Basic information
- Standard SMILES
CCB(CC)CC- InChIKey
LALRXNPLTWZJIJ-UHFFFAOYSA-N- Molecular formula
- C6H15B
- Average molar mass
- 98 g/mol
- Monoisotopic mass
- 98.12668088
Overview
used in the radical deuteration reaction of ribonucleoside derivatives
Names & identifiers
- Preferred name
- Triethylborane
- IUPAC
- triethylborane
- English name
- Triethylborane
- Molecular formula
- C6H15B
- Molecular weight
- 97.99
Names & synonyms
Show more names
Database identifiers
- CAS
97-94-9- PubChem CID
- 7357
- DTXSID
DTXSID2052653- UNII
- Z3S980Z4P3
- EC Number
- 202-620-9
- Nikkaji
- J55.478B
Properties
Computed structural properties
- Topological polar surface area
- 0 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 0
- Rotatable bonds
- 3
- Heavy atoms
- 7
- Formal charge
- 0
- Complexity
- 25.7
Experimental & physicochemical properties
Color/Form
Colorless liquid
Colorless fuming liquid
Solubility
Soluble in alcohol, ether
Miscible with most organic solvents; immiscible with water
Vapor Pressure
53.0 [mmHg]
53 mm Hg at 25 °C /est/
Physicochemical properties
- Melting point
- -92 °C · -92°C
- Boiling point
- 95 °C · 95°C
- Density
- 0.865 g/mL · 0.865 g/mL at 25 °C
- vapor pressure
- 67 hPa · 67hPa at 25℃
- refractive index
- 20 · n20/D 1.380
- Flash point
- 1 °F · 1 °F
- storage temp.
- 0 · 0-6°C
- form
- Liquid
- color
- Colorless to light amber
- Water Solubility
- Decomposes
- Specific Heat Capacity
- 2.46 J/ · Cp(liquid): 2.46 J/(g·K), at 25℃
- Sensitive
- Air Sensitive
- Merck
- 14 · 14,9668
- BRN
- 1731462 · 1731462
- InChI
- 1S/C6H15B/c1-4-7(5-2)6-3/h4-6H2,1-3H3
- InChIKey
- LALRXNPLTWZJIJ-UHFFFAOYSA-N
- SMILES
- CCB(CC)CC
- CAS DataBase Reference
- 97 · 97-94-9(CAS DataBase Reference)
- FDA UNII
- 3 S980Z4P3 · Z3S980Z4P3
- NIST Chemistry Reference
- Borane, triethyl-(97-94-9)
- EPA Substance Registry System
- Borane, triethyl- (97-94-9)
- UNSPSC Code
- 12352001 · 12352001
- NACRES
- 22 · NA.22
- Symbol(GHS)
- 2 · GHS02,GHS05,GHS07,GHS08
- Signal word
- Danger
- Hazard statements
- 302 · H302-H333-H314-H371-H372-H351-H335-H225
- Precautionary statements
- 501 · P501-P260-P270-P202-P240-P210-P233-P201-P243-P241-P242-P271-P264-P280-P370+P378-P308+P311-P303+P361+P353-P301+P330+P331-P363-P301+P312+P330-P304+P340+P310-P305+P351+P338+P310-P403+P233-P403+P235-P405
- target organs
- Central nervous system, Nervous system
- Hazard Codes
- F+,C,N,F
- Risk Statements
- 12 · 12-17-19-22-34-66-67-65-62-51/53-48/20-11-40-37
- Safety Statements
- 7 · 7-9-16-23-26-29-33-36/37/39-43-45-61-43A-62
- RIDADR
- 3399 · UN 3399 4.3/PG 2
- WGK Germany
- 2 · 2
- RTECS
- 2100000 · ED2100000
- F
- 2 · 2-10
- TSCA
- TSCA listed
- HazardClass
- 3 · 3
- PackingGroup
- II
- HS Code
- 29319090 · 29319090
- Storage Class
- 4.3 · 4.3 - Hazardous materials which set free flammable gases upon contact with water
- Hazard Classifications
- 2 Asp · Aquatic Chronic 2Asp. Tox. 1Eye Dam. 1Flam. Liq. 2Repr. 2Skin Corr. 1ASTOT RE 1 InhalationSTOT SE 3
- Hazardous Substances Data
- 97 · 97-94-9(Hazardous Substances Data)
- Toxicity
- 50 orl-rat: · LD50 orl-rat: 235 mg/kg 14KTAK -,693,64
- REACH Registrations
- Active
- Excepted Quantities
- Max Inner Pack (30g or 30ml) and Max Outer Pack (500g or 500ml)
Safety & regulation
GHS classification
GHS Classification
Danger
H225 (16.4%): Highly Flammable liquid and vapor [Danger Flammable liquids]
P203, P210, P222, P231, P233, P240, P241, P242, P243, P260, P264, P264+P265, P270, P271, P280, P284, P301+P316, P301+P330+P331, P302+P335+P334, P302+P361+P354, P303+P361+P353, P304+P340, P305+P354+P338, P316, P317, P318, P320, P321, P330, P363, P370+P378, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 256 reports by companies from 10 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Danger
H225: Highly Flammable liquid and vapor [Danger Flammable liquids]
Hazard information
Regulatory Information
Chemical: Borane, triethyl-
Status: Active Update: 19-08-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/19345
Borane, triethyl-: HSNO Approval: HSR001432 Approved with controls
Hazards Summary
Highly irritating; Animals exposed to high inhalation dose have lung irritation and convulsions; Oral LD50 (rat) = 235 mg/kg; . . . would decompose before occupational exposure can occur. [HSDB] Spontaneously flammable; [Merck Index] Corrosive to skin and eyes; [eChemPortal: ERMA] The trialkylborons are not soluble nor reactive in water; Toxic to rats at nonpyrophoric concentrations; [Ullmann] Pyrophoric; A corrosive substance that can cause injury to the skin, eyes, and respiratory tract; [MSDSonline] See Tri-n-butylborane.
RCRA Requirements
[40 CFR 261.32; U.S. National Archives and Records Administration's Electronic Code of Federal Regulations. Available from: http://www.gpoaccess.gov/ecfr as of December 15, 2004)] D003; A solid waste containing triethylboron may become characterized as a hazardous waste when subjected to testing for reactivity as stipulated in 40 CFR 261.23, and if so characterized, must be managed as a hazardous waste.
NFPA Hazard Classification
1 - Materials that, under emergency conditions, can cause significant irritation.
3 - Liquids and solids that can be ignited under almost all ambient temperature conditions. Materials produce hazardous atmospheres with air under almost all ambient temperatures or, though unaffected by ambient temperatures, are readily ignited under almost all conditions.
2 - Materials that readily undergo violent chemical changes at elevated temperatures and pressures.
W - No water: Materials that react violently or explosively with water.
Hazard Classes and Categories
Flam. Liq. 2 (16.4%)
Flammable liquids - Category 2
State Drinking Water Guidelines
(CA) CALIFORNIA 1000 ug/L /Boron/
(NH) NEW HAMPSHIRE 630 ug/L /Boron/
(ME) MAINE 1,400 ug/L /Boron/
(MN) MINNESOTA 1,000 ug/L /Boron/
(WI) WISCONSIN 960 ug/L /Boron/
Shipping Name/ Number DOT/UN/NA/IMO
[40 CFR 261.32; U.S. National Archives and Records Administration's Electronic Code of Federal Regulations. Available from: http://www.gpoaccess.gov/ecfr as of December 15, 2004)] D003; A solid waste containing triethylboron may become characterized as a hazardous waste when subjected to testing for reactivity as stipulated in 40 CFR 261.23, and if so characterized, must be managed as a hazardous waste.
Skin, Eye, and Respiratory Irritations
... Strong irritant
... May produce irritation of the nasal mucous membranes, the respiratory tract, and eyes. /Boron compounds/
Safety & protection
Disposal Methods
SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.
Preventive Measures
SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.
All equipment should be fully enclosed and carefully designed to eliminate any likelihood of autoignition. All equipment must be purged before opening. All possible sources of ignition should be eliminated and processes in which boron hydrides are heated must be minutely controlled. Automatic leak detectors with visual and acoustic warning signals should be fitted. Where possible, processes should be automated or operated by remote control. /Boron hydrides/
All containers should be thoroughly flushed before maintenance work is carried out on them and, in event of leakage, only persons with adequate personal protective equipment should be allowed in vicinity of containers. /Boranes/
Other Standards Regulations and Guidelines
Limit for livestock is 5 ug/ml boron in water. /Boron/
0.5 mg/l maximum (USSR) /Boron in drinking water/
Toxicology
Environmental Fate
TERRESTRIAL FATE: Triethylboron is spontaneously flammable in air and reacts with water(1). Triethylboron should have a very short existence in the environment(SRC).
AQUATIC FATE: Triethylboron is spontaneously flammable in air and reacts with water(1). Triethylboron should have a very short existence in the environment(SRC).
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), triethylboron, which has an estimated vapor pressure of 53 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely as a vapor in the ambient atmosphere. Triethylboron is spontaneously flammable in air and reacts with water(3). Triethylboron should have a very short existence in the environment(SRC).
Artificial Pollution Sources
Triethylboron's production and use as an igniter or fuel for jet and rocket engines, fuel additive, olefin polymerization catalyst, and as a chemical intermediate(1) may result in its release to the environment through various waste streams(SRC).
Probable Routes of Human Exposure
Occupational exposure to triethylboron may occur through inhalation and dermal contact with this compound at workplaces where triethylboron is produced or used. When used commercially, triethylboron would need to be handled in an inert atmosphere. The high reactivity, rapid decomposition, and commercial handling techniques suggest that triethylboron would decompose before occupational exposure can occur, should small amounts be released. Exposure to the general population is not be expected because of the spontaneous decomposition of triethylboron on contact with oxygen or moisture. (SRC)
Environmental Fate/Exposure Summary
Triethylboron's production and use as an igniter or fuel for jet and rocket engines, fuel additive, olefin polymerization catalyst, and as a chemical intermediate may result in its release to the environment through various waste streams. If released to air, an estimated vapor pressure of 53 mm Hg at 25 °C indicates triethylboron will exist solely as a vapor in the ambient atmosphere. Triethylboron is spontaneously flammable in air and reacts with water. These rapid reactions should dominate over all other environmental fate processes, and triethylboron should have a very short existence in the environment. Occupational exposure to triethylboron may occur through inhalation and dermal contact with this compound at workplaces where triethylboron is produced or used. When used commercially, triethylboron would need to be handled in an inert atmosphere. The high reactivity, rapid decomposition, and commercial handling techniques suggest that triethylboron would decompose before occupational exposure can occur, should small amounts be released. Exposure to the general population is not be expected because of the spontaneous decomposition of triethylboron on contact with oxygen or moisture. (SRC)
Regulatory information
RCRA Requirements
[40 CFR 261.32; U.S. National Archives and Records Administration's Electronic Code of Federal Regulations. Available from: http://www.gpoaccess.gov/ecfr as of December 15, 2004)] D003; A solid waste containing triethylboron may become characterized as a hazardous waste when subjected to testing for reactivity as stipulated in 40 CFR 261.23, and if so characterized, must be managed as a hazardous waste.
State Drinking Water Guidelines
(CA) CALIFORNIA 1000 ug/L /Boron/
(NH) NEW HAMPSHIRE 630 ug/L /Boron/
(ME) MAINE 1,400 ug/L /Boron/
(MN) MINNESOTA 1,000 ug/L /Boron/
(WI) WISCONSIN 960 ug/L /Boron/
Safety data
- F
- 2-10
- wgk
- 2
- tsca
- TSCA listed
- rtecs
- ED2100000
- ridadr
- UN 3399 4.3/PG 2
- hs_code
- 29319090
- Toxicity
- LD50 orl-rat: 235 mg/kg 14KTAK -,693,64
- risk_code
- 12-17-19-22-34-66-67-65-62-51/53-48/20-11-40-37
- Signal word
- Danger
- Symbol(GHS)
- GHS02,GHS05,GHS07,GHS08
- hazard_code
- F+,C,N,F
- safety_code
- 7-9-16-23-26-29-33-36/37/39-43-45-61-43A-62
- hazard_class
- 3
- Storage Class
- 4.3 - Hazardous materials which set free flammable gases upon contact with water
- packing_group
- II
- target organs
- Central nervous system, Nervous system
- Hazard statements
- H302-H333-H314-H371-H372-H351-H335-H225
- Excepted Quantities
- Max Inner Pack (30g or 30ml) and Max Outer Pack (500g or 500ml)
- REACH Registrations
- Active
- Hazard Classifications
- Aquatic Chronic 2Asp. Tox. 1Eye Dam. 1Flam. Liq. 2Repr. 2Skin Corr. 1ASTOT RE 1 InhalationSTOT SE 3
- Precautionary statements
- P501-P260-P270-P202-P240-P210-P233-P201-P243-P241-P242-P271-P264-P280-P370+P378-P308+P311-P303+P361+P353-P301+P330+P331-P363-P301+P312+P330-P304+P340+P310-P305+P351+P338+P310-P403+P233-P403+P235-P405
- Hazardous Substances Data
- 97-94-9(Hazardous Substances Data)
Chemistry & industry
Uses & manufacturing
Uses
Used as a fuel additive, fuel igniter, polymerization catalyst, and intermediate; [HSDB] Used in organic syntheses (radical initiator and blocking agent); [Merck Index]
Petroleum Production and Refining [Category: Industry]
Fuel additive; igniter or fuel for jet and rocket engines; olefin polymerization catalyst; intermediate
Triethylborane (TEB) is used by the USAF as a fuel additive to nonhypergolic propellants to increase fuel ignition speed and retard engine flameout.
General Manufacturing Information
Borane, triethyl-: ACTIVE
Mixtures with triethylaluminum have been used as hypergolic igniters for rocket propulsion systems.
Because of the low volume of organoboranes and the expensive raw material that are required for manufacture, organoboranes are expensive /chemical products/.
Applications
UsesReagent in organic syntheses blocking agent and radical initiator.
UsesTriethylborane reacted with 8-hydroxyquinoline to synthesize three 8--hydroxyquinolato (q) boron compounds B(C2H5)2q (1), BPh2q (2), and B(2-naph)2q (3).
UsesIt is used in mixtures with triethylaluminumas hypergolic igniters in rocket propulsionsystems.
Preparation methods
PreparationTriethylborane is prepared by reacting triethylaluminium with boron halides or by reacting diborane with ethylene: (C₂H₅)₃Al + BCl₃ → (C₂H₅)₃B + AlCl₃B₂H₆ + CH₂=CH₂ → (C₂H₅)₃B
Upstream & downstream products
Downstream products
Suppliers50 total
Related reactions
Linked notes
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