Di-tert-butyl dicarbonate 二碳酸二叔丁酯

CAS 24424-99-5 MFCD00008805

化学结构图

24424-99-5
SMILES: CC(C)(C)OC(=O)OC(=O)OC(C)(C)C

化学属性

Mol. FormulaC10H18O5
Mol. Weight218.25
Refractive indexn20/D 1.409(lit.)
Boiling Point235.8°C at 760 mmHg
Density0.95
Melting Point22.4-23.8℃
Flash Point37°C
TSCAYes
Stability对热敏感,易吸潮
Danger-Level乙类

别名和识别编码

Chemical NameDi-tert-butyl dicarbonate
CAS Number24424-99-5
Synonym Boc anhydride {LY} Boc anhydride {} {LY} Boc anhydride {} {} {LY} Boc anhydride {} {} {} {LY} Boc anhydride {} {} {} {} {LY} Boc anhydride {} {} {} {} {} {LY} Boc anhydride {} {} {} {} {} {} {LY} Boc anhydride {} {} {} {} {} {} {} { {} {} {} {} {} {} {} {LY} Boc anhydride {} {} {} {} {} {} {} {} {LY} Boc anhydride {} {} {} {} {} {} {} {} {} {LY} Boc anhydride {} {} {} {} {} {} {} {} {} {} {LY} Boc anhydride {} {} {} {} {} {} {} {} {} {} {} {LY} Boc anhydride {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Boc anhydride {} {} {} {} {} {} {} {} {} {} {} {} {} { {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Boc anhydride {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Boc anhydride {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Boc anhydride {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Boc anhydride {} {} {} {} {} {} {} {} {} {} {}
PubChem Substance ID87561558
EC Number246-240-1
Beilstein Registry Number1911173
MDL NumberMFCD00008805
Reaxys-RN1911173
Chemical Name Translation二碳酸二叔丁酯
LabNetwork Molecule IDLN00193323
InChIInChI=1S/C10H18O5/c1-9(2,3)14-7(11)13-8(12)15-10(4,5)6/h1-6H3
Canonical SMILESCC(C)(C)OC(OC(OC(C)(C)C)=O)=O
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分类

  • {SNA} Amine Protection, Chemical Biology, Chemical Synthesis, Other Protecting and Derivatizing Reagents,
  • {SNA} Amine Protection, Chemical Biology, Chemical Synthesis, Others, Peptide Chemistry, Protecting and Derivatizing Reagents, Protection and Derivatization, Synthetic Reagents
  • {SNA} Chemical Reagents, Amine Protection, Chemical Biology,
  • {SNA} Amine Protection,
  • {SNA} Amine Protection, Chemical Biology, Chemical Reagents, Chemical Synthesis, Development Quantities for Research, Other Protecting and Derivatizing Reagents, Peptide Chemistry, Protecting and Derivatizing Reagents, Protection and Derivatization, Synthetic Reagents

产品应用

  • 氨基酸BOC试剂。有机合成中用来引入叔丁氧羰(BOC)保护基团,特别适用于氨基酸的氨基保护。
  • 三叔丁氧羰基保护的肼可以在发色试剂中制备芴甲氧羰基?酯以监测固相醛类。
  • 用于制备叔丁氧羰基保护的胺类的试剂。
  • 用于引入叔丁氧羰基保护基团的试剂。
  • 通过 Lewis 酸催化作用可以保护叔丁氧羰基衍生物等醇类。
  • 通过叔丁氧羰基氨基丙炔与甲醛、二异丙胺以及溴化铜的?反应来制备氨甲基丙二烯,是许多牛血浆胺氧化酶灭活剂?的组分。

相关文献及参考

  • For a brief feature on uses of the reagent in synthesis, see: Synlett, 1995 (2001).
  • The Boc group is readily cleaved with acid, most often Trifluoroacetic acid, L06374.
  • For Boc protection of phenols, alcohols, thiols etc. under phase-transfer conditions, see: Can. J. Chem., 63, 153 (1985).
  • Carboxylic acids have also been converted to Boc-protected amines, via a one-pot Curtius rearrangement, using the reagent in the presence of sodium azide, with catalytic amounts of TBAB and zinc triflate: Org. Lett., 7, 4107 (2005).
  • In the presence of 1 equivalent of DMAP in acetonitrile, arylamines are converted to isocyanates, generally in high yield; the dicarbonate here behaves as a convenient phosgene replacement: Angew. Chem. Int. Ed., 34, 2497 (1995). The same reagent system has also been applied to nitroalkanes for the ambient temperature generation of nitrile oxides which were trapped in situ with dipolarophiles: Synthesis, 309 (1997). Carboxyli
  • Rapid and efficient formation of Boc derivatives of amines, catayzed by Copper(II)­ tetrafluoroborate hexahydrate, 26127 has been described: Tetrahdron Lett., 47, 1087 (2006).
  • Amides can be protected in the presence of a catalytic quantity of DMAP (4-(Dimethyl­amino)­pyridine, A13016): J. Org. Chem., 48, 2424 (1983); Acta Chem. Scand. B, 40, 745 (1986); the amide link of the product undergoes facile alkaline hydrolysis or methanolysis.
  • In the presence of 1 equivalent of DMAP in acetonitrile, arylamines are converted to isocyanates, generally in high yield; the dicarbonate here behaves as a convenient phosgene replacement: Angew. Chem. Int. Ed., 34, 2497 (1995). The same reagent system has also been applied to nitroalkanes for the ambient temperature generation of nitrile oxides which were trapped in situ with dipolarophiles: Synthesis, 309 (1997). Carboxylic acids can be esterified in the presence of a catalytic amount of DMAP: Synlett, 263 (2004).

安全信息

GHS Symbol
WGK Germany3
Hazard statements
  • H225 Highly flammable liquid and vapour 高度易燃液体和蒸气
  • H226 Flammable liquid and vapour 易燃液体和蒸气
  • H228 Flammable solid 易燃固体
  • H315 Causes skin irritation 会刺激皮肤
  • H317 May cause an allergic skin reaction 可能导致皮肤过敏
  • H318 Causes serious eye damage 严重伤害眼睛
  • H319 Causes serious eye irritation 严重刺激眼睛
  • H330 Fatal if inhaled 吸入致命
  • H335 May cause respiratory irritation 可能导致呼吸道刺激
  • H336 May cause drowsiness or dizziness 肯能导致嗜睡或头晕
  • H351 Suspected of causing cancer 怀疑致癌
  • H373 May causes damage to organs through prolonged or repeated exposure 长期或频繁接触可能会损伤器官
Personal Protective Equipment Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
Hazard Codes 6.1 F,T+ F,Xn,N T+
RTECSHT0230000
Precautionary statements
  • P210 Keep away from heat/sparks/open flames/hot surfaces. — No smoking. 远离热源/火花/明火/热的表面。——禁止吸烟。
  • P233 Keep container tightly closed. ?保持容器密闭。
  • P240 Ground/bond container and receiving equipment. 与地面接触/连接集装箱和接受设备。
  • P241 Use explosion-proof electrical/ventilating/lighting/…/equipment. 使用防爆电气/通风/照明/ .../设备。
  • P241+P242+P243
  • P260 Do not breathe dust/fume/gas/mist/vapours/spray. 不要吸入粉尘/烟/气体/烟雾/蒸汽/喷雾。
  • P261 Avoid breathing dust/fume/gas/mist/vapours/spray. 避免吸入粉尘/烟/气体/烟雾/蒸汽/喷雾。
  • P264 Wash hands thoroughly after handling. 处理后要彻底洗净双手。
  • P270 Do not eat, drink or smoke when using this product. 使用本产品时不要吃东西,喝水或吸烟。
  • P271 Use only outdoors or in a well-ventilated area.? 只能在室外或通风良好的地方使用。
  • P280 Wear protective gloves/protective clothing/eye protection/face protection. 戴防护手套/防护服/眼睛的保护物/面部保护物。
  • P284 Wear respiratory protection.? 佩戴呼吸保护装置。
  • P301+P312+P330
  • P302+P350
  • P302+P352+P332+P313+P362+P364
  • P304+P340+P310
  • P305+P351+
  • P305+P351+P338
  • P305+P351+P338+P337+P313
  • P307+P311
  • P308+P311
  • P310 Immediately call a POISON CENTER or doctor/physician. 立即呼救解毒中心或医生/医师。
  • P362 Take off contaminated clothing and wash before reuse. 脱掉污染的衣服,清洗后方可重新使用
  • P370+P378
  • P403+P233
  • P405 Store locked up. 上锁保管。
  • P501 Dispose of contents/container to..… 处理内容物/容器.....
Signal word Danger
Safety Statements
  • S16 Keep away from sources of ignition - No smoking 远离火源,禁止吸烟;
  • S26 In case of contact with eyes, rinse immediately with plenty of water and seek medical advice 眼睛接触后,立即用大量水冲洗并征求医生意见;
  • S28 After contact with skin, wash immediately with plenty of ... (to be specified by the manufacturer) 皮肤接触后,立即用大量…(由生产厂家指定)冲洗;
  • S29 Do not empty into drains 不要排入下水道;
  • S33 Take precautionary measures against static discharges 对静电采取预防措施;
  • S36/37 Wear suitable protective clothing and gloves 穿戴适当的防护服和手套;
  • S36/37/39 Wear suitable protective clothing, gloves and eye/face protection 穿戴适当的防护服、手套和眼睛/面保护;
  • S45 In case of accident or if you feel unwell seek medical advice immediately (show the label where possible) 发生事故时或感觉不适时,立即求医(可能时出示标签);
  • S60 This material and its container must be disposed of as hazardous waste 该物质及其容器必须作为危险废物处置;
  • S61 Avoid release to the environment. Refer to special instructions/safety data sheet 避免释放到环境中,参考特别指示/安全收据说明书;
  • S62 If swallowed, do not induce vomiting: seek medical advice immediately and show this container or label where possible 吞食后不要催吐:立即求医并出示该容器或标签;
  • S7/9 Keep container tightly closed and in a well-ventilated place 保持容器严格密闭,置于通风良好的场所;
  • S9 Keep container in a well-ventilated place 保持容器在通风良好的场所;
Risk Statements
  • R10 Flammable 易燃
  • R11 Highly flammable 非常易燃
  • R19 May form explosive peroxides 可能生成易爆的过氧化物质
  • R26 Very toxic by inhalation 吸入极毒
  • R36/37/38 Irritating to eyes, respiratory system and skin 对眼睛、呼吸系统和皮肤有刺激性
  • R37/38 Irritating to respiratory system and skin 对呼吸系统和皮肤有刺激性
  • R38 Irritating to skin 刺激皮肤
  • R40 Limited evidence of a carcinogenic effect 有限证据表明其致癌作用
  • R41 Risk of serious damage to eyes 有严重损伤眼睛的危险
  • R43 May cause sensitisation by skin contact 皮肤接触会产生过敏反应
  • R50/53
  • R65 Harmful: may cause lung damage if swallowed 若吞咽可能伤害肺部器官
  • R67 Vapours may cause drowsiness and dizziness 蒸汽可能导致嗜睡和昏厥
Storage condition 2-8°C, stored under nitrogen {LY} 2-8°C, stored under nitrogen Moisture Sensitive Store at room temperature {} {LY} 2-8°C, stored under nitrogen {} {} {LY} 2-8°C, stored under nitrogen {} {} {} {LY} 2-8°C, stored under nitrogen {} {} {} {} {LY} 2-8°C, stored under nitrogen {} {} {} {} {} {LY} 2-8°C, stored under nitrogen {} {} {} {} {} {} {LY} 2-8°C, stored under nitrogen {} {} {} {} {} {} {} {LY} 2-8°C, stored under nitrogen {} {} {} {} {} {} {} {} {LY} 2-8°C, stored under nitrogen {} {} {} {} {} {} {} {} {} {LY} 2-8°C, stored under nitrogen {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C, stored under nitrogen {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C, stored under nitrogen {} {} {} {} {} {} {} {} {} {} {} {} { {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C, stored under nitrogen {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C, stored under nitrogen {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C, stored under ni
UN Number 1992 2929 2930
Packing GroupII
Hazard Class3/6.1

其他信息

  • 遇水分解成叔丁醇和CO2,因此瓶装试剂,在吸潮后会导致瓶内压力升高,包装开启时注意个人防护。

系列性分类