Cholest-5-ene, 3-bromo-, (3beta)-

Base Information

• Chemical Name: Cholest-5-ene, 3-bromo-, (3beta)-
• CAS No.: 516-91-6
• Molecular Formula: C27H45 Br
• Molecular Weight: 449.558
• DSSTox Substance ID: DTXSID90862098
• Mol file: 516-91-6.mol

Synonyms:3-Bromocholest-5-ene;Cholest-5-ene, 3-bromo-, (3beta)-;3-bromo-10,13-dimethyl-17-(6-methylheptan-2-yl)-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene;3beta-Bromocholest-5-ene;EINECS 208-227-9;SCHEMBL19607942;DTXSID90862098;(3S,8S,9S,10R,13R,14S,17R)-3-bromo-10,13-dimethyl-17-((R)-6-methylheptan-2-yl)-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene;(3S,8S,9S,10R,13R,14S,17R)-3-bromo-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene;AKOS024319518;(3R,8S,9S,10R,13R,14S,17R)-3-Bromo-10,13-dimethyl-17-[(R)-6-methyl-2-heptanyl]-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene;SY292575;FT-0623757

Chemical Property of Cholest-5-ene, 3-bromo-, (3beta)-

Chemical Property:

• Vapor Pressure: 4E-09mmHg at 25°C
• Melting Point: 98 °C
• Boiling Point: 486°Cat760mmHg
• Flash Point: 244.1°C
• PSA: 0.00000
• Density: 1.1g/cm³
• LogP: 8.79130
• Storage Temp.: −20°C
• XLogP3: 10
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 5
• Exact Mass: 448.27046
• Heavy Atom Count: 28
• Complexity: 591

Purity/Quality:

98%,99%, ^*data from raw suppliers

CholesterylBromide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)CCCC(C)C1CCC2C1(CCC3C2CC=C4C3(CCC(C4)Br)C)C
• Uses: Cholesteryl Bromide can be used for anti-nociceptive activity.

Technology Process of Cholest-5-ene, 3-bromo-, (3beta)-

There total 17 articles about Cholest-5-ene, 3-bromo-, (3beta)- which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

cholesterol (765935-41-9) → 3-bromocholest-5-ene (516-91-6)

Guidance literature:

With Silphos; bromine; In acetonitrile; for 0.666667h; Heating;

DOI:10.1016/j.tet.2005.01.115

Reference yield: 95.0%

2-[(3S,8S,9S,10R,13R,14S,17R)-17-((R)-1,5-Dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yloxysulfonyl]-benzoic acid 2-(2-methoxy-ethoxy)-ethyl ester (888021-88-3) → (3S,8S,9S,10R,13R,14S,17R)-3-Bromo-17-((R)-1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene (516-91-6)

Guidance literature:

With titanium(IV) bromide; In dichloromethane; at -78 ℃; for 0.25h; Inert atmosphere;

DOI:10.1002/anie.200802472

Reference yield: 92.0%

cholesterol mesylate (3381-54-2) → (3S,8S,9S,10R,13R,14S,17R)-3-Bromo-17-((R)-1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene (516-91-6)

Guidance literature:

With trimethylsilyl bromide; boron trifluoride diethyl etherate; In dichloromethane; at 22 ℃; for 1h; Inert atmosphere;

DOI:10.1021/ol802343z

upstream raw materials:

cholesterol

3α,5α-cyclo-cholest-6-ene

cholesteryl p-toluenesulfonate

2,3,4,6-tetra-O-acetyl-D-glucopyranosyl bromide

Downstream raw materials:

3,5-cholestadiene

cholesteryl methyl ether

3β.5-dibromo-5α-cholestane

(3S,8S,9S,10R,13R,14S,17R)-17-((R)-1,5-Dimethyl-hexyl)-3-(diphenyl-phosphinoyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene

Refernces

• 1、 Liu, Yajun,Xu, Yongnan,Jung, Sun Ho,Chae, Junghyun. "A facile and green protocol for nucleophilic substitution reactions of sulfonate esters by recyclable ionic liquids [bmim][X]". supporting information. p. 2692 - 2698,7. Retrieved 2012/12/12.
• 2、 Van Kalkeren, Henri A.,Leenders, Stefan H. A. M.,Hommersom, C. Rianne A.,Rutjes, Floris P. J. T.,Van Delft, Floris L.. "In situ phosphine oxide reduction: A catalytic appel reaction". supporting information; experimental part. p. 11290 - 11295. Retrieved 2011/10/19.