(R)-3-Bromopropane-1,2-diol

Base Information

• Chemical Name: (R)-3-Bromopropane-1,2-diol
• CAS No.: 14437-88-8
• Molecular Formula: C3H7 Br O2
• Molecular Weight: 154.991
• Hs Code.: 2905590090
• European Community (EC) Number: 886-390-0
• DSSTox Substance ID: DTXSID001309594
• Nikkaji Number: J72.462I
• Mol file: 14437-88-8.mol

Synonyms:(R)-3-Bromopropane-1,2-diol;14437-88-8;(2R)-3-bromopropane-1,2-diol;(R)-1-BROMO-2,3-DIHYDROXYPROPANE;(2r)-3-bromo-1,2-propanediol;SCHEMBL2945693;SIBFQOUHOCRXDL-VKHMYHEASA-N;DTXSID001309594;AKOS006279698;EN300-2966779

Chemical Property of (R)-3-Bromopropane-1,2-diol

Chemical Property:

• Boiling Point: 102 °C(Press: 7 Torr)
• PKA: 13.07±0.20(Predicted)
• PSA: 40.46000
• Density: 1.789±0.06 g/cm3(Predicted)
• LogP: -0.26550
• XLogP3: -0.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 153.96294
• Heavy Atom Count: 6
• Complexity: 32

Purity/Quality:

99% ^*data from raw suppliers

(R)-1-BROMO-2,3-DIHYDROXYPROPANE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C(C(CBr)O)O
• Isomeric SMILES: C([C@H](CBr)O)O

Technology Process of (R)-3-Bromopropane-1,2-diol

There total 16 articles about (R)-3-Bromopropane-1,2-diol 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: 93.0%

1,2-Epoxy-3-bromopropane (3132-64-7,82584-73-4) → (S)-epichlorohydrin (67843-74-7,24969-06-0,13403-37-7) + (2R)-3-bromo-1,2-propanediol (14437-88-8)

Guidance literature:

With (R,R)-Jacobsen catalyst; water; In tetrahydrofuran; at 4 ℃; for 24h;

DOI:10.1021/jo981332d

Reference yield: 90.0%

1,2-Epoxy-3-bromopropane (3132-64-7,82584-73-4) → (2R)-3-bromo-1,2-propanediol (14437-88-8) + (R)-3-bromo-1,2-epoxypropane (51594-57-1,82584-73-4) + 1-bromo-2,3-epoxypropane (96479-96-8,82584-73-4)

Guidance literature:

With [(R,R)-N,N'-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediaminato^(2-)]cobalt(III) acetate; water; In tetrahydrofuran; at 0 ℃;

DOI:10.1021/ja016737l

Reference yield: 90.0%

1,2-Epoxy-3-bromopropane (3132-64-7,82584-73-4) → (2R)-3-bromo-1,2-propanediol (14437-88-8) + 1-bromo-2,3-epoxypropane (96479-96-8,82584-73-4)

Guidance literature:

With [(R,R)-N,N'-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediaminato^(2-)]cobalt(III) acetate; water; In tetrahydrofuran; at 4 ℃; for 48h;

DOI:10.1021/ja016737l

upstream raw materials:

2,3-Dibromopropan-1-ol

(R)-(2,2-dimethyl-1,3-dioxolan-4-yl)methyl bromide

S-(-)-2,2'-dinitrobiphenyl-6,6'-dicarbonsaeure-diallylester

allyl bromide

Downstream raw materials:

(R)-oxiranemethanol

(R)-4-bromomethyl-2-methyl-2-ethyl-1,3-dioxolane

Toluene-4-sulfonic acid (R)-3-bromo-2-hydroxy-propyl ester

Refernces

• 1、 Dandachi, Hiba,Nasrallah, Houssein,Ibrahim, Farah,Hong, Xiang,Mellah, Mohamed,Jaber, Nada,Schulz, Emmanuelle. "Chiral calix-salen cobalt complexes, catalysts for the enantioselective dynamic hydrolytic kinetic resolution of epibromohydrin". . p. 457 - 462. Retrieved 2014/12/10.
• 2、 Berkessel, Albrecht,Ertuerk, Erkan. "Hydrolytic kinetic resolution of epoxides catalyzed by chromium(III)-endo, endo-2,5-diaminonorbornane-salen [Cr(III)-DIANANE-salen] complexes. Improved activity, low catalyst loading". . p. 2619 - 2625. Retrieved 2007/10/03.