[ CAS No. 623-47-2 ]

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2D
Chemical Structure| 623-47-2
Chemical Structure| 623-47-2
Structure of 623-47-2

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Product Details

CAS No. :623-47-2MDL No. :MFCD00009184
Formula :C5H6O2InChI Key :FMVJYQGSRWVMQV-UHFFFAOYSA-N
M.W :98.10Pubchem ID :12182
Boiling Point :120°C at 760 mmHg
Synonyms :

Computed Properties

TPSA : 26.3 H-Bond Acceptor Count : 2
XLogP3 : 1 H-Bond Donor Count : 0
SP3 : 0.40 Rotatable Bond Count : 2

Safety

Signal Word:DangerClass3
Precautionary Statements:P261-P305+P351+P338UN#:3272
Hazard Statements:H226-H315-H319-H335Packing Group:
GHS Pictogram:

Application In Synthesis

  • Upstream synthesis route

[ 623-47-2 ] Synthesis Path-Upstream   1~11

  • 1
  • [ 64-17-5 ]
  • [ 471-25-0 ]
  • [ 623-47-2 ]
YieldReaction ConditionsOperation in experiment
36% for 24.00 h; Reflux Propiolic acid (310 μL, 5 mmol; Alfa Aesar, Ward Hill, Mass.; catalog No. A13245) was dissolved in 13 mL of ethanol, giving a colorless solution, to which concentrated sulfuric acid (139 μL, 2.5 mmol) was added.
The resulting mixture was heated to reflux for 24 h, and then treated with 13 mL of water before being extracted with dichloromethane (10 mL; three times).
The combined organic layers were washed with water (10 mL; three times) and brine (10 mL), and then dried over anhydrous Na2SO4 (Thermo Fisher Scientific, Pittsburgh, PA; catalog No. S421-3).
Removal of the solvent under vacuum afforded the product as a light yellow color oil (177 mg, 36percent yield).
1H NMR (400 MHz, CDCl3, δ): 4.26 (q, 3JH-H=7.1 Hz, CH2, 2H), 2.92 (s, C≡CH, 1H), 1.33 (t, 3JH-H=7.2 Hz, CH3, 3H).
Reference: [1] Journal of the American Chemical Society, 1988, vol. 110, p. 3965
[2] Patent: US2016/264506, 2016, A1. Location in patent: Paragraph 0035
[3] Chemische Berichte, 1926, vol. 59, p. 1689
[4] Nippon Kagaku Zasshi, 1956, vol. 77, p. 1689,1691[5] Chem.Abstr., 1959, p. 5163
[6] Chemische Berichte, 1882, vol. 15, p. 2702
[7] Journal of the Chemical Society, 1907, vol. 91, p. 834
[8] Chemische Berichte, 1885, vol. 18, p. 677[9] Chemische Berichte, 1889, vol. 22, p. 69
[10] Journal of Fluorine Chemistry, 1993, vol. 62, # 2-3, p. 217 - 241
[11] Tetrahedron Letters, 2005, vol. 46, # 15, p. 2547 - 2549
[12] Patent: US8569361, 2013, B1. Location in patent: Paragraph 0108-0109
  • 2
  • [ 764-01-2 ]
  • [ 1972-28-7 ]
  • [ 108-95-2 ]
  • [ 13610-09-8 ]
  • [ 623-47-2 ]
YieldReaction ConditionsOperation in experiment
70% With triphenylphosphine In tetrahydrofuran; benzene But-2-ynyloxy-benzene
To a solution of 6.14 g (23.40 mmol) of triphenylphosphine dissolved in 100 mL of benzene and 50 mL of THF was added 1.75 mL (23.40 mmol) of 2-butyn-1-ol.
After five minutes 2.00 g (21.28 mmol) of the phenol, dissolved in 10 mL of THF, was added to the reaction followed by 3.69 mL (23.40 mmol) of diethyl azodicarboxylate.
The resulting reaction mixture was stirred for 18 h at room temperature and then concentrated in vacuo.
The residue was chromatographed on silica gel eluding with ethyl acetate/hexanes (1:10) to provide 2.18 g (70percent) of the desired propargylic ether as a clear liquid. EI Mass Spec: 146.0 M+
Reference: [1] Patent: US6358980, 2002, B1
  • 3
  • [ 107-19-7 ]
  • [ 1972-28-7 ]
  • [ 287108-60-5 ]
  • [ 623-47-2 ]
  • [ 287108-61-6 ]
YieldReaction ConditionsOperation in experiment
71% With triphenylphosphine In tetrahydrofuran; benzene EXAMPLE 5
5-Bromo-3-methyl-2-[methyl-(4-prop-2-ynyloxy-benzenesulfonyl)-amino]-benzoic acid methyl ester
To a solution of 0.317 g (1.208 mmol) of triphenylphosphine dissolved in 5 mL of benzene and 2 mL of THF was added 0.070 mL (1.208 mmol) of propargyl alcohol.
After five minutes 0.500 g (1.208 mmol) of the product of Example 4, dissolved in 2 mL of THF, was added to the reaction followed by 0.190 mL (1.208 mmol) of diethyl azodicarboxylate.
The resulting reaction mixture was stirred for 18 h at room temperature and then concentrated in vacuo.
The residue was chromatographed on silica gel eluding with ethyl acetate/hexanes (1:10) to provide 0.389 g (71percent) of the desired propargylic ether as a white solid.
Electrospray Mass Spec: 451.8 (M+H)+
Reference: [1] Patent: US6277885, 2001, B1
  • 4
  • [ 924-44-7 ]
  • [ 623-47-2 ]
Reference: [1] European Journal of Organic Chemistry, 2015, vol. 2015, # 34, p. 7602 - 7611
  • 5
  • [ 541-41-3 ]
  • [ 74-86-2 ]
  • [ 623-47-2 ]
Reference: [1] Angewandte Chemie - International Edition, 2014, vol. 53, # 16, p. 4154 - 4158[2] Angew. Chem., 2014, vol. 126, # 16, p. 4238 - 4242,5
[3] Chemical Communications, 2015, vol. 51, # 65, p. 13004 - 13007
  • 6
  • [ 527-60-6 ]
  • [ 541-41-3 ]
  • [ 471-25-0 ]
  • [ 1737-55-9 ]
  • [ 623-47-2 ]
Reference: [1] Helvetica Chimica Acta, 2000, vol. 83, # 5, p. 1022 - 1048
  • 7
  • [ 541-41-3 ]
  • [ 51114-00-2 ]
  • [ 471-25-0 ]
  • [ 1737-55-9 ]
  • [ 623-47-2 ]
Reference: [1] Helvetica Chimica Acta, 2000, vol. 83, # 5, p. 1022 - 1048
  • 8
  • [ 461695-81-8 ]
  • [ 7732-18-5 ]
  • [ 623-47-2 ]
Reference: [1] Organometallics, 2002, vol. 21, # 18, p. 3762 - 3773
  • 9
  • [ 119930-16-4 ]
  • [ 1099-45-2 ]
  • [ 623-47-2 ]
Reference: [1] Tetrahedron Letters, 1982, vol. 23, # 40, p. 4135 - 4138
  • 10
  • [ 38391-86-5 ]
  • [ 108-88-3 ]
  • [ 623-47-2 ]
Reference: [1] Zhurnal Obshchei Khimii, 1950, vol. 20, p. 1729,1731;engl.Ausg.S.1787,1789
  • 11
  • [ 38391-86-5 ]
  • [ 7732-18-5 ]
  • [ 623-47-2 ]
Reference: [1] Zhurnal Obshchei Khimii, 1950, vol. 20, p. 1729,1731;engl.Ausg.S.1787,1789
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