tributylphosphane

• ChemBase ID: 104726
• Molecular Formular: C12H27P
• Molecular Mass: 202.316541
• Monoisotopic Mass: 202.18503749
• SMILES: CCCCP(CCCC)CCCC
• Canonical SMILES: CCCCP(CCCC)CCCC
• InChI: InChI=1S/C12H27P/c1-4-7-10-13(11-8-5-2)12-9-6-3/h4-12H2,1-3H3
• InChIKey: TUQOTMZNTHZOKS-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: tributylphosphane
• IUPAC Traditional name: tributylphosphine
• Synonyms: Cytop® 340; Tributylphosphine solution; NSC 91700; P(n-Bu)3; TBP; Tri-n-butylphosphine; Tributylphosphine; Tributylphosphine; Tributylphosphane; TRI-n-BUTYLPHOSPHINE; Tris(trimethylsilyl)phosphane; Tributylphosphine; 三丁基膦 溶液; 三丁基膦; 三正丁基膦; 三丁基膦

Database IDs

• CAS Number: 998-40-3
• EC Number: 213-651-2
• MDL Number: MFCD00009462
• Beilstein Number: 1738261
• PubChem SID: 24889415; 24900248; 162092272; 24900459
• PubChem CID: 13831
• Wikipedia Title: Tributylphosphine

CALCULATED PROPERTIES

• H Acceptors: 0
• H Donor: 0
• LogD (pH = 5.5): 3.8171377
• LogD (pH = 7.4): 3.8240328
• Log P: 4.3595
• Molar Refractivity: 68.4258 cm^3
• Polarizability: 25.590317 Å^3
• Polar Surface Area: 0.0 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Insoluble in water. Miscible with ether, methanol, ethanol and benzene; negligible in water; organic solvents such as heptane
• Apperance: Colorless oily liquid; liquid; Liquid
• Melting Point: -60.15°C (213K); -65°C
• Boiling Point: 150 °C/50 mmHg(lit.); 150°C; 239.85°C (513K); 240°C
• Flash Point: >93°C(199°F); 117 °C; 186.8 °F; 37 °C; 37.2°C; 86 °C; 98.6 °F
• Auto Ignition Point: 168 °C; 200°C; 392 °F
• Density: 0.81 g/ml; 0.81 g/mL at 25 °C(lit.); 0.82 g/ml; 0.820
• Refractive Index: 1.4620; n20/D 1.462(lit.); n20/D 1.463
• Vapor Density: 9 (vs air)
• Dipole Moment: ?
• Ligand For: Acetylations; Addition Reactions; Stille Coupling

Safety Information

• Storage Condition: 2-8°C, Desiccate, Store Under Nitrogen
• Storage Warning: Air & Moisture Sensitive
• RTECS: SZ3270000
• European Hazard Symbols: Corrosive (C); Flammable (F); Nature polluting (N); Toxic (T); X; Harmful (Xn)
• UN Number: 3254; UN3254
• German water hazard class: 3
• Hazard Class: 4.2
• Packing Group: 1; I; Truck Only (Not for Export)
• Risk Statements: 17-21/22-34; 17-22-34-51/53; 61-36/37/38; R:22-27; R11 R17 R20/21/22 R34 R38
• Safety Statements: 17-26-36/37/39-43-45; 53-26-45; 7-17-26-36/37/39-45; S:36/37/39
• EU Classification: S1
• EU Hazard Identification Number: 4.2
• Emergency Response Guidebook(ERG) Number: 135
• TSCA Listed: 是
• GHS Pictograms: GHS02; GHS05; GHS06; GHS07; GHS08; GHS09
• GHS Signal Word: Danger
• Main Hazard: Stench, Flammable, Corrosive
• NFPA704:
  

  3

  1

  2
• GHS Hazard statements: H226-H250-H302-H312-H314; H250-H252-H301-H314-H318-H411-H401; H314-H335-H360D
• GHS Precautionary statements: P201-P261-P280-P305 + P351 + P338-P310; P210-P301+P310-P303+P361+P353-P305+P351+P338-P405-P422A-P501A; P222-P231-P280-P305 + P351 + P338-P310-P422
• Personal Protective Equipment: Faceshields, full-face respirator (US), Gloves, Goggles, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 3254 4.2/PG 1

Product Information

• Purity: ~85%; ≥90%; ≥93.5% (Tri-N-butylphosphine, GC); ≥97% (Tri-N-butylphospine + isomers); 94%; 95%; 97%; 99%
• Concentration: 200 mM (in N-methyl-2-pyrrolidinone)
• Grade: technical
• Impurities: <1% TBP oxide; 5% TBP isomers
• Linear Formula: [CH3(CH2)3]3P
• Empirical Formula (Hill Notation): C12H27P

DETAILS

MP Biomedicals - 02156971

1 ml = approx. 0.81 g
NOT FOR EXPORT

Sigma Aldrich - T7567

Application
TBP is an uncharged reducing agent for disulfide bonds of cysteine residues. This reagent is ideally suited for preparation of protein samples prior to IEF and 2D electrophoresis. Reduction with TBP and subsequent alkylation with iodoacetamide improves resolution, allows greater sample loads, and therefore, improves visualization of low abundance proteins
Packaging
Sealed ampule of 0.5 mL

Sigma Aldrich - 90827

Application
1,4-addition catalyst; used with disulfides for the thioetherification of alcohols; acylation catalyst; used to prepare active esters.
Other Notes
This reactive phosphine allowed the formation of a strained lactone where triphenylphosphine failed 1,2
Packaging
25, 100, 500 mL in Sure/Seal™

Sigma Aldrich - T49484

Application
1,4-addition catalyst; used with disulfides for the thioetherification of alcohols; acylation catalyst; used to prepare active esters.
Packaging
25 mL in Sure/Seal™
5 mL in glass bottle

Sigma Aldrich - 731374

Packaging
25, 100 g in Sure/Seal™
Application
Catalyst for:
• Domino reactions of activated conjugated dienes with β,γ-unsaturated-α-ketoesters1
• [3+2]-Cycloadditions2
• Umpolung addition reactions3
• Reductive carbonylation4
• Allylation reactions5

Sigma Aldrich - 247049

Application
1,4-addition catalyst; used with disulfides for the thioetherification of alcohols; acylation catalyst; used to prepare active esters.
Used with platinum (II) or (IV) in an intermolecular hydroamination of unactivated alkenes.
Packaging
100, 500 g in Sure/Seal™

Sigma Aldrich - 42238

Legal Information
Cytop is a registered trademark of Cytec Technology Corp.

REFERENCES

• A useful alternative to Triphenylphosphine, L02502 in many applications. Advantages include its greater reactivity and the water-solubility of the by-product phosphine oxide, simplifying its removal.
• In combination with phenyl isocyanate and a Pd catalyst, converts cinnamyl alcohol directly to a phosphorane, which reacts with aldehydes to give conjugated dienes: Chem. Lett., 1449 (1988):
  
• Can behave as a hypernucleophilic catalyst in acylation reactions, with similar results to 4-(Dimethylamino)pyridine, A13016: J. Am. Chem. Soc., 115, 3358 (1993).
• Effective catalyst for the Baylis-Hillman reaction with less tendency than the usual DABCO (1,4-Diazabicyclo[2.2.2]octane, A14003) to promote aldol type side reactions: J. Org. Chem., 62, 1521 (1997).
• For example of its use in Mitsunobu-type reactions, see Diisopropyl azodicarboxylate, L10386.