2,2,4,6,7-五甲基二氢苯并呋喃-5-磺酰氯 | 154445-78-0

• 物质功能分类: 化学试剂 - 有机试剂 - 磺酸盐/亚磺酸盐
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 香豆素
• 中文名称: 2,2,4,6,7-五甲基二氢苯并呋喃-5-磺酰氯
• 中文别名: 2,2,4,6,7-五甲基二氢苯并呋喃；2,2,4,6,7-五甲基二氢苯并呋喃-5-磺酰氯化物；2,2,4,6,7-五甲基二氢苯并[B]呋喃-5-磺酰氯
• 英文名称: 2,2,4,6,7-pentamethyl-2,3-dihydrobenzofuran-5-sulfonyl chloride
• 英文别名: 2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl chloride；2,2,4,6,7-pentamethyl-3H-benzofuran-5-sulfonyl chloride；Pbf-Cl；2,2,4,6,7-pentamethyl-3H-1-benzofuran-5-sulfonyl chloride
• CAS: 154445-78-0
• 化学式: C₁₃H₁₇ClO₃S
• 分子量: 288.795
• InChiKey: HLJKUZUILACRPQ-UHFFFAOYSA-N

物化性质

• 熔点：
  69-71 °C
• 沸点：
  392.7±42.0 °C(Predicted)
• 密度：
  1.236±0.06 g/cm3(Predicted)
• 溶解度：
  乙腈（微溶）、氯仿（微溶）、DMSO（微溶）、甲醇（微溶）

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  51.8
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 危险等级：
  8
• 危险品标志：
  C
• 安全说明：
  S26,S36/37/39,S45
• 危险类别码：
  R34
• WGK Germany：
  3
• 危险品运输编号：
  UN 3261
• 海关编码：
  2932999099
• 包装等级：
  Ⅲ
• 危险类别：
  8
• 危险标志：
  GHS05
• 危险性描述：
  H314
• 危险性防范说明：
  P280,P305 + P351 + P338,P310

SDS

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Section 1. IDENTIFICATION OF THE SUBSTANCE/MIXTURE
Product identifiers
Product name : 2,2,4,6,7-Pentamethyldihydrobenzofuran-5-sulfonyl
chloride
CAS-No. : 154445-78-0
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 [EU-GHS/CLP]
Skin corrosion (Category 1B)
Classification according to EU Directives 67/548/EEC or 1999/45/EC
Causes burns.
Label elements
Labelling according Regulation (EC) No 1272/2008 [CLP]
Pictogram
Signal word Danger
Hazard statement(s)
H314 Causes severe skin burns and eye damage.
Precautionary statement(s)
P280 Wear protective gloves/ protective clothing/ eye protection/ face
protection.
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
According to European Directive 67/548/EEC as amended.
Hazard symbol(s)
R-phrase(s)
R34 Causes burns.
S-phrase(s)
S26 In case of contact with eyes, rinse immediately with plenty of water and
seek medical advice.
S36/37/39 Wear suitable protective clothing, gloves and eye/face protection.
S45 In case of accident or if you feel unwell, seek medical advice immediately
(show the label where possible).
Caution - substance not yet tested completely.
Other hazards - none

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substances
Synonyms : Pbf-Cl
Formula : C13H17ClO3S
Molecular Weight : 288,79 g/mol
Component Concentration
2,2,4,6,7-Pentamethyldihydrobenzofuran-5-sulfonyl chloride
CAS-No. 154445-78-0 -

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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. 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
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, Sulphur oxides, Hydrogen chloride gas
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
Use personal protective equipment. Avoid dust formation. Avoid breathing vapors, mist or gas. Ensure
adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust.
Environmental precautions
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 formation of dust and aerosols.
Provide appropriate exhaust ventilation at places where dust is formed.
Conditions for safe storage, including any incompatibilities
Store in cool place. Keep container tightly closed in a dry and well-ventilated place.
Recommended storage temperature: 2 - 8 °C
Store under inert gas. Moisture sensitive.
Specific end uses
no data available

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Section 8. EXPOSURE CONTROLS/PERSONAL PROTECTION
Control parameters
Components with workplace control parameters
Exposure controls
Appropriate engineering controls
Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and
at the end of workday.
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.
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).

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Section 9. PHYSICAL AND CHEMICAL PROPERTIES
Information on basic physical and chemical properties
a) Appearance Form: powder
Colour: light blue
b) Odour no data available
c) Odour Threshold no data available
d) pH no data available
e) Melting point/freezing Melting point/range: 69 - 71 °C
point
f) Initial boiling point and no data available
boiling range
g) Flash point no data available
h) Evaporation 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 no data available
n) Water solubility no data available
o) Partition coefficient: n- no data available
octanol/water
p) Autoignition 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
no data available
Possibility of hazardous reactions
no data available
Conditions to avoid
no data available
Incompatible materials
Strong oxidizing agents
Hazardous decomposition products
Other decomposition products - no data available

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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
no data available
Respiratory or skin sensitization
no data available
Germ cell mutagenicity
no data available
Carcinogenicity
IARC: No component of this product present at levels greater than or equal to 0.1% is identified as
probable, possible or confirmed human carcinogen by IARC.
Reproductive toxicity
no data available
Specific target organ toxicity - single exposure
no data available
Specific target organ toxicity - repeated exposure
no data available
Aspiration hazard
no data available
Potential health effects
Inhalation May be harmful if inhaled. Material is extremely destructive to the tissue of
the mucous membranes and upper respiratory tract.
Ingestion May be harmful if swallowed. Causes burns.
Skin May be harmful if absorbed through skin. Causes skin burns.
Eyes Causes eye burns.
Additional Information
RTECS: Not available

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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
no data available
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: 3261 IMDG: 3261 IATA: 3261
UN proper shipping name
ADR/RID: CORROSIVE SOLID, ACIDIC, ORGANIC, N.O.S. (2,2,4,6,7-Pentamethyldihydrobenzofuran-
5-sulfonyl chloride)
IMDG: CORROSIVE SOLID, ACIDIC, ORGANIC, N.O.S. (2,2,4,6,7-Pentamethyldihydrobenzofuran-
5-sulfonyl chloride)
IATA: Corrosive solid, acidic, organic, n.o.s. (2,2,4,6,7-Pentamethyldihydrobenzofuran-5-sulfonyl
chloride)
Transport hazard class(es)
ADR/RID: 8 IMDG: 8 IATA: 8
Packaging group
ADR/RID: III IMDG: III IATA: III
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
This safety datasheet complies with the requirements of Regulation (EC) No. 1907/2006.
Safety, health and environmental regulations/legislation specific for the substance or mixture
no data available
Chemical Safety Assessment
no data available

---

Section 16. OTHER INFORMATION
Further information
Copyright 2012 Co. LLC. License granted to make unlimited paper copies for internal use
only.
The above information is believed to be correct but does not purport to be all inclusive and shall be
used only as a guide. The information in this document is based on the present state of our knowledge
and is applicable to the product with regard to appropriate safety precautions. It does not represent any
guarantee of the properties of the product. Corporation and its Affiliates shall not be held
liable for any damage resulting from handling or from contact with the above product. See
and/or the reverse side of invoice or packing slip for additional terms and conditions of sale.

制备方法与用途

用途：2,2,4,6,7-五甲基二氢苯并呋喃-5-磺酰氯常被用作合成各种具有生物活性的药物分子的原料。在材料领域，它也可作为制备高分子材料、功能性聚合物和纳米材料的原料。

反应信息

• 作为反应物：
  描述：

  2,2,4,6,7-五甲基二氢苯并呋喃-5-磺酰氯 在 N-氯代丁二酰亚胺 、 C₃₃H₄₈N₄O₄ 、 水 、 silica gel 、 sodium hydride 、 碳酸氢钠 、 对甲苯磺酸 、 三乙胺 、 scandium tris(trifluoromethanesulfonate) 、 儿萘酚硼烷 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 氯仿 、 二甲基亚砜 为溶剂， 反应 82.67h， 生成
  参考文献：
  名称：

  基于催化不对称串联双迈克尔加成的(+)-异豆蔻碱不对称合成

  摘要：

  在此，(+)-异马钱子碱的简洁不对称合成通过 9 个最长的线性步骤实现，总产率为 16%。该合成的主要特征包括色胺衍生的羟吲哚与炔酮的催化不对称串联双迈克尔加成以轻松形成 A/B/C 环骨架，一锅分子内脱水缩合/内酰胺化反应以有效建立 E /G 环系统和烯丙基二氮烯重排以引入关键烯烃，用于随后的分子内 Heck 反应。

  DOI：

  10.1021/acs.orglett.1c01828
• 作为产物：
  描述：

  2,3,5-三甲基苯酚 在 氯磺酸 、 硫酸 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 2,2,4,6,7-五甲基二氢苯并呋喃-5-磺酰氯
  参考文献：
  名称：

  The 2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl group (Pbf) as arginine side chain protectant

  摘要：

  The 2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl residue (Pbf) is more easily deblocked by trifluoroacetic acid (TFA) than the corresponding Pmc analog and can be used efficiently in the synthesis of arginine-containing peptides.

  DOI：

  10.1016/s0040-4039(00)61487-9

文献信息

• Cardiosulfa, a Small Molecule that Induces Abnormal Heart Development in Zebrafish, and Its Biological Implications
  作者：Sung-Kyun Ko、Hui Juan Jin、Da-Woon Jung、Xizhe Tian、Injae Shin

  DOI：10.1002/anie.200902370

  日期：2009.10.5

  A change of heart: Cardiosulfa, a small molecule that induces heart deformation during zebrafish development, has been identified by using a forward chemical‐genetic approach. Zebrafish embryos exposed to cardiosulfa have a narrow and elongated heart within an enlarged pericardial sac (see picture; heart marked with green fluorescent protein).

  心脏的变化：心律不齐是在斑马鱼发育过程中引起心脏变形的小分子，已经通过使用正向化学遗传学方法进行了鉴定。暴露于心硫酸盐的斑马鱼胚胎在扩大的心包中有一个狭窄而细长的心脏（见图）；心脏带有绿色荧光蛋白标记。
• METHOD FOR MANUFACTURING NOVEL NITROGEN-CONTAINING COMPOUND OR SALT THEREOF AND MANUFACTURING INTERMEDIATE OF NOVEL NITROGEN-CONTAINING COMPOUND OR SALT THEREOF
  申请人：FUJIFILM Corporation

  公开号：US20180008583A1

  公开（公告）日：2018-01-11

  Provided are a method for efficiently manufacturing a nitrogen-containing compound, which is used for manufacturing a treatment agent for integrin-related diseases, or a salt thereof and a manufacturing intermediate of the compound or a salt thereof. A method for manufacturing a novel nitrogen-containing compound or a salt thereof includes (1) a step of obtaining a compound represented by Formula [10] or a salt thereof through an amidation reaction; and (2) a step of deprotecting the compound represented by Formula [10] or a salt thereof.

  提供了一种用于高效制造含氮化合物的方法，该方法用于制造治疗整合素相关疾病的治疗剂或其盐，以及该化合物或其盐的制造中间体。 制造一种新型含氮化合物或其盐的方法包括（1）通过酰胺化反应获得由式[10]表示的化合物或其盐的步骤；以及（2）去保护由式[10]表示的化合物或其盐的步骤。
• Design and Synthesis of TASIN Analogues Specifically Targeting Colorectal Cancer Cell Lines with Mutant Adenomatous Polyposis Coli (APC)
  作者：Wentian Wang、Lu Zhang、Lorraine Morlock、Noelle S. Williams、Jerry W. Shay、Jef K. De Brabander

  DOI：10.1021/acs.jmedchem.9b00532

  日期：2019.5.23

  small-molecule-based therapies available that specifically target colorectal cancer (CRC) development and progression, the second leading cause of cancer deaths. We previously disclosed the discovery of truncating adenomatous polyposis coli (APC)-selective inhibitor 1 (TASIN-1), a small molecule that specifically targets colorectal cancer cells lines with truncating mutations in the adenomatous polyposis

  尽管靶向抗癌疗法取得了进展，但仍没有针对小分子结肠直肠癌（CRC）发育和进程的小分子疗法，这是导致癌症死亡的第二大原因。我们先前披露了截短性腺瘤性结肠炎（APC）选择性抑制剂1（TASIN-1）的发现，这是一种小分子，可通过抑制腺瘤性息肉病（APC）肿瘤抑制基因中的截短突变而特异性靶向结直肠癌细胞系胆固醇的生物合成。在这里，我们报告了TASIN类似物的集合及其对结肠癌细胞系和等基因细胞系对活性的报告，报告了APC依赖选择性的状态。鉴定出许多有效的和选择性的类似物，包括具有良好代谢稳定性和药代动力学特性的化合物。本文报道的化合物代表了首个基因型选择性系列，该系列特异性靶向大多数CRC患者中存在的apc突变，并充当结肠癌靶向治疗的翻译平台。
• Double C–N bond cleavages of <i>N</i>-alkyl 4-oxopiperidinium salts: access to unsymmetrical tertiary sulfonamides
  作者：Ying Fu、Ming-Peng Li、Chun-Zhao Shi、Fang-Rong Li、Zhengyin Du、Congde Huo

  DOI：10.1039/c9ob02107h

  日期：——

  paper, regiospecific, double intraannular C–N bond cleavages of N-alkyl 4-oxopiperidinium salts are presented. The reaction sequence involves a charge-transfer complex, in situ formed between sulfonyl chloride and N-methylmorpholine, which induces S–Cl bond homolysis of sulfonyl chloride, yielding a reactive sulfonyl radical that further induces the double C–N bond cleavages of N-alkyl 4-oxopiperidinium

  在本文中，提出了N-烷基4-氧代哌啶鎓盐的区域特异性双环内C–N键裂解。反应顺序包括一个电荷转移络合物，原位磺酰氯和之间形成Ñ甲基吗啉，磺酰氯，其诱导S-Cl键均裂，产生反应性基团磺酰进一步诱导的双C-N键断裂ñ -烷基4-氧代哌啶鎓盐。如此产生的仲胺被磺酰氯捕获，得到所需的磺酰胺产物。该协议的关键特征是，在无金属和无氧化剂的条件下，一步切割了4-氧杂环哌啶环的两个环内C–N键。
• Design, synthesis and bioevaluation of inhibitors targeting HSP90-CDC37 protein-protein interaction based on a hydrophobic core
  作者：Qiuyue Zhang、Xuexuan Wu、Jianrui Zhou、Lixiao Zhang、Xiaoli Xu、Lianshan Zhang、Qidong You、Lei Wang

  DOI：10.1016/j.ejmech.2020.112959

  日期：2021.1

  interface, design of small molecule inhibitors targeting HSP90-CDC37 PPI is challenging. In this work, based on the binding mode of compound 11 (previously reported by our group), we discovered a hydrophobic pocket centered on Phe213, which was previously unknown, contributing to the binding affinity of HSP90-CDC37 PPI inhibitors. A series of hydrophobic substituted inhibitors were utilized to confirm the

  HSP90-CDC37蛋白-蛋白相互作用（PPI）作为激酶特异性分子伴侣系统来调节激酶的成熟。当前，选择性地破坏HSP90-CDC37 PPI，而不是直接抑制HSP90的ATPase功能，正在通过特异性地阻断激酶的成熟而成为一种有前景的癌症治疗策略。但是，由于对HSP90-CDC37结合界面的了解有限，靶向HSP90-CDC37 PPI的小分子抑制剂的设计具有挑战性。在这项工作中，基于化合物11的结合方式（我们小组先前的报道），我们发现了一个以Phe213为中心的疏水口袋，该口袋以前是未知的，有助于形成HSP90-CDC37 PPI抑制剂的结合亲和力。利用一系列疏水取代的抑制剂来确认Phe213疏水核心的重要性。最后，我们得到的最佳化合物DDO-5994具有改善的结合亲和力（（显示对疏水核的理想结合模式）ķ d  = 5.52  μ M）和抗增殖活性（IC 50  = 6.34  μ M）