氘代叔丁醇 | 3972-25-6

• 物质功能分类: 化学试剂 - 氘代试剂
• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 氘代叔丁醇
• 英文名称: tert-butanol-OD
• 英文别名: tert-butyl alcohol-d；2-Methylpropan-2-(2H)ol；2-deuteriooxy-2-methylpropane
• CAS: 3972-25-6
• 化学式: C₄H₁₀O
• 分子量: 75.1149
• InChiKey: DKGAVHZHDRPRBM-UICOGKGYSA-N

物化性质

• 熔点：
  23-26 °C (lit.)
• 沸点：
  83 °C (lit.)
• 密度：
  0.786 g/mL at 25 °C
• 闪点：
  52 °F
• 溶解度：
  可溶于丙酮、氯仿（微溶）、甲醇（微溶）
• 稳定性/保质期：
  常温常压下稳定，为一种透明的液体。

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  5
• 可旋转键数：
  0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 危险品标志：
  Xn,F
• 安全说明：
  S16,S9
• 危险类别码：
  R11,R20
• WGK Germany：
  1,3
• 危险品运输编号：
  UN 1120 3/PG 2
• 储存条件：
  请将药品存放在避光、通风且干燥的地方，并密封保存。

SDS

Name:	Tert.-butan(ol-d) 98+ atom % d Material Safety Data Sheet
Synonym:	NoneNon
CAS:	3972-25-6

Section 1 - Chemical Product MSDS Name:Tert.-butan(ol-d) 98+ atom % d Material Safety Data Sheet
Synonym:NoneNon

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
3972-25-6	tert-Butan(ol-d)		223-597-1

Hazard Symbols: XN F
Risk Phrases: 11 20

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Highly flammable. Harmful by inhalation.Hygroscopic (absorbs moisture from the air).
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause mild skin irritation. May cause reddening of the skin.
Ingestion:
May cause irritation of the digestive tract. May cause central nervous system depression, characterized by excitement, followed by headache, dizziness, drowsiness, and nausea. Advanced stages may cause collapse, unconsciousness, coma and possible death due to respiratory failure.
Inhalation:
May cause respiratory tract irritation. May cause narcotic effects in high concentration. May cause drowsiness, unconsciousness, and central nervous system depression.
Chronic:
Chronic inhalation may cause effects similar to those of acute inhalation.

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Section 4 - FIRST AID MEASURES
Eyes: Immediately flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid immediately.
Skin:
Immediately flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes. Get medical aid if irritation develops or persists.
Ingestion:
Call a poison control center. If swallowed, do not induce vomiting unless directed to do so by medical personnel. Never give anything by mouth to an unconscious person. Get medical aid.
Inhalation:
Get medical aid immediately. Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen.
Notes to Physician:

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Section 5 - FIRE FIGHTING MEASURES
General Information:
Containers can build up pressure if exposed to heat and/or fire. As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear. Vapors can travel to a source of ignition and flash back. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion. Flammable Liquid.
Can release vapors that form explosive mixtures at temperatures above the flashpoint. Use water spray to keep fire-exposed containers cool.
Extinguishing Media:
Use foam, dry chemical, or carbon dioxide. Water may be ineffective.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Absorb spill with inert material (e.g. vermiculite, sand or earth), then place in suitable container. Remove all sources of ignition.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Use only in a well-ventilated area.
Ground and bond containers when transferring material. Avoid contact with eyes, skin, and clothing. Empty containers retain product residue, (liquid and/or vapor), and can be dangerous. Keep container tightly closed. Keep away from heat, sparks and flame. Avoid ingestion and inhalation. Do not pressurize, cut, weld, braze, solder, drill, grind, or expose empty containers to heat, sparks or open flames.
Storage:
Keep away from heat, sparks, and flame. Keep away from sources of ignition. Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.
Flammables-area.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Use adequate general or local exhaust ventilation to keep airborne concentrations below the permissible exposure limits.
Exposure Limits CAS# 3972-25-6: Personal Protective Equipment Eyes: Wear appropriate protective eyeglasses or chemical safety goggles as described by OSHA's eye and face protection regulations in 29 CFR 1910.133 or European Standard EN166.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to prevent skin exposure.
Respirators:
Follow the OSHA respirator regulations found in 29 CFR 1910.134 or European Standard EN 149. Use a NIOSH/MSHA or European Standard EN 149 approved respirator if exposure limits are exceeded or if irritation or other symptoms are experienced.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Liquid
Color: clear, colorless
Odor: Not available.
pH: Not available.
Vapor Pressure: 40 mm Hg @24.5
Viscosity: Not available.
Boiling Point: 83 deg C @ 760.00mm Hg
Freezing/Melting Point: Not available.
Autoignition Temperature: Not available.
Flash Point: 11 deg C ( 51.80 deg F)
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water: soluble in water
Specific Gravity/Density:
Molecular Formula: C4H9DO
Molecular Weight: 75.13

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
High temperatures, incompatible materials, ignition sources, moisture.
Incompatibilities with Other Materials:
Aluminum, chromium trioxide, organic peroxides, strong oxidizers, potassium-sodium alloys. For specific details, please refer to the NFPA Fire Protection Guide for the specific details.
Hazardous Decomposition Products:
Carbon monoxide, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 3972-25-6 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
tert-Butan(ol-d) - Not listed by ACGIH, IARC, or NTP.

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Section 12 - ECOLOGICAL INFORMATION

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Section 13 - DISPOSAL CONSIDERATIONS
Dispose of in a manner consistent with federal, state, and local regulations.

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Section 14 - TRANSPORT INFORMATION

IATA
Shipping Name: BUTANOLS
Hazard Class: 3
UN Number: 1120
Packing Group: II
IMO
Shipping Name: BUTANOLS
Hazard Class: 3.2
UN Number: 1120
Packing Group: II
RID/ADR
Shipping Name: BUTANOLS
Hazard Class: 3
UN Number: 1120
Packing group: II

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: XN F
Risk Phrases:
R 11 Highly flammable.
R 20 Harmful by inhalation.
Safety Phrases:
S 9 Keep container in a well-ventilated place.
S 16 Keep away from sources of ignition - No
smoking.
WGK (Water Danger/Protection)
CAS# 3972-25-6: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 3972-25-6 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 3972-25-6 is not listed on the TSCA inventory.
It is for research and development use only.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

概述

近年来，氘代药物的应用前景逐渐受到各国科研人员的广泛关注，这种复兴主要源于人们对其合成的兴趣。氘代分子不仅能够用于研究药物和化学反应的代谢机理，还在功能材料和质谱分析中作为基准物发挥作用。氘代叔丁醇是通过将叔丁醇中的氢原子替换为氘原子得到的。

制备

氘代叔丁醇可应用于有机合成中，例如制备α, α-二氘代醇类化合物。具体操作如下：在带有单个开口的瓶中进行氮气保护，加入0.50毫摩尔的化合物1d、2.5毫升四氢呋喃和2.50毫摩尔的氘代叔丁醇(t-BuOD)，以及0.225毫摩尔的钠块。在0℃下搅拌5分钟后升温至室温，使用3.0M盐酸水溶液进行猝灭反应。随后加入乙醚与饱和食盐水进行萃取，并对有机相进行干燥和浓缩处理。通过柱层析分离得到37.3毫克目标化合物，总收率为54%。

反应信息

• 作为反应物：
  描述：

  氘代叔丁醇 在 重水 作用下， 以 水 为溶剂， 生成 叔丁醇
  参考文献：
  名称：

  A new method for obtaining isotopic fractionation data at multiple sites in rapidly exchanging systems

  摘要：

  DOI：

  10.1021/ja00295a017
• 作为产物：
  描述：

  叔丁基过氧化氢 在 苯甲醛-α-d1 、 4,4'-二溴-2,2'-联吡啶 、 copper(l) chloride 作用下， 以 乙腈 为溶剂， 反应 24.0h， 生成 氘代叔丁醇
  参考文献：
  名称：

  铜通过分子内自由基级联酰基氰化反应合成含CN的苯并二氢吡喃-4-酮

  摘要：

  已经开发了铜催化的分子内自由基级联酰基氰化以合成含氰基的chroman-4-ones。使用绿色氰基源，在温和的条件下，可以中等到良好的产率制备一系列CN取代的chroman-4-one衍生物。对照实验表明该反应涉及分子内酰基自由基加成/氰化过程。此外，该协议具有步长和原子经济性，将氰基引入到chroman-4-one中引起了极大的兴趣和重要性。

  DOI：

  10.1016/j.tetlet.2021.153061
• 作为试剂：
  描述：

  甲基萘 在 氘代叔丁醇 作用下， 以 异丙醇 、 叔丁醇 为溶剂， 反应 7.0h， 生成
  参考文献：
  名称：

  McCullough, John J.; McMurry, T. Brian; Work, D. Neil, Journal of the Chemical Society. Perkin transactions I, 1991, # 2, p. 461 - 464

  摘要：

  DOI：

文献信息

• A terminal nickel(ii) anilide complex featuring an unsymmetrically substituted amido pincer ligand: synthesis and reactivity
  作者：Lan-Chang Liang、Chun-Wei Li、Pei-Ying Lee、Chih-Hsiang Chang、Hon Man Lee

  DOI：10.1039/c1dt10191a

  日期：——

  This work describes preparation and reaction chemistry of a terminal nickel(II) anilide complex supported by an unsymmetrically substituted diarylamido diphosphine ligand, [N(o-C6H4PPh2)(o-C6H4PiPr2)]− ([Ph-PNP-iPr]−). Treatment of NiCl2(DME) with H[Ph-PNP-iPr] in THF at room temperature produced [Ph-PNP-iPr]NiCl as green crystals in 82% yield. Salt metathesis of [Ph-PNP-iPr]NiCl with LiNHPh(THF) in

  这项工作描述了由不对称取代的二芳基酰胺二膦配体[N（o -C 6 H 4 PPh 2）（o -C 6 H 4 P i Pr 2）]支撑的末端镍（II）苯胺配合物的制备和反应化学。-（[Ph-PNP- i Pr] -）。在室温下用H [Ph-PNP- i Pr]在THF中处理NiCl 2（DME），生成[Ph-PNP- i Pr] NiCl为绿色晶体，产率为82％。[Ph-PNP- i的盐易位[-PNP - Pr] NiNHPh呈绿色蓝色固体，在-35°C的条件下，用LiNHPh（THF）在THF中的Pr] NiCl生成。苯胺复合物使质子（例如PhOH和PhSH）和非质子（例如，三甲基甲硅烷基乙炔， 苯乙炔， 和 乙腈）中的酸 苯在室温下定量得到[Ph-PNP- i Pr] NiX（X = OPh，SPh，C CSiMe 3，C CPh，CH 2 CN）。此外，[Ph-PNP- i Pr]
• [EN] PROTEIN TYROSINE PHOSPHATASE INHIBITORS AND METHODS OF USE THEREOF<br/>[FR] INHIBITEURS DE PROTÉINE TYROSINE PHOSPHATASE ET LEURS MÉTHODES D'UTILISATION
  申请人：CALICO LIFE SCIENCES LLC

  公开号：WO2021127499A1

  公开（公告）日：2021-06-24

  Provided herein are compounds, compositions, and methods useful for inhibiting protein tyrosine phosphatase, e.g, protein tyrosine phosphatase non-receptor type 2 (PTPN2) and/or protein tyrosine phosphatase non-receptor type 1 (PTPN1), and for treating related diseases, disorders and conditions favorably responsive to PTPN1 or PTPN2 inhibitor treatment, e.g, a cancer or a metabolic disease.

  本文提供了用于抑制蛋白酪氨酸磷酸酶的化合物、组合物和方法，例如蛋白酪氨酸磷酸酶非受体型2（PTPN2）和/或蛋白酪氨酸磷酸酶非受体型1（PTPN1），以及用于治疗对PTPN1或PTPN2抑制剂治疗有良好反应的相关疾病、紊乱和状况的方法，例如癌症或代谢性疾病。
• Coupling Reaction of a Cyclopentadienyl Ligand with a Dienyl or Alkenyl Moiety on Titanocene
  作者：Zhiyi Song、Yi-Fang Hsieh、Ken-ichiro Kanno、Kiyohiko Nakajima、Tamotsu Takahashi

  DOI：10.1021/om101020u

  日期：2011.2.28

  Coupling reactions of a cyclopentadienyl (Cp) ligand with a dienyl or alkenyl ligand on dienyl- or alkenyltitanocenes proceeded to give dienylcyclopentadiene or alkenylcyclopentadiene derivatives in good to high yields. Dienyltitanocene derivatives were prepared by protonation of bis(cyclopentadienyl)titanacyclopentadienes with carboxylic acids. Chlorodienyltitanocene derivatives were formed by the

  环戊二烯基（Cp）配体与二烯​​基或烯基噻吩并茂上的二烯基或烯基配体的偶联反应以高收率或高收率得到二烯基环戊二烯或烯基环戊二烯衍生物。通过用羧酸使双（环戊二烯基）噻吩基环戊二烯质子化来制备二烯基噻吩衍生物。通过二氧杂环戊二烯与NCS的反应形成了氯二烯基钛茂新衍生物。通过由Cp 2 TiEt 2和炔烃制备的二茂钛环戊烯与t-BuOH。通过对单晶的X射线分析来确定烯基噻吨并茂（在1，2-二苯基乙烯基的情况下）的结构。将这些二烯基，氯二烯基或烯基噻吩并茂在50°C下用偶氮苯处理6 h，并以高收率或高收率获得了相应的二烯基环戊二烯，氯二烯基环戊二烯和烯基环戊二烯衍生物。该结果支持Cp配体与钛环戊二烯的二烯部分偶联反应的逐步机理的存在，在偶氮苯存在下得到茚衍生物。
• Pd‐Catalyzed Selective Carbonylation of <i>gem</i> ‐Difluoroalkenes: A Practical Synthesis of Difluoromethylated Esters
  作者：Jiawang Liu、Ji Yang、Francesco Ferretti、Ralf Jackstell、Matthias Beller

  DOI：10.1002/anie.201813801

  日期：2019.3.26

  described. This novel catalytic transformation proceeds in the presence of Pd(acac)2/1,2‐bis((di‐tert‐butylphosphan‐yl)methyl)benzene (btbpx) (L4) and allows for an efficient and straightforward access to a range of difluoromethylated esters in high yields and regioselectivities. The synthetic utility of the protocol is showcased in the practical synthesis of a Cyclandelate analogue using this methodology

  描述了宝石二氟烯烃烷氧基羰基化的第一种催化剂。在Pd（acac）2 / 1,2-双（（二叔丁基膦基）甲基）苯（btbpx）（L4）的存在下进行这种新颖的催化转化过程，可以有效而直接地获得一系列二氟甲基化酯的高收率和区域选择性。使用该方法学作为关键步骤，在环戊酸酯类似物的实际合成中展示了该协议的综合用途。
• Photocatalytic Reductive Radical‐Polar Crossover for a Base‐Free Corey–Seebach Reaction
  作者：Karsten Donabauer、Kathiravan Murugesan、Urša Rozman、Stefano Crespi、Burkhard König

  DOI：10.1002/chem.202003000

  日期：2020.10.9

  abstraction of a hydrogen atom followed by radical reduction. The generated nucleophilic intermediate is then capable of adding to carbonyl electrophiles. The obtained dithiane can be easily converted to the valuable α‐hydroxy carbonyl in a subsequent step. The proposed reaction mechanism is supported by emission quenching, radical–radical homocoupling and deuterium labeling studies as well as by calculated

  在有机合成中，无金属的碳负离子亲核体的产生至关重要。本文中，我们报告了一种对Corey–Seebach反应的光催化方法。提出的方法在温和的氧化还原中性和无碱条件下运行，从而提供具有高官能团耐受性的所需产品。通过光和氢原子转移（HAT）催化的组合可以实现反应。这种催化合并使CH可以通过夺取氢原子然后进行自由基还原来进行碳负离子活化。然后，所产生的亲核中间体能够加成至羰基亲电子体。在随后的步骤中，可以很容易地将获得的二噻吩转化为有价值的α-羟基羰基。所提出的反应机理得到了发射猝灭的支持，