Name: 3951-89-1|7-Bromo-3,4-dihydro-1H-benzo[b]azepin-5(2H)-one|96%
Brand: Ambeed
SKU: A835303
Price: 87.0 USD
Availability: InStock
Rating: 99 (40 reviews)

1
[ 3951-89-1 ]
[ 24424-99-5 ]
[ 313724-26-4 ]

Yield	Reaction Conditions	Operation in experiment
	With 4-dimethylaminopyridine In tetrahydrofuran for 1.5h; Heating;
	With luitdine In tetrahydrofuran at 70℃; for 4h;	2.3 Step 3: Synthesis of compound BB-1B-4 The reactants BB-1B-3 (6 g) and Boc anhydride (15.16 g) were dissolved in tetrahydrofuran (100 mL), and N,N-lutidine (4.58 g) was added to form a mixture. The mixture was stirred at 70°C for 4 hours, quenched with water (100 mL) and was extracted with ethyl acetate (100 mL×3). The combined organic layer was washed with saturated brine (100 mL), dried with anhydrous sodium sulfate, filtered and evaporated under reduced pressure to obtain a residue. The residue was purified by silica gel column chromatography (petroleum ether/ethyl acetate = 50:1 to 20:1) to obtain BB-1B-4. MS-ESI (m/z): 283.9[M-55]+
	With luitdine In tetrahydrofuran at 70℃; for 4h;	2.3 Step 3: Synthesis of compound BB-1B-4 The reactants BB-1B-3 (6 g) and Boc anhydride (15.16 g) were dissolved in tetrahydrofuran (100 mL), and N,N-lutidine (4.58 g) was added to form a mixture. The mixture was stirred at 70°C for 4 hours, quenched with water (100 mL) and was extracted with ethyl acetate (100 mL×3). The combined organic layer was washed with saturated brine (100 mL), dried with anhydrous sodium sulfate, filtered and evaporated under reduced pressure to obtain a residue. The residue was purified by silica gel column chromatography (petroleum ether/ethyl acetate = 50:1 to 20:1) to obtain BB-1B-4. MS-ESI (m/z): 283.9[M-55]+

Reference： [1]Seto, Masaki; Aramaki, Yoshio; Okawa, Tomohiro; Miyamoto, Naoki; Aikawa, Katsuji; Kanzaki, Naoyuki; Niwa, Shin-Ichi; Iizawa, Yuji; Baba, Masanori; Shiraishi, Mitsuru [Chemical and Pharmaceutical Bulletin, 2004, vol. 52, # 5, p. 577 - 590]
[2]Current Patent Assignee: SHENZHEN LINGFANG BIO MEDICINE TECH; SHENZHEN LINGFANG BIOTECH; WUXI APPTEC CO., LTD. - EP3988098, 2022, A1 Location in patent: Paragraph 00077; 0081
[3]Current Patent Assignee: SHENZHEN LINGFANG BIO MEDICINE TECH; SHENZHEN LINGFANG BIOTECH; WUXI APPTEC CO., LTD. - EP3988098, 2022, A1 Location in patent: Paragraph 00077; 0081

2
7-bromo-5-oxo-2,3,4,5-tetrahydro-1H-benzo[b]azepine-4-carboxylic acid ethyl ester [ No CAS ]
[ 3951-89-1 ]

Yield	Reaction Conditions	Operation in experiment
21%	With sulfuric acid; acetic acid at 90℃; for 2.5h;

Reference： [1]Seto, Masaki; Aramaki, Yoshio; Okawa, Tomohiro; Miyamoto, Naoki; Aikawa, Katsuji; Kanzaki, Naoyuki; Niwa, Shin-Ichi; Iizawa, Yuji; Baba, Masanori; Shiraishi, Mitsuru [Chemical and Pharmaceutical Bulletin, 2004, vol. 52, # 5, p. 577 - 590]

3
[ 3951-89-1 ]
[ 313724-44-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1: DMAP / tetrahydrofuran / 1.5 h / Heating 2: 3.89 g / sodium methoxide / 2.5 h / Heating 3: NaBH₄ / tetrahydrofuran; methanol / 1 h / -15 °C 4: Et₃N / tetrahydrofuran / 14 h / 20 °C 5: 2.53 g / 1,8-diazabicyclo[5,4,0]undec-7-ene / tetrahydrofuran / 0.17 h / Heating 6: 100 percent / aq. HCl / ethyl acetate / 0.5 h / 80 °C

Reference： [1]Seto, Masaki; Aramaki, Yoshio; Okawa, Tomohiro; Miyamoto, Naoki; Aikawa, Katsuji; Kanzaki, Naoyuki; Niwa, Shin-Ichi; Iizawa, Yuji; Baba, Masanori; Shiraishi, Mitsuru [Chemical and Pharmaceutical Bulletin, 2004, vol. 52, # 5, p. 577 - 590]

4
[ 3951-89-1 ]
[ 313736-13-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 7 steps 1: DMAP / tetrahydrofuran / 1.5 h / Heating 2: 3.89 g / sodium methoxide / 2.5 h / Heating 3: NaBH₄ / tetrahydrofuran; methanol / 1 h / -15 °C 4: Et₃N / tetrahydrofuran / 14 h / 20 °C 5: 2.53 g / 1,8-diazabicyclo[5,4,0]undec-7-ene / tetrahydrofuran / 0.17 h / Heating 6: 100 percent / aq. HCl / ethyl acetate / 0.5 h / 80 °C 7: 76 percent / triacetoxyborohydride / 1,2-dichloro-ethane / 12 h / 20 °C

Reference： [1]Seto, Masaki; Aramaki, Yoshio; Okawa, Tomohiro; Miyamoto, Naoki; Aikawa, Katsuji; Kanzaki, Naoyuki; Niwa, Shin-Ichi; Iizawa, Yuji; Baba, Masanori; Shiraishi, Mitsuru [Chemical and Pharmaceutical Bulletin, 2004, vol. 52, # 5, p. 577 - 590]

5
[ 3951-89-1 ]
[ 313736-39-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 7 steps 1: DMAP / tetrahydrofuran / 1.5 h / Heating 2: 3.89 g / sodium methoxide / 2.5 h / Heating 3: NaBH₄ / tetrahydrofuran; methanol / 1 h / -15 °C 4: Et₃N / tetrahydrofuran / 14 h / 20 °C 5: 2.53 g / 1,8-diazabicyclo[5,4,0]undec-7-ene / tetrahydrofuran / 0.17 h / Heating 6: 100 percent / aq. HCl / ethyl acetate / 0.5 h / 80 °C 7: 87 percent / triacetoxyborohydride / 1,2-dichloro-ethane / 20 °C

Reference： [1]Seto, Masaki; Aramaki, Yoshio; Okawa, Tomohiro; Miyamoto, Naoki; Aikawa, Katsuji; Kanzaki, Naoyuki; Niwa, Shin-Ichi; Iizawa, Yuji; Baba, Masanori; Shiraishi, Mitsuru [Chemical and Pharmaceutical Bulletin, 2004, vol. 52, # 5, p. 577 - 590]

6
[ 3951-89-1 ]
7-bromo-1-(3-methyl-butyl)-2,3-dihydro-1H-benzo[b]azepine-4-carbonyl chloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 9 steps 1: DMAP / tetrahydrofuran / 1.5 h / Heating 2: 3.89 g / sodium methoxide / 2.5 h / Heating 3: NaBH₄ / tetrahydrofuran; methanol / 1 h / -15 °C 4: Et₃N / tetrahydrofuran / 14 h / 20 °C 5: 2.53 g / 1,8-diazabicyclo[5,4,0]undec-7-ene / tetrahydrofuran / 0.17 h / Heating 6: 100 percent / aq. HCl / ethyl acetate / 0.5 h / 80 °C 7: 87 percent / triacetoxyborohydride / 1,2-dichloro-ethane / 20 °C 8: 91 percent / HCl / ethyl acetate / 20 °C 9: SOCl₂; DMF / tetrahydrofuran / 20 °C

Reference： [1]Seto, Masaki; Aramaki, Yoshio; Okawa, Tomohiro; Miyamoto, Naoki; Aikawa, Katsuji; Kanzaki, Naoyuki; Niwa, Shin-Ichi; Iizawa, Yuji; Baba, Masanori; Shiraishi, Mitsuru [Chemical and Pharmaceutical Bulletin, 2004, vol. 52, # 5, p. 577 - 590]

7
[ 3951-89-1 ]
[ 313736-45-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 8 steps 1: DMAP / tetrahydrofuran / 1.5 h / Heating 2: 3.89 g / sodium methoxide / 2.5 h / Heating 3: NaBH₄ / tetrahydrofuran; methanol / 1 h / -15 °C 4: Et₃N / tetrahydrofuran / 14 h / 20 °C 5: 2.53 g / 1,8-diazabicyclo[5,4,0]undec-7-ene / tetrahydrofuran / 0.17 h / Heating 6: 100 percent / aq. HCl / ethyl acetate / 0.5 h / 80 °C 7: 87 percent / triacetoxyborohydride / 1,2-dichloro-ethane / 20 °C 8: 91 percent / HCl / ethyl acetate / 20 °C

Reference： [1]Seto, Masaki; Aramaki, Yoshio; Okawa, Tomohiro; Miyamoto, Naoki; Aikawa, Katsuji; Kanzaki, Naoyuki; Niwa, Shin-Ichi; Iizawa, Yuji; Baba, Masanori; Shiraishi, Mitsuru [Chemical and Pharmaceutical Bulletin, 2004, vol. 52, # 5, p. 577 - 590]

8
[ 3951-89-1 ]
[ 313724-37-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: DMAP / tetrahydrofuran / 1.5 h / Heating 2: 3.89 g / sodium methoxide / 2.5 h / Heating 3: NaBH₄ / tetrahydrofuran; methanol / 1 h / -15 °C 4: Et₃N / tetrahydrofuran / 14 h / 20 °C 5: 2.53 g / 1,8-diazabicyclo[5,4,0]undec-7-ene / tetrahydrofuran / 0.17 h / Heating
	Multi-step reaction with 4 steps 1.1: luitdine / tetrahydrofuran / 4 h / 70 °C 2.1: sodium methoxide / 2 h / 100 °C / Inert atmosphere 3.1: sodium tetrahydridoborate; methanol / tetrahydrofuran / 0.5 h / -40 - -15 °C 4.1: triethylamine; methanesulfonyl chloride / tetrahydrofuran / 15 h / 20 °C / Inert atmosphere 4.2: 1 h / 20 °C / Inert atmosphere

Reference： [1]Seto, Masaki; Aramaki, Yoshio; Okawa, Tomohiro; Miyamoto, Naoki; Aikawa, Katsuji; Kanzaki, Naoyuki; Niwa, Shin-Ichi; Iizawa, Yuji; Baba, Masanori; Shiraishi, Mitsuru [Chemical and Pharmaceutical Bulletin, 2004, vol. 52, # 5, p. 577 - 590]
[2]Current Patent Assignee: SHENZHEN LINGFANG BIO MEDICINE TECH; SHENZHEN LINGFANG BIOTECH; WUXI APPTEC CO., LTD. - EP3988098, 2022, A1

9
[ 3951-89-1 ]
7-Bromo-5-hydroxy-2,3,4,5-tetrahydro-benzo[b]azepine-1,4-dicarboxylic acid 1-tert-butyl ester 4-methyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: DMAP / tetrahydrofuran / 1.5 h / Heating 2: 3.89 g / sodium methoxide / 2.5 h / Heating 3: NaBH₄ / tetrahydrofuran; methanol / 1 h / -15 °C
	Multi-step reaction with 3 steps 1: luitdine / tetrahydrofuran / 4 h / 70 °C 2: sodium methoxide / 2 h / 100 °C / Inert atmosphere 3: sodium tetrahydridoborate; methanol / tetrahydrofuran / 0.5 h / -40 - -15 °C

Reference： [1]Seto, Masaki; Aramaki, Yoshio; Okawa, Tomohiro; Miyamoto, Naoki; Aikawa, Katsuji; Kanzaki, Naoyuki; Niwa, Shin-Ichi; Iizawa, Yuji; Baba, Masanori; Shiraishi, Mitsuru [Chemical and Pharmaceutical Bulletin, 2004, vol. 52, # 5, p. 577 - 590]
[2]Current Patent Assignee: SHENZHEN LINGFANG BIO MEDICINE TECH; SHENZHEN LINGFANG BIOTECH; WUXI APPTEC CO., LTD. - EP3988098, 2022, A1

10
[ 3951-89-1 ]
[ 313724-31-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: DMAP / tetrahydrofuran / 1.5 h / Heating 2: 3.89 g / sodium methoxide / 2.5 h / Heating
	Multi-step reaction with 2 steps 1: luitdine / tetrahydrofuran / 4 h / 70 °C 2: sodium methoxide / 2 h / 100 °C / Inert atmosphere

Reference： [1]Seto, Masaki; Aramaki, Yoshio; Okawa, Tomohiro; Miyamoto, Naoki; Aikawa, Katsuji; Kanzaki, Naoyuki; Niwa, Shin-Ichi; Iizawa, Yuji; Baba, Masanori; Shiraishi, Mitsuru [Chemical and Pharmaceutical Bulletin, 2004, vol. 52, # 5, p. 577 - 590]
[2]Current Patent Assignee: SHENZHEN LINGFANG BIO MEDICINE TECH; SHENZHEN LINGFANG BIOTECH; WUXI APPTEC CO., LTD. - EP3988098, 2022, A1

11
[ 3951-89-1 ]
7-bromo-5-methanesulfonyloxy-2,3,4,5-tetrahydro-benzo[b]azepine-1,4-dicarboxylic acid 1-tert-butyl ester 4-methyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: DMAP / tetrahydrofuran / 1.5 h / Heating 2: 3.89 g / sodium methoxide / 2.5 h / Heating 3: NaBH₄ / tetrahydrofuran; methanol / 1 h / -15 °C 4: Et₃N / tetrahydrofuran / 14 h / 20 °C

Reference： [1]Seto, Masaki; Aramaki, Yoshio; Okawa, Tomohiro; Miyamoto, Naoki; Aikawa, Katsuji; Kanzaki, Naoyuki; Niwa, Shin-Ichi; Iizawa, Yuji; Baba, Masanori; Shiraishi, Mitsuru [Chemical and Pharmaceutical Bulletin, 2004, vol. 52, # 5, p. 577 - 590]

12
[ 3951-89-1 ]
[ 313724-71-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 7 steps 1: DMAP / tetrahydrofuran / 1.5 h / Heating 2: 3.89 g / sodium methoxide / 2.5 h / Heating 3: NaBH₄ / tetrahydrofuran; methanol / 1 h / -15 °C 4: Et₃N / tetrahydrofuran / 14 h / 20 °C 5: 2.53 g / 1,8-diazabicyclo[5,4,0]undec-7-ene / tetrahydrofuran / 0.17 h / Heating 6: 82 percent / aq. K₂CO₃; Pd(PPh₃)4 / toluene; ethanol / Heating 7: 93 percent / aq. HCl / ethyl acetate / 80 °C

Reference： [1]Seto, Masaki; Aramaki, Yoshio; Okawa, Tomohiro; Miyamoto, Naoki; Aikawa, Katsuji; Kanzaki, Naoyuki; Niwa, Shin-Ichi; Iizawa, Yuji; Baba, Masanori; Shiraishi, Mitsuru [Chemical and Pharmaceutical Bulletin, 2004, vol. 52, # 5, p. 577 - 590]

13
[ 3951-89-1 ]
[ 313750-60-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 7 steps 1: DMAP / tetrahydrofuran / 1.5 h / Heating 2: 3.89 g / sodium methoxide / 2.5 h / Heating 3: NaBH₄ / tetrahydrofuran; methanol / 1 h / -15 °C 4: Et₃N / tetrahydrofuran / 14 h / 20 °C 5: 2.53 g / 1,8-diazabicyclo[5,4,0]undec-7-ene / tetrahydrofuran / 0.17 h / Heating 6: 100 percent / aq. HCl / ethyl acetate / 0.5 h / 80 °C 7: 56 percent / aq. K₂CO₃; Pd(PPh₃)4 / toluene; ethanol / Heating
	Multi-step reaction with 6 steps 1.1: luitdine / tetrahydrofuran / 4 h / 70 °C 2.1: sodium methoxide / 2 h / 100 °C / Inert atmosphere 3.1: sodium tetrahydridoborate; methanol / tetrahydrofuran / 0.5 h / -40 - -15 °C 4.1: triethylamine; methanesulfonyl chloride / tetrahydrofuran / 15 h / 20 °C / Inert atmosphere 4.2: 1 h / 20 °C / Inert atmosphere 5.1: potassium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II) dichloromethane adduct / lithium hydroxide monohydrate; dimethyl sulfoxide / 16 h / 80 °C / Inert atmosphere 6.1: hydrogenchloride / ethyl acetate / 1 h / 20 °C

Reference： [1]Seto, Masaki; Aramaki, Yoshio; Okawa, Tomohiro; Miyamoto, Naoki; Aikawa, Katsuji; Kanzaki, Naoyuki; Niwa, Shin-Ichi; Iizawa, Yuji; Baba, Masanori; Shiraishi, Mitsuru [Chemical and Pharmaceutical Bulletin, 2004, vol. 52, # 5, p. 577 - 590]
[2]Current Patent Assignee: SHENZHEN LINGFANG BIO MEDICINE TECH; SHENZHEN LINGFANG BIOTECH; WUXI APPTEC CO., LTD. - EP3988098, 2022, A1

14
[ 3951-89-1 ]
[ 313727-06-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 8 steps 1: DMAP / tetrahydrofuran / 1.5 h / Heating 2: 3.89 g / sodium methoxide / 2.5 h / Heating 3: NaBH₄ / tetrahydrofuran; methanol / 1 h / -15 °C 4: Et₃N / tetrahydrofuran / 14 h / 20 °C 5: 2.53 g / 1,8-diazabicyclo[5,4,0]undec-7-ene / tetrahydrofuran / 0.17 h / Heating 6: 82 percent / aq. K₂CO₃; Pd(PPh₃)4 / toluene; ethanol / Heating 7: 93 percent / aq. HCl / ethyl acetate / 80 °C 8: 97 percent / pyridine / tetrahydrofuran / 0.5 h / 20 °C

Reference： [1]Seto, Masaki; Aramaki, Yoshio; Okawa, Tomohiro; Miyamoto, Naoki; Aikawa, Katsuji; Kanzaki, Naoyuki; Niwa, Shin-Ichi; Iizawa, Yuji; Baba, Masanori; Shiraishi, Mitsuru [Chemical and Pharmaceutical Bulletin, 2004, vol. 52, # 5, p. 577 - 590]

15
[ 3951-89-1 ]
1-acetyl-7-(4-morpholin-4-yl-phenyl)-2,3-dihydro-1H-benzo[b]azepine-4-carbonyl chloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 10 steps 1: DMAP / tetrahydrofuran / 1.5 h / Heating 2: 3.89 g / sodium methoxide / 2.5 h / Heating 3: NaBH₄ / tetrahydrofuran; methanol / 1 h / -15 °C 4: Et₃N / tetrahydrofuran / 14 h / 20 °C 5: 2.53 g / 1,8-diazabicyclo[5,4,0]undec-7-ene / tetrahydrofuran / 0.17 h / Heating 6: 82 percent / aq. K₂CO₃; Pd(PPh₃)4 / toluene; ethanol / Heating 7: 93 percent / aq. HCl / ethyl acetate / 80 °C 8: 97 percent / pyridine / tetrahydrofuran / 0.5 h / 20 °C 9: 98 percent / aq. NaOH / tetrahydrofuran; methanol / 20 °C 10: SOCl₂; DMF / tetrahydrofuran / 20 °C

Reference： [1]Seto, Masaki; Aramaki, Yoshio; Okawa, Tomohiro; Miyamoto, Naoki; Aikawa, Katsuji; Kanzaki, Naoyuki; Niwa, Shin-Ichi; Iizawa, Yuji; Baba, Masanori; Shiraishi, Mitsuru [Chemical and Pharmaceutical Bulletin, 2004, vol. 52, # 5, p. 577 - 590]

16
[ 3951-89-1 ]
[ 313727-12-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 9 steps 1: DMAP / tetrahydrofuran / 1.5 h / Heating 2: 3.89 g / sodium methoxide / 2.5 h / Heating 3: NaBH₄ / tetrahydrofuran; methanol / 1 h / -15 °C 4: Et₃N / tetrahydrofuran / 14 h / 20 °C 5: 2.53 g / 1,8-diazabicyclo[5,4,0]undec-7-ene / tetrahydrofuran / 0.17 h / Heating 6: 82 percent / aq. K₂CO₃; Pd(PPh₃)4 / toluene; ethanol / Heating 7: 93 percent / aq. HCl / ethyl acetate / 80 °C 8: 97 percent / pyridine / tetrahydrofuran / 0.5 h / 20 °C 9: 98 percent / aq. NaOH / tetrahydrofuran; methanol / 20 °C

Reference： [1]Seto, Masaki; Aramaki, Yoshio; Okawa, Tomohiro; Miyamoto, Naoki; Aikawa, Katsuji; Kanzaki, Naoyuki; Niwa, Shin-Ichi; Iizawa, Yuji; Baba, Masanori; Shiraishi, Mitsuru [Chemical and Pharmaceutical Bulletin, 2004, vol. 52, # 5, p. 577 - 590]

17
[ 3951-89-1 ]
[ 597583-16-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 10 steps 1: DMAP / tetrahydrofuran / 1.5 h / Heating 2: 3.89 g / sodium methoxide / 2.5 h / Heating 3: NaBH₄ / tetrahydrofuran; methanol / 1 h / -15 °C 4: Et₃N / tetrahydrofuran / 14 h / 20 °C 5: 2.53 g / 1,8-diazabicyclo[5,4,0]undec-7-ene / tetrahydrofuran / 0.17 h / Heating 6: 100 percent / aq. HCl / ethyl acetate / 0.5 h / 80 °C 7: 76 percent / triacetoxyborohydride / 1,2-dichloro-ethane / 12 h / 20 °C 8: 62 percent / aq. K₂CO₃; Pd(PPh₃)4 / toluene; ethanol / Heating 9: 84 percent / aq. NaOH / tetrahydrofuran; methanol / 20 h / 20 °C 10: SOCl₂; DMF / tetrahydrofuran / 20 °C

Reference： [1]Seto, Masaki; Aramaki, Yoshio; Okawa, Tomohiro; Miyamoto, Naoki; Aikawa, Katsuji; Kanzaki, Naoyuki; Niwa, Shin-Ichi; Iizawa, Yuji; Baba, Masanori; Shiraishi, Mitsuru [Chemical and Pharmaceutical Bulletin, 2004, vol. 52, # 5, p. 577 - 590]

18
[ 3951-89-1 ]
[ 313736-28-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 8 steps 1: DMAP / tetrahydrofuran / 1.5 h / Heating 2: 3.89 g / sodium methoxide / 2.5 h / Heating 3: NaBH₄ / tetrahydrofuran; methanol / 1 h / -15 °C 4: Et₃N / tetrahydrofuran / 14 h / 20 °C 5: 2.53 g / 1,8-diazabicyclo[5,4,0]undec-7-ene / tetrahydrofuran / 0.17 h / Heating 6: 100 percent / aq. HCl / ethyl acetate / 0.5 h / 80 °C 7: 76 percent / triacetoxyborohydride / 1,2-dichloro-ethane / 12 h / 20 °C 8: 62 percent / aq. K₂CO₃; Pd(PPh₃)4 / toluene; ethanol / Heating

Reference： [1]Seto, Masaki; Aramaki, Yoshio; Okawa, Tomohiro; Miyamoto, Naoki; Aikawa, Katsuji; Kanzaki, Naoyuki; Niwa, Shin-Ichi; Iizawa, Yuji; Baba, Masanori; Shiraishi, Mitsuru [Chemical and Pharmaceutical Bulletin, 2004, vol. 52, # 5, p. 577 - 590]

19
[ 3951-89-1 ]
[ 313736-34-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 9 steps 1: DMAP / tetrahydrofuran / 1.5 h / Heating 2: 3.89 g / sodium methoxide / 2.5 h / Heating 3: NaBH₄ / tetrahydrofuran; methanol / 1 h / -15 °C 4: Et₃N / tetrahydrofuran / 14 h / 20 °C 5: 2.53 g / 1,8-diazabicyclo[5,4,0]undec-7-ene / tetrahydrofuran / 0.17 h / Heating 6: 100 percent / aq. HCl / ethyl acetate / 0.5 h / 80 °C 7: 76 percent / triacetoxyborohydride / 1,2-dichloro-ethane / 12 h / 20 °C 8: 62 percent / aq. K₂CO₃; Pd(PPh₃)4 / toluene; ethanol / Heating 9: 84 percent / aq. NaOH / tetrahydrofuran; methanol / 20 h / 20 °C

Reference： [1]Seto, Masaki; Aramaki, Yoshio; Okawa, Tomohiro; Miyamoto, Naoki; Aikawa, Katsuji; Kanzaki, Naoyuki; Niwa, Shin-Ichi; Iizawa, Yuji; Baba, Masanori; Shiraishi, Mitsuru [Chemical and Pharmaceutical Bulletin, 2004, vol. 52, # 5, p. 577 - 590]

20
[ 3951-89-1 ]
7-[4-(2-butoxy-ethoxy)-phenyl]-1-cyclopropylmethyl-2,3-dihydro-1H-benzo[b]azepine-4-carbonyl chloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 10 steps 1: DMAP / tetrahydrofuran / 1.5 h / Heating 2: 3.89 g / sodium methoxide / 2.5 h / Heating 3: NaBH₄ / tetrahydrofuran; methanol / 1 h / -15 °C 4: Et₃N / tetrahydrofuran / 14 h / 20 °C 5: 2.53 g / 1,8-diazabicyclo[5,4,0]undec-7-ene / tetrahydrofuran / 0.17 h / Heating 6: 100 percent / aq. HCl / ethyl acetate / 0.5 h / 80 °C 7: 56 percent / aq. K₂CO₃; Pd(PPh₃)4 / toluene; ethanol / Heating 8: 100 percent / triacetoxyborohydride / 1,2-dichloro-ethane / 20 °C 9: 96 percent / aq. NaOH / tetrahydrofuran; methanol / 20 °C 10: SOCl₂; DMF / tetrahydrofuran / 20 °C

Reference： [1]Seto, Masaki; Aramaki, Yoshio; Okawa, Tomohiro; Miyamoto, Naoki; Aikawa, Katsuji; Kanzaki, Naoyuki; Niwa, Shin-Ichi; Iizawa, Yuji; Baba, Masanori; Shiraishi, Mitsuru [Chemical and Pharmaceutical Bulletin, 2004, vol. 52, # 5, p. 577 - 590]

21
[ 3951-89-1 ]
7-[4-(2-butoxy-ethoxy)-phenyl]-1-phenyl-2,3-dihydro-1H-benzo[b]azepine-4-carbonyl chloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 10 steps 1: DMAP / tetrahydrofuran / 1.5 h / Heating 2: 3.89 g / sodium methoxide / 2.5 h / Heating 3: NaBH₄ / tetrahydrofuran; methanol / 1 h / -15 °C 4: Et₃N / tetrahydrofuran / 14 h / 20 °C 5: 2.53 g / 1,8-diazabicyclo[5,4,0]undec-7-ene / tetrahydrofuran / 0.17 h / Heating 6: 100 percent / aq. HCl / ethyl acetate / 0.5 h / 80 °C 7: 56 percent / aq. K₂CO₃; Pd(PPh₃)4 / toluene; ethanol / Heating 8: 71 percent / copper(II) pivalate / CH₂Cl₂ / 20 °C 9: 75 percent / aq. NaOH / tetrahydrofuran; methanol / 20 °C 10: SOCl₂; DMF / tetrahydrofuran / 20 °C

Reference： [1]Seto, Masaki; Aramaki, Yoshio; Okawa, Tomohiro; Miyamoto, Naoki; Aikawa, Katsuji; Kanzaki, Naoyuki; Niwa, Shin-Ichi; Iizawa, Yuji; Baba, Masanori; Shiraishi, Mitsuru [Chemical and Pharmaceutical Bulletin, 2004, vol. 52, # 5, p. 577 - 590]

22
[ 3951-89-1 ]
[ 313729-65-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 8 steps 1: DMAP / tetrahydrofuran / 1.5 h / Heating 2: 3.89 g / sodium methoxide / 2.5 h / Heating 3: NaBH₄ / tetrahydrofuran; methanol / 1 h / -15 °C 4: Et₃N / tetrahydrofuran / 14 h / 20 °C 5: 2.53 g / 1,8-diazabicyclo[5,4,0]undec-7-ene / tetrahydrofuran / 0.17 h / Heating 6: 100 percent / aq. HCl / ethyl acetate / 0.5 h / 80 °C 7: 56 percent / aq. K₂CO₃; Pd(PPh₃)4 / toluene; ethanol / Heating 8: 100 percent / triacetoxyborohydride / 1,2-dichloro-ethane / 20 °C

Reference： [1]Seto, Masaki; Aramaki, Yoshio; Okawa, Tomohiro; Miyamoto, Naoki; Aikawa, Katsuji; Kanzaki, Naoyuki; Niwa, Shin-Ichi; Iizawa, Yuji; Baba, Masanori; Shiraishi, Mitsuru [Chemical and Pharmaceutical Bulletin, 2004, vol. 52, # 5, p. 577 - 590]

23
[ 3951-89-1 ]
[ 313724-66-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1: DMAP / tetrahydrofuran / 1.5 h / Heating 2: 3.89 g / sodium methoxide / 2.5 h / Heating 3: NaBH₄ / tetrahydrofuran; methanol / 1 h / -15 °C 4: Et₃N / tetrahydrofuran / 14 h / 20 °C 5: 2.53 g / 1,8-diazabicyclo[5,4,0]undec-7-ene / tetrahydrofuran / 0.17 h / Heating 6: 82 percent / aq. K₂CO₃; Pd(PPh₃)4 / toluene; ethanol / Heating

Reference： [1]Seto, Masaki; Aramaki, Yoshio; Okawa, Tomohiro; Miyamoto, Naoki; Aikawa, Katsuji; Kanzaki, Naoyuki; Niwa, Shin-Ichi; Iizawa, Yuji; Baba, Masanori; Shiraishi, Mitsuru [Chemical and Pharmaceutical Bulletin, 2004, vol. 52, # 5, p. 577 - 590]

24
[ 3951-89-1 ]
[ 313730-21-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 9 steps 1: DMAP / tetrahydrofuran / 1.5 h / Heating 2: 3.89 g / sodium methoxide / 2.5 h / Heating 3: NaBH₄ / tetrahydrofuran; methanol / 1 h / -15 °C 4: Et₃N / tetrahydrofuran / 14 h / 20 °C 5: 2.53 g / 1,8-diazabicyclo[5,4,0]undec-7-ene / tetrahydrofuran / 0.17 h / Heating 6: 100 percent / aq. HCl / ethyl acetate / 0.5 h / 80 °C 7: 56 percent / aq. K₂CO₃; Pd(PPh₃)4 / toluene; ethanol / Heating 8: 71 percent / copper(II) pivalate / CH₂Cl₂ / 20 °C 9: 75 percent / aq. NaOH / tetrahydrofuran; methanol / 20 °C

Reference： [1]Seto, Masaki; Aramaki, Yoshio; Okawa, Tomohiro; Miyamoto, Naoki; Aikawa, Katsuji; Kanzaki, Naoyuki; Niwa, Shin-Ichi; Iizawa, Yuji; Baba, Masanori; Shiraishi, Mitsuru [Chemical and Pharmaceutical Bulletin, 2004, vol. 52, # 5, p. 577 - 590]

25
[ 3951-89-1 ]
[ 313730-15-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 8 steps 1: DMAP / tetrahydrofuran / 1.5 h / Heating 2: 3.89 g / sodium methoxide / 2.5 h / Heating 3: NaBH₄ / tetrahydrofuran; methanol / 1 h / -15 °C 4: Et₃N / tetrahydrofuran / 14 h / 20 °C 5: 2.53 g / 1,8-diazabicyclo[5,4,0]undec-7-ene / tetrahydrofuran / 0.17 h / Heating 6: 100 percent / aq. HCl / ethyl acetate / 0.5 h / 80 °C 7: 56 percent / aq. K₂CO₃; Pd(PPh₃)4 / toluene; ethanol / Heating 8: 71 percent / copper(II) pivalate / CH₂Cl₂ / 20 °C

Reference： [1]Seto, Masaki; Aramaki, Yoshio; Okawa, Tomohiro; Miyamoto, Naoki; Aikawa, Katsuji; Kanzaki, Naoyuki; Niwa, Shin-Ichi; Iizawa, Yuji; Baba, Masanori; Shiraishi, Mitsuru [Chemical and Pharmaceutical Bulletin, 2004, vol. 52, # 5, p. 577 - 590]

26
[ 3951-89-1 ]
[ 313729-70-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 9 steps 1: DMAP / tetrahydrofuran / 1.5 h / Heating 2: 3.89 g / sodium methoxide / 2.5 h / Heating 3: NaBH₄ / tetrahydrofuran; methanol / 1 h / -15 °C 4: Et₃N / tetrahydrofuran / 14 h / 20 °C 5: 2.53 g / 1,8-diazabicyclo[5,4,0]undec-7-ene / tetrahydrofuran / 0.17 h / Heating 6: 100 percent / aq. HCl / ethyl acetate / 0.5 h / 80 °C 7: 56 percent / aq. K₂CO₃; Pd(PPh₃)4 / toluene; ethanol / Heating 8: 100 percent / triacetoxyborohydride / 1,2-dichloro-ethane / 20 °C 9: 96 percent / aq. NaOH / tetrahydrofuran; methanol / 20 °C

Reference： [1]Seto, Masaki; Aramaki, Yoshio; Okawa, Tomohiro; Miyamoto, Naoki; Aikawa, Katsuji; Kanzaki, Naoyuki; Niwa, Shin-Ichi; Iizawa, Yuji; Baba, Masanori; Shiraishi, Mitsuru [Chemical and Pharmaceutical Bulletin, 2004, vol. 52, # 5, p. 577 - 590]

27
[ 3951-89-1 ]
[ 719297-14-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 8 steps 1: DMAP / tetrahydrofuran / 1.5 h / Heating 2: 3.89 g / sodium methoxide / 2.5 h / Heating 3: NaBH₄ / tetrahydrofuran; methanol / 1 h / -15 °C 4: Et₃N / tetrahydrofuran / 14 h / 20 °C 5: 2.53 g / 1,8-diazabicyclo[5,4,0]undec-7-ene / tetrahydrofuran / 0.17 h / Heating 6: 100 percent / aq. HCl / ethyl acetate / 0.5 h / 80 °C 7: 56 percent / aq. K₂CO₃; Pd(PPh₃)4 / toluene; ethanol / Heating 8: 88 percent / triacetoxyborohydride / 1,2-dichloro-ethane / 20 °C

Reference： [1]Seto, Masaki; Aramaki, Yoshio; Okawa, Tomohiro; Miyamoto, Naoki; Aikawa, Katsuji; Kanzaki, Naoyuki; Niwa, Shin-Ichi; Iizawa, Yuji; Baba, Masanori; Shiraishi, Mitsuru [Chemical and Pharmaceutical Bulletin, 2004, vol. 52, # 5, p. 577 - 590]

28
[ 3951-89-1 ]
[ 313729-45-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 8 steps 1: DMAP / tetrahydrofuran / 1.5 h / Heating 2: 3.89 g / sodium methoxide / 2.5 h / Heating 3: NaBH₄ / tetrahydrofuran; methanol / 1 h / -15 °C 4: Et₃N / tetrahydrofuran / 14 h / 20 °C 5: 2.53 g / 1,8-diazabicyclo[5,4,0]undec-7-ene / tetrahydrofuran / 0.17 h / Heating 6: 100 percent / aq. HCl / ethyl acetate / 0.5 h / 80 °C 7: 56 percent / aq. K₂CO₃; Pd(PPh₃)4 / toluene; ethanol / Heating 8: 100 percent / triacetoxyborohydride / 1,2-dichloro-ethane / 20 °C

Reference： [1]Seto, Masaki; Aramaki, Yoshio; Okawa, Tomohiro; Miyamoto, Naoki; Aikawa, Katsuji; Kanzaki, Naoyuki; Niwa, Shin-Ichi; Iizawa, Yuji; Baba, Masanori; Shiraishi, Mitsuru [Chemical and Pharmaceutical Bulletin, 2004, vol. 52, # 5, p. 577 - 590]

29
[ 3951-89-1 ]
7-[4-(2-butoxy-ethoxy)-phenyl]-1-thiazol-2-ylmethyl-2,3-dihydro-1H-benzo[b]azepine-4-carbonyl chloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 10 steps 1: DMAP / tetrahydrofuran / 1.5 h / Heating 2: 3.89 g / sodium methoxide / 2.5 h / Heating 3: NaBH₄ / tetrahydrofuran; methanol / 1 h / -15 °C 4: Et₃N / tetrahydrofuran / 14 h / 20 °C 5: 2.53 g / 1,8-diazabicyclo[5,4,0]undec-7-ene / tetrahydrofuran / 0.17 h / Heating 6: 100 percent / aq. HCl / ethyl acetate / 0.5 h / 80 °C 7: 56 percent / aq. K₂CO₃; Pd(PPh₃)4 / toluene; ethanol / Heating 8: 88 percent / triacetoxyborohydride / 1,2-dichloro-ethane / 20 °C 9: 78 percent / aq. NaOH / tetrahydrofuran; methanol / 20 °C 10: SOCl₂; DMF / tetrahydrofuran / 20 °C

Reference： [1]Seto, Masaki; Aramaki, Yoshio; Okawa, Tomohiro; Miyamoto, Naoki; Aikawa, Katsuji; Kanzaki, Naoyuki; Niwa, Shin-Ichi; Iizawa, Yuji; Baba, Masanori; Shiraishi, Mitsuru [Chemical and Pharmaceutical Bulletin, 2004, vol. 52, # 5, p. 577 - 590]

30
[ 3951-89-1 ]
[ 313751-90-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 9 steps 1: DMAP / tetrahydrofuran / 1.5 h / Heating 2: 3.89 g / sodium methoxide / 2.5 h / Heating 3: NaBH₄ / tetrahydrofuran; methanol / 1 h / -15 °C 4: Et₃N / tetrahydrofuran / 14 h / 20 °C 5: 2.53 g / 1,8-diazabicyclo[5,4,0]undec-7-ene / tetrahydrofuran / 0.17 h / Heating 6: 100 percent / aq. HCl / ethyl acetate / 0.5 h / 80 °C 7: 56 percent / aq. K₂CO₃; Pd(PPh₃)4 / toluene; ethanol / Heating 8: 88 percent / triacetoxyborohydride / 1,2-dichloro-ethane / 20 °C 9: 78 percent / aq. NaOH / tetrahydrofuran; methanol / 20 °C

Reference： [1]Seto, Masaki; Aramaki, Yoshio; Okawa, Tomohiro; Miyamoto, Naoki; Aikawa, Katsuji; Kanzaki, Naoyuki; Niwa, Shin-Ichi; Iizawa, Yuji; Baba, Masanori; Shiraishi, Mitsuru [Chemical and Pharmaceutical Bulletin, 2004, vol. 52, # 5, p. 577 - 590]

31
[ 3951-89-1 ]
[ 313729-50-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 9 steps 1: DMAP / tetrahydrofuran / 1.5 h / Heating 2: 3.89 g / sodium methoxide / 2.5 h / Heating 3: NaBH₄ / tetrahydrofuran; methanol / 1 h / -15 °C 4: Et₃N / tetrahydrofuran / 14 h / 20 °C 5: 2.53 g / 1,8-diazabicyclo[5,4,0]undec-7-ene / tetrahydrofuran / 0.17 h / Heating 6: 100 percent / aq. HCl / ethyl acetate / 0.5 h / 80 °C 7: 56 percent / aq. K₂CO₃; Pd(PPh₃)4 / toluene; ethanol / Heating 8: 100 percent / triacetoxyborohydride / 1,2-dichloro-ethane / 20 °C 9: 89 percent / aq. NaOH / tetrahydrofuran; methanol / 20 °C

Reference： [1]Seto, Masaki; Aramaki, Yoshio; Okawa, Tomohiro; Miyamoto, Naoki; Aikawa, Katsuji; Kanzaki, Naoyuki; Niwa, Shin-Ichi; Iizawa, Yuji; Baba, Masanori; Shiraishi, Mitsuru [Chemical and Pharmaceutical Bulletin, 2004, vol. 52, # 5, p. 577 - 590]

32
[ 3951-89-1 ]
1-benzyl-7-[4-(2-butoxy-ethoxy)-phenyl]-2,3-dihydro-1H-benzo[b]azepine-4-carbonyl chloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 10 steps 1: DMAP / tetrahydrofuran / 1.5 h / Heating 2: 3.89 g / sodium methoxide / 2.5 h / Heating 3: NaBH₄ / tetrahydrofuran; methanol / 1 h / -15 °C 4: Et₃N / tetrahydrofuran / 14 h / 20 °C 5: 2.53 g / 1,8-diazabicyclo[5,4,0]undec-7-ene / tetrahydrofuran / 0.17 h / Heating 6: 100 percent / aq. HCl / ethyl acetate / 0.5 h / 80 °C 7: 56 percent / aq. K₂CO₃; Pd(PPh₃)4 / toluene; ethanol / Heating 8: 100 percent / triacetoxyborohydride / 1,2-dichloro-ethane / 20 °C 9: 89 percent / aq. NaOH / tetrahydrofuran; methanol / 20 °C 10: SOCl₂; DMF / tetrahydrofuran / 20 °C

Reference： [1]Seto, Masaki; Aramaki, Yoshio; Okawa, Tomohiro; Miyamoto, Naoki; Aikawa, Katsuji; Kanzaki, Naoyuki; Niwa, Shin-Ichi; Iizawa, Yuji; Baba, Masanori; Shiraishi, Mitsuru [Chemical and Pharmaceutical Bulletin, 2004, vol. 52, # 5, p. 577 - 590]

33
[ 3951-89-1 ]
[ 313729-87-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 8 steps 1: DMAP / tetrahydrofuran / 1.5 h / Heating 2: 3.89 g / sodium methoxide / 2.5 h / Heating 3: NaBH₄ / tetrahydrofuran; methanol / 1 h / -15 °C 4: Et₃N / tetrahydrofuran / 14 h / 20 °C 5: 2.53 g / 1,8-diazabicyclo[5,4,0]undec-7-ene / tetrahydrofuran / 0.17 h / Heating 6: 100 percent / aq. HCl / ethyl acetate / 0.5 h / 80 °C 7: 56 percent / aq. K₂CO₃; Pd(PPh₃)4 / toluene; ethanol / Heating 8: 100 percent / triacetoxyborohydride / 1,2-dichloro-ethane / 20 °C

Reference： [1]Seto, Masaki; Aramaki, Yoshio; Okawa, Tomohiro; Miyamoto, Naoki; Aikawa, Katsuji; Kanzaki, Naoyuki; Niwa, Shin-Ichi; Iizawa, Yuji; Baba, Masanori; Shiraishi, Mitsuru [Chemical and Pharmaceutical Bulletin, 2004, vol. 52, # 5, p. 577 - 590]

34
[ 3951-89-1 ]
7-[4-(2-butoxy-ethoxy)-phenyl]-1-cyclobutylmethyl-2,3-dihydro-1H-benzo[b]azepine-4-carbonyl chloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 10 steps 1: DMAP / tetrahydrofuran / 1.5 h / Heating 2: 3.89 g / sodium methoxide / 2.5 h / Heating 3: NaBH₄ / tetrahydrofuran; methanol / 1 h / -15 °C 4: Et₃N / tetrahydrofuran / 14 h / 20 °C 5: 2.53 g / 1,8-diazabicyclo[5,4,0]undec-7-ene / tetrahydrofuran / 0.17 h / Heating 6: 100 percent / aq. HCl / ethyl acetate / 0.5 h / 80 °C 7: 56 percent / aq. K₂CO₃; Pd(PPh₃)4 / toluene; ethanol / Heating 8: 100 percent / triacetoxyborohydride / 1,2-dichloro-ethane / 20 °C 9: 87 percent / aq. NaOH / tetrahydrofuran; methanol / 20 °C 10: SOCl₂; DMF / tetrahydrofuran / 20 °C

Reference： [1]Seto, Masaki; Aramaki, Yoshio; Okawa, Tomohiro; Miyamoto, Naoki; Aikawa, Katsuji; Kanzaki, Naoyuki; Niwa, Shin-Ichi; Iizawa, Yuji; Baba, Masanori; Shiraishi, Mitsuru [Chemical and Pharmaceutical Bulletin, 2004, vol. 52, # 5, p. 577 - 590]

35
[ 3951-89-1 ]
[ 313729-92-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 9 steps 1: DMAP / tetrahydrofuran / 1.5 h / Heating 2: 3.89 g / sodium methoxide / 2.5 h / Heating 3: NaBH₄ / tetrahydrofuran; methanol / 1 h / -15 °C 4: Et₃N / tetrahydrofuran / 14 h / 20 °C 5: 2.53 g / 1,8-diazabicyclo[5,4,0]undec-7-ene / tetrahydrofuran / 0.17 h / Heating 6: 100 percent / aq. HCl / ethyl acetate / 0.5 h / 80 °C 7: 56 percent / aq. K₂CO₃; Pd(PPh₃)4 / toluene; ethanol / Heating 8: 100 percent / triacetoxyborohydride / 1,2-dichloro-ethane / 20 °C 9: 87 percent / aq. NaOH / tetrahydrofuran; methanol / 20 °C

Reference： [1]Seto, Masaki; Aramaki, Yoshio; Okawa, Tomohiro; Miyamoto, Naoki; Aikawa, Katsuji; Kanzaki, Naoyuki; Niwa, Shin-Ichi; Iizawa, Yuji; Baba, Masanori; Shiraishi, Mitsuru [Chemical and Pharmaceutical Bulletin, 2004, vol. 52, # 5, p. 577 - 590]

36
[ 3951-89-1 ]
7-[4-(2-butoxy-ethoxy)-phenyl]-1-(1-methyl-1H-pyrazol-4-ylmethyl)-2,3-dihydro-1H-benzo[b]azepine-4-carbonyl chloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 10 steps 1: DMAP / tetrahydrofuran / 1.5 h / Heating 2: 3.89 g / sodium methoxide / 2.5 h / Heating 3: NaBH₄ / tetrahydrofuran; methanol / 1 h / -15 °C 4: Et₃N / tetrahydrofuran / 14 h / 20 °C 5: 2.53 g / 1,8-diazabicyclo[5,4,0]undec-7-ene / tetrahydrofuran / 0.17 h / Heating 6: 100 percent / aq. HCl / ethyl acetate / 0.5 h / 80 °C 7: 56 percent / aq. K₂CO₃; Pd(PPh₃)4 / toluene; ethanol / Heating 8: 63 percent / triacetoxyborohydride / 1,2-dichloro-ethane / 20 °C 9: 69 percent / aq. NaOH / tetrahydrofuran; methanol / 20 °C 10: SOCl₂; DMF / tetrahydrofuran / 20 °C

Reference： [1]Seto, Masaki; Aramaki, Yoshio; Okawa, Tomohiro; Miyamoto, Naoki; Aikawa, Katsuji; Kanzaki, Naoyuki; Niwa, Shin-Ichi; Iizawa, Yuji; Baba, Masanori; Shiraishi, Mitsuru [Chemical and Pharmaceutical Bulletin, 2004, vol. 52, # 5, p. 577 - 590]

37
[ 3951-89-1 ]
[ 313751-84-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 9 steps 1: DMAP / tetrahydrofuran / 1.5 h / Heating 2: 3.89 g / sodium methoxide / 2.5 h / Heating 3: NaBH₄ / tetrahydrofuran; methanol / 1 h / -15 °C 4: Et₃N / tetrahydrofuran / 14 h / 20 °C 5: 2.53 g / 1,8-diazabicyclo[5,4,0]undec-7-ene / tetrahydrofuran / 0.17 h / Heating 6: 100 percent / aq. HCl / ethyl acetate / 0.5 h / 80 °C 7: 56 percent / aq. K₂CO₃; Pd(PPh₃)4 / toluene; ethanol / Heating 8: 59 percent / triacetoxyborohydride / 1,2-dichloro-ethane / 20 °C 9: 80 percent / aq. NaOH / tetrahydrofuran; methanol / 20 °C

Reference： [1]Seto, Masaki; Aramaki, Yoshio; Okawa, Tomohiro; Miyamoto, Naoki; Aikawa, Katsuji; Kanzaki, Naoyuki; Niwa, Shin-Ichi; Iizawa, Yuji; Baba, Masanori; Shiraishi, Mitsuru [Chemical and Pharmaceutical Bulletin, 2004, vol. 52, # 5, p. 577 - 590]

38
[ 3951-89-1 ]
[ 313751-95-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 9 steps 1: DMAP / tetrahydrofuran / 1.5 h / Heating 2: 3.89 g / sodium methoxide / 2.5 h / Heating 3: NaBH₄ / tetrahydrofuran; methanol / 1 h / -15 °C 4: Et₃N / tetrahydrofuran / 14 h / 20 °C 5: 2.53 g / 1,8-diazabicyclo[5,4,0]undec-7-ene / tetrahydrofuran / 0.17 h / Heating 6: 100 percent / aq. HCl / ethyl acetate / 0.5 h / 80 °C 7: 56 percent / aq. K₂CO₃; Pd(PPh₃)4 / toluene; ethanol / Heating 8: 63 percent / triacetoxyborohydride / 1,2-dichloro-ethane / 20 °C 9: 69 percent / aq. NaOH / tetrahydrofuran; methanol / 20 °C

Reference： [1]Seto, Masaki; Aramaki, Yoshio; Okawa, Tomohiro; Miyamoto, Naoki; Aikawa, Katsuji; Kanzaki, Naoyuki; Niwa, Shin-Ichi; Iizawa, Yuji; Baba, Masanori; Shiraishi, Mitsuru [Chemical and Pharmaceutical Bulletin, 2004, vol. 52, # 5, p. 577 - 590]

39
[ 3951-89-1 ]
7-[4-(2-butoxy-ethoxy)-phenyl]-1-(2-methyl-2H-pyrazol-3-ylmethyl)-2,3-dihydro-1H-benzo[b]azepine-4-carbonyl chloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 10 steps 1: DMAP / tetrahydrofuran / 1.5 h / Heating 2: 3.89 g / sodium methoxide / 2.5 h / Heating 3: NaBH₄ / tetrahydrofuran; methanol / 1 h / -15 °C 4: Et₃N / tetrahydrofuran / 14 h / 20 °C 5: 2.53 g / 1,8-diazabicyclo[5,4,0]undec-7-ene / tetrahydrofuran / 0.17 h / Heating 6: 100 percent / aq. HCl / ethyl acetate / 0.5 h / 80 °C 7: 56 percent / aq. K₂CO₃; Pd(PPh₃)4 / toluene; ethanol / Heating 8: 67 percent / triacetoxyborohydride / 1,2-dichloro-ethane / 20 °C 9: 77 percent / aq. NaOH / tetrahydrofuran; methanol / 20 °C 10: SOCl₂; DMF / tetrahydrofuran / 20 °C

Reference： [1]Seto, Masaki; Aramaki, Yoshio; Okawa, Tomohiro; Miyamoto, Naoki; Aikawa, Katsuji; Kanzaki, Naoyuki; Niwa, Shin-Ichi; Iizawa, Yuji; Baba, Masanori; Shiraishi, Mitsuru [Chemical and Pharmaceutical Bulletin, 2004, vol. 52, # 5, p. 577 - 590]

40
[ 52727-57-8 ]
[ 3951-89-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: 88 percent / pyridine / 1 h / 55 °C 2.1: NaH / dimethylformamide / 1 h / 20 °C 2.2: NaI / dimethylformamide / 14 h / 80 °C 3.1: 25.1 g / NaH / dimethylformamide / 15 h / 80 °C 4.1: 21 percent / H₂SO₄; AcOH / 2.5 h / 90 °C
	Multi-step reaction with 2 steps 1.1: 5 h / 25 - 55 °C 2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 2 h / 0 - 25 °C / Inert atmosphere 2.2: 60 h / 0 - 80 °C / Inert atmosphere 2.3: 15 h / 0 - 80 °C

Reference： [1]Seto, Masaki; Aramaki, Yoshio; Okawa, Tomohiro; Miyamoto, Naoki; Aikawa, Katsuji; Kanzaki, Naoyuki; Niwa, Shin-Ichi; Iizawa, Yuji; Baba, Masanori; Shiraishi, Mitsuru [Chemical and Pharmaceutical Bulletin, 2004, vol. 52, # 5, p. 577 - 590]
[2]Current Patent Assignee: SHENZHEN LINGFANG BIO MEDICINE TECH; SHENZHEN LINGFANG BIOTECH; WUXI APPTEC CO., LTD. - EP3988098, 2022, A1

41
[ 3951-89-1 ]
[ 123-38-6 ]
7-bromo-1-propyl-2,3,4,5-tetrahydro-1H-1-benzazepine-5-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium tris(acetoxy)borohydride; acetic acid In 1,2-dichloro-ethane at 20℃; for 6h;

Reference： [1]Current Patent Assignee: TAKEDA PHARMACEUTICAL COMPANY LIMITED - EP1186604, 2002, A1 Location in patent: Page 141

42
None [ No CAS ]
[ 3951-89-1 ]

Yield	Reaction Conditions	Operation in experiment
	With sulfuric acid; acetic acid at 80℃; for 2.5h;

Reference： [1]Current Patent Assignee: TAKEDA PHARMACEUTICAL COMPANY LIMITED - EP1186604, 2002, A1 Location in patent: Page 32

43
[ 3951-89-1 ]
[ 108-23-6 ]
[ 872624-48-1 ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine In dichloromethane at 0℃; for 1.5h;	1.3 Step 3; Preparation of (+/-)-Isopropyl 7-bromo-5-oxo-2,3,4,5-tetrahydrobenzo[&]azepine-1-carboxylate; Add a solution of methyl 5-bromo-2-[methoxycarbonylpropyl)amino] benzoate (11.7 g,28.1 mmol) in toluene (100 mL) to a suspension of potassium tert-butoxide (6.31 g, 56.2mmol) in toluene (100 mL) at 70 °C under an atmosphere of nitrogen over a period of 30min. After 15 min, cool the mixture to room temperature and pour the suspension into icewater (500 mL). Adjust the pH of the solution to pH = 3 with 2 N hydrochloric acid (25mL) and separate the layers. Extract the aqueous layer with ethyl acetate (3 x 200 mL)and combine the organic extracts. Dry the organic layer over anhydrous sodium sulfate,filter, and remove the solvent under reduced pressure to provide (+/-)-l-isopropyl-4-methyl-7-bromo-5-oxo-2,3,4,5-tetrahydrobenzo [Z7]azepine-l,4-dicarboxylate as anorange oil (10.5 g, 98% crude). Dissolve (+/-)-1-isopropyl-4-methyl-7-bromo-5-oxo-2,3,4,5-tetrahydrobenzo [&]azepine~l,4-dicarboxylate (10.5 g, 27.3 mmol) in glacialacetic acid (100 mL) and add water (10 mL) followed by concentrated hydrochloric acid(35 mL) and heat the resulting solution at reflux for 1 h. Cool the mixture to roomtemperature and pour into ice water (500 mL). Adjust the to pH = 8 with potassiumhydroxide (85 g) in water (200 mL), and extract the mixture with ethyl acetate (3 x 150mL) and combine the organic extracts. Dry the organic layer over anhydrous sodiumsulfate, filter, and remove the solvent under reduced pressure. Dissolve the crudematerial (12.0 g) in dichloromethane (30 mL) and cool to 0 °C. To the solution addpyridine (2.0 mL, 25.5 mmol) followed by dropwise addition of 1.0 M solution ofisopropyl chloroformate in toluene (19.1 mL, 19.1 mmol) and stir for 1.5 h. Pour thereaction into water (100 mL) and separate the layers. Extract the aqueous layer withdichloromethane (2 x 40 mL) and combine the organic extracts and wash with 2 Nhydrochloric acid, saturated sodium hydrogen carbonate, and brine (80 mL each). Drythe organic layer over anhydrous sodium sulfate, filter, and remove the solvent underreduced pressure. Chromatograph the residue over silica gel eluting with hexanes/ethylacetate (60:40), to afford the title compound as a yellow solid (3.5 g, 40% over threesteps).

Reference： [1]Current Patent Assignee: ELI LILLY & CO - WO2006/2342, 2006, A1 Location in patent: Page/Page column 49-50

44
[ 872624-49-2 ]
[ 3951-89-1 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: (+/-)-1-isopropyl-4-methyl-7-bromo-5-oxo-2,3,4,5-tetrahydrobenzo[b]azepine-1,4-dicarboxylate With hydrogenchloride; water; acetic acid for 1h; Heating / reflux; Stage #2: With potassium hydroxide In water	1.3 Step 3; Preparation of (+/-)-Isopropyl 7-bromo-5-oxo-2,3,4,5-tetrahydrobenzo[&]azepine-1-carboxylate; Add a solution of methyl 5-bromo-2-[methoxycarbonylpropyl)amino] benzoate (11.7 g,28.1 mmol) in toluene (100 mL) to a suspension of potassium tert-butoxide (6.31 g, 56.2mmol) in toluene (100 mL) at 70 °C under an atmosphere of nitrogen over a period of 30min. After 15 min, cool the mixture to room temperature and pour the suspension into icewater (500 mL). Adjust the pH of the solution to pH = 3 with 2 N hydrochloric acid (25mL) and separate the layers. Extract the aqueous layer with ethyl acetate (3 x 200 mL)and combine the organic extracts. Dry the organic layer over anhydrous sodium sulfate,filter, and remove the solvent under reduced pressure to provide (+/-)-l-isopropyl-4-methyl-7-bromo-5-oxo-2,3,4,5-tetrahydrobenzo [Z7]azepine-l,4-dicarboxylate as anorange oil (10.5 g, 98% crude). Dissolve (+/-)-1-isopropyl-4-methyl-7-bromo-5-oxo-2,3,4,5-tetrahydrobenzo [&]azepine~l,4-dicarboxylate (10.5 g, 27.3 mmol) in glacialacetic acid (100 mL) and add water (10 mL) followed by concentrated hydrochloric acid(35 mL) and heat the resulting solution at reflux for 1 h. Cool the mixture to roomtemperature and pour into ice water (500 mL). Adjust the to pH = 8 with potassiumhydroxide (85 g) in water (200 mL), and extract the mixture with ethyl acetate (3 x 150mL) and combine the organic extracts. Dry the organic layer over anhydrous sodiumsulfate, filter, and remove the solvent under reduced pressure. Dissolve the crudematerial (12.0 g) in dichloromethane (30 mL) and cool to 0 °C. To the solution addpyridine (2.0 mL, 25.5 mmol) followed by dropwise addition of 1.0 M solution ofisopropyl chloroformate in toluene (19.1 mL, 19.1 mmol) and stir for 1.5 h. Pour thereaction into water (100 mL) and separate the layers. Extract the aqueous layer withdichloromethane (2 x 40 mL) and combine the organic extracts and wash with 2 Nhydrochloric acid, saturated sodium hydrogen carbonate, and brine (80 mL each). Drythe organic layer over anhydrous sodium sulfate, filter, and remove the solvent underreduced pressure. Chromatograph the residue over silica gel eluting with hexanes/ethylacetate (60:40), to afford the title compound as a yellow solid (3.5 g, 40% over threesteps).

Reference： [1]Current Patent Assignee: ELI LILLY & CO - WO2006/2342, 2006, A1 Location in patent: Page/Page column 49-50

45
[ 3951-89-1 ]
[ 124-41-4 ]
[ 124-63-0 ]
methyl 7-bromo-1-methoxycarbonyl-2,3-dihydro-1H-1-benzazepine-4-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 7-bromo-1,2,3,4-tetrahydro-5H-1-benzazepin-5-one; sodium methylate In carbonic acid dimethyl ester for 8h; Heating / reflux; Stage #2: With methanol; sodium tetrahydroborate In tetrahydrofuran at -15℃; for 1h; Stage #3: methanesulfonyl chloride With 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine more than 3 stages;

Reference： [1]Current Patent Assignee: TAKEDA PHARMACEUTICAL COMPANY LIMITED - EP1186604, 2002, A1 Location in patent: Page 43

46
[ 3951-89-1 ]
7-[4-(2-butoxy-ethoxy)-phenyl]-1-propyl-2,3-dihydro-1H-benzo[b]azepine-4-carbonyl chloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: sodium tris(acetoxy)borohydride; acetic acid / 1,2-dichloro-ethane / 6 h / 20 °C 2.1: potassium carbonate / ethanol; water; toluene / 1 h / 20 °C 2.2: 3 h / Heating / reflux 3.1: lithium hexamethyldisilazane / tetrahydrofuran; hexane / 2 h / -78 °C 3.2: 2 h / 20 °C 4.1: thionyl chloride / N,N-dimethyl-formamide / tetrahydrofuran / 1 h / 20 °C

Reference： [1]Current Patent Assignee: TAKEDA PHARMACEUTICAL COMPANY LIMITED - EP1186604, 2002, A1

47
[ 3951-89-1 ]
7-[4-(2-butoxyethoxy)phenyl]-1-propyl-N-[4-[[N-methyl-N-(tetrahydropyran-4-yl)amino]methyl]phenyl]-2,3-dihydro-1H-1-benzazepine-4-carboxamide dihydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1.1: sodium tris(acetoxy)borohydride; acetic acid / 1,2-dichloro-ethane / 6 h / 20 °C 2.1: potassium carbonate / ethanol; water; toluene / 1 h / 20 °C 2.2: 3 h / Heating / reflux 3.1: lithium hexamethyldisilazane / tetrahydrofuran; hexane / 2 h / -78 °C 3.2: 2 h / 20 °C 4.1: thionyl chloride / N,N-dimethyl-formamide / tetrahydrofuran / 1 h / 20 °C 5.1: triethylamine / tetrahydrofuran; DMF (N,N-dimethyl-formamide) / 16 h / 0 - 20 °C 6.1: hydrogenchloride / ethyl acetate / 1 h / 20 °C

Reference： [1]Current Patent Assignee: TAKEDA PHARMACEUTICAL COMPANY LIMITED - EP1186604, 2002, A1

48
[ 3951-89-1 ]
7-[4-(2-butoxyethoxy)phenyl]-1-propyl-N-[4-[[N-methyl-N-(tetrahydropyran-4-yl)amino]methyl]phenyl]-2,3-dihydro-1H-1-benzazepine-4-carboxamide fumarate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1.1: sodium tris(acetoxy)borohydride; acetic acid / 1,2-dichloro-ethane / 6 h / 20 °C 2.1: potassium carbonate / ethanol; water; toluene / 1 h / 20 °C 2.2: 3 h / Heating / reflux 3.1: lithium hexamethyldisilazane / tetrahydrofuran; hexane / 2 h / -78 °C 3.2: 2 h / 20 °C 4.1: thionyl chloride / N,N-dimethyl-formamide / tetrahydrofuran / 1 h / 20 °C 5.1: triethylamine / tetrahydrofuran; DMF (N,N-dimethyl-formamide) / 16 h / 0 - 20 °C 6.1: 2-butenedioic acid / ethanol / 0.5 h / 20 °C

Reference： [1]Current Patent Assignee: TAKEDA PHARMACEUTICAL COMPANY LIMITED - EP1186604, 2002, A1

49
[ 3951-89-1 ]
[ 313740-83-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1.1: sodium tris(acetoxy)borohydride; acetic acid / 1,2-dichloro-ethane / 6 h / 20 °C 2.1: potassium carbonate / ethanol; water; toluene / 1 h / 20 °C 2.2: 3 h / Heating / reflux 3.1: lithium hexamethyldisilazane / tetrahydrofuran; hexane / 2 h / -78 °C 3.2: 2 h / 20 °C 4.1: thionyl chloride / N,N-dimethyl-formamide / tetrahydrofuran / 1 h / 20 °C 5.1: triethylamine / tetrahydrofuran; DMF (N,N-dimethyl-formamide) / 16 h / 0 - 20 °C

Reference： [1]Current Patent Assignee: TAKEDA PHARMACEUTICAL COMPANY LIMITED - EP1186604, 2002, A1

50
[ 2969-81-5 ]
[ 223526-84-9 ]
[ 3951-89-1 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: methyl 5-bromo-2-[(4-methylphenylsulfonyl)amino]benzoate With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 25℃; for 2h; Inert atmosphere; Stage #2: ethyl 4-bromobutanoate With sodium iodide In N,N-dimethyl-formamide; mineral oil at 0 - 80℃; for 60h; Inert atmosphere; Stage #3: With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 80℃; for 15h;	2.2 Step 2: Synthesis of compound BB-1B-3 Sodium hydrogen (6.14g, 60% purity) and DMF (50 mL) were added to a solution of BB-1B-2 (59 g) in DMF (200 mL) at 0 °C , and then stirred at 25 °C under the atmosphere of nitrogen for 2 hours, sodium iodide (23.02 g) and ethyl 4-bromobutyrate (32.95 g) were added thereto at 0 °C and stirred at 80 °C under the atmosphere of nitrogen for 16 hours, and then sodium hydrogen (6.14 g, 60% purity) and DMF (50 mL) were added thereto at 0°C and stirred at 80°C under the atmosphere of nitrogen for 15 hours. The mixture was added with water (200 mL) and extracted with ethyl acetate (50 mL×3). The combined organic layer was washed with saturated brine (200 mL), dried with anhydrous sodium sulfate, and filtered and evaporated under reduced pressure to obtain a yellow oil. Concentrated sulfuric acid (100 mL, 98% purity) and acetic acid (157.5 g) were add to the yellow oil at 0° and stirred at 90°C for 2.5 hours. The mixture was adjusted to pH = 8 with 12 mol/L sodium hydroxide in aqueous solution and then extracted with ethyl acetate (300 mL×3), and washed with saturated brine (300 mL) to combine organic layers. The combined organic layer was dried with anhydrous sodium sulfate, and filtered and evaporated under reduced pressure to obtain a residue. The residue was purified with a silica gel column (petroleum ether/ethyl acetate = 50:1 to 5:1) to obtain BB-1B-3.
	Stage #1: methyl 5-bromo-2-[(4-methylphenylsulfonyl)amino]benzoate With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 25℃; for 2h; Inert atmosphere; Stage #2: ethyl 4-bromobutanoate With sodium iodide In N,N-dimethyl-formamide; mineral oil at 0 - 80℃; for 60h; Inert atmosphere; Stage #3: With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 80℃; for 15h;	2.2 Step 2: Synthesis of compound BB-1B-3 Sodium hydrogen (6.14g, 60% purity) and DMF (50 mL) were added to a solution of BB-1B-2 (59 g) in DMF (200 mL) at 0 °C , and then stirred at 25 °C under the atmosphere of nitrogen for 2 hours, sodium iodide (23.02 g) and ethyl 4-bromobutyrate (32.95 g) were added thereto at 0 °C and stirred at 80 °C under the atmosphere of nitrogen for 16 hours, and then sodium hydrogen (6.14 g, 60% purity) and DMF (50 mL) were added thereto at 0°C and stirred at 80°C under the atmosphere of nitrogen for 15 hours. The mixture was added with water (200 mL) and extracted with ethyl acetate (50 mL×3). The combined organic layer was washed with saturated brine (200 mL), dried with anhydrous sodium sulfate, and filtered and evaporated under reduced pressure to obtain a yellow oil. Concentrated sulfuric acid (100 mL, 98% purity) and acetic acid (157.5 g) were add to the yellow oil at 0° and stirred at 90°C for 2.5 hours. The mixture was adjusted to pH = 8 with 12 mol/L sodium hydroxide in aqueous solution and then extracted with ethyl acetate (300 mL×3), and washed with saturated brine (300 mL) to combine organic layers. The combined organic layer was dried with anhydrous sodium sulfate, and filtered and evaporated under reduced pressure to obtain a residue. The residue was purified with a silica gel column (petroleum ether/ethyl acetate = 50:1 to 5:1) to obtain BB-1B-3.

Reference： [1]Current Patent Assignee: SHENZHEN LINGFANG BIO MEDICINE TECH; SHENZHEN LINGFANG BIOTECH; WUXI APPTEC CO., LTD. - EP3988098, 2022, A1 Location in patent: Paragraph 0077; 0079
[2]Current Patent Assignee: SHENZHEN LINGFANG BIO MEDICINE TECH; SHENZHEN LINGFANG BIOTECH; WUXI APPTEC CO., LTD. - EP3988098, 2022, A1 Location in patent: Paragraph 0077; 0079

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CAS No. :	3951-89-1	MDL No. :	MFCD02168781
Formula :	C₁₀H₁₀BrNO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	XIFKOJPBXZKSAZ-UHFFFAOYSA-N
M.W :	240.10	Pubchem ID :	22329108
Synonyms :

Signal Word:	Warning	Class:
Precautionary Statements:	P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313	UN#:
Hazard Statements:	H315-H319	Packing Group:
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. 3951-89-1 ]

Quality Control of [ 3951-89-1 ]

Related Doc. of [ 3951-89-1 ]

Product Details of [ 3951-89-1 ]

Safety of [ 3951-89-1 ]

Application In Synthesis of [ 3951-89-1 ]

[ 3951-89-1 ] Synthesis Path-Downstream 1~50

Related Functional Groups of
[ 3951-89-1 ]

Bromides

Ketones

Related Parent Nucleus of
[ 3951-89-1 ]

Other Aromatic Heterocycles

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

[ CAS No. 3951-89-1 ]

Quality Control of [ 3951-89-1 ]

Related Doc. of [ 3951-89-1 ]

Product Details of [ 3951-89-1 ]

Safety of [ 3951-89-1 ]

Application In Synthesis of [ 3951-89-1 ]

[ 3951-89-1 ] Synthesis Path-Downstream 1~50

Related Functional Groups of [ 3951-89-1 ]

Bromides

Ketones

Related Parent Nucleus of [ 3951-89-1 ]

Other Aromatic Heterocycles

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 3951-89-1 ]

Related Parent Nucleus of
[ 3951-89-1 ]