[ CAS No. 112022-81-8 ] {[proInfo.proName]}

Name: 112022-81-8|(S)-1-Methyl-3,3-diphenylhexahydropyrrolo[1,2-c][1,3,2]oxazaborole|97% HPLC
Brand: Ambeed
SKU: A742072
Price: 45.0 USD
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Quality Control of [ 112022-81-8 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 112022-81-8 ]

SDS Specification

Alternatived Products of [ 112022-81-8 ]

Product Details of [ 112022-81-8 ]

CAS No. :	112022-81-8	MDL No. :	MFCD00078439
Formula :	C₁₈H₂₀BNO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	VMKAFJQFKBASMU-KRWDZBQOSA-N
M.W :	277.17	Pubchem ID :	2734713
Synonyms :

Calculated chemistry of [ 112022-81-8 ]

Physicochemical Properties

Num. heavy atoms :	21
Num. arom. heavy atoms :	12
Fraction Csp3 :	0.33
Num. rotatable bonds :	2
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	90.29
TPSA :	12.47 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	Yes
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	Yes
CYP3A4 inhibitor :	Yes
Log Kp (skin permeation) :	-5.06 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.0
Log Po/w (XLOGP3) :	4.13
Log Po/w (WLOGP) :	3.05
Log Po/w (MLOGP) :	3.01
Log Po/w (SILICOS-IT) :	2.22
Consensus Log Po/w :	2.48

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	0.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-4.45
Solubility :	0.00981 mg/ml ; 0.0000354 mol/l
Class :	Moderately soluble
Log S (Ali) :	-4.1
Solubility :	0.0221 mg/ml ; 0.0000797 mol/l
Class :	Moderately soluble
Log S (SILICOS-IT) :	-5.56
Solubility :	0.00077 mg/ml ; 0.00000278 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	4.13

Safety of [ 112022-81-8 ]

Signal Word:	Danger	Class:	N/A
Precautionary Statements:	P280-P301+P312+P330-P305+P351+P338+P310	UN#:	N/A
Hazard Statements:	H302-H318	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 112022-81-8 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 112022-81-8 ]
Downstream synthetic route of [ 112022-81-8 ]

[ 112022-81-8 ] Synthesis Path-Upstream 1~7

1
[ 112022-81-8 ]
[ 22348-32-9 ]

Reference： [1] Organic Syntheses, 2002, vol. 79, p. 72 - 72

2
[ 13061-96-6 ]
[ 22348-32-9 ]
[ 112022-81-8 ]

Yield	Reaction Conditions	Operation in experiment
83%	at 40℃; Inert atmosphere; Reflux; Large scale	Under nitrogen protection, In a reactor equipped with a reflux water separation device(S)-(+)-2-(diphenylhydroxymethyl)pyrrolidine (2.53 kg, 10 moles) and methylboronic acid (779 g, 13 moles) were added to 7.1 g of n-heptane, Slowly stirring, As the water is constantly being separated, The solution gradually becomes clear, Then adjust the stirring speed to the normal state, When there is no more water, Stop stirring, Slow down to 40 deg C, After standing overnight, Diatomaceous earth temperature filtration, The filtrate was once again cooled to -10 ° C, Stirring for 1.5 hours to complete precipitation, After filtration, 40 deg C in a double cone and dried in vacuo for 8 hours to give 2.30 kg of S-MeCBS, Yield 83percent The product is a white solid, GC: 98.2percent, water content: 0.31percent

Reference： [1] Patent: CN106478703, 2017, A, . Location in patent: Paragraph 0015; 0016

3
[ 22348-32-9 ]
[ 823-96-1 ]
[ 112022-81-8 ]

Reference： [1] Organic Letters, 2003, vol. 5, # 23, p. 4249 - 4251
[2] Patent: US6049009, 2000, A,
[3] Journal of the American Chemical Society, 2008, vol. 130, # 48, p. 16295 - 16309
[4] Tetrahedron, 2009, vol. 65, # 46, p. 9583 - 9591
[5] Patent: WO2004/4722, 2004, A1, . Location in patent: Page/Page column 58-59
[6] Chemical Communications, 2010, vol. 46, # 45, p. 8624 - 8626
[7] Organic Letters, 2014, vol. 16, # 14, p. 3780 - 3783
[8] Journal of Organic Chemistry, 2015, vol. 80, # 22, p. 11468 - 11479

4
[ 22348-32-9 ]
[ 112022-81-8 ]

Reference： [1] Journal of the American Chemical Society, 1987, vol. 109, # 25, p. 7925 - 7926
[2] Journal of the American Chemical Society, 1987, vol. 109, # 25, p. 7925 - 7926

5
[ 22348-32-9 ]
[ 13061-96-6 ]
[ 112022-81-8 ]

Reference： [1] Helvetica Chimica Acta, 2001, vol. 84, # 2, p. 431 - 472
[2] Synthesis, 2003, # 12, p. 1851 - 1855
[3] Journal of the Chemical Society. Perkin Transactions 2, 2000, # 1, p. 69 - 76
[4] Angewandte Chemie, International Edition, 1998, vol. 37, p. 1987 - 2014[5] Angewandte Chemie, 1998, vol. 110, p. 2092 - 2118
[6] Chemical Communications, 2010, vol. 46, # 45, p. 8624 - 8626
[7] Organic Letters, 2017, vol. 19, # 16, p. 4355 - 4358

6
[ 86595-28-0 ]
[ 112022-81-8 ]
[ 71-36-3 ]

Reference： [1] Patent: WO2006/134074, 2006, A2, . Location in patent: Page/Page column 10

7
[ 151293-60-6 ]
[ 22348-32-9 ]
[ 112022-81-8 ]

Reference： [1] Journal of Organometallic Chemistry, 1993, vol. 455, # 1-2, p. 37 - 46

[ 112022-81-8 ] Synthesis Path-Downstream 1~30

1
[ 22348-32-9 ]
[ 13061-96-6 ]
[ 112022-81-8 ]

Reference： [1]Helvetica Chimica Acta,2001,vol. 84,p. 431 - 472
[2]Synthesis,2003,p. 1851 - 1855
[3]Journal of the Chemical Society. Perkin Transactions 2 (2001),2000,p. 69 - 76
[4]Angewandte Chemie - International Edition,1998,vol. 37,p. 1987 - 2014
Angew. Chem., Int. Ed.,1998,vol. 110,p. 2092 - 2118
[5]Chemical Communications,2010,vol. 46,p. 8624 - 8626
[6]Organic Letters,2017,vol. 19,p. 4355 - 4358

2
[ 22348-32-9 ]
[ 823-96-1 ]
[ 112022-81-8 ]

Yield	Reaction Conditions	Operation in experiment
	In toluene;	Preparation Example 1 Preparation of (S)-3,3-diphenyl-1-methyltetrahydro-1H,3H-pyrrolo[1,2-c]1,3,2 oxazaborol Under argon stream, to a solution of (S)-alpha,alpha-diphenyl-2-pyrrolidine methanol (3 g, 11.8 mmol) in dry toluene (90 ml) was added trimethyl boroxine (1.13 ml, 8.0 mmol), followed by stirring for 1.5 hours. After the argon stream was stopped and the toluene (22.5 ml) was recovered under normal pressures on an oil bath at 140 C., dry toluene (22.5 ml) was added. Furthermore, after this recovery operation was repeated twice, the resultant product was concentrated under normal pressures, and subsequently under a reduced pressure, to thereby obtain the titled compound as a colorless crystalline. Yield: 3.28 g (yield 100%); NMR(delta ppm): 0.36 (3H, s, methyl at 1-position), 0.77-0.86 (1H, m, 1 proton of methylene at 4-position), 1.55-1.79 (3H, m, 1 proton of methylene at 4-position, methylene at 5-position), 3.02-3.07 (1H, m, 1 proton of methylene at 6-position), 3.32-3.37 (1H, m, 1 proton of methylene at 6-position), 4.35 (1H, dd, methine at 3a-position), 7.13-7.62 (10H, m, ArH)
		A flame-dried [50ML] one-necked flask was charged with 5.10 g (20.1 [MMOL,] 1.0 eq) of S-diphenylprolinol (32) and 56 mL of anhydrous [TOLUENE.] The solution was heated up to [140-150] [XB0;C.] 36 mL of dry toluene was azeotropically distilled through a Dean-Stark trap with an air condenser. Another 36 mL of toluene was added and the azeotropic distillation was repeated three times. After the third azeotropic distillation was done, another 36 mL of anhydrous toluene was added. The solution was allowed to cool to room temperature. Methylboroxin (1.90 mL, 13.5 mmol, 0.67 eq) was added via syringe over 5 min. A solid was formed after completion of the addition. The reaction mixture was stirred at room temperature for 30 min and 36 mL of toluene was distilled off. Another 36 mL of dry toluene was added and distilled off again. The distillation was repeated one more time, then 20 mL of 1.0 M of CBS catalyst (33) solution in toluene was prepared. The solution was used in CBS reduction directly.

Reference： [1]Organic Letters,2003,vol. 5,p. 4249 - 4251
[2]Patent: US6049009,2000,A
[3]Journal of the American Chemical Society,2008,vol. 130,p. 16295 - 16309
[4]Tetrahedron,2009,vol. 65,p. 9583 - 9591
[5]Patent: WO2004/4722,2004,A1 .Location in patent: Page/Page column 58-59
[6]Chemical Communications,2010,vol. 46,p. 8624 - 8626
[7]Organic Letters,2014,vol. 16,p. 3780 - 3783
[8]Journal of Organic Chemistry,2015,vol. 80,p. 11468 - 11479

3
[ 149915-80-0 ]
[ 112022-81-8 ]
[ 895534-20-0 ]

Yield	Reaction Conditions	Operation in experiment
98%		This step follows the general procedure of Salunkhe and Burkhardt, Tetrahedron Letters 38(9): 1523 (1997). A solution of 1.4 mL (1.4 mmole) l.OM S-2-methyl-CBS- oxazaborolidine in toluene and 2.8 mL (15.8 mmole) borane-diethylaniline complex in 15 mL toluene was heated at 3O0C under a dry nitrogen atmosphere. A solution of 3.5 g (13.8 mmole) 6-phenylsulfanyl-3,4-dihydro-2H-naphthalene-l-one in 15 mL toluene was added dropwise over 2 hours. The reaction mixture was stirred at 30-32C for one hour. Methanol (5.0 mL) was added dropwise over 20 minutes followed by 10 mL I. ON hydrochloric acid. The mixture was stirred for 20 minutes, then it was diluted with 50 mL ethyl ether. The organic phase was washed twice with 25 mL water, once with 20 mL EPO <DP n="93"/>saturated sodium chloride, dried (magnesium sulfate) and concentrated under reduced pressure. The residue was recrystallized from ether/hexane to give .R-6-rhohenylsulfanyl- 1,2,3,4-tetrahydro-naphthalen-l-ol, 3.49 g (98%), m.p. 74-75C. M+H= 256; [alpha]D = - 30.8 (c = 1, CHCl3). Chiral HPLC on a Chiracel OD (20 microns) eluting with 5% isopropyl alcohol in hexane, retention time = 10.9 min, 99.9 ee.

Reference： [1]Patent: WO2006/66790,2006,A1 .Location in patent: Page/Page column 90-92

4
[ 456-04-2 ]
[ 112022-81-8 ]
[ 18511-62-1 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; In tetrahydrofuran;	(1) 1.0 g of 2-Chloro-4'-fluoroacetophenone was dissolved in 5 ml of tetrahydrofuran, and 0.16 g of (S)-5,5-diphenyl-2-methyl-3,4-propano-1,3,2-oxazaborolidine and 1M borane-tetrahydrofuran complex 7.0 ml of tetrahydrofuran solution were added with ice-cooling, followed by stirring for 10 minutes. Then, to the reaction solution was added 2 ml of 4M aqueous sodium hydroxide solution, followed by stirring at room temperature for 4 hours. The reaction solution was concentrated under reduced pressure, and the residue was dissolved in ether and washed with a saturated aqueous sodium bicarbonate solution and a saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous sodium sulfate. After removal of the drying agent by filtration, the filtrate was concentrated under reduced pressure. The residue was purified by a silica gel column chromatography (Wako-gel C200, hexane:ethyl acetate=10:1) to give an optically active 2-(4-fluorophenyl)oxirane (0.85 g) as an oil.

Reference： [1]Patent: US2003/186992,2003,A1

5
aqueous potassium carbonate [ No CAS ]
[ 24424-99-5 ]
[ 112022-81-8 ]
[ 357405-01-7 ]

Yield	Reaction Conditions	Operation in experiment
928 mg (73%)	With hydrogenchloride; borane; In tetrahydrofuran; methanol; toluene;	b [3-Hydroxy-3-(3-pyridinyl)propyl]carbamic acid, 1,1-dimethylethyl ester Borane (3.0 ml, 1M in tetrahydrofuran) was added to a solution of (3aS)-tetrahydro-1-methyl-3,3-diphenyl-3H-pyrrolo[1,2-c][1,3,2]oxazaborole (0.22 ml, 1M in toluene) in tetrahydrofuran (5 ml) at 0 C. A solution of the product from step (a) (1.13 g, 4.52 mmol) in tetrahydrofuran (3 ml) was added over 30 minutes and then stirred at 20 C. for 24 h. Methanol was added and the solution was evaporated and methanol (15 ml) and 2M hydrochloric acid (5 ml) were added and stirred for 45 minutes. Aqueous potassium carbonate and di-tert-butyldicarbonate (250 mg) were added and the mixture was extracted with ethyl acetate (2) and dichloromethane (4). ) The organic extracts were dried (sodium sulphate), evaporated and purified by chromatography on silica eluding with dichloromethane-methanol to give 928 mg (73%) of the sub-title compound as a colourless oil. MS APCI+ve m/z 253 [(M+H)+].

Reference： [1]Patent: US2003/158185,2003,A1

6
[ 112022-81-8 ]
[ 38425-26-2 ]
[ 357443-51-7 ]

Yield	Reaction Conditions	Operation in experiment
	In tetrahydrofuran; methanol;	a R-alpha-(3-Chloropropyl)-4-methyl-benzenemethanol (S)-2-methyl-CBS-oxazaborolidine was dissolved in tetrahydrofuran (10 ml) and the solution cooled to 0 C. The stirred solution was treated with borane-tetrahydrofuran complex (1M in tetrahydrofuran) (3.4 ml, 3.4 mmol). A solution of 4-chloro-4'-methylbutyrophenone (1.1 g, 5.59 mmol) in tetrahydrofuran (40 ml) was added dropwise over 0.5 hours and the reaction allowed to warm to room temperature overnight. The reaction was quenched with methanol (3.4 ml) and then concentrated in vacuo. Methanol (3.5 ml) was added and the solution was re-concentrated. The residue was passed down a flash silica column, eluding with hexane:diethyl ether (4:1) to give product 18(a) as a colourless oil (1.03 g, 93%, 95% ee). 1H NMR 300 MHz (CDCl3) 7.20 (4H, dd), 4.71-4.65 (1H, m), 3.60-3.52 (2H, m), 2.35 (3H, s), 1.98-1.75 (5H, m).

Reference： [1]Patent: US2003/105161,2003,A1

7
borane-THF [ No CAS ]
[ 17694-68-7 ]
[ 112022-81-8 ]
[ 391906-07-3 ]

Yield	Reaction Conditions	Operation in experiment
34%	In tetrahydrofuran; methanol;	Step a) 3-[(2 S)-Oxiranyl]pyridine A solution of borane-THF (1 M solution, 15 mL) was added dropwise to a 0 C., stirred solution of (S)-2-methyl-CBS-oxazaborolidine monohydrate (0.738 g, 2.5 mmol) in THF (10 mL) over a period of 10 min. After stirred at 0 C. for 10 minutes the mixture was then added dropwise into a cold (0 C.) stirred suspension of 3-(2-bromoacetyl)pyridine hydrobromide (7.0 g, 24.9 mmol) in THF (50 mL) over a period of 10 minutes. After addition was completed the mixture was stirred at room temperature under a nitrogen atmosphere overnight. The reaction was cooled to 0 C. and quenched with dry HCI (0.5 M in methanol, 9 mL) The mixture was further diluted with water and extracted with ethyl acetate. The extract was washed with water and dried with MgSO4. Evaporation and purification by flash column chromatography (methylene chloride/methanol 95/5) gave (1 R)-2-bromo-1-(3-pyridinyl)-1-ethanol as a brown oil (1.72 g, 34%).
27%	In tetrahydrofuran; methanol;	EXAMPLE 129 3-[(2S)-Oxiranyl]pyridine A solution of borane-THF (1.0 M solution, 22.8 mL) was added dropwise into a cold (0 C.) solution of (S)-2-methyl-CBS-oxazaborolidine monohydrate (1.12 g, 3.8 mmol) in tetrahydrofuran (20 mL), over a period of 10 minutes. After stirring at 0 C. for 10 minutes, the mixture was added dropwise to a cold (0 C.) suspension of 3-(2-bromoacetyl)pyridine hydrobromide (10.6 g, 38.0 mmol) in tetrahydrofuran (70 mL) over a period of 10 minutes. After the addition the mixture was stirred at room temperature, under a nitrogen atmosphere, overnight. The reaction was cooled to 0 C. and quenched with hydrogen chloride (0.5 M in methanol, 9 mL). The mixture was further diluted with water and extracted with ethyl acetate. The extracts were washed with water and dried with MgSO4. Evaporation and purification by flash column chromatography (dichloromethane/methyl alcohol 95/5) gave (1R)-2-bromo-1-(3-pyridinyl)-1-ethanol as a brown oil (2.01 g, 27% yield).

Reference： [1]Patent: US2002/32222,2002,A1
[2]Patent: US2002/28835,2002,A1

8
{1-[4-(6-Methoxy-pyridin-3-yl)-2-oxo-but-3-enyl]-5(R)-methyl-2-oxo-pyrrolidin-3(S)-yl}-carbamic Acid Tert-butyl Ester [ No CAS ]
[ 13292-87-0 ]
[ 112022-81-8 ]
{1-[2(R)-Hydroxy-4-(6-methoxy-pyridin-3-yl)-but-3-enyl]-5(R)-methyl-2-oxo-pyrrolidin-3(S)-yl }-carbamic Acid Tert-butyl Ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In tetrahydrofuran; methanol; dichloromethane; toluene;	{1-[2(R)-Hydroxy-4-(6-methoxy-pyridin-3-yl)-but-3-enyl]-5(R)-methyl-2-oxo-pyrrolidin-3(S)-yl }-carbamic Acid Tert-butyl Ester (4-5) To a stirred solution of (S)-2-methyl-CBS-oxazaborolidine (4.47 mL, 1M in toluene) in dichloromethane (10 mL) was added a solution of borane-dimethylsulfide (0.45 mL, 10M) and the resulting solution was stirred at ambient temperature for 40 minutes. This solution was added to a stirred solution of 4-4 (580 mg, 1.49 mmol) in THF (15 mL) at -40 C. and the reaction mixture was stirred for 3 hours. Methanol (2 mL) was added and the reaction mixture was concentrated at reduced pressure. The residue was purified by flash column chromatography (silica gel, 2:1 ethyl acetate/hexanes) to give 4-5 as a colorless oil. 1H NMR (300 MHz, CDCl3) delta 8.11 (d, J=2.4 Hz, 1H), 7.65 (dd, J=2.4, 8.5 Hz, 1H), 6.72 (d, J=8.6 Hz, 1H), 6.65 (d, J=16.2 Hz, 1H), 6.08 (dd, J=16.2, 6.3 Hz, 1H), 5.12 (br s, 1H), 4.47 (m, 1H), 4.20 (m, 2H), 3.96 (s, 3H), 3.72 (m, 1H), 3.60 (m, 1H), 3.52 (dd, J=14.5, 3.2 Hz, 1H), 3.37 (dd, J=14.3, 8.8 Hz, 1H), 2.83 (m, 1H), 1.45 (s, 9H), 1.33 (d, J=6.2 Hz, 3H).

Reference： [1]Patent: US6413955,2002,B1

9
{1-[4-(2-methyl-pyrimidin-5-yl)-2-oxo-but-3-enyl]-5(R)-methyl-2-oxo-pyrrolidin-3(S)-yl}-carbamic Acid Tert-butyl Ester [ No CAS ]
[ 13292-87-0 ]
[ 112022-81-8 ]
{1-[2-Hydroxy-4-(2-methyl-pyrimidin-5-yl)-but-3-enyl]-5(R)-methyl-2-oxo-pyrrolidin-3(S)-yl}-carbamic Acid Tert-butyl Ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In tetrahydrofuran; methanol; dichloromethane; toluene;	{1-[2-Hydroxy-4-(2-methyl-pyrimidin-5-yl)-but-3-enyl]-5(R)-methyl-2-oxo-pyrrolidin-3(S)-yl}-carbamic Acid Tert-butyl Ester (5-2) To a stirred solution of (S)-2-methyl-CBS-oxazaborolidine (6.4 mL, 1M in toluene) in dichloromethane (15 mL) was added a solution of borane-dimethylsulfide (0.64 mL, 10M) and the resulting solution was stirred at ambient temperature for 40 minutes. This solution was added to a stirred solution of 5-1 (800 mg, 2.14 mmol) in THF (30 mL) at -40 C. and the reaction mixture was stirred for 3 hours. Methanol (5 mL) was added and the reaction mixture was concentrated at reduced pressure. The residue was purified by flash column chromatography (silica gel, 9:1 ethyl acetate/methanol) to give 5-2 as a colorless oil. 1H NMR (300 MHz, CDCl3) delta 8.63 (s, 2H), 6.68 (d, J=16 Hz, 1H), 6.30 (dd, J=16.1, 6.2 Hz, 1H), 5.12 (br s, 1H), 4.47 (m, 1H), 4.20 (m, 2H), 3.70 (m, 2H), 3.48 (dd, J=14.4, 3.3 Hz, 1H), 3.40 (dd, J=14.3, 8.6 Hz, 1H), 2.82 (m, 1H), 1.45 (s, 9H), 1.34 (d, J=6.1 Hz, 3H).

Reference： [1]Patent: US6413955,2002,B1

10
borane-THF [ No CAS ]
[ 2631-72-3 ]
[ 112022-81-8 ]
[ 187164-20-1 ]

Yield	Reaction Conditions	Operation in experiment
	In tetrahydrofuran; methanol;	1-(a). Preparation of (S)-1-(2,4-dichlorophenyl)-2-bromoethanol: STR11 To 5 ml of dry tetrahydrofuran (THF) was added 300 mg of (S)-3,3-diphenyl-1-methyltetrahydro-1H,3H-pyrrolo-[1,2-c][1,3,2]oxazaborole, and then thereto was added dropwise 8 ml of 1.0M borane-THF solution at -20 C. At the same temperature, thereto was further added dropwise a solution of 2.7 g of 2.4-dichlorophenacyl bromide in 8 ml of THF. The resultant mixture was heated to room temperature, and then stirred for 3 hours. Next, 10 ml of methanol was added to decompose excess borane, and then the reaction mixture was poured into water and extracted with ether. The organic layer was washed with water and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and the residue was purified by silica gel column chromatography (ethyl acetate/n-hexane=1/3) to obtain 2.5 g of the desired product at an optical purity of 80% ee.

Reference： [1]Patent: US5900488,1999,A

11
BH_3.S(CH₃)2 [ No CAS ]
(S)-oxazaborolidine [ No CAS ]
[ 60-29-7 ]
[ 25564-22-1 ]
[ 112022-81-8 ]
(+)-(1R)-2-pentyl-1-cyclopenten-1-ol [ No CAS ]
[ 202530-97-0 ]

Yield	Reaction Conditions	Operation in experiment
89%	With hydrogenchloride; In tetrahydrofuran; methanol; toluene;	EXAMPLE 1 Preparation of (+)-(1R)-2-pentyl-1-cyclopenten-1-ol A solution of 2-pentyl-2-cyclopenten-1-one (9.12 g, 60 mmole) in 140 ml of tetrahydrofurane (THF) was treated with an oxazaborolidine represented above, namely <strong>[112022-81-8](S)-tetrahydro-1-methyl-3,3-diphenyl-1H,3H-pyrrolo[1,2-c][1,3,2]oxazaborole</strong> (16.7 ml; 0.36 M in toluene, 6.0 mmole; see D. J. Mathre, ref. cited). A solution of BH3.S(CH3)2 (3.30 ml=2.64 g, 34.8 mmole) in THF (60 ml) was added dropwise at 0 over 1 h. The reaction was stopped with 3 ml of methanol (development of H2), followed by ethyl ether and 5% HCl. The organic phase, which had been washed to neutrality (2* with water and 1* with brine), was separated and the solvent evaporated. 9.5 g of a crude product were obtained, which was distilled in a bulb-to-bulb apparatus (oven temp. 60/11 Pa), to give 8.1 g of (+)-(1R)-2-pentyl-2-cyclopenten-1-ol (yield 89%). The compound showed the following analytical data. [alpha]20D =+28.3 (c=2.7; CHCl3) enantiomeric excess (e.e.)=91% (measured on a chiral column of type Megadex5 or CD-Chirasil DEX CB on the basis of the corresponding trimethylsilyl ether) NMR(1 H, 360 MHz): 0.89(t, J=7, 3H); 1.20-1.40(m, 4H); 1.40-1.57(m, 3H; with D2 O=2H); 1.69(m, 1H); 2.02-2.47(m, 5H); 4.64(broad, 1H); 5.53(broad s, 1H) delta ppm. NMR(13 C): 146.7(s); 126.9(s); 78.9(d); 34.1(t); 31.9(t); 29.7(t); 28.1(t); 27.5(t); 22.6(t); 14.1(q) delta ppm. MS: 154(M+, 2), 97(30), 83(100), 79(12), 67(7), 55(11), 41(9).

Reference： [1]Patent: US5962706,1999,A

12
[ 112022-81-8 ]
[ 191591-86-3 ]
(+)-5-[3-[4-(4-fluorophenyl)piperazin-1-yl]propyl]-8-hydroxy-1-methyl-1,4,5,6,7,8-hexahydropyrrolo[3,2-c]azepin-4-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In toluene;	EXAMPLE 86 Synthesis of (+)-(R) -5-[3-[4-(4-fluorophenyl)piperazin-1-yl]propyl]-8-hydroxy-1-methyl-1,4,5,6,7,8-hexahydropyrrolo[3,2-c]azepin-4-one (Compound No. 84) by asymmetric reduction of Compound No. 33 with (S)-3,3-diphenyl-1-methyltetrahydro-1H,3H-pyrrolo[1,2-c] [l,3,2]oxazaborol Using 398 mg (1.0 mmol) of Compound No. 33, 250 mg of molcular sieves 4A (powder), 56 mg (0.2 mmol) of <strong>[112022-81-8](S)-3,3-diphenyl-1-methyltetrahydro-1H,3H-pyrrolo[1,2-c][1,3,2]oxazaborol</strong>, 4.1/ml (4.5 mmol) of a 1.10M toluene solution of borane-dimethyl sulfide complex and 5.4 ml of toluene, 90 mg of the title compound were obtained in a similar manner as in Example 83 ?optical purity: 98.6% e.e. (by HPLC[analysis)]. Melting point: 167.5-168.5 C.

Reference： [1]Patent: US5962448,1999,A

13
[ 33944-98-8 ]
[ 112022-81-8 ]
(R,E)-4-phenylthio-3-buten-2-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Example 1 Preparation of (R,E)-4-phenylthio-3-buten-2-ol (E)-4-phenylthio-3-buten-2-one (178 mg, 1.0 mmol), (S)-3,3-diphenyl-1-methyltetrahydro-1H,3H-pyrrolo[1,2-c] [1,3,2] oxazaborol (28 mg, 0.1 mmol) and MS4A (Nacalai Tesque Inc., 500 mg) were dried by a vacuum pump, followed by substituting with an argon gas. Dry toluene (5 ml) and dimethylsulfide (3.0 mmol) were added thereto and, after ice cooling, a solution of borane dimethylsulfide complex in toluene (1.07M, 0.65 ml, 0.7 mmol) was dropwise added. After stirring for two hours, an aqueous saturated ammonium chloride solution was added, followed by filtering through a cotton plug. The filtrate was washed with ethyl acetate and, after separating an aqueous layer, the organic layer was washed with 2NHCl, water, an aqueous saturated sodium hydrogen carbonate solution, water and saturated brine. After drying with anhydrous magnesium sulfate, the extract containing the titled compound as a main component was obtained by concentrating under a reduced pressure. The NMR chemical shifts of the titled compound are as follows. NMR(delta ppm): 1.31 (3H, d, methyl at 1-position), 1.51 (1H, brs, OH), 4.40 (1H, m, methine at 2-position), 5.89 (1H, dd, olefin at 3-position), 6.42 (1H, d, olefin at 4-position), 7.23-7.38 (5H, m, ArH)

Reference： [1]Patent: US6049009,2000,A

14
[ 655-32-3 ]
[ 112022-81-8 ]
[ 17556-41-1 ]

Yield	Reaction Conditions	Operation in experiment
	With benzo[1,3,2]dioxaborole; In dichloromethane; at -78℃;	Catecholborane (19.4 mL, 182 mmol) in dichloromethane 15 mL) was added to a dichloromethane solution of 5-methyl CBS oxazaborolidine (13 mL, 13 mmol) and 2,2,2,4'- tetrafluoroacetopheone (18.2 mL, 130.13mmol) dropwise at -78 C in 30 min and stirred at - 78 C overnight. The reaction mixture was quenched by addition of 4N HCl in dioxane (13 mL) at -78 C, warmed up to room temperature and the solvent was removed under reduced pressure. 10% NaHSO3 solution (200 mL) was added and the aqueous layer was extracted with hexane. The organic layer was washed with water and dried with MgSO4. The solvent was removed under reduced pressure to give 2,2,2-trifluoro-1-(4-fluorophenyl)ethanol (20 g) as colorless oil (90% d.e.).

Reference： [1]Patent: WO2006/102535,2006,A2 .Location in patent: Page/Page column 68

Yield	Reaction Conditions	Operation in experiment
		A. N-Benzyl-cis-2-azabicyclo[3.3.0]octan-8-one (9) The commerically available 2-cyclopentene-1-acetic acid was treated with oxalyl chloride in CH2 Cl2. The reaction was catalyzed with a drop of DMF; and stirring for 2 h afforded a quantitative yield of 3 as a light brown oil.

16
C₂₂H₃₀BNO₂ [ No CAS ]
[ 86595-28-0 ]
[ 112022-81-8 ]
[ 71-36-3 ]

Yield	Reaction Conditions	Operation in experiment
	In toluene; for 4h;Heating / reflux;	Synthesis of (S)-MeCBS from Methyldi-n-butoxyborane(S)-Diphenylprolinol (DPP) (0.58g, 2.3 mmol) along with 15 ml of toluene were added to a 50 ml three-neck round bottom flask fitted with a distillation head and condenser and flushed with nitrogen. While remaining under inert atmosphere, methyldi-n-butoxyborane (0.60 g, 2.3 mmol) was added via syringe to the flask. The reaction contents were heated to 1100C while stirring for 1 hour. While the 11B NMR spectrum of the reaction mixture showed the formation of intermediates delta = 9.7 ppm), additional methyldi-n-butoxyborane (0.06 g, 0.23 mmol) was added followed by heating for 4 hours. All toluene and 1-butanol were distilled from the clear reaction mixture (azeotrope boiling point 1060C). Toluene was added to the residue. The 11B NMR spectrum of the toluene solution showed complete formation of (S)-MeCBS (delta = 35 ppm, broad singlet). The 1H NMR spectrum (CDCb) of the product also indicated no remaining (S)-DPP or unreacted methyldi-n- butoxyborane.

Reference： [1]Patent: WO2006/134074,2006,A2 .Location in patent: Page/Page column 10

17
[ 22348-32-9 ]
methylboronic acid [ No CAS ]
[ 112022-81-8 ]

Reference： [1]Journal of the American Chemical Society,1987,vol. 109,p. 7925 - 7926
[2]Journal of the American Chemical Society,1987,vol. 109,p. 7925 - 7926

18
[ 13283-31-3 ]
[ 112022-81-8 ]
[ 461412-21-5 ]

Reference： [1]Journal of the American Chemical Society,1987,vol. 109,p. 7925 - 7926

19
[ 151293-60-6 ]
[ 22348-32-9 ]
[ 112022-81-8 ]

Reference： [1]Journal of Organometallic Chemistry,1993,vol. 455,p. 37 - 46

20
[ 160539-64-0 ]
[ 112022-81-8 ]
Sn(C₄H₉)3(CH₃)2C₃H₂(OH) [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1995,vol. 117,p. 558 - 559

21
[ 112022-81-8 ]
[ 302912-29-4 ]
[ 945978-45-0 ]

Yield	Reaction Conditions	Operation in experiment
96%	With hydrogenchloride; In tetrahydrofuran; toluene;	6.26. Synthesis of (S)-2-Amino-3-(4-(4-amino-6-((R)-1-(biphenyl-2-yl)-2,2,2-trifluoroethoxy)-1,3,5-triazin-2-yl)phenyl)propanoic acid A mixture of 1-biphenyl-2-yl-2,2,2-trifluoro-ethanone (300 mg, 1.2 mmol), borane tetrahydrofuran complexes (1.2 ml, 1M in THF, 1.2 mmol) and S-2-methyl-CBS-oxazaborolidine (0.24 ml, 1M in toluene, 0.24 mmol) in THF (8 ml) was stirred at room temperature over night. Several drops of concentrated HCl were added and the mixture was stirred for 30 minutes. The product was purified by SiO2 chromatography (hexane/ethyl acetate=100/0 to 3/1) to give 290 mg of 1-biphenyl-2-yl-2,2,2-trifluoro-ethanol (96% yield).
96%	With hydrogenchloride; In tetrahydrofuran; toluene;	6.24. Synthesis of (S)-2-Amino-3-(4-(4-amino-6-((R)-1-(biphenyl-2-yl)-2,2,2-trifluoroethoxy)-1,3,5-triazin-2-yl)phenyl)propanoic acid A mixture of 1-biphenyl-2-yl-2,2,2-trifluoro-ethanone (300 mg, 1.2 mmol), borane tetrahydrofuran complexes (1.2 ml, 1M in THF, 1.2 mmol) and S-2-methyl-CBS-oxazaborolidine (0.24 ml, 1M in toluene, 0.24 mmol) in THF (8 ml) was stirred at room temperature over night. Several drops of concentrated HCl were added and the mixture was stirred for 30 minutes. The product was purified by SiO2 chromatography (hexane/ethyl acetate=100/0 to 3/1) to give 290 mg of 1-biphenyl-2-yl-2,2,2-trifluoro-ethanol (96% yield).

Reference： [1]Patent: US2009/5381,2009,A1
[2]Patent: US2009/29993,2009,A1

22
[ 13292-87-0 ]
[ 112022-81-8 ]
(3aS)-1-methyl-3, 3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole borane complex [ No CAS ]

Reference： [1]Organometallics,2008,vol. 27,p. 2179 - 2188

23
[ 768400-09-5 ]
[ 768400-08-4 ]
[ 112022-81-8 ]
isopropyl 7-{(4R)-4-[(1E)-4,4-difluoro-3-hydroxy-4-phenylbut-1-en-yl]-2-oxo-1,3-oxanzinan-3-yl}heptanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		To a solution of catecholborane (107 mg) in toluene (1 mL) was added (S)-2-methyl-CBS-oxaborolidine (1M in toluene, 0.89 mL) under N2 at -78 C. and the mixture was stirred at the temperature for 1 h. Isopropyl 7-{(4R)-4-[(1E)-4,4-difluoro-3-oxo-4-phenylbut-1-en-1-yl]-2-oxo-1,3-oxazinan-3-yl}heptanoate (200 mg) in toluene (2 mL) was added via a cannula slowly and the mixture was stirred for an additional hour and quenched with 1N HCl. The mixture was allowed to warm to room temperature and extracted with DCM (2*). The organic layers were dried over Na2SO4 and filtered. The filtrate was concentrated in vacuo and the residue purified by column chromatography (80-100% ethyl acetate/hexanes) to give the title compound. MS (+ESI): m/z 454 (M+1)+.

Reference： [1]Patent: US2004/198701,2004,A1 .Location in patent: Page/Page column 22

24
[ 112022-81-8 ]
(S)-methyloxazaborolidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With dimethylsulfide borane complex; In toluene; at 20℃; for 0.5h;	S)-Methyl CBS-borane Reagent (2)A 250 mL, 2 neck Schlenk flask was equipped with a magnetic stirbar, a N2 inlet, and charged with 75 mL of (S)-methyloxazaborolidine 1 in toluene (1.0 M) at 20 C. Approximately half the volume of toluene was evaporated under vacuum with mild warming to yield about 40 mL of 2 M oxazaborolidine. Borane-dimethyl sulfide complex (10 mL, 10 M, neat) was added in one portion with rapid stirring and the resulting solution was stirred for 30 min at 20 C. Pentane (200 mL) was then added via cannula to precipitate the product (after 15 min of stirring), followed by filtration under N2 and the solids were washed with 2 additional 200 mL portions of pentane. The solids were dried under a stream of nitrogen to a constant weight, affording 19.4 g (88% yield) of borane complex 2 as a white solid. The purity was estimated >90% by NMR analysis 1H NMR (CDCl3): 0.73 (s, 3H), 1.29 (m, 2H), 1.57 (m, 2H), 1.90 (m, 2H), 3.18 (dt, 1H), 3.37 (m, 1H), 4.61 (t, 1H), 7.2-7.6 (m, 10H).

Reference： [1]Patent: US2009/143461,2009,A1 .Location in patent: Page/Page column 9-10

25
[ 552885-75-3 ]
[ 112022-81-8 ]
C₁₄H₁₃FO [ No CAS ]
C₁₄H₁₃FO [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		To a dried round bottom flask was charged with commercial available (S)-2-methyl-CBS-oxazaborolidine (1.0 mL, 1M in THF, 1.0 mmol) and 5.0 mL of dryTHF under N2atmosphere. After cooling to -30C, 1M BH3THF (12.0 mL, 12.0 mmol) in THF was added andthe mixture stirred at the same temperature for 30 minutes. A solution of mt 4-1 (2.1 g, 1.0 5 mmol) in dry THF (20.0 mL) was added into the mixture over an hour at -3 0C. The reactionwas followed by TLC (PE :EA = 15:1) until completion. The resulting mixture was allowed to warm up to 0C and quenched by the addition of 5 mL of methanol. The mixture was then concentrated and the residue was purified via silica gel chromatography (PE: EA = 20:1) to provide the desired alcohol mt 4-2 (1.8 g, 86%, e.e.: 85%).

Reference： [1]Patent: WO2014/197345,2014,A2 .Location in patent: Page/Page column 61; 62

26
[ 13061-96-6 ]
[ 22348-32-9 ]
[ 112022-81-8 ]

Yield	Reaction Conditions	Operation in experiment
83%	In n-heptane; at 40℃;Inert atmosphere; Reflux; Large scale;	Under nitrogen protection, In a reactor equipped with a reflux water separation device(S)-(+)-2-(diphenylhydroxymethyl)pyrrolidine (2.53 kg, 10 moles) and methylboronic acid (779 g, 13 moles) were added to 7.1 g of n-heptane, Slowly stirring, As the water is constantly being separated, The solution gradually becomes clear, Then adjust the stirring speed to the normal state, When there is no more water, Stop stirring, Slow down to 40 deg C, After standing overnight, Diatomaceous earth temperature filtration, The filtrate was once again cooled to -10 C, Stirring for 1.5 hours to complete precipitation, After filtration, 40 deg C in a double cone and dried in vacuo for 8 hours to give 2.30 kg of S-MeCBS, Yield 83% The product is a white solid, GC: 98.2%, water content: 0.31%

Reference： [1]Patent: CN106478703,2017,A .Location in patent: Paragraph 0015; 0016

27
[ 112022-81-8 ]
[ 22348-32-9 ]

Reference： [1]Organic Syntheses,2002,vol. 79,p. 72 - 72

28
C₂₀H₁₆O₇ [ No CAS ]
[ 112022-81-8 ]
C₂₀H₁₈O₇ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%		A solution of S-(-)-2-methyl-CBS-oxazaborolidine (1Msolution in toluene, 4.9 mmol) inTHF (5 mL) was treated with BH3.DMS (2.0 M solution in THF) (0.2 mL, 04.1 mmol) at 0oC for15 min. A solution of enone 3 (0.150 g, 4.1 mmol) in THF (8 mL) was added slowly at -78 C The reaction mixture was stirred for 1 h maintaining the temperature. After completion ofreaction, saturated NH4Cl solution was added. The aqueous layer was extracted with ethylacetate, the combined organic layer was washed with brine and dried over anhydrous Na2SO4and concentrated under reduced pressure. The residue was purified by flash chromatographywith 10% EtOAc/hexane gave compound 18 (0.128 g, 85%, ee 98%) as colourless liquid. [alpha]D25 -2.53 (c 4.8, CHCl3). IR (KBr): numax= 3562,2972, 2920, 2847, 1586, 1448, 1227, 1107, 720 cm-1. 1H NMR(300 MHz, CDCl3): delta = 6.73 (s, 1 H), 6.33 (s, 1 H), 5.93-5.84 (m, 5H), 5.77-5.70 (m, 1 H), 4.88-4.82 (m, 1 H), 3.85 (s, 3 H), 3.83 (s,3 H), 2.93-2.86 (m, 1 H), 2.76-2.70 (m, 1 H). 13C NMR (75 MHz,CDCl3): delta = 149.7, 149.4, 140.0, 139.6, 135.5, 135.4, 134.8, 134.7,130.0, 129.2, 121.1, 119.9, 103.5, 101.1, 100.9, 98.8, 68.9, 59.4 (2C), 31.9 ppm. HRMS: m/z calcd for C20H20O7: 371.1052;371.1048 [M + H]+

Reference： [1]Synlett,2018,vol. 29,p. 908 - 911

29
[ 121-89-1 ]
[ 112022-81-8 ]
[ 76116-24-0 ]

Yield	Reaction Conditions	Operation in experiment
74%	Stage #1: (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole With borane Ν,Ν-diethylaniline complex In toluene at 30℃; for 0.333333h; Inert atmosphere; Stage #2: 3-Nitroacetophenone In toluene at 30℃; for 5.5h;	D.1 Step 1: (i?)-l-(3-nitrophenyl)ethanol. To a solution of (

Reference： [1]Current Patent Assignee: NURIX THERAPEUTICS INC; NELIKUS TREAT - WO2021/21761, 2021, A1 Location in patent: Paragraph 0371

30
[ 2142-63-4 ]
[ 112022-81-8 ]
[ 134615-24-0 ]

Yield	Reaction Conditions	Operation in experiment
54%	With dimethyl sulfide borane In tetrahydrofuran; toluene at 30℃; for 7h;	55.1 Step 1: (/?)- -(3-bromophenyl) ethanol. To a solution of l-(3-bromophenyl)ethan-l- one (20.0 g, 100 mmol) and fS')-3.3-Di phenyl- 1 -methyl pyrrol idi no 1 1 2-c\|- 1 3.2-oxazaborole (10 mL, 10 mmol, 1 M in toluene) in toluene (200 mL) was added BH3 Me2S (10 mL, 100 mmol, 10 M in THF) dropwise at 30 °C. The mixture was stirred at 30 °C for 7 h, and then quenched by the addition of H2O. General Workup Procedure followed by Chromatography A afforded the title compound (11.0 g, 54%). MS (ESI) calc’d for (CsHgBrO) [M+H]+, 201.0; found, 201.0.

Reference： [1]Current Patent Assignee: NURIX THERAPEUTICS INC; NELIKUS TREAT - WO2021/21761, 2021, A1 Location in patent: Paragraph 0505

Same Skeleton Products

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Historical Records

Similar Product of
[ 112022-81-8 ]

A855211[ 112022-83-0 ]

(R)-1-Methyl-3,3-diphenylhexahydropyrrolo[1,2-c][1,3,2]oxazaborole

Reason: Optical isomers

Ghs Precautionary Statements

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Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
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Physical hazards
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H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
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H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
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H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
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H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 112022-81-8 ] {[proInfo.proName]}

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