[ CAS No. 527-73-1 ] {[proInfo.proName]}

Name: 527-73-1|2-Nitroimidazole|99%
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Quality Control of [ 527-73-1 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 527-73-1 ]

Product Details of [ 527-73-1 ]

CAS No. :	527-73-1	MDL No. :	MFCD00005185
Formula :	C₃H₃N₃O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	YZEUHQHUFTYLPH-UHFFFAOYSA-N
M.W :	113.07	Pubchem ID :	10701
Synonyms :	2-Nitroimidazole

Calculated chemistry of [ 527-73-1 ]

Physicochemical Properties

Num. heavy atoms :	8
Num. arom. heavy atoms :	5
Fraction Csp3 :	0.0
Num. rotatable bonds :	1
Num. H-bond acceptors :	3.0
Num. H-bond donors :	1.0
Molar Refractivity :	27.41
TPSA :	74.5 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.83 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.21
Log Po/w (XLOGP3) :	0.22
Log Po/w (WLOGP) :	0.32
Log Po/w (MLOGP) :	-0.4
Log Po/w (SILICOS-IT) :	-0.86
Consensus Log Po/w :	-0.1

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	2.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-1.08
Solubility :	9.49 mg/ml ; 0.0839 mol/l
Class :	Very soluble
Log S (Ali) :	-1.34
Solubility :	5.12 mg/ml ; 0.0453 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-0.56
Solubility :	31.2 mg/ml ; 0.276 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	2.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.95

Safety of [ 527-73-1 ]

Signal Word:	Danger	Class:	6.1
Precautionary Statements:	P261-P301+P310-P305+P351+P338	UN#:	2811
Hazard Statements:	H301-H315-H319-H335	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 527-73-1 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 527-73-1 ]
Downstream synthetic route of [ 527-73-1 ]

[ 527-73-1 ] Synthesis Path-Upstream 1~8

1
[ 527-73-1 ]
[ 7720-39-0 ]

Reference： [1] RSC Advances, 2014, vol. 4, # 43, p. 22567 - 22574
[2] Patent: WO2018/160891, 2018, A1, . Location in patent: Page/Page column 497-498

2
[ 527-73-1 ]
[ 7720-39-0 ]
[ 102998-00-5 ]

Reference： [1] Journal of the American Chemical Society, 1987, vol. 109, # 14, p. 4308 - 4314

3
[ 42383-61-9 ]
[ 527-73-1 ]

Yield	Reaction Conditions	Operation in experiment
65%	Stage #1: With sodium nitrite In tetrafluoroboric acid; water; acetone at -20 - -10℃; Stage #2: With copper(II) sulfate; sodium nitrite In tetrafluoroboric acid; water; acetone at 20℃; for 2 h;	2-Aminoimidazole sulfate (1.57 g, 6.01 mmol) was dissolved in water (10 mL) and fluoboric acid (50percent w/v, 7 mL). The solution was cooled to -20 °C in an acetone/dry ice bath, and a solution of sodium nitrite (4.14 g, 59.6 mmol) in water (10 mL) was added dropwise to it. The solution was stirred at -10 °C for 30 min, then poured into a solution of CuSO4 (20.0 g, 119 mmol) in water (200 mL). Additional sodium nitrite (4.14 g, 59.6 mmol) was added and the mixture was stirred at room temperature for 2 h. The solution was extracted with EtOAc (200 mL) in a continuous extractor for 6 h. The organic extract was evaporated in vacuo, and the residue was recrystallized from ethanol to afford compound 4 as yellow needles (870 mg, 65percent)

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 17, p. 5102 - 5106

4
[ 7720-39-0 ]
[ 527-73-1 ]

Reference： [1] Organic Process Research and Development, 2014, vol. 18, # 7, p. 886 - 890
[2] Organic Mass Spectrometry, 1982, vol. 17, # 7, p. 299 - 303

5
[ 15469-97-3 ]
[ 527-73-1 ]

Reference： [1] Inorganic Chemistry Communications, 2017, vol. 78, p. 32 - 36
[2] Journal of Heterocyclic Chemistry, 1982, vol. 19, p. 253 - 256

6
[ 527-73-1 ]
[ 74-88-4 ]
[ 1671-82-5 ]

Yield	Reaction Conditions	Operation in experiment
100%	With caesium carbonate In N,N-dimethyl-formamide at 50℃; Inert atmosphere	To a stirred solution of 2-nitro-lH- imidazole (500 mg, 4.42 mmol) in DMF (6 mL) was added CS₂CO₃ (4.3 g, 13.3 mmol) before introduction of Mel (942 mg, 6.63 mmol). The resulting mixture was heated to 50°C under N₂ overnight. The reaction was quenched with aqueous NaHCC>₃ (sat.) and extracted with EA (25 mL x 3). The combined organic layers was dried over Na₂S0₄, filtered and concentrated. The crude product was purified by flash chromatography (silica gel, 0-50percent ethyl acetate in petroleum ether) to provide l-methyl-2-nitro-lH-imidazole (542-1) (530 mg, 100 percent) as a yellow solid. LC-MS (ESI): m/z (M+\) 128.1

Reference： [1] Patent: WO2016/4272, 2016, A1, . Location in patent: Paragraph 00798

7
[ 527-73-1 ]
[ 4637-24-5 ]
[ 1671-82-5 ]

Yield	Reaction Conditions	Operation in experiment
93.5%	at 80℃; for 2 h;	To 2-nitro-(1H)-imidazole (2.0 g, 17.7 mmol)N,N-dimethylformamide dimethyl acetal (8.4 g, 70.7 mmol) was added dropwise to a solution of DMF (10 ml).The reaction was carried out at 80 ° C for 2 h. Add water (30ml) and ethyl acetate (25ml),The mixture was extracted with ethyl acetate (25×2 mL).Dry over anhydrous sodium sulfate, filter, and concentrate the filtrate under reduced pressure.The crude product was separated by column chromatography (eluent: dichloromethane: anhydrous methanol = 30:1).A pale yellow solid (2.1 g, 93.5percent) was obtained.The product purity is 99.7percent (mass fraction)

Reference： [1] Patent: CN108503583, 2018, A, . Location in patent: Paragraph 0051-0053; 0059; 0060

8
[ 527-73-1 ]
[ 77-78-1 ]
[ 1671-82-5 ]

Reference： [1] New Journal of Chemistry, 2006, vol. 30, # 3, p. 349 - 358

[ 527-73-1 ] Synthesis Path-Downstream 1~40

1
[ 7720-39-0 ]
[ 527-73-1 ]

Reference： [1]Organic Process Research and Development,2014,vol. 18,p. 886 - 890
[2]Organic Mass Spectrometry,1982,vol. 17,p. 299 - 303

2
[ 2508-01-2 ]
[ 527-73-1 ]
[ 131504-99-9 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate 1.) DMF, 60 deg C, 0.5 h, 2.) 60 deg C, 18 h; Yield given. Multistep reaction;

Reference： [1]Suto, Mark J.; Stier, Michael A.; Werbel, Leslie M. [Journal of Medicinal Chemistry, 1991, vol. 34, # 3, p. 1207 - 1209]

3
[ 527-73-1 ]
[ 5455-98-1 ]
[ 93272-45-8 ]

Yield	Reaction Conditions	Operation in experiment
75.65%	With potassium carbonate In ethanol for 8h; Reflux;	2.2.1. Synthesis of 2-(2-hydroxy-3-(2-nitro-1H-imidazol-1-yl)propyl)isoindoline-1,3-dione (3) Anhydrous potassium carbonate (1.0 mmol, 140 mg) wasadded to a stirred slurry of (1) (10.1 mmol, 2050 mg) and (2)(10.4 mmol, 1170 mg) in ethanol (100 mL) and the reactionmixture was heated under reflux for 8 hours. The reactionmixture was yellow and clarified gradually. After the reactionwas complete, as monitored by thin-layer chromatography(TLC), the mixture was allowed to come to room temperatureand a yellowish solid was obtained by filtration. Theresidue was washed with hot ethanol (3 10 mL). Compound(3) was obtained and dried under vacuum. The productweighted 2410 mg, giving a yield 75.65%.1H-NMR (400 MHz, DMSO-d6) 7.92 - 7.80 (m, 4H),7.60 (s, 1H), 7.13 (s, 1H), 5.51 (d, J = 5.6 Hz, 1H), 4.59 (dd,J = 13.6, 2.8 Hz, 1H), 4.26 (dd, J = 13.8, 8.9 Hz, 1H), 4.06(s, 1H), 3.61 (qd, J = 13.8, 6.5 Hz, 2H). MS (ESI):[M+H]+317.08, found 317.0.
59%	With potassium carbonate In ethanol for 6h; Heating;
	With potassium carbonate In ethanol for 6h; Heating / reflux;	1.A A. A. Preparation of 2-[2-Hydroxy-2-(nitro-1H-imidazole-1-yl)ethyl]-1H-isoindole-1,3(2H)-dione. To a solution of N-(2,3-epoxypropyl)phthalimide (commercially available, 25.0 g, 0. 123 mol) in ethanol (200 mL) 2-nitroimidazole (commercially available, 14.5 g, 0.128 mol) and potassium carbonate (1.5 g) were added and the reaction mixture was heated under reflux for about 6 hours during which time a light yellow solid formed. The reaction mixture was cooled and the yellow solid obtained was filtered and dried. m.p. 213-14° C.

With potassium carbonate In ethanol

20.A A. A. Preparation of 1-(3-Phthalimido-2-hydroxy propyl)-2-nitroimidazole To a solution of N-(2,3-epoxypropyl)phthalimide (commercially available, 20.3 g, 0.1 mol) in ethanol (200 mL), 2-nitroimidazole (11.3 g, 0.1 mol) and potassium carbonate (1.2 g) were added and the reaction mixture was refluxed for 6 hrs. The reaction mixture was cooled and poured into water (700 ml) and the yellow solid formed was filtered and dried. Yield 28.2 g (89%). It was recrystallized from methanol. mp. 213°-214° C. 1 H NMR (DMSO) δ3.62 (m, 4H, PhthNCH2 CHOH), 4.08 (m, 1H, CHOH), 4.32 and 4.63 (m, 2H, CHOHCH2 N+ =317+ Anal. Calcd. for C14 H12 N4 O5: C, 53.17; H, 3.82; N, 17.71. Found C, 53.11; H, 3.76; N, 17.49.

Reference： [1]Wang, Feng; Fan, Di; Qian, Jun; Zhang, Zhe; Zhu, Jianhua; Chen, Jian [Medicinal Chemistry, 2015, vol. 11, # 7, p. 649 - 655]
[2]Ahmed; Stratford; Jenkins [Arzneimittel-Forschung/Drug Research, 1985, vol. 35, # 12, p. 1763 - 1768]
[3]Current Patent Assignee: BRACCO SPA - US2005/74402, 2005, A1 Location in patent: Page/Page column 6
[4]Current Patent Assignee: BRACCO SPA - US5608110, 1997, A

4
[ 527-73-1 ]
[ 45223-18-5 ]
[ 137046-49-2 ]

Yield	Reaction Conditions	Operation in experiment
74%	With potassium hydroxide; 18-crown-6 ether 2) MeCN, reflux;

Reference： [1]Long; Parrick; Hodgkiss [Synthesis, 1991, # 9, p. 709 - 713]

5
[ 527-73-1 ]
[ 35231-44-8 ]
[ 133932-24-8 ]

Reference： [1]Journal of Medicinal Chemistry,1991,vol. 34,p. 2268 - 2274

6
[ 527-73-1 ]
[ 7720-39-0 ]
[ 102998-00-5 ]
2-amino-4,5-dihydro-4,5-dihydroxyimidazolium chloride [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1987,vol. 109,p. 4308 - 4314

7
[ 15469-97-3 ]
[ 527-73-1 ]

Reference： [1]Inorganic Chemistry Communications,2017,vol. 78,p. 32 - 36
[2]Journal of Heterocyclic Chemistry,1982,vol. 19,p. 253 - 256

8
[ 527-73-1 ]
[ 3101-60-8 ]
[ 188264-54-2 ]

Reference： [1]Bioorganic and Medicinal Chemistry,1997,vol. 5,p. 591 - 599

9
[ 527-73-1 ]
[ 157665-52-6 ]
[ 197089-32-0 ]

Yield	Reaction Conditions	Operation in experiment
57%	With sodium hydride In dimethyl sulfoxide at 100℃; for 18h;

Reference： [1]Howes, Peter D.; Cleasby, Anne; Evans, Derek N.; Feilden, Helen; Smith, Paul W.; Sollis, Steven L.; Taylor, Neil; Wonacott, Alan J. [European Journal of Medicinal Chemistry, 1999, vol. 34, # 3, p. 225 - 234]

10
[ 527-73-1 ]
[ 77-78-1 ]
[ 1671-82-5 ]

Reference： [1]New Journal of Chemistry,2006,vol. 30,p. 349 - 358

11
[ 527-73-1 ]
[ 13515-76-9 ]
[ 600157-66-2 ]

Yield	Reaction Conditions	Operation in experiment
44%	With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 18 - 25℃; for 5h;	Method 24; Methyl 3-(2-nitro-1H-imidazol-1-yl)-N-trityl-L-alaninate Di-isopropylazodicarboxylate (1. 3 mL, 6. 6 mmol) was added dropwise to a solution of 2-nitroimidazole (1. g, 9 mmol), N-trityl-L-serine methyl ester (2.0 g, 6 mmol) and triphenylphosphine (1. 73g, 6. 6 mmol) in THF (100 mL). The reaction was stirred at ambient temperature for approximately 5 hours The volatiles were removed by evaporation under reduced pressure and the residue purified by column chromatography (EtOAc : isohexane 1 : 19) to afford the title compound (1. 2 g, 44percent) as a white solid. H NMR 3. 08 (s, 3H), 3. 16 (d, 1H), 3. 69 (m, 1H), 4. 46 (dd, 1H), 4. 62 (dd, 1H), 7. 15 (m, 15H), 7.33 (s, 1H), 7.93 (s, 1H); MS m/z (M+NH4)+ 479.

Reference： [1]Patent: WO2003/74532,2003,A1 .Location in patent: Page/Page column 107-108

12
[ 527-73-1 ]
[ 7778-01-0 ]
[ 912343-04-5 ]

Yield	Reaction Conditions	Operation in experiment
91%	With sodium carbonate; In dimethyl sulfoxide; at 60℃; for 6h;	To a solution of 2-nitroimidazole and 1-bromomethy 1-3, 5 -dichloro-benzene in anhydrous DMSO was added Na2CO3. The reaction mixture was heated to 60 0C for 6 h. The reaction mixture was then diluted with EtOAc and washed with water (x4). The organic phase was dried over Na2SO4 and concentrated. The resulting residue was purified by silica gel prep TLC using 98:2 CH2Cl2MeOH to afford l-(3,5-dichloro-benzyl)-2-nitro- lH-imidazole (0.66g, 91%).

Reference： [1]Patent: WO2006/107923,2006,A1 .Location in patent: Page/Page column 71

13
[ 2508-01-2 ]
[ 527-73-1 ]
[ 584-08-7 ]
[ 131504-99-9 ]

Yield	Reaction Conditions	Operation in experiment
3.5 g (35%)	In N,N-dimethyl-formamide	5 3-[2-(2-Nitro-1H-imidazol-1-yl)ethyl]-2-oxazolidinone EXAMPLE 5 3-[2-(2-Nitro-1H-imidazol-1-yl)ethyl]-2-oxazolidinone A mixture of 5 g (44 mmol) of 2-nitroimidazole and 6.1 g of K2 CO3 in 50 ml of DMF was heated at 60° C. for 0.5 hours; then 6.61 g (44 mmol) of 3-(2-chloroethyl)-2-oxazolidinone was added and stirring continued for 18 hours; at 60° C. The mixture was then cooled and concentrated. The residue was partitioned between CHCl3 and water, the organic layer was dried and concentrated to a solid. The solid was crystallized from ethanol to give 3.5 g (35%) of the desired product, 3-[2-(2-nitro-1H-imidazol-1-yl)ethyl]-2-oxazolidinone; mp 103°-104° C.

Reference： [1]Current Patent Assignee: PFIZER INC - US4954515, 1990, A

14
[ 527-73-1 ]
[ 86357-13-3 ]
[ 123066-80-8 ]

Yield	Reaction Conditions	Operation in experiment
88.6%	With p-toluenesulfonic acid monohydrate; In ethyl acetate;	EXAMPLE 1 1-[2-acetoxy-1-(acetoxymethyl)ethoxy]methyl-2-nitroimidazol: compound (1) 5.6 g of 2-nitroimidazol, 12.4 g of 1,3-diacetoxy-2-acetoxymethoxypropane and 0.5 g of p-toluenesulfonic acid monohydrate were placed in a flask connected with a trap for reducing pressure by an aspirator. The flask was heated by oil bath of 130-140 C. under reduced pressure while stirred. Acetic acid was distilled out as the reaction proceeded. In about 15 minutes, the reaction was completed. After cooling down to room temperature, the content was added with about 300 ml ethyl acetate and subjected to extraction. The extract was washed with saturated aqueous sodium hydrogen carbonate, and with water in this order. Then it was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by separable high performance liquid chromatography through silica gel columns using a mixture solvent (ethyl acetate - benzene) as an elude to obtain 13.3 g of the title compound as a viscous oil material (yield: 88.6%). MS(m/e): 301(M+), IR(cm-1): 1740 (CO), 1535 (NO2), 1490 (NO2), NMR(delta, CDCl3): 2.0 (s, 6H, CH3 CO*2),

Reference： [1]Patent: US4945102,1990,A

15
[ 4945-53-3 ]
[ 527-73-1 ]
[ CAS Unavailable ]
[ 70132-50-2 ]

Yield	Reaction Conditions	Operation in experiment
11%	With sodium carbonate; potassium carbonate In ethanol; water; ethyl acetate	17.a EXAMPLE 17 (a) A mixture of 5.65 g (50 mmol) of 2-nitroimidazole and 250 mg of anhydrous potassium carbonate in 150 ml of ethanol was heated under reflux for 15 minutes. 7.05 g (50 mmol) of freshly distilled 3-piperidino-propylene oxide in a minimum amount of ethanol were added to the mixture and heating under reflux was continued for 3 hours. The mixture was filtered and the filtrate was evaporated to dryness in vacuo to give ca. 13 g of a yellow oil which was partitioned between 100 ml of ethyl acetate and 100 ml of water. The aqueous layer was separated and washed once with 50 ml of ethyl acetate. The combined organic phases were extracted with four 50 ml portions of 2-N hydrochloric acid. The combined aqueous-acidic solutions were made basic by the addition of excess solid sodium carbonate and extracted with three 100 ml portions of dichloromethane. The combined organic phases were dried over anhydrous sodium carbonate and filtered. The filtrate was evaporated to dryness in vacuo to give 6.5 g of a pale yellow solid which was redissolved in 25 ml of hot ethanol, treated with decolorizing charcoal, filtered and left to crystallize, there being obtained 1.4 g (11% yield) of 2-nitro-α-(piperidino)methyl-1-imidazole-ethanol in the form of a pale yellow crystalline solid of melting point 108°-109° C.

Reference： [1]Current Patent Assignee: ROCHE HOLDING AG - US4241060, 1980, A

16
[ 527-73-1 ]
(2R,3R)-2-bromomethoxy-1,3,4-triacetoxybutane [ No CAS ]
[ 161903-13-5 ]
[ 636-70-4 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In N-methyl-acetamide;	Example 6 Synthesis of (1'R,2'R)-1-[(1'-acetoxymethyl-2', 3'-diacetoxy)propoxy]methyl-2-nitroimidazole 21.5 g of 2-nitroimidazole, 20.0 g of triethylamine, and 50 ml of dimethylformamide were added to all the amount of the crude (2R,3R)-2-bromomethoxy-1,3,4-triacetoxybutane obtained in Example 5. The reaction was exothermic, producing white precipitate of triethylamine hydrobromide.

Reference： [1]Patent: US5532380,1996,A

17
[ 527-73-1 ]
zinc nitrate tetrahydrate [ No CAS ]
[ 68-12-2 ]
[ 57090-88-7 ]
[ 1136998-75-8 ]

Reference： [1]Journal of the American Chemical Society,2009,vol. 131,p. 3875 - 3877

18
[ 527-73-1 ]
[ 123237-62-7 ]
[ 1162674-93-2 ]

Yield	Reaction Conditions	Operation in experiment
70%	With potassium carbonate In ethanol at 85℃; for 5h;
49%	With potassium carbonate In ethanol at 78℃; for 3h;

Reference： [1]Kim, Pilho; Zhang, Liang; Manjunatha, Ujjini H.; Singh, Ramandeep; Patel, Sejal; Jiricek, Jan; Keller, Thomas H.; Boshoff, Helena I.; Barry III, Clifton E.; Dowd, Cynthia S. [Journal of Medicinal Chemistry, 2009, vol. 52, # 5, p. 1317 - 1328]
[2]Patterson, Stephen; Wyllie, Susan; Stojanovski, Laste; Perry, Meghan R.; Simeons, Frederick R. C.; Norval, Suzanne; Osuna-Cabello, Maria; De Rycker, Manu; Read, Kevin D.; Fairlamb, Alan H. [Antimicrobial Agents and Chemotherapy, 2013, vol. 57, # 10, p. 4699 - 4706]

19
[ 527-73-1 ]
[ 31984-10-8 ]
[ 1092852-30-6 ]

Reference： [1]Chemical Biology and Drug Design,2010,vol. 75,p. 68 - 90

20
[ 527-73-1 ]
[ 124150-87-4 ]
(R)-1-((tert-butyldimethylsilyl)oxy)-3-(2-nitro-1H-imidazol-1-yl)propan-2-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
32%	With potassium carbonate In ethanol at 78℃; for 2h;

Reference： [1]Patterson, Stephen; Wyllie, Susan; Stojanovski, Laste; Perry, Meghan R.; Simeons, Frederick R. C.; Norval, Suzanne; Osuna-Cabello, Maria; De Rycker, Manu; Read, Kevin D.; Fairlamb, Alan H. [Antimicrobial Agents and Chemotherapy, 2013, vol. 57, # 10, p. 4699 - 4706]

21
[ 527-73-1 ]
[ 142356-33-0 ]
[ 1522098-19-6 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In N,N-dimethyl-formamide; at 20℃;	[0050] NI was converted to 6-(2-nitroimidazole)hexylamine for chemical reaction with the carboxylic acids of CM-Dex. In brief, NI (0.6 g, 5.3 mmol) was dissolved in DMF, to which K2CO3 (1.1 g, 7.95 mmol) was added. 6-(Boc-amino)hexyl bromide (1.56 g, 5.57 mmol) in DMF was then added dropwise and stirred at room temperature (RT) overnight. The reaction mixture was filtered and washed with methanol, after which the residual solvent was evaporated. The solid obtained was suspended in water and extracted with ethyl acetate. The organic layer was separated, dried over sodium sulfate, and concentrated to obtain the product for step 1.
	With potassium carbonate; In N,N-dimethyl-formamide; at 80℃; for 4h;	Synthesis and characterizations of hypoxia-sensitive hyaluronic acid (HS-HA) (0127) Hypoxia-sensitive hyaluronic acid (HS-HA) was synthesized by chemically conjugating 6-(2- nitroimidazole) hexylamine through amide formation. First, 6-(2-nitroimidazole) hexylamine was synthesized to react with the carboxylic acids groups of HA. In brief, NI (0.15 g, 1.3 mmol) was dissolved in DMF, to which K2CO3 (0.28 g, 2.0 mmol) was added. Then 6-(Boc-amino) hexyl bromide (0.39 g, 1.4 mmol) was added dropwise into the solution and stirred at 80 C for 4 hours. The solid impurities were separated from the reaction mixture through filtration and washed with methanol. The solid product was obtained from the residual solvent by evaporation, which was suspended in deionized (DI) water and then extracted with ethyl acetate. The organic layer was collected and concentrated with sodium sulfate. The product was re-dissolved in methanol on the ice. 5 mL of 1.25 M HCl in methanol was added to the solution and stirred for (0128) 24 h at room temperature (RT). Afterward, the solvent was removed using rotary evaporator to obtain the amine-functionalized NI. Second, 6-(2-nitroimidazole) hexylamine was conjugated to (0129) HA in the presence of l-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDC) and N- hydroxysuccinimide (NHS). Briefly, 0.24 g of HA (molecular weight: ~300kDa) was dissolved in water, to which EDC (0.56 g, 3.4 mmol) and NHS (0.39 g, 3.4 mmol) were added and stirred for 15 minutes at room temperature. Later 6-(2-nitroimidazole) hexylamine (0.18 g, 0.85 mmol) in DMF was added to the mixture and reacted at room temperature for 24 hours. The dialysis was performed thoroughly against a 1 : 1 mixture of DI water and methanol for 24h and DI water for 48 hours. Then, HS-HA was obtained by lyophilization and characterized by NMR (Varian Gemini 2300). The graft degree is determined as 20% by UV-Vis absorbance. (0130) 6-(2-nitroimidazole) hexylamine: NMR (DMSO-d6, 300 MHz, delta ppm): 1.30-1.78 (m, 8H, NH2CH2(CH2)4), 2.73 (s, 2H, NH2CH2), 4.38 (s, 2H, NCH2), 7.19 (s, 1H), 7.87 (s, 1H). (0131) HS-HA: NMR (D20, 300 MHz, delta ppm): 1.88-2.40 (m, 8H, NH2CH2(CH2)4), 2.87-3.19 (m, 4H, NH2CH2, NC%), 7.19 (s, 1H), 7.48 (s, 1H).

Reference： [1]Patent: US2014/141084,2014,A1 .Location in patent: Paragraph 0016; 0049; 0050
[2]Patent: WO2017/143153,2017,A1 .Location in patent: Page/Page column 21; 22
[3]Journal of Materials Chemistry B,2019,vol. 7,p. 286 - 295

22
[ 527-73-1 ]
[ 7720-39-0 ]

Yield	Reaction Conditions	Operation in experiment
	With palladium on activated charcoal; acetic acid; In tert-butyl alcohol;	Scheme 6-2: In Step 1 the appropriately substituted nitro species is reduced with palladium as known in the art to afford an amine. In Step 2 the appropriately substituted alkene species is brominated with concurrent oxidation with ethanol as known in the art to afford the bromide species. In Step 3 the appropriately substituted aryl species is subjected to the previously prepared bromide species as known in the art to afford a bicycle precursor. In Step 4 the appropriately substituted ketal species is deprotected and subsequently cyclized in the presence of acid as known in the art. In Step 5 the appropriately substituted cyano species is subjected to strong acid to afford a primary amide. In Step 6 the appropriately substituted heterocycle is subjected to a bromide species of the appropriate linker to afford the appropriately protected species. Various 5-5 fused bicyclic systems can be appropriately prepared by slight modifications of this synthetic protocol, another non-limiting example is presented in Steps 5 through 12 with the same conditions for formation of a primary amide and installation of linker. In Step 7 the appropriately substituted aryl species is brominated as known in the art. In Step 8 the appropriately substituted ether species is deprotected with palladium as known in the art to afford an alcohol. In Step 9 the appropriately substituted alcohol is oxidized as known in the art to afford an aldehyde. In Step 10 the appropriately substituted aldehyde is subjected to hydrazine to first form a Schiff base and subsequently cyclize to afford a bicyclic system. In Step 11 the appropriately substituted bicyclic system is iodinated as known in the art. In Step 12 the appropriately substituted iodide is subjected to sodium cyanide to afford a cyano species.

Reference： [1]RSC Advances,2014,vol. 4,p. 22567 - 22574
[2]Patent: WO2018/160891,2018,A1 .Location in patent: Page/Page column 497-498

23
[ 527-73-1 ]
[ 175711-83-8 ]
[ 1616406-12-2 ]

Reference： [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 5702 - 5713

24
[ 527-73-1 ]
cobalt nitrate [ No CAS ]
[ 4887-82-5 ]
[ 1082741-89-6 ]

Reference： [1]CrystEngComm,2014,vol. 16,p. 4677 - 4680

25
[ 527-73-1 ]
cobalt nitrate [ No CAS ]
[ 4887-88-1 ]
C₇H₄BrN₂^(1-)*C₃H₂N₃O₂^(1-)*Co⁽²⁺⁾ [ No CAS ]

Reference： [1]CrystEngComm,2014,vol. 16,p. 4677 - 4680

26
[ 110-52-1 ]
[ 527-73-1 ]
1-(4-bromobutyl)-2-nitro-1H-imidazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86%	With potassium carbonate In N,N-dimethyl-formamide at 60℃; for 4h;	4.1.2. General synthetic procedure of nitroimidazole derivatives (9a-9e, 11a-11c) General procedure: Dibromo-alkane (0.04 mol) was added to a stirred mixture of nitroimidazole derivative (8 or 10, 0.01 mol) and potassium carbonate (1.38 g, 0.02 mol) in DMF (5 mL). The mixture was heated to 60 °C and stirred for about 4 h. After cooling to room temperature, the mixture was filtered and the filtrate was concentrated to dryness. The residue was purified by silica gel column chromatography to get pure 9a-9e and 11a-11c.
86%	With potassium carbonate In N,N-dimethyl-formamide at 60℃; for 4h;	2 4.1.2. General synthetic procedure of nitroimidazole derivatives (9a-9e) General procedure: To a stirred solution of 2-nitroimidazole (8) (1.13 g, 0.01 mol) and potassium carbonate (1.38 g, 0.02 mol) in DMF (5.0 mL) was added alkyl halide (0.04 mol). The reaction mixture was heated to 60 °C and stirred for about 4 h. After cooling to room temperature,the mixture was filtered and the filtrate was concentrated to dryness. The residue was purified by silica gel column chromatographyto get pure 9a-9e. 4.1.2.2 1-(4-Bromobutyl)-2-nitro-1H-imidazole (9b) Yellow oil, yield: 86%. 1H NMR (500 MHz, CDCl3) δ 7.15 (s, 1H), 7.11 (s, 1H), 4.46 (t, J = 7.5 Hz, 2H), 3.42 (t, J = 6.5 Hz, 2H), 2.08-2.00 (m, 2H), 1.95-1.88 (m, 2H). ESI-MS m/z: 248 [M+H]+.
79%	Stage #1: 2-nitro-1H-imidazole With potassium carbonate In acetonitrile at 70℃; for 0.5h; Stage #2: 1,4-dibromo-butane In acetonitrile

	With potassium carbonate In N,N-dimethyl-formamide
	With tetrabutylammonium bromide; potassium carbonate In acetone at 60℃; for 7h;

Reference： [1]Cheng, Weiyan; Zhu, Shijun; Ma, Xiaodong; Qiu, Ni; Peng, Peng; Sheng, Rong; Hu, Yongzhou [European Journal of Medicinal Chemistry, 2015, vol. 89, p. 826 - 834]
[2]Cheng, Weiyan; Yuan, Youting; Qiu, Ni; Peng, Peng; Sheng, Rong; Hu, Yongzhou [Bioorganic and Medicinal Chemistry, 2014, vol. 22, # 24, p. 6796 - 6805]
[3]Saini, Nisha; Varshney, Raunak; Tiwari, Anjani K.; Kaul, Ankur; Ishar; Mishra, Anil K. [RSC Advances, 2015, vol. 5, # 118, p. 97102 - 97112]
[4]Nunes, Paulo Sérgio Gonçalves; Zhang, Zhengxing; Kuo, Hsiou-Ting; Zhang, Chengcheng; Rousseau, Julie; Rousseau, Etienne; Lau, Joseph; Kwon, Daniel; Carvalho, Ivone; Bénard, François; Lin, Kuo-Shyan [Journal of labelled compounds and radiopharmaceuticals, 2018, vol. 61, # 4, p. 370 - 379]
[5]Li, Na; Xu, Manyi; Zhang, Lulu; Lei, Zhichao; Chen, Cheng; Zhang, Tianyuan; Chen, Li; Sun, Jianbo [Journal of Medicinal Chemistry, 2022, vol. 65, # 6, p. 4578 - 4589]

27
[ 527-73-1 ]
[ 111-24-0 ]
1-(5-bromopentyl)-2-nitro-1H-imidazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
82%	With potassium carbonate In N,N-dimethyl-formamide at 60℃; for 4h;	4.1.2. General synthetic procedure of nitroimidazole derivatives (9a-9e, 11a-11c) General procedure: Dibromo-alkane (0.04 mol) was added to a stirred mixture of nitroimidazole derivative (8 or 10, 0.01 mol) and potassium carbonate (1.38 g, 0.02 mol) in DMF (5 mL). The mixture was heated to 60 °C and stirred for about 4 h. After cooling to room temperature, the mixture was filtered and the filtrate was concentrated to dryness. The residue was purified by silica gel column chromatography to get pure 9a-9e and 11a-11c.
82%	With potassium carbonate In N,N-dimethyl-formamide at 60℃; for 4h;	3 4.1.2. General synthetic procedure of nitroimidazole derivatives (9a-9e) General procedure: To a stirred solution of 2-nitroimidazole (8) (1.13 g, 0.01 mol) and potassium carbonate (1.38 g, 0.02 mol) in DMF (5.0 mL) was added alkyl halide (0.04 mol). The reaction mixture was heated to 60 °C and stirred for about 4 h. After cooling to room temperature,the mixture was filtered and the filtrate was concentrated to dryness. The residue was purified by silica gel column chromatographyto get pure 9a-9e. 4.1.2.3 1-(5-Bromopentyl)-2-nitro-1H-imidazole (9c) Yellow oil, yield: 82%. 1H NMR (500 MHz, CDCl3) δ 7.14 (s, 1H), 7.10 (s, 1H), 4.42 (t, J = 7.5 Hz, 2H), 3.40 (t, J = 6.5 Hz, 2H), 1.93-1.84 (m, 4H), 1.55-1.49 (m, 2H). ESI-MS m/z: 262 [M+H]+.
	With tetrabutylammonium bromide; potassium carbonate In acetone at 60℃; for 7h;

28
[ 527-73-1 ]
[ 86536-92-7 ]
[ 1522098-19-6 ]

Yield	Reaction Conditions	Operation in experiment
47%	With caesium carbonate In N,N-dimethyl-formamide at 65℃; for 2h;	S3 Synthesis of tert-butyl 6-(2-nitroimidazole)hexylcarbamate Take 1.64 g (4.42 mmol) tert-butyl 6-toluenesulfonylhexylcarbamate, 0.5 g (4.42 mmol) 2-nitroimidazole, and 1.44 g (4.42 mmol) Cs2CO3, add with 20 mL anhydrous DMF. Heat the mixture to 65° C. and stir the mixture for 2 hours. Then vacuum heat to 50° C. for evaporation and add chloroform for dissolution. Take the dissolved part and concentrate the dissolved part by vacuum concentration. Use liquid chromatography (EA:CHC13=1:4) for isolation and purification of the product tert-butyl 6-(2-nitroimidazole)-hexylcarbamate (0.68 g, 47%).

Reference： [1]Current Patent Assignee: ATOMIC ENERGY COUNCIL - US2014/371434, 2014, A1 Location in patent: Paragraph 0028; 0031; 0055

29
[ 527-73-1 ]
[ 74-88-4 ]
[ 1671-82-5 ]

Yield	Reaction Conditions	Operation in experiment
100%	With caesium carbonate; In N,N-dimethyl-formamide; at 50℃;Inert atmosphere;	To a stirred solution of 2-nitro-lH- imidazole (500 mg, 4.42 mmol) in DMF (6 mL) was added CS2CO3 (4.3 g, 13.3 mmol) before introduction of Mel (942 mg, 6.63 mmol). The resulting mixture was heated to 50C under N2 overnight. The reaction was quenched with aqueous NaHCC>3 (sat.) and extracted with EA (25 mL x 3). The combined organic layers was dried over Na2S04, filtered and concentrated. The crude product was purified by flash chromatography (silica gel, 0-50% ethyl acetate in petroleum ether) to provide l-methyl-2-nitro-lH-imidazole (542-1) (530 mg, 100 %) as a yellow solid. LC-MS (ESI): m/z (M+) 128.1
0.14 g		To a stirred solution of 238.1 (0.2 g, 1.76 mmol) in DMF (10 mL) was added 60% NaH (0.14 g, 3.54 mmol) portion wise at 0 C. After stirring for 1 h, Mel (0.25 g, 1.77 mmol) was added at 0 C. After stirring at RT for 16 h, the reaction mixture was quenched with ice cold water and extracted with EtOAc (3x50mL). The combined organic layer was washed with brine and dried over anhydrous Na2SC>4 and concentrated to obtain 238.2 (0.14 g) as a gummy material. NMR (500 MHz, CDCb): 7.14 (d , J = 1.0 Hz, 1H), 7.06 (s, 1H), 4.08 (s, 3H); LCMS: (0649) 57.04%, m/z [M+H]+ = 127.9.

Reference： [1]Patent: WO2016/4272,2016,A1 .Location in patent: Paragraph 00798
[2]Patent: WO2020/160010,2020,A1 .Location in patent: Page/Page column 160

30
[ 527-73-1 ]
zinc(II) nitrate hexahydrate [ No CAS ]
[ 1414662-67-1 ]
[ 7732-18-5 ]
[ 33513-42-7 ]
[Zn₂(NH₂-BTB)][2-nim]*DMF*6H₂O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With tetraethylammonium bromide at 100℃; for 24h; Sealed tube;

Reference： [1]Ding, Qing-Rong; Wang, Fei [Dalton Transactions, 2016, vol. 45, # 16, p. 7004 - 7007]

31
[ 527-73-1 ]
[ 83948-54-3 ]
tert-butyl (5-(2-nitro-1H-imidazol-1-yl)pentyl)carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
81%	With potassium carbonate; In N,N-dimethyl-formamide; at 80℃; for 0.333333h;Microwave irradiation;	tert-butyl (6-(2-nitro-1H-imidazol-1 -yl)pentyl)carbamate 1. To a solution of 2-nitroimidazole (51 mg, 0.45 mmol) and tert-butyl (5-bromopentyl)carbainate (100 mg, 0.38 mmol) in DMF (3.5 mE) was added potassium carbonate (79 mg, 0.57 mmol). The reaction mixture was heated at 80 C. for 20 mm under microwave then cooled to room temperature, filtered through a Celite pad and the filtrate concentrated in vacuo. The residue was purified by column chromatography using Hex/EtOAc (gradient: 0 to 50% EtOAc) to afford tert-butyl (5-(2-nitro-1 H-imidazol- 1 -yl)pentyl)carbamate 1 (92 mg, 81%) as an oil. ?H NMR (CDC13, 400 MHz) oe (ppm) 7.14 (s, 1H), 7.08 (s, 1H), 4.41 (t, J=7.2 Hz, 2H), 3.14-3.10 (m, 2H), 1.88 (qt, J=7.6 Hz, 2H), 1.60-1.48 (m,2H), 1.44 (s, 9H), 1.40-1.3 1 (m,2H); ECMS (ES1) tR: 0.906 mm (>99%, EESD), mlz:299.3 [M+1]+

Reference： [1]Patent: US2016/151517,2016,A1 .Location in patent: Paragraph 0069; 0070

32
[ 527-73-1 ]
[ 106268-96-6 ]
C₁₄H₁₄N₄O₇ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
72%	With N-ethyl-N,N-diisopropylamine In ethyl acetate; acetonitrile at 77℃; for 44h;

Reference： [1]Current Patent Assignee: UNIVERSITY OF DUNDEE - WO2017/72523, 2017, A1 Location in patent: Page/Page column 21

33
[ 288-32-4 ]
[ 527-73-1 ]
zinc nitrate tetrahydrate [ No CAS ]
[ 4887-82-5 ]
[zinc(II)(5-chlorobenzimidazole)_0.7(2-nitroimidazole)_0.3(imidazole)] [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2017,vol. 139,p. 6448 - 6455

34
[ 288-32-4 ]
[ 527-73-1 ]
zinc nitrate tetrahydrate [ No CAS ]
[ 4887-82-5 ]
[zinc(II)(5-chlorobenzimidazole)_0.95(2-nitroimidazole)_0.6(imidazole)_0.45] [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2017,vol. 139,p. 6448 - 6455

35
[ 288-32-4 ]
[ 527-73-1 ]
zinc nitrate tetrahydrate [ No CAS ]
[ 614-97-1 ]
[zinc(II)(5-methylbenzimidazole)_1.03(2-nitroimidazole)_0.64(imidazole)_0.33] [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2017,vol. 139,p. 6448 - 6455

36
[ 527-73-1 ]
[ 627-18-9 ]
3-(2-nitro-1H-imidazol-1-yl)propan-1-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88%	With caesium carbonate In N,N-dimethyl-formamide at 60℃; for 12h;
88%	Stage #1: 2-nitro-1H-imidazole With caesium carbonate In N,N-dimethyl-formamide at 20℃; for 0.0833333h; Stage #2: 1-bromo-3-propanol In N,N-dimethyl-formamide at 50℃; for 12h;	1 Example 1 Preparation of compound 3 Cesium carbonate (5.8 g, 17.70 mmol)Was added to compound 1 (1 g, 8.85 mmol)N, N-dimethylformamide, stirred at room temperature for 5 minutes,Compound 2 (1.4 g, 9.73 mmol) was added to the system,The reaction mixture was reacted at 50 ° C for 12 hours, the reaction vessel was steamed and concentrated,The concentrate was purified by column chromatography (dichloromethane: methanol = 60: 1) to give a pale yellow solid (1.3 g, 88%).
	With potassium carbonate; potassium iodide In acetone for 12h;	1.1.4. General procedure for synthesis of hybrids12a-n General procedure: The corresponding imidazole (2 mmol) and 2-bromoethanol or 3-bromo-1-propanol or 4-bromo-1-butanol (2.4 mmol) dissolved in acetone (20 ml). Then K2CO3(6 mmol) and KI (2 mmol) were added. The reaction mixture was stirred at 60oCfor 12h. Filtered, the filtrate was concentrated under reduced pressure and dried under vacuum. The1H-NMR and13C-NMR were consistent with the literature.

Reference： [1]Jin, Chen; Wen, Shuai; Zhang, Qiumeng; Zhu, Qiwen; Yu, Jiahui; Lu, Wei [ACS Medicinal Chemistry Letters, 2017, vol. 8, # 7, p. 762 - 765]
[2]Current Patent Assignee: EAST CHINA NORMAL UNIVERSITY - CN106977501, 2017, A Location in patent: Paragraph 0044; 0045; 0046; 0047
[3]Hu, Yanping; Li, Na; Zhang, Jiayao; Wang, Ying; Chen, Li; Sun, Jianbo [Bioorganic and Medicinal Chemistry Letters, 2019, vol. 29, # 9, p. 1138 - 1142]

37
[ 527-73-1 ]
[ 54512-75-3 ]
1-(5-chloropentyl)-2-nitro-1H-imidazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	With caesium carbonate; In N,N-dimethyl-formamide; at 18℃; for 16h;	As shown in Figure 2B, 1 -Bromo-5-chloropentane (25 ml_, 35 mmol) was added to a stirred solution of 2-nitroimidazole (1) (200 mg, 1.75 mmol) in anhydrous DMF (30 ml_), and then caesium carbonate (1.14 g, 3.5 mmol) was added. The reaction was stirred at 18C for 16 h. The reaction mixture was partitioned between ethyl acetate (200 mL) and H20 (50 ml_) three times. The organic phase was washed with H20 and brine three times, followed by solvent evaporation. The crude product was purified by column chromatography, eluting with petroleum ether first, to extract the l-bromo-5-chloropentane, and then eluting with ethyl acetate, to give 1-(5-chloropentyl)-2-nitro-1H-imidazole (11) (75%) as an oil. 1H NMR (300

Reference： [1]Patent: WO2018/85809,2018,A1 .Location in patent: Page/Page column 40

38
[ 527-73-1 ]
[ 1273-86-5 ]
C₁₄H₁₃FeN₃O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
83%	With acetic acid at 60℃; for 9h;	1.1. Synthesis of 1-ferrocenylmethyl(2-methylimidazole) FcImCH₃ General procedure: The general procedure described by Pan et.al. ADDIN EN.CITE He201353[46]535317He, PanDu, YufengWang, ShuzhanCao, ChangshengWang, XiaojunPang, GuangshengShi, YanhuiSynthesis, Structure, and Reactivity of Ferrocenyl-NHC Palladium ComplexesZeitschrift für anorganische und allgemeine ChemieZeitschrift für anorganische und allgemeine Chemie1004-1010639620131521-3749[1] was used to synthesize ferrocenyl(2-methyl imidazole). Briefly, ferrocenemethanol (1 mM) and 2-methyl-1H-imidazole (1.1 mM) were refluxed in acetic acid for 9 hrs at 60 °C. The reaction was monitored on preparative TLC. The product was neutralized with 50% KOH in distilled water to remove the acetic acid. The residue was chromatographed on a packed column with CH2Cl2/MeOH (4:1) eluent.

Reference： [1]Labulo, Ayomide H.; Ngidi, Nonjabulo P.D.; Omondi, Bernard; Nyamori, Vincent O. [Journal of Organometallic Chemistry, 2018, vol. 868, p. 66 - 75]

39
[ 527-73-1 ]
[ 4637-24-5 ]
[ 1671-82-5 ]

Yield	Reaction Conditions	Operation in experiment
93.5%	In N,N-dimethyl-formamide; at 80℃; for 2h;	To 2-nitro-(1H)-imidazole (2.0 g, 17.7 mmol)N,N-dimethylformamide dimethyl acetal (8.4 g, 70.7 mmol) was added dropwise to a solution of DMF (10 ml).The reaction was carried out at 80 C for 2 h. Add water (30ml) and ethyl acetate (25ml),The mixture was extracted with ethyl acetate (25×2 mL).Dry over anhydrous sodium sulfate, filter, and concentrate the filtrate under reduced pressure.The crude product was separated by column chromatography (eluent: dichloromethane: anhydrous methanol = 30:1).A pale yellow solid (2.1 g, 93.5%) was obtained.The product purity is 99.7% (mass fraction)

Reference： [1]Patent: CN108503583,2018,A .Location in patent: Paragraph 0051-0053; 0059; 0060

40
[ 527-73-1 ]
[ 87066-94-2 ]
C₁₅H₁₈N₄O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
661 mg	With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; toluene; at 20.0℃; for 14.5h;Cooling with ice;	(3) To a suspension of the Compound 4 (569 mg), the Compound 5 (339 mg), and triphenylphosphine (944 mg) in tetrahydroffiran (12 mE) was added diethyl azodicarboxylate (40 wt % solution in toluene, 1.65 mE) under ice- cooling, and the resulting mixture was stirred at room temperature for 14.5 hours. The reaction mixture was concentrated under reduced pressure, and then the resulting residues were purified by silica gel column chromatography (hexane:ethyl acetate=95:5 to 70:30) to give the Compound 6 (661 mg) as a yellow viscous material. MS (APCI): mlz287 [M+H]
661 mg	With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; toluene; at 20.0℃; for 14.5h;Cooling with ice;	(3) Compound 4 (569 mg), Compound 5 (339 mg),Triphenylphosphine (944 mg) inTetrahydrofuran (12 mL)To the suspension under ice coolingDiethyl azodicarboxylate(40 wt% toluene solution,1.65 mL) was added,And the mixture was stirred at room temperature for 14.5 hours.The reaction mixture was concentrated under reduced pressure, The residue was purified by silica gel column chromatography (hexane: ethyl acetate = 95: 5 to 70:30)Compound 6 (661 mg) was obtained as a yellow viscous substance.

Reference： [1]Patent: US2018/258076,2018,A1 .Location in patent: Paragraph 0496
[2]Patent: JP2018/199673,2018,A .Location in patent: Paragraph 0170

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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. 527-73-1 ] {[proInfo.proName]}

Quality Control of [ 527-73-1 ]

Related Doc. of [ 527-73-1 ]

Product Details of [ 527-73-1 ]

Calculated chemistry of [ 527-73-1 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 527-73-1 ]

Application In Synthesis of [ 527-73-1 ]

[ 527-73-1 ] Synthesis Path-Upstream 1~8

[ 527-73-1 ] Synthesis Path-Downstream 1~40

Related Functional Groups of [ 527-73-1 ]

Nitroes

Related Parent Nucleus of [ 527-73-1 ]

Imidazoles

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 527-73-1 ]

Related Parent Nucleus of
[ 527-73-1 ]