1H-indole

• ChemBase编号: 4103
• 分子式: C8H7N
• 平均质量: 117.14788
• 单一同位素质量: 117.05784923
• SMILES: c1ccc2[nH]ccc2c1
• Canonical SMILES: c1ccc2c(c1)[nH]cc2
• InChI: InChI=1S/C8H7N/c1-2-4-8-7(3-1)5-6-9-8/h1-6,9H
• InChIKey: SIKJAQJRHWYJAI-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 1H-indole; indole
• IUPAC传统名: indole; @indole
• 别名: 2,3-苯并吡咯; 吲哚; 2,3-Benzopyrrole; 1H-Indole; Indole; 2,3-Benzopyrrole, ketole; 1-benzazole; 1H-Benzo[b]pyrrole; Indole; 1H-Indole, 1-Azaindene; Benzo[b]pyrrole; Ketole; NSC 1964

登记号

• CAS号: 120-72-9
• EC号: 204-420-7
• MDL号: MFCD00005607
• Beilstein号: 107693
• 默克索引号: 144963
• PubChem SID: 24874767; 160967536; 24856309; 24867930; 24901173; 46508707; 24896037
• PubChem CID: 798
• CHEBI ID: 16881
• CHEMBL: 15844
• Chemspider ID: 776
• FEMA编号: 2593
• KEGG ID: C00463
• 美国药典/FDA物质标识码: 8724FJW4M5
• 维基百科标题: Indole
• 欧洲委员会编号: 560
• Flavis Number: 14.007

理论计算性质

JChem

• Acid pKa: 16.437037
• 质子受体: 0
• 质子供体: 1
• LogD (pH = 5.5): 2.072008
• LogD (pH = 7.4): 2.072008
• Log P: 2.072008
• 摩尔折射率: 37.1445 cm^3
• 极化性: 15.66808 Å^3
• 极化表面积: 15.79 Å^2
• 可自由旋转的化学键: 0
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 2.29
• LOG S: -1.34
• 溶解度: 5.31e+00 g/l

分子性质

理化性质

• 溶解度: 0.19 g/100 ml (20 °C); Soluble in hot water; Chloroform; Methanol; methanol: soluble0.1 g/mL, clear
• 外观: Off-White Solid; White solid
• 熔点: 47-52°C; 50-53 °C; 50-54°C; 51-54 °C(lit.); 52–54 °C; 52-54°C; 52-54°C
• 沸点: 253-254 °C(lit.); 253-254°C; 253-254°C; 253–254°C (526 K)
• 闪点: 121 °C; 121°C; 121°C(249°F); 249.8 °F
• 密度: 1.1747 g/cm^3, solid; 1.22; 1.220
• pKa: 16.2; (21.0 in DMSO)
• pKb: 17.6
• 感官: butter; cheese; chocolate; grape; honey; jasmine; musty; fatty; floral; vanilla; vegetable; earthy; fishy; wine-like; animal

安全信息

• 保存条件: 2-8°C; Refrigerator
• 保存注意事项: Light Sensitive; Toxic/Corrosive/Harmful/Irritant/Air Sensitive/Light Sensitive/Stench/Keep Cold/Store under Argon
• RTECS编号: NL2450000
• 欧盟危险性物质标志: 环境危害性(Nature polluting) (N); X; 有害性(Harmful) (Xn)
• 联合国危险货物编号: 2811; UN2811
• 德国WGK号: 1
• 联合国危险货物等级: 6.1
• 联合国危险货物包装类别(PG): 3; III
• 澳大利亚Hazchem: 2X
• 危险公开号: 21/22-37/38-41-50/53; 21/22-41-50; R:22-27-36/37/38
• 安全公开号: 26-36/37/39-57-60; 26-36/37/39-60-61; R R: 21/22-37/38-41-50/53; S: 26-36/37/39-60-61; S:25-26-36/37/39
• 欧盟危险货物分类: T2
• 欧盟危险识别号(EUHIN): 6.1B
• 美国ERG指导号: 154
• TSCA收录: 是
• GHS危险品标识: GHS05; GHS06; GHS09
• GHS警示词: Danger
• GHS危险声明: H302-H311-H315-H318-H335-H400; H311-H302-H318-H400
• GHS警示性声明: P261-P273-P280-P305 + P351 + P338-P312; P280-P305+P351+P338-P361-P302+P352-P405-P501A
• 个人保护装置: dust mask type N95 (US), Eyeshields, Faceshields, Gloves
• RID/ADR: UN 2811 6.1/PG 3
• Regulation Compliance: FCC; FDA 21 CFR (172.515)

药理学性质

• 过敏源: no known allergens

产品相关信息

• 纯度: ≥98.5% (GC); ≥99%; 95+%; 98%; 99%
• 级别: analytical standard; Kosher; NI; puriss.
• 包装: ampule of 1000 mg
• Empirical Formula (Hill Notation): C8H7N

详细说明

MP Biomedicals - 02102036

Crystalline

DrugBank - DB04532

Drug information: experimental

Sigma Aldrich - W259306

Biochem/physiol Actions
0.3-2ppm 时的味道
Other Notes
天然存在：白肋烟草、黄油、咖啡、鲣鱼干、蛋，鱼、麦芽、朗姆酒、茶叶和葡萄酒。
包装
1 kg in glass bottle
1 sample in glass bottle
10, 25 kg in poly drum
100 g in glass bottle

Sigma Aldrich - I3408

包装
25, 100, 500 g in glass bottle

Sigma Aldrich - 269077

包装
100 g in glass bottle

Toronto Research Chemicals - I577320

Can be used in perfumes and in the synthesis of tryptophan.

参考文献

• Treatment of the carbamate with Tri-n-butyltin chloride, A10746, followed by Stille coupling enables synthesis of 2-aryl- and 2-vinylindoles: J. Org. Chem., 60, 6218 (1995).
• Lithiation of N-protected indoles usually occurs at the 2-position, e.g. benzenesulfonation of the 1-lithio derivative, 2-lithiation with LDA and treatment with pyridine-3,4-dicarboxylic anhydride. This sequence has been reported in a synthetic route to ellipticene and olivacine: J. Org. Chem., 57, 5891 (1992).
• Regioselective synthesis of 3-substituted indoles has been described using a sequence of N-silylation, 3-bromination of the 1-TBDMS detivative with NBS, 3-lithiation, treatment with an electrophile to introduce the 3-substituent, and desilylation with TBAF. Good overall yields are obtained for a range of electrophiles: J. Org. Chem., 59, 10 (1994); Org. Synth. Coll., 9, 417 (1998).
• Halogenation in the 2-position has been effected via the Li 1-carbamate and subsequent 2-lithiation: J. Org. Chem., 57, 2495 (1992):
  
• Treatment with EtMgI followed by ZnCl₂ leads to an N-zinc derivative. This undergoes acylation at the 3-position: Tetrahedron, 46, 6061 (1990).