苯酚-2,3,4,5,6-d5 | 4165-62-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 中文名称: 苯酚-2,3,4,5,6-d5
• 中文别名: 氘代苯酚；酚-d5；五氘代苯酚
• 英文名称: phenol-d5
• 英文别名: d5-phenol；phenol-2,3,4,5,6-d₅；[²H₅]-phenol；2,3,4,5,6-pentadeuteriophenol
• CAS: 4165-62-2
• 化学式: C₆H₆O
• 分子量: 99.0733
• InChiKey: ISWSIDIOOBJBQZ-RALIUCGRSA-N

物化性质

• 熔点：
  40-42 °C(lit.)
• 沸点：
  182 °C(lit.)
• 密度：
  1.127 g/mL at 25 °C
• 闪点：
  175 °F
• 溶解度：
  可溶于乙腈（少量）、氯仿（少量）、乙酸乙酯（少量）、甲烷
• 稳定性/保质期：

  常温常压下稳定，避免与强氧化剂、强碱和强酸接触。

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  7
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 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：
  T,C
• 安全说明：
  S24/25,S26,S28,S36,S37,S39,S45
• 危险类别码：
  R23/24/25
• WGK Germany：
  3
• 危险品运输编号：
  UN 1671 6.1/PG 2
• 储存条件：
  密闭、阴凉干燥处保存，并在容器中充入氮气。

SDS

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SECTION 1: Identification of the substance/mixture and of the company/undertaking
Product identifiers
Product name : Phenol-2,3,4,5,6-d5
REACH No. : A registration number is not available for this substance as the substance
or its uses are exempted from registration, the annual tonnage does not
require a registration or the registration is envisaged for a later
registration deadline.
CAS-No. : 4165-62-2
Relevant identified uses of the substance or mixture and uses advised against
Identified uses : Laboratory chemicals, Manufacture of substances

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SECTION 2: Hazards identification
Classification of the substance or mixture
Classification according to Regulation (EC) No 1272/2008
Germ cell mutagenicity (Category 2), H341
Acute toxicity, Inhalation (Category 3), H331
Acute toxicity, Dermal (Category 3), H311
Acute toxicity, Oral (Category 3), H301
Specific target organ toxicity - repeated exposure (Category 2), H373
Skin corrosion (Category 1B), H314
For the full text of the H-Statements mentioned in this Section, see Section 16.
Classification according to EU Directives 67/548/EEC or 1999/45/EC
R68
T Toxic R23/24/25
C Corrosive R34
Xn Harmful R48/20/21/22
For the full text of the R-phrases mentioned in this Section, see Section 16.
Label elements
Labelling according Regulation (EC) No 1272/2008
Pictogram
Signal word Danger
Hazard statement(s)
H301 Toxic if swallowed.
H311 Toxic in contact with skin.
H314 Causes severe skin burns and eye damage.
H331 Toxic if inhaled.
H341 Suspected of causing genetic defects.
H373 May cause damage to organs through prolonged or repeated exposure.
Precautionary statement(s)
P261 Avoid breathing dust/ fume/ gas/ mist/ vapours/ spray.
P280 Wear protective gloves/ protective clothing/ eye protection/ face
protection.
P301 + P310 IF SWALLOWED: Immediately call a POISON CENTER or doctor/
physician.
P305 + P351 + P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove
contact lenses, if present and easy to do. Continue rinsing.
P310 Immediately call a POISON CENTER or doctor/ physician.
Supplemental Hazard none
Statements
Other hazards - none

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SECTION 3: Composition/information on ingredients
Substances
Chemical characterization : Natural product
Formula : C6D5HO
Molecular Weight : 99,14 g/mol
CAS-No. : 4165-62-2
Hazardous ingredients according to Regulation (EC) No 1272/2008
Component Classification Concentration
Phenol-2,3,4,5,6-d5
CAS-No. 4165-62-2 Acute Tox. 3; Skin Corr. 1B; <= 100 %
Index-No. 604-001-00-2 Muta. 2; STOT RE 2; H301 +
H311 + H331, H314, H341,
H373
Hazardous ingredients according to Directive 1999/45/EC
Component Classification Concentration
Phenol-2,3,4,5,6-d5
CAS-No. 4165-62-2 T, Mut.Cat.3, R23/24/25 - R34 <= 100 %
Index-No. 604-001-00-2 - R48/20/21/22 - R68
For the full text of the H-Statements and R-Phrases mentioned in this Section, see Section 16

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SECTION 4: First aid measures
Description of first aid measures
General advice
Consult a physician. Show this safety data sheet to the doctor in attendance.
If inhaled
If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician.
In case of skin contact
Take off contaminated clothing and shoes immediately. Wash off with soap and plenty of water. Take
victim immediately to hospital. Consult a physician.
In case of eye contact
Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician.
If swallowed
Do NOT induce vomiting. Never give anything by mouth to an unconscious person. Rinse mouth with
water. Consult a physician.
Most important symptoms and effects, both acute and delayed
The most important known symptoms and effects are described in the labelling (see section 2.2) and/or in
section 11
Indication of any immediate medical attention and special treatment needed
no data available

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SECTION 5: Firefighting measures
Extinguishing media
Suitable extinguishing media
Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.
Special hazards arising from the substance or mixture
Carbon oxides
Advice for firefighters
Wear self contained breathing apparatus for fire fighting if necessary.
Further information
no data available

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SECTION 6: Accidental release measures
Personal precautions, protective equipment and emergency procedures
Wear respiratory protection. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure
adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust.
For personal protection see section 8.
Environmental precautions
Prevent further leakage or spillage if safe to do so. Do not let product enter drains.
Methods and materials for containment and cleaning up
Pick up and arrange disposal without creating dust. Sweep up and shovel. Keep in suitable, closed
containers for disposal.
Reference to other sections
For disposal see section 13.

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SECTION 7: Handling and storage
Precautions for safe handling
Avoid contact with skin and eyes. Avoid formation of dust and aerosols.
Provide appropriate exhaust ventilation at places where dust is formed.
For precautions see section 2.2.
Conditions for safe storage, including any incompatibilities
Store in cool place. Keep container tightly closed in a dry and well-ventilated place.
Store under inert gas. hygroscopic
Specific end use(s)
A part from the uses mentioned in section 1.2 no other specific uses are stipulated

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SECTION 8: Exposure controls/personal protection
Control parameters
Components with workplace control parameters
Exposure controls
Appropriate engineering controls
Avoid contact with skin, eyes and clothing. Wash hands before breaks and immediately after handling
the product.
Personal protective equipment
Eye/face protection
Face shield and safety glasses Use equipment for eye protection tested and approved under
appropriate government standards such as NIOSH (US) or EN 166(EU).
Skin protection
Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique
(without touching glove's outer surface) to avoid skin contact with this product. Dispose of
contaminated gloves after use in accordance with applicable laws and good laboratory practices.
Wash and dry hands.
The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and
the standard EN 374 derived from it.
Full contact
Material: butyl-rubber
Minimum layer thickness: 0,3 mm
Break through time: 480 min
Material tested:Butoject® (KCL 897 / Z677647, Size M)
Splash contact
Material: Nitrile rubber
Minimum layer thickness: 0,2 mm
Break through time: 30 min
Material tested:Dermatril® P (KCL 743 / Z677388, Size M)
data source: KCL GmbH, D-36124 Eichenzell, phone [phone], test method: EN374
If used in solution, or mixed with other substances, and under conditions which differ from EN 374,
contact the supplier of the CE approved gloves. This recommendation is advisory only and must
be evaluated by an industrial hygienist and safety officer familiar with the specific situation of
anticipated use by our customers. It should not be construed as offering an approval for any
specific use scenario.
Body Protection
Complete suit protecting against chemicals, The type of protective equipment must be selected
according to the concentration and amount of the dangerous substance at the specific workplace.
Respiratory protection
Where risk assessment shows air-purifying respirators are appropriate use a full-face particle
respirator type N100 (US) or type P3 (EN 143) respirator cartridges as a backup to engineering
controls. If the respirator is the sole means of protection, use a full-face supplied air respirator. Use
respirators and components tested and approved under appropriate government standards such
as NIOSH (US) or CEN (EU).
Control of environmental exposure
Prevent further leakage or spillage if safe to do so. Do not let product enter drains.

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SECTION 9: Physical and chemical properties
Information on basic physical and chemical properties
a) Appearance Form: solid
b) Odour no data available
c) Odour Threshold no data available
d) pH no data available
e) Melting point/freezing Melting point/range: 40 - 42 °C
point Melting point/range: 40 - 42 °C - lit.
f) Initial boiling point and 182 °C
boiling range 182 °C - lit.
g) Flash point 79 °C - closed cup
h) Evapouration rate no data available
i) Flammability (solid, gas) no data available
j) Upper/lower no data available
flammability or
explosive limits
k) Vapour pressure no data available
l) Vapour density no data available
m) Relative density 1,127 g/mL at 25 °C1,127 g/cm3 at 25 °C
n) Water solubility no data available
o) Partition coefficient: n- no data available
octanol/water
p) Auto-ignition no data available
temperature
q) Decomposition no data available
temperature
r) Viscosity no data available
s) Explosive properties no data available
t) Oxidizing properties no data available
Other safety information
no data available

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SECTION 10: Stability and reactivity
Reactivity
no data available
Chemical stability
Stable under recommended storage conditions.
Possibility of hazardous reactions
no data available
Conditions to avoid
no data available
Incompatible materials
no data available
Hazardous decomposition products
Other decomposition products - no data available
In the event of fire: see section 5

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SECTION 11: Toxicological information
Information on toxicological effects
Acute toxicity
no data available
Skin corrosion/irritation
no data available
Serious eye damage/eye irritation
Respiratory or skin sensitisation
no data available
Germ cell mutagenicity
In vitro tests showed mutagenic effects
Carcinogenicity
IARC: 3 - Group 3: Not classifiable as to its carcinogenicity to humans (Phenol-2,3,4,5,6-d5)
Reproductive toxicity
Specific target organ toxicity - single exposure
no data available
Specific target organ toxicity - repeated exposure
May cause damage to organs through prolonged or repeated exposure.
Aspiration hazard
no data available
Additional Information
RTECS: Not available
Material is extremely destructive to tissue of the mucous membranes and upper respiratory tract, eyes, and
skin., spasm, inflammation and edema of the larynx, spasm, inflammation and edema of the bronchi,
pneumonitis, pulmonary edema, burning sensation, Cough, wheezing, laryngitis, Shortness of breath,
Headache, Nausea, Vomiting, Circulatory collapse, tachypnea, paralysis, Convulsions, Coma., necrosis of
mouth and G.I. Tract, Jaundice, respiratory failure, cardiac arrest

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SECTION 12: Ecological information
Toxicity
no data available
Persistence and degradability
no data available
Bioaccumulative potential
no data available
Mobility in soil
no data available
Results of PBT and vPvB assessment
PBT/vPvB assessment not available as chemical safety assessment not required/not conducted
Other adverse effects
no data available

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SECTION 13: Disposal considerations
Waste treatment methods
Product
Offer surplus and non-recyclable solutions to a licensed disposal company. Dissolve or mix the material
with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber.
Contaminated packaging
Dispose of as unused product.

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SECTION 14: Transport information
UN number
ADR/RID: 1671 IMDG: 1671 IATA: 1671
UN proper shipping name
ADR/RID: PHENOL, SOLID
IMDG: PHENOL, SOLID
IATA: Phenol, solid
Transport hazard class(es)
ADR/RID: 6.1 IMDG: 6.1 IATA: 6.1
Packaging group
ADR/RID: II IMDG: II IATA: II
Environmental hazards
ADR/RID: no IMDG Marine pollutant: no IATA: no
Special precautions for user
no data available

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SECTION 15 - REGULATORY INFORMATION
N/A

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  苯酚-2,3,4,5,6-d5 在 咪唑 、 盐酸 、 正丁基锂 、 溴 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 对羟基苯甲醛-D4
  参考文献：
  名称：

  Deuterated Matrix-Assisted Laser Desorption Ionization Matrix Uncovers Masked Mass Spectrometry Imaging Signals of Small Molecules

  摘要：

  D4-α-Cyano-4-hydroxycinnamic acid（D4-CHCA）已被合成为基质，用于小分子药物和内源性化合物的基质辅助激光解吸电离质谱（MALDI-MS）和 MALDI-MS 成像（MSI）。小分子 MALDI-MS 分析历来受到基质离子群和碎片峰的干扰，这些干扰掩盖了低分子量相关化合物的信号。通过使用 D4-CHCA，CHCA（最常用于分析小分子的基质）的离子簇和碎片峰会发生 + 4、+ 8 和 + 12 Da 的偏移，从而暴露出之前被掩盖的低质量范围内的信号。在这里，一种合成小分子药物、一种天然存在的异喹啉生物碱以及包括神经递质乙酰胆碱在内的内源性化合物的模糊 MALDI-MS 信号被揭示出来，并直接从生物组织切片中成像。

  DOI：

  10.1021/ac301498m
• 作为产物：
  描述：

  氘代苯 在 双氧水 、 三氟乙酸 作用下， 以 水 、 乙腈 为溶剂， 反应 1.0h， 生成 苯酚-2,3,4,5,6-d5
  参考文献：
  名称：

  使用具有 16 个外围甲基的单阳离子 μ-硝基桥连铁酞菁二聚体在温和反应条件下直接催化苯羟基化

  摘要：

  在含有过量 H 2 O 2的乙腈溶液中，在具有 16 个外围甲基的单阳离子 μ-硝基桥连铁酞菁二聚体的存在下，苯的直接催化羟基化反应在温和的反应条件下有效地进行。机理研究表明，该反应是由原位产生的高价铁氧物种催化的。此外，据推测，催化剂的外围甲基提高了铁氧物种的生产率。

  DOI：

  10.1039/d1nj05369h

文献信息

• Acid p<i>K</i>_a Dependence in O–O Bond Heterolysis of a Nonheme Fe^III–OOH Intermediate To Form a Potent Fe^V═O Oxidant with Heme Compound I-Like Reactivity
  作者：Shuangning Xu、Apparao Draksharapu、Waqas Rasheed、Lawrence Que

  DOI：10.1021/jacs.9b08442

  日期：2019.10.9

  rapid and catalytic hydroxylation of cyclohexane, and a million-fold acceleration in the decay rate of the FeIII-OOH intermediate at -40 °C. These results implicate the generation of a highly reactive FeV=O species via proton-assisted O-O bond heterolysis of the FeIII-OOH intermediate, which is unprecedented for nonheme iron complexes supported by neutral pentadentate ligands and serves as a nonheme

  质子在控制过氧铁 (III) 物质的 OO 键断裂以产生执行所需转化的高价铁氧化剂方面在自然系统中起着重要作用。在此，我们报告了动力学和机械证据，表明酸可以控制非血红素 S = ½ 自旋 FeIII-OOH 物质 [(BnTPEN)FeIII(OOH)]2+ (2, BnTPEN = N-苄基-N， N',N'-三(2-吡啶基甲基)-1,2-二氨基-乙烷)。在 CH3CN 中添加 pKa 值 > 8.5 的酸会导致 OO 键均裂，导致羟基自由基的形成，从而在环己烷氧化中使醇/酮 (A/K) 比值约为 1。然而，引入 pKa 值 < 8.5 的酸会导致不同的结果，即实现高达 9 的 A/K 比，观察到环己烷的快速和催化羟基化，以及 -40°C 下 FeIII-OOH 中间体的衰减速率加速百万倍。这些结果暗示通过 FeIII-OOH 中间体的质子辅助 OO 键异解产生高反应性 FeV=O 物种
• Palladium-Catalyzed Synthesis of Benzofurans and Coumarins from Phenols and Olefins
  作者：Upendra Sharma、Togati Naveen、Arun Maji、Srimanta Manna、Debabrata Maiti

  DOI：10.1002/anie.201305326

  日期：2013.11.25

  Triple CH functionalization: Palladium‐catalyzed synthesis of benzofurans and coumarins by reacting phenols and unactivated olefins is described. The reaction comprises sequential CH functionalization and shows diverse functional group compatibility. Preliminary mechanistic studies shed light into the possible mechanisms.

  三重CH官能化：描述了通过酚与未活化的烯烃反应，钯催化合成苯并呋喃和香豆素。该反应包括顺序的CH官能化，并显示出各种官能团相容性。初步的机理研究阐明了可能的机制。
• Synthesis and biological evaluation of deuterated sofosbuvir analogs as HCV NS5B inhibitors with enhanced pharmacokinetic properties
  作者：Wangwei Ao、Xueqin Ma、Youping Lin、Xiaojing Wang、Wei Song、Qinglin Wang、Xiquan Zhang、Hongjiang Xu、Yinsheng Zhang

  DOI：10.1002/jlcr.3715

  日期：2019.5.15

  A series of deuterated sofosbuvir analogs were designed and prepared with the aim of improving their pharmacokinetic properties. The devised synthetic routes allow for site-selective deuterium incorporation with high levels of isotopic purity. As expected, the deuterated analogs (37-44) are as efficacious as sofosbuvir when tested in vitro inhibition of viral replication (replicon) assays. Compared

  设计和制备了一系列氘代索非布韦类似物，旨在改善其药代动力学特性。所设计的合成路线允许以高同位素纯度进行位点选择性氘掺入。正如所料，氘代类似物 (37-44) 在体外抑制病毒复制（复制子）试验时与索非布韦一样有效。与索非布韦相比，氘代类似物 40 在大鼠和狗的代谢物和前药方面显示出改善的体内药代动力学特征。犬的 Cmax 和曲线下面积 (AUC) 为 40，分别增加了 3.4 倍和 2.7 倍。由于 40 的廉价氘源 (D2O) 具有增强的药代动力学特性和巨大的合成优势，因此选择它进行进一步研究。
• Catalytic Arene H/D Exchange with Novel Rhodium and Iridium Complexes
  作者：Jennifer L. Rhinehart、Kimberly A. Manbeck、Sara K. Buzak、Geoffrey M. Lippa、William W. Brennessel、Karen I. Goldberg、William D. Jones

  DOI：10.1021/om2012419

  日期：2012.3.12

  Three novel pendant acetate complexes, [Rh(bdmpza)Cl3]−M+, [Rh(bdmpza)Cl2(py)], and [Ir(bdmpza)Cl3]−M+ (bdmpza = bis(3,5-dimethylpyrazol-1-yl) acetate, M+ = Li+, Na+), were synthesized. Abstraction of halide from these complexes with silver salts yielded species capable of C–H activation of arenes. The catalytic H/D exchange reaction between benzene and trifluoroacetic acid-d was optimized, and these

  三种新型挂件乙酸配合物，铑[Rh（bdmpza）氯3 ] -中号+，铑[Rh（bdmpza）氯2（PY）]和[Ir（bdmpza）氯3 ] -中号+（bdmpza =双（3,5-合成了M +＝ Li +，Na +）的乙酸-二甲基吡唑-1-基酯。从这些配合物与银盐中提取卤化物可产生能够C–H活化芳烃的物质。苯与三氟乙酸的催化H / D交换反应-d进行了优化，并将这些条件用于评估其他领域的H / D交换。烷基芳族化合物中的支链烷基取代基仅对β-烷基位置显示出对氘交换的亲和力。进行DFT计算以确定H / D交换的机制。
• 氘代核苷衍生物
  申请人：正大天晴药业集团股份有限公司

  公开号：CN105254694B

  公开（公告）日：2018-11-27

  本发明涉及氘代核苷衍生物，具体而言，本发明涉及如式一种结构如式Ⅰ所示的化合物或其药学上可接受的盐。如式Ⅰ所示的化合物具有优异的药代动力学性质，有望降低临床的使用剂量，从而降低治疗成本以让更多患者受益。