    7. Product Categories: N/A
    8. Mol File: 851526-80-2.mol
  • Chemical Properties

    1. Melting Point: N/A
    2. Boiling Point: 295.4±13.0 °C(Predicted)
    3. Flash Point: N/A
    4. Appearance: /
    5. Density: 1.076±0.06 g/cm3(Predicted)
    6. Refractive Index: N/A
    7. Storage Temp.: 2-8°C
    8. Solubility: N/A
    9. PKA: 10.74±0.20(Predicted)
    10. CAS DataBase Reference: (1S,6R)-8-Boc-3,8-diazabicyclo[4.2.0]octane(CAS DataBase Reference)
    11. NIST Chemistry Reference: (1S,6R)-8-Boc-3,8-diazabicyclo[4.2.0]octane(851526-80-2)
    12. EPA Substance Registry System: (1S,6R)-8-Boc-3,8-diazabicyclo[4.2.0]octane(851526-80-2)
  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: N/A
    4. WGK Germany:
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 851526-80-2(Hazardous Substances Data)

851526-80-2 Usage

Uses

Used in Pharmaceutical Industry:
(1S,6R)-8-Boc-3,8-diazabicyclo[4.2.0]octane is used as a chiral building block for the synthesis of pharmaceuticals. Its chiral centers and Boc protecting group enable the creation of enantiomerically pure compounds, which are essential for the development of effective and selective drugs with minimal side effects.
Used in Agrochemical Industry:
In the agrochemical industry, (1S,6R)-8-Boc-3,8-diazabicyclo[4.2.0]octane serves as a chiral building block for the synthesis of agrochemicals. (1S,6R)-8-Boc-3,8-diazabicyclo[4.2.0]octane's chiral properties and Boc protecting group facilitate the production of enantiomerically pure active ingredients, ensuring targeted pest control and reduced environmental impact.
Used in Fine Chemicals Industry:
(1S,6R)-8-Boc-3,8-diazabicyclo[4.2.0]octane is utilized as a chiral building block in the synthesis of fine chemicals. Its unique structure and Boc protecting group make it a versatile component in the production of high-quality specialty chemicals, such as fragrances, dyes, and other performance-enhancing additives.
Used in Organic Synthesis Research:
(1S,6R)-8-Boc-3,8-diazabicyclo[4.2.0]octane is employed as a research tool in organic synthesis. Its chiral nature and Boc protecting group provide opportunities for exploring novel synthetic routes, developing new reaction mechanisms, and discovering innovative applications in various chemical fields.

Check Digit Verification of cas no

The CAS Registry Mumber 851526-80-2 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 8,5,1,5,2 and 6 respectively; the second part has 2 digits, 8 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 851526-80:
(8*8)+(7*5)+(6*1)+(5*5)+(4*2)+(3*6)+(2*8)+(1*0)=172
172 % 10 = 2
So 851526-80-2 is a valid CAS Registry Number.

851526-80-2SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 19, 2017

Revision Date: Aug 19, 2017

1.Identification

1.1 GHS Product identifier

Product name tert-butyl (1R,6S)-4,7-diazabicyclo[4.2.0]octane-7-carboxylate

1.2 Other means of identification

Product number -
Other names (1S,6R)-TERT-BUTYL 3,8-DIAZABICYCLO[4.2.0]OCTANE-8-CARBOXYLATE

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:851526-80-2 SDS

851526-80-2Relevant articles and documents

Synthesis and structure-activity relationships of 3,8-diazabicyclo[4.2.0] octane ligands, potent nicotinic acetylcholine receptor agonists

Frost, Jennifer M.,Bunnelle, William H.,Tietje, Karin R.,Anderson, David J.,Rueter, Lynne E.,Curzon, Peter,Surowy, Carol S.,Ji, Anquo,Daanen, Jerome F.,Kohlhaas, Kathy L.,Buckley, Michael J.,Henry, Rodger F.,Dyhring, Tino,Ahring, Philip K.,Meyer, Michael D.

, p. 7843 - 7853 (2007/10/03)

A series of potent neuronal nicotinic acetylcholine receptor (nAChR) ligands based on a 3,8-diazabicyclo-[4.2.0]octane core have been synthesized and evaluated for affinity and agonist efficacy at the human high affinity nicotine recognition site (hα4β2) and in a rat model of persistent nociceptive pain (formalin model). Numerous analogs in this series exhibit picomolar affinity in radioligand binding assays and nanomolar agonist potency in functional assays, placing them among the most potent nAChR ligands known for the hα4β2 receptor. Several of the compounds reported in this study (i.e., 24, 25, 28, 30, 32, and 47) exhibit equivalent or greater affinity for the hα4β2 receptor relative to epibatidine, and like epibatidine, many exhibit robust analgesic efficacy in the rat formalin model of persistent pain.

Substituted diazabicycloalkane derivatives

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Page/Page column 28, (2010/02/11)

Compounds of formula (I) [in-line-formulae]Z-Ar1—Ar2??(I) [/in-line-formulae] wherein Z is a diazabicyclic amine, Ar1 is a 5- or 6-membered aromatic ring, and Ar2 is selected from the group consisting of an unsubstituted or substituted 5- or 6-membered heteroaryl ring; unsubstituted or substituted bicyclic heteroaryl ring; 3,4-(methylenedioxy)phenyl; carbazolyl; tetrahydrocarbazolyl; naphthyl; and phenyl; wherein the phenyl is substituted with 0, 1, 2, or 3 substituents in the meta- or para-positions. The compounds are useful in treating conditions or disorders prevented by or ameliorated by α7 nAChR ligands. Also disclosed are pharmaceutical compositions comprising compounds of formula (I) and methods for using such compounds and compositions.

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