PRODUCTS

BORANE-DIMETHYLSULFIDE COMPLEX

Borane-dimethylsulfide complex is used with pinene to produce montelukast sodium and entecavir.
Borane-dimethylsulfide complex is used CBS-catalyzed asymmetric reduction of ferrocenyl-1,3-diketone into chiral 1,3-diol.
Borane-dimethylsulfide complex is used with a dendrimeric supported L-pyrrolidinol in the asymmetric reduction of indanones and tetralones.

CAS Number: 13292‑87‑0
EC Number (EINECS): 236‑313‑6
Molecular Formula: (CH₃)₂S·BH₃ (C₂H₉BS)
Molecular Weight: ≈ 75.96–75.97 g/mol

SYNONYMS:
BMS, Borane‑dimethyl sulfide, (Dimethyl sulfide)trihydroboron, Dimethyl sulfide‑borane complex, BMS, Dimethylsulfide borane complex, (Dimethyl sulfide)trihydroboron, DMSB, borane-methyl sulfide, DIMETHYL SULFIDE BORANE, BORANE-DIMETHYLSULFIDE, BORANE-DIMETHYLSULFIDE COMPLEX, borane dimethyl sulfide complex solution, Borane dimethyL, Borane-dimethylsulfide, Borane dimethylsulfide complex, Dimethyl sulfide borane, Boron, trihydro[thiobis[methane]]-, (T-4)-, Methyl sulfide, compd. with borane (1:1), Borane, compd. with dimethylsulfide, dimethyl sulphide--borane, Dimethyl sulfide-borane complex, dimethyl sulfide borane, borane-methyl sulfide complex, borane dimethyl sulfide complex, borane-dimethyl sulfide, dimethyl sulfideborane, dimethyl sulfide trihydroboron, borane-dimethyl sulfide complex, borane methylsulfide, borane dimethylsulfide, borane dms, Borane-dimethylsulfide, Borane dimethylsulfide complex, Dimethyl sulfide borane, Boron, trihydro[thiobis[methane]]-, (T-4)-, Methyl sulfide, compd. with borane (1:1), Borane, compd. with dimethylsulfide, dimethyl sulphide--borane, Dimethyl sulfide-borane complex, Borane-dimethyl sulfide complex, Borane, compd. with Thiobis[methane] (1:1), Borine, compd. with Me2S, Methyl Sulfide, compd. with BH3, Methyl sulfide, compd. with Borane (1:1), (T-4)-Trihydro[thiobis[methane]]boron, Borane, compd. with Methyl Sulfide (1:1), Thiobismethane Boron Complex, Thiobismethane compd. with Borane (1:1), (Dimethyl sulfide)borane, (Dimethyl sulfide)trihydroboron, BMS, Borane-dimethyl sulfide, Borane-dimethylsulfide Complex, Dimethylsulfane compd. with Borane (1:1), Dimethylsulfide Trihydroborane, Trihydrido(dimethyl Sulfide)boron, Trihydro(dimethylsulfide)boron, BMS, Dimethyl sulfide borane, (Dimethyl sulfide)trihydroboron, Borane dimethylsulfide complex, Borane, compd. with dimethylsulfide, Borane-dimethylsulfide, Boron, trihydro[thiobis[methane]]-, (T-4)-, Dimethyl sulfide-borane complex, Methyl sulfide, compd. with borane (1:1), dimethyl sulphide--borane, BMS, Dimethyl sulfideborane, Borane-methyl sulphide, Borane dimethyl sulfide, dimethyl sulphide-borane, Borane-methylsulfide complex, Borane-methyl sulfide complex, Dimethylsulfide borane complex, Trihydro[thiobis[methane]]boron, Borane dimethyl sulphide complex, Borane dimethyl sulphide complex, Borane diMethyl sulfide coMplex, 2.0 M solution in THF, SpcSeal, Borane diMethyl sulfide coMplex, 10.0 M solution in DMS, SpcSeal, Borane dimethyl sulfide complex solution 1.0 M in methylene chloride, Borane diMethyl sulfide coMplex, 2.0 M solution in toluene, SpcSeal, Borane diMethyl sulfide coMplex, 5.0 M solution in diethyl ether, SpcSeal, Borane diMethyl sulfide coMplex, 1.0 M solution in Methylene chloride, SpcSeal

Borane-dimethylsulfide complex is a complex of borane with dimethylsulfide.
The other common complex of borane is borane-THF.
Borane-dimethylsulfide complex is more stable than borane-THF and is therefore available in higher concentrations.

Borane-dimethylsulfide complex has the drawback of being smelly due to its dimethylsulfide content.
Borane-dimethylsulfide complex is for commercial use only and strictly NOT for human or animal consumption.
Borane-dimethylsulfide complex is a chemical compound with the chemical formula BH3·S(CH3)2.

Borane-dimethylsulfide complex is an adduct between borane molecule (BH3) and dimethyl sulfide molecule (S(CH3)2).
Borane-dimethylsulfide complex is a complexed borane reagent that is used for hydroborations and reductions.
The advantages of Borane-dimethylsulfide complex over other borane reagents, such as borane-tetrahydrofuran, are its increased stability and higher solubility.

Borane-dimethylsulfide complex is commercially available at much higher concentrations than its tetrahydrofuran counterpart (10 M) and does not require sodium borohydride as a stabilizer, which could result in undesired side reactions.
In contrast, BH3·THF requires sodium borohydride to inhibit reduction of THF to tributyl borate (B(OCH2CH2CH2CH3)3).

Borane-dimethylsulfide complex is soluble in most aprotic solvents.
Borane-dimethylsulfide complex is a stable source of borane used in hydroboration reduction reactions in organic synthesis.
Studies indicate that Borane-dimethylsulfide complex can selectively suppress α-hydroxyesters.

Borane-dimethylsulfide complex is a complex of diborane.
Borane-dimethylsulfide complex must be handled with extreme care and must be transported and stored at temperatures below -20°C.
Borane-dimethylsulfide complex is a chemical compound with the chemical formula BH3·S(CH3)2.

Borane-dimethylsulfide complex is soluble in most aprotic solvents.
Borane-dimethylsulfide complex acts as a highly efficient and selective reducing agent in the presence of catalytic sodium tetrahydroborate for α-hydroxy esters.

Asymmetric borane reduction of a variety of prochiral ketones with Borane-dimethylsulfide complex using spiroborate esters as catalyst has been reported.

Borane-dimethylsulfide complex is a colorless, water-reactive borane complex favored in organic synthesis due to its stability and high reactivity.
Borane-dimethylsulfide complex serves effectively in hydroboration and reduction reactions.
Handling demands strict moisture exclusion, inert atmosphere storage, proper PPE, and careful waste management.

USES and APPLICATIONS of BORANE-DIMETHYLSULFIDE COMPLEX:
Borane-dimethylsulfide complex is used with pinene to produce montelukast sodium and entecavir.
Together with L-pyrrolidone alcohol supported by dendrimer, Borane-dimethylsulfide complex is used for asymmetric reduction of indenone and tetrahydronaphthone.

Borane-dimethylsulfide complex is used CBS-catalyzed asymmetric reduction of ferrocenyl-1,3-diketone into chiral 1,3-diol.
Highly asymmetric reduction of ketones catalyzed by C3-symmetric tripoxylamide.
Reactants are used as reducing agents for specific selection.

Reactants participate in: Hydroboration reaction/oxidation of cage compounds.
Borane-dimethylsulfide complex is used with a dendrimeric supported L-pyrrolidinol in the asymmetric reduction of indanones and tetralones.
CBS-catalyzed asymmetric reduction of ferrocenyl-1,3-diketones to chiral 1,3-diols.

Highly enantioselective reduction of ketones catalyzed by C3-symmetric tripodal hydroxyamides.
Reactant used as a regioselective reducing agent.

Reactant involved in:
• Hydroboration / oxidation
• Synthesis of cage compounds

Borane-dimethylsulfide complex is a reducing agent used in organic synthesis.
Borane-dimethylsulfide complex is used in the reduction of α-hydroxy esters.
Borane-dimethylsulfide complex is used for hydroboration and reduction reactions.

Borane-dimethylsulfide complex is used in the reduction of aldehydes, ketones, epoxides and carboxylic acids to give corresponding alcohols.
Borane-dimethylsulfide complex is also involved in the Corey-Itsuno reduction.
Borane-dimethylsulfide complex acts as an intermediate in the preparation of highly pure semiconductor.

Borane-dimethylsulfide complex is also employed as a rocket propellant.
Borane-dimethylsulfide complex can be used as a reagent.
Borane-dimethylsulfide complex is used for the selective synthesis of 1,3,5-oxygenated compounds from dimethyl 3-oxoglutarate.

Borane-dimethylsulfide complex is used for the conversion of ozonides to alcohols.
In the CBS-catalyzed asymmetric reduction of ferrocenyl-1,3-diketones to 1,3-diols.
Borane-dimethylsulfide complex is used for enantioselective reduction of ketones to chiral secondary alcohols in the presence of C3-symmetric tripodal hydroxyamide as a ligand.

Borane-dimethylsulfide complex is used for the hydroboration reduction and other applications.
Borane-dimethylsulfide complex is used with a dendrimeric supported L-pyrrolidinol in the asymmetric reduction of indanones and tetralones.
Borane-dimethylsulfide complex is a clear colorless to light yellow solution.

Borane-dimethylsulfide complex is used for hydroborations and reductions.
Borane-dimethylsulfide complex is used with a dendrimeric supported L-pyrrolidinol in the asymmetric reduction of indanones and tetralones.
CBS-catalyzed asymmetric reduction of ferrocenyl-1,3-diketones to 1,3-diols.

Borane-dimethylsulfide complex is used highly enantioselective reduction of ketones catalyzed by C3-symmetric tripodal hydroxyamides.
Borane-dimethylsulfide complex is used for hydroboration and reduction reactions.
Borane-dimethylsulfide complex is used in the reduction of aldehydes, ketones, epoxides and carboxylic acids to give corresponding alcohols.

Borane-dimethylsulfide complex is also involved in the Corey-Itsuno reduction.
Borane-dimethylsulfide complex acts as an intermediate in the preparation of highly pure semiconductor.
Borane-dimethylsulfide complex is also employed as a rocket propellant.

Borane-dimethylsulfide complex is used in hydroborations.
Borane-dimethylsulfide complex offers interesting applications in the reduction of various functional groups.

The most interesting application of Borane-dimethylsulfide complex is as a borane source for oxazeborolidine catalyzed asymmetric reductions of ketones (Corey-Bakshi-Shibata Reduction).
Very interesting is also the direct reduction of carboxylic acids to alcohols (Borane-dimethylsulfide complex) and amides to amines (BTHF).

PRACTICAL USES & BENEFITS of BORANE-DIMETHYLSULFIDE COMPLEX:
Borane-dimethylsulfide complex is the preferred borane reagent due to high concentration and stability.
Borane-dimethylsulfide complex is widely used for hydroboration reactions (alkenes, silanes) and selective reductions of functional groups.
Borane-dimethylsulfide complex is advantageous for moisture-sensitive or air-tolerant procedures; excellent stability compared to BH₃·THF.

SOLUBILITY of BORANE-DIMETHYLSULFIDE COMPLEX:
Borane-dimethylsulfide complex is miscible with ethyl ether, dichloromethane, benzene, xylene, hexane, diglyme, dimethyl ether, ethyl acetate, toluene, methylene chloride and other aprotic solvents.

NOTES of BORANE-DIMETHYLSULFIDE COMPLEX:
Borane-dimethylsulfide complex has air and moisture sensitive.
Keep Borane-dimethylsulfide complex the container tightly closed in a dry and well-ventilated place.
Store Borane-dimethylsulfide complex in a cool place.
Borane-dimethylsulfide complex is incompatible with acids, water, alcohols, bromine, acid anhydrides, acid chlorides and oxidizing agents.

PREPARATION AND STRUCTURE of BORANE-DIMETHYLSULFIDE COMPLEX:
Although usually purchased, Borane-dimethylsulfide complex can be prepared by absorbing diborane into dimethyl sulfide:
B2H6 + 2 S(CH3)2 → 2 BH3·S(CH3)2

Borane-dimethylsulfide complex can be purified by bulb to bulb vacuum transfer.
Although a structure of Borane-dimethylsulfide complex has not been determined crystallographically, (pentafluorophenyl)-borane dimethylsulfide (C6F5BH2·S(CH3)2), has been examined by X-ray crystallography.
The boron atom adopts a tetrahedral molecular geometry.

REACTIONS of BORANE-DIMETHYLSULFIDE COMPLEX:
*Hydroborations
Due to the experimental ease of its use, Borane-dimethylsulfide complex has become common in hydroboration reactions.
In hydroborations with Borane-dimethylsulfide complex, the dimethylsulfide dissociates in situ, liberating diborane, which rapidly adds to the unsaturated bonds.

The resulting organoborane compounds are useful intermediates in organic synthesis.
Boranes add to alkenes in an anti-Markovnikov fashion and allow conversion of alkynes to the corresponding cis-alkenes.

*Reductions
Borane-dimethylsulfide complex has been employed for the reduction of many functional groups.
Reductions of aldehydes, ketones, epoxides, esters, and carboxylic acids give the corresponding alcohols.
Lactones are reduced to diols, and nitriles are reduced to amines.

Acid chlorides are not reduced by Borane-dimethylsulfide complex.
Borane dimethylsulfide is one of the most common bulk reducing agents used in the Corey–Itsuno reduction.
The dimethylsulfide ligand attenuates the reactivity of the borane.

Activation by the nitrogen of the chiral oxazaborolidine catalyst of the stoichiometric reducing agent allows for asymmetric control of the reagent.
In general Borane-dimethylsulfide complex does not lead to significantly greater enantiomeric selectivities than borane-THF, however its increased stability in the presence of moisture and oxygen makes it the reagent of choice for the reduction.

STRUCTURE & REACTIVITY of BORANE-DIMETHYLSULFIDE COMPLEX:
A Lewis acid–base adduct:
BH₃ binds the dimethyl sulfide ligand, forming a tetrahedral boron center.
In situ releases diborane for hydroboration of alkenes/alkynes in anti‑Markovnikov fashion.

Effective reducing agent:
converts aldehydes, ketones, epoxides, esters, carboxylic acids, lactones, nitriles → alcohols/amines; does not reduce acid chlorides.
More stable and higher concentration available (up to 10 M) than BH₃·THF; no sodium borohydride needed.
Preferred in asymmetric reductions (CBS) thanks to ligand-controlled activity.

PHYSICAL and CHEMICAL PROPERTIES of BORANE-DIMETHYLSULFIDE COMPLEX:
Chemical formula: BH3·S(CH3)2
Molar mass: 75.96 g/mol
Appearance: colorless liquid
Density: 0.801 g/mL
CAS Number: 13292‑87‑0
EC Number (EINECS): 236‑313‑6
PubChem CID: 12423031
Molecular Formula: (CH₃)₂S·BH₃ (C₂H₉BS)
Molecular Weight: ≈ 75.96–75.97 g/mol
Appearance: Colorless liquid
Density: 0.801 g/mL @ 25 °C

Flash Point: ~18 °C (64 °F)
Boiling / Melting Point: >36 °C; water-reactive
Solubility: Reacts violently with water (emits flammable gases);
soluble in THF, toluene, DCM, diethyl ether
CBNumber: CB3700534
Molecular Formula: C2H10BS
Molecular Weight: 76.97
MDL Number: MFCD00013189
MOL File: 13292-87-0.mol
Melting point: -40 to -37 °C
Boiling point: ~34 °C

Density: 1.287 g/mL at 25 °C
Refractive index: 1.4570
Flash point: 65 °F
Storage temp.: 2-8 °C
Solubility: Miscible with ethyl ether, tetrahydrofuran,
dichloromethane, benzene, xylene, hexane, diglyme, dimethyl ether,
ethyl acetate, toluene, methylene chloride and other aprotic solvents.
Form: Solution
Color: Colorless to pale yellow
Specific Gravity: 0.801

Water Solubility: reacts
Sensitive: Air & Moisture Sensitive
BRN: 3663489
InChIKey: RMHDLBZYPISZOI-UHFFFAOYSA-N
CAS DataBase Reference: 13292-87-0 (CAS DataBase Reference)
EWG's Food Scores: 1
FDA UNII: 6AVE9SRR08
NIST Chemistry Reference: Borane-methyl sulfide complex (13292-87-0)
EPA Substance Registry System: Boron, trihydro[thiobis[methane]]-, (T-4)- (13292-87-0)
UNSPSC Code: 12352112
NACRES: NA.22

CAS: 13292-87-0
Density: 0.801
Flash Point: −1 °C (30 °F)
Refractive Index: 1.457
MDL Number: MFCD00013189
UN Number: UN2924
Sensitivity: Air and moisture sensitive
Solubility Information: Miscible with ethyl ether, dichloromethane, benzene,
xylene, hexane, diglyme, dimethyl ether, ethyl acetate, toluene,
methylene chloride and other aprotic solvents.
SMILES: B.CSC

Molecular Weight (g/mol): 75.96
Formula Weight: 75.97
Chemical Name or Material: Borane-dimethyl sulfide complex
Melting Point: -38 °C
Boiling Point: ∼44 °C (decomposition)
Molecular Formula: C2H9BS
Linear Formula: (CH3)2S·BH3
Quantity: 25 mL
Beilstein: 3663489
CAS Number: 13292-87-0

Molecular Weight: 75.96 g/mol
Appearance: Colorless liquid
Melting Point: -38 °C
Density: 0.801 g/mL at 25 °C
InChI: InChI=1S/C2H9BS/c1-4(2)3/h1-3H3
InChI Key: IRTZFNXVGJHNHS-UHFFFAOYSA-N
Formula: C2H6S.BH3
SMILES: [BH2-]S+C
Molecular Weight1: 75.97
CAS: 13292-87-0
CAS: 13292-87-0

EINECS: 236-313-6
InChI: InChI=1/C2H6S.BH3/c1-3-2;/h1-2H3;1H3
InChIKey: RMHDLBZYPISZOI-UHFFFAOYSA-N
Molecular Formula: C2H10BS
Molar Mass: 76.97
Density: 1.287 g/mL at 25 °C
Melting Point: -40 to -37 °C
Boiling Point: ~34 °C
Flash Point: 65 °F

Water Solubility: reacts
Solubility: Miscible with ethyl ether, tetrahydrofuran, dichloromethane, benzene,
xylene, hexane, diglyme, dimethyl ether, ethyl acetate, toluene,
methylene chloride and other aprotic solvents.
Appearance: Light yellow solution
Specific Gravity: 0.801
Color: Colorless to pale yellow
BRN: 3663489
Storage Condition: 2-8 °C
Sensitive: Air & Moisture Sensitive
Refractive Index: 1.4570
MDL: MFCD00013189

FIRST AID MEASURES of BORANE-DIMETHYLSULFIDE COMPLEX:
-Description of first-aid measures
*General advice:
Show this material safety data sheet to the doctor in attendance.
*If inhaled:
After inhalation:
Fresh air.
*In case of skin contact:
Take off immediately all contaminated clothing.
Rinse skin with
water/ shower.
*In case of eye contact:
After eye contact:
Rinse out with plenty of water.
Call in ophthalmologist.
Remove contact lenses.
*If swallowed:
After swallowing:
Immediately make victim drink water (two glasses at most).
Consult a physician.
-Indication of any immediate medical attention and special treatment needed.
No data available

ACCIDENTAL RELEASE MEASURES of BORANE-DIMETHYLSULFIDE COMPLEX:
-Environmental precautions:
Do not let product enter drains.
-Methods and materials for containment and cleaning up:
Cover drains.
Collect, bind, and pump off spills.
Observe possible material restrictions.
Take up dry.
Dispose of properly.
Clean up affected area.

FIRE FIGHTING MEASURES of BORANE-DIMETHYLSULFIDE COMPLEX:
-Extinguishing media:
*Suitable extinguishing media:
Carbon dioxide (CO2)
Foam
Dry powder
*Unsuitable extinguishing media:
For this substance/mixture no limitations of extinguishing agents are given.
-Further information:
Prevent fire extinguishing water from contaminating surface water or the ground water system.

EXPOSURE CONTROLS/PERSONAL PROTECTION of BORANE-DIMETHYLSULFIDE COMPLEX:
-Control parameters:
--Ingredients with workplace control parameters:
-Exposure controls:
--Personal protective equipment:
*Eye/face protection:
Use equipment for eye protection.
Safety glasses
*Body Protection:
protective clothing
*Respiratory protection:
Recommended Filter type: Filter A
-Control of environmental exposure:
Do not let product enter drains.

HANDLING and STORAGE of BORANE-DIMETHYLSULFIDE COMPLEX:
-Conditions for safe storage, including any incompatibilities:
*Storage conditions:
Tightly closed.
Dry.

STABILITY and REACTIVITY of BORANE-DIMETHYLSULFIDE COMPLEX:
-Chemical stability:
The product is chemically stable under standard ambient conditions (room temperature).
-Possibility of hazardous reactions:
No data available