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Cas Database

121-43-7

121-43-7

Identification

  • Product Name:Trimethyl borate

  • CAS Number: 121-43-7

  • EINECS:204-468-9

  • Molecular Weight:103.914

  • Molecular Formula: C3H9BO3

  • HS Code:2920.90

  • Mol File:121-43-7.mol

Synonyms:NSC 777;Trimethoxyborane;Trimethoxyborine;Trimethoxyboron;Boricacid (H3BO3), trimethyl ester;Methylborate ((MeO)3B) (6CI);Borester O;Boric acid trimethyl ester;Borontrimethoxide;

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Safety information and MSDS view more

  • Pictogram(s):HarmfulXn,FlammableF

  • Hazard Codes:Xn,F,T

  • Signal Word:Warning

  • Hazard Statement:H226 Flammable liquid and vapourH312 Harmful in contact with skin

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician. In case of skin contact Wash off with soap and plenty of water. Consult a physician. In case of eye contact Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician. If swallowed Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.

  • Fire-fighting measures: Suitable extinguishing media Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. Wear self-contained breathing apparatus for firefighting if necessary.

  • Accidental release measures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Pick up and arrange disposal. Sweep up and shovel. Keep in suitable, closed containers for disposal.

  • Handling and storage: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Avoid exposure - obtain special instructions before use.Provide appropriate exhaust ventilation at places where dust is formed. For precautions see section 2.2. Store in cool place. Keep container tightly closed in a dry and well-ventilated place.

  • Exposure controls/personal protection:Occupational Exposure limit valuesBiological limit values Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. Eye/face protection Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin protection Wear impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique(without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Respiratory protection Wear dust mask when handling large quantities. Thermal hazards

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  • Manufacture/Brand:Usbiological
  • Product Description:trimethyl
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  • Manufacture/Brand:Usbiological
  • Product Description:Trimethyl
  • Packaging:250mg
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  • Product Description:Trimethyl
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  • Manufacture/Brand:Usbiological
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  • Product Description:Trimethyl Borate (63-65% in Methanol)
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Relevant articles and documentsAll total 58 Articles be found

de Moor,J.E.,van der Kelen,G.P.

, p. 235 - 241 (1966)

Schlesinger, H. I.,Brown, H. C.,Gilbreath, J. R.,Katz, J. J.

, p. 195 - 199 (1953)

Burg, A. B.,Schlesinger, H. I.

, p. 4020 - 4025 (1933)

Arquet

, p. 1422 (1936)

Infrared spectra of B(OMe)3, ClB(OMe)2 and Cl2BOMe species, isolated CH streching frequencies and bond strengths

McKean, D. C.,Coats, A. M.

, p. 409 - 420 (1989)

Infrared spectra in the gas phase are reported over the range 3100-500 cm-1 for species of B(OMe)3, ClB(OMe)2 and Cl2BOMe, with CH3, CD3 and CHD2 substitution.A detailed analysis of νCH and νCD data in all three species of Cl2BOMe yields strong evidence for the presence of three kinds of CH bond, two of them weak and one of them strong.The methyl group is then twisted, probably through 10-20 deg, out of the eclipsed or staggered conformation.The CHD2 spectra of the di and trimethoxy compounds are less susceptible to analysis, but suggest also the presence of two weak and strong bonds, the former increasing in weakness as the number of methoxy groups increases.This is as expected from the increased competition likely between the lone pair electrons for the empty boron orbital.The spectra of the CD3 species permit a clear assignment of νBO, δsCH3, δsCD3 and δasCD3 modes.In Cl(COCH3)2, νsBO lies at 1278 cm-1.

Brown et al.

, p. 5400,5404 (1957)

Action of Lewis acids upon base-pentaborane(9) adducts

Burg, Anton B.,Maya, Leon

, p. 942 - 944 (1975)

-

Webster, S. H.,Dennis, L. M.

, p. 3233 - 3235 (1933)

-

, p. 213 - 215 (1953)

-

Weissbach

, p. 329 (1958)

Burg,Mahler

, p. 4242 (1957)

Rehydrogenation of aminoboranes to amine-boranes using H2O: Reaction scope and mechanism

Leitao, Erin M.,Manners, Ian

, p. 2199 - 2205 (2015)

Water has been successfully employed as a reagent with which to rehydrogenate aminoboranes (e.g., iPr2N=BH2, 2,2,6,6-Me4C5H6N=BH2, and also transient Me2N=BH2 derived from 1/2[Me2N-BH2]2) to amine-boranes (e.g., iPr2NH·BH3, 2,2,6,6-Me4C5H6NH·BH3, Me2NH·BH3) in approximately 30 yield. The conversion to amine-boranes from the corresponding aminoboranes using this method represents an example of a metal-free, single-step route for the hydrogenation of the B=N bond. Deuterium labeling studies indicated that the protic hydrogen (N-H) on the rehydrogenated amine-borane was derived from H2O, whereas the third hydridic hydrogen (B-H) on the amine-borane was generated from the formation of a postulated hydride-bridged intermediate H2B(μ-H)(μ-NR2)B(OH)H (R2 = Me2, iPr2, 2,2,6,6-Me4C5H6), which requires a second equivalent of the starting aminoborane, thus explaining the low yield. Formation of insoluble borates (BxOyHz) provides a driving force for the reaction. Significantly, the yield can be increased by adding a sacrificial source of BH3 (e.g., to ca. 53% for BH3·THF) or by adding a separate source of H- (e.g., to ca. 95% for LiBH4) to complement the H+ (from H2O) in a more atom-efficient reaction.

The alcoholysis of carbon monoxide borane

Malone, Leo J.

, p. 1039 - 1040 (1968)

-

Murphy, C. B.,Enrione, R. E.

, p. 584 - 587 (1971)

Study of the reaction between boron trifluoride methanol complex and sodium methoxide

Wuke, Lang,Weijiang, Zhang,Jiao, Xu,Lei, Zhang

, p. 1530 - 1540 (2014)

The reaction between boron trifluoride methanol complex and sodium methoxide in methanol solution was investigated using conductivity as the reaction indicator. The reaction conditions were examined and a mechanism of this reaction was proposed. Moreover, proper reaction conditions were proposed for boric acid preparation using this reaction. 2014

Etridge, J. J.,Sugden, S.

, (1928)

The degradation of biscarborane

Hawthorne,Owen,Wiggins

, p. 1304 - 1306 (1971)

-

Preparation of energetic poly(azolyl)borates as new environmentally benign green-light-emitting species for pyrotechnics

Klapoetke, Thomas M.,Rusan, Magdalena,Sproll, Veronique

, p. 2433 - 2443 (2013)

Three different energetic poly(azolyl)borates, potassium dihydridobis(4-nitroimidazolyl)borate, sodium dihydridobis(4, 5-dinitroimidazolyl)borate, and sodium dihydridobis(3, 4,5-trinitropyrazolyl) borate, were synthesized as starting materials for metal-f

-

Brown,Mead

, p. 3614 (1956)

-

-

Voronkov,M.G.,Fedotova,L.A.

, (1968)

-

Wiesboeck, R. A.,Hawthorne, M. F.

, p. 1642 - 1643 (1964)

Pseudo Halide Chemistry in Ionic Liquids with Decomposable Anions

Harloff, J?rg,Schulz, Axel,Stoer, Philip,Villinger, Alexander

, p. 835 - 839 (2019)

Several pseudohalide containing ionic liquids with quarternary ammonium counter cations of the general formula [R3MeN]X [R = ethyl (1X), n-butyl (2X) with X– = CN–, N3 –, OCN–, and SCN–] were synthesized by decomposition of the corresponding trialkylammonium methylcarbonate in the reaction with Me3Si–X. We also treated 2CN with OP(OMe)3, yielding [nBu3MeN][O2P(OMe)2] and acetonitrile (Me-CN). The double salt [nBu3MeN]2{[B(OMe)3(CN)](CN)} was obtained from the reaction of 2CN with B(OMe)3, featuring the formation of the monocyanotrimethoxyborate anion, [B(OMe)3(CN)]–, co-crystallized with [nBu3MeN]CN. [nBu3MeN]2{[B(OMe)3(CN)](CN)} was fully characterized including structure elucidation.

Reaction of a 14-vertex carborane with nucleophiles: Formation of nido-C2B12, nido-C2B11, and closo-CB11 carborane anions

Zhang, Jian,Zheng, Fangrui,Chan, Hoi-Shan,Xie, Zuowei

, p. 9786 - 9791 (2009)

Nucleophilic reactions of a 14-vertex closo-carborane are reported. 2, 3-(CH2)3-2,3-C2B12H12 (1) reacts with MeOH at 70 °C to give closo-CB11 anions [1,2-(CH2)3CH(OMe)-1-CB11, H10] - ([2a]-), [1,2-(CH2)3CH(OMe)-1- CB11, H10]- ([2b]- ), and [1,2-(CH2)2CH=CH-1-CB11H10] - ([2c]- ). It is suggested that [2c]- is an intermediate for the isomerizatlon from [2a]- to [2b]- . Treatment of 1 with MeOH/Me3N, 'BuOK or LINMe2 affords nido-C2B12 species [8,9-(CH2) 3-μ-11, 12-(Nu)BH-8,9-C2B11H 11]-(Nu = MeO ([3a]-), BuO ([3b]-), and Me2N ([3c]-)). In the presence of acid such as HCl, anions [3]- are converted to 1. However, [3] undergo deboration reaction, in the presence of bases, to generate a nidO-C2B 11 anion [8, 9-(CH2)38,9-C2B 11H12]- ([4]-) that can also be formed directly from the reaction of 1 with excess CsF or piperidine. Mechanistic studies show that [3a]- is the first intermediate in the reaction of 1 with MeOH and [4]- Is unlikely an intermediate.

Hawthorne, M. F.,Joung, D. C.,Garrett, P. M.,Owen, D. A.,Svhwerin, S. G.,et al.

, p. 862 - 868 (1968)

Garrett, P. M.,Tebbe, F. N.,Hawthorne, M. F.

, p. 5016 - 5017 (1964)

Aluminum-Hydride-Catalyzed Hydroboration of Carbon Dioxide

Chia, Cher-Chiek,Teo, Yeow-Chuan,Cham, Ning,Ho, Samuel Ying-Fu,Ng, Zhe-Hua,Toh, Hui-Min,Mézailles, Nicolas,So, Cheuk-Wai

supporting information, p. 4569 - 4577 (2021/04/09)

This study describes the first use of a bis(phosphoranyl)methanido aluminum hydride, [ClC(PPh2NMes)2AlH2] (2, Mes = Me3C6H2), for the catalytic hydroboration of CO2. Complex 2 was synthesized by the reaction of a lithium carbenoid [Li(Cl)C(PPh2NMes)2] with 2 equiv of AlH3·NEtMe2 in toluene at -78 °C. 2 (10 mol %) was able to catalyze the reduction of CO2 with HBpin in C6D6 at 110 °C for 2 days to afford a mixture of methoxyborane [MeOBpin] (3a; yield: 78%, TOF: 0.16 h-1) and bis(boryl)oxide [pinBOBpin] (3b). When more potent [BH3·SMe2] was used instead of HBpin, the catalytic reaction was extremely pure, resulting in the formation of trimethyl borate [B(OMe)3] (3e) [catalytic loading: 1 mol % (10 mol %); reaction time: 60 min (5 min); yield: 97.6% (>99%); TOF: 292.8 h-1 (356.4 h-1)] and B2O3 (3f). Mechanistic studies show that the Al-H bond in complex 2 activated CO2 to form [ClC(PPh2NMes)2Al(H){OC(O)H}] (4), which was subsequently reacted with BH3·SMe2 to form 3e and 3f, along with the regeneration of complex 2. Complex 2 also shows good catalytic activity toward the hydroboration of carbonyl, nitrile, and alkyne derivatives.

Acetate-catalyzed hydroboration of CO2 for the selective formation of methanol-equivalent products

Dagorne, Samuel,Dos Santos, Jo?o H. Z.,Jacques, Béatrice,López, Carlos Silva,Nieto Faza, Olalla,Schrekker, Henri S.,Sokolovicz, Yuri C. A.,Specklin, David

, p. 2407 - 2414 (2020/05/13)

The present study details the use of the acetate anion, an inexpensive and robust anion, as a CO2 hydroboration catalyst for the selective formation, in most cases, of methanol-equivalent borane products. Thus, upon heating (90 °C, PhBr), tetrabutylammonium, sodium and potassium acetate (1, 2 and 3, respectively) effectively catalyze CO2 hydroboration by pinacolborane (pinB-H) to afford CO2 reduction products HOCOBpin (A), pinBOCH2OBpin (B) and methoxyborane (C). In most cases, high selectivity for product C with higher borane loading and longer reaction time with a TON of up to 970 was observed. The reduction catalysis remains efficient at low catalyst loading (down to 0.1 mol%) and may also be performed under solvent-free conditions using salt 1 as a catalyst, reflecting the excellent robustness and stability of the acetate anion. In control experiments, a 1/1 1/pinB-H mixture was found to react fast with CO2 at room temperature to produce formate species [pinB(O2CH)(OAc)][N(nBu)4] (5) through CO2 insertion into the B-H bond. DFT calculations were also performed to gain insight into the acetate-mediated CO2 hydroboration catalysis, which further supported the crucial role of acetate as a Lewis base in CO2 functionalization catalysis by pinB-H. The DFT-estimated mechanism is in line with experimental data and rationalizes the formation of the most thermodynamically stable reduction product C through acetate catalysis.

Ph2PCH2CH2B(C8H14) and Its Formaldehyde Adduct as Catalysts for the Reduction of CO2with Hydroboranes

Ramos, Alberto,Anti?olo, Antonio,Carrillo-Hermosilla, Fernando,Fernández-Galán, Rafael

supporting information, p. 9998 - 10012 (2020/07/24)

We study two metal-free catalysts for the reduction of CO2 with four different hydroboranes and try to identify mechanistically relevant intermediate species. The catalysts are the phosphinoborane Ph2P(CH2)2BBN (1), easily accessible in a one-step synthesis from diphenyl(vinyl)phosphine and 9-borabicyclo[3.3.1]nonane (H-BBN), and its formaldehyde adduct Ph2P(CH2)2BBN(CH2O) (2), detected in the catalytic reduction of CO2 with 1 as the catalyst but properly prepared from compound 1 and p-formaldehyde. Reduction of CO2 with H-BBN gave mixtures of CH2(OBBN)2 (A) and CH3OBBN (B) using both catalysts. Stoichiometric and kinetic studies allowed us to unveil the key role played in this reaction by the formaldehyde adduct 2 and other formaldehyde-formate species, such as the polymeric BBN(CH2)2(Ph2P)(CH2O)BBN(HCO2) (3) and the bisformate macrocycle BBN(CH2)2(Ph2P)(CH2O)BBN(HCO2)BBN(HCO2) (4), whose structures were confirmed by diffractometric analysis. Reduction of CO2 with catecholborane (HBcat) led to MeOBcat (C) exclusively. Another key intermediate was identified in the reaction of 2 with the borane and CO2, this being the bisformaldehyde-formate macrocycle (HCO2){BBN(CH2)2(Ph2P)(CH2O)}2Bcat (5), which was also structurally characterized by X-ray analysis. In contrast, using pinacolborane (HBpin) as the reductant with catalysts 1 and 2 usually led to mixtures of mono-, di-, and trihydroboration products HCO2Bpin (D), CH2(OBpin)2 (E), and CH3OBpin (F). Stoichiometric studies allowed us to detect another formaldehyde-formate species, (HCO2)BBN(CH2)2(Ph2P)(CH2O)Bpin (6), which may play an important role in the catalytic reaction. Finally, only the formaldehyde adduct 2 turned out to be active in the catalytic hydroboration of CO2 using BH3·SMe2 as the reductant, yielding a mixture of two methanol-level products, [(OMe)BO]3 (G, major product) and B(OMe)3 (H, minor product). In this transformation, the Lewis adduct (BH3)Ph2P(CH2)2BBN was identified as the resting state of the catalyst, whereas an intermediate tentatively formulated as the Lewis adduct of compound 2 and BH3 was detected in solution in a stoichiometric experiment and is likely to be mechanistically relevant for the catalytic reaction.

A Versatile NHC-Parent Silyliumylidene Cation for Catalytic Chemo- And Regioselective Hydroboration

Leong, Bi-Xiang,Lee, Jiawen,Li, Yan,Yang, Ming-Chung,Siu, Chi-Kit,Su, Ming-Der,So, Cheuk-Wai

supporting information, p. 17629 - 17636 (2019/11/11)

This study describes the first use of a silicon(II) complex, NHC-parent silyliumylidene cation complex [(IMe)2SiH]I (1, IMe =:C{N(Me)C(Me)}2) as a versatile catalyst in organic synthesis. Complex 1 (loading: 10 mol %) was shown to act as an efficient catalyst (reaction time: 0.08 h, yield: 94%, TOF = 113.2 h-1 reaction time: 0.17 h, yield: 98%, TOF = 58.7 h-1) for the selective reduction of CO2 with pinacolborane (HBpin) to form the primarily reduced formoxyborane [pinBOC(-O)H]. The activity is better than the currently available base-metal catalysts used for this reaction. It also catalyzed the chemo- and regioselective hydroboration of carbonyl compounds and pyridine derivatives to form borate esters and N-boryl-1,4-dihydropyridine derivatives with quantitative conversions, respectively. Mechanistic studies show that the silicon(II) center in complex 1 activated the substrates and then mediated the catalytic hydroboration. In addition, complex 1 was slightly converted into the NHC-borylsilyliumylidene complex [(IMe)2SiBpin]I (3) in the catalysis, which was also able to mediate the catalytic hydroboration.

Process route upstream and downstream products

Process route

4-difluoroboranyl-morpholine

4-difluoroboranyl-morpholine

Trimethyl borate
121-43-7,63156-11-6

Trimethyl borate

morpholin hydrochloride
10024-89-2

morpholin hydrochloride

Conditions
Conditions Yield
With calcium chloride; In methanol; byproducts: CaF2, HCl;
>99
>99
With CaCl2; In methanol; byproducts: CaF2, HCl;
>99
>99
(CH<sub>3</sub>O)H<sub>2</sub>N*BH<sub>3</sub>
91572-26-8

(CH3O)H2N*BH3

Trimethyl borate
121-43-7,63156-11-6

Trimethyl borate

hydrogen
1333-74-0

hydrogen

Conditions
Conditions Yield
In neat (no solvent); decompn. on heating to 90-300°C; discussion of react. mechanism;; residue of composition BN1.2(OCH3)0.1H1.3;; Kinetics;
(CH<sub>3</sub>O)(CH<sub>3</sub>)2N*BH<sub>3</sub>
127088-51-1

(CH3O)(CH3)2N*BH3

Trimethyl borate
121-43-7,63156-11-6

Trimethyl borate

hydrogen
1333-74-0

hydrogen

Conditions
Conditions Yield
In neat (no solvent); slow decompn. on heating up to 100°C; 50% decompn. on heating to 90°C for 24h;;
(CH<sub>3</sub>O)H<sub>2</sub>N*BH<sub>3</sub>
91572-26-8

(CH3O)H2N*BH3

tris(methoxy)borane*NH<sub>3</sub>
66794-43-2

tris(methoxy)borane*NH3

Trimethyl borate
121-43-7,63156-11-6

Trimethyl borate

ammonia
7664-41-7

ammonia

hydrogen
1333-74-0

hydrogen

Conditions
Conditions Yield
In neat (no solvent); byproducts: CH3OH; decompn. on heating to 55°C; discussion of react. mechanism;; Kinetics;
Trimethylmethoxysilane
1825-61-2

Trimethylmethoxysilane

benzenediazonium tetrafluoroborate
369-57-3

benzenediazonium tetrafluoroborate

Trimethyl borate
121-43-7,63156-11-6

Trimethyl borate

trimethylsilyl fluoride
420-56-4

trimethylsilyl fluoride

methoxybenzene
100-66-3

methoxybenzene

Conditions
Conditions Yield
In 1,1,2-Trichloro-1,2,2-trifluoroethane; 1.) 0 to 55 deg C very slowly, 2.) sonication, reflux, 16 h;
66%
51%
In 1,1,2-Trichloro-1,2,2-trifluoroethane; 1.) 0 to 55 deg C very slowly, 2.) sonication, reflux, 16 h; other alkyl(acyl)oxytrimethylsilanes;
51%
66%
Sn<sup>(4+)</sup>*4Br<sup>(1-)</sup>*B(OCH<sub>3</sub>)3=SnBr<sub>4</sub>*B(OCH<sub>3</sub>)3

Sn(4+)*4Br(1-)*B(OCH3)3=SnBr4*B(OCH3)3

Trimethyl borate
121-43-7,63156-11-6

Trimethyl borate

stannic bromide
7789-67-5

stannic bromide

Conditions
Conditions Yield
In neat (no solvent); decomposition reaction at 110°C in He atmosphere;
Sn<sup>(4+)</sup>*4Br<sup>(1-)</sup>*2B(OCH<sub>3</sub>)3=SnBr<sub>4</sub>*2B(OCH<sub>3</sub>)3

Sn(4+)*4Br(1-)*2B(OCH3)3=SnBr4*2B(OCH3)3

Trimethyl borate
121-43-7,63156-11-6

Trimethyl borate

stannic bromide
7789-67-5

stannic bromide

Conditions
Conditions Yield
In neat (no solvent); decomposition reaction at 90°C in He atmosphere;
bis(dimethylamino){tris(trimethylsilyl)silyl}borane
81175-91-9

bis(dimethylamino){tris(trimethylsilyl)silyl}borane

Trimethyl borate
121-43-7,63156-11-6

Trimethyl borate

(dimethylamino)dimethoxy borane
7318-74-3

(dimethylamino)dimethoxy borane

tris(dimethylamino)borane
4375-83-1

tris(dimethylamino)borane

Conditions
Conditions Yield
With methanol; In hexane; (under Ar); the borane is dissolved in hexane and treated with MeOH, mixt. is heated to 45°C; monitored by (11)B-NMR;
6%
8%
44%
4-difluoroboranyl-thiomorpholine

4-difluoroboranyl-thiomorpholine

Trimethyl borate
121-43-7,63156-11-6

Trimethyl borate

thiamorpholine hydrochloride
5967-90-8

thiamorpholine hydrochloride

Conditions
Conditions Yield
With calcium chloride; In methanol; byproducts: HCl, CaF2;
>99
>99
With CaCl2; In methanol; byproducts: HCl, CaF2;
>99
>99
malic acid dimethyl ester
38115-87-6

malic acid dimethyl ester

3-Hydroxytetrahydrofuran
453-20-3,84921-89-1,864447-89-2

3-Hydroxytetrahydrofuran

Trimethyl borate
121-43-7,63156-11-6

Trimethyl borate

D,L-1,2,4-butanetriol
3068-00-6,6810-31-7

D,L-1,2,4-butanetriol

Conditions
Conditions Yield
With methanol; sodium tetrahydroborate; In tetrahydrofuran; at 25 - 30 ℃; for 20h; Industry scale; Inert atmosphere;

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  • Country:China (Mainland)
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