[ CAS No. 96-49-1 ] {[proInfo.proName]}

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Quality Control of [ 96-49-1 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 96-49-1 ]

SDS Specification

Alternatived Products of [ 96-49-1 ]

Product Citations

De novo syntheses of multi-linker Zn- and Co-based ZIFs with application in CO2 fixation

Abraha, Yuel W. ; Tsai, Chih-Wei ; Langner, Ernst H. G. Micropor. Mesopor. Mat.,2022,346,112319. DOI: 10.1016/j.micromeso.2022.112319

Abstract: Zeolitic Imidazolate Frameworks (ZIFs) and ZIF derivatives can catalyze the fixation of CO2 with epoxide substrates. Herein, we report a De Novo (direct mixing) synthesis method to produce nano-sized Zn- and Co-based Multi-Linker ZIFs (termed as ML-ZIFs) with polar 2-mercaptoimidazolate (SHIm) and non-polar 2-methylimidazolate (mIm) linkers, characterized by PXRD, TGA, TEM, 1H NMR, N2 and CO2 isotherms. All the ML-ZIFs have sodalite (SOD) topologies with permanent porosity and thermal stability of up to 250 °C. Both Zn- and Co-based ML-ZIFs were efficient in the fixation of CO2 with epichlorohydrin (ECH) and propylene-oxide (PrO) substrates without co-catalyst, showing improved catalytic activity over their single-linker counterparts (ZIF-8 and ZIF-67). ML-ZIF 5Co (with Co metal center and Co(mIm)1.68(SHIm)0.32 composition) showed a maximum Turn-Over Frequency (TOF) of 893 and 787 h-1 for CO2 fixation with PrO and ECH, respectively.

Keywords: Multi-linker frameworks ; Zeolitic imidazolate frameworks (ZIFs) ; Epoxides ; CO2 fixation ; Cycloaddition ; Catalysis

Purchased from AmBeed: 96-49-1 ; 82358-15-4

Product Details of [ 96-49-1 ]

CAS No. :	96-49-1	MDL No. :	MFCD00005382
Formula :	C₃H₄O₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	KMTRUDSVKNLOMY-UHFFFAOYSA-N
M.W :	88.06	Pubchem ID :	7303
Synonyms :

Calculated chemistry of [ 96-49-1 ] Expand+

Physicochemical Properties

Num. heavy atoms :	6
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.67
Num. rotatable bonds :	0
Num. H-bond acceptors :	3.0
Num. H-bond donors :	0.0
Molar Refractivity :	17.18
TPSA :	35.53 ?2

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) :	-6.63 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.02
Log Po/w (XLOGP3) :	0.29
Log Po/w (WLOGP) :	0.15
Log Po/w (MLOGP) :	-0.83
Log Po/w (SILICOS-IT) :	1.02
Consensus Log Po/w :	0.33

Druglikeness

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

Water Solubility

Log S (ESOL) :	-0.57
Solubility :	23.8 mg/ml ; 0.27 mol/l
Class :	Very soluble
Log S (Ali) :	-0.6
Solubility :	22.2 mg/ml ; 0.252 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	0.02
Solubility :	92.6 mg/ml ; 1.05 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.69

Safety of [ 96-49-1 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P260-P264-P270-P280-P301+P312+P330-P305+P351+P338-P314-P337+P313-P501	UN#:	N/A
Hazard Statements:	H302-H319-H373	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 96-49-1 ]

* 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 [ 96-49-1 ]
Downstream synthetic route of [ 96-49-1 ]

[ 96-49-1 ] Synthesis Path-Upstream 1~1

1
[ 96-49-1 ]
[ 1044870-30-5 ]
[ 1044870-39-4 ]

Yield	Reaction Conditions	Operation in experiment
95%	With potassium carbonate In N,N-dimethyl-formamide at 110℃; for 12 h;	Compound 10A (3.26 g, 10 mmol) was added to a 100 mL single-mouth bottle.Compound 11 is ethylene carbonate (0.88 g, 10 mmol),Add 30 mL of N,N-dimethylformamide to dissolve it.At the same time, potassium carbonate (1.38 g, 10 mmol) was added.Warm the system to 110 ° C,The reaction was refluxed for 12 hours.After the reaction is over,Add 20 mL of water to the reaction system.Extract three times with dichloromethane (3*20 mL),Combine the organic phase,Dry with anhydrous sodium sulfate,filter,Distilling under reduced pressure to obtain a mixture,Purified by column chromatography (the eluent is petroleum ether / ethyl acetate,Volume ratio 2:1),A yellow solid RVX-208 (3.51 g, yield 95percent) was obtained.

Reference： [1] Patent: CN108484510, 2018, A, . Location in patent: Paragraph 0041

[ 96-49-1 ] Synthesis Path-Downstream 1~10

1
[ 96-49-1 ]
[ 1198-14-7 ]
5-bromo-8-(2-hydroxyethyloxy)quinoline [ No CAS ]

Reference： [1]Pharmaceutical Chemistry Journal,1994,vol. 28,p. 934 - 936
Khimiko-Farmatsevticheskii Zhurnal,1994,vol. 28,p. 50 - 52

2
[ 96-49-1 ]
[ 773-76-2 ]
5,7-dichloro-8-(2-hydroxyethyloxy)quinoline [ No CAS ]

Reference： [1]Pharmaceutical Chemistry Journal,1994,vol. 28,p. 934 - 936
Khimiko-Farmatsevticheskii Zhurnal,1994,vol. 28,p. 50 - 52

3
[ 96-49-1 ]
[ 51746-85-1 ]
[ 401522-20-1 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2004,vol. 12,p. 3503 - 3519

4
[ 96-49-1 ]
[ 1137-42-4 ]
[ 14814-17-6 ]

Yield	Reaction Conditions	Operation in experiment
95%	With sodium iodide; In toluene; at 60℃; for 1.5h;Reflux;	4-hydroxybenzophenone (262 g, 1.32 mol)NaI (6.5 g, 0.043 mol),Ethylene carbonate (125 g, 1.42 mol) andToluene (10 mL) were added to a 2000 mL three-necked flask,Raise the temperature until the system is clear.Continue to raise the temperature to the reaction system was refluxed for 1.5h,After the TLC test reaction is completed, the heating is stopped,Cooled to 60 C.To the reaction system was added water and ethyl acetate,extraction,The organic phase was dried over anhydrous sodium sulfate,Concentrated to give 304 g of a pale yellow solid,Yield 95%.
94%	With sodium iodide; In toluene; at 99 - 176℃; for 0.5h;Product distribution / selectivity;	A mixture of ethylene carbonate (124.6 g; 1.07 eq.), sodium iodide (6.3 g; 0.03 eq.), 4-hydroxybenzophenone (262 g; 1 eq.) and toluene (8.1 g) was heated. At99C a clear solution was obtained. The reaction mixture was heated with reflux condenser to 176C over one hour, during which gas evolution occurred. After an additional ? hour at 176C, the reaction mixture was cooled to 122C and toluene (350 g) and water (24 g) was added. The lower phase was cut and discarded. More water (14 g) was added and the lower phase was again cut and discarded. Water and toluene (95 g in total) was azeotropically removed, reaching a boiling point of 11 1 C. More toluene (1 14 g) was added and the product was isolated by filtration at 8C. In total, 302 g of 4-(2-hydroxyethoxy)benzophenone (94%) was obtained after drying as white crystals (99.8 % chromatographic purity).
		from 4-hydroxy-benzophenone and ethylene carbonate there is obtained 2-(p-benzoylphenoxy)-ethanol, m.p. 78-80 C.;

Reference： [1]Patent: CN104788300,2017,B .Location in patent: Paragraph 0038; 0039; 0040;
[2]Patent: WO2011/89385,2011,A1 .Location in patent: Page/Page column 23
[3]Patent: US4625048,1986,A

5
[ 96-49-1 ]
[ 103-49-1 ]
[ 101-06-4 ]

Yield	Reaction Conditions	Operation in experiment
83%	With tetra-(n-butyl)ammonium iodide; at 20 - 140℃; for 26h;	Preparation Example: Preparation Acetic acid 2-dibenzylamino-ethyl ester; Stepi : 0.5 gram of dibenzylamine (2.5 mmol), 0.446 gram of ethylenecarbonate (5 mmol) and 0.215 gram of tetraethylammoniumiodide (083 mmol) were mixed together at room temperature. The solid mixture was then heated at 1409C and the resulting suspension was stirred at this temperature for 26 hours. The reaction mixture was diluted with ethyl acetate and extracted with 1 OmL of a 0.5M solution of sodium hydroxide. The aqueous phase was washed with ethyl acetate and the combined organic phases were washed twice with brine. The organic phase was dried on magnesium sulfate, filtered, concentrated under reduced pressure and purified by flash chromatography on silica gel (eluant: ethylacetate/hexane 1/2) to afford 0.5 gram of N, N- dibenzyl-2-aminoethanol (yield: 83%) as an oil.

Reference： [1]Patent: WO2008/62006,2008,A1 .Location in patent: Page/Page column 13

6
[ 96-49-1 ]
[ 3347-62-4 ]
[ 196810-78-3 ]

Yield	Reaction Conditions	Operation in experiment
59.6%		Sodium hydride (2.5 g, 1.5 g NaH, 62 mmol, 1.1 equiv) is added over aperiod of 3 min to a solution of 5-methyl-3-phenyl-lJ7-pyrazole (9.00 g, 56.9 mmol,1 equiv) in DMF (90 mL) cooled to 0 C in an ice bath. After stilling 15 min, ethylenecarbonate (7.6 mL, 10 g, 110 mmol, 2.0 equiv) is added. The bath is removed, and thereaction mixture is stirred for 15 h. The mixture is treated with 4 M aq K2CO3 (90 mL),heated at reflux for 5 h, and diluted with H2O (200 mL). After allowing the hot mixtureto cool for 15 min, more H2O (100 mL) and then hexanes (100 mL) are added. Themixture is shaken vigorously and then allowed to separate. Crystals formed and stayedwith the top organic layer. The aqueous layer is separated, and the crystals are collectedby vacuum filtration and washed with hexanes (2x50 mL). The crystals are dissolved inEt2O/EtOAc (1:1; 200 mL), and the solution is dried (Na2SO4), filtered, and concentrated(75 C) to give the title compound as an off-white crystalline solid (6.86 g, 59.6%).HRMS Calculated for Ci2Hi5N2O: m/z 203.1 184. Found: 203.1 168

Reference： [1]Patent: WO2005/51945,2005,A1 .Location in patent: Page/Page column 80-81

7
[ 96-49-1 ]
[ 2233-18-3 ]
[ 1039948-89-4 ]

Yield	Reaction Conditions	Operation in experiment
96%	With potassium carbonate; In N,N-dimethyl-formamide; at 110℃;	To a solution of 3, 5-dimethyl-4-hydroxybenzaldehyde (1.50 g, 10 mmol) in DMF (30 mL) was added ethylene carbonate (0.88 g, 10 mmol) and K2CO3, and warmed to 110 for refluxing overnight. The reaction mixture then was added water (20 mL), extracted for 3 times with CHCl3, and organic phase was dried overnight, filtered, vacuum distillated, purified by column chromatography (2:1, petroleum ether/ethyl acetate) to afford 14 (1.86 g, 96 %) as yellow oil liquid. 1H NMR (600 MHz, CDCl3) delta: 9.88 (s, 1H), 7.57 (s, 2H), 5.30 (s, 1H), 4.00-3.98 (m, 2H), 3.96 (d, J = 4.9, 3.5 Hz, 2H), 2.36 (s, 6H). MS (ESI) m/z: 217.1 [M + Na]+.
78.8%	With potassium carbonate; In N,N-dimethyl-formamide; at 110℃;Inert atmosphere;	The starting material 4-hydroxy-3,5-dimethylbenzaldehyde (1; 70 kg), K2CO3 (9.8 kg) and DMF (133 kg) were mixed and stirred at 110 0C under nitrogen. Ethylene carbonate (45.6 kg) in DMF (46 kg) was added to the mixture over a period of 4 hours, using a diaphragm pump. The reaction mixture was stirred at 110 0C for 12 hours, until less than 5% of the starting material 1 remained. The reaction mixture <n="17"/>was cooled to 25 0C and water (1300 kg) was added followed by a mixture of dichloromethane and heptane (3V/2V; 1300 kg). The mixture was agitated for 30 minutes. The organic layer was isolated and the aqueous layer was back extracted with a mixture of dichloromethane and heptane (3V/2V; 1300 kg). The combined organic layers were washed with aqueous sodium hydroxide (3 M; 460 kg), followed by three washes with water (3 x 710 kg), and dried over sodium sulfate (60 kg). Dichloromethane was removed from the dried organic layer by distillation, keeping the temperature below 40 0C. Heptane (260 kg) and seed crystals were added to initiate crystallization and the mixture was stirred at 20 0C for 2 hours. The mixture was filtered, washed with heptane (60 kg), and dried under vacuum until constant weight to afford intermediate 2 (71.3 kg, 78.8%). 1H-NMR (DMSO-d6): delta 9.82 (1 H), 7.54 (2H), 4.96 (1 H), 3.85 (2H), 3.74 (2H), 2.29 (6H).

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2019,vol. 29,p. 2168 - 2172
[2]Patent: WO2009/158404,2009,A1 .Location in patent: Page/Page column 15-16

8
[ 96-49-1 ]
[ 2785-78-6 ]
[ 1270038-99-7 ]

Reference： [1]Heterocycles,2010,vol. 82,p. 491 - 504

9
[ 96-49-1 ]
[ 3469-69-0 ]
[ 1408334-75-7 ]

Yield	Reaction Conditions	Operation in experiment
53%	In N,N-dimethyl-formamide; at 125℃; for 24h;	a. 2-(4-Iodo-pyrazol-1-yl)-ethanol (Intermediate Aa) A solution of 4-iodopyrazole (14.3 g, 73.9 mmol) and ethylene carbonate (6.83g, 77.6 mmol) in DMF (50 mL) was stirred at 125 C. for 24 h. The cooled solution was concentrated under vacuum to leave a brown oil. The residue was purified by FCC using 30-70% EtOAc in DCM to give the title compound (9.36 g, 53%). LCMS (Method 3): Rt 2.24 min, m/z 239 [MH+].
53%	In N,N-dimethyl-formamide; at 125℃; for 24h;	A solution of 4-iodopyrazole (14.3 g, 73.9 mmol) and ethylene carbonate (6.83g, 77.6 mmol) in DMF (50 mL) was stirred at 125 C for 24 h. The cooled solution was concentrated under vacuum to leave a brown oil. The residue was purified by FCC, using 30-70% EtOAc in DCM, to give the title compound (9.36 g, 53%). LCMS (Method 3): Rt 2.24 min, m/z 239 [MH+].
53%	In N,N-dimethyl-formamide; at 125℃; for 24h;	A solution of 4-iodopyrazole (14.3 g, 73.9 mmol) and ethylene carbonate (6.83g, 77.6 mmol) in DMF (50 mL) was stirred at 125C for 24 h. The cooled solution was concentrated under vacuum to leave a brown oil. The residue was purified by FCC using 30-70% EtOAc in DCM to give the title compound (9.36 g, 53%). LCMS (Method 3): Rt 2.24 min, m/z 239 [MH+].

53%

In N,N-dimethyl-formamide; at 125℃; for 24h;

A solution of 4-iodopyrazole (14.3 g, 73.9 mmol) and ethylenecarbonate (6.83g, 77.6 mmol) in DMF (50 mL) was stirred at 125 C for 24 h.The cooled solution was concentrated under vacuum to leave a brown oil. Theresidue was purified by FCC, using 30-70% EtOAc in DCM, to give the titlecompound (9.36 g, 53%).

Reference： [1]Patent: US2014/364411,2014,A1 .Location in patent: Paragraph 0423; 0424
[2]Patent: WO2014/194956,2014,A1 .Location in patent: Page/Page column 42
[3]Patent: WO2014/195400,2014,A1 .Location in patent: Page/Page column 92
[4]Patent: KR2016/16973,2016,A .Location in patent: Paragraph 0221-0223

10
[ 96-49-1 ]
[ 4522-35-4 ]
2-(3-iodo-pyrazol-1-yl)-ethanol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
72%	In N,N-dimethyl-formamide; at 150℃; for 3h;	a. 2-(3-Iodo-pyrazol-1-yl)-ethanol (Intermediate Fa) A solution of <strong>[4522-35-4]3-iodo-1H-pyrazole</strong> (500 mg, 2.6 mmol) and ethylene carbonate (238 mg, 2.70 mmol) was formed in DMF (5 mL) and heated at 150 C. for 3 h.
72%	In N,N-dimethyl-formamide; at 150℃; for 3h;	A solution of 3-iodo-lH-pyrazole (500 mg, 2.6 mmol) and ethylene carbonate (238 mg, 2.70 mmol) was formed in DMF (5 mL) and heated at 150C for 3 h. The mixture was allowed to cool then evaporated under vacuum to remove the solvent. Purification of the residue by FCC eluting with a gradient of 0-100% EtOAc in cyclohexane gave crude title compound (444 mg, 72%) as a brown oil. LCMS (Method 3): Rt 2.17 min, m/z 239 [MH+].
72%	In N,N-dimethyl-formamide; at 150℃; for 3h;	A solution of 3-iodo-lH-pyrazole (500 mg, 2.6 mmol) and ethylenecarbonate (238 mg, 2.7 mmol) was formed in DMF (5 mL) and heated at150C for 3 h. The mixture was allowed to cool then evaporated undervacuum to remove the solvent. Purification of the residue by FCC, elutingwith a gradient of 0-100% EtOAc in cyclohexane, gave crude title compound(444 mg, 72%).

In N,N-dimethyl-formamide; at 150℃; for 3h;

A solution of 3-iodo-lH-pyrazole (500 mg, 2.6 mmol) and ethylene carbonate (238 mg, 2.7 mmol) was formed in DMF (5 mL) and heated at 150C for 3 h. The mixture was allowed to cool then evaporated under vacuum to remove the solvent. Purification of the residue by FCC, eluting with a gradient of 0- 100% EtOAc in cyclohexane, gave crude title compound (444 mg, 72%). LCMS (Method 3): Rt 2.17 min, m/z 239 [MH+].

Reference： [1]Patent: US2014/364411,2014,A1 .Location in patent: Paragraph 0464; 0465
[2]Patent: WO2014/195400,2014,A1 .Location in patent: Page/Page column 101
[3]Patent: KR2016/16973,2016,A .Location in patent: Paragraph 0298-0300
[4]Patent: WO2014/194956,2014,A1 .Location in patent: Page/Page column 62

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[ 96-49-1 ]

A1462416[ 1173023-62-5 ]

1,3-Dioxolan-2-one-2,4,5-13C3

Reason: Stable Isotope

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P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

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
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

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[ CAS No. 96-49-1 ] {[proInfo.proName]}

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[ 96-49-1 ] Synthesis Path-Upstream 1~1

[ 96-49-1 ] Synthesis Path-Downstream 1~10

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