4-bromobutyl Nitrate

Base Information

• Chemical Name: 4-bromobutyl Nitrate
• CAS No.: 146563-40-8
• Molecular Formula: C4H8 Br N O3
• Molecular Weight: 198.016
• European Community (EC) Number: 823-981-4
• DSSTox Substance ID: DTXSID90439582
• Wikidata: Q82255569
• Mol file: 146563-40-8.mol

Synonyms:4-bromobutyl Nitrate;4-bromobutylnitrate;146563-40-8;4-nitrooxybutyl bromide;1-bromo-4-(nitrooxy)butane;SCHEMBL1319845;DTXSID90439582;IKDHVMDABUMCLO-UHFFFAOYSA-N;AKOS040824550;CS-0498368;EN300-19324306;F9995-2702

Chemical Property of 4-bromobutyl Nitrate

Chemical Property:

• PSA: 55.05000
• LogP: 1.89300
• Storage Temp.: Refrigerator, under inert atmosphere
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 196.96876
• Heavy Atom Count: 9
• Complexity: 82.4

Purity/Quality:

99% ^*data from raw suppliers

4-?Bromo-1-?butanol1-?Nitrate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C(CCBr)CO[N+](=O)[O-]
• Uses: 4-bromobutyl nitrate is an intermediate in synthesizing Latanoprostene Bunod (L177335). It is a derivative of Latanoprost and is used in the treatment of interocular pressure.

Technology Process of 4-bromobutyl Nitrate

There total 2 articles about 4-bromobutyl Nitrate 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: 100.0%

4-Bromo-1-butanol (33036-62-3) → 4-(nitrooxy)butyl bromide (146563-40-8)

Guidance literature:

With sulfuric acid; nitric acid; at 0 ℃; for 1h;

DOI:10.1021/jm00059a004

Reference yield:

→ 4-(nitrooxy)butyl bromide (146563-40-8)

Guidance literature:

Reference yield: 73.0%

(2S)-2-(6-methoxy(2-naphthyl))propanoic acid (22204-53-1) + 4-(nitrooxy)butyl bromide (146563-40-8) → naproxcinod (163133-43-5,170591-17-0)

Guidance literature:

(2S)-2-(6-methoxy(2-naphthyl))propanoic acid; With potassium hydrogencarbonate; In DMF (N,N-dimethyl-formamide); at 50 - 60 ℃; for 1.5h;

4-(nitrooxy)butyl bromide; With potassium iodide; In DMF (N,N-dimethyl-formamide); at 20 ℃; for 25h;

upstream raw materials:

4-Bromo-1-butanol

Downstream raw materials:

(E)-4-(nitrooxy)butyl 3-(4-hydroxy-3-methoxyphenyl)acrylate

4-(nitrooxy)butyl [1α(Z),2β(R),3α,5α]-7-[3,5-dihydroxy-2-((3R)-3-hydroxy-5-phenylpentyl)cyclopentyl]-5-heptenoate

4-(nitrooxy)butyl 4-(aminosulfonyl)benzoate

5-(4-carboxyl(4-nitrooxybutyl)benzenesulphonamido)-1,3,4-thiadiazole-2-sulphonamide

Refernces

• 1、 -. "NITRIC OXIDE RELEASING PROSTAGLANDIN DERIVATIVES FOR TREATING NORMAL TENSION GLAUCOMA". Page/Page column 13; 14. . Retrieved 2018/05/27.
• 2、 -. "NITRATE ESTERS OF CARBONIC ANHYDRASE INHIBITORS". Page/Page column 64. . Retrieved 2008/12/06.