[ CAS No. 1137-42-4 ] {[proInfo.proName]}

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Quality Control of [ 1137-42-4 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 1137-42-4 ]

SDS Specification

Alternatived Products of [ 1137-42-4 ]

Product Details of [ 1137-42-4 ]

CAS No. :	1137-42-4	MDL No. :	MFCD00002355
Formula :	C₁₃H₁₀O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	NPFYZDNDJHZQKY-UHFFFAOYSA-N
M.W :	198.22	Pubchem ID :	14347
Synonyms :

Safety of [ 1137-42-4 ]

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

Application In Synthesis of [ 1137-42-4 ]

* 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 [ 1137-42-4 ]
Downstream synthetic route of [ 1137-42-4 ]

[ 1137-42-4 ] Synthesis Path-Upstream 1~1

1
[ 1137-42-4 ]
[ 6322-83-4 ]

Reference： [1] Tetrahedron Letters, 2004, vol. 45, # 10, p. 2239 - 2241
[2] Anales de la Real Sociedad Espanola de Fisica y Quimica, vol. 24, p. 88[3] Chemisches Zentralblatt, 1926, vol. 97, # II, p. 21
[4] Medicinal Chemistry, 2014, vol. 10, # 1, p. 59 - 65
[5] Journal of Mass Spectrometry, 2015, vol. 50, # 2, p. 407 - 417
[6] European Journal of Medicinal Chemistry, 2015, vol. 106, p. 50 - 59

[ 1137-42-4 ] Synthesis Path-Downstream 1~11

1
[ 1137-42-4 ]
[ 107-07-3 ]
[ 14814-17-6 ]

Yield	Reaction Conditions	Operation in experiment
21%	With potassium carbonate; sodium iodide; In acetone;Heating / reflux;	Step 1: {4-[(2-Hydroxyethyl)oxy]phenyl}(phenyl)methanone (5)To a solution of 4-hydroxybenzophenone (6.0 g, 29.7 mmol) in acetone (50 mL) were added K2CO3 (12.3 g, 89.0 mmol) and 2-chloroethanol (4.0 mL, 59.3 mmol), followed by addition of NaI (4.50 g, 29.7 mmol). The reaction mixture was refluxed under nitrogen overnight. The mixture was cooled to room temperature. The white solid was filtered off and washed with acetone (100 mL). The filtrate was concentrated to a brown oil residue with some white solid. EtOAc (200 mL) was added, the white solid was filtered off and then washed with 50 mL of EtOAc. The filtrate was washed with 1 N NaOH, water, brine and dried over Na2SO4. Concentration afforded a pale yellow oil which was further purified by chromatography on a silica gel column eluted with a gradient from hexanes to 60% EtOAc:hexanes to give 5 as a white solid (1.52 g, 21%). 1H NMR (400 MHz, CDCl3): delta 4.00-4.05 (m, 2H), 4.15-4.20 (m, 2H), 6.98 (d, J=8.7 Hz, 2H), 7.45-7.50 (m, 2H), 7.55-7.60 (m, 1H), 7.75 (d, J=7.1 Hz, 2H), 7.83 (d, J=8.8 Hz, 2H).
		Preparation of Compound I; Synthesis of 3-(2-methylaziridin-l-yl)propionic acid 2-(4-benzoylphenoxy)ethyl ester (AZBP); To a 250 mL, one -neck, round bottom flask equipped with a magnetic stirrer were added sodium hydroxide (10.0 g, 0.250 mol) in a water (45 mL)/ethanol (20 mL) solution and 4-hydroxybenzophenone (Alfa Aesar, 50.0 g, 0.250 mol) and the mixture was heated to 55 0C. Chloroethanol (Aldrich, 20.3 g, 0.250 mol) in ethanol (25 mL) was then added dropwise to the reaction flask and the mixture heated to 75 0C for 8 hours then cooled to room temperature. The precipitate was collected by filtration, washed with water and recrystallized three times from ethanol/water to obtain 24.4 g of a white solid (4-(2- hydroxyethoxy)benzophenone).

Reference： [1]Patent: US2008/167360,2008,A1 .Location in patent: Page/Page column 19
[2]Patent: US2182786,1938,
[3]Patent: WO2010/65355,2010,A1 .Location in patent: Page/Page column 23

2
[ 1137-42-4 ]
[ 6322-83-4 ]

Reference： [1]Tetrahedron Letters,2004,vol. 45,p. 2239 - 2241
[2]Anales de la Real Sociedad Espanola de Fisica y Quimica,vol. 24,p. 88
Chemisches Zentralblatt,1926,vol. 97,p. 21
[3]Medicinal Chemistry,2014,vol. 10,p. 59 - 65
[4]Journal of Mass Spectrometry,2015,vol. 50,p. 407 - 417
[5]European Journal of Medicinal Chemistry,2015,vol. 106,p. 50 - 59
[6]Journal of Enzyme Inhibition and Medicinal Chemistry,2019,vol. 34,p. 1051 - 1061

3
[ 1137-42-4 ]
TentaGel-N(R)C(O)CH₂C₂F₄OC₂F₄SO₂F [ No CAS ]
[ 14814-17-6 ]

Reference： [1]Journal of the American Chemical Society,2001,vol. 123,p. 2695 - 2696

4
[ 1137-42-4 ]
[ 14814-17-6 ]

Reference： [1]Journal of Medicinal Chemistry,1997,vol. 40,p. 2314 - 2322

5
[ 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

6
[ 126-83-0 ]
[ 1137-42-4 ]
[ 115010-26-9 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; sodium hydroxide; In ethanol; water;	EXAMPLE 2 Sodium 2-hydroxy-3-(4-benzoylphenoxy)propane sulphonate A solution of sodium hydroxide (3.3g) in water (5 mls) was added to a solution of sodium 3-chloro-2-hydroxypropane sulphonate (14.73g) in water (30 mls) and the resultant solution added to a solution of 4-hydroxybenzophenone (9.9g) in ethanol (50 mls). After stirring under reflux for 18 hours, the pH of the pale yellow solution was brought to 4 via the addition of 4N. hydrochloric acid and after cooling in an ice bath for several hours the crude title compound was filtered and twice washed with ethanol (20 ml portions) and dried at 50C. giving a pale brown sandy solid (11.58g) of melting point equal to 320-323C. Recrystallisation with charcoaling from a mixture of ethanol (50 mls) and water (15 mls) followed by filtration, washing and drying gave sodium 2-hydroxy-3-(4-benzoylphenoxy) propane sulphonate (9.84g; yield = 55%) as a pale brown sandy solid of melting point equal to 316-318C. Analysis:- Calcd for C16H15NaO6S C 53.63; H 4.22; S 8.95; Na 6.42 Found: C 53.57; H 4.24; S 8.75; Na 6.69 An aqueous solution of this compound has an absorption maximum at 294 nm with an extinction coefficient (1%, 1cm) of 467.

Reference： [1]Patent: EP279475,1988,A2

7
[ 75-21-8 ]
[ 1137-42-4 ]
[ 14814-17-6 ]

Yield	Reaction Conditions	Operation in experiment
82%		I a) Ethylene glycol p-benzophenone ether; In a laboratory autoclave having a capacity of 2 L there were placed 520 g of diethylene glycol diethyl ether, 286 g of p-hydroxybenzophenone (>98 wt %), and 0.8 g of powdered potassium hydroxide. A pressure test was then carried out for 30 minutes using dry nitrogen. Following pressure let-down to atmospheric pressure and heating of the reaction mixture under a blanket of nitrogen to 120 C., 95.4 g of ethylene oxide were continuously forced in to give a maximum internal pressure of 4 bar over a period of 1 h. On completion of gassing with ethylene oxide, the reaction mixture was allowed to react, until the pressure remained constant for at least 30 minutes. The reaction mixture was discharged from the autoclave in the hot state, neutralized with 5 wt % strength aqueous hydrochloric acid, and poured into 2 L of ice water, and the reaction product was caused to crystallize by constant agitation. The resulting solid matter was filtered off in vacuo, washed with ice water and dried in vacuo (40 C., 10 mbar absolute). The resulting filtrate was concentrated in a rotary film evaporator to 20% of its volume, the precipitated product filtered off in vacuo, washed with ice water and likewise dried in vacuo. The total yield was 82% of theory.

Reference： [1]Patent: US2004/249186,2004,A1 .Location in patent: Page 7

8
[ 1137-42-4 ]
[ 540-51-2 ]
[ 14814-17-6 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In N,N-dimethyl-formamide; at 90℃; for 24h;	4-hydroxy benzophenone (9.9 g, 50 mmol), 2-bro-moethanol (7.5 g, 60 mmol) and potassium carbonate (10 g, 75 mmol) were added to N,N-dimethylformamide (DMF, 150 mE), and stirred at 90 C. for one day. A solvent was distilled off, and dichioromethane was added. The mixture extracted with water and saturated saline solution, and dried. A solvent was distilled off to obtain a pale yellow powder (crude yield 12 g). This compound was used in the next reaction.

Reference： [1]Soft Matter,2013,vol. 9,p. 929 - 937
[2]Advanced Functional Materials,2018,vol. 28
[3]Macromolecules,2010,vol. 43,p. 249 - 261
[4]RSC Advances,2018,vol. 8,p. 6798 - 6804
[5]Patent: US2018/50983,2018,A1 .Location in patent: Paragraph 0670; 0671; 0672

9
[ 814-68-6 ]
[ 1137-42-4 ]
[ 22535-49-5 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In dichloromethane; water;Flow reactor;	General procedure: For EX-1, the following procedure was carried out using Microreactor B, described above, with the mixing device at ambient temperature. Syringe I contained 15 g BP, 22 g TEA, and 22 g water. Syringe II contained 3 g ACL and 20 g DCM. Each syringe was placed in a separate syringe pump and the pump speeds were controlled to deliver the blends at the flow rates indicated for EX-1 in Table 3 below. The two unused addition ports of the mixing device were sealed with plugs. The molar flow ratios of BP: ACL: TEA pumped to the mixing device were 1: 1.1 :2.9. Separation of aqueous phase and an organic phase was observed in the collection vessel. Analysis of the upper, aqueous phase by NMR indicated approximately 8 mol percent of acrylic acid-TEA salt and approximately 92 mol percent TEA -HQ salt. Analysis of the lower, organic phase by NMR indicated approximately 51 mol percent 4- acryloxybenzophenone (ABP), approximately 0.01 mol percent BP and approximately 42 mol percent of the above mentioned TEA salts. Analysis of the organic layer by GC indicated 95percent Composition of ABP and 2percent of unreacted alcohol. After analysis, the organic layer was washed with water to remove salts and residual TEA. For EX-2 through EX-17, the same procedure was followed but with syringe contents and flow rates as indicated in Table 3. Blend compositions, flow rates, molar flow ratios of BP:ACL:TEA, and percent Composition are provided in Table 3.
	With triethylamine; sodium hydroxide; In water; ethyl acetate;	For EX-1, the following procedure was carried out using the microreactor described above, with the mixing device at ambient temperature. Container I contained 100 g BP, 50 g TEA, 20 G NaOH, and 147 g water. Container II contained 40 g ACl and 80 g EtOAc. Each container was connected to a pump and the pump speeds were controlled to deliver the mixtures in the containers at the following rates: Container I; 14 mL/min, or 0.022 mol/min of BP; Container II: 7 mL/min, or 0.028 mol/min of ACl. The two unused addition ports of the mixing device were sealed with plugs. The molar flow ratios of BP:NaOH:TEA:ACl pumped to the mixing device were approximately 1 : 1 : 1 : 1.24. Separation of aqueous phase and an organic phase was observed in the collection vessel. The organic phase was observed to have a hazy appearance. The aqueous layer was removed from the collection vessel. Results of analysis of the organic layer by GC and NMR are presented in Table 1.

Reference： [1]Journal of Photochemistry and Photobiology A: Chemistry,2011,vol. 219,p. 26 - 31
[2]Patent: WO2017/147040,2017,A1 .Location in patent: Page/Page column 23-24
[3]Patent: WO2018/231610,2018,A1 .Location in patent: Page/Page column 30

10
[ 1137-42-4 ]
[ 920-46-7 ]
[ 22535-49-5 ]

Yield	Reaction Conditions	Operation in experiment
	In water; butanone;	Synthesis of 4-acryloyloxy-benzophenone 1.3 g (16.25 mmoli) of NaOH 50percent water solution, were added to a solution of 3 g (15.21 mmol) of 4-hydroxybenzophenone in 20 cc of methyl ethyl ketone. After 30 minutes under stirring, a solution of 1.59 g (15.21 mmol) of methacryloyl chloride in 5 mL of methyl ethyl ketone were added dropwise. After the addition the reaction mixture was stirred for 1 hour, filtered and the solvent was evaporated. The oil residue was purified by flash chromatography on silica gel (eluent CH2Cl2) to obtain 2.74 g of a colourless liquid. 1HNMR (CDCl3): delta (ppm): 2.10 (s, 3H); 5.82 (s, 1H); 6.40 (s, 1H); 7.2-7.3 (m, 2H); 7.45-7.55 (m, 2H); 7.60-7.65 (m, 1H); 7.75-7.85 (m, 2H); 7.85-7.95 (m, 2H)

Reference： [1]Patent: US2015/175830,2015,A1 .Location in patent: Page/Page column

11
[ 625-36-5 ]
[ 1137-42-4 ]
[ 22535-49-5 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In dichloromethane; water;Flow reactor;	General procedure: EX-22 was carried out using Microreactor B. For EX-22, syringe I contained 15 g BP, 33 g TEA, and 33 g water. Syringe II contained 4.2 g 3CPC and 20 g DCM. Each syringe was placed in a separate syringe pump and the pump speeds were controlled to deliver the blends at the flow rates indicated for EX-22 in Table 8 below. The two unused addition ports of the mixing device were sealed with plugs. Separation of aqueous phase and an organic phase was observed in the collection vessel. Analysis of the upper, aqueous phase by NMR indicated approximately 8 mol percent of acrylic acid-TEA salt and approximately 92 mol percent TEA-HC1 salt. Analysis of the lower, organic phase by NMR indicated approximately 51 mol percent ABP, approximately 0.01 mol percent BP and approximately 42 mol percent of the above mentioned TEA salts. Analysis by GC indicated the organic layer was 98percent ABP and 2percent unreacted alcohol. After analysis, the organic layer was washed with water to remove salts and residual TEA. For EX-23 through EX-26, the same procedure was followed as described for EX-22, except that flow rates were as indicated in Table 8. Blend compositions, flow rates, and percent Composition are provided in Table 8.

Reference： [1]Patent: WO2017/147040,2017,A1 .Location in patent: Page/Page column 26

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Technical Information

? Baeyer-Villiger Oxidation ? Barbier Coupling Reaction ? Baylis-Hillman Reaction ? Benzylic Oxidation ? Birch Reduction ? Blanc Chloromethylation ? Bucherer-Bergs Reaction ? Clemmensen Reduction ? Corey-Bakshi-Shibata (CBS) Reduction ? Corey-Chaykovsky Reaction ? Fischer Indole Synthesis ? Friedel-Crafts Reaction ? Grignard Reaction ? Henry Nitroaldol Reaction ? Horner-Wadsworth-Emmons Reaction ? Hydride Reductions ? Hydrogenolysis of Benzyl Ether ? Lawesson's Reagent ? Leuckart-Wallach Reaction ? McMurry Coupling ? Meerwein-Ponndorf-Verley Reduction ? Passerini Reaction ? Paternò-Büchi Reaction ? Petasis Reaction ? Peterson Olefination ? Pictet-Spengler Tetrahydroisoquinoline Synthesis ? Preparation of Aldehydes and Ketones ? Preparation of Alkylbenzene ? Preparation of Amines ? Prins Reaction ? Reactions of Aldehydes and Ketones ? Reactions of Amines ? Reactions of Benzene and Substituted Benzenes ? Reformatsky Reaction ? Robinson Annulation ? Schlosser Modification of the Wittig Reaction ? Schmidt Reaction ? Specialized Acylation Reagents-Ketenes ? Stobbe Condensation ? Tebbe Olefination ? Ugi Reaction ? Vilsmeier-Haack Reaction ? Wittig Reaction ? Wolff-Kishner Reduction

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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. 1137-42-4 ] {[proInfo.proName]}

Quality Control of [ 1137-42-4 ]

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[ 1137-42-4 ] Synthesis Path-Upstream 1~1

[ 1137-42-4 ] Synthesis Path-Downstream 1~11

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Ketones

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[ 1137-42-4 ]