2,3-Dibromo-1-propanol

Base Information

• Chemical Name: 2,3-Dibromo-1-propanol
• CAS No.: 96-13-9
• Deprecated CAS: 116499-75-3,204570-16-1,204570-16-1
• Molecular Formula: C3H6Br2O
• Molecular Weight: 217.888
• Hs Code.: 29055900
• European Community (EC) Number: 202-480-9
• NSC Number: 6203
• UN Number: 2810
• UNII: C0YBW1OA2I
• DSSTox Substance ID: DTXSID7021817
• Nikkaji Number: J3.961F
• Wikidata: Q26840749
• NCI Thesaurus Code: C44303
• ChEMBL ID: CHEMBL1403428
• Mol file: 96-13-9.mol

Synonyms:2,3-dibromo-1-propanol;2,3-dibromopropanol

Chemical Property of 2,3-Dibromo-1-propanol

Chemical Property:

• Appearance/Colour: clear colorless liquid
• Vapor Pressure: 0.0675mmHg at 25°C
• Melting Point: 8oC
• Refractive Index: n20/D 1.559(lit.)
• Boiling Point: 203.3 °C at 760 mmHg
• PKA: 13.69±0.10(Predicted)
• Flash Point: 107 °C
• Density: 2.129 g/cm³
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Water Solubility.: 5-10 g/100 mL at 20 ºC
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 217.87649
• Heavy Atom Count: 6
• Complexity: 32
• Transport DOT Label: Poison

Purity/Quality:

99% ^*data from raw suppliers

2,3-Dibromo-1-propanol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 45-20/22-24-52/53-62
• Safety Statements: 53-45-61

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Halogenated Alcohols
• Canonical SMILES: C(C(CBr)Br)O
• General Description: 2,3-Dibromo-1-propanol is a mutagenic metabolite of tris(2,3-dibromopropyl) phosphate, known for its carcinogenic and nephrotoxic properties. 2,3-Dibromo-1-propanol exists as enantiomers, and its stereochemistry may influence its toxicological effects, particularly due to potential stereoselective interactions with cytochrome P-450 enzymes. It can be synthesized via diazotization of diastereomeric d-tartrate salts of 2,3-dibromopropylamine, though this process may yield minor amounts of the secondary alcohol isomer, 1,3-dibromo-2-propanol, which can be separated chromatographically. The optical isomers of 2,3-dibromo-1-propanol are of interest for studying stereoselective differences in mutagenicity.

Technology Process of 2,3-Dibromo-1-propanol

There total 26 articles about 2,3-Dibromo-1-propanol 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%

allyl alcohol (107-18-6) → 2,3-Dibromopropan-1-ol (96-13-9)

Guidance literature:

With cerium(III) nitrate hexahydrate; dihydrogen peroxide; lithium bromide; In water; at 65 - 70 ℃; for 10h; Reagent/catalyst; Concentration; Temperature; Time;

DOI:10.1007/s11172-012-0064-z

Reference yield: 89.0%

1,2-Epoxy-3-bromopropane (3132-64-7,82584-73-4) → 2,3-Dibromopropan-1-ol (96-13-9) + 1,3-dibromo-2-hydroxypropane (96-21-9)

Guidance literature:

1,2-Epoxy-3-bromopropane; In dichloromethane; at 20 ℃; for 0.25h;

With water; In dichloromethane; Further stages.;

DOI:10.1071/CH06408

Reference yield: 60.0%

allyl alcohol (107-18-6) → 2,3-Dibromopropan-1-ol (96-13-9) + acrylic acid (79-10-7)

Guidance literature:

With ammonium cerium (IV) nitrate; lithium bromide; In water; at 65 - 70 ℃; for 5h; Temperature;

DOI:10.1007/s11172-012-0064-z

upstream raw materials:

pyridinium hydrobromide perbromide

allyl alcohol

acetic acid-(2,4,6,N-tetrabromo-anilide)

allyl bromide

Downstream raw materials:

bis(2,3-dibromopropoxy)methane

butyric acid-(2,3-dibromo-propyl ester)

3-bromo-1,2-propanediol

(-)-2,3-Dibromo-1-propanol

Refernces

Preparation of (+)- and (-)-2,3-Dibromo-1-propanols

10.1021/je00030a033

The research focused on the preparation and purification of enantiomers of 2,3-dibromo-1-propanol, a mutagenic metabolite of the potent mutagen, carcinogen, and nephrotoxin tris(2,3-dibromopropyl) phosphate. The purpose of the study was to determine the influence of stereochemistry on the toxic properties of 2,3-dibromopropanols and their phosphate esters, as oxidations by cytochrome P-450 are often stereoselective. The researchers synthesized the optical isomers by diazotization of the diastereomeric d-tartrate salts of 2,3-dibromopropylamine, yielding products that contained approximately 13% of the secondary alcohol 1,3-dibromo-2-propanol. The primary and secondary alcohols were separated using column chromatography on silica gel or preparative GLC, and their structures were distinguished using NMR and mass spectrometry. The optical isomers were obtained and will be used to examine possible stereoselective differences in mutagenic potency. Chemicals used in the process included allylamine, d-tartaric acid, concentrated HBr, bromine, NaOH, NaNO2, H2SO4, and various solvents such as methanol, hexane, benzene, and ether for chromatography and extraction.