[ CAS No. 1420800-16-3 ] {[proInfo.proName]}

Name: 1420800-16-3|Oxetane-3-carbonitrile|95%
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SKU: A657972
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Cat. No.: {[proInfo.prAm]}

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Quality Control of [ 1420800-16-3 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 1420800-16-3 ]

SDS Specification

Alternatived Products of [ 1420800-16-3 ]

Product Details of [ 1420800-16-3 ]

CAS No. :	1420800-16-3	MDL No. :	MFCD21848216
Formula :	C₄H₅NO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	PXDVPPINZKNVNF-UHFFFAOYSA-N
M.W :	83.09	Pubchem ID :	71695437
Synonyms :

Calculated chemistry of [ 1420800-16-3 ]

Physicochemical Properties

Num. heavy atoms :	6
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.75
Num. rotatable bonds :	0
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	20.06
TPSA :	33.02 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) :	-7.11 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.94
Log Po/w (XLOGP3) :	-0.42
Log Po/w (WLOGP) :	0.16
Log Po/w (MLOGP) :	-0.72
Log Po/w (SILICOS-IT) :	0.89
Consensus Log Po/w :	0.17

Druglikeness

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

Water Solubility

Log S (ESOL) :	-0.09
Solubility :	67.5 mg/ml ; 0.812 mol/l
Class :	Very soluble
Log S (Ali) :	0.19
Solubility :	129.0 mg/ml ; 1.55 mol/l
Class :	Highly soluble
Log S (SILICOS-IT) :	-0.19
Solubility :	53.3 mg/ml ; 0.641 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.41

Safety of [ 1420800-16-3 ]

Signal Word:	Danger	Class:	6.1
Precautionary Statements:	P261-P264-P270-P271-P280-P302+P352-P304+P340-P310-P330-P361-P403+P233-P405-P501	UN#:	3276
Hazard Statements:	H301-H311-H331	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 1420800-16-3 ]

* 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.

Downstream synthetic route of [ 1420800-16-3 ]

[ 1420800-16-3 ] Synthesis Path-Downstream 1~7

1
[ 624-92-0 ]
[ 1420800-16-3 ]
[ 1425506-92-8 ]

Yield	Reaction Conditions	Operation in experiment
161 mg	With n-butyllithium; diisopropylamine In tetrahydrofuran at -78 - 0℃; for 4h;	5A.1 To a solution of diisopropylamine (3.57 niL, 25.3 mmol) in THF (50 mL) at 0°C was added n- butyllithium (9.63 ml, 24.07 mmol) dropwise, and the mixture was stirred at 0°C for 30 minutes. The resulting LDA solution was cooled to -78°C and a solution of compound 5A-1 (1.0 g, 12.04 mmol) in 2 mL THF was added at -78°C and stirred for 30 minutes at that temperature. A solution of MeSSMe (2.18 mL, 24.07 mmol) in 1 mL of THF was added and the mixture was stirred at -78°C for 3 hours. The reaction was quenched by addition of saturated aq. NH4C1 and extracted with ethyl acetate. The combined organic extracts were concentrated; the residue was purified by flash chromatography (40 g of S1O2) eluting with 0- 100% ethyl acetate/hexane to give compound 5A-2 (161 mg). XH NMR (CDC13, 500 MHz) δ 5.08 (m, 2 H), 4.78 (m, 2 H), 2.22 (s, 3 H).
161 mg	Stage #1: oxetane-3-carbonitrile With n-butyllithium; diisopropylamine; lithium diisopropyl amide In tetrahydrofuran at -78 - 0℃; for 1h; Stage #2: Dimethyldisulphide In tetrahydrofuran at -78℃; for 3h;	1 Step 1 (0617) To a solution of diisopropylamine (3.57 mL, 25.3 mmol) in THF (50 mL) at 0° C. was added n-butyllithium (9.63 ml, 24.07 mmol) dropwise, and the mixture was stirred at 0° C. for 30 minutes. The resulting LDA solution was cooled to -78° C. and a solution of compound 5A-1 (1.0 g, 12.04 mmol) in 2 mL THF was added at -78° C. and stirred for 30 minutes at that temperature. A solution of MeSSMe (2.18 mL, 24.07 mmol) in 1 mL of THF was added and the mixture was stirred at -78° C. for 3 hours. The reaction was quenched by addition of saturated aq. NH4Cl and extracted with ethyl acetate. The combined organic extracts were concentrated; the residue was purified by flash chromatography (40 g of SiO2) eluting with 0-100% ethyl acetate/hexane to give compound 5A-2 (161 mg). 1H NMR (CDCl3, 500 MHz) δ 5.08 (m, 2H), 4.78 (m, 2H), 2.22 (s, 3H).

Reference： [1]Current Patent Assignee: MERCK & CO INC - WO2013/28670, 2013, A1 Location in patent: Page/Page column 79; 80
[2]Current Patent Assignee: MERCK & CO INC - US9181236, 2015, B2 Location in patent: Page/Page column 84

2
[ 1420800-16-3 ]
[ 2173509-66-3 ]
[ 2173511-74-3 ]

Yield	Reaction Conditions	Operation in experiment
29.1 mg	Stage #1: oxetane-3-carbonitrile With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 0.5h; Inert atmosphere; Stage #2: (S)-N-{3-[2-(3-chlorophenyl)-1,3-dioxolan-2-yl]propylidene}-2-methylpropane-2-sulfinamide In tetrahydrofuran at -78℃; for 2h; Inert atmosphere;	5-30-A (S)-N-[(1R)-3-[2-(3-Chlorophenyl)-1,3-dioxolan-2-yl]-1-(3-cyanooxetan-3-yl)propyl]-2-methylpropane-2- sulfinamide To a solution of LDA (1.13 mol/L, THF) (0.550 mL) in THF (3 mL) was added a solution of oxetane-3-carbonitrile (0.048 mL) in THF (0.6 mL) under an argon atmosphere at -78°C. The mixture was stirred at the same temperature for 30 minutes, and then to the mixture was added a solution of Reference Example 1-8-B (100 mg) in THF (0.6 mL) at -78°C. The reaction mixture was stirred at -78°C for 2 hours, and then to the reaction mixture were added a saturated aqueous solution of ammonium chloride, water and dichloromethane. The mixture was stirred. The organic layer was separated, and then concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=60/40-0/100) to give the title compound (29.1 mg).

Reference： [1]Current Patent Assignee: KISSEI PHARMACEUTICAL COMPANY LIMITED - EP3459941, 2019, A1 Location in patent: Paragraph 0387

3
oxetane-3-carbonitrile [ No CAS ]
[ 375368-83-5 ]
3-(5-bromo-6-methylpyridin-2-yl)oxetane-3-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium hexamethylsilazane; In tetrahydrofuran; toluene; at 0℃; for 0.0833333h;Inert atmosphere;	To a vial equipped with a stir bar was added <strong>[375368-83-5]3-bromo-6-fluoro-2-methylpyridine</strong> (200 mg, 1.05 mmol), oxetane-3-carbonitrile (87 mu, 1.19 mmol), and toluene (5260 mu). The mixture was cooled to 0 C while stirring under Nitrogen. KHMDS 1.0 M in THF (1260 mu, 1.26 mmol) was slowly added dropwise while stirring at 0 C. The mixture was stirred for 5 min. After 5 min the reaction was quenched via the addition of methanol. The material was filtered over Celite, rinsing with EtOAc. The organics were concentrated under reduced pressure. The material was dissolved in DCM (with a few drop of MeOH for solubility) and the residue was purified by column chromatography on silica (0-100% EtOAc/hexanes) to afford 3- (5-bromo-6-methylpyridin-2-yl)oxetane-3-carbonitrile. MS ESI calc'd. [M + H]+ 253, found 253.

Reference： [1]Patent: WO2019/74748,2019,A1 .Location in patent: Page/Page column 44; 45

4
[ 766-11-0 ]
[ 1420800-16-3 ]
[ 2328100-90-7 ]

Yield	Reaction Conditions	Operation in experiment
47%	With potassium hexamethylsilazane In tetrahydrofuran; toluene at 0℃; for 0.0833333h; Inert atmosphere;
	With potassium hexamethylsilazane In tetrahydrofuran; toluene at 0℃; for 0.0833333h; Inert atmosphere;	76.1 Step 1: 3-(5-bromopyridin-2-yl)oxetane-3-carbonitrile (I-152) To a vial equipped with a stir bar was added 255 5-bromo-2-fluoropyridine (58.5 μl, 0.568 mmol), 256 oxetane-3-carbonitrile (47.2 μl, 0.625 mmol) and 166 toluene (2840 μl). The reaction mixture was cooled to 0° C. while stirring under nitrogen. 257 KHMDS 1.0 M in 45 THF (682 μl, 0.682 mmol) was slowly added to the stirring reaction mixture. After 5 min the reaction was quenched with 139 MeOH (5 ml). The crude reaction mixture was filtered over a Celite pad which was rinsed with ethyl acetate. The reaction mixture was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (0-100% EtOAc/hexanes). Desired product was eluted and fractions were collected and concentrated under reduced pressure to afford compound 258 I-152. MS (ESI) [M+H]+: m/z 239.

Reference： [1]Abeywickrema, Pravien; Andrews, Christine; Augustin, Martin; Bennett, David Jonathan; Cheng, Mangeng; Cowley, Phillip; Curran, Patrick; Fradera, Xavier; Geda, Prasanthi; Han, Yongxin; Heo, Mee Ra; Joshi, Elizabeth M.; Knemeyer, Ian; Lesburg, Charles A.; Lim, Jongwon; McGowan, Meredeth A.; Miller, J. Richard; Nickbarg, Elliott B.; Otte, Karin; Sciammetta, Nunzio; Smotrov, Nadya; Song, Xuelei; Spacciapoli, Peter; Trewick, Sarah; Von Köenig, Konstanze; White, Catherine; Woo, Hyun; Yu, Wensheng; Zhou, Hua [ACS Medicinal Chemistry Letters, 2020, vol. 11, # 4, p. 550 - 557]
[2]Current Patent Assignee: MERCK & CO INC - US2019/144433, 2019, A1 Location in patent: Paragraph 1095; 1096

5
[ 1420800-16-3 ]
[ 2328101-55-7 ]
[ 2328101-56-8 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium hexamethylsilazane In tetrahydrofuran; toluene at 0℃; for 0.166667h;	120.2 Step 2: 3-(5-bromo-4-(((tert-butyldimethylsilyl)oxy)methyl)pyridin-2-yl)oxetane-3-carbonitrile (C) To a 50 ml round-bottomed flask with a stir bar under nitrogen was added 621 5-bromo-4-(((tert-butyldimethylsilyl)oxy)methyl)-2-fluoropyridine (B) (712 mg, 2.22 mmol), 256 oxetane-3-carbonitrile (185 μl, 2.45 mmol), and 166 toluene (18 mL). The flask was cooled to 0° C. and 257 KHMDS (2668 μl, 2.67 mmol, 1.0 M in 45 THF) was added dropwise with stirring. The solution was stirred for 10 min at 0° C., after which the reaction was quenched with the slow addition of 139 MeOH with stirring. The resulting mixture was diluted with EtOAc and water, and the aqueous layer was extracted with EtOAc, and the combined organics were washed with brine, dried over MgSO4, and concentrated under reduced pressure. The residue was then purified via flash chromatography to afford the 623 title compound. MS (ESI): 383, 385 [M+H]+.

Reference： [1]Current Patent Assignee: MERCK & CO INC - US2019/144433, 2019, A1 Location in patent: Paragraph 1257; 1259

6
[ 1480-64-4 ]
oxetane-3-carbonitrile [ No CAS ]
3-(3-chloropyridin-2-yl)oxetane-3-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%	With potassium hexamethylsilazane In tetrahydrofuran; toluene at 0 - 20℃; for 0.5h;	1.54.1 Step 1 Into a 50-mL 3-nec , p oro-2-fluoropyridine (1.20 g, 9.12 mmol, 1.00 eq.), oxetane-3-carbonitrile (839 mg, 10.10 mmol, 1.10 eq.) in toluene (20.00 mL), followed by the addition of KHMDS (1M in THF) (11.00 mL, 10.94 mmol, 1.2 eq.) at 0 oC. After addition, the resulting solution was stirred for 30 min at room temperature. The reaction was then quenched by the addition of NH4Cl (aq) (30.00 mL), and extracted with ethyl acetate (50.00 mL X 2). The combined organic phase was dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by silica gel column eluting with ethyl acetate/petroleum ether (1/3) to afford 3-(3-chloropyridin-2-yl)oxetane-3-carbonitrile as a yellow solid (1.38 g, 78%). LCMS (ES) [M+1]+ m/z: 195.

Reference： [1]Current Patent Assignee: GLOBAL BLOOD THERAPEUTICS, INC. - WO2021/202796, 2021, A1 Location in patent: Paragraph 337-339

7
[ 1420800-16-3 ]
[ 112704-79-7 ]
[ 2771024-37-2 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium bis-(trimethyl-silyl)amide In tetrahydrofuran at -78 - 25℃; for 12h; Inert atmosphere;	92 4-bromo-2-(3-cyanooxetan-3-yl)benzoic acid To a solution of 4-bromo-2-fluorobenzoic acid (500 mg, 2.28 mmol) and oxetane-3-carbonitrile (500 mg, 6.02 mmol) in THF (10 mL) at -78 °C was added NaHMDS (5.02 mL, 1 M in THF). The reaction mixture was stirred at 25 °C for 12 h. The reaction mixture was poured into sat. aq. NH4Cl (20 mL) and extracted with EtOAc (3 × 10 mL). The combined organics were dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure to provide a residue that was used directly. LCMS: m/z = 279.9, 281.9 [M-H]-.
	With sodium bis-(trimethyl-silyl)amide In tetrahydrofuran at -78 - 25℃; for 12h; Inert atmosphere;	92 4-bromo-2-(3-cyanooxetan-3-yl)benzoic acid To a solution of 4-bromo-2-fluorobenzoic acid (500 mg, 2.28 mmol) and oxetane-3-carbonitrile (500 mg, 6.02 mmol) in THF (10 mL) at -78 °C was added NaHMDS (5.02 mL, 1 M in THF). The reaction mixture was stirred at 25 °C for 12 h. The reaction mixture was poured into sat. aq. NH4Cl (20 mL) and extracted with EtOAc (3 × 10 mL). The combined organics were dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure to provide a residue that was used directly. LCMS: m/z = 279.9, 281.9 [M-H]-.

Reference： [1]Current Patent Assignee: DENALI THERAPEUTICS INC - WO2022/109268, 2022, A1 Location in patent: Paragraph 0209; 0473
[2]Current Patent Assignee: DENALI THERAPEUTICS INC - WO2022/109268, 2022, A1 Location in patent: Paragraph 0209; 0473

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[ 1420800-16-3 ]

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Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
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
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
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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. 1420800-16-3 ] {[proInfo.proName]}

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[ 1420800-16-3 ] Synthesis Path-Downstream 1~7

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