2-methylpropane-2-peroxol

• ChemBase编号: 105404
• 分子式: C4H10O2
• 平均质量: 90.121
• 单一同位素质量: 90.06807956
• SMILES: CC(C)(C)OO
• Canonical SMILES: OOC(C)(C)C
• InChI: InChI=1S/C4H10O2/c1-4(2,3)6-5/h5H,1-3H3
• InChIKey: CIHOLLKRGTVIJN-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 2-methylpropane-2-peroxol
• IUPAC系统名: 2-Methylpropane-2-peroxol
• IUPAC传统名: tert-butyl hydroperoxide
• 别名: 叔丁基过氧化氢 溶液; Luperox® TBH70X, 叔丁基过氧化氢 溶液; 叔丁基过氧化氢 溶液; 叔丁基过氧化氢; tert-Butyl hydroperoxide solution; Luperox® TBH70X, tert-Butyl hydroperoxide solution; Cadox TBH; Hydroperoxyde de Butyle Tertiaire; tert-Bytyl hydroperoxide; 1,1-Dimethylethyl hydroperoxide; Perbutyl H; terc. Butylhydroperoxid; t-BUTYL HYDROPEROXIDE 70% SOLUTION; Tert-Butyl hydroperoxide; 2-Hydroperoxy-2-methylpropane; TBHP; tert-Butyl hydroperoxide solution; tert-Butyl hydroperoxide

登记号

• CAS号: 75-91-2
• EC号: 200-915-7
• MDL号: MFCD00002130
• Beilstein号: 1098280
• 默克索引号: 141570
• PubChem SID: 24851948; 24851951; 24851944; 24866199; 162092551; 24865918; 24869433
• PubChem CID: 6410
• CHEMBL: 348399
• Chemspider ID: 6170
• 医学主题词(MeSH): tert-Butylhydroperoxide
• 美国药典/FDA物质标识码: 955VYL842B
• 维基百科标题: Tert-Butyl_hydroperoxide

理论计算性质

• Acid pKa: 11.71938
• 质子受体: 2
• 质子供体: 1
• LogD (pH = 5.5): 0.98471767
• LogD (pH = 7.4): 0.9846972
• Log P: 0.98471797
• 摩尔折射率: 23.4171 cm^3
• 极化性: 9.428219 Å^3
• 极化表面积: 29.46 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

• 溶解度: miscible in water
• 外观: Colourless liquid
• 熔点: -3°C; -3°C; -34°C
• 沸点: 37°C (at 2.0 kPa); 96 °C; 96.2 °C; 96°C dec.
• 闪点: 107.6 °F; 109.4 °F; 29 °C; 42 °C; 43 °C (closed cup); 43 °C; 43°C(109°F); 84.2 °F
• 自燃点: 238 °C
• 密度: 0.808 g/mL at 25 °C; 0.817 g/mL at 25 °C; 0.82 g/mL at 20 °C; 0.83 g/mL at 20 °C; 0.90 g/mL at 20 °C; 0.93 g/mL at 25 °C; 0.937; 0.937 g/mL at 20 °C; 0.94 g/mL at 25 °C(lit.); 935 - 964 kg/m3 at 25 °C; 935 mg cm^-3
• 折射率: 1.3870; n20/D 1.386; n20/D 1.387; n20/D 1.397; n20/D 1.399; n20/D 1.400; n20/D 1.402; n20/D 1.403
• 蒸汽压: ca. 30.7 hPa at 21 °C
• 分配系数: 1.23
• pKa: 12.69
• pKb: 1.31
• 标准摩尔燃烧焓 (ΔcH^o298): 2.705-2.715 MJ mol^-1
• 标准摩尔生成焓 (ΔfH^o298): -299–-289 kJ mol^-1

安全信息

• 保存条件: 2-8°C
• RTECS编号: EQ4900000
• 欧盟危险性物质标志: 腐蚀性(Corrosive) (C); 易燃性(Flammable) (F); 环境危害性(Nature polluting) (N); 氧化性(Oxidising) (O); 有毒(Toxic) (T); X; 有害性(Harmful) (Xn)
• 联合国危险货物编号: 3103; 3105; 3109; UN3109
• 德国WGK号: 3
• 联合国危险货物等级: 5.2
• 联合国危险货物包装类别(PG): II
• 澳大利亚Hazchem: 2W
• 危险公开号: 7-10-20/21/22-34-52/53; 7-10-21/22-23-34-43-51/53-65-68; 7-10-21/22-23-34-43-51/53-68; R:7-10-18-20/21/22-34; R7, R10, R20/21/22, R34, R43 R52/53
• 安全公开号: 3/7-14-26-36/37/39-45-47-61; 3/7-14-26-36/37/39-45-61; 3/7-14-26-36/37/39-45-61-62; 3/7-17-26-36/37/39-43-45-47-61; 3/7-17-26-36/37/39-43-45-61; 3/7-17-26-36/37/39-45-61; 3/7-26-36/37/39-45-61; S:7-3/9/14-16-36/37/39; S3/7, S14, S16, S17, S24, S36/37/39, S45, S61
• 欧盟危险货物分类: P1
• 欧盟危险识别号(EUHIN): 5.2
• 美国ERG指导号: 145
• TSCA收录: 是
• GHS危险品标识: GHS corrosion; GHS environment; GHS flame; GHS health hazard; GHS skull and crossbones; GHS02; GHS05; GHS06; GHS08; GHS09
• GHS警示词: DANGER; Danger
• NFPA704:
  

  4

  4

  4

  OX
• GHS危险声明: 226, 242, 302, 311, 314, 317, 331, 341, 411; H226-H242-H302-H304-H311 + H331-H314-H317-H336-H341-H411; H226-H242-H302-H304-H311 + H331-H314-H317-H341-H411; H226-H242-H302-H311-H314-H317-H330-H341-H411; H226-H242-H302-H311-H314-H317-H331-H341-H411; H226-H302-H304-H311 + H331-H314-H317-H336-H341-H411; H226-H302-H304-H311 + H331-H314-H317-H341-H411; H311-H331-H302-H314-H318-H226-H242-H402-H412
• GHS警示性声明: 220, 261, 273, 280, 305+351+338, 310; P220-P260-P273-P280-P284-P305 + P351 + P338; P220-P261-P273-P280-P301 + P310-P305 + P351 + P338; P220-P261-P273-P280-P305 + P351 + P338-P310; P261-P273-P280-P301 + P310-P305 + P351 + P338-P310; P280-P235-P305+P351+P338-P309-P310-P420B
• 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 3103 5.2; UN 3105 5.2; UN 3109 5.2
• 保存温度: 2-8°C

产品相关信息

• 纯度: 70% aq. soln.
• 浓度: ~5.5 M in decane (over molecular sieve 4Å); ~5.5 M in nonane (over molecular sieve 4 Å); ~70% in H2O; ~80% in di-tert-butyl peroxide/water 3:2; 5.0-6.0 M in decane; 5.0-6.0 M in nonane; 70 wt. % in H2O; 70% in H2O
• 级别: CP; purum
• 杂质: <4% water
• 品质说明: packed in FEP bottles
• 线性分子式: (CH3)3COOH

详细说明

MP Biomedicals - 02190049

70% Aqueous solution
1 ml = approx. 0.93 g

Sigma Aldrich - 418064

包装
50 mL in poly bottle
Protocols & Applications
Asymmetric Epoxidation of Allylic Alcohols
Asymmetric Epoxidation of Homoallylic Alcohols
Asymmetric Ketone Hydrogenation
Asymmetric Transfer Hydrogenation

Sigma Aldrich - 416665

包装
25, 100 mL in poly bottle

Sigma Aldrich - 19999

Other Notes
Safe and stable oxidant for the Sharpless epoxidation1,2Reactant also used as a redox initiator3 and oxidant4
包装
25, 100 mL in PFA/FEP btl

Sigma Aldrich - 458139

包装
1, 4 L in poly bottle
18 L in poly drum
25, 100 mL in poly bottle
Legal Information
Arkema Inc. 产品
法律信息
Luperox 注册商标 Arkema Inc.
Application
用于氧化反应的多功能试剂。1,2,3,4

Sigma Aldrich - 19997

Other Notes
用于 Sharpless 环氧化反应的安全而稳定的氧化剂。1,2
包装
25, 100 mL in PFA/FEP btl

Sigma Aldrich - 19990

包装
100, 500 mL in poly bottle

参考文献

• In combination with Mo(CO)₆ or Cr(CO)₆, oxidizes alkenes at allylic positions to give ɑ?-unsaturated ketones: J. Chem. Soc., Perkin 1, 267 (1985); Tetrahedron Lett., 25, 1235 (1984). Terminal alkynes are converted to methyl ketones in high yield in the presence of catalytic quantities of Pd(OAc)₂: J. Org. Chem., 45, 5387 (1980).
• In the presence of MoO₂(acac)₂, silyl enol ethers are cleaved in high yield, as an alternative to ozonolysis: Tetrahedron Lett., 22, 2595 (1981).
• In the presence of Dichlorotris(triphenylphosphine)ruthenium(II), L00373, secondary amines are dehydrogenated to imines: J. Chem. Soc., Chem. Commun., 613 (1985), and aryl or alkenyl cyanohydrins to acyl cyanides: Tetrahedron Lett., 26, 925 (1985).
• The anhydrous reagent can be prepared, e.g. in dilute toluene solution by azeotropic drying: method and safe handling procedure: J. Org. Chem., 48, 3607 (1983). See also: Chem. Ber., 113, 3662 (1980).
• Widely used in combination with various metal catalysts (Mo, Cr, V, W, Ti, etc.) for the epoxidation of alkenes. For a review of metal-catalyzed epoxidations, see: Chem. Rev., 89, 431 (1989).
• In the presence of Ti(O-i-Pr)₄ and (+)- or (-)-dialkyl tartrate, allylic alcohols undergo the Sharpless enantioselective epoxidation: J. Am. Chem. Soc., 102, 5974 (1980). The chirality of the major product is predictable and >95% ee is common:
  
• For reviews, see: Pure Appl. Chem., 55, 589 (1983); Synthesis, 89 (1986); Org. React., 48, 1 (1996). For an example, see: Org. Synth. Coll., 7, 461 (1990).