Home Cart 0 Sign in  
X

[ CAS No. 65145-13-3 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
3d Animation Molecule Structure of 65145-13-3
Chemical Structure| 65145-13-3
Chemical Structure| 65145-13-3
Structure of 65145-13-3 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Quality Control of [ 65145-13-3 ]

Related Doc. of [ 65145-13-3 ]

Alternatived Products of [ 65145-13-3 ]
Product Citations

Product Details of [ 65145-13-3 ]

CAS No. :65145-13-3 MDL No. :MFCD01310985
Formula : C7H5FO3 Boiling Point : -
Linear Structure Formula :- InChI Key :NXWTWYULZRDBSA-UHFFFAOYSA-N
M.W : 156.11 Pubchem ID :2783398
Synonyms :

Safety of [ 65145-13-3 ]

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 [ 65145-13-3 ]

* 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.

  • Upstream synthesis route of [ 65145-13-3 ]
  • Downstream synthetic route of [ 65145-13-3 ]

[ 65145-13-3 ] Synthesis Path-Upstream   1~20

  • 1
  • [ 1583-58-0 ]
  • [ 345-29-9 ]
  • [ 65145-13-3 ]
Reference: [1] Journal of Fluorine Chemistry, 2003, vol. 121, # 1, p. 97 - 99
  • 2
  • [ 74-83-9 ]
  • [ 65145-13-3 ]
  • [ 394-42-3 ]
Reference: [1] Molecular Crystals and Liquid Crystals (1969-1991), 1981, vol. 67, p. 1 - 24
  • 3
  • [ 82380-18-5 ]
  • [ 65145-13-3 ]
YieldReaction ConditionsOperation in experiment
100%
Stage #1: With sodium hydroxide In water for 4 h; Heating / reflux
Stage #2: With hydrogenchloride In water at 20℃;
To a stirred solution of 2-fluoro-4-hydroxybenzonitrile (20.00 g, 145.9 mmol) in 160 mL of water, was added 50percent aqueous sodium hydroxide (40.00 g, 500.0 mmol).
The mixture was heated to reflux for 4 hours, cooled to room temperature, poured into iced concentrated hydrochloric acid, and extracted with ether.
The product was extracted into saturated aqueous sodium bicarbonate and the ether layer discarded.
This aqueous extract was acidified with concentrated hydrochloric acid and extracted with ether.
The organic extract was dried over magnesium sulfate, filtered, and evaporated to give a white solid (22.90 g) of 2-fluoro-4-hydroxybenzoic acid in 100percent yield. 1H NMR (300 MHz, CD3COCD3) δ (ppm): 9.80 (b, 1H), 7.87 (t, 1H), 6.77 (dd, 1H), 6.66 (dd, 1H).
19F-NMR (300 MHz, CD3COCD3) δ (ppm): -108.13 (s, decoupled).
Reference: [1] Patent: US2006/20146, 2006, A1, . Location in patent: Page/Page column 30
[2] Molecular Crystals and Liquid Crystals (1969-1991), 1981, vol. 67, p. 1 - 24
[3] Patent: US6369261, 2002, B1, . Location in patent: Page column 25
  • 4
  • [ 860296-15-7 ]
  • [ 65145-13-3 ]
Reference: [1] European Journal of Organic Chemistry, 2005, # 10, p. 2116 - 2123
  • 5
  • [ 860296-18-0 ]
  • [ 124-38-9 ]
  • [ 65145-13-3 ]
  • [ 67531-86-6 ]
Reference: [1] European Journal of Organic Chemistry, 2005, # 10, p. 2116 - 2123
  • 6
  • [ 126940-10-1 ]
  • [ 65145-13-3 ]
Reference: [1] European Journal of Organic Chemistry, 2005, # 10, p. 2116 - 2123
[2] European Journal of Organic Chemistry, 2005, # 10, p. 2116 - 2123
[3] European Journal of Organic Chemistry, 2005, # 10, p. 2116 - 2123
  • 7
  • [ 860296-13-5 ]
  • [ 65145-13-3 ]
Reference: [1] European Journal of Organic Chemistry, 2005, # 10, p. 2116 - 2123
  • 8
  • [ 394-42-3 ]
  • [ 65145-13-3 ]
Reference: [1] RSC Advances, 2016, vol. 6, # 38, p. 32319 - 32327
  • 9
  • [ 124-38-9 ]
  • [ 146746-69-2 ]
  • [ 65145-13-3 ]
Reference: [1] European Journal of Organic Chemistry, 2005, # 10, p. 2116 - 2123
  • 10
  • [ 372-20-3 ]
  • [ 65145-13-3 ]
Reference: [1] European Journal of Organic Chemistry, 2005, # 10, p. 2116 - 2123
[2] Molecular Crystals and Liquid Crystals (1969-1991), 1981, vol. 67, p. 1 - 24
  • 11
  • [ 146746-69-2 ]
  • [ 65145-13-3 ]
Reference: [1] European Journal of Organic Chemistry, 2005, # 10, p. 2116 - 2123
  • 12
  • [ 331-64-6 ]
  • [ 65145-13-3 ]
Reference: [1] RSC Advances, 2016, vol. 6, # 38, p. 32319 - 32327
  • 13
  • [ 121219-03-2 ]
  • [ 65145-13-3 ]
Reference: [1] Molecular Crystals and Liquid Crystals (1969-1991), 1981, vol. 67, p. 1 - 24
  • 14
  • [ 217978-01-3 ]
  • [ 65145-13-3 ]
Reference: [1] Molecular Crystals and Liquid Crystals, 2009, vol. 502, p. 258 - 271
  • 15
  • [ 1583-58-0 ]
  • [ 345-29-9 ]
  • [ 65145-13-3 ]
Reference: [1] Journal of Fluorine Chemistry, 2003, vol. 121, # 1, p. 97 - 99
  • 16
  • [ 860296-18-0 ]
  • [ 124-38-9 ]
  • [ 65145-13-3 ]
  • [ 67531-86-6 ]
Reference: [1] European Journal of Organic Chemistry, 2005, # 10, p. 2116 - 2123
  • 17
  • [ 65145-13-3 ]
  • [ 96740-92-0 ]
Reference: [1] Tetrahedron Letters, 1998, vol. 39, # 39, p. 7193 - 7196
[2] Patent: WO2013/105753, 2013, A1, . Location in patent: Paragraph 112; 113; 114; 115; 116
[3] ChemMedChem, 2013, vol. 8, # 5, p. 779 - 799
  • 18
  • [ 67-56-1 ]
  • [ 65145-13-3 ]
  • [ 197507-22-5 ]
YieldReaction ConditionsOperation in experiment
94% at 90℃; for 16 h; Reference Example 10; methyl 2-fluoro-4-hydroxybenzoate A solution of 2-fluoro-4-hydroxybenzoic acid (50.0 g) and concentrated sulfuric acid (10 mL) in methanol (700 mL) was stirred at 90°C for 16 hr with heating. The reaction solution was concentrated, and the resulting colorless crystals were washed with water, and dried to give the title compound (51 g, yield 94percent) as colorless crystals. 1H NMR (300 MHz, DMSO-d6) 5: 3.79 (3 H, s), 6.61 - 6.72 (2 H, m), 7. 73 - 7.79 (1 H, m), 10.80 (1 H, br).
94% at 90℃; for 16 h; Reference Example 14
methyl 2-fluoro-4-hydroxybenzoate
A solution of 2-fluoro-4-hydroxybenzoic acid (50.0 g) and concentrated sulfuric acid (10 mL) in methanol (700 mL) was stirred with heating at 90°C for 16 hr.
The reaction solution was concentrated, and the resulting colorless crystals were washed with water, and dried to give the title compound (51 g, yield 94percent) as colorless crystals.
1H NMR (300 MHz, DMSO-d6) δ: 3.79 (3 H, s), 6.61 - 6.72 (2 H, m), 7.73 - 7.79 (1H, m), 10.80 (1 H, br).
85% at 80℃; for 20.5 h; Intermediate T7T7.1[0341] Methyl 2-fluoro-4-hydroxybenzoate (T7.1). To a round bottom containing 2-fluoro-4-hydroxybenzoic acid (Commercially available from TCI America) (5.34 g, 34.19 mmol) was added a cold solution of MeOH (50 mL) and sulfuric acid (2.0 mL). The mixture was heated to 80cC and monitored with TLC. After 20.5 hours, the solvent was removed and the residue was diluted with diethyl ether. The organic phase was washed carefully two times with saturated aqueous NaHCO3, once with brine, and then dried over anhydrous sodium sulfate. After filtration, the organic solvent was removed in vacuo to yield T7.1 as a white solid (5.82, 85percent yield). 1H NMR (400 MHz, DMSOd6) 10.79 (1 H, s), 7.75 (1 H, t, J=8.8 Hz), 6.69 (1 H, dd, J=8.6, 2.3 Hz), 6.62 (1 H, dd, J=13.1, 2.2 Hz), 3.78 (3 H, s).
85% at 80℃; for 20.5 h; Methyl 2-fluoro-4-hydroxybenzoate (T22.1). To a round bottom containing 2-fluoro-4-hydroxybenzoic acid (5.34 g, 34.19 mmol) (commercially available from Matrix Scientific and TCI America) was added a cold solution of MeOH (50 mL) and sulfuric acid (2.0 mL). The mixture was heated to 80°C and monitored with TLC. After 20.5 hours, the solvent was removed, and the mixture was diluted with diethyl ether. The organic phase was washed carefully two times with saturated, aqueous NaHCO3, once with brine, and then dried over anhydrous sodium sulfate. After filtration, the organic solvent was removed in vacuo to yield T22.1 as a white solid (5.82, 85percent yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 10.79 (1 H, s), 7.75 (1 H, t, J=8.8 Hz), 6.69 (1 H, dd, J=8.6, 2.3 Hz), 6.62 (1 H, dd, J=13.1, 2.2 Hz), 3.78 (3 H, s).

Reference: [1] Patent: EP2392573, 2011, A1, . Location in patent: Page/Page column 39
[2] Patent: EP2522657, 2012, A1, . Location in patent: Page/Page column 36-37
[3] Patent: WO2010/45258, 2010, A2, . Location in patent: Page/Page column 140; 141
[4] Patent: WO2009/111056, 2009, A1, . Location in patent: Page/Page column 212
[5] ChemMedChem, 2013, vol. 8, # 5, p. 779 - 799
[6] Patent: EP2017263, 2009, A1, . Location in patent: Page/Page column 145-146
[7] RSC Advances, 2016, vol. 6, # 38, p. 32319 - 32327
  • 19
  • [ 65145-13-3 ]
  • [ 197507-22-5 ]
Reference: [1] Patent: US5990142, 1999, A,
  • 20
  • [ 65145-13-3 ]
  • [ 18107-18-1 ]
  • [ 197507-22-5 ]
Reference: [1] Patent: WO2007/3962, 2007, A2, . Location in patent: Page/Page column 22-23
Recommend Products
Same Skeleton Products
Historical Records

Related Functional Groups of
[ 65145-13-3 ]

Fluorinated Building Blocks

Chemical Structure| 51446-30-1

[ 51446-30-1 ]

2-Fluoro-5-hydroxybenzoic acid

Similarity: 0.98

Chemical Structure| 214917-68-7

[ 214917-68-7 ]

2,6-Difluoro-4-hydroxybenzoic acid

Similarity: 0.93

Chemical Structure| 67531-86-6

[ 67531-86-6 ]

2-Fluoro-6-hydroxybenzoic acid

Similarity: 0.91

Chemical Structure| 1084801-91-1

[ 1084801-91-1 ]

Methyl 2-fluoro-5-hydroxybenzoate

Similarity: 0.91

Chemical Structure| 128272-26-4

[ 128272-26-4 ]

Methyl 2-fluoro-4-methoxybenzoate

Similarity: 0.90

Aryls

Chemical Structure| 51446-30-1

[ 51446-30-1 ]

2-Fluoro-5-hydroxybenzoic acid

Similarity: 0.98

Chemical Structure| 214917-68-7

[ 214917-68-7 ]

2,6-Difluoro-4-hydroxybenzoic acid

Similarity: 0.93

Chemical Structure| 67531-86-6

[ 67531-86-6 ]

2-Fluoro-6-hydroxybenzoic acid

Similarity: 0.91

Chemical Structure| 1084801-91-1

[ 1084801-91-1 ]

Methyl 2-fluoro-5-hydroxybenzoate

Similarity: 0.91

Chemical Structure| 128272-26-4

[ 128272-26-4 ]

Methyl 2-fluoro-4-methoxybenzoate

Similarity: 0.90

Carboxylic Acids

Chemical Structure| 51446-30-1

[ 51446-30-1 ]

2-Fluoro-5-hydroxybenzoic acid

Similarity: 0.98

Chemical Structure| 214917-68-7

[ 214917-68-7 ]

2,6-Difluoro-4-hydroxybenzoic acid

Similarity: 0.93

Chemical Structure| 67531-86-6

[ 67531-86-6 ]

2-Fluoro-6-hydroxybenzoic acid

Similarity: 0.91

Chemical Structure| 887267-08-5

[ 887267-08-5 ]

3-Fluoro-5-hydroxy-4-methylbenzoic acid

Similarity: 0.89

Chemical Structure| 123843-65-2

[ 123843-65-2 ]

2,6-Difluoro-4-methoxybenzoic acid

Similarity: 0.87