Tetrabutylphosphonium bromide (HCID 76564)

Overview

RN given refers to Br

Names & identifiers

Preferred name: Tetrabutylphosphonium bromide
IUPAC: tetrabutylphosphanium bromide
English name: Tetrabutylphosphonium bromide
Molecular formula: C16H36BrP
Molecular weight: 339.33

Names & synonyms

Tetrabutylphosphonium bromide3115-68-2Tetra-N-butylphosphonium bromidePhosphonium, tetrabutyl-, bromideDTXSID6047945NSC-419422953275L2KDTXCID6027921Bu4PBrDTXSID0045042TBP BrRefChem:188422

Show more names

px4bP4,4,4,4BrHISHICOLIN PX-4B1-(3-methoxypropoxy)butaneTributylphosphoniuM broMideTetrabutylphosphoniuM broMidtetrabutyl-phosphoniubromideBromo(tetrabutyl)phosphorane

DTXCID8025042221-487-8Tetrabutylphosphoniumtetrabutylphosphanium;bromideMFCD00011853tetrabutylphosphanium bromidePX 4BEINECS 221-487-8

Database identifiers

CAS: 3115-68-2
PubChem CID: 76564
DTXSID: DTXSID6047945
ChEMBL: CHEMBL3185844
UNII: 2953275L2K
EC Number: 221-487-8

Properties

Computed structural properties

Topological polar surface area: 0 Å²
Hydrogen bond donors: 0
Hydrogen bond acceptors: 1
Rotatable bonds: 12
Heavy atoms: 18
Formal charge: 0
Complexity: 116

Experimental & physicochemical properties

Physical DescriptionLiquid

Physicochemical properties

Melting point: 100 · 100-103 °C(lit.)
Density: 1.8 · 1.8[at 20℃]
vapor pressure: 0.018 Pa · 0.018Pa at 25℃
Flash point: 290 °C · 290 °C
storage temp.: 2 · under inert gas (nitrogen or Argon) at 2-8°C
solubility: Chloroform (Slightly), Methanol (Slightly)
form: crystal
color: white
Water Solubility: 70 g/100 · ca 70 g/100 mL
Sensitive: Hygroscopic, Light Sensitive
BRN: 4160474 · 4160474
Stability: hygroscopic
InChI: 1S/C16H36P.BrH/c1-5-9-13-17(14-10-6-2,15-11-7-3)16-12-8-4;/h5-16H2,1-4H3;1H/q+1;/p-1
InChIKey: JRMUNVKIHCOMHV-UHFFFAOYSA-M
SMILES: [Br-].CCCC[P+](CCCC)(CCCC)CCCC
LogP: -0.44 at · -0.44 at 23℃
CAS DataBase Reference: 3115 · 3115-68-2(CAS DataBase Reference)
EWG's Food Scores: 1 · 1
FDA UNII: 2953275 L2K · 2953275L2K
NIST Chemistry Reference: Phosphonium bromide, tetrabutyl(3115-68-2)
EPA Substance Registry System: Phosphonium, tetrabutyl-, bromide (3115-68-2)
UNSPSC Code: 12352001 · 12352001
NACRES: 22 · NA.22
Symbol(GHS): 5 · GHS05,GHS06,GHS08,GHS09
Signal word: Danger
Hazard statements: 290 · H290-H302-H311-H317-H318-H361fd-H411
Precautionary statements: 273 · P273-P280-P301+P312-P302+P352+P312-P305+P351+P338-P308+P313
PPE: 95 · dust mask type N95 (US), Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges
Hazard Codes: Xn,T,Xi
Risk Statements: 21 · 21/22-36/37/38-24-20/21/22
Safety Statements: 26 · 26-37/39-45-36/37/39-28A-36
RIDADR: 3464 · UN 3464 6.1/PG 3
WGK Germany: 3 · 3
RTECS: 2417000 · TA2417000
TSCA: TSCA listed
HazardClass: 6.1 · 6.1
PackingGroup: II
HS Code: 29310095 · 29310095
Storage Class: 6.1 C · 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
Hazard Classifications: 3 DermalAcute · Acute Tox. 3 DermalAcute Tox. 4 OralAquatic Chronic 2Eye Dam. 1Met. Corr. 1Repr. 2Skin Sens. 1B
Toxicity: 50 · mouse,LD50,intravenous,56mg/kg (56mg/kg),U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. Vol. NX#03131,
REACH Registrations: Active

Safety & regulation

GHS classification

GHS Classification · 6 items

Danger

H302 (99.4%): Harmful if swallowed [Warning Acute toxicity, oral]

P203, P261, P262, P264, P264+P265, P270, P271, P272, P273, P280, P301+P317, P302+P352, P304+P340, P305+P354+P338, P316, P317, P318, P319, P321, P330, P332+P317, P333+P317, P361+P364, P362+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 163 reports by companies from 14 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Warning

H317: May cause an allergic skin reaction [Warning Sensitization, Skin]

Hazard information

Regulatory Information · 3 items

Phosphonium, tetrabutyl-, bromide (1:1) is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Phosphonium, tetrabutyl-, bromide (1:1) are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Status: Active Update: 06-05-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/18995

Tetrabutylphosphonium: Does not have an individual approval but may be used under an appropriate group standard

Hazard Classes and Categories · 3 items

Acute Tox. 4 (99.4%)

Skin corrosion/irritation - Category 2

Skin sensitization - Category 1B

Safety data

PPE: dust mask type N95 (US), Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges
wgk: 3
tsca: TSCA listed
rtecs: TA2417000
ridadr: UN 3464 6.1/PG 3
hs_code: 29310095
Toxicity: mouse,LD50,intravenous,56mg/kg (56mg/kg),U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. Vol. NX#03131,
risk_code: 21/22-36/37/38-24-20/21/22
Signal word: Danger
Symbol(GHS): GHS05,GHS06,GHS08,GHS09
hazard_code: Xn,T,Xi
safety_code: 26-37/39-45-36/37/39-28A-36
hazard_class: 6.1
Storage Class: 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
packing_group: II
Hazard statements: H290-H302-H311-H317-H318-H361fd-H411
REACH Registrations: Active
Hazard Classifications: Acute Tox. 3 DermalAcute Tox. 4 OralAquatic Chronic 2Eye Dam. 1Met. Corr. 1Repr. 2Skin Sens. 1B
Precautionary statements: P273-P280-P301+P312-P302+P352+P312-P305+P351+P338-P308+P313

Chemistry & industry

Uses & manufacturing

U.S. Production2023: 50,000 - <250,000 lb

Industry UsesProcessing aids not otherwise specified

General Manufacturing Information · 2 items

Synthetic Rubber Manufacturing

Phosphonium, tetrabutyl-, bromide (1:1): ACTIVE

Applications · 3 items

UsesTetrabutylphosphonium bromide is a useful synthetic reagent used in proteomics research.

UsesTetra-n-butylphosphonium bromide is used as a phase-transfer catalyst at high temperatures, at which nitrogen analogues tend to undergo elimination e.g. as catalyst for the dealkoxycarbonylation of malonates and -keto esters by heating in stearic acid. used as an ionic liquid solvent in the regioselective O-alkylation of C/O ambident nucleophiles. It is a synthetic reagent used in proteomics research.

UsesTetrabutylphosphonium bromide (TBPB) is a quaternary salt which can be used:As a medium to disperse ruthenium catalyst for the synthesis of ethylene glycol from synthesis gas via ruthenium melt catalysis.As a catalyst supported on silica or alumina for the halogen exchange reaction to synthesize alkyl bromide from alkyl chloride.To synthesize various ionic liquids on mixing with different proportions of 1,3-dimethylurea for capturing NO gas.As a hydrogen-bond acceptor along with levulinic acid as a hydrogen-bond donor for the preparation of deep eutectic solvents to separate toluene from toluene/n-hexane mixtures.To prepare ionic semiclathrate hydrates.