Name: 94838-88-7|(6-Formylbenzo[d][1,3]dioxol-5-yl)boronic acid|98%
Brand: Ambeed
SKU: A928047
Price: 11.0 USD
Availability: InStock
Rating: 98 (28 reviews)

1
[ 104682-96-4 ]
[ 94838-88-7 ]
[ 40360-71-2 ]

Yield	Reaction Conditions	Operation in experiment
	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate In 1,2-dimethoxyethane Heating; Yield given;

Reference： [1]Siddiqui; Snieckus [Tetrahedron Letters, 1990, vol. 31, # 11, p. 1523 - 1526]

2
[ 94838-88-7 ]
[ 128810-33-3 ]
[ 128810-30-0 ]

Yield	Reaction Conditions	Operation in experiment
	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate In 1,2-dimethoxyethane for 24h; Heating; Yield given;

Reference： [1]Siddiqui; Snieckus [Tetrahedron Letters, 1990, vol. 31, # 11, p. 1523 - 1526]

3
[ 94838-88-7 ]
[ 180411-16-9 ]
[ 51116-29-1 ]

Yield	Reaction Conditions	Operation in experiment
35%	With palladium diacetate; sodium carbonate; triphenylphosphine In 1,2-dimethoxyethane Heating;

Reference： [1]Geen, Graham R.; Mann, Inderjit S.; Mullane, M. Valerie; McKillop, Alexander [Tetrahedron, 1998, vol. 54, # 33, p. 9875 - 9894]

4
[ 94838-88-7 ]
[ 18162-48-6 ]
[ 106-95-6 ]
2-(3',4',5'-trimethoxyphenyl)-4-methoxymethyl-1,3-dioxane [ No CAS ]
{2-[6-(1-Allyloxy-ethyl)-benzo[1,3]dioxol-5-yl]-3,4,5-trimethoxy-benzyloxy}-tert-butyl-dimethyl-silane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Yield given. Multistep reaction;

Reference： [1]Uemura, Motokazu; Daimon, Akira; Hayashi, Yoshinori [Journal of the Chemical Society. Chemical communications, 1995, # 19, p. 1943 - 1944]

5
[ 64490-45-5 ]
[ 94838-88-7 ]
[ 258283-81-7 ]

Yield	Reaction Conditions	Operation in experiment
62%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium hydrogencarbonate In 1,2-dimethoxyethane

Reference： [1]Monovich, Lauren G.; Le Huerou, Yvan; Roenn, Magnus; Molander, Gary A. [Journal of the American Chemical Society, 2000, vol. 122, # 1, p. 52 - 57]

6
[ 94838-88-7 ]
[ 106-95-6 ]
2-(3',4',5'-trimethoxyphenyl)-4-methoxymethyl-1,3-dioxane [ No CAS ]
[ 108-59-8 ]
(+/-)-steganone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multistep reaction;

Reference： [1]Kamikawa, Ken; Watanabe, Takashi; Daimon, Akira; Ue Mura, Motokazu [Tetrahedron, 2000, vol. 56, # 15, p. 2325 - 2337]

7
[ 67587-20-6 ]
[ 94838-88-7 ]
C₁₉H₂₄O₅ [ No CAS ]
C₁₉H₂₄O₅ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In 1,4-dioxane at 50℃; for 12h; Title compound not separated from byproducts.;

Reference： [1]Yang, Miao; Zhang, Xumu; Lu, Xiyan [Organic Letters, 2007, vol. 9, # 24, p. 5131 - 5133]

8
[ 7515-17-5 ]
[ 94838-88-7 ]
C₁₉H₁₆O₆ [ No CAS ]
C₁₉H₁₆O₆ [ No CAS ]

Reference： [1]Organic Letters,2007,vol. 9,p. 5131 - 5133

9
[ 94838-88-7 ]
[ 23326-27-4 ]
C₁₃H₁₂O₅ [ No CAS ]
C₁₃H₁₂O₅ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In 1,4-dioxane at 50℃; for 12h; Title compound not separated from byproducts.;

Reference： [1]Yang, Miao; Zhang, Xumu; Lu, Xiyan [Organic Letters, 2007, vol. 9, # 24, p. 5131 - 5133]

10
[ 18937-79-6 ]
[ 94838-88-7 ]
C₁₅H₁₆O₅ [ No CAS ]
C₁₅H₁₆O₅ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In 1,4-dioxane at 50℃; for 12h; Title compound not separated from byproducts.;

Reference： [1]Yang, Miao; Zhang, Xumu; Lu, Xiyan [Organic Letters, 2007, vol. 9, # 24, p. 5131 - 5133]

11
[ 94838-88-7 ]
(+/-)-steganone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 7 steps 1: 62 percent / Pd(PPh₃)4; aq. NaHCO₃ / 1,2-dimethoxy-ethane 2: Et₃N / CH₂Cl₂ 3: LiBr / acetone 4: 83 percent / Pd₂(dba)3; trifurylphosphine / 1,2-dimethoxy-ethane / 80 °C 5: 80 percent / SmI₂; t-BuOH; HMPA / tetrahydrofuran / 0 °C 6: Dess-Martin periodinane 7: 90 percent / NaOAc / ethanol / Heating
	Multi-step reaction with 7 steps 1: 62 percent / Pd(PPh₃)4; aq. NaHCO₃ / 1,2-dimethoxy-ethane 2: Et₃N / CH₂Cl₂ 3: LiBr / acetone 4: 83 percent / Pd₂(dba)3; trifurylphosphine / 1,2-dimethoxy-ethane / 80 °C 5: SmI₂; t-BuOH; HMPA / tetrahydrofuran / 0 °C 6: Dess-Martin periodinane 7: 90 percent / NaOAc / ethanol / Heating

Reference： [1]Monovich, Lauren G.; Le Huerou, Yvan; Roenn, Magnus; Molander, Gary A. [Journal of the American Chemical Society, 2000, vol. 122, # 1, p. 52 - 57]
[2]Monovich, Lauren G.; Le Huerou, Yvan; Roenn, Magnus; Molander, Gary A. [Journal of the American Chemical Society, 2000, vol. 122, # 1, p. 52 - 57]

12
[ 94838-88-7 ]
[ 258283-82-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 62 percent / Pd(PPh₃)4; aq. NaHCO₃ / 1,2-dimethoxy-ethane 2: Et₃N / CH₂Cl₂ 3: LiBr / acetone

Reference： [1]Monovich, Lauren G.; Le Huerou, Yvan; Roenn, Magnus; Molander, Gary A. [Journal of the American Chemical Society, 2000, vol. 122, # 1, p. 52 - 57]

13
[ 94838-88-7 ]
methanesulfonic acid 2-(6-formyl-benzo[1,3]dioxol-5-yl)-3,4,5-trimethoxy-benzyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 62 percent / Pd(PPh₃)4; aq. NaHCO₃ / 1,2-dimethoxy-ethane 2: Et₃N / CH₂Cl₂

Reference： [1]Monovich, Lauren G.; Le Huerou, Yvan; Roenn, Magnus; Molander, Gary A. [Journal of the American Chemical Society, 2000, vol. 122, # 1, p. 52 - 57]

14
[ 94838-88-7 ]
[ 258283-80-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: 62 percent / Pd(PPh₃)4; aq. NaHCO₃ / 1,2-dimethoxy-ethane 2: Et₃N / CH₂Cl₂ 3: LiBr / acetone 4: 83 percent / Pd₂(dba)3; trifurylphosphine / 1,2-dimethoxy-ethane / 80 °C

Reference： [1]Monovich, Lauren G.; Le Huerou, Yvan; Roenn, Magnus; Molander, Gary A. [Journal of the American Chemical Society, 2000, vol. 122, # 1, p. 52 - 57]

15
[ 94838-88-7 ]
picrosteganone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1: 62 percent / Pd(PPh₃)4; aq. NaHCO₃ / 1,2-dimethoxy-ethane 2: Et₃N / CH₂Cl₂ 3: LiBr / acetone 4: 83 percent / Pd₂(dba)3; trifurylphosphine / 1,2-dimethoxy-ethane / 80 °C 5: 80 percent / SmI₂; t-BuOH; HMPA / tetrahydrofuran / 0 °C 6: Dess-Martin periodinane
	Multi-step reaction with 6 steps 1: 62 percent / Pd(PPh₃)4; aq. NaHCO₃ / 1,2-dimethoxy-ethane 2: Et₃N / CH₂Cl₂ 3: LiBr / acetone 4: 83 percent / Pd₂(dba)3; trifurylphosphine / 1,2-dimethoxy-ethane / 80 °C 5: SmI₂; t-BuOH; HMPA / tetrahydrofuran / 0 °C 6: Dess-Martin periodinane

Reference： [1]Monovich, Lauren G.; Le Huerou, Yvan; Roenn, Magnus; Molander, Gary A. [Journal of the American Chemical Society, 2000, vol. 122, # 1, p. 52 - 57]
[2]Monovich, Lauren G.; Le Huerou, Yvan; Roenn, Magnus; Molander, Gary A. [Journal of the American Chemical Society, 2000, vol. 122, # 1, p. 52 - 57]

16
[ 94838-88-7 ]
isopicrosteganol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: 62 percent / Pd(PPh₃)4; aq. NaHCO₃ / 1,2-dimethoxy-ethane 2: Et₃N / CH₂Cl₂ 3: LiBr / acetone 4: 83 percent / Pd₂(dba)3; trifurylphosphine / 1,2-dimethoxy-ethane / 80 °C 5: 80 percent / SmI₂; t-BuOH; HMPA / tetrahydrofuran / 0 °C

Reference： [1]Monovich, Lauren G.; Le Huerou, Yvan; Roenn, Magnus; Molander, Gary A. [Journal of the American Chemical Society, 2000, vol. 122, # 1, p. 52 - 57]

17
[ 94838-88-7 ]
epipicrosteganol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: 62 percent / Pd(PPh₃)4; aq. NaHCO₃ / 1,2-dimethoxy-ethane 2: Et₃N / CH₂Cl₂ 3: LiBr / acetone 4: 83 percent / Pd₂(dba)3; trifurylphosphine / 1,2-dimethoxy-ethane / 80 °C 5: SmI₂; t-BuOH; HMPA / tetrahydrofuran / 0 °C

Reference： [1]Monovich, Lauren G.; Le Huerou, Yvan; Roenn, Magnus; Molander, Gary A. [Journal of the American Chemical Society, 2000, vol. 122, # 1, p. 52 - 57]

18
[ 171015-18-2 ]
[ 94838-88-7 ]
[ 171015-19-3 ]

Yield	Reaction Conditions	Operation in experiment
67%	With sodium carbonate In methanol; water reflux (1 h);

Reference： [1]Uemura, Motokazu; Daimon, Akira; Hayashi, Yoshinori [Journal of the Chemical Society. Chemical communications, 1995, # 19, p. 1943 - 1944]

19
[ 94838-88-7 ]
[ 122213-94-9 ]
[ 1086561-31-0 ]

Yield	Reaction Conditions	Operation in experiment
72%	With sodium carbonate In methanol; water; toluene at 90℃; for 15h;

Reference： [1]Mamane, Victor; Louërat, Frédéric; Iehl, Julien; Abboud, Mohamed; Fort, Yves [Tetrahedron, 2008, vol. 64, # 47, p. 10699 - 10705]

20
[ 94838-88-7 ]
[ 3430-22-6 ]
[ 1086561-33-2 ]

Yield	Reaction Conditions	Operation in experiment
98%	With sodium carbonate In methanol; water; toluene at 90℃; for 15h;

Reference： [1]Mamane, Victor; Louërat, Frédéric; Iehl, Julien; Abboud, Mohamed; Fort, Yves [Tetrahedron, 2008, vol. 64, # 47, p. 10699 - 10705]

21
[ 1042722-43-9 ]
[ 94838-88-7 ]
17,18-dimethoxy-13-methyl-5,7-dioxa-13-azapentacyclo[10.6.1.0^2,10.0^4,8.0^15,19]nonadeca-1,3,8,10,12⁽¹⁹⁾,15,17-heptaen-14-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; caesium carbonate In ethanol; toluene at 150℃; for 0.166667h; Microwave irradiation; Inert atmosphere;
80%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; caesium carbonate In ethanol; toluene at 150℃; for 0.166667h; Microwave irradiation;

Reference： [1]Kim, Joa Kyum; Kim, Young Ha; Nam, Ho Tae; Kim, Bum Tae; Heo, Jung-Nyoung [Organic Letters, 2008, vol. 10, # 16, p. 3543 - 3546]
[2]Location in patent: experimental part Choi, Young Lok; Kim, Joa Kyum; Choi, Sang-Un; Min, Yong-Ki; Bae, Myung-Ae; Kim, Bum Tae; Heo, Jung-Nyoung [Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 11, p. 3036 - 3040]

22
[ 1968-71-4 ]
[ 94838-88-7 ]
[ 73252-65-0 ]

Yield	Reaction Conditions	Operation in experiment
	With palladium diacetate; caesium carbonate; triphenylphosphine In 1,2-dimethoxyethane at 70℃;

Reference： [1]Location in patent: scheme or table Wu, Gang; Guo, Huan-Fang; Gao, Kun; Liu, Yi-Nan; Bastow, Kenneth F.; Morris-Natschke, Susan L.; Lee, Kuo-Hsiung; Xie, Lan [Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 19, p. 5272 - 5276]

23
[ 35274-53-4 ]
[ 94838-88-7 ]
[ 61599-76-6 ]

Yield	Reaction Conditions	Operation in experiment
	With palladium diacetate; caesium carbonate; triphenylphosphine In 1,2-dimethoxyethane at 70℃;

Reference： [1]Location in patent: scheme or table Wu, Gang; Guo, Huan-Fang; Gao, Kun; Liu, Yi-Nan; Bastow, Kenneth F.; Morris-Natschke, Susan L.; Lee, Kuo-Hsiung; Xie, Lan [Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 19, p. 5272 - 5276]

24
[ 2142-69-0 ]
[ 94838-88-7 ]
[ 1149344-88-6 ]

Yield	Reaction Conditions	Operation in experiment
99%	With potassium fluoride; palladium diacetate; di‐tert‐butyl‐(1‐phenylindol‐2‐yl)phosphane In tetrahydrofuran at 20℃; for 2h; Inert atmosphere;

Reference： [1]Young, Lok Choi; Yu, Chan-Mo; Bum, Tae Kim; Heo, Jung-Nyoung [Journal of Organic Chemistry, 2009, vol. 74, # 10, p. 3948 - 3951]

25
[ 1006-39-9 ]
[ 94838-88-7 ]
[ 1149344-98-8 ]

Reference： [1]Journal of Organic Chemistry,2009,vol. 74,p. 3948 - 3951

26
[ 94838-88-7 ]
[ 1012868-72-2 ]

Yield	Reaction Conditions	Operation in experiment
84%	With potassium hydrogenfluoride In methanol; water at 20℃; for 3h; Inert atmosphere;

Reference： [1]Molander, Gary A.; Febo-Ayala, Wilma; Jean-Gerard, Ludivine [Organic Letters, 2009, vol. 11, # 17, p. 3830 - 3833]

27
[ 14369-81-4 ]
[ 94838-88-7 ]
C₁₄H₁₄O₅ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
56%	With [(1,3-bis(diphenylphosphino)propane)Pd(H₂O)₂](BF₄)₂ In toluene at 25℃; for 0.666667h; diastereoselective reaction;

Reference： [1]Yu, Xufen; Lu, Xiyan [Organic Letters, 2009, vol. 11, # 19, p. 4366 - 4369]

28
[ 94838-88-7 ]
[ 146374-27-8 ]
C₁₂H₁₆BNO₅S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
81%	In ethanol; toluene Reflux;

Reference： [1]Location in patent: experimental part Yu, Xufen; Lu, Xiyan [Advanced Synthesis and Catalysis, 2011, vol. 353, # 14-15, p. 2805 - 2813]

29
[ 55757-60-3 ]
[ 94838-88-7 ]
CH₃OCOCH(NHCOOC(CH₃)3)C₄H₈NCHC₆H₂O₂CH₂B(OH)2 [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
56%	In water-d2 D2O, 16 h, 25°C; detected by NMR spectra;

Reference： [1]Cal, Pedro M. S. D.; Vicente, Joao B.; Pires, Elisabete; Coelho, Ana V.; Veiros, Lus F.; Cordeiro, Carlos; Gois, Pedro M. P. [Journal of the American Chemical Society, 2012, vol. 134, # 24, p. 10299 - 10305]

30
[ 94838-88-7 ]
[ 55757-60-3 ]
CH₃OCOCH(NHCOOC(CH₃)3)C₄H₈NCHC₆H₂O₂CH₂B(OH)2 [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In deuterium at 25℃; for 16h;

Reference： [1]Cal, Pedro M. S. D.; Vicente, Joao B.; Pires, Elisabete; Coelho, Ana V.; Veiros, Lus F.; Cordeiro, Carlos; Gois, Pedro M. P. [Journal of the American Chemical Society, 2012, vol. 134, # 24, p. 10299 - 10305]

31
[ 466639-53-2 ]
[ 94838-88-7 ]
[ 1459238-37-9 ]

Yield	Reaction Conditions	Operation in experiment
71%	With bis-triphenylphosphine-palladium(II) chloride; potassium carbonate In tetrahydrofuran at 20℃; Inert atmosphere;	3 4.5 General procedure for the preparation of biarylcarboxaldehydes (28a-c) General procedure: The mixture of 2-formylphenyl boronic acid 26a-c (1.0equiv), 2-bromo-1-iodo-4-methoxybenzene 27 (2.0equiv), and 5mol% PdCl2(PPh3)2 in THF (5mL) was stirred under Ar atmosphere at room temperature. A solution of 2N K2CO3 (25mL) was then transferred into the reaction via syringe until the reaction turned a brown-red solution. The reaction was allowed to stir at room temperature overnight. After checking by TLC, the reaction was quenched with water and partitioned with EtOAc to obtain the dark-brown crude oil. The crude product was purified by flash chromatography or preparative thin layer chromatography (EtOAc/Hexane) to obtain the product.

Reference： [1]Nealmongkol, Prattya; Tangdenpaisal, Kassrin; Sitthimonchai, Somkid; Ruchirawat, Somsak; Thasana, Nopporn [Tetrahedron, 2013, vol. 69, # 44, p. 9277 - 9283]

32
[ 94838-88-7 ]
diethyl (1-bromonaphthalen-2-yl)phosphonate [ No CAS ]
(-)-diethyl 1-(6-formylbenzo[d][1,3]dioxol-5-yl)naphthalen-2-ylphosphonate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
71%	With potassium phosphate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; (R)-(+)-2-(dicyclohexylphosphino)-2'-methoxy-1,1'-binaphthyl In toluene at 80℃; for 72h; Inert atmosphere; enantioselective reaction;

Reference： [1]Zhou, Yougui; Wang, Shouliang; Wu, Wenhao; Li, Qing; He, Yuwei; Zhuang, Yue; Li, Lanning; Pang, Jiyan; Zhou, Zhongyuan; Qiu, Liqin [Organic Letters, 2013, vol. 15, # 21, p. 5508 - 5511]

33
[ 94838-88-7 ]
diethyl (1-bromonaphthalen-2-yl)phosphonate [ No CAS ]
diethyl 1-(6-formylbenzo[d][1,3]dioxol-5-yl)naphthalen-2-ylphosphonate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾ In toluene at 50℃; Inert atmosphere;

Reference： [1]Zhou, Yougui; Wang, Shouliang; Wu, Wenhao; Li, Qing; He, Yuwei; Zhuang, Yue; Li, Lanning; Pang, Jiyan; Zhou, Zhongyuan; Qiu, Liqin [Organic Letters, 2013, vol. 15, # 21, p. 5508 - 5511]

34
[ 884855-68-9 ]
[ 94838-88-7 ]
[ 1571136-43-0 ]

Yield	Reaction Conditions	Operation in experiment
42%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate In ethanol; toluene at 150℃; for 0.166667h; Sealed tube; Microwave irradiation;

Reference： [1]Park, Kyeong-Yong; Kim, Bum Tae; Heo, Jung-Nyoung [European Journal of Organic Chemistry, 2014, vol. 2014, # 1, p. 164 - 170]

35
[ 1589518-11-5 ]
[ 94838-88-7 ]
[ 1589546-26-8 ]

Yield	Reaction Conditions	Operation in experiment
56%	With potassium phosphate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; (R)-(+)-2-(dicyclohexylphosphino)-2'-methoxy-1,1'-binaphthyl In toluene at 50℃; enantioselective reaction;

Reference： [1]Zhou, Yougui; Zhang, Xuepeng; Liang, Huiyi; Cao, Zhenkun; Zhao, Xiaoyu; He, Yuwei; Wang, Shouliang; Pang, Jiyan; Zhou, Zhongyuan; Ke, Zhuofeng; Qiu, Liqin [ACS Catalysis, 2014, vol. 4, # 5, p. 1390 - 1397]

36
[ 1334217-99-0 ]
[ 94838-88-7 ]
5-nitro-3-(tetrahydro-2H-pyran-2-yl)-3H-[1,3]dioxolo[4,5-j]pyrazolo[4,3-a]phenanthridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
23%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate In ethanol; water; toluene for 24h; Reflux;	4.1.6 5-Nitro-3-(tetrahydro-2H-pyran-2-yl)-3H-[1,3]dioxolo[4,5-j]pyrazolo[4,3-a]phenanthridine 6 Same procedure as for the preparation of compound 2. From 1 (112 mg, 0.289 mmol) and 2-formyl-4,5-methylenedioxyphenylboronic acid (112 mg, 0.577 mmol) in 1:1:1 toluene/ethanol/H2O mixture (2.4 mL), 24 h reflux. After column chromatography (cyclohexane/acetone 8:2; 7:3 and 1:1), the product was triturated in a 7:3 mixture of CH3CN/water and then filtered to give 6 (26 mg, 0.066 mmol, 23%) as an orange-yellow powder. Mp >250 °C; IR (ATR): 1532, 1456, 1250, 1044, 1034 cm-1; 1H NMR (400 MHz, DMSO-d6): 1.56-1.71 (2H, m), 1.71-1.85 (1H, m), 2.04-2.15 (2H, m), 2.44-2.56 (1H under solvent signal), 3.79-3.89 (1H, m), 3.89-3.98 (1H, m), 6.10 (1H, d, J = 9 Hz), 6.39 (2H, s), 7.82 (1H, s), 8.53 (1H, s), 8.80 (1H, s), 9.25 (1H, s), 9.40 (1H, s); 13C NMR (100 MHz, DMSO-d6): 22.1, 24.6, 28.8, 66.8, 102.9 (CH2), 84.2 (CH), 102.6, 105.6, 106.1, 134.9, 150.6 (CHarom), 117.9, 118.9, 124.7, 128.2, 132.0, 135.2, 148.6, 149.1, 152.5 (Carom); HRMS (ESI+) calcd for C20H17N4O5 (M+H)+ 393.1199, found 393.1205.

Reference： [1]Suchaud, Virginie; Gavara, Laurent; Giraud, Francis; Nauton, Lionel; Théry, Vincent; Anizon, Fabrice; Moreau, Pascale [Bioorganic and Medicinal Chemistry, 2014, vol. 22, # 17, p. 4704 - 4710]

37
[ 94838-88-7 ]
5-nitro-3H-[1,3]dioxolo[4,5-j]pyrazolo[4,3-a]phenanthridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / toluene; ethanol; water / 24 h / Reflux 2: toluene-4-sulfonic acid / ethanol; water / 24 h / Reflux

Reference： [1]Suchaud, Virginie; Gavara, Laurent; Giraud, Francis; Nauton, Lionel; Théry, Vincent; Anizon, Fabrice; Moreau, Pascale [Bioorganic and Medicinal Chemistry, 2014, vol. 22, # 17, p. 4704 - 4710]

38
[ 94838-88-7 ]
3H-[1,3]dioxolo[4,5-j]pyrazolo[4,3-a]phenanthridin-5-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / toluene; ethanol; water / 24 h / Reflux 2: toluene-4-sulfonic acid / ethanol; water / 24 h / Reflux 3: platinum(IV) oxide; hydrogen / ethyl acetate / 36 h

Reference： [1]Suchaud, Virginie; Gavara, Laurent; Giraud, Francis; Nauton, Lionel; Théry, Vincent; Anizon, Fabrice; Moreau, Pascale [Bioorganic and Medicinal Chemistry, 2014, vol. 22, # 17, p. 4704 - 4710]

39
2-iodo-3,4,5-trimethoxy-1-(methoxymethyl)benzene [ No CAS ]
[ 94838-88-7 ]
C₁₉H₂₀O₇ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
53%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate In methanol; water for 1h; Reflux;

Reference： [1]Yalcouye, Boubacar; Choppin, Sabine; Panossian, Armen; Leroux, Frédéric R.; Colobert, Françoise [European Journal of Organic Chemistry, 2014, vol. 2014, # 28, p. 6285 - 6294]

40
[ 2139-43-7 ]
[ 94838-88-7 ]
6'-(1,3-dioxolan-2-yl)-[5,5'-bibenzo[d][1,3]dioxole]-6-carbaldehyde [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium hydrogencarbonate In water; N,N-dimethyl-formamide at 125℃; for 0.416667h; Inert atmosphere; Sealed tube; Microwave irradiation;

Reference： [1]Yadav, Dharmendra B.; Taleli, Lebusetsa; Van Der Westhuyzen, Alet E.; Fernandes, Manuel A.; Dragoun, Maxim; Prokop, Aram; Schmalz, Hans-Günther; De Koning, Charles B.; Van Otterlo, Willem A. L. [European Journal of Organic Chemistry, 2015, vol. 2015, # 23, p. 5167 - 5182]

41
[ 94838-88-7 ]
[ 103477-58-3 ]
6-[2-(1,3-dioxolan-2-yl)-4,5-dimethoxyphenyl]benzo[1,3]dioxole-5-carbaldehyde [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium hydrogencarbonate In water; N,N-dimethyl-formamide at 125℃; for 0.416667h; Inert atmosphere; Sealed tube; Microwave irradiation;

Reference： [1]Yadav, Dharmendra B.; Taleli, Lebusetsa; Van Der Westhuyzen, Alet E.; Fernandes, Manuel A.; Dragoun, Maxim; Prokop, Aram; Schmalz, Hans-Günther; De Koning, Charles B.; Van Otterlo, Willem A. L. [European Journal of Organic Chemistry, 2015, vol. 2015, # 23, p. 5167 - 5182]

42
[ 94838-88-7 ]
[ 939-26-4 ]
2-(6-(naphth-2-yl-methyl)benzo[d][1,3]dioxol-5-yl)acetaldehyde [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
82%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate In tetrahydrofuran; water at 80℃; for 24h; Inert atmosphere; Schlenk technique;	3 2.2.1 General procedure for the preparation of ortho-formyl diarylmethanes 3 via the Suzuki-Miyaura reaction General procedure: A Schlenk flask (25mL) containing a biphasic mixture of oxygen free THF (10mL) and aqueous 2M solution of K2CO3 (4mL) was immersed in the oil bath. Then, ortho-formyl aromatic boronic acid 1 (2.40mmol), benzylic type halide 2 (2.20mmol) and Pd(PPh3)4 (0.06mmol) were added and the temperature of the oil bath was maintained at 80°C. The mixture was vigorously stirred at this temperature for 24h under argon atmosphere.Then, it was allowed to cool down, washed with H2O (8mL) and extracted with ethyl acetate (3x10mL). The organic layer was dried over anhydrous MgSO4. The solvent was removed in vacuum and crude product was purified by column chromatography over silica gel using a mixture of petroleum ether/acetone (20/1) as eluent.

Reference： [1]Kowalska, Emilia; Bałczewski, Piotr [Ultrasonics Sonochemistry, 2017, vol. 34, p. 743 - 753]

43
[ 94838-88-7 ]
[ 3840-30-0 ]
[ 42123-15-9 ]

Yield	Reaction Conditions	Operation in experiment
91%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate In tetrahydrofuran; water at 80℃; for 24h; Inert atmosphere; Schlenk technique;	6 2.2.1 General procedure for the preparation of ortho-formyl diarylmethanes 3 via the Suzuki-Miyaura reaction General procedure: A Schlenk flask (25mL) containing a biphasic mixture of oxygen free THF (10mL) and aqueous 2M solution of K2CO3 (4mL) was immersed in the oil bath. Then, ortho-formyl aromatic boronic acid 1 (2.40mmol), benzylic type halide 2 (2.20mmol) and Pd(PPh3)4 (0.06mmol) were added and the temperature of the oil bath was maintained at 80°C. The mixture was vigorously stirred at this temperature for 24h under argon atmosphere.Then, it was allowed to cool down, washed with H2O (8mL) and extracted with ethyl acetate (3x10mL). The organic layer was dried over anhydrous MgSO4. The solvent was removed in vacuum and crude product was purified by column chromatography over silica gel using a mixture of petroleum ether/acetone (20/1) as eluent.

Reference： [1]Kowalska, Emilia; Bałczewski, Piotr [Ultrasonics Sonochemistry, 2017, vol. 34, p. 743 - 753]

44
[ 2044-08-8 ]
[ 94838-88-7 ]
(4bS,8aR)-4b,5,6,7,8,8a-hexahydro-9H-fluoreno[2,3-d][1,3]dioxol-9-one [ No CAS ]
4b,5,6,7,8,8a-hexahydro-9H-fluoreno[2,3-d][1,3]dioxol-9-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / toluene; ethanol / 80 °C / Inert atmosphere; Sealed tube 2: sodium tetrakis[(3,5-di-trifluoromethyl)phenyl]borate; (R)-((4,4’-bi-1,3-benzodioxole)-5,5’-diyl)bis(bis(3,5-di-t-butyl-4-methoxyphenyl))phosphine; chloro(1,5-cyclooctadiene)rhodium(I) dimer / 1,4-dioxane / 24 h / 100 °C / Inert atmosphere; Sealed tube

Reference： [1]Johnson, Kirsten F.; Schneider, Eugene A.; Schumacher, Brian P.; Ellern, Arkady; Scanlon, Joseph D.; Stanley, Levi M. [Chemistry - A European Journal, 2016, vol. 22, # 44, p. 15619 - 15623]

45
[ 2044-08-8 ]
[ 94838-88-7 ]
[ 880643-58-3 ]

Yield	Reaction Conditions	Operation in experiment
63%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate In ethanol; toluene at 80℃; Inert atmosphere; Sealed tube;

Reference： [1]Johnson, Kirsten F.; Schneider, Eugene A.; Schumacher, Brian P.; Ellern, Arkady; Scanlon, Joseph D.; Stanley, Levi M. [Chemistry - A European Journal, 2016, vol. 22, # 44, p. 15619 - 15623]

46
[ 766-36-9 ]
[ 94838-88-7 ]
8-ethyl-5-hydroxy-9-methyl-[1,3]dioxolo[4′,5′:4,5]benzo[1,2-c]pyrrolo[2,1-f ][1,2]azaborinin-7(5H)-one [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2016,vol. 81,p. 10955 - 10963

47
[ 480-91-1 ]
[ 94838-88-7 ]
5-hydroxy[1,3]dioxolo[4″,5″:4′,5′]benzo[1′,2′:3,4][1,2]azaborinino[6,1-a]isoindol-7(5H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
20%	With 1,8-diazabicyclo[5.4.0]undec-7-ene In ethanol for 24h; Inert atmosphere; Reflux;

Reference： [1]Saint-Louis, Carl Jacky; Magill, Lacey L.; Wilson, Julie A.; Schroeder, Andrew R.; Harrell, Sarah E.; Jackson, Nicolle S.; Trindell, Jamie A.; Kim, Saraphina; Fisch, Alexander R.; Munro, Lyndsay; Catalano, Vincent J.; Webster, Charles Edwin; Vaughan, Pamela P.; Molek, Karen S.; Schrock, Alan K.; Huggins, Michael T. [Journal of Organic Chemistry, 2016, vol. 81, # 22, p. 10955 - 10963]

48
[ 94838-88-7 ]
[ 94670-88-9 ]
(E)-6'-styryl-[5,5'-bibenzo[d][1,3]dioxole]-6-carbaldehyde [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
53%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium hydrogencarbonate In water; N,N-dimethyl-formamide at 150℃; for 0.333333h; Microwave irradiation;

Reference： [1]McAtee, Christopher C.; Riehl, Paul S.; Schindler, Corinna S. [Journal of the American Chemical Society, 2017, vol. 139, # 8, p. 2960 - 2963]

49
[ 94838-88-7 ]
[ 868-85-9 ]
C₁₀H₁₂BO₇P [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%	With potassium carbonate In acetonitrile at 23 - 24℃; for 0.5h;	General Procedure for Synthesis of 15a-j General procedure: To a solution of the 2-formyl/acetyl-phenylboronic acid (3.00 mmol, 1.00 equiv.) in acetonitrile(5 ml) was added dimethyl phosphite (3.30 mmol, 1.10 equiv.) at 23-24 oC. To the above mixture was added potassium carbonate (9.00 mmol, 3.00 equiv.) in one lot at same temperature and allowed to stir for 30 min. The reaction mixture slowly turned into a white colored viscous paste which was acidified with acetic acid/hydrochloric acid. The mixture was extracted twice with diethyl ether (20 ml.) and the combined organic layer was concentrated to yield the crude product. Pure product was isolated by filtering the solids obtained from pouring water into the crude mixture.

Reference： [1]Kamath, Prashantha; Rajan, Ramya; Deshpande, Sudhindra H.; Montgomery, Mark; Lal, Mukul [Synthesis, 2017, vol. 49, # 11, p. 2435 - 2435]

50
[ 675109-26-9 ]
[ 94838-88-7 ]
9-bromo-5-hydroxy-[1,3]dioxolo[4″,5″:4′,5′]benzo[1′,2′:3,4][1,2]azaborinino[6,1-a]isoindol-7(5H)-one [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2017,vol. 15,p. 10172 - 10183

51
[ 110568-64-4 ]
[ 94838-88-7 ]
5-hydroxy-9-nitro-[1,3]dioxolo[4″,5″:4′,5′]benzo[1′,2′:3,4][1,2]azaborinino[6,1-a]isoindol-7(5H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%	With 1,8-diazabicyclo[5.4.0]undec-7-ene In ethanol for 48h; Inert atmosphere;

Reference： [1]Saint-Louis, Carl Jacky; Shavnore, Renée N.; McClinton, Caleb D. C.; Wilson, Julie A.; Magill, Lacey L.; Brown, Breanna M.; Lamb, Robert W.; Webster, Charles Edwin; Schrock, Alan K.; Huggins, Michael T. [Organic and Biomolecular Chemistry, 2017, vol. 15, # 48, p. 10172 - 10183]

52
[ 110568-64-4 ]
[ 94838-88-7 ]
9-amino-5-hydroxy-[1,3]dioxolo[4″,5″:4′,5′]benzo[1′,2′:3,4][1,2]azaborinino[6,1-a]isoindol-7(5H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 1,8-diazabicyclo[5.4.0]undec-7-ene / ethanol / 48 h / Inert atmosphere 2: sodiumsulfide nonahydrate / ethanol / 24 h / Reflux

Reference： [1]Saint-Louis, Carl Jacky; Shavnore, Renée N.; McClinton, Caleb D. C.; Wilson, Julie A.; Magill, Lacey L.; Brown, Breanna M.; Lamb, Robert W.; Webster, Charles Edwin; Schrock, Alan K.; Huggins, Michael T. [Organic and Biomolecular Chemistry, 2017, vol. 15, # 48, p. 10172 - 10183]

53
N,N,N-trimethyl-1,1-diphenylmethanaminium trifluoromethanesulfonate [ No CAS ]
[ 94838-88-7 ]
6-benzhydrylbenzo[d][1,3]dioxole-5-carbaldehyde [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
45%	With bis(benzonitrile)palladium(II) chloride; sodium carbonate; tricyclohexylphosphine In 1,2-dichloro-ethane at 80℃; for 12h; Inert atmosphere; Schlenk technique;

Reference： [1]Zhang, Zhenming; Wang, Hui; Qiu, Nianli; Kong, Yujing; Zeng, Wenjuan; Zhang, Yongquan; Zhao, Junfeng [Journal of Organic Chemistry, 2018, vol. 83, # 15, p. 8710 - 8715]

54
C₁₉H₂₂F₃NO₇S₂ [ No CAS ]
[ 94838-88-7 ]
tert-butyl (1R,4S)-2-(6-formylbenzo[d][1,3]dioxol-5-yl)-3-tosyl-7-azabicyclo[2.2.1]hept-2-ene-7-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With palladium diacetate; tris-(o-tolyl)phosphine; silver carbonate In acetonitrile at 80℃; for 3h;

Reference： [1]Verma, Prachi; Chandra, Atish; Pandey, Ganesh [Journal of Organic Chemistry, 2018, vol. 83, # 17, p. 9968 - 9977]

55
[ 76-09-5 ]
[ 94838-88-7 ]
6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[d][1,3]dioxole-5-carbaldehyde [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	In N,N-dimethyl-formamide at 20℃; for 21h;	5.2.2. (MD)BSIH (E)-N′-((6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[d][1,3]dioxol-5-yl)methylene)isonicotinohydrazide. A portion of 2-formyl-4,5-methylenedioxyphenylboronic acid (1 mmol, 0.194 g) and pinacol(1 mmol, 0.118 g) were dissolved in DMF and added to a roundbottom flask. The reaction stirred for 21 h at rt then dried by rotaryevaporation to give an off-white powder corresponding to 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[d][1,3]dioxole-5-carbaldehyde (MD-FBApin) in 80% yield. A portion of isoniazid(0.5 mmol, 0.068 g) was dissolved in 1 mL methanol and added to asolution of MD-FBApin (0.5 mmol, 0.138 g) dissolved in 2 mL ofmethanol. The reaction was stirred for 2 h over an oil bath at 100 °Cand cooled over ice. The liquid phase was then collected via vacuumfiltration and dried by rotary evaporation. A yellow powder wasisolated in 45% yield.

Reference： [1]Wang, Qin; Franz, Katherine J. [Bioorganic and Medicinal Chemistry, 2018, vol. 26, # 22, p. 5962 - 5972]

56
[ 76-09-5 ]
[ 94838-88-7 ]
(E)-N′-((6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[d][1,3]dioxol-5-yl)methylene)isonicotinohydrazide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: N,N-dimethyl-formamide / 21 h / 20 °C 2: methanol / 2 h / 100 °C

Reference： [1]Wang, Qin; Franz, Katherine J. [Bioorganic and Medicinal Chemistry, 2018, vol. 26, # 22, p. 5962 - 5972]

57
[ 94838-88-7 ]
[ 187661-86-5 ]
(±)-benzyl (1S,2S)-5-hydroxy-7-methylene-6,7-dihydro-5H-indeno[5,6-d][1,3]dioxole-6-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
48%	With nickel(II) acetate tetrahydrate In 1,4-dioxane; acetonitrile at 20℃; for 24h; Inert atmosphere; Sealed tube; diastereoselective reaction;

Reference： [1]Panchal, Heena; Clarke, Christopher; Bell, Charles; Karad, Somnath Narayan; Lewis, William; Lam, Hon Wai [Chemical Communications, 2018, vol. 54, # 87, p. 12389 - 12392]

58
[ 497-18-7 ]
[ 94838-88-7 ]
8H-[1,3]dioxolo[4”,5”:4’,5’]benzo[1’,2’:4,5][1,2,3]diazaborinino[3,2-b]-[1,3]dioxolo[4”,5”:4’,5’]benzo[1’,2’:4,5][1,2,3]diazaborinino[2,3-e][1,3,5,2,6]oxadiazadiborinin-8-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
97%	With formic acid In water for 2h; Reflux;	General procedure for the synthesis of pentacyclicoxadiazadiborinanes General procedure: To a stirred H2O (25 mL) suspension of the appropriateboronic acid-containing aldehyde (2.22 mmol) and 1 dropof formic acid was added an aqueous solution (5 mL) ofcarbohydrazide (100 mg, 1.11 mmol). Compound 7 wassynthesized using MeOH as the solvent. The reactionmixture was heated at reflux for 2 h, at which pointthe reaction was allowed to cool to room temperature(RT). The resulting precipitate was collected by suctionfiltration and washed with Et2O (2 × 10 mL) to afford thepentacyclic oxadiazadiborinanes as white or off-whitesolids.

Reference： [1]Geier, Stephen J.; Gormley, Patrick T.; MacCormack, Tyson J.; Masuda, Jason D.; Ninh Khuong, B.; Vogels, Christopher M.; Westcott, Stephen A. [Journal of the Brazilian Chemical Society, 2020, vol. 31, # 7, p. 1541 - 1550]

59
2-methyl-N-(3-phenylprop-2-yn-1-yl)-N-tosylacrylamide [ No CAS ]
[ 94838-88-7 ]
4',4'-dimethyl-6-phenyl-1'-tosylspiro[indeno[5,6-d][1,3]dioxole-5,3'-pyrrolidine]-5',7(6H)-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73%	With (S,S)-[2-(4'-isopropyloxazolin-2'-yl)ferrocenyl]diphenylphosphine; nickel(II) acetate tetrahydrate In 1-methyl-pyrrolidin-2-one at 100℃; for 36h; Sealed tube; Inert atmosphere; enantioselective reaction;

Reference： [1]Ding, Zhengtian; Wang, Yiming; Liu, Wenfeng; Chen, Yate; Kong, Wangqing [Journal of the American Chemical Society, 2021, vol. 143, # 1, p. 53 - 59]

60
[ 94838-88-7 ]
[ 121-69-7 ]
3-(4-(dimethylamino)phenyl)-[1,3]dioxolo[4',5':4,5]benzo[1,2-c][1,2]oxaborol-1(3H)-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In tetrahydrofuran at 60℃; for 24h;	General procedure: To a mixture of substituted indoles 6a -6g or N- substituted anilines 8a -8c (1.0 mmol), (2 -formylphenyl) boronic acid 5a- 5h (1.5 mmol) and THF (1.0 mL) was added at 25 °C. Then the mixture was stirred at 60°C for 24 h until the starting material was completely consumed (TLC monitoring). After completion, the crude product was purified by flash chromatography (silica gel, petroleum ether : ethyl acetate = 10 : 1- 30:1) to give 7a-7i (70 -95% yields) or 9a-9j ( 75%-95% yields) as a red or white solid.

Reference： [1]Yan, Yu-Hang; Li, Zhao-Feng; Ning, Xiang-Li; Deng, Ji; Yu, Jun-Lin; Luo, Yubin; Wang, Zhenling; Li, Guo; Li, Guo-Bo; Xiao, You-Cai [Bioorganic and Medicinal Chemistry Letters, 2021, vol. 41]

61
6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[d][1,3]dioxole-5-carbaldehyde [ No CAS ]
[ 94838-88-7 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[d][1,3]dioxole-5-carbaldehyde With sodium periodate In tetrahydrofuran; water at 20℃; for 0.333333h; Stage #2: With hydrogenchloride In tetrahydrofuran; water for 2h;	General procedure: To a round bottom flask was added bis(pinacolato)diboron (1.22 g, 4.8 mmol, 1.2 equiv.), substituted 2-bromo benzaldehyde 1a -1h (4.0 mmol, 1.0 equiv.), PdCl2(dppf) (88 mg, 0.12 mmol, 3 mol %) and KOAc (1.18 g, 12 mmol, 3.0 equiv.). The mixture was closed by a septum, purged by argon gas for several times then the dry 1,4-dioxane (15 mL) was then added into the reaction mixture and kept stirring at 90 °C for 8 h. The crude reaction mixture was diluted with EA, extracted by sat. NaCl. The combined organic layer was collected, dried over the Na2SO4 and concentrated in vacuo. The crude products 4a- 4h were subsequently used in the next step. To a solution of 4a -4h (4.0 mol, 1.0 equiv.) in THF: H2O = 10:1 (32 mL), was added NaIO4 (6.0 mmol, 1.5 equiv). The mixture was stirred at room temperature for 20 minutes until homogeneous. HCl (1.0 M in water, 10 mL) was then added, and the mixture was stirred for additional 2 h. After the starting material 4a -4h was consumed as indicated by TLC, The resulting mixture was extracted with DCM (3×50 mL), dried over anhydrous Na2SO4, and concentrated in vacuo. The residue was purified through flash column chromatography by using petroleum ether and ethyl acetate as eluent to give compounds 5a -5h (42-60% yields for two steps).

Reference： [1]Yan, Yu-Hang; Li, Zhao-Feng; Ning, Xiang-Li; Deng, Ji; Yu, Jun-Lin; Luo, Yubin; Wang, Zhenling; Li, Guo; Li, Guo-Bo; Xiao, You-Cai [Bioorganic and Medicinal Chemistry Letters, 2021, vol. 41]

62
[ 15930-53-7 ]
[ 94838-88-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: potassium acetate / 1,4-dioxane / 8 h / 90 °C / Inert atmosphere 2.1: sodium periodate / tetrahydrofuran; water / 0.33 h / 20 °C 2.2: 2 h

Reference： [1]Yan, Yu-Hang; Li, Zhao-Feng; Ning, Xiang-Li; Deng, Ji; Yu, Jun-Lin; Luo, Yubin; Wang, Zhenling; Li, Guo; Li, Guo-Bo; Xiao, You-Cai [Bioorganic and Medicinal Chemistry Letters, 2021, vol. 41]

63
[ 94838-88-7 ]
[ 824-98-6 ]
6-(3-methoxybenzyl)benzo[d][1,3]dioxole-5-carbaldehyde [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
67%	With bis-triphenylphosphine-palladium(II) chloride; sodium hydrogencarbonate In ethanol at 100℃; for 3h;

Reference： [1]Reamtong, Onrapak; Lapmanee, Sarawut; Tummatorn, Jumreang; Palavong, Nitwaree; Thongsornkleeb, Charnsak; Ruchirawat, Somsak [ACS Medicinal Chemistry Letters, 2021, vol. 12, # 9, p. 1449 - 1458]

64
[ 94838-88-7 ]
9-methoxy-6,11-dihydro-5H-[1,3]dioxolo[4',5':4,5]benzo[1,2-b]benzo[e]azepine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: bis-triphenylphosphine-palladium(II) chloride; sodium hydrogencarbonate / ethanol / 3 h / 100 °C 2: sodium tetrahydroborate / methanol; ethyl acetate / 0.5 h / 20 °C 3: phosphorus tribromide / dichloromethane / 0.5 h / 20 °C 4: sodium azide / dimethyl sulfoxide / 20 °C 5: trifluorormethanesulfonic acid / toluene / 0.5 h / 20 °C / Inert atmosphere

Reference： [1]Reamtong, Onrapak; Lapmanee, Sarawut; Tummatorn, Jumreang; Palavong, Nitwaree; Thongsornkleeb, Charnsak; Ruchirawat, Somsak [ACS Medicinal Chemistry Letters, 2021, vol. 12, # 9, p. 1449 - 1458]

65
[ 94838-88-7 ]
C₁₆H₁₆O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: bis-triphenylphosphine-palladium(II) chloride; sodium hydrogencarbonate / ethanol / 3 h / 100 °C 2: sodium tetrahydroborate / methanol; ethyl acetate / 0.5 h / 20 °C

Reference： [1]Reamtong, Onrapak; Lapmanee, Sarawut; Tummatorn, Jumreang; Palavong, Nitwaree; Thongsornkleeb, Charnsak; Ruchirawat, Somsak [ACS Medicinal Chemistry Letters, 2021, vol. 12, # 9, p. 1449 - 1458]

66
[ 94838-88-7 ]
C₁₆H₁₅BrO₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: bis-triphenylphosphine-palladium(II) chloride; sodium hydrogencarbonate / ethanol / 3 h / 100 °C 2: sodium tetrahydroborate / methanol; ethyl acetate / 0.5 h / 20 °C 3: phosphorus tribromide / dichloromethane / 0.5 h / 20 °C

Reference： [1]Reamtong, Onrapak; Lapmanee, Sarawut; Tummatorn, Jumreang; Palavong, Nitwaree; Thongsornkleeb, Charnsak; Ruchirawat, Somsak [ACS Medicinal Chemistry Letters, 2021, vol. 12, # 9, p. 1449 - 1458]

67
[ 94838-88-7 ]
5-(azidomethyl)-6-(3-methoxybenzyl)benzo[d][1,3]dioxole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: bis-triphenylphosphine-palladium(II) chloride; sodium hydrogencarbonate / ethanol / 3 h / 100 °C 2: sodium tetrahydroborate / methanol; ethyl acetate / 0.5 h / 20 °C 3: phosphorus tribromide / dichloromethane / 0.5 h / 20 °C 4: sodium azide / dimethyl sulfoxide / 20 °C

Reference： [1]Reamtong, Onrapak; Lapmanee, Sarawut; Tummatorn, Jumreang; Palavong, Nitwaree; Thongsornkleeb, Charnsak; Ruchirawat, Somsak [ACS Medicinal Chemistry Letters, 2021, vol. 12, # 9, p. 1449 - 1458]

68
[ 94838-88-7 ]
methyl 2-(2-bromo-3,4,5-trimethoxyphenyl)acetate [ No CAS ]
[ 55624-04-9 ]

Yield	Reaction Conditions	Operation in experiment
40%	With tripotassium phosphate tribasic; tetrakis-(triphenylphosphine)-palladium In 1,2-dimethoxyethane at 100℃; for 24h;

Reference： [1]Chen, Xiaoyan; Goto, Masuo; Lee, Kuo-Hsiung; Morris-Natschke, Susan L.; Xie, Lan [ACS Medicinal Chemistry Letters, 2021, vol. 12, # 12, p. 1948 - 1954]

69
[ 4697-57-8 ]
[ 94838-88-7 ]
methyl 2,3-methylenedioxy-6,7-dimethoxyphenanthrene-9-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
36%	With tripotassium phosphate tribasic; tetrakis-(triphenylphosphine)-palladium In 1,2-dimethoxyethane at 80℃; for 1h; Microwave irradiation;

Reference： [1]Chen, Xiaoyan; Goto, Masuo; Lee, Kuo-Hsiung; Morris-Natschke, Susan L.; Xie, Lan [ACS Medicinal Chemistry Letters, 2021, vol. 12, # 12, p. 1948 - 1954]

70
[ 56952-05-7 ]
[ 94838-88-7 ]
methyl 7-hydroxy-6-methoxy-2,3-methylenedioxyphenanthrene-9-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
50%	With tripotassium phosphate tribasic; tetrakis-(triphenylphosphine)-palladium In 1,2-dimethoxyethane at 100℃; for 1h; Inert atmosphere;

Reference： [1]Chen, Xiaoyan; Goto, Masuo; Lee, Kuo-Hsiung; Morris-Natschke, Susan L.; Xie, Lan [ACS Medicinal Chemistry Letters, 2021, vol. 12, # 12, p. 1948 - 1954]

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
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CAS No. :	94838-88-7	MDL No. :	MFCD01319005
Formula :	C₈H₇BO₅	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	AKEPUIJBVDGLMX-UHFFFAOYSA-N
M.W :	193.95	Pubchem ID :	2773423
Synonyms :

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:

Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
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. 94838-88-7 ] {[proInfo.proName]}

Quality Control of [ 94838-88-7 ]

Related Doc. of [ 94838-88-7 ]

Product Details of [ 94838-88-7 ]

Safety of [ 94838-88-7 ]

Application In Synthesis of [ 94838-88-7 ]

[ 94838-88-7 ] Synthesis Path-Downstream 1~70

Related Functional Groups of
[ 94838-88-7 ]

Organoboron

Aldehydes

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

[ CAS No. 94838-88-7 ] {[proInfo.proName]}

Quality Control of [ 94838-88-7 ]

Related Doc. of [ 94838-88-7 ]

Product Details of [ 94838-88-7 ]

Safety of [ 94838-88-7 ]

Application In Synthesis of [ 94838-88-7 ]

[ 94838-88-7 ] Synthesis Path-Downstream 1~70

Related Functional Groups of [ 94838-88-7 ]

Organoboron

Aldehydes

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 94838-88-7 ]