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112022-81-8

112022-81-8

Identification

  • Product Name:1H,3H-Pyrrolo[1,2-c][1,3,2]oxazaborole,tetrahydro-1-methyl-3,3-diphenyl-, (3aS)-

  • CAS Number: 112022-81-8

  • EINECS:-0

  • Molecular Weight:277.174

  • Molecular Formula: C18H20BNO

  • HS Code:29349990

  • Mol File:112022-81-8.mol

Synonyms:1H,3H-Pyrrolo[1,2-c][1,3,2]oxazaborole,tetrahydro-1-methyl-3,3-diphenyl-, (S)-;(S)-3,3-Diphenyl-1-methylpyrrolidino[1,2-c]-1,3,2-oxazaborole;(S)-Tetrahydro-1-methyl-3,3-diphenyl-1H,3H-pyrrolo[1,2-c][1,3,2]oxazaborole;(3aS)-Tetrahydro-1-methyl-3,3-diphenyl-1H,3H-pyrrolo[1,2-c][1,3,2]oxazaborole;

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Safety information and MSDS view more

  • Pictogram(s):IrritantXi

  • Hazard Codes:Xi,Xn,F

  • Signal Word:Danger

  • Hazard Statement:H302 Harmful if swallowedH318 Causes serious eye damage

  • 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

Supplier and reference price

  • Manufacture/Brand
  • Product Description
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  • Manufacture/Brand:TRC
  • Product Description:(S)-2-Methyl-CBS-oxazaborolidine(1MinToluene)
  • Packaging:50ml
  • Price:$ 450
  • Delivery:In stock
  • Buy Now
  • Manufacture/Brand:TCI Chemical
  • Product Description:(S)-5,5-Diphenyl-2-methyl-3,4-propano-1,3,2-oxazaborolidine >98.0%(T)
  • Packaging:5g
  • Price:$ 333
  • Delivery:In stock
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  • Manufacture/Brand:TCI Chemical
  • Product Description:(S)-5,5-Diphenyl-2-methyl-3,4-propano-1,3,2-oxazaborolidine >98.0%(T)
  • Packaging:1g
  • Price:$ 84
  • Delivery:In stock
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  • Manufacture/Brand:Synthonix
  • Product Description:(S)-1-Methyl-3,3-diphenylhexahydropyrrolo[1,2-c][1,3,2]oxazaborole 97%
  • Packaging:25g
  • Price:$ 60
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  • Manufacture/Brand:Synthonix
  • Product Description:(S)-1-Methyl-3,3-diphenylhexahydropyrrolo[1,2-c][1,3,2]oxazaborole 97%
  • Packaging:5g
  • Price:$ 20
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  • Manufacture/Brand:Synthonix
  • Product Description:(S)-1-Methyl-3,3-diphenylhexahydropyrrolo[1,2-c][1,3,2]oxazaborole 97%
  • Packaging:10g
  • Price:$ 30
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  • Manufacture/Brand:Synthonix
  • Product Description:(S)-1-Methyl-3,3-diphenylhexahydropyrrolo[1,2-c][1,3,2]oxazaborole 97%
  • Packaging:1g
  • Price:$ 15
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  • Manufacture/Brand:Strem Chemicals
  • Product Description:(S)-Tetrahydro-1-methyl-3,3-diphenyl-1H,3H-pyrrolo[1,2-c][1,3,2]oxazaborole, 0.9-1.1M in toluene [(S)-Methyloxazaborolidine] (S)-CBS Catalyst
  • Packaging:50ml
  • Price:$ 437
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  • Manufacture/Brand:Strem Chemicals
  • Product Description:(S)-Tetrahydro-1-methyl-3,3-diphenyl-1H,3H-pyrrolo[1,2-c][1,3,2]oxazaborole, 0.9-1.1M in toluene [(S)-Methyloxazaborolidine] (S)-CBS Catalyst
  • Packaging:10ml
  • Price:$ 110
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:(S)-(?)-2-Methyl-CBS-oxazaborolidine ≥95%
  • Packaging:1g
  • Price:$ 68.4
  • Delivery:In stock
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Relevant articles and documentsAll total 17 Articles be found

An enantioselective approach to cytotoxic norcalamenenes via electron-transfer-driven benzylic umpolung of an arene tricarbonyl chromium complex

Schmalz, Hans-Guenther,Kiehl, Oliver,Korell, Ursula,Lex, Johann

, p. 1851 - 1855 (2003)

An efficient enantioselective total synthesis of (R)-1-isopropenyl-6-methoxy-7-methyl-1,2,3,4-tetrahydronaphthalene, the dehydro-analog of the cytotoxic norsesquiterpene (R)-7-demethyl-2-methoxycalamenene, was achieved in seven steps starting from 6-methoxytetralone. The synthesis exploits the specific reactivity and stereochemistry of planar chiral η6-arene-Cr(CO)3 complexes. In a key step, a Cr(CO)3-complexed benzylic anion, regioselectively generated by means of electron- transfer-driven benzylic umpolung, is diastereoselectively alkylated with acetyl chloride.

Chiral MeCBS synthesis process

-

Paragraph 0015; 0016, (2017/04/20)

The invention discloses a chiral MeCBS synthesis process. The process comprises the steps of adding 1.1-1.5 equivalent weight of methyl-boric acid in alkane solvent for back flow and water division, after the reaction is complete, lowering the temperature to 30-45 DEG C, after keeping static for filtration, lowering the filtered solution to below -20-0 DEG C, stirring and leaching out, after filtration and drying, acquiring the chiral MeCBS which is white solid with good fluidity. The processing method has the advantages of being simple in operation, being high in product purity, thus providing more choices in the current market with more available solvent types.

Stereospecific, Nickel-Catalyzed Suzuki-Miyaura Cross-Coupling of Allylic Pivalates to Deliver Quaternary Stereocenters

Cobb, Kelsey M.,Rabb-Lynch, Javon M.,Hoerrner, Megan E.,Manders, Alex,Zhou, Qi,Watson, Mary P.

supporting information, p. 4355 - 4358 (2017/08/23)

Recognizing the importance of all-carbon, quaternary stereocenters in complex molecule synthesis, a stereospecific, nickel-catalyzed cross-coupling of allylic pivalates with arylboroxines to deliver products equipped with quaternary stereocenters and internal alkenes was developed. The enantioenriched allylic pivalate starting materials are readily prepared, and a variety of functional groups can be incorporated on both the allylic pivalate and the arylboroxine. Additional advantages include the use of a commercially available and air-stable Ni(II) salt and BISBI ligand, mild reaction conditions, and high yields and ee's. The observed stereoinversion of this reaction is consistent with an open transition state in the oxidative addition step.

Enantioselective Desymmetrization of Glutarimides Catalyzed by Oxazaborolidines Derived from cis-1-Amino-indan-2-ol

Kutama, Ibrahim U.,Jones, Simon

, p. 11468 - 11479 (2015/12/04)

Enantioselective reductive desymmetrization of glutarimides has been achieved employing an oxazaborolidine catalyst derived from cis-1-amino-indan-2-ol. The reaction was found to proceed through a stereoablative process that upgraded the enantioselectivity of an intermediate hydroxy-lactam. The reaction was generally tolerant of a number of substituents in the 4-position, giving enantiomeric excesses of greater than 82%.

Enantioselective catalytic desymmetrization of maleimides by temporary removal of an internal mirror plane and stereoablative over-reduction: Synthesis of (R)-pyrrolam A

Marsh, Barrie J.,Adams, Harry,Barker, Mike D.,Kutama, Ibrahim U.,Jones, Simon

supporting information, p. 3780 - 3783 (2014/08/05)

A highly enantioselective (>95% ee) strategy to affect the desymmetrization of a maleimide has been performed by temporary attachment to an anthracene template followed by asymmetric reduction with an oxazaborolidine catalyst. A stereoablative over-reduction process was partially responsible for the high levels of enantioselectivity. Exemplification of the strategy by stereoselective functionalization and retro-Diels-Alder reaction provided the natural product pyrrolam A.

Rational electronic tuning of CBS catalyst for highly enantioselective borane reduction of trifluoroacetophenone

Korenaga, Toshinobu,Nomura, Kenji,Onoue, Kazutaka,Sakai, Takashi

supporting information; experimental part, p. 8624 - 8626 (2011/01/03)

α,α,α-Trifluoroacetophenone (2), which is susceptible to noncatalytic reduction by BH3, could be reduced to chiral alcohol up to 90% ee by using electronically tuned-CBS catalyst (1) with BH3. The enantioselectivities highly correlated with the differential orbital energies between 1-BH3 adduct and 2, which were calculated by DFT method.

Process route upstream and downstream products

Process route

C<sub>22</sub>H<sub>30</sub>BNO<sub>2</sub>

C22H30BNO2

methyldi-n-butoxyborane
86595-28-0

methyldi-n-butoxyborane

(S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole
112022-81-8,133261-83-3

(S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole

butan-1-ol
71-36-3

butan-1-ol

Conditions
Conditions Yield
In toluene; for 4h; Heating / reflux;
dihydroxy-methyl-borane
13061-96-6

dihydroxy-methyl-borane

(R)-α,α-diphenylprolinol
22348-32-9

(R)-α,α-diphenylprolinol

(S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole
112022-81-8,133261-83-3

(S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole

Conditions
Conditions Yield
In n-heptane; at 40 ℃; Solvent; Temperature; Inert atmosphere; Reflux; Large scale;
83%
Trimethylboroxine
823-96-1

Trimethylboroxine

(S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole
112022-81-8,133261-83-3

(S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole

Conditions
Conditions Yield
In toluene; at 20 ℃; for 0.6h;
In toluene;
In toluene; at 20 - 155 ℃;
(S)-diphenylprolinol; In toluene; at 50 ℃; Inert atmosphere;
Trimethylboroxine; In toluene; at 20 ℃; for 2h; Inert atmosphere;
(S)-diphenylprolinol; In toluene; at 140 - 150 ℃;
Trimethylboroxine; In toluene; at 20 ℃; for 0.583333h;
In toluene; at 20 ℃; for 1.5h;
In toluene; at 50 ℃; for 0.75h;
In toluene; for 0.5h; Inert atmosphere;
methylboronic acid

methylboronic acid

(S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole
112022-81-8,133261-83-3

(S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole

Conditions
Conditions Yield
In toluene; byproducts: H2O; refluxing of pyrrolidine deriv. and methylboronic acid in toluene for 3 h; evapn. of solvent in vac.;
86%
With 4 A molecular sieve; In toluene; byproducts: H2O; react. of pyrrolidine deriv. and methylboronic acid in toluene at 23°C in presence of molecular sieves within 1,5 h; evapn. of solvent in vac.;
86%
dihydroxy-methyl-borane
13061-96-6

dihydroxy-methyl-borane

(S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole
112022-81-8,133261-83-3

(S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole

Conditions
Conditions Yield
In toluene; for 3h; Heating;
With 4 A molecular sieve; In toluene; for 15h; Heating;
In toluene; for 14h; Heating;
In toluene; heating (60°C, 1 h), refluxing (5 h); solvent removal (distn.), cooling (23°C), solvent removal (vac., 40°C);
In toluene; for 4h; Dean-Stark; Reflux;
methylbis(diisopropylamino)borane
151293-60-6

methylbis(diisopropylamino)borane

(R)-α,α-diphenylprolinol
22348-32-9

(R)-α,α-diphenylprolinol

(S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole
112022-81-8,133261-83-3

(S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole

Conditions
Conditions Yield
In tetrahydrofuran; toluene; reflux for 30 min; solvents are removed;
89%
(S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole
112022-81-8,133261-83-3

(S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole

Conditions
Conditions Yield
(S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole
112022-81-8,133261-83-3

(S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole

Conditions
Conditions Yield
With water;
77%
1-(3-Bromophenyl)ethanone
2142-63-4

1-(3-Bromophenyl)ethanone

(S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole
112022-81-8,133261-83-3

(S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole

Conditions
Conditions Yield
With dimethyl sulfide borane; In tetrahydrofuran; toluene; at 30 ℃; for 7h;
54%
6-phenylsulfanyl-3,4-dihydro-2H-naphthalen-1-one
149915-80-0

6-phenylsulfanyl-3,4-dihydro-2H-naphthalen-1-one

(S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole
112022-81-8,133261-83-3

(S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole

(R)-6-phenylsulfanyl-1,2,3,4-tetrahydro-naphthalen-1-ol
895534-20-0

(R)-6-phenylsulfanyl-1,2,3,4-tetrahydro-naphthalen-1-ol

Conditions
Conditions Yield
6-phenylsulfanyl-3,4-dihydro-2H-naphthalen-1-one; (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole; With borane N,N-diethylaniline complex; In toluene; at 30 - 32 ℃; for 3h;
With hydrogenchloride; methanol; water; In toluene; for 0.666667h;
98%

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