tribromoborane

• ChemBase ID: 107043
• Molecular Formular: BBr3
• Molecular Mass: 250.523
• Monoisotopic Mass: 247.7643164
• SMILES: BrB(Br)Br
• Canonical SMILES: BrB(Br)Br
• InChI: InChI=1S/BBr3/c2-1(3)4
• InChIKey: ILAHWRKJUDSMFH-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: tribromoborane
• IUPAC Traditional name: boron tribromide
• Synonyms: Tribromoborane; BORON BROMIDE; BORON TRIBROMIDE; Boron tribromide solution; Boron tribromide, 1M soln. in dichloromethane; Tribromoboron; Boron tribromide; 三溴化硼 溶液; 三溴化硼,1M在二氯甲烷溶剂中; 三溴化硼

Database IDs

• CAS Number: 10294-33-4
• EC Number: 233-657-9
• MDL Number: MFCD00011312
• Merck Index: 141347
• PubChem SID: 24852662; 162093474; 24866111; 24852661; 24853799; 24852048; 24865221
• PubChem CID: 25134
• Chemspider ID: 16787736
• Wikipedia Title: Boron_tribromide

CALCULATED PROPERTIES

• H Acceptors: 0
• H Donor: 0
• LogD (pH = 5.5): 2.3303
• LogD (pH = 7.4): 2.3303
• Log P: 2.3303
• Molar Refractivity: 26.2056 cm^3
• Polarizability: 12.004274 Å^3
• Polar Surface Area: 0.0 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: reacts violently in water
• Apperance: colorless; colorless to amber; colorless to amber liquid; Liquid; Liquid, ampouled under argon
• Melting Point: -46 °C(lit.); -46.3 °C; -46.3°C; -46°C
• Boiling Point: ~90 °C; ~90 °C(lit.); 90°C; 91.3 °C; 91.3°C
• Flash Point: -1 °C; 1.4 °F; -17 °C; -18 °C; 195.8 °F; 30.2 °F; 91 °C
• Density: 0.859 g/mL at 25 °C; 0.869 g/mL at 25 °C; 1.46 g/mL at 20 °C; 1.467; 1.467 g/mL at 25 °C; 2.60 g/mL at 20 °C(lit.); 2.643; 2.643 g/cm^3
• Refractive Index: 1.00207; 1.4340
• Vapor Pressure: 40 mmHg ( 14 °C); 7.2 kPa (20 °C)
• Vapor Density: 8.6 (vs air)
• Viscosity: 7.31 x 10^-4 Pa s (20 °C)
• Heat Capacity: 0.2706 J/K
• Std enthalpy of formation: -0.8207 kJ/g

Safety Information

• Storage Warning: Moisture Sensitive
• RTECS: ED7400000
• European Hazard Symbols: Corrosive (C); Corrosive (C); Flammable (F); Nature polluting (N); Highly toxic (T+); Very toxic (T+)
• UN Number: 2692; 3384; 3390; UN2692; UN3390
• German water hazard class: 3
• Hazard Class: 6.1; 8
• Packing Group: 1; I
• Risk Statements: 11-14-26/28-35-48/20-51/53-62-65; 11-14-26/28-35-50/53-65; 14-26/28-35; 14-26/28-35-40; R:12-26/28-35; R14, R26/28, R35
• Safety Statements: 26-28-36/37/39-45; 26-28-36/37/39-45-61-62; 9-26-28-36/37/39-45; S:9-26-28-45-36/37/39; S1/2, S9, S26, S28, S36/37/39, S45
• TSCA Listed: 是
• EU Index: 005-003-00-0
• GHS Pictograms: GHS02; GHS05; : Skin Corr. 1B; GHS06; : Acute Tox. 2; GHS07; GHS08; GHS09
• GHS Signal Word: DANGER; Danger
• NFPA704:
  

  0

  3

  2

  W
• GHS Hazard statements: 330, 300, 314; H225-H300-H304-H314-H330-H336-H410; H225-H304-H314-H336-H361f-H373-H411; H300-H314-H330; H300-H314-H330-H351; H300-H330-H314; H300-H330-H314-H318; H300-H330-H314-H318-H351; H314-H351
• GHS Precautionary statements: P210-P260-P264-P273-P280-P284; P210-P261-P273-P280-P301 + P310-P305 + P351 + P338; P260-P264-P280-P284-P301 + P310-P305 + P351 + P338; P260-P264-P280-P284-P305 + P351 + P338-P310; P260-P301+P310-P303+P361+P353-P304+P340-P305+P351+P338-P320-P330-P405-P501A; P280-P305 + P351 + P338-P310
• Personal Protective Equipment: Faceshields, full-face respirator (US), Gloves, Goggles, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 2692 8/PG 1; UN 3384 6.1/PG 1; UN 3390 6.1/PG 1
• Supplemental Hazard Statements: Reacts violently with water.

Product Information

• Purity: ≥99%; ≥99.0% (AT); ≥99.99%; 99% min; 99.5%; 99.9%; 99.999% (metals basis)
• Concentration: ~1 M in methylene chloride; 1.0 M in heptane; 1.0 M in hexanes; 1.0 M in methylene chloride; 1M soln. in dichloromethane
• Grade: purum; ReagentPlus®
• Empirical Formula (Hill Notation): BBr3

DETAILS

MP Biomedicals - 05202333

colorless to amber liquid

Sigma Aldrich - 211230

Packaging
100 mL in Sure/Seal™
Application
Reactant for preparation of:
• Drug intermediate 6-nitro-L-DOPA1
• Luminescent polystyrene derivatives with sterically protected carbazolylborane moieties2
• High-quality boron-doped graphene via Wurtz-type reductive coupling reaction3
• Mercapto-(+)-methamphetamine haptens for synthesis of (+)-methamphetamine conjugate vaccines with improved epitope densities4
• Micrometer-sized organic molecule-DNA hybrid structures5
• Borane complexes via electrophilic aromatic borylation reactions6
• A 5-HT2C receptor agonist7
• Biphenyl-derivatives possessing tertiary amino groups as β-secretase(BACE1) inhibitors for the treatment of Alzheimer′s disease8
• A highly near-IR region fluorescent p-extended boron aza-dipyrromethene moiety unit9
• Tetrahydroisoquinoline derivatives via intramolecular cyclization of methoxy-substituted N-phenethylimides10

Sigma Aldrich - 230367

Packaging
5, 25, 100 g in ampule
Application
Reactant for preparation of:
• Drug intermediate 6-nitro-L-DOPA1
• Luminescent polystyrene derivatives with sterically protected carbazolylborane moieties2
• High-quality boron-doped graphene via Wurtz-type reductive coupling reaction3
• Mercapto-(+)-methamphetamine haptens for synthesis of (+)-methamphetamine conjugate vaccines with improved epitope densities4
• Micrometer-sized organic molecule-DNA hybrid structures5
• Borane complexes via electrophilic aromatic borylation reactions6
• A 5-HT2C receptor agonist7
• Biphenyl-derivatives possessing tertiary amino groups as β-secretase(BACE1) inhibitors for the treatment of Alzheimer′s disease8
• A highly near-IR region fluorescent p-extended boron aza-dipyrromethene moiety unit9
• Tetrahydroisoquinoline derivatives via intramolecular cyclization of methoxy-substituted N-phenethylimides10
With alkynes forms 2-alkenyldibromoboranes, which show reversed regiochemistry in Diels-Alder reactions as compared to BBN. Intermediates generated from 1-alkynes couple to alkyl halides providing trisubstituted alkenes. Reacts with chiral sulfonamides to provide precursors of chiral glycidol esters, acetate diols, β-hydroxy esters, and amino acid esters. Useful for the synthesis of precursors to group 13-15 semiconductor materials.

Sigma Aldrich - 202207

Application
Used to cleave aryl methyl ethers in a syntheses of a benzopyranobenzopyran from a coumarin scaffold11 and ladder-type conjugated polymers.12
Reactant for preparation of:
• Drug intermediate 6-nitro-L-DOPA1
• Luminescent polystyrene derivatives with sterically protected carbazolylborane moieties2
• High-quality boron-doped graphene via Wurtz-type reductive coupling reaction3
• Mercapto-(+)-methamphetamine haptens for synthesis of (+)-methamphetamine conjugate vaccines with improved epitope densities4
• Micrometer-sized organic molecule-DNA hybrid structures5
• Borane complexes via electrophilic aromatic borylation reactions6
• A 5-HT2C receptor agonist7
• Biphenyl-derivatives possessing tertiary amino groups as β-secretase(BACE1) inhibitors for the treatment of Alzheimer′s disease8
• A highly near-IR region fluorescent p-extended boron aza-dipyrromethene moiety unit9
• Tetrahydroisoquinoline derivatives via intramolecular cyclization of methoxy-substituted N-phenethylimides10
Packaging
100, 250 g in Sure/Seal™
2 kg in Sure/Seal™
25 g in ampule
Legal Information
ReagentPlus is a registered trademark of Sigma-Aldrich Co. LLC

Sigma Aldrich - 211222

Application
Used to cleave aryl methyl ethers in a synthesis of a benzopyranobenzopyran from a coumarin scaffold.11
Reactant for preparation of:
• Drug intermediate 6-nitro-L-DOPA1
• Luminescent polystyrene derivatives with sterically protected carbazolylborane moieties2
• High-quality boron-doped graphene via Wurtz-type reductive coupling reaction3
• Mercapto-(+)-methamphetamine haptens for synthesis of (+)-methamphetamine conjugate vaccines with improved epitope densities4
• Micrometer-sized organic molecule-DNA hybrid structures5
• Borane complexes via electrophilic aromatic borylation reactions6
• A 5-HT2C receptor agonist7
• Biphenyl-derivatives possessing tertiary amino groups as β-secretase(BACE1) inhibitors for the treatment of Alzheimer′s disease8
• A highly near-IR region fluorescent p-extended boron aza-dipyrromethene moiety unit9
• Tetrahydroisoquinoline derivatives via intramolecular cyclization of methoxy-substituted N-phenethylimides10
Packaging
10 mL in glass bottle
2 L in Sure/Seal™
2.5 L in glass bottle
4×25, 100, 800 mL in Sure/Seal™

Sigma Aldrich - 403857

Packaging
100 mL in Sure/Seal™
Application
Reactant for preparation of:
• Drug intermediate 6-nitro-L-DOPA1
• Luminescent polystyrene derivatives with sterically protected carbazolylborane moieties2
• High-quality boron-doped graphene via Wurtz-type reductive coupling reaction3
• Mercapto-(+)-methamphetamine haptens for synthesis of (+)-methamphetamine conjugate vaccines with improved epitope densities4
• Micrometer-sized organic molecule-DNA hybrid structures5
• Borane complexes via electrophilic aromatic borylation reactions6
• A 5-HT2C receptor agonist7
• Biphenyl-derivatives possessing tertiary amino groups as β-secretase(BACE1) inhibitors for the treatment of Alzheimer′s disease8
• A highly near-IR region fluorescent p-extended boron aza-dipyrromethene moiety unit9
• Tetrahydroisoquinoline derivatives via intramolecular cyclization of methoxy-substituted N-phenethylimides10

Sigma Aldrich - 419508

Application
Used to cleave aryl methyl ethers in a synthesis of a benzopyranobenzopyran from a coumarin scaffold.11
Reactant for preparation of:
• Drug intermediate 6-nitro-L-DOPA1
• Luminescent polystyrene derivatives with sterically protected carbazolylborane moieties2
• High-quality boron-doped graphene via Wurtz-type reductive coupling reaction3
• Mercapto-(+)-methamphetamine haptens for synthesis of (+)-methamphetamine conjugate vaccines with improved epitope densities4
• Micrometer-sized organic molecule-DNA hybrid structures5
• Borane complexes via electrophilic aromatic borylation reactions6
• A 5-HT2C receptor agonist7
• Biphenyl-derivatives possessing tertiary amino groups as β-secretase(BACE1) inhibitors for the treatment of Alzheimer′s disease8
• A highly near-IR region fluorescent p-extended boron aza-dipyrromethene moiety unit9
• Tetrahydroisoquinoline derivatives via intramolecular cyclization of methoxy-substituted N-phenethylimides10
Packaging
4×25, 100, 500 g in Sure/Seal™
Legal Information
ReagentPlus is a registered trademark of Sigma-Aldrich Co. LLC

Sigma Aldrich - 15692

Application
Reactant for preparation of:
• Drug intermediate 6-nitro-L-DOPA1
• Luminescent polystyrene derivatives with sterically protected carbazolylborane moieties2
• High-quality boron-doped graphene via Wurtz-type reductive coupling reaction3
• Mercapto-(+)-methamphetamine haptens for synthesis of (+)-methamphetamine conjugate vaccines with improved epitope densities4
• Micrometer-sized organic molecule-DNA hybrid structures5
• Borane complexes via electrophilic aromatic borylation reactions6
• A 5-HT2C receptor agonist7
• Biphenyl-derivatives possessing tertiary amino groups as β-secretase(BACE1) inhibitors for the treatment of Alzheimer′s disease8
• A highly near-IR region fluorescent p-extended boron aza-dipyrromethene moiety unit9
• Tetrahydroisoquinoline derivatives via intramolecular cyclization of methoxy-substituted N-phenethylimides10

Sigma Aldrich - 15690

Application
Reactant for preparation of:
• Drug intermediate 6-nitro-L-DOPA1
• Luminescent polystyrene derivatives with sterically protected carbazolylborane moieties2
• High-quality boron-doped graphene via Wurtz-type reductive coupling reaction3
• Mercapto-(+)-methamphetamine haptens for synthesis of (+)-methamphetamine conjugate vaccines with improved epitope densities4
• Micrometer-sized organic molecule-DNA hybrid structures5
• Borane complexes via electrophilic aromatic borylation reactions6
• A 5-HT2C receptor agonist7
• Biphenyl-derivatives possessing tertiary amino groups as β-secretase(BACE1) inhibitors for the treatment of Alzheimer′s disease8
• A highly near-IR region fluorescent p-extended boron aza-dipyrromethene moiety unit9
• Tetrahydroisoquinoline derivatives via intramolecular cyclization of methoxy-substituted N-phenethylimides10

REFERENCES

• Reagent for cleavage of ethers: Synthesis, 249 (1983). Converts alcohols to alkyl bromides under mild conditions: Tetrahedron Lett., 35, 1051 (1994). Cleavage of N-methoxymethyl: Tetrahedron Lett., 42, 8633 (2001), or N-benzyl: Tetrahedron Lett., 45, 4093 (2004) protecting groups can also be achieved under mild conditions. Alkynes undergo bromoboration; the products can be transformed, e.g. to trisubstituted alkenes: Tetrahedron Lett., 29, 1811 (1988), or enyne-allenes: Tetrahedron Lett., 35, 1829 (1994).
• Reagent for cleavage of ethers. For a brief feature of uses of the reagent in organic synthesis, see: Synlett, 1636 (2005). See also preceding entry.