苯基(4-吡啶基)甲醇 | 33974-27-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 中文名称: 苯基(4-吡啶基)甲醇
• 中文别名: 苯基(吡啶-4-基)甲醇
• 英文名称: phenyl(pyridin-4-yl)methanol
• 英文别名: 4-(α-hydroxybenzyl)pyridine；(phenyl)(4-pyridyl)methanol；α-phenyl-4-pyridylmethanol
• CAS: 33974-27-5
• 化学式: C₁₂H₁₁NO
• mdl: MFCD00277656
• 分子量: 185.225
• InChiKey: MYKGGGPMKINROD-UHFFFAOYSA-N

物化性质

• 熔点：
  124 °C
• 沸点：
  353.5±27.0 °C(Predicted)
• 密度：
  1.155±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.083
• 拓扑面积：
  33.1
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 危险品标志：
  Xn
• 危险类别码：
  R22,R36/37/38
• 海关编码：
  2933399090
• 安全说明：
  S26,S37/39
• 储存条件：
  2-8°C

SDS

Name:	Phenyl(4-pyridyl)methanol 97% Material Safety Data Sheet
Synonym:
CAS:	33974-27-5

Section 1 - Chemical Product MSDS Name:Phenyl(4-pyridyl)methanol 97% Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
33974-27-5	Phenyl(4-pyridyl)methanol	97%	251-770-1

Hazard Symbols: XN
Risk Phrases: 22 36/37/38

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Harmful if swallowed. Irritating to eyes, respiratory system and skin.
Potential Health Effects
Eye:
Causes eye irritation.
Skin:
Causes skin irritation. May be harmful if absorbed through the skin.
Ingestion:
Harmful if swallowed. May cause irritation of the digestive tract.
Inhalation:
Causes respiratory tract irritation. May be harmful if inhaled.
Chronic:
Not available.

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Section 4 - FIRST AID MEASURES
Eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid.
Skin:
Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes.
Ingestion:
Get medical aid. Wash mouth out with water.
Inhalation:
Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid.
Notes to Physician:
Treat symptomatically and supportively.

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Section 5 - FIRE FIGHTING MEASURES
General Information:
As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear.
Extinguishing Media:
Use water spray, dry chemical, carbon dioxide, or chemical foam.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Vacuum or sweep up material and place into a suitable disposal container.

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Section 7 - HANDLING and STORAGE
Handling:
Avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and eyes.
Storage:
Store in a cool, dry place. Store in a tightly closed container.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Facilities storing or utilizing this material should be equipped with an eyewash facility and a safety shower. Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 33974-27-5: Personal Protective Equipment Eyes: Not available.
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: Solid
Color: Not available.
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 120 - 123 deg C
Autoignition Temperature: Not available.
Flash Point: Not available.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C12H11NO
Molecular Weight: 185.23

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Not available.
Conditions to Avoid:
Incompatible materials.
Incompatibilities with Other Materials:
Strong oxidizing agents.
Hazardous Decomposition Products:
Nitrogen oxides, carbon monoxide, carbon dioxide.
Hazardous Polymerization: Not available.

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 33974-27-5 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
Phenyl(4-pyridyl)methanol - 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
No information available.
IMO
No information available.
RID/ADR
No information available.

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: XN
Risk Phrases:
R 22 Harmful if swallowed.
R 36/37/38 Irritating to eyes, respiratory system
and skin.
Safety Phrases:
S 26 In case of contact with eyes, rinse immediately
with plenty of water and seek medical advice.
S 37/39 Wear suitable gloves and eye/face
protection.
WGK (Water Danger/Protection)
CAS# 33974-27-5: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 33974-27-5 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 33974-27-5 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

反应信息

• 作为反应物：
  描述：

  苯基(4-吡啶基)甲醇 在 copper dichloride 、 2,2'-biquinoline-4,4'-dicarboxylic acid dipotassium salt 叔丁基过氧化氢 、 四丁基氯化铵 、 sodium carbonate 作用下， 以 水 为溶剂， 反应 24.0h， 以100%的产率得到4-苯甲酰吡啶
  参考文献：
  名称：

  一种新型高效水溶性铜络合物，用于叔丁基氢过氧化物氧化仲1-杂芳基醇

  摘要：

  由CuCl 2和2,2'-联喹啉-4,4'-二羧酸二钾盐（BQC）原位生成的水溶性铜络合物已被证明是一种高效且选择性的催化剂，可氧化次要1-在温和条件下，用叔丁基过氧化氢水溶液将杂芳基醇转变为相应的杂芳族酮。该催化体系与不同的杂环兼容，例如吡啶，吡咯，吲哚，噻吩，呋喃，噻唑和咪唑。

  DOI：

  10.1016/j.tetlet.2006.01.061
• 作为产物：
  描述：

  4-碘吡啶 在 乙基溴化镁 作用下， 以 四氢呋喃 为溶剂， 反应 6.42h， 生成 苯基(4-吡啶基)甲醇
  参考文献：
  名称：

  吡啶基格氏试剂的制备和与含氮杂杂环的亚砜的交叉偶联反应

  摘要：

  由相应的碘吡啶和EtMgBr制备吡啶基格氏试剂。格氏试剂与氮杂杂环的新的交叉偶联反应在亚磺酰基硫原子上发生，从而得到重氮杂芳基。

  DOI：

  10.1016/s0040-4039(01)81070-4

文献信息

• MODIFIED COMPOUND OF ANDROGRAPHOLIDE
  申请人：Heilongjiang Zhenbaodao Pharmaceutical Co., Ltd.

  公开号：US20180346438A1

  公开（公告）日：2018-12-06

  The present disclosure discloses a modified compound of andrographolide, and particularly discloses a compound shown in formula (I) and (II) or a pharmaceutically acceptable salt thereof.

  本公开披露了穿心莲内酯的修改化合物，特别是公开了公式(I)和(II)所示的化合物或其药用可接受的盐。
• Rapid, chemoselective and mild oxidation protocol for alcohols and ethers with recyclable N-chloro-N-(phenylsulfonyl)benzenesulfonamide
  作者：Amey Palav、Balu Misal、Prerna Ganwir、Purav Badani、Ganesh Chaturbhuj

  DOI：10.1016/j.tetlet.2021.153094

  日期：2021.6

  most abundant element on the earth compared to bromine, iodine, and fluorine, a sulfonimide reagent, N-chloro-N-(phenylsulfonyl)benzenesulfonamide (NCBSI) was identified as a mild and selective oxidant. Without activation, the reagent was proved to oxidize primary and secondary alcohols as well as their symmetrical and mixed ethers to corresponding aldehydes and ketones. With recoverable PS-TEMPO catalyst

  与溴、碘和氟（一种磺酰亚胺试剂）相比，氯是地球上第20 位最丰富的元素，N-氯-N-（苯磺酰基）苯磺酰胺 (NCBSI) 被确定为一种温和的选择性氧化剂。在没有活化的情况下，该试剂被证明可以将伯醇和仲醇以及它们的对称和混合醚氧化成相应的醛和酮。使用可回收的 PS-TEMPO 催化剂，实现了伯醇和仲醇及其醚与给电子取代基的氯化选择性氧化。NCBSI的试剂前体被定量回收，可重复用于合成NCBSI。
• Cobalt-Catalyzed Addition Reaction of Organoboronic Acids with Aldehydes: Highly Enantioselective Synthesis of Diarylmethanols
  作者：Jaganathan Karthikeyan、Masilamani Jeganmohan、Chien-Hong Cheng

  DOI：10.1002/chem.201001160

  日期：——

  Predicted outcomes: The addition reaction of organoboronic acids with aldehydes in the presence of K2CO3 catalyzed by CoI2/(R,R)‐BDPP gives chiral secondary alcohols in excellent yields with 90–99 % enantiomeric excess (see scheme; (R,R)‐BDPP=(2R,4R)‐(+)‐2,4‐bis(diphenylphosphino)pentane). This method provides an alternative to prepare an R and S enantiomeric pair by using the same chiral ligand and

  预期的结果：在CoI 2 /（R，R）-BDPP催化下，在存在K 2 CO 3的情况下，有机硼酸与醛的加成反应可得到出色的手性仲醇，对映体过量90-99％（参见方案；（R，R）-BDPP =（2 R，4 R）-（+）-2,4-双（二苯基膦基）戊烷）。该方法提供了另一种通过使用相同的手性配体制备R和S对映体对的方法，并且可以预测反应的立体化学结果。
• Rabbit 3-hydroxyhexobarbital dehydrogenase is a NADPH-preferring reductase with broad substrate specificity for ketosteroids, prostaglandin D2, and other endogenous and xenobiotic carbonyl compounds
  作者：Satoshi Endo、Toshiyuki Matsunaga、Atsuko Matsumoto、Yuki Arai、Satoshi Ohno、Ossama El-Kabbani、Kazuo Tajima、Yasuo Bunai、Shigeru Yamano、Akira Hara、Yukio Kitade

  DOI：10.1016/j.bcp.2013.08.024

  日期：2013.11

  for NADP(H) over NAD(H) at a physiological pH of 7.4. In the NADPH-linked reduction, 3HBD showed broad substrate specificity for a variety of quinones, ketones and aldehydes, including 3-, 17- and 20-ketosteroids and prostaglandin D(2), which were converted to 3alpha-, 17beta- and 20alpha-hydroxysteroids and 9alpha,11beta-prostaglandin F(2), respectively. Especially, alpha-diketones (such as isatin

  3-羟基己异巴比妥脱氢酶（3HBD）催化将NAD（P）（+）链接的3-羟基己异巴比妥氧化为3-羟基己异巴比妥。该酶被认为是异生物醇和某些羟基类固醇的脱氢酶，但其生理功能仍然未知。我们已经纯化了兔3HBD，分离了其cDNA，并检查了其对辅酶和底物的特异性，反应方向性和组织分布。3HBD是醛酮还原酶（AKR）超家族的成员（AKR1C29），并且在7.4的生理pH值下，NADP（H）优于NAD（H）。在与NADPH相关的还原反应中，3HBD对多种醌，酮和醛（包括3-，17-和20-酮类固醇和前列腺素D（2））显示出广泛的底物特异性，它们被转化为3alpha-，17beta-和20alpha -羟基类固醇和9alpha，11beta-前列腺素F（2），分别。特别是，α-二酮（如isatin和diacetyl）和脂质过氧化衍生的醛（如4-oxo-和4-hydroxy-2-nonenals）是显示低K（m）值（0
• Carbonyl Reductase Activity Exhibited by Pig Testicular 20.BETA.-Hydroxysteroid Dehydrogenase.
  作者：Shizuo NAKAJIN、Fumihiro TAMURA、Noriko TAKASE、Satoshi TOYOSHIMA

  DOI：10.1248/bpb.20.1215

  日期：——

  The carbonyl reductase activity exhibited by pig testicular 20β-hydroxysteroid dehydrogenase (20β-HSD) was examined using a recombinant enzyme. Kinetic parameters were obtained for 48 carbonyl group-containing substrates, including aromatic aldehydes, aromatic ketones, cycloketones, quinones, aliphatic aldehydes and aliphatic ketones. 20β-HSD showed a high affinity towards quinones, such as 9, 10-phenanthrenequinone, α-naphthoquinone and menadione (Km values of 4, 2 and 5 μM, respectively), and the substrate utilization efficiency (Vmax/Km) of the enzyme against these quinones was very high. Cyclohexanone and 2-methylcyclohexanone were also reduced with a high Vmax/Km value, but not cyclopentanone or 2-methylcyclopentanone. Various aromatic aldehydes and ketones including benzaldehyde- and acetophenone-derivatives were reduced by 20β-HSD. Especially, 4-nitrobenzaldehyde and 4-nitroacetophenone were reduced with high Vmax/Km values in related compounds. The enzyme also reduced the pyridine-derivatives, 2-, 3-, and 4-benzoylpyridine, with the Vmax/Km value for 2-benzoylpyridine being the highest. 20β-HSD reduced aliphatic aldehydes and aliphatic ketones, but was more effective on the former. The correlation between the structure of carbonyl compounds and their substrate Vmax/Km is discussed.

  利用重组酶检测了猪睾丸20β-羟基类固醇脱氢酶(20β-HSD)表现出的羰基还原酶活性。获得了包括芳香醛、芳香酮、环酮、醌、脂肪醛和脂肪酮在内的48种含羰基基团底物的动力学参数。20β-HSD对醌类如9,10-菲醌、α-萘醌和维生素K3表现出高亲和性(Km值分别为4、2和5 μM)，且该酶对这些醌的底物利用效率(Vmax/Km)非常高。环己酮和2-甲基环己酮也以高Vmax/Km值被还原，但环戊酮和2-甲基环戊酮未被还原。各种芳香醛和酮类包括苯甲醛和苯乙酮的衍生物均被20β-HSD还原。尤其是，4-硝基苯甲醛和4-硝基苯乙酮在相关化合物中以高Vmax/Km值被还原。该酶也还原吡啶衍生物，2-、3-和4-苯甲酰吡啶，其中2-苯甲酰吡啶的Vmax/Km值最高。20β-HSD还原脂肪醛和脂肪酮，但对前者的还原效率更高。讨论了羰基化合物的结构和其底物Vmax/Km之间的相关性。

表征谱图