Home Cart 0 Sign in  

[ CAS No. 6964-21-2 ]

{[proInfo.proName]} ,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
Chemical Structure| 6964-21-2
Chemical Structure| 6964-21-2
Structure of 6964-21-2 * Storage: {[proInfo.prStorage]}

Quality Control of [ 6964-21-2 ]

Related Doc. of [ 6964-21-2 ]

SDS
Alternatived Products of [ 6964-21-2 ]
Alternatived Products of [ 6964-21-2 ]

Product Details of [ 6964-21-2 ]

CAS No. :6964-21-2 MDL No. :MFCD00005473
Formula : C6H6O2S Boiling Point : 274.3°C at 760 mmHg
Linear Structure Formula :- InChI Key :-
M.W :142.18 g/mol Pubchem ID :23404
Synonyms :

Safety of [ 6964-21-2 ]

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

Application In Synthesis of [ 6964-21-2 ]

  • Upstream synthesis route of [ 6964-21-2 ]
  • Downstream synthetic route of [ 6964-21-2 ]

[ 6964-21-2 ] Synthesis Path-Upstream   1~15

  • 1
  • [ 6964-21-2 ]
  • [ 13781-67-4 ]
YieldReaction ConditionsOperation in experiment
99%
Stage #1: With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; for 2 h;
Stage #2: With water In tetrahydrofuran; ethyl acetate
Step 2: 2-(thiophen-3-yl)ethanol Tetrahydrofuran (200 mL) was added to LiAlH4 (4.56 g, 0.12 mol) and the mixture was stirred at 0° C. 2-(thiophen-3-yl)acetic acid (14.2 g, 0.1 mol) in THF (100 mL) was added dropwise at this temperature. After the addition, the reaction mixture was stirred at 0° C. for further 2 hours. To the reaction mixture was added EtOAc (200 mL) slowly and then 5 mL of water. The suspension was filtered though ceilite, the filtrate was dried over anhydrous sodium sulfate and concentrated to dryness to afford 2-(thiophen-3-yl)ethanol (12.44 g, yield: 99percent). 1H NMR (MeOD, 400 MHz): δ5.92-5.87 (m, 1H), 5.69-5.66 (m, 1H), 5.57 (s, 1H) 2.90 (d, J=14.0 Hz, 1H), 2.38 (d, J=14 Hz, 1H), 1.55-1.42 (m, 2H).
98% With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; for 3 h; Schlenk technique; Inert atmosphere In a flame-dried Schlenk flask, equipped with a magnetic stirring bar, an argon inlet, and a septum, LiAlH4 (5.7 g, 150 mmol, 1.5 equiv) was dissolved in THF (100 mL) at 0 °C. A solution of 3-thienylacetic acid (3, 14.2 g, 100 mmol, 1.0 equiv) in THF (50 mL) at 0 °C was added dropwise. The mixture was stirred for 3 h at 0 °C and then it was carefully quenched with EtOAc and EtOH. Subsequently, 1–2percent NaOH (20 mL) was added and the mixture was stirred for 1 h, allowing aluminum hydroxide to precipitate as a granular solid. Finally, the mixture was filtered over Celite. The collected organic layers were dried (MgSO4), and the solvent was evaporated in vacuo to give the pure alcohol 4 (12.5 g, 98percent) as a pale yellow oil.
78% With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; for 7 h; To a 0 C cooled stirred suspension of lithium aluminiumhydride (8.0 g, 0.21 mol) in THF (100 mL) was added 3-Thiopheneaceticacid 01 (20 g, 0.14 mol) in THF (100 mL) drop wise over1 h. Reaction mixture was warmed to room temperature and stirredfor 6 h. Reaction progress was checked by TLC for completionand then quenched with 10percent NaOH solution. The mixture was filteredover Celite, washed with ethylacetate. Aqueous layer wasextracted with ethylacetate and the combined organic layer waswashed with brine. Dried over sodium sulfate and concentratedto yield 2 as a yellow liquid (14.2 g, 78percent) 1H NMR (MeOD, 400MHz): d 5.92–5.87 (m, 1H), 5.69–5.66 (m, 1H), 5.57 (s, 1H) 2.90(d, J = 14.0 Hz, 1H), 2.38 (d, J = 14 Hz, 1H), 1.55–1.42 (m, 2H). 13CNMR (DMSO d6, 100 MHz): 145.53, 129.13, 126.54, 121.45,64.46, 38.85; ESI-MS m/z: (Calcd for C6H8OS: 128.03); Found:128.9 [M+H]+.
3.59 g With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; for 1.25 h; Step 1: 2-(3-Thienyl)ethanol [00367] A solution of thiophene-3-acetic acid (4.982 g, 35.04 mmol) in THF ( 120 mL, 1500 mmol) was cooled to 0 °C, and lithium tetrahydroaluminate ( 1 .596 g, 42.05 mmol) was added slowly over 15 min. The reaction was allowed to warm to rt and stirred for 2hrs. The reaction was quenched via addition of water (5 mL) and EtOAc ( 10ml). The mixture was filtered, and the filter cake was washed with 30ml EtOAc. The filtrate was concentrated in vacuo to afford the title compound (3.59 g). NMR (400 MHz, Chloroform-d) δ 7.31 (dd, J = 4.9, 3.0 Hz, 1 H), 7.1 1 - 7.05 (m, 1 H), 7.05 - 6.97 (m, 1 H), 3.87 (t, J = 6.4 Hz, 2H), 2.92 (t, J = 6.4 Hz, 2H), 1.71 (s, 1 H).

Reference: [1] Patent: US2011/76291, 2011, A1, . Location in patent: Page/Page column 148
[2] Synthesis, 2005, # 2, p. 267 - 271
[3] Synthesis (Germany), 2015, vol. 47, # 24, p. 3972 - 3982
[4] Molecular Crystals and Liquid Crystals Science and Technology, Section A: Molecular Crystals and Liquid Crystals, 1994, vol. 256, p. 439 - 448
[5] Organic Process Research and Development, 2015, vol. 19, # 11, p. 1568 - 1575
[6] Bioorganic and Medicinal Chemistry, 2018, vol. 26, # 8, p. 1462 - 1469
[7] Tetrahedron, 2015, vol. 71, # 39, p. 7107 - 7123
[8] Patent: WO2016/4136, 2016, A1, . Location in patent: Paragraph 00367
  • 2
  • [ 6964-21-2 ]
  • [ 1641-09-4 ]
Reference: [1] Advanced Synthesis and Catalysis, 2014, vol. 356, # 8, p. 1697 - 1702
  • 3
  • [ 71637-34-8 ]
  • [ 201230-82-2 ]
  • [ 6964-21-2 ]
  • [ 616-44-4 ]
Reference: [1] Bulletin of the Chemical Society of Japan, 1998, vol. 71, # 3, p. 723 - 734
[2] Tetrahedron Letters, 1997, vol. 38, # 21, p. 3747 - 3750
  • 4
  • [ 34846-44-1 ]
  • [ 201230-82-2 ]
  • [ 6964-21-2 ]
Reference: [1] Tetrahedron Letters, 2000, vol. 41, # 40, p. 7601 - 7604
  • 5
  • [ 124-38-9 ]
  • [ 6964-21-2 ]
Reference: [1] Chemical Science, 2018, vol. 9, # 21, p. 4873 - 4878
  • 6
  • [ 13781-66-3 ]
  • [ 6964-21-2 ]
Reference: [1] Journal of the American Chemical Society, 1951, vol. 73, p. 2779[2] Journal of the American Chemical Society, 1952, vol. 74, p. 1066
  • 7
  • [ 34846-44-1 ]
  • [ 143-33-9 ]
  • [ 6964-21-2 ]
Reference: [1] Journal of the American Chemical Society, 1948, vol. 70, p. 1555,1557[2] Org. Synth. Coll., 1963, vol. Vol. IV, p. 919
  • 8
  • [ 41507-35-1 ]
  • [ 6964-21-2 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2000, vol. 10, # 15, p. 1723 - 1727
[2] Nippon Kagaku Zasshi, 1959, vol. 80, p. 1293,1295[3] Chem.Abstr., 1961, p. 6476
  • 9
  • [ 124687-94-1 ]
  • [ 6964-21-2 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2000, vol. 10, # 15, p. 1723 - 1727
  • 10
  • [ 88-13-1 ]
  • [ 6964-21-2 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2000, vol. 10, # 15, p. 1723 - 1727
  • 11
  • [ 37784-63-7 ]
  • [ 6964-21-2 ]
Reference: [1] Nippon Kagaku Zasshi, 1959, vol. 80, p. 1293,1295[2] Chem.Abstr., 1961, p. 6476
  • 12
  • [ 10486-61-0 ]
  • [ 6964-21-2 ]
  • [ 541-50-4 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1993, p. 2433 - 2440
  • 13
  • [ 53064-74-7 ]
  • [ 6964-21-2 ]
  • [ 187737-37-7 ]
Reference: [1] Tetrahedron Letters, 1989, vol. 30, # 13, p. 1699 - 1702
  • 14
  • [ 58416-26-5 ]
  • [ 6964-21-2 ]
  • [ 115-11-7 ]
Reference: [1] Tetrahedron Letters, 1989, vol. 30, # 13, p. 1699 - 1702
  • 15
  • [ 6964-21-2 ]
  • [ 1283095-48-6 ]
Reference: [1] Organic Process Research and Development, 2015, vol. 19, # 11, p. 1568 - 1575
[2] Organic Process Research and Development, 2015, vol. 19, # 11, p. 1568 - 1575
Historical Records

Related Functional Groups of
[ 6964-21-2 ]

Carboxylic Acids

Chemical Structure| 4282-29-5

[ 4282-29-5 ]

Thiophene-3,4-dicarboxylic acid

Similarity: 0.83

Chemical Structure| 78071-30-4

[ 78071-30-4 ]

4-Methylthiophene-3-carboxylic acid

Similarity: 0.83

Chemical Structure| 88-13-1

[ 88-13-1 ]

Thiophene-3-carboxylic acid

Similarity: 0.76

Chemical Structure| 16188-55-9

[ 16188-55-9 ]

4-(Methylthio)phenylacetic acid

Similarity: 0.64

Chemical Structure| 19156-54-8

[ 19156-54-8 ]

4,5,6,7-Tetrahydrobenzo[b]thiophene-3-carboxylic acid

Similarity: 0.63