2-bromothiophene

• ChemBase编号: 8512
• 分子式: C4H3BrS
• 平均质量: 163.03562
• 单一同位素质量: 161.9138831
• SMILES: c1ccsc1Br
• Canonical SMILES: Brc1cccs1
• InChI: InChI=1S/C4H3BrS/c5-4-2-1-3-6-4/h1-3H
• InChIKey: TUCRZHGAIRVWTI-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 2-bromothiophene
• IUPAC传统名: 2-bromothiophene
• 别名: 2-噻吩基溴; 2-溴噻吩; 2-Thienyl bromide; 2-Bromothiophene; 2-Bromothiophene 98%; NSC 4456; 2-Bromothiophene

登记号

• CAS号: 1003-09-4
• EC号: 213-699-4
• MDL号: MFCD00005417
• Beilstein号: 104663
• PubChem SID: 160971819; 24847601
• PubChem CID: 13851

理论计算性质

• 质子受体: 0
• 质子供体: 0
• LogD (pH = 5.5): 2.6884363
• LogD (pH = 7.4): 2.6884363
• Log P: 2.6884363
• 摩尔折射率: 29.9465 cm^3
• 极化性: 11.968581 Å^3
• 极化表面积: 0.0 Å^2
• 可自由旋转的化学键: 0
• 里宾斯基五规则: true

分子性质

理化性质

• 熔点: <-10°C
• 沸点: 149-151 °C(lit.); 149-151°C; 149-152°C
• 闪点: 125.6 °F; 52 °C; 52°C; 58°C(136°F)
• 密度: 1.684; 1.684 g/mL at 25 °C(lit.); 1.7; 1.701
• 折射率: 1.586; 1.5860; n20/D 1.586(lit.)

安全信息

• 保存注意事项: Light Sensitive; TOXIC, FLAMMABLE; Very Toxic/Flammable/Stench/Light Sensitive/Keep Cold
• 欧盟危险性物质标志: 有毒(Toxic) (T)
• 联合国危险货物编号: 2929; UN2929
• 德国WGK号: 3
• 联合国危险货物等级: 6.1
• 联合国危险货物包装类别(PG): 2; II
• 危险公开号: 10-25-41; 23/24/25-36/38
• 安全公开号: 26-36/37/39-45; 9-26-27-36/37/39-45-60
• TSCA收录: true; 是
• GHS危险品标识: GHS02; GHS05; GHS06
• GHS警示词: Danger
• GHS危险声明: H226-H300-H318; H300-H310-H330-H315-H319-H226
• GHS警示性声明: P210-P301+P310-P303+P361+P353-P304+P340-P305+P351+P338-P320-P330-P361-P405-P501A; P264-P280-P301 + P310-P305 + P351 + P338
• 个人保护装置: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 2929 6.1/PG 2
• 保存温度: 2-8°C

产品相关信息

• 纯度: 97%; 98%; 98+%
• Empirical Formula (Hill Notation): C4H3BrS

详细说明

Sigma Aldrich - 124168

Application
用 CuBr-LiBr 偶联剂和氯甲酸酯处理衍生的格氏试剂，易于制得 2-噻吩基酯。1
包装
10, 50, 250 g in glass bottle

参考文献

• The bromo-substituent can be readily displaced by methoxide in methanol in the presence of a Cu(I) catalyst: Synth. Commun., 20, 213 (1990). For coupling reaction with Thiophene-2-thiol, B22642, in the presence of Cu₂O, to give 2,2'-dithienyl sulfide, see: Org. Synth. Coll., 6, 558 (1988).
• Allylic alcohols are thienylated by means of a Heck-type, Pd-catalyzed coupling reaction; the products are ketones formed by rearrangement: Chem. Lett., 423 (1977). Coupling with iodoarenes can be induced at the 5-position by the use of a palladium(II) catalyst in the presence of silver nitrate and potassium fluoride, providing access to 5-aryl-2-bromothiophene derivatives, which may be further elaborated by reaction with the available 2-bromo-substituent: Org. Lett., 7, 5083 (2005).