Trimethyl borate

HCID 8470CAS 121-43-7

Basic information

Standard SMILES
COB(OC)OC
InChIKey
WRECIMRULFAWHA-UHFFFAOYSA-N
Molecular formula
C3H9BO3
Average molar mass
103.92 g/mol
Monoisotopic mass
104.06447455

Overview

Trimethyl borate appears as a water-white liquid. Denser than water. Vapors heavier than air. Used as a solvent and fungicide for fruit.

Names & identifiers

Preferred name
Trimethyl borate
IUPAC
trimethyl borate
English name
Trimethyl borate
Molecular formula
C3H9BO3
Molecular weight
103.91

Names & synonyms

TRIMETHYL BORATE121-43-7TrimethoxyboraneMethyl boratetrimethylborateTrimethoxyboronBoric acid trimethyl esterBorester OBoric acid, trimethyl esterTrimethoxyborineBoric acid (H3BO3), trimethyl esterTrimethylester kyseliny borite
Show more names
B(OMe)3trimethylB(OCH3)3C3H9BO3LobitridolTriMethyl boratBORON METHOXIDEborestero
NSC-77782U64J6F5NDTXSID0037738CHEBI:38913RefChem:191751DTXCID8017738204-468-9934-685-0

Database identifiers

CAS
121-43-7、3349-42-6
PubChem CID
8470
DTXSID
DTXSID0037738
ChEBI
CHEBI:38913
UNII
82U64J6F5N
EC Number
204-468-9、693-032-5、934-685-0
Nikkaji
J2.484H

Properties

Computed structural properties

Topological polar surface area
27.7 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
3
Rotatable bonds
3
Heavy atoms
7

Experimental & physicochemical properties

Chemical Classes · 2 items

Metals -> Metalloid Compounds (Boron)

Flammable agents - 3rd degree

LogP-1.9
Density · 3 items

0.915 g/cu cm

Relative density (water = 1): 0.915

0.92 @ 20°C

Color/FormColorless, moisture-sensitive liquid; fumes in air
Solubility · 3 items

Miscible with tetrahydrofuran, ether, isoporpylamine, hexane, methanol, nujol, and other organic liquids

Miscible with alcohol, ether; soluble in polar nonhydroxylic solvents

Solubility in water: reaction

Flash Point · 3 items

less than 80 °F (NFPA, 2010)

< 80 °F (< 27 °C) (closed cup)

- 7 °C

Physicochemical properties

Melting point
-34 °C · -34 °C (lit.)
Boiling point
68 · 68-69 °C (lit.)
Density
0.932 g/mL · 0.932 g/mL at 20 °C (lit.)
vapor density
3.59 · 3.59 (vs air)
vapor pressure
147.9 · 147.9-148 hPa ( 20 °C)
refractive index
20 · n20/D 1.358(lit.)

Safety & regulation

GHS classification

GHS Classification · 6 items

Danger

H226: Flammable liquid and vapor [Warning Flammable liquids]

P203, P210, P233, P240, P241, P242, P243, P280, P302+P352, P303+P361+P353, P317, P318, P321, P362+P364, P370+P378, P403+P235, P405, and P501 (click each P-code to see the statement)

Danger

H225 (40.5%): Highly Flammable liquid and vapor [Danger Flammable liquids]

P203, P210, P233, P240, P241, P242, P243, P260, P261, P262, P264, P264+P265, P270, P271, P280, P301+P316, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P308+P316, P316, P317, P318, P321, P330, P337+P317, P361+P364, P362+P364, P370+P378, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)

Hazard information

Regulatory Information · 6 items

Chemical: Boric acid (H3BO3), trimethyl ester

Hazard Traits - Reproductive Toxicity

Boric acid (H3BO3), trimethyl ester is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Boric acid (H3BO3), trimethyl ester 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: 01-07-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/14170

Boric acid, trimethyl ester: HSNO Approval: HSR001230 Approved with controls

The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)

DOT LabelFlammable Liquid
Fire Hazards · 3 items

Excerpt from ERG Guide 129 [Flammable Liquids (Water-Miscible / Noxious)]:

· HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames.

Highly flammable. Gives off irritating or toxic fumes (or gases) in a fire. Vapour/air mixtures are explosive.

Fire Potential · 2 items

Flammable, fire risk ...

A very dangerous fire hazard when exposed to heat, flame, or oxidizers.

Health Hazards · 2 items

Excerpt from ERG Guide 129 [Flammable Liquids (Water-Miscible / Noxious)]:

· May cause toxic effects if inhaled or absorbed through skin.

Hazards Summary · 1 item

A skin and eye irritant; Inhalation may cause cough and sore throat; [ICSC] Chronic poisoning in grazing animals where soil is high in boric acid results in vomiting, diarrhea, shock, convulsions, and paralysis; Post-mortem findings include inflammation of the GI tract, liver and kidney damage, and cerebral edema; [HSDB]

Safety & protection

Fire Fighting · 2 items

Excerpt from ERG Guide 129 [Flammable Liquids (Water-Miscible / Noxious)]:

Use foam, powder, carbon dioxide. In case of fire: keep drums, etc., cool by spraying with water. NO direct contact with water.

First Aid Measures · 4 items

Fresh air, rest.

Rinse skin with plenty of water or shower.

First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

Rinse mouth. Refer for medical attention .

Accidental Release Measures · 2 items

· CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.

· ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area.

First Aid · 2 items

Excerpt from ERG Guide 129 [Flammable Liquids (Water-Miscible / Noxious)]:

General First Aid:

Safe StorageFireproof. Separated from strong oxidants and strong acids. Dry.
Exposure Control and Personal Protection· Wear positive pressure self-contained breathing apparatus (SCBA).

Toxicology

Environmental Fate · 3 items

TERRESTRIAL FATE: Trimethyl borate is rapidly hydrolyzed to boric acid and methanol in the presence of water(1,2). Hydrolysis would be expected to be the dominate fate process for trimethyl borate in the environment(SRC).

AQUATIC FATE: Trimethyl borate is rapidly hydrolyzed to boric acid and methanol in the presence of water(1,2). Hydrolysis would be expected to be the dominate fate process for trimethyl borate in the environment(SRC).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), trimethyl borate, which has a vapor pressure of 136 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Trimethyl borate is rapidly hydrolyzed to boric acid and methanol in the presence of water(3,4). Hydrolysis would be expected to be the dominate fate process for trimethyl borate in the environment(SRC).

Adverse EffectsNeurotoxin - Other CNS neurotoxin
Exposure RoutesThe substance can be absorbed into the body by inhalation, through the skin and by ingestion.
Signs and Symptoms · 4 items

Cough. Sore throat.

Redness. Burning sensation.

Redness. Pain.

Burning sensation. Abdominal pain.

Medical SurveillanceNo specific considerations are needed for boric acid or borates except for general health and liver and kidney function. /Boric acid and borates/
Soil Adsorption/Mobility · 1 item

Trimethyl borate is rapidly hydrolyzed to boric acid and methanol in the presence of water(1,2). Hydrolysis would be expected to be the dominate fate process for trimethyl borate in the environment(SRC). Adsorption to soil or suspended particles in water is not considered an important environmental fate for trimethyl borate(SRC).

Regulatory information

State Drinking Water Guidelines · 5 items

(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/

Federal Drinking Water GuidelinesEPA 600 ug/L /Boron/

Safety data

F
21
PPE
Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
wgk
3
tsca
TSCA listed
rtecs
ED5600000
ridadr
UN 2416

Chemistry & industry

Uses & manufacturing

Uses · 6 items

Used as a flame retardant, welding and brazing flux, chemical intermediate, fungicide, and a solvent for waxes, resins, and oils; [HSDB]

Welding [Category: Weld]

As solvent for waxes, resins, oils; catalyst in manufacture of ketones; analysis of paint and varnish ingredients; as neutron detector gas in presence of a scintillation counter; as promoter of diborane reactions

Dehydrating agent; fungicide for citrus fruit

Intermediate in preparation of metal borohydrides

Azeotropic gaseous flux for welding and brazing

U.S. Production · 3 items

2023: 1,000,000 - <8,500,000 lb

(1979) PROBABLY GREATER THAN 4.54X10+6 G

Production figures for trimethyl borate were given as 21.1 million pound in 1977(1), most of which is used captively in the production of sodium borohydride(2).

Industry UsesNot Known or Reasonably Ascertainable
Methods of Manufacturing...From pyridine-boron trichloride complex; from methanol and boric oxide, borax or boric acid; from methyl orthosilicates and boron halide; from boric acid and methanol...
General Manufacturing Information · 6 items

Pharmaceutical and Medicine Manufacturing

Boric acid (H3BO3), trimethyl ester: ACTIVE

US 2689259; US 2884439; US 2937195 (to Callery Chem)

US 2881227 and US 2884440 (to Olin Mathieson)

US 2855427 (to Am. Potash & Chem.)

US 2739979 ( to USAEC)

Applications · 2 items

UsesTrimethyl borate is a useful reagent in organic synthesis. It is involved in the production of resins, waxes and paints and acts as a methylation agent. As a boron source, Trimethyl borate is used to prepare flame retardants, anti-oxidants and corrosion inhibitors. It reacts with Grignard reagents followed by hydrolysis to prepare boronic acid. It is also used as a precursor of borate esters, which finds application in the Suzuki coupling reaction. It is used as neutron detector gas in the presence of a scintillation counter; as a promoter of diborane reactions.

General DescriptionTrimethyl borate appears as a water-white liquid. Denser than water. Vapors heavier than air. Used as a solvent and fungicide for fruit.

Preparation methods · 1 item

PreparationThe preparation method of trimethyl borate1. The direct reaction between boric acid and methanol is as follows:3CH30H+H3B03→B (OCH3) 3+3H20Usually the trimethyl borate formed in the reaction forms an azeotrope with excess methanol and is distilled out together, and then the trimethyl borate is obtained by separating the azeotrope.2. The direct reaction between boron oxide and methanol is as follows:B203+6CH30H→2B (OCH3) 3+3H203. Borax, methanol and sulfuric acid are directly reacted, and the reaction formula is :Na2B4O7.1OH2O+12CH30H+2H2S04→4B (OCH3)3+2NaHS04+17H20

Suppliers6 total

上海瀚鸿科技股份有限公司021-54306202 13764082696 · [email protected]
南通市苏北化工原料有限公司0513-85290972 18762756250 · [email protected]
维百奥(北京)生物科技有限公司13621190864 13691409741 · [email protected]
SUZHOU SENFEIDA CHEMICAL CO.,LTD+86-0512-83500002 +86-15195660023 · [email protected]
宝鸡缔都医药化工有限公司029-029-81148929 17792602132 · [email protected]

Additional notes

DefinitionChEBI: Trimethyl borate is a member of the class of borate esters obtained by the formal condensation of three equivalents of methanol with boric acid.

Related reactions

1,498 records

Linked notes

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