[ CAS No. 7307-03-1 ] {[proInfo.proName]}

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Quality Control of [ 7307-03-1 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 7307-03-1 ]

CAS No. :	7307-03-1	MDL No. :	MFCD00511093
Formula :	C₇H₁₂O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	-
M.W :	128.17	Pubchem ID :	-
Synonyms :

Safety of [ 7307-03-1 ]

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 [ 7307-03-1 ]

* 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.

Downstream synthetic route of [ 7307-03-1 ]

[ 7307-03-1 ] Synthesis Path-Downstream 1~9

1
[ 7307-03-1 ]
[ 91724-94-6 ]

Yield	Reaction Conditions	Operation in experiment
74%	With hydrazine hydrate In ethanol RT, 20 min., then reflux, 10 min.;
	With hydrazine hydrate In ethanol
	With hydrazine hydrate In ethanol at 0 - 20℃; for 1h;

Reference： [1]Suzuki, M.; Watanabe, A.; Noyori, R. [Recueil des Travaux Chimiques des Pays-Bas, 1988, vol. 107, # 3, p. 230 - 236]
[2]Fukuda, Takeshi; Goto, Riki; Kiho, Toshihiro; Ueda, Kenjiro; Muramatsu, Sumie; Hashimoto, Masami; Aki, Anri; Watanabe, Kengo; Tanaka, Naoki [Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 16, p. 3716 - 3722]
[3]Di Fruscia, Paolo; Carbone, Anna; Bottegoni, Giovanni; Berti, Francesco; Giacomina, Francesca; Ponzano, Stefano; Pagliuca, Chiara; Fiasella, Annalisa; Pizzirani, Daniela; Ortega, Jose Antonio; Nuzzi, Andrea; Tarozzo, Glauco; Mengatto, Luisa; Giampà, Roberta; Penna, Ilaria; Russo, Debora; Romeo, Elisa; Summa, Maria; Bertorelli, Rosalia; Armirotti, Andrea; Bertozzi, Sine Mandrup; Reggiani, Angelo; Bandiera, Tiziano; Bertozzi, Fabio [Journal of Medicinal Chemistry, 2021, vol. 64, # 18, p. 13327 - 13355]

2
[ 13114-87-9 ]
[ 105-07-7 ]
[ 7307-03-1 ]
[ 671776-48-0 ]

Yield	Reaction Conditions	Operation in experiment
14%	With ethyl phosphate; In tetrahydrofuran; for 18h;Heating / reflux;	Example 33A; 4- {5-Isobutyryl-6-methyl-2-oxo-l- [3- (trifluoromethyl) phenyl]-1, 2,3, 4-tetrahydropyrimidin-4-yl}- benzonitrile; To a stirred solution of N-[3-(trifluoromethyl) phenyl] urea (6.37 g, 31.2 mmol), 4-cyanobenz- aldehyde (4.09 g, 31.2 mmol) and 5-methylhexane-2,4-dione (4.0 g, 31.2 mmol) in tetrahydrofuran (150 ml) is added ethyl polyphosphonate (12 g). The mixture is stirred at reflux for 18 hours. After cooling down to room temperature, the solvent is removed in vacuo and the residue is purified by column chromatography on silica with cyclohexane/ethyl acetate as eluent. Yield: 1.91 g (14% of th.) 'H-NMR (300 MHz, DMSO-d6): 8 = 8.37 (d, 1H), 7.92-7. 52 (m, 8H), 5.47 (m, 1H), 2.95 (m, 1H), 1. 86 (s, 3H), 0.95 (d, 3H), 0. 81 (d, 3H) ppm.

Reference： [1]Patent: WO2005/82863,2005,A2 .Location in patent: Page/Page column 53

3
[ 563-80-4 ]
[ 141-78-6 ]
[ 7307-03-1 ]

Yield	Reaction Conditions	Operation in experiment
62%	With sodium hydride In di-isopropyl ether; mineral oil at 50℃; for 2.5h;	I.ii (ii) Synthesis of Using NaH as Base A 1 L-three neck flask was charged with 150 mL of a diisopropyl ether, 36.2 g (40.2 mL) of ethyl acetate and 17.1 g of NaH (55% oil dispersion). The mixture was maintained at 50° C. with stirring, and thereto was added 20.1 g (25.0 mL) of 3-methyl-2-butanone with a dropping funnel over 1 hour. The reaction solution was reacted at 50° C. for 1.5 hours. (0051) After completion of the reaction, 5 mL of ethanol was added and stirred, and unreacted NaH was treated to be removed. Then, in the same manner as a use of the above NaNH2 as a base, a salt in the reaction solution was dissolved into water, and extracted and washed, and the organic layer (β-diketone compound) generated and separated by conducting a pH operation was recovered. The β-diketone compound synthesized herein was assumed to be No. 5.
35%	With potassium <i>tert</i>-butylate In tetrahydrofuran at 60℃; for 4h;	36 A mixture of 3-methylbutan-2-one (5.0 g, 58 mmol) and EtOAc (5.35 g, 175 mmol) in THF (50 mL) was added dropwise to a solution of t-BuOK (9.75 g, 87 mmol) in THF (130 mL) at 60 C. After addition, the reaction mixture was stirred at 60 C for 4 h, cooled to RT and quenched with HCl (2M, 60 mL). The aqueous layer was separated, extracted with EtOAc (50 mL x 3) and the combined organic phases were dried over anhydrous Na2SO4 and filtered. The filtrate was concentrated in vacuo, and the residue was purified by silica gel chromatography (PE/EA = 10 : 1) to give 5-methylhexane-2,4-dione (2.6 g, 35%) as a yellow oil.
26%	Stage #1: 3-methyl-butan-2-one With potassium <i>tert</i>-butylate for 0.5h; Stage #2: ethyl acetate at 55℃; for 12h;	1.A 1A. Preparation of 5-methylhexane-2,4-dione [0139] Tert-BuOK (20 g, 178 mmol, 1.5 eq) was added in portions to 3,3-dimethylbutan- 2-one(10 g, 119 mmol, 1.0 eq) and stirred for 30min. Then ethyl acetate (35 mL, 357 mmol, 3.0 eq) was added dropwise at 55 °C. The solution was stirred at 55 °C for 12h. TLC analysis (petroleum ether/EtOAc = 1 : 1) showed the reaction was completed. Then the solution was poured over ice/hydrochloric acid and extracted with EtOAc (2x100 mL). The organic layer was then washed with 4M hydrochloric acid (2x30 mL) and brine (30 mL). The crude product was purified by column chromatography to give 5-methylhexane-2,4- dione (4.0 g, yield: 26%).LC/MS: m/z(M++l) = 129.

With potassium <i>tert</i>-butylate In tetrahydrofuran at 20 - 60℃; Inert atmosphere;

22 Preparation 22; 5-Methylhexane-2,4-dione; A mixture of 3-methyl-2-butanone (3.57 mL, 33.3 mmol) and ethyl acetate (9.8 mL, 99.9 mmol) in THF (30 mL) was added dropwise to a stirring solution of potassium tert-butoxide (50 mL of a 1N solution in THF, 50 mmol) in THF (100 mL) at 60° C. under nitrogen. The mixture was stirred at this temperature for 3 hours and then cooled to room temperature and stirred for a further 16 hours. Dilute hydrochloric acid (30 mL of a 2N solution) was added and the mixture was extracted with diethylether (3×20 mL). The combined organic fractions were washed with brine, dried (MgSO4) and the solvent was removed in vacuo. The residue was chromatographed on silica gel using 98:2 pentane:ether as eluant to afford the title compound as a yellow oil, 2.83 g.LRMS: m/z APCI 129 [MH]+

Reference： [1]Current Patent Assignee: TANAKA HOLDINGS CO.,LTD. - US2015/291497, 2015, A1 Location in patent: Paragraph 0049-0051
[2]Current Patent Assignee: BIAL R D INVESTMENTS - WO2016/73889, 2016, A1 Location in patent: Paragraph 00275
[3]Current Patent Assignee: PHARMARESOURCES SHANGHAI CO LTD - WO2013/6792, 2013, A1 Location in patent: Paragraph 0139
[4]Current Patent Assignee: PFIZER INC - US2009/209578, 2009, A1 Location in patent: Page/Page column 24

4
[ 13114-87-9 ]
[ 105-07-7 ]
[ 7307-03-1 ]
[ 1000588-65-7 ]
4-{(4S)-5-isobutyryl-6-methyl-2-oxo-1-[3-(trifluoromethyl)phenyl]-1,2,3,4-tetrahydropyrimidin-4-yl}benzonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
8%		Method 15 (Preparative HPLC):Instrument: Abimed Gilson Pump 305/306, Manometric Module 806; column: GromSil 120 ODS-4HE, 10 mum, 250 mm×30 mm; eluent A: water, eluent B: acetonitrile; gradient: 0.0 min 30% B?3 min 30% B?31 min 95% B?44 min 95% B?45 min 30% B; flow rate: 50 ml/min; column temperature: RT; UV detection: 210 nm.; Example 24-{(4R)-5-Isobutyryl-6-methyl-2-oxo-1-[3-(trifluoromethyl)phenyl]-1,2,3,4-tetrahydropyrimidin-4-yl}benzonitrile 2000 mg (15.604 mmol) of 5-methylhexane-2,4-dione, 2046 mg (15.604 mmol) of 4-formyl-benzonitrile and 3186 mg (15.604 mmol) of <strong>[13114-87-9]1-[3-(trifluoromethyl)phenyl]urea</strong> are dissolved in 60 ml of THF, and 10 g of ethyl polyphosphate (PPE) are added. The mixture is stirred at 80 C. overnight and then partitioned between water and ethyl acetate. The organic phase is separated off, dried over sodium sulfate and filtered, and the solvent is stripped off in a rotary evaporator. The residue is purified firstly by flash chromatography on silica gel (eluent: cyclohexane/ethyl acetate 1:1) and then by preparative HPLC on a chiral phase (method 18), thus separating the enantiomers (desired enantiomer: Rt=4.70 min). Further purification by preparative HPLC (method 15) results in 530 mg (8% of theory) of the title compound.MS (ESIpos): m/z (%)=428 (100) [M+H]+ HPLC (method 3): Rt=8.33 min1H-NMR (400 MHz, DMSO-d6): delta=0.80 (d, 3H), 0.95 (d, 3H), 1.86 (s, 3H), 2.95 (tt, 1H), 5.48 (d, 1H), 7.55 (d, 1H), 7.62 (d, 2H), 7.68 (t, 1H), 7.70 (s, 1H), 7.77 (d, 1H), 7.89 (d, 2H), 8.41 (d, 1H).

Reference： [1]Patent: US2010/10024,2010,A1 .Location in patent: Page/Page column 13; 15

5
[ 529-23-7 ]
[ 7307-03-1 ]
C₁₄H₁₅NO [ No CAS ]
C₁₄H₁₅NO [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	Stage #1: o-aminobenzaldehyde; 5-methylhexane-2,4-dione With lanthanide(III)chloride heptahydrate; acetic acid at 60℃; Stage #2: With sodium hydroxide In water; ethyl acetate at 20℃; regioselective reaction;	14. A typical experimental procedure. General procedure: To a reaction vial loaded with substituted 1,3-diketone (0.24 mmol), amino benzaldehyde, (0.2 mmol) and lanthanum chloride heptahydrate was added acetic acid (3.5 mL). The resulting suspension was heated to 60 °C for 3-5 h. The reaction progress was monitored by LC-MS. At the completion, the reaction mixture was allowed to cool to room temperature. Ethyl acetate (5 mL) was added and the resulting mixture was washed with water (5 mL) and 1 N NaOH (5 mL), the organic layer was dried on MgSO4 and concentrated to give a crude product. The major quinoline product was isolated by column chromatography.

Reference： [1]Location in patent: experimental part Chen, Ying; Huang, Jinkun; Hwang, Tsang-Lin; Li; Cui, Sheng; Chan, Johann; Bio, Matthew [Tetrahedron Letters, 2012, vol. 53, # 26, p. 3237 - 3241]

6
[ 105-36-2 ]
[ 7307-03-1 ]
[ 1417556-98-9 ]

Yield	Reaction Conditions	Operation in experiment
75%	Stage #1: 5-methylhexane-2,4-dione With potassium hydroxide In 1,4-dioxane; water at 0 - 20℃; for 0.5h; Stage #2: ethyl bromoacetate In 1,4-dioxane; water at 0 - 20℃; for 12h;	1.B IB. Preparation of ethyl 3-acetyl-5-methyl-4-oxohexanoate [0140] To a solution of 5-methylhexane-2,4-dione(2 g, 10.7 mmol, 1.0 eq) in dioxane (20 mL) and H20 (10 mL) was added KOH (0.6 g, 10.7 mmol, 1.0 eq) in portions at 0 °C. The mixture was stirred at room temperature for 30 minutes. To the resulting mixture was added ethyl 2-bromoacetate (1.77 g, 10.7 mmol, 1 eq) dropwise at 0 °C, and the mixture was stirred at room temperature for 12 hours. TLC (petroleum ether/EtOAc = 1 :1) showed the reaction was completed. The reaction mixture was extracted with EtOAc (2x50 mL). The combined organic extracts were washed with brine (3x20 mL), dried over Na2S04 and concentrated in vacuum to give crude product, which was purified by column chromatography on silica gel to give compound ethyl 3-acetyl-5-methyl-4-oxohexanoate (1.5 g, yield: 75%). LC/MS: m/z (M++l) = 215.

Reference： [1]Current Patent Assignee: PHARMARESOURCES SHANGHAI CO LTD - WO2013/6792, 2013, A1 Location in patent: Paragraph 0140

7
[ 21190-16-9 ]
[ 7307-03-1 ]
ethyl 2-isopropyl-4-methylimidazolo[1,5-a]pyrimidine-8-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With acetic acid; at 100℃; for 6h;	To a stirred solution of 5-methylhexane-2,4-dione (3.1 g, 20 mmol) in AcOH (40 mL) was added <strong>[21190-16-9]ethyl 5-amino-1H-imidazole-4-carboxylate</strong> (1.9 g, 24 mmol). The reaction mixture was stirred at 100 C for 6 hours and concentrated in vacuo. The residue was purified by silica gel column (DCM/MeOH: 1/0 to 10/1) to give ethyl 2-isopropyl-4- methylimidazolo[1,5-a]pyrimidine-8-carboxylate (1.2 g, 40%) as a yellow solid. LC-MS m/z: 248.1 [M+H]+. LC-MS Purity (214 nm): > 80%; tR = 1.63 min.

Reference： [1]Patent: WO2016/73889,2016,A1 .Location in patent: Paragraph 00276

8
iridium(III) chloride trihydrate [ No CAS ]
[ 298-14-6 ]
[ 7307-03-1 ]
C₁₄H₂₂Cl₂IrO₄^(1-)*K⁽¹⁺⁾ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
16%		40.6 g (115 mmol) of iridium trichloride trihydrate,And 530 ml of pure water were placed in a three-necked flask and dissolved,Subsequently, 45.7 g (357 mmol) of 5-methyl-2,4-hexanedione was added and reacted at 95 C. for 1 hour,47.5 g (475 mmol) of <strong>[298-14-6]potassium hydrogen carbonate</strong> was added little by little to adjust the pH to about 8.Further, the reaction was carried out by heating for 5 hours.After the reaction overnight, unreacted 5-methyl-2,4-hexanedione was extracted and removed from the supernatant aqueous layer using hexane,Subsequently, the iridium compound (Ir-17) was extracted with ethyl acetate, and the extract was concentrated to dryness to obtain 12 g of crude crystals of an orange iridium compound (Ir-17).Further, the crude crystals were purified by column to obtain 10.2 g of orange iridium compound (Ir-17) crystal. The isolated yield was 16%.
16%	In water; at 95℃; for 6h;pH 8.0;	40.6 g (115 mmol) of iridium trihydrate trihydrate and 530 ml of pure water were placed in a three-necked flask and dissolved,Subsequently, 45.7 g of 5-methyl-2,4-hexanedione(357 mmol) were added and reacted at 95 C. for 1 hour,Thereto, 47.5 g of <strong>[298-14-6]potassium hydrogen carbonate</strong>(475 mmol) was added little by little,The pH was adjusted to about 8.Further, the reaction was carried out by heating for 5 hours.After reacting overnight, from the supernatant aqueous layer,Unreacted 5-methyl-2,4-hexanedione was extracted and removed with hexane,Subsequently, the iridium compound (Ir-2) was extracted with ethyl acetate,The extract was concentrated to dryness to obtain 12 g of crude crystals of orange iridium compound (Ir-2).The crude crystals were purified by column to obtain 10.2 g of an orange iridium compound (Ir-2) crystal. The isolated yield was 16%.

Reference： [1]Patent: JP2017/226633,2017,A .Location in patent: Paragraph 0075
[2]Patent: JP2017/226634,2017,A .Location in patent: Paragraph 0082

9
[ 2243274-79-3 ]
[ 7307-03-1 ]
[ 2243276-62-0 ]

Yield	Reaction Conditions	Operation in experiment
78%	Stage #1: 5-methylhexane-2,4-dione With sodium ethanolate In ethanol at 20℃; for 0.166667h; Stage #2: 4-(bromomethyl)-2-chloro-7,7-dimethylbenzenesulfonamide With potassium iodide In ethanol at 20℃; for 10h;	42.AAAAI Preparation of 4-(2-acetyl-4-methyl-3-oxopentyl)-2-chloro-N,N-dimethylbenzenesulfonamide To a stirring solution of 5-methylhexane-2, 4-dione (1.99 mL, 14.39 mmol) in ethanol (15.0 mL) at rt was added sodium ethoxide (21 w % in ethanol; 1.71 mL, 5.27 mmol). After stirring for 10 min, potassium iodide (797 mg, 4.79 mmol) was added followed by 4- (bromomethyl)-2-chloro-N,N-dimethylbenzenesulfonamiode (1.5 g, 4.79 mmol). The resulting mixture was stirred at rt for 10 h. The reaction mixture was concentrated under reduced pressure. The residue was diluted with ethyl acetate (200 mL) and washed with water (50 mL), brine (50 mL) dried over Na2S04 and then concentrated in vacuo. The crude material was purified over silica gel, eluting with 15% ethyl acetate in hexane to afford 4-(2-acetyl-4-methyl-3-oxopentyl)-2- chloro-N,N-dimethylbenzenesulfonamide (1.34 g, 78%) as a colorless gum. -NM (400 MHz, DMSO- ) δ ppm: 7.82 (d, J = 8.0 Hz, 1 H), 7.58 (d, J = 1.6 Hz, 1 H), 7.36 - 7.38 (m, 1 H), 4.58 (t, J= 8.0 Hz, 1 H), 3.12-3.00 (m, 2 H), 2.76 (s, 6 H), 2.76-2.65 (m, 1 H), 2.16 (s, 3 H), 0.97 (d, J = 6.4 Hz, 3 H), 0.79 (d, J= 6.4 Hz, 3 H).

Reference： [1]Current Patent Assignee: PHARMAXIS LTD - WO2018/157190, 2018, A1 Location in patent: Paragraph 0381

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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

[ CAS No. 7307-03-1 ] {[proInfo.proName]}

Quality Control of [ 7307-03-1 ]

Related Doc. of [ 7307-03-1 ]

Product Details of [ 7307-03-1 ]

Safety of [ 7307-03-1 ]

Application In Synthesis of [ 7307-03-1 ]

[ 7307-03-1 ] Synthesis Path-Downstream 1~9

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry