2,2-dimethylpropanoyl chloride

• ChemBase编号: 103485
• 分子式: C5H9ClO
• 平均质量: 120.57736
• 单一同位素质量: 120.03419259
• SMILES: CC(C)(C)C(=O)Cl
• Canonical SMILES: ClC(=O)C(C)(C)C
• InChI: InChI=1S/C5H9ClO/c1-5(2,3)4(6)7/h1-3H3
• InChIKey: JVSFQJZRHXAUGT-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 2,2-dimethylpropanoyl chloride
• IUPAC传统名: 2,2-dimethylpropanoyl chloride
• 别名: 新戊酰氯; 三甲基乙酰氯; 新戊酰氯; 三甲基乙酰氯; Pivaloyl chloride; Pivaloyl chloride; Trimethylacetyl chloride; Trimethylacetyl chloride; PIVALOYL CHLORIDE

登记号

• CAS号: 3282-30-2
• EC号: 221-921-6
• MDL号: MFCD00000709
• Beilstein号: 385668
• PubChem SID: 162103128; 24900440; 24887589
• PubChem CID: 62493

理论计算性质

• 质子受体: 1
• 质子供体: 0
• LogD (pH = 5.5): 2.1095204
• LogD (pH = 7.4): 2.1095204
• Log P: 2.1095204
• 摩尔折射率: 30.2046 cm^3
• 极化性: 11.899294 Å^3
• 极化表面积: 17.07 Å^2
• 可自由旋转的化学键: 1
• 里宾斯基五规则: true

分子性质

理化性质

• 熔点: -57°C
• 沸点: 105-106 °C(lit.); 105-106°C; 105-106°C
• 闪点: 19 °C; 66.2 °F; 8.8°C; 8°C(46°F)
• 密度: 0.979 g/ml; 0.979 g/mL at 25 °C(lit.); 0.980 g/mL at 20 °C; 0.985
• 折射率: 1.4120; n20/D 1.412; n20/D 1.412(lit.)
• 蒸汽压: 36 mmHg ( 20 °C)
• 蒸汽密度: >1 (vs air)

安全信息

• 保存条件: 2-8°C, Desiccate
• 保存注意事项: Moisture Sensitive
• 欧盟危险性物质标志: 腐蚀性(Corrosive) (C); 易燃性(Flammable) (F); 剧毒(Highly toxic) (T+)
• 联合国危险货物编号: 2438; UN2438
• 德国WGK号: 1
• 联合国危险货物等级: 3/8; 6.1
• 联合国危险货物包装类别(PG): 1; I; Truck Only
• 澳大利亚Hazchem: 2WE
• 危险公开号: 11-14-22-26-34; R:11-35
• 安全公开号: 16-26-36/37/39-45; 4-8-9-16-20-23-26-28-30-33-36/37/39-45; S:16-27/28-29-36/37/39-45
• 欧盟危险货物分类: TF1
• 欧盟危险识别号(EUHIN): 6.1A
• 美国ERG指导号: 132
• TSCA收录: 是
• GHS危险品标识: GHS02; GHS05; GHS06
• GHS警示词: Danger
• GHS危险声明: H225-H301-H330-H314-H318; H225-H302-H314-H330
• GHS警示性声明: P210-P260-P280-P284-P305 + P351 + P338-P310; P210-P301+P310-P303+P361+P353-P304+P340-P305+P351+P338-P320-P330-P405-P501A
• 个人保护装置: Faceshields, full-face respirator (US), Gloves, Goggles, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 2438 6.1/PG 1
• 欧盟补充危害声明: Reacts violently with water.

产品相关信息

• 纯度: ≥98.0% (GC); 98+%; 99%
• 级别: purum
• 线性分子式: (CH3)3CCOCl

详细说明

MP Biomedicals - 02151905

Reagent for mixed anhydride peptide synthesis.
1 ml = approx. 0.98 g

Sigma Aldrich - T72605

包装
5, 100, 500 mL in glass bottle
Application
广泛用作胺1、席夫碱2和吡咯烷酮3的 N-酰化剂，以及醇4、内酯5和糖类6的 O-酰化剂。

参考文献

• In the presence of Cu(I) halides, reacts with Grignard and organolithium reagents to give t-butyl ketones: Tetrahedron Lett., 829 (1971).
• Activates heteroaromatic amines to ring-lithiation. For example: Synthesis, 670 (1986):
  
• Reacts with sodium formate to give the mixed formic pivalic anhydride, a highly effective reagent for N-formylation: Rec. Trav. Chim., 101, 460 (1982). Similarly, has been used to form mixed anhydrides, particularly of N-protected amino acids and peptides, prior to coupling: Coll. Czech. Chem. Commun., 27, 1273 (1962). The sterically-hindered nature of the pivaloyl group greatly reduces attack at the 'wrong' carbonyl group. For peptide reagents, see Appendix 6.
• Has also been used as a reagent for protection of alcohols as their pivaloyl (Pv) esters, allowing selective acylation of a primary over a secondary alcohol: Synthesis, 453 (1986); selective protection of the less hindered of two primary alcohols is possible: J. Chem. Soc., Chem. Commun., 354 (1988). See also Trimethylacetic anhydride, B22983. Cleavage is by room temperature basic hydrolysis: Tetrahedron Lett., 317 (1973); 3561 (1979); J. Org. Chem., 42, 918 (1977), or methanolysis: J. Am. Chem. Soc., 112, 3693 (1990), or a number of other methods, including aqueous methylamine: Tetrahedron, 24, 639 (1968).