Tert-Butyldimethylchlorosilane 叔丁基二甲基氯硅烷

CAS 18162-48-6 MFCD00000501

化学结构图

18162-48-6
SMILES: CC(C)(C)[Si](C)(C)Cl

化学属性

Mol. FormulaC6H15ClSi
Mol. Weight150.72
Melting Point86-88 °C
Refractive indexn20/D 1.46
Boiling Point113 °C at 760 mmHg
Density0.87
Flash Point22°C
TSCAYes
Stability对湿度敏感
Appearance 白色固体。熔点86-89℃，沸点128℃。能与水、乙醇、有机酸或胺类缓慢反应。
pH:A

别名和识别编码

Chemical NameTert-Butyldimethylchlorosilane
CAS Number18162-48-6
Synonym Silane, chloro-tert-butyldimethyl- {LY} Silane, chloro-tert-butyldimethyl- {} {LY} Silane, chloro-tert-butyldimethyl- {} {} {LY} Silane, chloro-tert-butyldimethyl- {} {} {} {LY} Silane, chloro-tert-butyldimethyl- {} {} {} {} {LY} Silane, chloro-tert-butyldimethyl- {} {} {} {} {} {LY} Silane, chloro-tert-butyldimethyl- {} {} {} {} {} {} {LY} Silane, chloro-tert-butyldimethyl- {} {} {} {} {} {} {} {LY} Silane, chloro-tert-butyldimethyl- {} {} {} {} {} {} {} {} {LY} Silane, chloro-tert-butyldimethyl- {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Silane, chloro-tert-butyldimethyl- {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Silane, chloro-tert-butyldimethyl- {} {} {} {} {} {} {} {} {} {} {} {LY} Silane, chloro-tert-butyldimethyl- {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Silane, chloro-tert-butyldimethyl- {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Silane, ch
PubChem Substance ID24870907
EC Number242-042-4
Beilstein Registry Number505999
MDL NumberMFCD00000501
Chemical Name Translation叔丁基二甲基氯硅烷
Reaxys-RN505999
Wiswesser Line NotationG-SI-1&1&X1&1&1
LabNetwork Molecule IDLN00163233
Canonical SMILESC[Si](C(C)(C)C)(Cl)C
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分类

  • {SNA} Chemical Synthesis, Protecting and Derivatizing Reagents, Protection and Derivatization, Silicon-Based, Synthetic Reagents
  • {uni_hamburg} no charge; 1fragment
  • Miscellaneous Reagents

产品应用

  • 硅烷化剂。有机合成中作为羟基保护剂,衍生化试剂用于分析和制备。保护叔醇类。与醇类反应形成硅醚。测定胆固醇衍生物的构象。合成前列腺素，某些抗生素、降血脂药洛弗斯汀(Lovastatin)和新弗斯汀(Simvastatin)的辅助原料。

相关文献及参考

  • Reagent for silylation of hydroxyl functions (see Appendix 4), giving silyl ethers more stable to aqueous
  • Short: II/25D
  • Merck: 14,10401
  • Many other reagents have been used, including:
  • Shen, H., et al.: J. Med. Chem., 53, 2666 (2010),
  • Cleavage is generally effected with fluoride ion e.g. TBAF in an aprotic system: J. Am. Chem. Soc., 94, 6190 (1972), or KF with a phase-transfer catalyst: J. Am. Chem. Soc., 90, 4462, 4464 (1968); 96, 2250 (1974); J. Chem. Soc., Chem. Commun., 514 (1979).
  • Qiang, L., et al.: Bioorg. Med. Chem. Lett., 20, 836 (2010),
  • Short: EINECS
  • Imidazole in DMF: J. Am. Chem. Soc., 94, 6190 (1972); Et3N - DMAP: Tetrahedron Lett., 99 (1979); Org. Synth. Coll., 9, 136 (1998); N-ethyldiisopropylamine: Tetrahedron Lett., 25, 227 (1984); 1,1,3,3-tetramethylguanidine: J. Org. Chem., 49, 4657 (1984); K2CO3 (phase-transfer): Synth. Commun., 11, 545 (1981); DBU - superior to imidazole for thiols, amines and carboxylic acids: Tetrahedron Lett., 26, 475 (1985).
  • Reagent for silylation of hydroxyl functions (see Appendix 4), giving silyl ethers more stable to aqueous hydrolysis e.g. during work-up, than TMS. Various conditions have been used for the introduction of the group:
  • Acidic ion-exchange resin: Tetrahedron Lett., 21, 137 (1980); NBS in DMSO: Synthesis, 234 (1980); BF3 etherate: Synth. Commun., 9, 295 (1979); FeCl3 or SnCl2 in acetonitrile: Synth. Commun., 20, 757 (1990); K 10 clay in aqueous methanol: J. Org. Chem. 61, 9026 (1996); DMSO-water at 90o; many other groups unaffected: Tetrahedron Lett., 38, 495 (1997). See also Pyridinium p-toluenesulfonate, A15708, and Triethyl­amine trihydrofluoride, L14417.
  • Merck: 14,10401 Beilstein: 4,IV,4076

安全信息

GHS Symbol
WGK Germany2
Hazard statements
  • H314 Causes severe skin burns and eye damage 导致严重的皮肤灼伤和眼睛损伤
  • H351 Suspected of causing cancer 怀疑致癌
  • H225 Highly flammable liquid and vapour 高度易燃液体和蒸气
  • H335 May cause respiratory irritation 可能导致呼吸道刺激
  • H228 Flammable solid 易燃固体
  • H302 Harmful if swallowed 吞食有害
  • H226 Flammable liquid and vapour 易燃液体和蒸气
  • H304 May be fatal if swallowed and enters airways 吞食和进入呼吸道可能致命
  • H336 May cause drowsiness or dizziness 肯能导致嗜睡或头晕
  • H361d Suspected of damaging the unborn child 怀疑对未出生婴儿造成伤害
  • 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 Faceshields, full-face respirator (US), Gloves, Goggles, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
RTECSVV2000000
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。
  • 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。
  • 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。
  • 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。
  • P305+P351+P338
  • P305+P351+P338+P310
  • P310 Immediately call a POISON CENTER or doctor/physician. 立即呼救解毒中心或医生/医师。
  • P370+P378
  • 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；
  • S25 Avoid contact with eyes 避免眼睛接触；
  • 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；
  • S27 Take off immediately all contaminated clothing 立即脱掉全部污染的衣服；
  • 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；
  • S36/37/39 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）；
  • S46 If swallowed, seek medical advice immediately and show this container or label 食入时，立即求医并出示容器/标签；
  • S53 Avoid exposure - obtain special instructions before use 避免接触，使用前获得特别指示说明；
  • 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；
Packing GroupII
UN Number 2925 UN2924
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
  • R20/21/22 Harmful by inhalation, in contact with skin and if swallowed 吸入、皮肤接触和不慎吞咽有害
  • R22 Harmful if swallowed 吞咽有害
  • R34 Causes burns 会导致灼伤
  • R35 Causes severe burns 会导致严重灼伤
  • 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 Irritating to respiratory system 刺激呼吸道
  • R40 Limited evidence of a carcinogenic effect 有限证据表明其致癌作用
  • R45 May cause cancer 可能致癌
  • R48/20
  • R63 Possible risk of harm to the unborn child 可能危害未出生婴儿
  • 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 -20°C {LY} -20°C Moisture Sensitive Store at 5°C {} {LY} -20°C {} {} {LY} -20°C {} {} {} {LY} -20°C {} {} {} {} {LY} -20°C {} {} {} {} {} {LY} -20°C {} {} {} {} {} {} {LY} -20°C {} {} {} {} {} {} {} {LY} -20°C {} {} {} {} {} {} {} {} {LY} -20°C {} {} {} {} {} {} {} {} {} {LY} -20°C {} {} {} {} {} {} {} {} {} {} {LY} -20°C {} {} {} {} {} {} {} {} {} {} {} {LY} -20°C {} {} {} {} {} {} {} {} {} {} {} {} {LY} -20°C {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} -20°C {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} -20°C {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} -20°C {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} -20°C {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} -20°C {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} -20°C {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} -20°C {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} { {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {
Hazard Codes 4.1 F,C
Hazard Class4.1/8 
TYPE OF TEST            : LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE       : Intraperitoneal
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : 1 gm/kg
TOXIC EFFECTS :
   Immunological Including Allergic - decreased immune response
REFERENCE :
   StoGD# Personal Communication from G.D. Stoner, Dept. of Community Medicine,
   School of Medicine, Univ. of California, La Jolla, CA 92037, May 25, 1975 
   Volume(issue)/page/year: 27MAY1975

其他信息

  • 海关编码:29310095
  • Alfa Aesar:叔丁基二甲基氯硅烷,97% tert-Butyldimethylchlorosilane, 97%(18162-48-6)
  • 叔丁基二甲基氯硅烷价格(试剂级):更新日期 产品编号 产品名称 包装 价格 2011/08/23 xw020067 叔丁基二甲基氯硅烷 500g 798元 2011/08/23 xw020058 叔丁基二甲基氯硅烷（2-8℃） 100g 298元 2011/04/16 B0995 叔丁基二甲基氯硅烷[叔丁基二甲基硅化剂] tert-Butyldimethylchlorosilane [tert-Butyldimethylsilylating Agent] 100G 2040元
  • 图谱信息:叔丁基二甲基氯硅烷(18162-48-6)红外图谱(IR1)
  • 检测方法:GC,NMR
  • TCI Shanghai:叔丁基二甲基氯硅烷[叔丁基二甲基硅化剂] tert-Butyldimethylchlorosilane [tert-Butyldimethylsilylating Agent],>;98.0%(GC)(18162-48-6)
  • Hazard Note:Flammable/Corrosive/Moisture Sensitive
  • 下游产品:5-(氨甲基)-1-甲基吡咯烷-2-酮 --> 4-乙酰氧基氮杂环丁酮 --> 杂氮双环磷酸酯 --> 2-氰基吡啶-4-醛 --> 4-羟甲基吡啶-2-腈 --> 辛伐他汀 --> 2-氯-4-硝基苯-alpha-L-岩藻糖苷 --> 4-巯基苯硼酸 --> 孟鲁司特 --> 叔丁基二甲硅基三氟甲磺酸酯 --> 卡泊三醇
  • Acros Organics:叔丁基二甲基氯硅烷 tert-Butylchlorodimethylsilane, 98%(18162-48-6)
  • 对湿敏感。易燃。有腐蚀性。和水反应，溶于醚和烃，和醇、有机酸和胺反应
  • 用途三:硅烷化剂。有机合成中作为羟基保护剂,衍生化试剂用于分析和制备。保护叔醇类。与醇类反应形成硅醚。测定胆固醇衍生物的构象。合成前列腺素，某些抗生素、降血脂药洛弗斯汀(Lovastatin)和新弗斯汀(Simvastatin)的辅助原料。
  • F:10-21
  • 对湿敏感。易燃。有腐蚀性。和水反应，溶于醚和烃，和醇、有机酸和胺反应。
  • 上游原料:正戊烷 --> 叔丁基锂 --> 二氯二甲基硅烷
  • TSCA:Yes
  • 方法一:将二氯二甲基硅烷的戊烷溶液冷却至0℃，在氮气和搅拌下滴加叔丁基锂的戊烷溶液。维持0℃，搅拌反应1.5h后升温至25℃，继续反应48h。蒸馏，收集125℃（97.5kPa）馏分，静置固化，得叔丁基二甲基氯硅烷。产率70%。
  • MOL 文件:18162-48-6.mol
  • 用途一:用于合成前列腺素，某些抗生素，降血脂药洛伐他汀和辛伐他汀的辅助原料
  • MSDS 信息:TBDMCS(18162-48-6).msds
  • 存储注意事项:湿度敏感
  • 敏感性:Moisture Sensitive
  • 用途二:用作医药中间体及用于有机合成，在有机合成中作为羟基保护剂
  • Sigma Aldrich:18162-48-6(sigmaaldrich)

系列性分类

  1. Chemical Synthesis 化学合成
  2. Organometallic Reagents 金属有机试剂
  3. Organosilicon 有机硅
  1. Chemical Synthesis 化学合成
  2. Organometallic Reagents 金属有机试剂
  3. Organosilicon 有机硅
  1. Chemical Synthesis 化学合成
  2. Organometallic Reagents 金属有机试剂
  3. Organosilicon 有机硅
  1. Chemical Synthesis 化学合成
  2. Organometallic Reagents 金属有机试剂
  3. Organosilicon 有机硅
  1. Chemical Synthesis 化学合成
  2. Synthetic Reagents 合成试剂
  3. Protection and Derivatization - Synthetic Reagents
  1. Chemical Synthesis 化学合成
  2. Synthetic Reagents 合成试剂
  3. Protection and Derivatization - Synthetic Reagents
  4. Protecting and Derivatizing Reagents - Protection and Derivatization
  1. Analytical & Chromatography 分析化学与色谱
  2. Analytical Standards
  3. Alphabetic - Analytical Standards
  4. D - Alphabetic
  5. DID - DIN - D
  1. Chemical Synthesis 化学合成
  2. Synthetic Reagents 合成试剂
  3. Protection and Derivatization - Synthetic Reagents
  4. Protecting and Derivatizing Reagents - Protection and Derivatization
  5. Silicon-Based - Protecting and Derivatizing Reagents
  1. Chemical Synthesis 化学合成
  2. Organometallic Reagents 金属有机试剂
  3. Organosilicon 有机硅
  4. Silanes 硅烷
  1. Chemical Synthesis 化学合成
  2. Synthetic Reagents 合成试剂
  3. Silicon Compounds for Organic Synthesis 硅化合物
  1. Analytical & Chromatography 分析化学与色谱
  2. GC Derivatizing Reagents
  1. Life Science 生命科学
  2. Biochemistry / Glyco-Chemistry
  3. DNA / RNA Synthesis
  1. Medical Research Areas
  2. Ubiquitin
  3. Treprostinil