[ CAS No. 2100-31-4 ] {[proInfo.proName]}

Name: 2100-31-4|2-Propoxybenzoic acid|97%
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Quality Control of [ 2100-31-4 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 2100-31-4 ]

Product Details of [ 2100-31-4 ]

CAS No. :	2100-31-4	MDL No. :	MFCD01075687
Formula :	C₁₀H₁₂O₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	OXOWWPXTTOCKKU-UHFFFAOYSA-N
M.W :	180.20	Pubchem ID :	539215
Synonyms :

Safety of [ 2100-31-4 ]

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 [ 2100-31-4 ]

* 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 [ 2100-31-4 ]
Downstream synthetic route of [ 2100-31-4 ]

[ 2100-31-4 ] Synthesis Path-Upstream 1~8

1
[ 92156-43-9 ]
[ 2100-31-4 ]

Yield	Reaction Conditions	Operation in experiment
95%	With potassium <i>tert</i>-butylate In dimethyl sulfoxide at 0 - 30℃;	EXAMPLE 2; To a solution of C (about 9 mmol) in DMSO, Potassium tertiary butoxide (about 11 mmol) isadded at a temperature of about 0°C. The reaction mixture is stirred at a temperature of about0°C and for a time-period of about 30 minutes, followed by stirring the reaction mixture at room temperature (RT) (of about 25°C-30°C) for 2-3 hours. The reaction upon completion isworked upon using ice cold water and then extracted with dichloromethane (DCM). Thecombined organic layer is dried over NaS04 and then evaporated. The crude product thusobtained is purified by recrystallization using ethanol as the solvent, to obtain 95 percent of thedesired product 2-Propoxy-benzoic Acid (D).
80%	Stage #1: With potassium <i>tert</i>-butylate In dimethyl sulfoxide at 70℃; for 2 h; Stage #2: With hydrogenchloride; water In dimethyl sulfoxide at 0 - 10℃;	To a stirred solution of Propyl 2-propoxy-benzoate (10 g, 240 mmol) in dimethyl sulfoxide (40 mL) was added potassium tert-butoxide (10 g, 890 mmol) in portions. The solution was heated to 70° C. on a water bath for 2 h, and the progress of the reaction was monitored by TLC using a hexane-ethyl acetate (8:2) solvent system. The reaction mass was cooled to 10° C., poured into ice water, and then acidified with 5percent dilute hydrochloric acid. The precipitated solid was filtered and washed thoroughly with distilled water, and the crude mass was recrystallized in hexane (50 mL) to yield an off-white solid of 2-Propoxy-benzoic Acid (7.6 g, 80percent).

Reference： [1] Patent: WO2013/160885, 2013, A1, . Location in patent: Page/Page column 16
[2] Patent: US2006/167107, 2006, A1, . Location in patent: Page/Page column 4

2
[ 59086-52-1 ]
[ 2100-31-4 ]

Reference： [1] Synthetic Communications, 2012, vol. 42, # 6, p. 893 - 904

3
[ 18167-33-4 ]
[ 2100-31-4 ]

Reference： [1] Journal of the American Chemical Society, 1942, vol. 64, p. 1691,1692
[2] Journal of the Chemical Society, 1944, p. 19
[3] Journal of Medicinal Chemistry, 1993, vol. 36, # 10, p. 1387 - 1392

4
[ 856306-04-2 ]
[ 2100-31-4 ]

Reference： [1] Journal of the American Chemical Society, 1942, vol. 64, p. 1691,1692
[2] Journal of the Chemical Society, 1944, p. 19

5
[ 69-72-7 ]
[ 2100-31-4 ]

Reference： [1] Patent: WO2013/160885, 2013, A1,

6
[ 118-61-6 ]
[ 2100-31-4 ]

Reference： [1] Journal of the Chemical Society, 1944, p. 19

7
[ 107-08-4 ]
[ 69-72-7 ]
[ 2100-31-4 ]

Reference： [1] Oef. Fi., vol. 30, p. 57

8
[ 2100-31-4 ]
[ 139756-02-8 ]
[ 139756-04-0 ]

Yield	Reaction Conditions	Operation in experiment
92%	Stage #1: With thionyl chloride In dichloromethane for 3 h; Heating / reflux Stage #2: With dmap; triethylamine In dichloromethane at 0℃; for 1 h;	Step 8 2-Methyl-4-(2-propoxybenzoylamino)-5-propyl-2H-pyrazole-3-carboxamide: A solution of 2-propoxybenzoic acid (13.7 g, 76.1 mmol) and thionyl chloride (36.2 g, 304.4 mmol) in dry dichloromethane (80 mL) was heated for 3 hours at reflux. The solvent and excess thionyl chloride were distilled off under reduced pressure. The residue was taken up in dry dichloromethane (60 mL) and reacted with a solution of 4-amino-2-methyl-5-propyl-2H-pyrazole-3-carboxamide (12.6 g, 69.2 mmol), dry triethylamine (7 g, 69.2 mmol) and 4-(N,N-dimethylamino)pyridine (84.5 mg, 0.7 mmol) in dry dichloromethane (200 mL) at 0° C. Stirring was maintained for 1 hour, and the reaction mixture was successively washed with water (150 mL), saturated aqueous sodium carbonate solution (200 mL) and saturated brine (200 mL). The organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated to about 60 mL, and then hexane (150 mL) was added to give precipitate product as a white solid (22 g, 92percent). ¹H NMR (300 MHz, CDCl₃) δ 9.47 (s, 1H), 8.28 (d, 1H, J=7.8 Hz), 7.87 (br.s, 1H), 7.57-7.52 (m, 1H), 7.16-7.05 (m, 2H), 5.53 (s, 1H), 4.20 (t, 2H, J=6.6 Hz), 4.09 (s, 3H), 2.54 (t, 2H, J=7.5 Hz), 1.97-1.85 (m, 2H), 1.69-1.26 (m, 2H), 1.07 (t, 3H, J=7.2 Hz), 0.95 (t, 3H, J=7.5 Hz). LC-MS: m/z=345 (M+H)⁺

Reference： [1] Patent: US2008/194529, 2008, A1, . Location in patent: Page/Page column 57-58
[2] Patent: US2003/176696, 2003, A1,

[ 2100-31-4 ] Synthesis Path-Downstream 1~61

1
[ 18167-33-4 ]
[ 2100-31-4 ]

Reference： [1]Journal of the American Chemical Society,1942,vol. 64,p. 1691,1692
[2]Journal of the Chemical Society,1944,p. 19
[3]Journal of Medicinal Chemistry,1993,vol. 36,p. 1387 - 1392

2
[ 2100-31-4 ]
[ 54090-36-7 ]

Yield	Reaction Conditions	Operation in experiment
	With thionyl chloride;N,N-dimethyl-formamide; In hexane; for 1h;Heating / reflux;	To a stirred solution of 2-Propoxy-benzoic Acid (6.5 g, 16 mmol) in hexane (60 mL) were added thionyl chloride (2.5 g, 21 mmol) and N,N-dimethylformamide (0.5 mL). The reaction mixture was heated to reflux for 1 h. After the reaction was complete, the solvent was evaporated under reduced pressure to yield the desired 2-Propoxy-6-pentadecylbenzoyl Chloride, which was redissolved in dichloromethane (50 mL) and used for the condensation with anilides.
	With thionyl chloride; In dichloromethane; N,N-dimethyl-formamide; for 2h;Cooling with ice; Reflux;	EXAMPLE 2; A solution of D (about 3.3 mmol) in 10 ml DCM is cooled in ice. To the cooled solution,thionyl chloride (SOCb) (about 3.66 mmol) is added dropwise. To the reaction mixture, fewdrops of DMF is also added. The reaction mixture is refluxed for about 2 hours. The reactionupon completion is evaporated in vacuum to obtain crude product 2-Propoxy-benzoyl chloride(E). To this crude product dissolved in DCM, 5-amino-2-chlorobenzotriflouride (about 3.3mmol) is added. The reaction mixture is refluxed for about 3-4 hours. The reaction uponcompletion is worked upon using water and DCM. The combined organic extract is evaporatedin vacuum to yield crude product which is purified using recrystallization to yield the pureproduct COMPOUND 1 (TTK21) (92% yield).
	With thionyl chloride; In dichloromethane; at 100℃; for 0.5h;Cooling with ice;	1) 2-propoxy, benzoyl chloride preparation: the 1mol2-propoxy benzoic acid is dissolved in methylene chloride, the 2-propoxy benzoic acid concentration is 100mol/L, under cooling conditions ice bath slowly dropping 1.2mol thionyl chloride, after dripping, 100 C reflux reaction under 30 minutes, methylene chloride is removed by reduced pressure distillation, to obtain intermediate 2-propoxy, benzoyl chloride, does not need to be purified, directly follow-up reaction;

Reference： [1]Journal of the Chemical Society,1910,vol. 97,p. 1747
[2]Patent: US2006/167107,2006,A1 .Location in patent: Page/Page column 4
[3]Patent: WO2013/160885,2013,A1 .Location in patent: Page/Page column 16
[4]Patent: CN103755709,2016,B .Location in patent: Paragraph 0071

3
[ 856306-04-2 ]
[ 2100-31-4 ]

Reference： [1]Journal of the American Chemical Society,1942,vol. 64,p. 1691,1692
[2]Journal of the Chemical Society,1944,p. 19

4
[ 107-08-4 ]
[ 69-72-7 ]
[ 2100-31-4 ]

Reference： [1],vol. 30,p. 57

5
[ 452-58-4 ]
[ 2100-31-4 ]
2-(2-propoxyphenyl)-1H-imidazo<4,5-b>pyridine [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1993,vol. 36,p. 1387 - 1392

6
[ 2100-31-4 ]
[ 13736-91-9 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1966,vol. 23,p. 2196 - 2201

Yield	Reaction Conditions	Operation in experiment
		C. 2-Propoxybenzoic Acid 1 H NMR (400 MHz, CDCl3) delta:8.19 (1H, dd, J=1.8, 8.0 Hz), 7.55 (1H, apparent t, J=8.0 Hz), 7.13 (1H, t, J=7.5 Hz), 7.05 (1H, d, J=7.5 Hz), 4.23 (2H, t, J=6.6 Hz), 1.96 (2H, m), 1.11 (3H, t, J=7.4 Hz).

8
[ 2100-31-4 ]
[ 78033-18-8 ]
[ 503809-60-7 ]