87802-11-7 (5-氯吲哚-2-羧酸甲酯,Methyl 5-chloro-1H-indole-2-carboxylate)

快速询单

结构式：

5-氯吲哚-2-羧酸甲酯MOL文件

CAS号：

87802-11-7

中文名称：

5-氯吲哚-2-羧酸甲酯

英文名称：

Methyl 5-chloro-1H-indole-2-carboxylate

分子式：

C₁₀H₈ClNO₂

分子量：

209.629021644592

5-氯吲哚-2-羧酸甲酯(87802-11-7)名称与标识符

名称

中文别名：

5-氯-1H-吲哚-2-羧酸甲酯;5-氯吲哚-2-羧酸甲酯;

英文别名：

Methyl 5-chloro-1H-indole-2-carboxylate;1H-INDOLE-2-CARBOXYLIC ACID,5-CHLORO-,METHYL ESTER;5-CHLOROINDOLE-2-CARBOXYLIC ACID METHYL ESTER;5-CHLORO-1H-INDOLE-2-CARBOXYLIC ACID METHYL ESTER;METHYL 5-CHLOROINDOLE-2-CARBOXYLATE;DB-058151;CS-0150776;AKOS004116680;RS-0322;DTXSID40406441;C-4625;MFCD04972050;MB03385;SCHEMBL3963537;87802-11-7;

标识符

MDL：

MFCD04972050

InChIKey：

WGAOEHZSJWVLBY-UHFFFAOYSA-N

Inchi：

1S/C10H8ClNO2/c1-14-10(13)9-5-6-4-7(11)2-3-8(6)12-9/h2-5,12H,1H3

SMILES：

O=C(C1NC2C(=CC(=CC=2)Cl)C=1)OC

5-氯吲哚-2-羧酸甲酯(87802-11-7)物化性质

实验特性

LogP : 2.60790
PSA : 42.09000
折射率 : 1.647
沸点 : 365.5±22.0 °C at 760 mmHg
蒸气压 : 0.0±0.8 mmHg at 25°C
闪点 : 174.8±22.3 °C
密度 : 1.4±0.1 g/cm3

计算特性

精确分子量 : 209.02400
氢键供体数量 : 1
氢键受体数量 : 3
可旋转化学键数量 : 2
同位素质量 : 209.0243562g/mol
重原子数量 : 14
复杂度 : 234
同位素原子数量 : 0
确定原子立构中心数量 : 0
不确定原子立构中心数量 : 0
确定化学键立构中心数量 : 0
不确定化学键立构中心数量 : 0
共价键单元数量 : 1
疏水参数计算参考值（XlogP） : 3.1
拓扑分子极性表面积 : 42.1Å²

5-氯吲哚-2-羧酸甲酯(87802-11-7)安全信息

安全说明： H303+H313+H333
危害声明：H303+H313+H333
警示性声明：P264+P280+P305+P351+P338+P337+P313
储存条件： storage at -4℃ (1-2weeks), longer storage period at -20℃ (1-2years)
信号词： warning

5-氯吲哚-2-羧酸甲酯(87802-11-7)海关数据

海关编码：

2933990090

海关数据：

中国海关编码：

2933990090

概述：

2933990090. 其他仅含氮杂原子的杂环化合物. 增值税率:17.0%. 退税率:13.0%. 监管条件:无. 最惠国关税:6.5%. 普通关税:20.0%

申报要素：

品名, 成分含量, 用途, 乌洛托品请注明外观, 6－己内酰胺请注明外观, 签约日期

Summary：

2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

5-氯吲哚-2-羧酸甲酯(87802-11-7)推荐厂家更多厂家(15)

公司名称	手机号/电话	联系人	QQ	询单
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上海绩祥生物科技有限公司	13093077543	陆经理	3985448220	询单
南通众合化工新材料有限公司	18762756250 0513-55074056	胡经理	2369399482	询单
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上海腾准生物科技有限公司	19821570922 021-34053661	张经理	3003871136	询单
金锦乐（湖南）化学有限公司		金锦乐	1226360695	询单
江苏艾康生物医药研发有限公司	18795912720 025-66061636	杨情情	3004779232	询单
上海吉至生化科技有限公司	18117592386 021-57481218	吉至试剂	3007522982	询单
上海吉至生化科技有限公司	18117592386 021-57481218	吉至试剂	3007522982	询单

5-氯吲哚-2-羧酸甲酯(87802-11-7)合成路线

合成路线：1 步

10517-21-2

67-56-1

_100%

87802-11-7

反应条件：

1.1 Reagents: Sulfuric acid

参考文献：

Study of 5-endro-trig radical cyclisations, application towards new syntheis of Lycorine, synthesis of new DNA intercalating-alkylating agents, analogues to Duocarmycins

Dauge, Delfine, 2005, , ,

合成路线：1 步

10517-21-2

67-56-1

_96%

87802-11-7

反应条件：

1.1 Reagents: Thionyl chloride Solvents: Methanol ; cooled; 4 h, 70 °C

参考文献：

Synthesis and biological evaluation of novel phenylpropenoyl-amino acid derivatives

Gao, Sufan; et al, Youji Huaxue, 2019, 39(7), 1953-1961

合成路线：1 步

1253935-23-7

_90%

87802-11-7

反应条件：

1.1 Catalysts: 5,10,15,20-Tetrakis(pentafluorophenyl)porphyrinatoiron(III) chloride Solvents: 1,2-Dichloroethane ; rt → reflux; 24 h, reflux

参考文献：

[Fe(F20TPP)Cl] catalyzed intramolecular C-N bond formation for alkaloid synthesis using aryl azides as nitrogen source

Liu, Yungen; et al, Chemical Communications (Cambridge, 2010, 46(37), 6926-6928

合成路线：1 步

1426575-08-7

_87%

87802-11-7

反应条件：

1.1 Solvents: Xylene ; 2 h, 140 °C

参考文献：

Extending the versatility of the Hemetsberger-Knittel indole synthesis through microwave and flow chemistry

Ranasinghe, Nadeesha; et al, Bioorganic & Medicinal Chemistry Letters, 2013, 23(6), 1740-1742

合成路线：1 步

380374-20-9

_85%

87802-11-7

反应条件：

1.1 Reagents: Iodobenzene diacetate Catalysts: 5,10,15,20-Tetrakis(pentafluorophenyl)porphyrinatoiron(III) chloride Solvents: Toluene ; 3 h, reflux

参考文献：

[Fe(F20TPP)Cl]-Catalyzed Amination with Arylamines and {[Fe(F20TPP)(NAr)](PhI=NAr)}+. Intermediate Assessed by High-Resolution ESI-MS and DFT Calculations

Liu, Yungen; et al, Chemistry - An Asian Journal, 2015, 10(1), 100-105

合成路线：1 步

956903-52-9

_85%

87802-11-7

反应条件：

1.1 Catalysts: Sulfuric acid Solvents: Methanol ; 2.5 h, reflux

参考文献：

Design, synthesis, and biological evaluation of novel trifluoromethyl indoles as potent HIV-1 NNRTIs with an improved drug resistance profile

Jiang, Hai-Xia; et al, Organic & Biomolecular Chemistry, 2014, 12(21), 3446-3458

合成路线：1 步

956903-52-9

_60%

87802-11-7

反应条件：

1.1 rt; rt → 60 °C; 0.5 h, 60 °C

参考文献：

Simple syntheses of 5-fluoro/ chloro/ bromoindole-2-methanols and 5-fluoro/ chloro/ bromoindole-2-aldehydes

Narayana, B.; et al, Organic Chemistry: An Indian Journal, 2006, 2(1-3), 5-9

合成路线：1 步

174265-12-4

5680-79-5

_78%

87802-11-7

反应条件：

1.1 Reagents: Cesium carbonate Catalysts: Copper oxide (Cu2O) Solvents: N-Methyl-2-pyrrolidone ; rt; 16 h, rt → 100 °C; 100 °C → rt
1.2 Solvents: Ethyl acetate , Water ; rt

参考文献：

Ligand-Free Copper-Catalyzed One-Pot Synthesis of Indole-2-carboxylic Esters

Zhu, Zhiqiang; et al, European Journal of Organic Chemistry, 2014, 2014(3), 511-514

合成路线：1 步

_68%

反应条件：

1.1 Reagents: Diisopropylethylamine Catalysts: Triphenylphosphine , Dichlorobis(triphenylphosphine)palladium Solvents: Methanol , Tetrahydrofuran ; 10 atm, rt; 20 h, 110 °C

参考文献：

Tandem Palladium-Catalyzed N,C-Coupling/Carbonylation Sequence for the Synthesis of 2-Carboxyindoles

Vieira, Tiago O.; et al, Organic Letters, 2008, 10(21), 4899-4901

合成路线：1 步

888723-78-2

_61%

87802-11-7

反应条件：

1.1 Reagents: Aluminum chloride Solvents: Dichloromethane ; 24 h, 20 °C

参考文献：

Regioselective and versatile synthesis of indoles via intramolecular Friedel-Crafts heteroannulation of enaminones

Cruz, Maria del Carmen; et al, Synlett, 2006, (5), 749-755

合成路线：1 步

888723-78-2

_33%

87802-11-7

反应条件：

1.1 Reagents: Iodine ; 60 min, rt

参考文献：

Iodine-mediated one-pot synthesis of indoles and 3-dimethylaminoindoles via annulation of enaminones

Jerezano, Alberto V.; et al, ARKIVOC (Gainesville, 2014, (3), 18-53

合成路线：1 步

63069-48-7

55477-80-0

_26%

87802-11-7

反应条件：

1.1 Reagents: Sodium formate , Sodium bicarbonate , Tetrabutylammonium chloride , Sodium chloride Catalysts: Palladium diacetate ; rt; 1 h; cooled
1.2 Solvents: Acetic anhydride ; overnight, reflux

参考文献：

Solvent-free Heck-Jeffery reactions under ball-milling conditions applied to the synthesis of unnatural amino acids precursors and indoles

Tullberg, Erik; et al, Synthesis, 2006, (7), 1183-1189

合成路线：1 步

2138312-84-0

_21%

87802-11-7

反应条件：

1.1 Catalysts: Silver triflate Solvents: Dimethylformamide ; 1 min, rt; 15 min, 120 °C

参考文献：

Synthesis of 2-Acylindoles via Ag- and Cu-Catalyzed anti-Michael Hydroamination of β-(2-Aminophenyl)-α,β-ynones: Experimental Results and DFT Calculations

Rode, Navnath D.; et al, Journal of Organic Chemistry, 2018, 83(12), 6354-6362

合成路线：2 步

反应条件：

1.1 -
1.2 -
1.3 -
2.1 Catalysts: Silver triflate Solvents: Dimethylformamide ; 1 min, rt; 15 min, 120 °C

参考文献：

Synthesis of 2-Acylindoles via Ag- and Cu-Catalyzed anti-Michael Hydroamination of β-(2-Aminophenyl)-α,β-ynones: Experimental Results and DFT Calculations

Rode, Navnath D.; et al, Journal of Organic Chemistry, 2018, 83(12), 6354-6362

合成路线：2 步

1073-69-4

600-22-6

87802-11-7

反应条件：

1.1 Solvents: Methanol ; reflux
2.1 Catalysts: Sulfuric acid Solvents: Methanol ; 2.5 h, reflux

参考文献：

Design, synthesis, and biological evaluation of novel trifluoromethyl indoles as potent HIV-1 NNRTIs with an improved drug resistance profile

Jiang, Hai-Xia; et al, Organic & Biomolecular Chemistry, 2014, 12(21), 3446-3458

合成路线：2 步

131770-31-5

4637-24-5

87802-11-7

反应条件：

1.1 rt → 120 °C; 12 h, 120 °C
2.1 Reagents: Iodine ; 60 min, rt

参考文献：

Iodine-mediated one-pot synthesis of indoles and 3-dimethylaminoindoles via annulation of enaminones

Jerezano, Alberto V.; et al, ARKIVOC (Gainesville, 2014, (3), 18-53

合成路线：2 步

131770-31-5

4637-24-5

87802-11-7

反应条件：

1.1 5 h, 90 °C
2.1 Reagents: Aluminum chloride Solvents: Dichloromethane ; 24 h, 20 °C

参考文献：

Regioselective and versatile synthesis of indoles via intramolecular Friedel-Crafts heteroannulation of enaminones

Cruz, Maria del Carmen; et al, Synlett, 2006, (5), 749-755

合成路线：2 步

1816-92-8

587-04-2

87802-11-7

反应条件：

1.1 Reagents: Sodium Solvents: Methanol ; -10 °C
2.1 Solvents: Xylene ; 2 h, 140 °C

参考文献：

Extending the versatility of the Hemetsberger-Knittel indole synthesis through microwave and flow chemistry

Ranasinghe, Nadeesha; et al, Bioorganic & Medicinal Chemistry Letters, 2013, 23(6), 1740-1742

合成路线：2 步

20028-53-9

2605-67-6

87802-11-7

反应条件：

1.1 Solvents: Toluene ; reflux
1.2 Reagents: Sodium nitrite , Hydrochloric acid Solvents: Ethanol , Water ; 5 min, 0 °C; 0.5 h, 0 °C
1.3 Reagents: Sodium azide Solvents: Water ; 15 min, 0 °C; 3 h, 0 °C
2.1 Catalysts: 5,10,15,20-Tetrakis(pentafluorophenyl)porphyrinatoiron(III) chloride Solvents: 1,2-Dichloroethane ; rt → reflux; 24 h, reflux

参考文献：

[Fe(F20TPP)Cl] catalyzed intramolecular C-N bond formation for alkaloid synthesis using aryl azides as nitrogen source

Liu, Yungen; et al, Chemical Communications (Cambridge, 2010, 46(37), 6926-6928

合成路线：3 步

106-47-8

96-32-2

87802-11-7

反应条件：

1.1 Reagents: Potassium carbonate , Potassium iodide Solvents: Acetone ; 12 h, 60 °C
2.1 rt → 120 °C; 12 h, 120 °C
3.1 Reagents: Iodine ; 60 min, rt

参考文献：

Iodine-mediated one-pot synthesis of indoles and 3-dimethylaminoindoles via annulation of enaminones

Jerezano, Alberto V.; et al, ARKIVOC (Gainesville, 2014, (3), 18-53

合成路线：3 步

106-47-8

96-32-2

87802-11-7

反应条件：

1.1 Reagents: Potassium carbonate Solvents: Acetone ; 1 h, 60 °C
1.2 12 h, 60 °C
2.1 5 h, 90 °C
3.1 Reagents: Aluminum chloride Solvents: Dichloromethane ; 24 h, 20 °C

参考文献：

Regioselective and versatile synthesis of indoles via intramolecular Friedel-Crafts heteroannulation of enaminones

Cruz, Maria del Carmen; et al, Synlett, 2006, (5), 749-755

合成路线：1 步

944275-74-5

_84%

87802-11-7

940960-50-9

反应条件：

1.1 Catalysts: Rhodium, tetrakis[μ-(2,2,3,3,4,4,4-heptafluorobutanoato-κO:κO′)]di-, (Rh-Rh) ; rt → 60 °C; 16 h, 60 °C; 60 °C → rt

参考文献：

Intramolecular C-H Amination Reactions: Exploitation of the Rh2(II)-Catalyzed Decomposition of Azidoacrylates

Stokes, Benjamin J.; et al, Journal of the American Chemical Society, 2007, 129(24), 7500-7501

合成路线：2 步

反应条件：

1.1 Reagents: Sodium methoxide Solvents: Methanol ; 20 min, -20 °C; -20 °C → -10 °C; 4 h, -10 °C
2.1 Catalysts: Rhodium, tetrakis[μ-(2,2,3,3,4,4,4-heptafluorobutanoato-κO:κO′)]di-, (Rh-Rh) ; rt → 60 °C; 16 h, 60 °C; 60 °C → rt

参考文献：

Intramolecular C-H Amination Reactions: Exploitation of the Rh2(II)-Catalyzed Decomposition of Azidoacrylates

Stokes, Benjamin J.; et al, Journal of the American Chemical Society, 2007, 129(24), 7500-7501

5-氯吲哚-2-羧酸甲酯(87802-11-7)上下游

5-氯吲哚-2-羧酸对氯苯胺对氯苯肼盐酸盐 Glycine, N-(4-chlorophenyl)-, methyl ester 2-溴-5-氯苯甲醛 Methylene, oxo- 2-叔丁氧羰基氨基丙烯酸甲酯甘氨酸甲酯盐酸盐 4-氯-2-碘苯胺

5-氯吲哚-2-羧酸甲酯(87802-11-7)参考资料

Reaxys RN：

PubChem CID：

4777711

5-氯吲哚-2-羧酸甲酯(87802-11-7) MSDS

基础信息

Material Safety Data Sheet

Section 1. Identi?cation of the substance
Product Name: 5-Chloroindole-2-carboxylic acid methyl ester
Synonyms:

Section 2. Hazards identi?cation
Harmful by inhalation, in contact with skin, and if swallowed.

Section 3. Composition/information on ingredients.
Ingredient name: 5-Chloroindole-2-carboxylic acid methyl ester
CAS number: 87802-11-7

Section 4. First aid measures
    Skin contact:        Immediately wash skin with copious amounts of water for at least 15 minutes while removing
    contaminated clothing and shoes. If irritation persists, seek medical attention.
    Eye contact:        Immediately wash skin with copious amounts of water for at least 15 minutes. Assure adequate
    ?ushing of the eyes by separating the eyelids with ?ngers. If irritation persists, seek medical
    attention.
    Inhalation:        Remove to fresh air. In severe cases or if symptoms persist, seek medical attention.
    Ingestion:        Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.

Section 5. Fire ?ghting measures
    In the event of a ?re involving this material, alone or in combination with other materials, use dry
    powder or carbon dioxide extinguishers. Protective clothing and self-contained breathing apparatus
    should be worn.

Section 6. Accidental release measures
    Personal precautions: Wear suitable personal protective equipment which performs satisfactorily and meets local/state/national
    standards.
    Respiratory precaution:        Wear approved mask/respirator
    Hand precaution:        Wear suitable gloves/gauntlets
    Skin protection:        Wear suitable protective clothing
    Eye protection:        Wear suitable eye protection
    Methods for cleaning up: Mix with sand or similar inert absorbent material, sweep up and keep in a tightly closed container
    for disposal. See section 12.
    Environmental precautions: Do not allow material to enter drains or water courses.

Section 7. Handling and storage
    Handling:        This product should be handled only by, or under the close supervision of, those properly quali?ed
    in the handling and use of potentially hazardous chemicals, who should take into account the ?re,
    health and chemical hazard data given on this sheet.
    Store in closed vessels, refrigerated.
    Storage:

Section 8. Exposure Controls / Personal protection
    Engineering Controls: Use only in a chemical fume hood.
    Personal protective equipment: Wear laboratory clothing, chemical-resistant gloves and safety goggles.
    General hydiene measures: Wash thoroughly after handling. Wash contaminated clothing before reuse.

Section 9. Physical and chemical properties
    Appearance:        Not speci?ed
    Boiling point:        No data
    No data
    Melting point:
    Flash point:        No data
    Density:        No data
    Molecular formula:        C10H8ClNO2
    Molecular weight:        209.6

Section 10. Stability and reactivity
    Conditions to avoid: Heat, ?ames and sparks.
    Materials to avoid: Oxidizing agents.
    Possible hazardous combustion products: Carbon monoxide, nitrogen oxides, hydrogen chloride.

Section 11. Toxicological information
No data.

Section 12. Ecological information
No data.

Section 13. Disposal consideration
Arrange disposal as special waste, by licensed disposal company, in consultation with local waste
disposal authority, in accordance with national and regional regulations.

Section 14. Transportation information
Non-harzardous for air and ground transportation.

Section 15. Regulatory information
    No chemicals in this material are subject to the reporting requirements of SARA Title III, Section
    302, or have known CAS numbers that exceed the threshold reporting levels established by SARA
    Title III, Section 313.

SECTION 16 - ADDITIONAL INFORMATION
N/A