巴豆酸 | 3724-65-0

• 物质功能分类: 生物化工 - 生化试剂 - 生物染料
• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: 巴豆酸
• 中文别名: 巴豆油酸；丁烯酸；2-丁烯酸；反式丁烯酸
• 英文名称: 2-butenoic acid
• 英文别名: crotonic acid；but-2-enoic acid；butenoic acid；3-methylacrylic acid；vinyl acetic acid
• CAS: 3724-65-0
• 化学式: C₄H₆O₂
• 分子量: 86.0904
• InChiKey: LDHQCZJRKDOVOX-UHFFFAOYSA-N

物化性质

• 熔点：
  70-72 °C(lit.)
• 沸点：
  180-181 °C(lit.)
• 密度：
  1.027 g/mL at 25 °C(lit.)
• 蒸气密度：
  2.97 (vs air)
• 闪点：
  190 °F
• LogP：
  0.720
• 保留指数：
  986
• 稳定性/保质期：
  1. 常温常压下稳定，呈单斜针状或棱状结晶。 2. 广泛存在于烤烟烟叶、白肋烟烟叶和香料烟烟叶以及烟气中。

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  6
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 危险品标志：
  C
• 安全说明：
  S26,S36/37/39,S45
• 危险类别码：
  R21/22,R34
• WGK Germany：
  3
• 危险品运输编号：
  UN 2823 8/PG 3
• 海关编码：
  2916190090
• RTECS号：
  GQ2900000
• 包装等级：
  III
• 危险类别：
  8
• 储存条件：
  常温、避光、通风干燥处，密封保存。

SDS

---

Section 1. Chemical Product and Company Identification
Crotonic acid
Common Name/
Trade Name
Manufacturer
Commercial Name(s)
Synonym
Chemical Name
Chemical Family
Crotonic acid

---

Section 4. First Aid Measures
Eye Contact Check for and remove any contact lenses. In case of contact, immediately flush eyes with plenty of water
for at least 15 minutes. Cold water may be used. Get medical attention immediately.
Skin Contact In case of contact, immediately flush skin with plenty of water for at least 15 minutes while removing
contaminated clothing and shoes. Cover the irritated skin with an emollient. Cold water may be used.Wash
clothing before reuse. Thoroughly clean shoes before reuse. Get medical attention immediately.
Serious Skin Contact Wash with a disinfectant soap and cover the contaminated skin with an anti-bacterial cream. Seek
immediate medical attention.
Inhalation If inhaled, remove to fresh air. If not breathing, give artificial respiration. If breathing is difficult, give oxygen.
Get medical attention.
Serious Inhalation Evacuate the victim to a safe area as soon as possible. Loosen tight clothing such as a collar, tie, belt or
waistband. If breathing is difficult, administer oxygen. If the victim is not breathing, perform mouth-to-mouth
resuscitation. WARNING: It may be hazardous to the person providing aid to give mouth-to-mouth
resuscitation when the inhaled material is toxic, infectious or corrosive. Seek immediate medical attention.
Ingestion Do NOT induce vomiting unless directed to do so by medical personnel. Never give anything by mouth to
an unconscious person. If large quantities of this material are swallowed, call a physician immediately.
Loosen tight clothing such as a collar, tie, belt or waistband.
Serious Ingestion Not available.

---

Section 5. Fire and Explosion Data
Flammability of the Product Combustible.
Auto-Ignition Temperature 396°C (744.8°F)
OPEN CUP: 88°C (190.4°F).
Flash Points
Not available.
Flammable Limits
These products are carbon oxides (CO, CO2).
Products of Combustion
Fire Hazards in Presence of Flammable in presence of open flames and sparks, of heat.
Various Substances
Risks of explosion of the product in presence of mechanical impact: Not available.
Explosion Hazards in
Risks of explosion of the product in presence of static discharge: Not available.
Presence of Various
Substances
Fire Fighting Media SMALL FIRE: Use DRY chemical powder.
and Instructions LARGE FIRE: Use water spray, fog or foam. Do not use water jet.
When heated to decomposition it emits acrid smoke and irritating fumes, carbon dioxide, carbon monoxide.
Special Remarks on
Fire Hazards
Special Remarks on Explosion Not available.
Hazards

---

Section 6. Accidental Release Measures
Small Spill Dilute with water and mop up, or absorb with an inert dry material and place in an appropriate waste
disposal container.
Large Spill Combustible material. Corrosive liquid.
Keep away from heat. Keep away from sources of ignition. Stop leak if without risk. Absorb with DRY
earth, sand or other non-combustible material. Do not get water inside container. Do not touch spilled
material. Use water spray curtain to divert vapor drift. Prevent entry into sewers, basements or confined
Crotonic acid

---

Section 7. Handling and Storage
Precautions Keep container dry. Keep away from heat. Keep away from sources of ignition. Ground all equipment
containing material. Do not ingest. Do not breathe gas/fumes/ vapor/spray. Never add water to this
product. In case of insufficient ventilation, wear suitable respiratory equipment. If ingested, seek medical
advice immediately and show the container or the label. Avoid contact with skin and eyes. Keep away from
incompatibles such as oxidizing agents.
Storage Keep container in a cool, well-ventilated area. Keep container tightly closed and sealed until ready for use.
Avoid all possible sources of ignition (spark or flame).

---

Section 8. Exposure Controls/Personal Protection
Engineering Controls Provide exhaust ventilation or other engineering controls to keep the airborne concentrations of vapors
below their respective threshold limit value. Ensure that eyewash stations and safety showers are proximal
to the work-station location.
Personal Protection Face shield. Full suit. Vapor respirator. Be sure to use an approved/certified respirator or equivalent.
Gloves. Boots. Respiratory protection is not necessary for normal handling. Good room ventilation or use
of local exhaust (fume hood) is sufficient. Use a vapor respirator under conditions where exposure to the
substance is apparent (e.g. generation of high concentrations of mist or vapor or dust, inadequate
ventilation, development of respiratory tract irritation), and engineering controls are not feasible. Be sure to
use an approved/certified respirator or equivalent.
Personal Protection in Case of Splash goggles. Full suit. Vapor respirator. Boots. Gloves. A self contained breathing apparatus should
a Large Spill be used to avoid inhalation of the product. Suggested protective clothing might not be sufficient; consult a
specialist BEFORE handling this product.
Exposure Limits Not available.

---

Section 9. Physical and Chemical Properties
Physical state and appearance Liquid. Not available.
Odor
Taste Not available.
Molecular Weight 86.09 g/mole
Color Not available.
pH (1% soln/water) Not available.
185°C (365°F)
Boiling Point
Melting Point 72°C (161.6°F)
Critical Temperature Not available.
Specific Gravity 0.9604 - 1.03 (Water = 1)
Vapor Pressure 0 kPa (@ 20°C)
2.97 (Air = 1)
Vapor Density
Volatility Not available.
Not available.
Odor Threshold
Water/Oil Dist. Coeff. Not available.
Ionicity (in Water) Not available.
Dispersion Properties See solubility in water, diethyl ether, acetone.
Solubility Easily soluble in hot water.
Soluble in cold water, diethyl ether, acetone.
SOLUBLE IN HOT PETROLEUM ETHER
IN ETHANOL @ 25 DEG C: 52.5% WT/WT; ACETONE @ 25 DEG C: 53.0% W/W; IN TOLUENE @ 25
DEG C: 37.5% WT/WT
Water solubility: 8.6X10+4 mg/l at 25 deg C
555 g/l in water at 20 deg C
Crotonic acid

---

Section 10. Stability and Reactivity Data
The product is stable.
Stability
Instability Temperature Not available.
Heat, ignition sources, incompatible materials
Conditions of Instability
Incompatibility with various Reactive with oxidizing agents.
substances
Non-corrosive in presence of glass.
Corrosivity
Special Remarks on Not available.
Reactivity
Special Remarks on Not available.
Corrosivity
Will not occur.
Polymerization

---

Section 11. Toxicological Information
Routes of Entry Inhalation. Ingestion.
Toxicity to Animals Acute oral toxicity (LD50): 1000 mg/kg [Rat].
Acute dermal toxicity (LD50): 200 mg/kg [Guinea pig].
Chronic Effects on Humans May cause damage to the following organs: lungs.
Other Toxic Effects on Very hazardous in case of skin contact (irritant), of ingestion.
Humans Hazardous in case of skin contact (corrosive), of eye contact (corrosive), of inhalation.
Special Remarks on Not available.
Toxicity to Animals
Special Remarks on Not available.
Chronic Effects on Humans
Special Remarks on other Acute Potential Health Effects:
Toxic Effects on Humans Skin: Corrosive. Causes severe irritation and burns.
Eyes: Corrosive. Causes severe irritation and burns.
Inhalation: Breathing in Crotonic Acid can irritate the nose and throat causing coughing and wheezing. It
may cause burns to the respiratory tract.
Ingestion: May be harmful if swallowed. Can cause digestive tract/gastrointestinal tract burns.
Chronic Potential Health Effects:
Inhalation: It can irritate the lungs. Repeated exposure may cause bronchitis to develop with cough,
phlegm, and/or shortness of breath.

---

Section 12. Ecological Information
Not available.
Ecotoxicity
BOD5 and COD Not available.
Products of Biodegradation Possibly hazardous short term degradation products are not likely. However, long term degradation
products may arise.
Toxicity of the Products The products of degradation are less toxic than the product itself.
of Biodegradation
Special Remarks on the Not available.
Products of Biodegradation
Crotonic acid

---

Section 13. Disposal Considerations
Waste Disposal Waste must be disposed of in accordance with federal, state and local environmental
control regulations.

---

Section 14. Transport Information
DOT Classification Class 8: Corrosive material
UNNA: 2823 : Crotonic Acid, solid PG: III
Identification
Not available.
Special Provisions for
Transport
DOT (Pictograms)

---

Section 15. Other Regulatory Information and Pictograms
Pennsylvania RTK: Crotonic acid
Federal and State
Massachusetts RTK: Crotonic acid
Regulations
New Jersey: Crotonic acid
TSCA 8(b) inventory: Crotonic acid
California California prop. 65: This product contains the following ingredients for which the State of California has
Proposition 65 found to cause cancer which would require a warning under the statute: No products were found.
Warnings
California prop. 65: This product contains the following ingredients for which the State of California has
found to cause birth defects which would require a warning under the statute: No products were found.
Other Regulations OSHA: Hazardous by definition of Hazard Communication Standard (29 CFR 1910.1200).
EINECS: This product is on the European Inventory of Existing Commercial Chemical Substances (EINECS
No. 223-077-4).
Canada: Listed on Canadian Domestic Substance List (DSL).
China: Listed on National Inventory.
Japan: Listed on National Inventory (ENCS).
Korea: Listed on National Inventory (KECI).
Philippines: Listed on National Inventory (PICCS).
Australia: Listed on AICS.
WHMIS (Canada) CLASS E: Corrosive liquid.
Other Classifications
DSCL (EEC) R34- Causes burns. 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).
Health Hazard
HMIS (U.S.A.) 3 National Fire Protection
2 Flammability
2 Association (U.S.A.)
Fire Hazard
3 0 Reactivity
Health
Reactivity
0
Specific hazard
Personal Protection
WHMIS (Canada)
(Pictograms)
Crotonic acid
DSCL (Europe)
(Pictograms)
TDG (Canada)
(Pictograms)
ADR (Europe)
(Pictograms)
Protective Equipment
Gloves.
Full suit.
Vapor respirator. Be sure to use an
approved/certified respirator or
equivalent. Wear appropriate respirator
when ventilation is inadequate.

---

SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

用途 反式丁烯酸广泛用于涂料、共聚体、医药和农药等重要的有机化工中间体，也主要用于合成树脂、增塑剂及药物的制备，并应用于其他有机合成。

类别 腐蚀物品

毒性分级 低毒

急性毒性 口服 - 大鼠 LD50: 1000 毫克/公斤；小鼠 LD50: 4800 毫克/公斤

刺激数据 皮肤 - 兔子 10 毫克/24 小时

可燃性危险特性 可燃，受热分解会产生有毒烟雾

储运特性 应存放在库房内保持通风、低温和干燥，并与氧化剂及碱类分开存放

灭火剂 可用雾状水、二氧化碳、泡沫或干粉进行灭火

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  异巴豆酸	(Z)-but-2-enoic acid	503-64-0	C4H6O2	86.0904
  ——	(E)-4-chlorobut-2-enoic acid	26340-58-9	C4H5ClO2	120.535
  ——	(Z)-3-chloro-2-butenoic acid	6213-90-7	C4H5ClO2	120.535
  ——	(E)-3-chloro-2-butenoic acid	6214-28-4	C4H5ClO2	120.535
  2-丁烯酸乙酯	ethyl crotonate	10544-63-5	C6H10O2	114.144
  ——	2-chloro-crotonic acid	22038-56-8	C4H5ClO2	120.535
  (Z)-2-溴-2-丁烯酸	(Z)-2-bromobut-2-enoic acid	5405-34-5	C4H5BrO2	164.986
  (E)-2-溴丁-2-烯酸	(E)-2-bromo-2-butenoic acid	36297-22-0	C4H5BrO2	164.986

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  异巴豆酸	(Z)-but-2-enoic acid	503-64-0	C4H6O2	86.0904
  顺丁烯二酸	maleic acid	110-16-7	C4H4O4	116.073
  ——	4-bromocrotonic acid	20629-35-0	C4H5BrO2	164.986
  4-溴巴豆酸	4-bromocrotonic acid	13991-36-1	C4H5BrO2	164.986
  巴豆酸甲酯	Methyl crotonate	623-43-8	C5H8O2	100.117
  巴豆酸甲酯	methyl crotonate	18707-60-3	C5H8O2	100.117
  2-丁烯酸乙酯	ethyl crotonate	10544-63-5	C6H10O2	114.144
  反式-2-丁烯酸乙酯	Ethyl crotonate	623-70-1	C6H10O2	114.144

反应信息

• 作为反应物：
  描述：

  巴豆酸 在 氢气 作用下， 以 水 为溶剂， 120.0 ℃ 、1.0 MPa 条件下， 生成 丁酸
  参考文献：
  名称：

  具有富电子 Ni 位点的耐酸金属间 CaNi2Si2 催化剂，用于不饱和有机酸酐/酸的水相加氢

  摘要：

  顺丁烯二酸水相选择加氢制丁二酸的研究对于拓展煤化工产业链、促进生物质转化具有重要意义。关键在于开发高效稳定的非贵金属催化剂。在此，我们报道了一种新型金属间化合物CaNi 2 Si 2催化剂，具有高活性和稳定性，用于马来酸酐的水相选择性加氢。实验和理论计算结果表明，高催化性能归因于富电子Ni活性位点的协同作用、C=C键吸附的增强以及H 2 的有利活化。琥珀酸收率比CaNi 2 Si 2可达100%在连续流动反应器中，在3 MPa和120℃下，接触时间为5.4 g cat /(mmol反应物·min -1 )的催化剂。此外，CaNi 2 Si 2中Ni特殊的配位环境和电子结构抑制了羧酸盐的形成，从而增强了反应环境中的耐酸性。金属间硅化物结构的精细设计和调控将为马来酸酐加氢催化剂的可控优化提供重要参考，并为开发恶劣反应环境下高效稳定的选择性加氢催化剂提供新的见解。

  DOI：

  10.1016/s1872-2067(23)64473-0
• 作为产物：
  描述：

  巴豆醇 在 sodium ruthenate(VI) sodium hydroxide 、 hexacyanoferrate(III) 作用下， 以 水 为溶剂， 生成 巴豆酸
  参考文献：
  名称：

  钌酸离子催化高铁酸六氰合铁（III）离子氧化某些不饱和醇

  摘要：

  在恒定离子强度下，六氰合铁酸酯（III）离子在恒定的离子强度下，钌酸离子催化烯丙醇，巴豆醇，肉桂醇和炔丙醇被氧化的动力学表明速率与碱浓度或离子强度无关。该反应显示出对钌酸根离子的一级依赖性，而六氰基高铁酸根（III）离子中的零级依赖性。反应速率随底物浓度的增加而增加，并表现出Michaelis-Menten类型的行为。数据表明，氧化是通过在醇分子和钌酸离子之间形成络合物而进行的，从而产生相应的酸。已经在四个不同的温度下研究了该反应，并计算了热力学参数。提出了与实验结果相符的合理机制。

  DOI：

  10.1016/s0040-4020(01)91859-9
• 作为试剂：
  描述：

  硫酸 、 碘 、 potassium nitrate 在 巴豆酸 作用下， 生成 次碘(I)酸 、 碘酸
  参考文献：
  名称：

  碘酸歧化动力学

  摘要：

  所述亚碘酸歧化是自催化的，它是不容易测量的步骤的速率常数2IO 2 ħ→IO 3 - + IOH + H +分开。Hg（II）以前被用来抑制自催化途径，但是这种方法带来了本工作中讨论的困难。一种更有效的方法是使用巴豆酸，一种有效的IOH清除剂。它抑制了副反应，并获得了纯二阶速率定律。速率常数降低为5至0.2M -1小号-1时从0.08硫酸浓度增加至0.60 M.所观察到的下降可解释如果IO 2 -起反应比IO快2H.这可能会对Bray-Liebhafsky振荡反应的机理产生影响。

  DOI：

  10.1002/kin.20791

文献信息

• Iridium(III)-Catalyzed Direct Arylation of C–H Bonds with Diaryliodonium Salts
  作者：Pan Gao、Wei Guo、Jingjing Xue、Yue Zhao、Yu Yuan、Yuanzhi Xia、Zhuangzhi Shi

  DOI：10.1021/jacs.5b06758

  日期：2015.9.30

  arylation of complex compounds. Mechanistic studies by density functional theory calculations suggested that the sp(3) C-H activation was realized by a triflate-involved concerted metalation-deprotonation process, and the following oxidation of Ir(III) to Ir(V) is the most favorable when a bistriflimide is contained in the diaryliodonium salt. Calculations indicated that both steps are enabled by initial anion

  通过开发一种新的 Ir(III) 催化的 CC 交叉偶联，已经建立了一种将酮肟、含氮杂环、各种芳烃和烯烃中的 sp(2) 和 sp(3) CH 键直接芳基化的通用方法。该芳基化的关键取决于适当的催化剂选择和使用二芳基碘鎓Triflate Salts作为偶联伴侣。这种转化具有良好的官能团兼容性，可以作为复杂化合物后期 CH 芳基化的有力合成工具。通过密度泛函理论计算的机理研究表明 sp(3) CH 活化是通过三氟甲磺酸酯参与的协同金属化-去质子化过程实现的，当双氟甲磺酰亚胺包含在二芳基碘鎓盐中。
• Discovery of Novel Pterostilbene-Based Derivatives as Potent and Orally Active NLRP3 Inflammasome Inhibitors with Inflammatory Activity for Colitis
  作者：Liu Zeng Chen、Xing Xing Zhang、Ming Ming Liu、Jing Wu、Duo Ma、Liang Zhuo Diao、Qingshan Li、Yan Shuang Huang、Rui Zhang、Ban Feng Ruan、Xin Hua Liu

  DOI：10.1021/acs.jmedchem.1c01007

  日期：2021.9.23

  Studies have shown that the abnormal activation of the NLRP3 inflammasome is involved in a variety of inflammatory-based diseases. In this study, a high content screening model targeting the activation of inflammasome was first established and pterostilbene was discovered as the active scaffold. Based on this finding, total of 50 pterostilbene derivatives were then designed and synthesized. Among them

  研究表明NLRP3炎症小体的异常激活与多种炎症性疾病有关。本研究首次建立了针对炎症小体激活的高内涵筛选模型，并发现紫檀芪作为活性支架。基于这一发现，设计并合成了总共50种紫檀芪衍生物。其中，化合物47被发现是抑制细胞焦亡最好的一种[抑制率(IR) = 73.09% at 10 μM]，表现出低毒高效[针对白细胞介素-1β(IL-1β)：半最大抑制浓度(IC 50 ) = 0.56 μM]。进一步的研究表明，化合物47通过靶向NLRP3影响NLRP3炎症小体的组装。体内生物活性表明，该化合物可显着减轻右旋糖酐硫酸钠（DSS）诱导的小鼠结肠炎。总的来说，我们的研究提供了一种直接靶向NLRP3蛋白的新型先导化合物，值得进一步研究和结构优化。
• Metal-free amidation of carboxylic acids with tertiary amines
  作者：Wong Phakhodee、Sirilak Wangngae、Mookda Pattarawarapan

  DOI：10.1039/c6ra12801g

  日期：——

  A direct amidation of carboxylic acids with tertiary amines could be carried out in the presence of the Ph3P–I2 activator. With an appropriate reagent addition sequence, a range of carboxylic acids including aliphatic, allylic, and aromatic acids could be converted into their corresponding tertiary amides under mild conditions without requirement of metal catalysis.

  在Ph 3 P–I 2活化剂的存在下，可以将羧酸与叔胺直接酰胺化。通过适当的试剂添加顺序，可以在温和的条件下将包括脂肪族，烯丙基和芳族酸在内的多种羧酸转化为它们相应的叔酰胺，而无需金属催化。
• Exploring the Synthetic Applicability of a Cyanobacterium Nitrilase as Catalyst for Nitrile Hydrolysis
  作者：Chandrani Mukherjee、Dunming Zhu、Edward R. Biehl、Ling Hua

  DOI：10.1002/ejoc.200600699

  日期：2006.12

  specificity and synthetic applicability of the nitrilase from cyanobacterium Synechocystis sp. strain PCC 6803 have been examined. This nitrilase catalyzed the hydrolysis of both aromatic and aliphatic nitriles to the corresponding acids in high yields. Furthermore, the stereoselective hydrolysis of phenyl-substituted β-hydroxy nitriles to (S)-enriched β-hydroxy carboxylic acids and selective hydrolysis of α

  蓝藻集胞藻腈水解酶的底物特异性和合成适用性。菌株 PCC 6803 已被检查。这种腈水解酶以高产率催化芳香族和脂肪族腈水解为相应的酸。此外，还实现了苯基取代的 β-羟基腈立体选择性水解为 (S) 富集的 β-羟基羧酸，以及具有五个或更少亚甲基的 α,ω-二腈选择性水解为 ω-氰基羧酸。这表明来自集胞藻属的腈水解酶。PCC 6803 可能是“绿色”腈水解的有用酶催化剂。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)
• Niobium Pentachloride Promoted Conversion of Carboxylic Acids to Carboxamides­: Synthesis of the 4-Aryl-1,2,3,4-tetrahydroisoquinoline Alkaloid­ Structures
  作者：Claudio C. Lopes、Rosangela S. Lopes、Marcelo S. Nery、Renata P. Ribeiro

  DOI：10.1055/s-2003-36823

  日期：——

  A practical method for the conversion of carboxylic acids to the corresponding carboxamides mediated by niobium pentachloride under mild conditions is described. The synthesis of the 4-aryl-1,2,3,4-tetrahydroisoquinoline alkaloid structures was accomplished via benzylic lithiation of N-methyl-3,4-dimethoxy-2-(4'-methoxybenzyl)benzamide.

  描述了一种在温和条件下由五氯化铌介导的将羧酸转化为相应羧酰胺的实用方法。4-aryl-1,2,3,4-四氢异喹啉生物碱结构的合成是通过 N-methyl-3,4-dimethoxy-2-(4'-methoxybenzyl)benzamide 的苄基锂化完成的。

表征谱图