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 95% ^*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
• Uses: 2,3-Dibromo-1-propanol is a metabolite of the flame retardant tris(2,3-dibromopropyl) phosphate (T775560), previously shown to be a mutagen and carcinogen in experimental animals. The major use of 2,3-dibromo-1-propanol is as an intermediate in the production of flame retardants, insecticides, and pharmaceuticals, and the chemical itself has been used as a flame retardant. 2,3-Dibromo-1-propanol was used in the production of tris(2,3-dibromopropyl) phosphate, a flame retardant used in children’s clothing and other products (HSDB 2009). Tris(2,3-dibromopropyl) phosphate was banned from use in sleepwear in 1977 by the Consumer Product Safety Commission after studies showed that it causedcancer in experimental animals (NTP 1993, HSDB 2009). Synthetic building block, fire-proofing agent, and carcinogen.

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:

4-methyl-benzoic acid-(2,3-dibromo-propyl ester)

DL-α,β-distearin

2,3-dimethoxypropan-1-ol

N,N'-(2-hydroxy-propanediyl)-bis-phthalimide

Refernces

• 1、 Nokhbeh, Seyed Reza,Gholizadeh, Mostafa,Salimi, Alireza,Sparkes, Hazel A.. "Crystal structure, characterization, Hirshfeld surface analysis and DFT studies of two [propane 3-bromo-1-(triphenyl phosphonium)] cations containing bromide (I) and tribromide (II) anions: The anion (II) as a new brominating agent for unsaturated compounds". . p. 542 - 554. Retrieved 2019/06/18.
• 2、 Seidl, Frederick J.,Burns, Noah Z.. "Selective bromochlorination of a homoallylic alcohol for the total synthesis of (-)-Anverene". supporting information. p. 1361 - 1365. Retrieved 2016/08/02.