[ CAS No. 148430-81-3 ] {[proInfo.proName]}

Name: 148430-81-3|Oxetan-3-yl methanesulfonate|95%
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Quality Control of [ 148430-81-3 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 148430-81-3 ]

Product Details of [ 148430-81-3 ]

CAS No. :	148430-81-3	MDL No. :	MFCD18207677
Formula :	C₄H₈O₄S	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	ZLYYZGDBMXPXOA-UHFFFAOYSA-N
M.W :	152.17	Pubchem ID :	21755243
Synonyms :

Calculated chemistry of [ 148430-81-3 ]

Physicochemical Properties

Num. heavy atoms :	9
Num. arom. heavy atoms :	0
Fraction Csp3 :	1.0
Num. rotatable bonds :	2
Num. H-bond acceptors :	4.0
Num. H-bond donors :	0.0
Molar Refractivity :	30.36
TPSA :	60.98 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-7.7 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.33
Log Po/w (XLOGP3) :	-0.66
Log Po/w (WLOGP) :	0.44
Log Po/w (MLOGP) :	-0.93
Log Po/w (SILICOS-IT) :	-0.18
Consensus Log Po/w :	0.0

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	2.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-0.24
Solubility :	88.4 mg/ml ; 0.581 mol/l
Class :	Very soluble
Log S (Ali) :	-0.15
Solubility :	108.0 mg/ml ; 0.713 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-0.26
Solubility :	84.4 mg/ml ; 0.555 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.66

Safety of [ 148430-81-3 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 148430-81-3 ]

* 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 [ 148430-81-3 ]
Downstream synthetic route of [ 148430-81-3 ]

[ 148430-81-3 ] Synthesis Path-Upstream 1~1

1
[ 7748-36-9 ]
[ 124-63-0 ]
[ 148430-81-3 ]

Yield	Reaction Conditions	Operation in experiment
100%	With triethylamine In dichloromethane at 0 - 20℃; for 3 h;	To a solution of oxetan-3-ol (5 g, 67.5 mmol) and triethylamine (14.11 mL, 101 mmol) in DCM (150 mL) at 0°C was added methanesulfonyl chloride (6.79 mL, 88 mmol) dropwise. The mixture was stirred at RT for 3 hr. The solid was filtered off and the filtrate was washed with ice -water and brine solution. The organic phase was dried over anhydrous Na₂S0₄ and concentrated in vacuo to afford the title compound (11.7 g, 67.5 mmol, 100percent yield) as an oil (containing 12.2 wtpercent of DCM). ^lU NMR (400 MHz, CDC1₃) δ 3.06 (s, 3H), 4.79-4.82 (m, 2H), 4.86-4.90 (m, 2H), 5.52-5.49 (m, 1H).
75.7%	Stage #1: With triethylamine In dichloromethane at 0℃; for 0.333333 h; Stage #2: at 20℃; for 12 h;	The oxetan-3-ol 16a (10.0 g, 135.0 mmol) was dissolved in dichloromethane (300 mL) at room temperature,After cooling to 0 ° C, triethylamine (20.4 g, 202.0 mmol) was added and stirred for 20 minutes.Methylsulfonyl chloride (20.08 g, 176.0 mmol) was added dropwise to the reaction solution and allowed to react at room temperature for 12 hours.The reaction solution was filtered and the filter cake was washed with dichloromethane (100 mL x 2), the organic phases were combined,Washed successively with water (200 mL x 1), saturated brine aqueous solution (200 mL x 1).Dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated under reduced pressure to give pale yellow solid 16b (15.6 g, yield 75.7percent).
1.2 g	With triethylamine In dichloromethane at 20℃; for 2 h; Cooling with ice	To an ice-water cooled solution of oxetan-3-ol (1.0 g) in DCM (50 mL) was added TEA (3.8 mL). MsCI (1 .6 mL) was then added dropwise. The resulting mixture was warmed up slowly and stirred at RT for 2 hours. The mixture was then quenched with aq. NaHCO3 solutionand extracted with EA (3x50 mL). The combined organic phases were washed, dried and concentrated to afford oxetan-3-yl methanesulfonate (1.2 g).

Reference： [1] Patent: WO2013/55910, 2013, A1, . Location in patent: Page/Page column 124; 125
[2] Patent: TW2017/8221, 2017, A, . Location in patent: Page/Page column 98; 99
[3] Patent: WO2015/181186, 2015, A1, . Location in patent: Page/Page column 169
[4] Journal of Medicinal Chemistry, 2017, vol. 60, # 23, p. 9769 - 9789
[5] Journal of Medicinal Chemistry, 2018, vol. 61, # 6, p. 2518 - 2532

[ 148430-81-3 ] Synthesis Path-Downstream 1~9

Yield	Reaction Conditions	Operation in experiment
89%		Example H1 Preparation of 3-oxetanyl mesylate: 25.2 ml of methane sulfochloride are added dropwise with stirring at 0C to a solution of 27 g of 3-oxetanol (89%) prepared by the method described in J. Org. Chem 48 , 2953 (1983) and 45.2 ml of triethylamine in 800 ml of methylene chloride.

2
[ 7748-36-9 ]
[ 124-63-0 ]
[ 148430-81-3 ]

Yield	Reaction Conditions	Operation in experiment
100%	With triethylamine; In dichloromethane; at 0 - 20℃; for 3h;	To a solution of oxetan-3-ol (5 g, 67.5 mmol) and triethylamine (14.11 mL, 101 mmol) in DCM (150 mL) at 0C was added methanesulfonyl chloride (6.79 mL, 88 mmol) dropwise. The mixture was stirred at RT for 3 hr. The solid was filtered off and the filtrate was washed with ice -water and brine solution. The organic phase was dried over anhydrous Na2S04 and concentrated in vacuo to afford the title compound (11.7 g, 67.5 mmol, 100% yield) as an oil (containing 12.2 wt% of DCM). lU NMR (400 MHz, CDC13) delta 3.06 (s, 3H), 4.79-4.82 (m, 2H), 4.86-4.90 (m, 2H), 5.52-5.49 (m, 1H).
75.7%		The oxetan-3-ol 16a (10.0 g, 135.0 mmol) was dissolved in dichloromethane (300 mL) at room temperature,After cooling to 0 C, triethylamine (20.4 g, 202.0 mmol) was added and stirred for 20 minutes.Methylsulfonyl chloride (20.08 g, 176.0 mmol) was added dropwise to the reaction solution and allowed to react at room temperature for 12 hours.The reaction solution was filtered and the filter cake was washed with dichloromethane (100 mL x 2), the organic phases were combined,Washed successively with water (200 mL x 1), saturated brine aqueous solution (200 mL x 1).Dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated under reduced pressure to give pale yellow solid 16b (15.6 g, yield 75.7%).
1.2 g	With triethylamine; In dichloromethane; at 20℃; for 2h;Cooling with ice;	To an ice-water cooled solution of oxetan-3-ol (1.0 g) in DCM (50 mL) was added TEA (3.8 mL). MsCI (1 .6 mL) was then added dropwise. The resulting mixture was warmed up slowly and stirred at RT for 2 hours. The mixture was then quenched with aq. NaHCO3 solutionand extracted with EA (3x50 mL). The combined organic phases were washed, dried and concentrated to afford oxetan-3-yl methanesulfonate (1.2 g).

Reference： [1]Patent: WO2013/55910,2013,A1 .Location in patent: Page/Page column 124; 125
[2]Patent: TW2017/8221,2017,A .Location in patent: Page/Page column 98; 99
[3]Patent: WO2015/181186,2015,A1 .Location in patent: Page/Page column 169
[4]Journal of Medicinal Chemistry,2017,vol. 60,p. 9769 - 9789
[5]Journal of Medicinal Chemistry,2018,vol. 61,p. 2518 - 2532

3
[ 148430-81-3 ]
[ 507-09-5 ]
[ 1402428-24-3 ]

Yield	Reaction Conditions	Operation in experiment
18.58%	With caesium carbonate; In N,N-dimethyl-formamide; at 60℃; for 19.5h;	To a solution of <strong>[148430-81-3]oxetan-3-yl methanesulfonate</strong> (9.43 g, 62.0 mmol) and ethanethioic S- acid (6.55 mL, 93 mmol) in DMF (100 mL) was added cesium carbonate (30.3 g, 93 mmol). The mixture was heated at 60C for 19.5 hr. The mixture was quenched with water and extracted with EtOAc. The organic layer was concentrated in vacuo (bath 25 C / 150 mmHg). The residue was distilled under vacuum (bp 45 C/ 10 mmHg). The product had DMF and thus the product was dissolved in ether and washed with water. The organic layer was dried over anhydrous MgS04, filtered, and concentrated in vacuo (bath 25 C / 150 mmHg) to afford the title compound (4.17 g, 11.51 mmol, 18.58% yield) as a light yellow oil (containing solvents such as DMF, EtOAc, and Et20). lU NMR (400 MHz, CDC13) delta 2.32 (s, 3H), 4.56-4.59 (m, 2H), 4.62-4.69 (m, 1H), 5.03-5.06 (m, 2H).

Reference： [1]Patent: WO2013/55910,2013,A1 .Location in patent: Page/Page column 125

4
[ 148430-81-3 ]
[ 1431874-22-4 ]
[ 1431873-42-5 ]
[ 1431873-44-7 ]

Yield	Reaction Conditions	Operation in experiment
21%; 1%	With caesium carbonate; In N,N-dimethyl-formamide; at 100℃; for 6h;Sealed tube;	Intermediate 26 (2.08 g, 4.68 mmol), Oxetan-3-yl methanesulfonate (CAS: 148430-81-3) (1.14 g; 7.49 mmol) and cesium carbonate (2.29 g; 7.02 mmol) in DMF (35 mL) were stirred in a sealed tube at 100C for 6 hours. The mixture was poured into ice and extracted with EtOAc. The organic layer was washed with brine, dried over MgS04, filtered evaporated to dryness. The crude product was purified by chromatography over silica gel (5g of dry loading irregular SiOH 70-200muetaeta, irregular SiOH, 15-45pm, 25g; mobile phase : gradient from 98% DCM, 2% MeOH to 97% DCM, 3% MeOH). The product fractions were collected and evaporated to dryness yielding 2 fractions Fraction 1 : 80 mg of a compound which was dissolved in ACN, crystallized from CAN. The precipitate was filtered, washed with ACN then Et20 and dried yielding 27 mg (1%) intermediate 84. M.P.:187-188C (Kofler).Fraction 2: 550 mg of impure intermediate 83 was purified by achiral SFC(AMINO 6muetaiota 150x21.2mm; mobile phase 0.3% ISOPROPYLAMINE, 75% C02, 25% MeOH). The product fractions were collected and evaporated to dryness yielding 420 mg (21%) of intermediate 83.

Reference： [1]Patent: WO2013/61080,2013,A1 .Location in patent: Page/Page column 170; 171

5
[ 10075-50-0 ]
[ 148430-81-3 ]
[ 1315553-98-0 ]

Yield	Reaction Conditions	Operation in experiment
30.5%	With caesium carbonate; In N,N-dimethyl-formamide; at 70℃; for 1h;	Oxetan-3-yl methanesulfonate (1.397 g, 9.18 mmol) was added to a solution of 5-bromo- lH-indole (1.5 g, 7.65 mmol) in DMF (15 mL) followed by cesium carbonate (3.74 g, 1 1.48 mmol), and the mixture was stirred at 70 C for 1 h. Insoluble solids were filtered, the filtrate was concentrated and the residue was partitioned between ethyl acetate and water. Separated organic layer was dried over sodium sulfate and filtered. The filtrate was concentrated under reduced pressure and purified by flash chromatography using 5% ethyl acetate in hexanes to afford the title compound (0.6 g, 30.5%) as an oil. lH NMR (400 MHz, CDC13): delta 7.77 (d, J= 1.6 Hz, 1H), 7.42 (d, J= 3.2 Hz, 1H), 7.35 (d, J= 8.8 Hz, 1H), 7.30 (dd, J = 2.0 Hz, J2 = 8.8 Hz, 1H), 6.54 (d, J= 2.8 Hz, 1H), 5.58 - 5.45 (m, 1H), 5.17 (t, J= 7.2 Hz, 2H), 5.05 (t, J= 6.8 Hz, 2H). ESI-MS m/z = 252 (M+H)+.

Reference： [1]Patent: WO2014/81994,2014,A1 .Location in patent: Page/Page column 27

6
[ 148430-81-3 ]
sodium 2-(tert-butyl)-6-chlorobenzo[d]oxazole-7-thiolate [ No CAS ]
2-(tert-butyl)-6-chloro-7-(oxetan-3-ylthio)benzo[d]oxazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
2 g	With potassium carbonate; In N,N-dimethyl-formamide; at 80℃;	To a solution of sodium 2-(tert-butyl)-6-chlorobenzo[d]oxazole-7-thiolate (2.0 g) and <strong>[148430-81-3]oxetan-3-yl methanesulfonate</strong> (1.2 g) in DMF (50 mL) was added K2C03 (1.0 g). The resulting mixture was stirred at 80C overnight. After cooling, the mixture was poured into water andextracted with EA (2x100 mL). The combined organic phases were washed, dried and concentrated to afford 2-(tert-butyl)-6-ch loro-7-(oxetan-3-ylthio)benzo[d]oxazole (2.0 g). MS(ES) mlz 298 (MH).

Reference： [1]Patent: WO2015/181186,2015,A1 .Location in patent: Page/Page column 169
[2]Journal of Medicinal Chemistry,2018,vol. 61,p. 2518 - 2532

7
[ 148430-81-3 ]
[ 10387-40-3 ]
[ 1402428-24-3 ]

Yield	Reaction Conditions	Operation in experiment
100%	In N,N-dimethyl acetamide; at 65℃; for 16.16h;	At room temperature,16b (11.0 g, 2.0 mmol) was dissolved in N, N-dimethylformamide (70 mL), potassium thioacetate (0.28 g, 2.8 mmol) was added and stirred for 10 minutes.The reaction was heated to 65 C for 16 hours.Water (200 mL) was added to the reaction solution, extracted with methyl tertiary butyl ether (150 mL x 4), the organic phases were combined,Washed successively with water (100 mL x 2), saturated brine aqueous solution (100 mL x 2).Dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated under reduced pressure to give pale yellow liquid 16c (8.56 g, 100%).

Reference： [1]Patent: TW2017/8221,2017,A .Location in patent: Page/Page column 98; 99

8
[ 148430-81-3 ]
[ 106-41-2 ]
[ 1369534-96-2 ]

Reference： [1]Journal of Medicinal Chemistry,2017,vol. 60,p. 9769 - 9789

9
[ 269410-08-4 ]
[ 148430-81-3 ]
[ 1339890-99-1 ]

Yield	Reaction Conditions	Operation in experiment
13%		60% sodium hydride (0.873 g, 36.4 mmol) was added to the solution of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (3.482 g, 17.9 mmol) in N,N-dimethylformamide (30 mL) under an ice bath, then the mixture solution was stirred for 10 min. Then oxetan-3-yl methanesulfonate (2.80 g, 18.4 mmol) was added to the above reaction solution, then the reaction solution was stirred at 100 C. for 21 hrs. After the reaction was completed, the mixture solution was cooled to room temperature, diluted with ethyl acetate (15 mL), washed with a saturated ammonium chloride solution (15 mL), and then washed with a saturated brine (15 mL). The organic layer was dried and concentrated, and then separated by column chromatography [eluent: dichloromethane/methanol] to obtain 1-(oxetan-3-yl)-4-(4,4,5,5-tetramethyl)-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (0.587 g, yield 13%). MS m/z (ESI): 251 [M+H]+.

Reference： [1]Patent: US2020/71302,2020,A1 .Location in patent: Paragraph 0143; 0164; 0165

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H200	Unstable explosive
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H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
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. 148430-81-3 ] {[proInfo.proName]}

Quality Control of [ 148430-81-3 ]

Related Doc. of [ 148430-81-3 ]

Product Details of [ 148430-81-3 ]

Calculated chemistry of [ 148430-81-3 ]

Physicochemical Properties

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Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 148430-81-3 ]

Application In Synthesis of [ 148430-81-3 ]

[ 148430-81-3 ] Synthesis Path-Upstream 1~1

[ 148430-81-3 ] Synthesis Path-Downstream 1~9

Related Functional Groups of [ 148430-81-3 ]

Sulfonates

Related Parent Nucleus of [ 148430-81-3 ]

Aliphatic Heterocycles

Oxetanes

Precautionary Statements-General

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Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

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[ 148430-81-3 ]

Related Parent Nucleus of
[ 148430-81-3 ]